My journey to submissive sissy and wife : how can this happen ? (5/5)

5. My new life.

Ryan replied that I would never have another man in his home, that I would have no sexual partner other than him—and possibly Jack—that I would manage his estate, accompany him whenever he wished, and be his female companion in every sense, though he would respect me; in return for a personal budget, a car, and a great deal of freedom, I had to obey his requests. I cried a lot for two weeks, thinking about the unknown and the loss of Jack. Then, I agreed to the trial month.

I arrived at Ryan’s place with my four suitcases of clothes, feeling apprehensive. He had set aside a private room for me with a walk-in closet, where I was able to settle in easily. After the morning passed, I was surprised to see him return and take me out to a restaurant. We came back in the afternoon and talked; then he told me he was dying to make love to me. He desired me but wanted things to move gently. He had me stand up and took me in his arms, planting a kiss on my cheek; I turned to offer him my parted lips, which he immediately covered with his own. Our mouths were locked together, our hands busy—mine around his shoulders, then his waist and buttocks, while he caressed my back and bottom, eventually lifting my dress to feel my bare skin and caress my buttocks. Then he pulled back slightly to cup my breasts through the dress and pinch my already hardened nipples. I took the opportunity to feel his fly, opening it to caress his cock. We quickly undressed, leaving him in boxer briefs and me in a thong, bra, and high heels. He sat on the sofa, and I knelt between his legs to slip off his boxers and take his cock in my hands—and then quickly into my mouth. His hands caressed my breasts, sending shivers through me. He soon pulled me down onto the sofa facing him, leaned over to plant a deep, passionate kiss on my lips, then set up, lifted and spread my legs, and impaled me.

"Mmm... Oh, yes... that feels so good." He rode me at a steady pace, heightening both our pleasures. We made love with mounting intensity until he arched his back and shouted out as he emptied himself deep inside me.

"(Ryan) Oh, Anna, my darling, I wanted you so badly. Sorry I finished first, but I’m going to take care of you now." He knelt between my parted thighs and caressed my opening, which was already slick with my juices. He gathered some of the fluid on his fingers and slid them inside, lubricating the way. Then his fingers began to work, and I felt the pleasure rising instantly—waves of it flooding my lower belly, then my whole body and breasts. I began to writhe and moan; I cupped my breasts, pinching my nipples gently at first and then sharply, which sent me over the edge. Once I’d caught my breath, Ryan smiled.

"You’ll need to get ready; we have a reception tonight. Formal attire—a long gown is required. Pick out whatever you like, and I’ll let you know if it works."

I redid my makeup and perfume, styled my long hair into curls, put on my "hardware" (my jewelry!), slipped into high heels and a long evening gown—pink, flared at the bottom, fitted at the waist, with a strapless bodice that accentuated the tops of my bare breasts. Ryan was waiting for me:

"Wow! What a stunning woman! You look amazing! I adore you!"

The trial month flew by, and I had fallen in love! He was so tender, so attentive. Jack had been very directive and stern, and I was his submissive. With Ryan, I felt free and often celebrated; my obedience felt like a choice rather than a compulsion. My role as a woman felt more engaging—I was no longer fading into the background. When Jack arrived at the end of my trial month, Ryan left us alone.

"(Jack) So, how did the month-long trial go?

(Me) Much better than I expected. Ryan is truly attentive and gentle. Plus, he’s just as good a lover as you are. I really don’t know what to do. I want to come back to you, but at the same time, I find him so charming and sweet.

And are you thinking of staying here? It’s your choice.

I think I’d like to; I’d be well treated and freer than I was with you.

Well, that settles it. You’re staying here. Let’s tell Ryan!

(Ryan arriving) So, what has the princess decided?

(Jack) I think she’s going to stay with you—much to my regret.

(Ryan) OK, but you know, Jack, it’s thanks to you—it’s your handiwork. You’re the one who trained her, and in a way, she remains your companion if you want. I’m happy for you two to see each other from time to time, if that’s what you’d like."

- (Jack) You are generous, but I cannot agree to separate you.

- (Me) Oh yes, I see that as a solution. I’ll be Ryan’s partner, but Jack—if you want—we could see each other one afternoon a month, just the two of us, with free rein, provided Ryan is okay with it.

- (Ryan) That sounds like a good solution, I think.”

Since that day, I’ve been living a truly pleasant life with Ryan, and I see Jack once a month—a fitting reward for him having created me. We go out or make love however we please.

After a while, I wanted a good spanking to put me back in my place; I needed it. But how could I tell Ryan, who is so gentle? One day, I adopted the persona of a bratty kid and played the part of a whiny, difficult girl all morning long. Finally, Ryan said to me:

“I don’t know what’s gotten into you, but you’re being impossible this morning. A real rebellious brat! I’m barely stopping myself from spanking you!”

- “Oh yes, darling, you finally get it. I need you to put me back in my place. A good spanking feels like it’s in order.”

- “If that’s what you want to calm you down, okay—let’s do it.”

- “Yes, but know that you can let your anger run its course. I’ll scream, beg you to stop, squirm to get away, then burst into tears and end up sobbing. Once I’m completely melted, that’s when you can stop and hold me tight to comfort me, tend to my bottom, and be very, very tender with me.”

- “You certainly have experience with this!”

- “Yes, Jack spanked me once, and I’d goad him into it whenever I needed it.”

He made me strip naked and threw me across his lap. A few slaps on my bottom, followed by real, hard smacks. This time, he didn’t go too far, but I got what I wanted: a good thrashing and a sore, purple bottom for a week. He got the message, and now, whenever I act like an annoying, rebellious brat, I get a spanking to put me back in my place. I love it.

So, I lead the life of a happy woman, with plenty of female friends to chat, laugh, go out, and shop with. We’re also friends with a few other couples. I don’t have to work, and we live a comfortable life. What more could I ask for?

Hope you are happy for me, and I thank yuou for reading the whole story. Kisses to all.

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u/michelle_sissy100 — 1 day ago
▲ 21 r/cdstoriesgonewild+1 crossposts

My journey to submissive sissy and wife : how can this happen ? (4/5)

4. Discovering Ryan.

Flustered yet submissive, I knelt between his spread legs, lowered his trousers, and grabbed his cock to stroke it. I was blushing with shame at doing this in front of Ryan, but I quickly licked his erect cock and took it into my mouth to swallow it. Jack saw that Ryan was in heaven watching me:

"Darling, I think you should take care of our host, too."

I felt I had no choice—otherwise, I’d surely get a good spanking—so I did the same for Ryan. Once his cock was in my mouth, I set to work, using my skills to suck it deep down my throat, then releasing, licking, and swallowing the whole length again. I could feel his pleasure mounting with every suction, and I began working my throat muscles to caress the cock buried inside me; this made him gasp, then quickly groan, arch his back, and cry out in pleasure as I felt his spurts of cum hitting my stomach. I pulled away and went to sit next to Jack.

"(Ryan) Wow! What a thrill! I can barely catch my breath! Anna, you give a divine blowjob. I’ve never enjoyed myself so much! If the rest is as good as I think it’ll be, I want you for myself!"

"(Me) Oh... thank you so much for the compliments, but Jack was a very good coach. And I’m not sure he’d let me go, nor am I ready to leave him to live with you."

"(Ryan) Of course, Anna. I was just sharing my initial reactions. You’re a divine girl!"

Jack then suggested we take things a step further. We went to the bedroom, and I got on all fours on the bed. Jack took off my thong and spread my legs. Then, right in front of Ryan, he impaled me, making me moan. He immediately teased my sensitive spot with his cock, sending my arousal soaring. Being watched by Ryan only sped things up; I climaxed, screaming and writhing. Jack pulled out and thrust his cock into my mouth for me to suck.

- "(Jack) Ryan, if you want, take my place."

- "(Ryan) Oh no, Jack, I can't do that!"

- "(Jack) Why? Are you scared?"

- "(Ryan) No, but you don't treat a beautiful woman like that!"

- "(Jack) Sure. But we're doing compatibility tests."

- "(Ryan) Anna, do you agree to let me take you?"

- "(Me, with Jack's cock in my mouth!) Yeah, I'd love for you to try!" He moved behind me; his soft, caressing hands found my hips, then my waist, before moving up to cup my breasts and pinch my nipples between thumb and forefinger. It sent electric shocks through me—sensations that intensified, heightening my desire and my need to be taken! As I moaned, he asked:

- "Anna, do you like my touch? And are you ready to take me inside you?"

- "(Me, still with a mouthful!) Yeaaah, Ryan, take me—I want it."

I felt his hands on my buttocks, spreading my hole open as his cock head pushed against it. He gripped my waist again, holding me steady as he slid inside without any pain. Once he was fully in, I felt his balls against my sex; then he began to pound into me, picking up the pace. I gasped and met his thrusts, impaling myself on his cock and pulling back against it! It felt amazing; my body quivered with pleasure at being sandwiched—Jack’s cock in my throat and Ryan inside my pussy! It was probably the most humiliating position for a woman, yet also the most sensual—the ultimate assertion of my submissive role. I was truly a female in heat, a slut desperate to be fucked! I felt Ryan stiffen and thrust deep inside me in one go, emptying his load while he cried out. Jack grabbed my head, ramming his cock deep down my throat and holding me there, breathless, so he could empty himself too. I struggled for air, but it was no use—I was trapped between the two males! Once I caught my breath, I loved what had just happened to me: confirmation that I was a desirable woman who’d been thoroughly fucked.

- "(Jack) So, darling, did you enjoy it?"

- "(Me) Yes, in a way; I was overjoyed by the pleasure I gave you and the pleasure I experienced myself. Ryan is a good lover."

- "(Ryan) Thanks, but that’s not all I’m looking for. I want a real, full-time life partner—someone for sex, certainly, but also someone to be by my side during trips, social events, or even when entertaining clients. You’re well-read and look lovely, which could make you the perfect partner for me, if we can come to an agreement."

- "(Me) It all depends on the terms. But what about Jack? I was a rather shy, lost young man when Jack helped me. He introduced me to things I’d never even imagined and showed me I could become a woman. That’s when we fell in love; I came to rely on him, became a fulfilled woman, and happily became his partner. We’ve had a full life since then—I have a partner and a job I love, and I’m happy. Why would I leave all that to live with you? I owe everything to Jack; he created me, and we love each other—as husband and wife."

- "(Ryan) I understand. I was just making an observation: a woman like you is exactly what I need, and I’d know how to make her happy."

- "(Jack) Perhaps, but you have to find one."

Later that week, Jack brought up Ryan’s situation again. He’d known him for a long time and knew him to be a serious, wealthy man. "Anna, I saw you when the three of us were together, and you looked very happy. What do you think of him?"

- "It’s true, he’s great. He’s pleasant to talk to, very charming and tender with women, and a good lover." "But I don’t want to leave you!"

"That’s not the point. I’ve seen how much you enjoy it when he caresses you, kisses you, and makes love to you—just as much as when we’re together. Besides, he’s younger than I am, and we can always still see each other as friends."

"But I don’t want to be involved with two men! I’m with you."

"What if I suggested you spend a month with him—as his temporary mistress? I’d be lending you to him so you could give it a try."

"You’d do that? So you don’t love me?"

"Oh, I do, my darling, but your happiness comes first. I think he could step in and fulfill you even more than I do."

"That remains to be seen. First of all, what would his conditions be?"

See my actual life on next and last part. Good reads.

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u/michelle_sissy100 — 2 days ago

My journey to submissive sissy and wife : how can this happen ? (3/5)

3. Jack wants me to broaden my horizons.

One day, he told me about a friend of his who was looking for a partner to live with him as a woman. He asked for my thoughts on the matter.

"Anna, given how far you’ve come on your journey toward embracing the role of a woman, what do you think about that?"

"I don’t see myself as a woman."

"You haven’t really looked at yourself in a long time. When you’re here with me, all I see is a submissive, desirable girl—sexy as hell!"

"In real life, I’m a man. As much as I’m hooked on you—and want you to use me and pleasure me—I don’t want that life 24/7."

"You’re really disappointing me. I thought I’d molded you into a woman."

"Yes, in our private moments, but not in everyday life!"

"Listen, the way you look right now, you could walk out onto the street and be seen as a real woman."

"No, I’d be laughed at immediately!"

"Oh, absolutely not. Want to put it to the test?"

"Why not! You’ll see!"

He had me dress in a loose, low-cut dress with spaghetti straps that revealed the tops of my small breasts, a shoulder-length curly wig, and full makeup (foundation, eyeliner, mascara, dark lipstick, and nail polish), along with high heels, a handbag, and accessories (necklace, earrings, bracelets, rings...). It’s true—in the mirror, I looked every bit the beautiful, desirable woman. When we went for a walk in town, no one paid me any mind, and I was completely shaken. Was he right? Had I become a woman? The shops and the restaurant dispelled any lingering doubts: I could truly pass as a woman in public; his training had gradually transformed me into one! On the way back:

"So, darling Anna, what did you think of our outing?"

"I have to admit, I’m amazed that I can pass as a woman in public. Is it possible that I could one day live as a woman and find a partner?"

"That’s up to you. No one will force you to do it; it’s your choice."

"Hmm... yeah, that’s something to think about. What would become of my life? My job, my family?"

"That’s for you to consider. But you should know that Ryan is a very wealthy man; if you became his wife, you wouldn’t have a single financial worry. You’d just have to look after him, appear on his arm at receptions, and satisfy him sexually."

After much reflection, I finally told Jack that we ought to meet at least once to see if there was any mutual chemistry. So, I agreed to a date with him. We went to the restaurant where Ryan was waiting for us. A handsome man in his forties, exuding confidence, greeted me by kissing my hand. "Hello, my dear Anna. It’s a pleasure to meet you."

"Thank you."

We spent a long time at the table, having an engaging conversation about various topics, before eventually discussing his desires. He knew about my past as Michael, and Jack explained everything we had done together.

"(Ryan) It seems to me that you’ve come a long way. You’ve become a very lovely woman—well-educated and knowledgeable—and you know how to conduct yourself at the table and in conversation. That’s part of what I’m looking for: a companion who reflects well on me. The fact that you still have a male body doesn’t bother me. Above all, I want a sexual companion who knows how to take care of a man, but the condition is that I never want to see you dressed as a man. Of course, my companion would be free not to work—just looking after the house and doing me proud—with a budget at her disposal to keep herself looking beautiful."

- (Me) "I see you’ve clearly defined what you’re looking for. I like that. But I think a more intimate meeting is necessary before making a final decision. Liking each other during a meeting is one thing; finding each other appealing intimately is another. We need to talk about it and try things out."

Following that first visit, Jack suggested a threesome. He wanted me to show Ryan what I could do and how I behaved, to ensure I was the right choice. During the encounter, Jack had me stand up; then, stepping behind me, he lifted my dress and removed it. I found myself standing there in a bra, thong, garter belt, stockings, and high heels, facing Ryan, who was smiling with satisfaction. Then my bra was taken off. I felt so embarrassed! But Ryan was pleased:

- "Well, I didn't mean to make Anna uncomfortable; I didn't want you to undress her! Poor thing—being topless in front of me must be humiliating!"

- (Jack) "No, I wanted you to see what Anna is like and whether you’d be into her."

- "With what I’m seeing, you’d have to be crazy not to like it! I love those curves, that slender waist, and those superb breasts!"

- "(Jack) Anna, can you come take care of my cock now?"

See you soon on next part.

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u/michelle_sissy100 — 2 days ago

My journey to submissive sissy and wife : how can this happen ? (2/5)

2. I find a friend to train me. (2/5)

Then one day I met Jack, under similar circumstances. After a few afternoons together, he started asking me questions.

- "How do you see your future? Are you going to become more feminine—feminize yourself—and how will you go about it?"

- "No, I’m not thinking about that at all. Why?"

- "Let's just say you have quite a bit to learn. Right now, you just show up looking like a guy in a costume."

- "For starters, as a guy, I find it impossible to let myself go in another man's arms. I become submissive the moment I’m dressed as a woman, and my tiny cock hides between my thighs. That way, a man can take care of me and make love to me."

- "I see. But for instance, you don't know how to handle a cock. Has a girl never sucked your cock? That’s what men like the most."

- "No, but... well, I can improve."

- "If you want, I can teach you."

At our next meeting, in his bathroom, he applied lipstick and mascara to me and said, "There, that’s better." Then he made me kneel and slid a ruler into my anus. "Can you hold that in place for a moment?"

After a while, he came over and said, "Not bad; you’ve got a nice, tight ass."

Then he made me bend forward and inserted an object, pushing it into my ass, which was struggling to open up! When I moaned, he stopped. "I see you have a small opening. We need to work on opening it up more. Now, suck me off."

He sat on the bed, and I knelt between his legs. I was caressing him when he said, "Slowly—top to bottom—and keep your mouth on the head." I did just that, running my tongue over it. "Yeah, well, learn to love it!" I lick him from bottom to top, then start opening my mouth to take him in. I move back and forth over his head, and he seems to like it. Then I feel his hand on my head, pushing me deeper each time. I quickly feel him hitting my uvula, which makes me cough, and as he persists, I start gagging. I endured this treatment for a good half-hour; it left me drained and nauseated. What is enjoyable about feeling sick? Yet he gets his kicks out of torturing me like that!

On my way home, several people looked at me and laughed. When I checked the mirror, I saw I hadn't taken off my makeup! I didn't want to see him again. But two weeks later, I was calling him to set up another meeting!

"So, big girl, feeling better? Come on, let's get your makeup done." I got the full treatment—mascara, eyeliner, lipstick—and a wig that made me look like a woman! He took off my dress and bra, then placed two suction cups on my chest and pumped them up; the pain made me look down: the cups were filled with the skin of my chest, and I now had two real breasts beneath them. Four-inch heels made me wobble a bit, but since I was used to three-inch ones, I quickly learned to walk in them. Jack corrected me: "Women don't walk like that; your feet need to step one in front of the other in a straight line, and the heels create that hip-swaying motion that’s so feminine, so typical and sexy."

So, I went through a session on walking and posture—sitting, walking, standing, and adopting feminine mannerisms—followed by a cock-sucking session, all while keeping my breasts inflated! He would only make love to me right at the end, once I’d done what he wanted. Several times I felt like stopping seeing him, but I always ended up craving his cock. I kept seeing him, and each time my breasts were pumped; as a result, actual small breasts soon appeared, and my nipples grew larger. I always got his cock down my throat and endured his lessons, and in the end, he’d take me. We established a ritual: I’d come to his place on Saturday at noon, transform into Anna, and spend the afternoon undergoing training and being used however he pleased. I’d sleep over as a girl, and Sunday morning meant another session, new tasks, and more sex, before I headed home after changing back into Michael.

He put together a little wardrobe for me with the outfits he wanted me to wear—always very sexy, high-cut, and short; in short, very "slutty," especially the makeup (though in private, it didn't matter). I even had to show up with my fingernails and toenails done ! I learned quite a bit about femininity from him. I can now deep-throat without gagging; when he’s really full down my throat, I can move my throat muscles to massage his cock, and I manage to make him empty his load right into my stomach! It’s hard to learn, but now I love doing it for him. He also taught me how to build up pleasure while jerking him off or sucking him, then stop at the right moment—squeezing the base of the penis hard—just before the climax, let the sensation subside, and start again. It makes the explosive orgasm incredibly powerful when it finally happens. He even performed this massage on me himself, and I had a divine orgasm; I nearly passed out from the pleasure!

He also taught me that when getting fucked, depending on the position, you can have an orgasm (without ejaculating, just like a woman, and multiple times in a row). I’ve become truly addicted to this prostate stimulation. Now I can’t go without visiting him; I’ve become his little submissive slut, entirely at his service. When I’m with him, he can do pretty much anything to me without me putting up a fight. The only times I rebelled against his demands, he made me lie face-down across his knees and gave me such a severe bare-assed spanking that I’d writhe, cry, and sob, begging him to stop and promising to accept anything—but nothing worked; he’d unleash all his pent-up aggression on me. Every time, I struggled to walk for a good week, and sitting down was even harder. But with the time passing, looking back, I think I’d be a bit of a bitch and a pain in the neck from time to time, just to get a good spanking at home. The idea appeals to me. From his perspective, I’ve become a sexy, alluring female—submissive and well-trained for her man’s pleasure, yet capable of being a real slut.

Thanks for reading my story guys, See you soon for next part. I wish you get good vibes.

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u/michelle_sissy100 — 3 days ago

My journey to submissive sissy and wife : how can this happen ? (1/5)

1. My discovery.

I used to be Michael, a man of action, but during several relationships with women—lasting anywhere from four to thirty months—I became curious about women’s lingerie. In secret, I would put on panties, thongs, and bras (which I padded with socks). I loved the silky texture and the sensation of the fabrics constantly caressing my skin. That’s how I started caressing my anus—which felt good—and then using objects for penetration, which gave me a pleasurable feeling. When I caressed myself while wearing women’s lingerie, my cock didn’t matter; it stayed soft and small. The only thing that mattered was the sensation of penetration. I soon began to wonder what it felt like for women to be penetrated—and fucked in the ass—by real cocks. With that idea constantly on my mind, I tried to arrange a hookup with a man willing to make me his female, just so I could find out. The first time, I arrived at Alex’s place; he put me at ease and showed me to the bathroom so I could change. I had brought a matching black lace thong and bra, a garter belt, seamed stockings, three-inch heels, and a wig. When he saw me, he smiled:

"Oh, you look beautiful! Come sit down and have a drink."

I was feeling pretty nervous.

"Calm down; we’ll go at your pace. Just tell me if anything feels wrong. To me, you’re just a beautiful girl. What’s your name?"

"Um, I don’t know yet."

"How about we call you Anna?"

"Okay, if you like." "Alright then, Anna: I’m going to seduce you, kiss you, and caress you all over; then you can take care of my cock, and when you feel ready, I’ll lube up your hole with some saliva and we’ll see how it goes. Just be confident—and the more relaxed you are, the better it’ll be; no pain." He caressed my face, breasts, and stomach, noting my flat midsection with an "Ohhh, nice flat tummy! I love it!" Then we stood up, facing each other in his arms, and kissed deeply; I felt his hands under my dress, groping and patting my bare buttocks (my thong hid nothing!). A touch on my shoulders told me it was time to act, so I slipped off my dress. "Oh, fuck, you’re so desirable! Such a gorgeous little package! I have a feeling we’re going to have a great time!" I knelt down in front of him, lowered his trousers, and revealed his already rock-hard cock. I took it in my hands—the first cock other than my own that I’d ever touched—and moved my hand up and down the shaft just as I used to do with mine. He caressed my cheeks and breasts while I looked up at him. At one point, he said, "Anna, are you ready for the next step?"

- "Yes, I think so."

- "Right, we’re going into the bedroom; get on all fours on the bed, legs spread, back well arched with your ass in the air, and stay as relaxed as possible."

There I was—dressed as a woman, my private parts completely exposed to a stranger who was about to penetrate me! Such vulnerability; yet I obeyed without a second thought. I felt him step between my legs and spread them, then he felt my buttocks, giving them a few light taps: "Mmm, I love the view!" Then his hands moved to my hole—caressing, penetrating, and lubricating it with saliva—and I felt one, then two, and finally three fingers slide inside. "Anna, my dear, relax; see, it’s painless, and afterwards you’ll feel pleasure. I’m going to take you now."

I felt one hand grab my hip just above my garter belt, while the other guided his cock. With the head resting against my hole, he pushed gently, and I felt my insides gradually opening up. Then he stopped. "Almost there; just the ring left to get past, and then it’ll be open." He resumed pushing, and I felt my body stretching further—to the point where the pain was starting to set in.

- "It’s starting to hurt; the pain is coming on."

- "Just wait a little longer and the discomfort will vanish. Then I’ll be able to take you fully."

He pushed again, and I felt a tearing sensation—"Ouch!" At that moment, he pulled me in by the hips and thrust deep inside me. I could feel his balls slapping against my genitals!

- "So, my dear, how does it feel? You’re impaled right down to the hilt on my cock."

- "It’s okay; the pain is almost gone." »

He starts thrusting slowly, then picks up the pace. It feels good; a pleasant sensation washes over my lower belly, making me moan softly. Alex is completely caught up in his mounting pleasure; after a few minutes, he arches his back, thrusts deep inside me in one powerful motion, and explodes within me with a shout.

Later, as we sit on the sofa in the living room, resting with a drink, I can feel his juices trickling down between my thighs!

- "So, Anna, you wanted to know what it was like to be a woman."

- "Yes, I found out, and it wasn't unpleasant. I loved feeling your cock vibrate and empty itself inside me."

- "You’re a real woman now—a little slut!"

- "Oh, I was just curious."

- "Fair enough, but if you want Anna to come see me again, just let me know. I enjoyed it."

I saw Alex a few more times with great pleasure before he moved far away.

I went back on the prowl and, in the same way, was with several other men for whom I played the female. As the saying goes, you can't change your nature; we’re drawn to the forbidden, to novelty, to pleasure—and so we do it all over again.

se you soon for next part. Hope you enjoyed.

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u/michelle_sissy100 — 3 days ago
▲ 30 r/SissyRewired+1 crossposts

Forced fucked, years later a nice guy show me anal pleasure and I become his sissy. (5/5)

5. Emily’s Journey.

I kept going, improving with every step: different dresses, skirts, and tops; tights and stockings for winter; various wigs; high heels in different heights and styles—basically, the whole feminine wardrobe. Then, one day, I had the chance to try a breast-enhancement product, which I quickly put to the test. After three months, the result was a slight roundness beneath my nipples; I finished the box but stopped using it. I hadn't considered that this sort of thing isn't a device you can just switch on and off—it involves the human body. Girls develop natural breasts over the course of several years. Even though I had stopped taking the products, my body—having been stimulated—continued the process on its own. One day, seeing me naked, Alex said, "Oh Emily, that’s amazing—you have breasts!" I looked down and indeed saw curves forming beneath my prominent, pointed nipples. I caressed them, and the touch sent an electric thrill through my skin; my nipples made me shiver! The effect intensified gradually: my areolas swelled, pushing my nipples outward and forming a secondary mound atop the curve of my breasts, which continued to grow. I ended up with real, natural breasts, moving from a B-cup to a C-cup. They are my pride and joy, and Alex loves caressing them! Now I can go out wearing nothing under my dresses and show them off with a plunging neckline!

As time went by, I lived more and more as a woman—except at work. Then, one day, Alex sat me down:

"Emily, do you still want to live this life in between two worlds? I want you, I love you, and I’d be the happiest man alive if you came to live with me full-time."

- "I love you too, but I’m happy the way things are; we’re happy."

- "If you’re willing, I’d love for you to quit your job and come live here with me—well, with *us*. We’ll find a job for a beautiful girl like you!"

- "Hmm! I’m not so sure. I don’t really know how to be a woman; my voice has adapted, sure, but walking and living in heels, or having feminine mannerisms—that’s hard for me."

- "We’ve been through tougher learning curves than that, you and I! And now you’d back down over a few more lessons?"

- "You might be right."

After giving it some thought, I moved in with Alex a while later and became his attentive little female. He took great care of me and guided me through my feminization. I found a suitable job I enjoy, and life as a couple resumed. I became even more sensual than before with my female body: real, highly sensitive breasts; a rounded bottom; slimmer hips creating a feminine silhouette; and a cock tucked away in a thong between my thighs to give me a flat, feminine lower belly. In fact, I hardly ever use my cock during sex anymore. All I dream about is being thoroughly fucked several times a day and tending to a nice, hard cock with my hands and mouth. At home, I always go without underwear, wearing a dress or a skimpy top and skirt. This leaves the tops of my breasts—which jiggle when I walk—exposed and open to caresses, along with my bare bottom under the dress. Alex certainly takes advantage of that. Whenever the mood strikes, I corner him, pull down his pants, and—right between his legs—take his cock into my mouth; I love swallowing it and licking it, sometimes even drinking his juice. Alex takes full advantage of my breasts and doesn’t hesitate to reach under my dress to smack my ass; every now and then, he pins me down and impales me on his cock. I love it! I’m addicted to having his cock inside me! Sometimes I can barely handle the orgasms, but I take everything he gives me! As he told me:

"Emily, you’ve really turned into a woman made for fucking! You’re so sensual, you act like a total slut, and you give divine head! And don't get me started on your ass—such a welcoming cock-sleeve! You’re a real man-eater! I adore you! I can’t live without you! I never imagined things would end up this way when I started training you—or that I’d fall so hard for you—but now I’m crazy about you; you’re my woman!"

"Thank you, darling; hearing that makes me so happy. I’m addicted to you too; I need to feel your cock inside me—in my mouth or my ass—and feel your cum flowing into me. I crave your touch and the way you smack my skin, my tits, my slutty ass, and my pussy. Day in and day out, you’re a wonderful lover and an adorable, attentive husband."

That’s where I am in life now. John is out of the picture, and I have no regrets. We love each other and have a rich life—we have friends and go out a lot. Everyone knows me as Alex’s wife now, and I couldn't be happier. I don't think like John anymore; I truly feel transformed into Emily, with no regrets.

Reflecting on my life as a woman.

What can I say about my life as a woman? Above all, I think my petite frame and my reserved, quiet nature predestined me to be dominated. As a woman, I am attentive to my man—I am his submissive, and that suits me perfectly. In this way, I’ve found my place and truly blossomed. I am an approachable person who listens to others; I’m always ready to offer help or comfort, and I always wear a smile. Men’s grooming rituals are very limited—they spend barely fifteen minutes a day in the bathroom. I, on the other hand, have flourished in feminine rituals; I love taking care of myself and my body. I have long hair that I style in many ways—braids, highlights, curls in various colors—and I wear makeup and care for my skin every day. I massage (and caress) my breasts, remove every last trace of body hair, keep my nails polished, apply lotion all over for beautiful skin, and wear perfume and jewelry. I love it when men look at me; it makes me proud. After all, a woman’s primary role is to please men and attract them. I love playing the vixen, often showing off my breasts—especially when I lean forward—and when I’m sitting on a café terrace and catch men glancing my way, I often find myself spreading my legs (frequently without underwear!). They end up blushing because they can’t see a thing; my tiny genitals are tucked away between my thighs and remain invisible. Without even realizing it, I have fully and happily embraced the feminine role of attracting men. Indeed, I find the feminine way of dressing and behaving much more enjoyable. We have a huge selection of clothes—dresses and skirts ranging from mini or even micro to long, whether form-fitting, flared, or pleated; tops that are tight or loose, strapless or with straps, short-sleeved or long-sleeved, and in every imaginable material (I love lace outfits and lingerie). And don't even get me started on shoes: everything from ballet flats to five-inch heels and platforms. We can style our hair in so many ways—long, short, straight, curly, braided, in pigtails, or in a bun... I have a blast playing with all these possibilities that men don't have. It takes time, but I love it.

In my daily life, I have a job that involves interacting with the public—something I really enjoy.

When I'm out and about, I find it easy to connect with people; I always have an open, smiling face, which is why we have quite a few friends. I truly believe that thanks to Alex, I’ve found my place by becoming a woman—both in my mind (I think and act like a woman) and, to some extent, in my body (my breasts and my now-useless male genitals).

I hope you enjoyed my story and found it entertaining.

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u/michelle_sissy100 — 11 days ago

Forced fucked, years later a nice guy show me anal pleasure and I become his sissy. (4/5)

4. Becoming a woman?

One day, Alex arrived and handed me a bag:

"I thought you might like to see yourself for real. Try this on."

Inside the bag, I discovered a short, flared dress, a cute thong, low-heeled shoes, a woman’s wig, and makeup. Seeing my look of bewilderment, he said,

"Give it a try; you’ll see yourself differently. I can’t wait to see Emily—the name my childhood friends gave me when I used to play a girl’s role—in the flesh. It’s just a role, for the fun of the memory."

Reassured, I went to the bathroom and got dressed. Looking in the mirror, I had to admit that my body allowed me to put on the dress and wig for a whole new look. I liked what I saw, so I finished the look with a bit of foundation, lipstick, and the shoes. I hardly recognized myself in the mirror! Could it be? Was I meant to be a girl? In any case, I liked it.

When Alex saw me walk out, he let out a "Wow," left speechless. "What a beautiful girl! You look radiant! I’m proud to have brought Emily out! You’re a beautiful girl—you make a guy want to hit on you! Are you ready for our afternoon out as a couple?"

"No, Alex, I’m not a girl, despite the outfit."

"You look too good; it would be a shame not to make the most of it!"

"Okay, just once."

And Alex, despite my reluctance, took me out on his arm, dressed as a girl. We went for a lovely walk—no one gave me any strange looks—and once we got back, he took me in his arms and planted a deep, passionate kiss on me without warning. I was completely overcome, and he took the opportunity to caress my breasts and then my buttocks under my dress; he removed my thong, stood me up in front of the sofa with my hands on the backrest, spread my legs, lifted my dress, slapped my ass, and wet my hole before impaling me on his fully erect cock. I let out a sound—"ooooohhh aaaaaahhhhhh rrrrr ggggg hummmm"—of surprise and pleasure. He quickly grabbed my hips and thrust into me at a rapid pace, sending intense sensations coursing through my entire body and quickly driving me to a shattering orgasm! He started up again the moment I caught my breath, and with just a few thrusts, he shot his load deep inside me! We sat on the sofa to rest, and as I slumped there with my legs spread, I could feel Alex’s juices running from my ass beneath my dress. I had to go wash up. When I returned:

- "I’m blown away! You look so beautiful as a girl, and you’re amazing in bed! I’m crazy about you! I’d love for us to live together as a couple—me and Emily!"

- "Don't count on it! I’m John, and that’s how I’ll stay."

- "Don't you like the way you are right now?"

- "Of course I do, but I can't live like this—especially not with you, my buddy!"

- "People can always change their minds. But look—in public, nobody pays us any attention. We just blend in with ordinary people: just another couple. I’d happily make you my wife!"

- "I’ll never be a woman."

- "Yeah, I get what you mean. But now, after everything we’ve done, we know each other inside out! It only took a few clothes to reveal your true nature. You’re comfortable as Emily, and you *could* live like this."

- It’s too soon; we’ll see.

- Look, we can give it a try: from now on, whenever you come over, you come as a girl.

- From my own place? I don’t think so!

- It’s the best way to see how you react when you’re out in public on your own.”

So, I left with the clothes in my bag and returned to Alex’s place as Emily. But I completed the look with nail polish (fingers and toes), blush, mascara, eyeliner, earrings, rings, bracelets, and a handbag. I even bought my first push-up bra—which I stuffed with socks to create the illusion—and a pair of three-inch heels. I loved what I saw in the mirror: a proud female body, all dolled up for her man, with a totally convincing bust that looked nothing like John’s!

When I arrived at Alex’s, he didn’t recognize me at first! “Wow! You look absolutely stunning, babe! Great makeup and all the accessories of a real girl! Come suck me off right now!” Kneeling between his legs, with his cock sliding in and out of my throat, he stopped me with his hand: “No, I’m fucking you right now—you look too good, I can’t hold back!” He grabbed my hand, pulled me up, and pressed me against the sofa with my legs spread; he lifted my dress and impaled me in one thrust! The fast, wild ride sent me to heaven just as he drove his cock in deep and came inside me! That was the moment I decided to truly become Emily—if Alex would have her as his girlfriend.

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u/michelle_sissy100 — 12 days ago

Forced fucked, years later a nice guy show me anal pleasure and I become his sissy. (3/5)

3. Pleasure was the order of the day.

Discovering the pleasures of my body moved on to my nipples, which quickly became very sensitive. We had reached a turning point. Was Alex going to suggest anal sex? One day, after sucking each other off, we sat down to rest with a drink.

"Tell me, John, where do you stand?"

"You’ve helped me discover so many things—thank you for that; you’re a great teacher."

"You’re not answering the question: what held you back when you first mentioned it was the aftermath of your assault. Where do you stand on that now?"

"I’ve come to understand that the rear end is a huge source of pleasure, too, if you know how to go about it. You aren't actually planning to sodomize me, are you?"

"You also know that for the person being sodomized, granting their partner free access to their most intimate self is the ultimate act of trust. That trust has to be absolute."

"But I *do* trust you... though going that far..."

"Far as what? Letting me penetrate you? Haven't I always been gentle with you? I’ve never rushed you."

"Yes, that’s true, but... well, I don’t know."

At our next meeting, Alex said:

"So, have you thought about it? Are you ready?"

"Yes, I’ve thought it over, and I’m willing to let you try—but if I scream, you stop."

"Of course, just like always. So, ready?"

He had me get on all fours on the bed, legs spread, my ass pushed back toward the foot of the bed—I felt so ashamed in that position! He moved behind me, slapped my buttocks to help me relax, and caressed my limp cock; then I felt the head of his penis—coated in gel—against my hole. His hands gripped my hips, and he pulled very gently. I feel my hole opening up—just like with the dildo—and then it slides gently inside me, pain-free. As soon as his balls touch my anus, he says:

"There you go, John—you’ve got a real cock deep inside you. You okay?"

"Yeah, for now."

"What? The hard part’s over; now just focus on the pleasure I’m giving you."

He starts thrusting, but presses down on my buttocks to lower me, and I feel the sensations shift. He uses the head of his cock to stroke the exact spot he usually plays with his fingers to make me cum. I think it’s my prostate; it triggers those familiar electric jolts deep in my lower belly—sensations that radiate all the way to my nipples. It doesn't take long for me to start writhing and moaning under his thrusts! I feel the pleasure rising in massive waves, and suddenly, I arch my back and groan as I climax. I’ve just had my ass pounded—and I loved it; I even came! After that victory, Alex took me several more times.

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u/michelle_sissy100 — 12 days ago
▲ 51 r/SissyRewired+1 crossposts

Forced fucked, years later a nice guy show me anal pleasure and I become his sissy.(2/5)

2. Discovering the possibilities.

I complied hesitantly, taking his cock in my hands. Instinctively, I began to stroke it gently. It was proudly erect and smooth to the touch. "So, is it unpleasant, or do you like it?"

"Yes, it’s nice to look at and stroke."

"And are you getting hard?"

"Uh, yeah—really hard."

"So you enjoy it. Now, do you want to lick the head?"

"Yeah, why not!"

I found myself licking the head, which had a slightly sweet, not unpleasant taste. Instinctively, my tongue moved up and down, until I surprised myself by opening my mouth and wrapping my lips around it. I started sucking his cock, moving faster and faster from base to tip. Alex began to groan. At one point, he placed his hand on my head and pushed down, filling my mouth completely with his cock. I struggled to breathe. Then he let up, and I started again. He guided me with his hand, pushing down a little harder each time, making me gasp for air and struggle. Then, suddenly he stopped : "There! You’ve got my whole cock down your throat—you’ve become a pro at sucking cock! How do you feel?" (He let go of me.)

"Mmm... ouch, a bit out of breath, but it’s erotic to let yourself be guided."

"Yeah, you get hooked on the good stuff quickly—even the rougher parts. You’ve become a sucking expert!"

The next day, we swapped roles, and he sucked me divinely, making me cum deep down his throat. Thanks to him, I was discovering pleasures I’d never imagined, and my trust in him was growing. The following week, as soon as I arrived, he said: "John, given what we’re planning to do together, it’s easier if we both strip naked."

Once that was done: "Right, tell me—aside from your own experiments, do you know the pleasures of anal play? Do you have any toys?"

"Not much. I’ve stroked my anus, then used lube and moved my fingers in and out. Now I have a dildo that I use to simulate being fucked, changing the speed and angle to get the best sensations."

"Okay, relax completely—get comfortable on your knees in front of the sofa, leaning forward—and use it however you like."

I did as he said, feeling a bit of shame at doing something so intimate while my buddy watched. After a while, he came over to me: "Don't move, take out the dildo—I'm taking over."

"Oh no, please, not that!"

"Don't you trust me? I won't do anything to hurt you!"

"Okay, but be gentle."

He took the dildo and stroked me with it, but with a precision that sent incredibly pleasant, novel waves of sensation through me; then he removed it. I felt his hands approach; one hand stroked my hard cock, while the other slid one, then two saliva-coated fingers inside me. I struggled to relax and let him in. Once they were inside, I loosened up a bit, and the sensation felt just like using my dildo. His fingers gradually began to move, and it felt good—I even started getting little shivers of pleasure that came more and more frequently. The spot he was caressing inside sent flashes of sensation radiating through my lower belly. The more he caressed me, the higher the tension rose, and I found myself moaning. Then, at one point, I couldn't hold back anymore; a jolt of pleasure washed over me, and I gasped out, "Oh yes, that feels so good!" Alex then said, "So, you see now that the back is worth exploring."

"I didn't know it could feel this good."

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u/michelle_sissy100 — 13 days ago
▲ 93 r/SissyRewired+2 crossposts

Forced fucked, years later a nice guy show me anal pleasure and I become his sissy.

1. My beginnings.

As a young person, I spent my holidays with family—uncles, aunts, and grandparents—who were all farmers. We played with whatever we could find. We loved dressing up and role-playing; since I was slight of build, I often played the princess or similar roles, and I adored being a girl among the girls. I loved wearing their dresses, having them style my hair, and listening to their conversations. I spent long, happy days living as a girl—staying that way from morning until evening, when the adults would laugh and call me "Emily." Yet, the very next day, I would eagerly look forward to another chance to play a female role.

As I grew older, I discovered women’s lingerie; I tried on my mother’s and sister’s things, and eventually, I dared to wear them all day long. It felt so good to have those silky fabrics slide against my skin, and nobody seemed to mind! Like many young people, I experimented by touching my hole and then inserting my fingers, as it gave me a pleasurable sensation. Later, I bought a dildo and used it frequently for pleasure.

Then, one day when I was twenty-two, I was out for an evening walk; on my way home, I was stopped by three young men looking for trouble. They took my wallet, and since I didn't have a phone, they tried to search me. That’s when one of them spotted my underwear: "Hey guys, he’s a faggot! Look at this!" They shoved me into a secluded spot and pulled off my trousers. I became a laughingstock; then one of them said, "Well, without a phone, we aren't getting our cut—let's take it out on him instead!" It was fortunate that I had used my dildo often, as the way was already open, but I absolutely hated that moment. I was forced onto all fours, and all three of them raped me, taking me quickly and ejaculating in their pleasure. I was furious, and tears streamed from my eyes. They left me like that. When I got home, I cleaned myself up and went to bed.

It took me a long time to recover and to wear thongs or stockings under my clothes again. But the desire for pleasure was stronger, and I moved past it. I had a few flings with nice girls, but the trauma was too deep, and the relationships didn't last. I used to talk about it with my childhood friend Alex, whom I saw from time to time. I even worked up the courage to tell him about my ordeal. He was shocked and told me I could count on him for help.

Through our conversations, he really convinced me that it wasn't a disaster—it was just a matter of finding a way to engage in certain practices better, and above all, with someone I trusted. He explained that in a successful relationship, there is an "active" partner (often the man, though not always) and a "receiver." The receiver needs to have complete trust in the other person, because they have to let go and accept the other taking control. He was willing to help me, but he made it clear that I had to trust him implicitly—to submit to him, in a sense, and hand over control of my entire being. There would be moments that were hard to accept, but the results would be worth it. He started by telling me that the time we spent together would inevitably be sexual in nature, and that I would have to submit or else ask him to stop. With my consent, we met at his place for the first time. To ease into things, he wanted to see if I was truly willing to submit.

"John, are you sure you want to obey my orders and let me go as far as I want in my exploration?" - Yes, Alex, you know I need to break out of my shell, and I think you’re one of the people who can help me do that.

- OK. First off, tell me: have you ever had the chance to suck a guy’s cock?

- No—you’re kidding!

- See? You’re already hesitating!

- No, Alex, and I’ve never even wanted to.

- What about a woman’s pussy?

- Yes, of course! They like it, and it’s not unpleasant to do—especially when the tension builds and the pleasure kicks in.

- Well, you see, it’s not unpleasant. Now, I’m going to show you what can be done to a cock. First, get on your knees between my legs, take my dick out of my shorts, and hold it in your hands.

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u/michelle_sissy100 — 13 days ago

FORCED FEMINIZED TO HAVE A VERY NICE JOB .( 5 /5)

5. I carry on going on sea excursions.

Being out of work, I couldn't afford to refuse. So I accepted, though he told me to come see him beforehand. He gave me enough money to put together a feminine wardrobe and buy all the necessary makeup. Two of the couples—Caroll and Lisbeth with their husbands—had requested my presence on board, on the condition that I remain "Chloe" at all times, though I was also free to sleep with the women if they asked. I also had to visit a nurse who administered an injection; it was designed to make me feel completely like a woman and allow me to wear tiny bikinis that still concealed my genitals. When she gave me the shot, she made me sit down because my legs had gone weak. My head was spinning; I felt an electric jolt in my torso followed by a tingling sensation in my breasts. I tried massaging them to soothe the feeling, but it only gave me shivers of pleasure and made my nipples incredibly sensitive. Carrying my bag and all the gear needed for my life as a woman, I arrived at the boat wearing a tiny bikini under a beach cover-up, fully made up with a shoulder-length curly wig and 4-inch summer wedges. My torso was still tingling, and the way the fabric brushed against my nipples sent delicious yet unsettling vibrations through me. Everyone seemed happy to see me arrive as a woman and complimented me on my transformation. During those two weeks, I primarily served the sexual needs of anyone who asked. There were a few other adventures along the way, of course. Aside from acting as a sexual outlet for the men, however, they didn't leave much of an impression on me. With the women, I was one of them; they treated me as an equal. Our time spent chatting, sunbathing, sharing languid caresses, and making love to one another was wonderful—that was where I found the most pleasure. A soft, tender, feminine atmosphere—it’s truly what I love. They playfully caught me off guard during a tanning session; they were all in bikinis, lounging languidly on mats in the sun, deep in girly conversation. There was no sign of arousal, but then suddenly Lisbeth came over and removed my bikini top and bottom, covering her mouth with her hand as she looked at me. "Hey, Lis, what is it?"

"Sorry, darling, just look at yourself!" (I looked down and saw tan lines on my chest revealing that I’d been wearing a woman's swimsuit—the lines were clearly visible!) "You look beautiful like that, stark naked with those tan lines!"

"Oops, I wanted to avoid that. Oh well."

As she caressed my chest, she said, "Wow, it looks like you’ve got little mounds forming and your nipples have gotten bigger! I love it!"

The caresses were sensual and deeply felt, sending waves of pleasure all the way to my lower belly (though still no erection). I let out soft moans. The effects of the injection were kicking in now, and I loved the sensations. Another woman moved over my head so I could suck her pussy and button, while Lisbeth dropped between my legs to pull out my little member and make it grow inside her mouth. Then, once I was fully hard, she came over me and sat on my cock, balls deep in her cunt and began riding up and down, while one of my hands slipped between her legs to caress her clit and the entrance of her pussy, which was filled with my cock. Several days later, I noticed that my curves were now clearly visible and the tan lines enhance the sight of feminine breasts ! More importantly, my areolas had widened and my nipples were protruding, causing constant arousal from the fabric of my outfits rubbing against them.

At a sex party, I found myself with two men: one was fucking me, while the other was deep-throating me. Then they made me lie on my back and took my holes again. And let me tell you, my throat really suffered. It was total impalement—balls slapping against my nose, gasping for air—especially when the guy’s hands slid under my neck to hold me with his cock balls deep into my throat. You want to serve the guys, sure, but afterwards, you realize you’ve been reduced to nothing but holes for these gentlemen to fuck. I could have been a doll; instead, they preferred to demean, debase, and subjugate a woman—or rather, a sex slave—to their power.

Another night, a waitress and I were strapped onto a counter; our legs—clad in high heels—were spread wide, and our bodies were hidden behind a curtain. The only things visible were two spread female asses and a pair of legs. Nothing above the waist could be seen. We were fucked all night long without seeing or knowing who was ramming us. It was truly the most degrading situation I’ve ever experienced. Just two objects side-by-side to be fucked! Some guys would even reach between my legs and feel up my little cock before impaling me.

Since I started this line of work, I’ve made quite a bit of money, which allows me to live well. I have a beautiful house, a car, a wife, and friends; I have plenty of free time and work in a dream environment!

My body has changed, too; without doing a thing, I now have 36B breasts, wide hips, a full, shapely ass, and a slim waist. My natural hair reaches down my back. In short, my body has adapted to my life as a woman, and my mind has followed suit. That is why I live full-time as a woman, even though I live with a girlfriend who is my lesbian lover and also the woman I regularly make love to. We enjoy a wide variety of lovemaking sessions—sometimes male-female, sometimes female-female—to our mutual delight.

My lifestyle has adapted, and my partner understands that when I am on a boat, I am away for work. I am away for about one or two weeks a month and am in high demand; the men who book these trips are often intrigued by the fact that I am a man who loves being a woman but can play either role upon request. I even have to turn down excessive requests from time to time. I’m used to this job now and get immense pleasure from it (and what pleasure it is!). Orgasms happen frequently and at any moment, but it is my job, and I do it to the best of my ability. I love my work; on the boats now, I no longer have to handle service or cleaning—I simply act as a "hostess," though I do help out with service occasionally. I am there solely to satisfy our guests' desires. Furthermore, there has never been any violence or unpleasant scenes; I willingly submit to wandering hands and playful slaps on my bottom. My body is at the service of all the guests for the duration of the cruise—it belongs to whoever needs it, according to their desires, and sometimes even to the crew—though measures are in place to ensure we aren't bothered by intoxicated individuals. Then, when I leave the boat, I happily return to my partner's arms for a completely normal life as a couple (both male-female and female-female).

My partner isn't jealous; she knows I love what I do and that it is necessary for us to live comfortably. She knows it isn’t cheating; it’s simply something I have to do. No romance develops during these physical encounters. Between us, however, the bond is truly one of love and respect. We have plans together—thinking about having a child, for instance—and a full, rich life. Our friends are mostly couples or groups of women with whom we chat and shop happily; to those around us, I am a woman. From time to time, I go back to being Bob and dress accordingly, though I have to bind my chest so it doesn’t show too much. We go out as a "real couple" to restaurants or shows; to the outside world, we are a female couple. Only one other couple knows our secret. The husband once caught me stepping off a yacht; I told him I was working as crew, but he remained skeptical. When we met up again—both couples together—we had to explain that I worked on yachts for cruises. One thing led to another, and we opened up to them; now they know who I really am. One day, while we were out as guests, he kept asking about my job; I initially just explained that hosts paid for our services. He burst out laughing, and in the end, I had to admit that I worked as an escort.

They wanted every detail, and eventually, he and his wife asked if we’d be up for a sex night involving both our couples. After consulting my wife—who isn’t used to sharing her body or mine with others—we agreed. She laughed and said to me:

- "Darling, I’m finally going to see you in action, but seeing you with another woman will be hard for me; I’ll probably get jealous. And I might not dare let another man caress me—or even take me—right in front of you! It’s so intimate!"

- "No, you’ll see, it’s mostly physical; you don’t feel like you’re betraying the other person since they know about it, see it, and are doing the same thing."

- "Yes, maybe; I trust you."

The evening started with drinks, then the two women and I (acting as a third woman!) quickly found ourselves in thongs and high heels in front of Jack; we pounced on him to strip him down to his briefs. In the bedroom, the three of us women got onto the bed, kissing and caressing each other, while Jack took out his cock and stroked himself. Soon we were all naked, kissing, caressing, and sucking on nipples and pussies, as well as my cock. At one point, I had to fuck Jack’s wife—who cried out loudly in pleasure—and then I sucked, caressed, and fucked my own wife; she gasped and then climaxed with a loud cry, all while twisting both my nipples, which made me explode. Jack then approached me:

- "I want to fuck you, you slut—just like you did with my wife!" He turned me around, slid his cock inside me, and fucked me hard until he came; his release was a huge relief for me, given how intensely he’d been going at it. Despite that minor issue, we have been seeing each other regularly ever since, sharing a great rapport. There have even been times when my wife has hosted Jack—or his wife—for an afternoon of sex; I tolerate this, provided I am informed beforehand. It serves as an outlet for her given the nature of my job, and I have no objections to it. Moreover, they have turned out to be a charming couple with whom we share a lot in common.

So yes, we lead a happy life.

I hope you enjoyed my story and took great pleasure in reading about my adventure.

Give me some feedback of your reads and your pleasure so I will be encouraged to write more.

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u/michelle_sissy100 — 24 days ago

FORCED FEMINIZED TO HAVE A VERY NICE JOB .( 4 /5)

4. What happened next.

The next morning, Caroll called me into her cabin. She wanted me—she wanted to make love to another woman and climax. Her husband was present but kept a low profile, leaving us to it. During our lovemaking, Caroll brought out the double-ended dildo again; she had me lie down and impaled me on it, then—facing me with our legs intertwined—she moved between my thighs to impale herself on the other end. Once we were fully connected, we began fucking each other’s asses until our genitals touched, then pulled back. We quickly felt the pleasure rising, gasping and moaning. Her husband watched us while caressing himself. When my hand went to stroke Caroll’s clitoris, she quickly arched her back; she finished by driving the double dildo deep into both of us while screaming, experiencing an intense orgasm that made her thighs tremble for a moment before she regained her composure. Her husband smiled:

"Well, you two naughty girls, you seem to be enjoying that! It’s a shame I can’t join in."

"(Caroll) Yes, darling, but it’s so different between women—so much more tender and deep; the pleasure is more intense."

"Yes, I see. By the way, Chloe, you seem to like taking a cock up the ass!"

"No, that’s never happened. It’s just an object, and it feels good."

"A real cock would surely be better!"

"I don’t know."

"Don't you want to give it a try? You’d be a complete woman then; you’d know everything they do and feel."

"But that’s not my thing, and there’s the pain factor."

"You didn't seem to suffer during your session with Caroll; you looked like you were having a great time and really enjoying it."

"Yes... maybe we could give it a try." "Come over if you want; I’ll get you ready and we’ll give it a try."

That’s how I let it happen. He laid me down on the bed with my ass at the edge and my legs in the air, and licked right inside my hole. Then he stood up and offered me his cock—slick with saliva—to suck, before positioning it between my thighs; he pressed his head against my asshole, grabbed my hips, and pulled gently to impale me. It went in fairly easily at first, then felt a bit tight and painful, but suddenly I gave way and he was able to slide all the way inside me—deep in my guts—with his balls slapping against my ass! I was completely impaled on a magnificent cock, feeling more and more like a woman. He started pounding me gently, then sped up, thrusting hard and fast. I was really getting into it, my belly filling once again with that wave of pleasure I’d already experienced with Caroll. Just as he arched his back, shouting, and drove his cock in to the hilt, I felt the spurts deep inside me, triggering a wave of pleasure that radiated through my lower belly.

That’s how, on that yacht, I became "the all-purpose slut—fucked from both ends, giving divine head to pussies and cocks, fucking women... a true submissive slut." I spent the rest of the week as a sex object for the ladies and gentlemen, as well as the skipper and my colleagues. When we returned to port, the couples gave me a massive "tip"—several times the value of my old wages—on top of my good salary for the trip.

I went back to my life as a carefree guy. Two weeks later, the skipper called to propose another two-week trip with five couples and four crew members (three men and one woman).

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u/michelle_sissy100 — 24 days ago

FORCED FEMINIZED TO HAVE A VERY NICE JOB .( 3/5)

3. My second day.

My first day had been packed with events I hadn’t expected to experience. I got plenty of rest and emerged at 10 a.m. Everyone laughed, and the four couples gathered there, congratulated me on my performance. Then Melany spoke up: "Bob, we’ve all been talking about you, and you can be proud of having satisfied everyone. We wanted to know if you’d be willing to spend the week as a girl ! You’re so feminine, gentle, and attentive—even when sucking a cock—that we could really picture you in a girl’s persona. Your behavior toward us would stay the same; only your look would change to that of a girl. Plus, your body is already hairless. For instance, when serving us, we picture you in a white lace-trimmed apron, a tiny thong underneath, a wig, a bit of makeup, and low-heeled sandals. You’d do the same things you did yesterday to please us, just in that outfit. Naturally, the men will ask you to take care of them—like you did with my husband yesterday—and they might ask for more, but it’s up to you to set your own limits. Of course, your tips will depend on the services you provide. Are you up for it?"

"Yes, in principle. But I don’t want to be forced to do anything more."

"Okay, so you’ll put on what I give you, and we’ll turn you into a sexy girl. What should we call you? Maybe Chloe?"

"That works for me."

We went to the pantry to find the aprons, then to Melany’s cabin, where I became Chloe for the week. When I saw myself in the mirror, I thought I looked beautiful and sexy—certainly not like a guy in drag! I loved it immediately: seeing myself as beautiful and desirable, and being accepted as such. But I suddenly realized that this wasn't at all what I’d wanted, even though I’d ​​suspected the "all-inclusive service" might involve something like this. Finding myself transformed—after just 24 hours—into a sexy waitress serving four couples made me panic. But I had agreed to do it, and there was no turning back! So, I stepped out and entered the lounge, where my arrival was greeted with applause. I was blushing furiously! There were plenty of comments:

- "What a pretty little waitress! Sexy and incredibly desirable! We’re going to have a great time."

- "Yes, it promises some good times and plenty of pleasure!"

- (One of the husbands) "And I hope we get to join in on the fun."

- (Melany’s husband) "I’ve had a promising start. What a super sexy, submissive waitress. Seeing her make love to Melany turned me on, and she took me straight to paradise."

As soon as I started serving drinks, wandering hands were all over me: my buttocks ("what a nice little ass you’ve got!"), my chest ("hmmm, such sensitive nipples!"), and under my apron—where my cock, tucked into my thong, remained small and hidden between my thighs, likely because I was feeling so feminine ("and such a nice, flat tummy!"). Then, two of the women quickly headed to the foredeck to sunbathe, while the other two—Caroll and Melany—lay down on a shaded mattress and began caressing and kissing each other. Spotting me walking by, Melany said:

- "Chloe, if you’re free, you can join us; we’re waiting for you."

- "I’ll just finish tidying up and be right there."

- "OK, the three of us can have some fun."

Shortly after, I lay down beside them—they were already deep in a passionate kiss—and they pulled me in between them. The three of us made out wildly, but the atmosphere soon turned more erotic and sensual. We all had our breasts caressed, sucked, and pinched, and our pussies licked and sucked, sending the heat rising. We even explored each other’s anuses with fingers wet from saliva or juices. I loved it; at one point, while I was on all fours between Melany’s thighs licking her pussy, I felt Caroll licking my anus, her tongue even slipping inside a little. It felt amazing—"Mmm... oh yes!"—and then I felt something pushing and gently entering me. Caroll was sliding a dildo deep inside me; it felt strange, yet not painful—actually, it was pleasurable. She moved the toy gently back and forth, making me shiver! Then, for a moment, nothing; I felt her move behind me, teasing the toy while moaning softly. She impaled herself on the other end of the double dildo she’d put in my ass, and we moved in rhythm, both our asses filled by that object of pleasure. I felt pleasure rising—a different kind of pleasure, deep in my gut and belly—filling me up more and more from the inside! The way her buttocks repeatedly bumped against mine felt divine. Then we changed positions; my cock came out and was massaged, licked, and sucked until I was rock hard. I took turns fucking both of them while the other exchanged caresses and kisses with her partner, watching us all the while. I ended up bringing both of them to orgasm without cumming myself. The two of them then took turns working on me, bringing me to the brink of climax before squeezing my cock to let the tension subside and starting all over again. It became harder and harder to hold back; eventually, seeing I couldn't last much longer, Caroll straddled me and impaled herself onto my cock in one swift motion while Melany pinched my nipples hard. I let out a piercing, high-pitched scream—the kind only a woman can make—as I felt my juices spurt deep inside Caroll, and I nearly passed out from the sheer pleasure. I was completely spent! I lay there for a good half-hour afterwards. For the rest of the afternoon, I did nothing but wait on everyone; I was groped, spanked, and had my nipples pinched by everyone—especially the men—amidst a barrage of lewd comments. To them, I was nothing more than a girl at their beck and call, a sexual object for their amusement. But that suited me just fine.

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u/michelle_sissy100 — 25 days ago
▲ 63 r/SissyRewired+1 crossposts

FORCED FEMINIZED TO HAVE A VERY NICE JOB .( 2/5)

2. My first day on the job.

This afternoon, Caroll and Lisbeth wanted drinks, which I brought to them in the living room.

- "(Caroll) Come on, sweetie, get comfortable!"

- "(Lisbeth) Oh yes, show us your chest." (I took off my T-shirt, and they removed their beach dresses, leaving them naked.)

- "(C) Do as we did—take it all off." (I took off my shorts.) "Oh yeah, you’re rock hard, you dirty dog! Do we turn you on that much?"

- "(Me) I can't hide anything from you!"

- "(Lisbeth) Get under the table and take care of us; It is said that you give amazing head. We can't wait to enjoy your talents!"

I did as told, sucking on one pussy while caressing the other with my hand. I could hear them sighing and making comments, but I happily kept at my work. Their pussies were dripping wet and hot when Caroll said, "We can't take it anymore! You’ve got us burning up! Now you have to finish the job! Take me—quick!"

I stood up and laid Caroll down on the bench seat while she kissed me deeply and hungrily! Then I got on top of her and impaled her with my cock—"Ahahahahahaaaaaahhhh... hmmm... yes, that feels good, go for it!"—and I started pounding her. Lisbeth moved in behind me; our mouths locked together, and she caressed my chest while pinching my nipples, making me even harder and causing me to pant as I pounded Caroll, who was moaning louder and louder. Then she exploded into a massive orgasm, collapsing onto the bench seat, completely breathless. I gently pull away from her and feel Lisbeth turning me back towards her; she moves down and takes my cock—which is desperate for release—into her mouth. I lift her up to impale her in turn, massaging her breasts as her nipples harden with pleasure. After a few thrusts, she stops me: "No, stop—I want to drink your juice! Give it to me!"

She bends down and takes my cock deep into her throat; her suction quickly makes me explode, shouting as I empty myself, while she greedily swallows it all! "Mmm! You’re a real gem! Cindy is right about you—you have such a gentle, attentive, and feminine way ! Show me your skills as a cocksucker! Make me cum!" I press my mouth against her pussy lips and caress her clitoris—which is standing out prominently because she’s so aroused—with my tongue. It doesn't take long for me to bring her to a peak and make her explode; she arches her back and cries out as she orgasms. Our caresses continue all over; in particular, we focus on wetting the rims of our anuses, caressing them and even slipping fingers inside. It’s all done so tenderly and gently that I don't mind it at all—in fact, I enjoy it. (My only prior experience in this area was with a female lover; we’d discovered together that having that hole caressed and penetrated felt good, though we never took it any further.)

Later that evening, Melany’s husband comes to see me: "Melany is often with women. Apparently, the girls really enjoyed your performance this morning. Come see us in the cabin; I want to watch you two fooling around—it turns me on." I can’t help but agree, though I’m terrified. Once we arrived, the three of us quickly stripped naked; standing up, I caressed Melany’s breasts, her lower belly, and her already-soaking pussy, while she stroked my chest and face before reaching down to grab my rock-hard cock. Our mouths were locked and our tongues busy, while her husband sat in the corner masturbating. We moved to the bed; I positioned myself to lick her pussy, and I could feel her pulling her legs toward her. We quickly settled into a 69 position—me working her pussy and clit with my tongue, and her with her mouth full of my cock. For a good while, she moaned and I began to pant. She said, "I want you inside me. Come on! I want it so bad!" I turned around and thrust my cock all the way in—burying it deep inside her—as she cried out, "Aaaahhhh... oh... ahaha... that feels so good!" Then, as I pounded away, I quickly thrust deep into her, arched my back, and shouted out my orgasm, which triggered hers. We collapsed onto the bed side-by-side, and our mouths met again tenderly. After a moment of rest, her husband said to me, "Well done, Bob—you were great with my wife. Now, can you make me cum?"

"No, that’s not my thing, but maybe I could stroke you?"

"Okay, but it won't be as good. Oh well... come here."

I moved closer to him and, kneeling down, took his beautiful cock in my hand and started stroking it, making him begin to writhe. After a moment, acting on instinct, I took his cock into my mouth to suck it, moving back and forth gently; this made him groan louder and sway his hips. Then, suddenly, I remembered how I reacted when my own nipples were pinched, so I reached out and pinched his. At that moment, he arched his back, thrusting his cock deep into my throat, let out a loud shout, and shot his load right down my gullet: "Whoa... Fuck, you really know what you're doing!" I swallowed it all without a second thought. Once he’d calmed down and was resting, he gave my ass a smack and said: "Yeah, you’re a real slut! You really know how to satisfy a man! And you even relish my cum! A real whore! You’d be right at home as a waitress—at least then we could fill your belly, too!"

See soon next part.

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u/michelle_sissy100 — 25 days ago
▲ 106 r/SissyRewired+2 crossposts

FORCED FEMINIZED TO HAVE A VERY NICE JOB .( 1/5)

1. My beginnings.

I was a reserved, slender young man—not very tall, but apparently charming. After finishing my studies, I took on odd jobs to get by, but I couldn't find steady, well-paid work. I didn't go out much due to a lack of funds, though I had met a group of friends and a few girls I enjoyed talking to.

One day, John—a friend from the group—told me I could land an interesting job, provided I was willing to accept certain conditions. He sent me to see his boss, who described the role : working as a waiter on yachts. It meant heading out to sea for a week or two (or even longer) to assist the skipper with maneuvers and cleaning, serve the guests, and cater to their specific requests. Anything was possible—including intimate moments with the clients. The pay was excellent while at sea, with substantial tips based on the service done. He suggested I give it a try for a week to see how I liked it.

So, a few days later, I showed up at the gangplank of a beautiful boat and was welcomed by the crew : the skipper and three guys in swim trunks. From the start, the contrast was striking : clients in shirts and trousers, women in tiny bikinis, and us in shorts and T-shirts bearing the boat’s logo. Once we hit open water, the "open bar" began, meaning we served drinks without limit. While bringing drinks to the women, I overheard comments like : "Oh, what a handsome young thing. With that androgynous look, he’s irresistible—I’d love to have him!" Naturally, there was some brushing up against me while I served, and a few wandering hands. Before long, the ladies were sunbathing topless—and soon after, completely naked! While I was working, one of them said, "Looks like our young waiter is enjoying the view! He’s got a massive hard-on!"

"Oh really? Hmm, come over here so we can see!"

"I can't, I'm on duty..."

"Yes, you're at *our* service, so come here."

Not knowing what to do, I walked over, and hands started running over my shorts, making me blush. From behind a table, I saw a coworker signal that it was okay—that I should go for it. I let myself go, and one of the women pulled down my shorts, to the delight and laughter of the others. Cindy, the one closest to me, turned, placed her hand on my cock, and—smiling into my eyes—pressed her lips against it before taking it deep into her throat. I was in heaven, though very flustered, when she said, "Come on, let's go to my cabin." Once we were alone, she kissed me deeply and caressed me all over. I started fondling her breasts and licking her pussy, making her moan. Suddenly, she said, "Darling, take me—I need it so bad!" I stood up, stepped between her wide-open thighs facing her dripping sex, and thrust my cock all the way in with one swift motion. "Aaahhhh, yesss! That feels so good!" As I started pounding her, she panted, her head tossing from side to side as her moans grew louder, until she climaxed magnificently, writhing with pleasure. After a break, I went back to my waiter duties, but she said, "Well, for a beginner, you really know what you're doing. And you're so tender, so attentive, so gentle with your touch—when you were licking me, I thought a woman was doing it!" I think we’ll see each other again soon.

- At your service, Madam.

- No, sweetie, I’m Cindy! Anyway, see you next time."

Next chapter soon. Be patient and tell me if you like, if you want to know what happenned.

Good reads.

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u/michelle_sissy100 — 26 days ago
▲ 93 r/SissyRewired+2 crossposts

How my wife pushed me to become a sissy. (4/4)

4. I become a real feminized sissy.

We went back to our normal lives after that day, and nothing had changed—except that Cathy pampered me even more. Some time later, she asked if she could see Arthur again, and I agreed. A second afternoon—just as hot and successful as the first—took place, leading to Arthur coming over once a month. On one hand, I was happy to please her, but I was also jealous of sharing her—even though I was participating as a fully feminized Michelle, with no erection or desire other than to be caressed and fucked like a real female. I envied Cathy’s position; my dream was to be in her shoes, with a guy taking care of me and his beautiful cock filling me up. But I’m thinking like a madman! Is it possible to have thoughts like that when I’m Michelle?

One day, I finally talked to Cathy about it:

"You know, darling, every time you’re with Arthur, I get really jealous having to share you."

"Oh, honey, it’s just an erotic game, and I’m only interested in how it differs from what we do. I don’t love him; I just want to be fucked differently than the way we do it."

"Are you sure you don’t have a crush on him? No feelings involved?"

"Oh, yes. I feel safe in his arms, but it’s just about his caresses and having his cock inside me. Plus, there’s no risk of leaving any traces since we use protection."

"The thing is, you know that as Michelle, my cock is tiny and tucked away in my thong. But I also have purely feminine thoughts, and it’s unsettling."

"It’s natural for your mind to follow suit when you transform into a woman."

"Yes, maybe, but now it’s becoming a worrying obsession."

"What is, darling?"

"When I see you two in the act, I imagine myself in your place—being caressed, kissed, and fucked as a woman!" "That’s ridiculous!"

"Not really, darling. You dress like a woman, you try to assert yourself as a woman—and by extension, adopt the role of a temptress to find a man who’s attracted to you, who’ll woo you, and then turn you into a woman by fucking you."

"Can you believe it? Me—your partner—actually wanting to get fucked! I never would have imagined it. Does the mere act of dressing like a woman make me *become* a woman—act like one, and above all, *think* like one? It’s impossible; I’m losing my mind!"

"No, darling, you’re just embracing who you are. If you want to stop obsessing over this, I think you need to act on those thoughts—find a man who can break through that macho mindset of yours."

"Oh boy! What have I gotten myself into since the day I agreed to wear a thong just to please you? The further we go, the more I turn into a female in heat!"

"Exactly. Your feminine side wants to come out and be embraced. Will you do it?"

"Would you be okay with me getting fucked by a guy? Isn't taking my strap-on enough for you?"

"You’re the one picturing a guy’s cock inside you! And yes—under the same conditions where you see me giving myself to Arthur: no feelings, nothing but physical desire."

"Do you think I should go through with it? Would you be okay with that?"

"Of course, darling. You’re okay with me seeing Arthur, so why would I say no? Besides, you need this; taking my dildo isn't enough anymore. You need a real cock to step into the role you want: being a complete woman. Afterward, you can see if you like it or not—whether you’d do it again."

Naturally, that conversation sealed my fate. I really ought to get a real cock—not just Cathy’s dildo—to satisfy my fantasies!

One day, when she calls Arthur to arrange a meeting, she tells me she’s mentioned me to him. He finds me a turn-on, and depending on what we decide, he’s ready to either take me himself or introduce me to one of his friends. I’m no longer in control of the situation. Knowing I really want to fulfill my fantasy, I agree. Cathy suggests Arthur, and I say yes to that, too.

In preparation for his visit, Cathy uses her dildo on me the day before to get me ready. She spends the whole morning getting me dolled up so I look my best: thong, bra, short flared dress, medium-length curly wig, high heels (4 inches), makeup, and jewelry. When I finally see myself in the mirror, I really like what I see. I feel very attractive and plan to act like a tease.

When he arrives, he kisses Cathy on the lips—his hand wandering over her buttocks—before coming over to me.

"You’re very attractive; I think we’re going to have a great time. Are you ready?"

"I don’t know... I hope so. In any case, I really want this."

"That’s a good start. You’ll see—I’ll be very gentle for your first time."

He steps closer, slides his hands around my back, and pulls me in to press his lips against mine; our tongues meet. His hands move over my buttocks, and one of them finds my nipples. He turns me around so my back is to him, removes my dress and bra, then caresses and pinches my nipples, making me moan in my high-pitched little voice.

I reach behind and feel his cock through his trousers; I undo them, let them drop to the floor, and grab his cock. Once he’s turned around, I drop to my knees and take his cock into my mouth—my first time ever doing this—licking and sucking it. He seems to enjoy it while fondling my nipples, which makes me melt. "Stop if you want, or else I’m going to explode in your mouth. Come over to the bed and get on all fours instead." Once I’m in position—arched, ass in the air, legs spread—I feel his mouth caressing my hole, oiling it up, and slipping slightly inside me. God, it feels so good! I feel great, so relaxed! First one finger, then two.

- "Are you ready now?"

- "Oh yes, I feel great and I want to feel you inside me!"

How could I say something like that to a man? I’m losing my mind, but I want it! I feel his cock touch my hole, then push and slide in quite easily—past the entrance and deeper. It doesn’t hurt; it feels strange, but in a good way. Suddenly, I feel his balls touch my anus, confirming he’s deep inside me! I was getting fucked, and I loved it! As he thrust back and forth and picked up the pace, I started letting out little high-pitched moans with every stroke. A wave of pleasure washed over my lower belly, radiating through my stomach, my lower back, and then my whole body. I was in heaven! I lost track of where I was, but I felt amazing! Arthur gave my ass a few light slaps, which made me react and sent the tension soaring. He then slammed his lower belly hard against my buttocks with every thrust, sending a jolt of electricity through my stomach each time. Oh! It felt amazing! I was writhing, and then suddenly, a violent thrust sent me spiraling into an intense wave of pleasure—a female-style orgasm, since nothing happened down below with my little "worm," which didn't even ejaculate—just as I felt his load filling me deep inside and heard Arthur cry out in his own climax! We lay side by side on the bed to catch our breath, and our lips met in a long, tender, sensual kiss.

Once we were alone with Cathy—who had watched my deflowering with pleasure while caressing herself—she said:

"So, my dear Michelle, you seemed to enjoy losing control under Arthur’s cock!"

"Oh yes, I was in seventh heaven. It felt so good I thought I was going to faint!"

"Well, you slut! You’re a real female dog in heat! Ready to go again?"

"Whoa! Not so fast! First of all, I’m not a woman—let alone a slut—and as for what comes next, we’ll see if I’m still in the mood."

"In any case, you acted like a woman—and a pretty teasing, slutty one at that—sucking his cock and positioning yourself to offer him your body!"

"Well, I didn't really know what I was doing."

"Oh, but you knew instinctively! You did everything to make him fuck you hard. You’re a full-fledged woman now—fucked in the mouth and the ass, and filled with cum!"

The next time, only Cathy got fucked by Arthur. Then he offered to introduce her to one of his friends—a confirmed bachelor just like him—if I was interested. A date with the two guys was scheduled, and I see John often now, but the four of us meet up once a month; Arthur and John take turns fucking both of us, and our visits last the whole weekend.

In my everyday life, I still present as a man. At home, Cathy and I make love in every way imaginable: beyond caresses and kisses, she sucks my cock and takes it in her pussy and ass (and that’s reserved just for me!), and she also fucks my mouth and ass when I’m Michelle. As for me, I fuck her throat, pussy, and ass (and she loves it). Michelle and Cathy meet up with their two lovers once a month. We get thoroughly serviced over the course of two days, leaving us exhausted but sated with pleasure. I’ve even started referring to myself in the feminine! We also go out quite a bit—either as a mixed couple or as a female couple (and we have a blast attracting guys!). Sometimes the four of us go out together—two couples—and I love being a woman in public. A couple of very close friends discovered by chance that I cross-dress, and they’ve welcomed us as a lesbian couple without any issue.
I lead a full "sissy" life, and I feel truly comfortable in my own skin being able to switch between male and female behavior whenever we feel like it. The very special thing I felt during this journey is that I wander why when I am a man I am active and sure of my power, and as soon as I dress in my feminine way, I am weak, not sure of all, a little submissive and ready to obey, even often ready to cry for nothing. I know it is a normal way to behave for girls, but I never imagine I can be the same only by changing my clothes, that changes my mind and my behaviour !

I hope others are lucky enough to experience this too.

Tell me if you loved the story, it is always a pleasure to know it.

Good read and good vibes ! Kisses all of you .

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u/michelle_sissy100 — 1 month ago
▲ 9 r/SissyRewired+1 crossposts

How my wife pushed me to become a sissy. (3/4)

3.Cathy goes on with a friend.

Don’t get me wrong—I usually live as a man in public, but I go out with Cathy dressed as a woman whenever we feel like having some fun.

One day, while we were talking about the future, Cathy said to me:

"Darling, I have a fantasy, but I don’t know if I can make it happen. I’ve been thinking for a while that I’d like you to be dressed as a woman, and for a stranger or a friend to come over, seduce me right in front of you—caressing me and all that—and then make love to me while you watch. What do you think?"

"I don’t want you cheating on me!"

"That’s not what appeals to me; it’s doing it while looking at you, and having you watch me enjoy myself in his arms."

"Do you want us to break up?"

"No, darling, I’m so happy with you; I just want to try making you jealous and see you watching my lovemaking."

"You dirty girl! And you think you can pull that off without any risk?"

"We just have to be on the same page about it."

After thinking it over for days, I finally agreed to give it a try. Overjoyed, Cathy looked for a partner she liked—someone who wasn't looking for a live-in relationship. One day, she told me she’d finally found a potential partner named Arthur, and that he’d be coming over for a drink one evening. When he arrived, I was quite surprised to see a handsome man in his thirties. He made a good impression on me, and I figured Cathy would likely be treated well by him. It was agreed that he would come over on Saturday afternoon, but that he didn't want to see me. When I told him Cathy wanted me to be present—but dressed as a woman—he hesitated a bit, then said: "Okay, you can be there as a woman, but you can't get involved at any point." So, on Saturday morning, I get ready; Cathy helps me feminize my look and lays out my outfit—a white lace bra and thong, matching garter belt, white stockings, 3-inch heels, a flared mid-thigh dress with a plunging neckline, and an ash-blonde, shoulder-length wavy wig. She helps me with my makeup—which I haven't quite mastered yet—and adds hoop earrings, a necklace, rings, and bracelets. I finish up by painting my fingernails and toenails. I’m delighted with the result and proud to look so desirable (I’ve noticed during our girls' nights out that men aren't indifferent to looking at me, or even brushing up against me). Cathy has simply put on a short, flared dress with nothing but a thong underneath, and 4-inch heels. She looks incredibly desirable, and it stings a little to know she’s showing herself off like that—but not for me! Am I really sure I won't lose her to Arthur?

When he arrives, I fix them drinks, only to find them on the sofa, kissing passionately! Oh, how I hate them! He’s taking my partner away, and there’s nothing I can do about it! Arthur’s hands are all over Cathy’s body and dress; he’s fondling her breasts and pinching her nipples, while his hand slips under her dress to spread her legs and work her intimate areas—all while she has unbuttoned his shirt and is running her hands over his chest. Their mouths are locked together, and I can see their tongues darting between them. A few sighs, followed by heavy panting, signal the rising tension. At that moment, Cathy stands up and smiles at me, slips off her dress, and kneels before him, spreading her legs; she undoes his trousers and lets them drop to the floor, then takes his already fully erect cock in her hands and begins to stroke it. Soon, her mouth closes over his cock—sucking and swallowing it—and she starts moving up and down. He begins to moan: "Ohhhhhh... aaaaahhhh... hummmm." Then he leans forward, cupping Cathy’s breasts in his hands to tease them, and says, "Come here—I want you!"

Cathy stands up and leads him to our bed; I follow and sit in the corner so I can get a good view. He lays Cathy on her back and lowers his mouth to her sex, licking her clitoris to ramp up the tension. She is panting rapidly; he rises, places his hands on her hips, and pulls her toward him until her buttocks are at the edge of the bed. He steps between her legs, positions his fully erect cock against her pussy, and pushes slowly. I watch his cock gently slide into Cathy’s sex; she lets out a low, continuous moan as he slowly buries it deep inside her. They lock eyes for a moment, then he begins to possess her, thrusting gently at first, then with increasing speed. She tosses her head from side to side, her eyes rolling back as her pleasure mounts. "Huuuummmm... ohhhh yessss, that feels so good! Fill me up!"

To them, I’m not even there, but it’s tearing me apart to see her with a man who is making love to her so beautifully—and who is going to make her come!

Arthur picked up the pace, and I could feel Cathy writhing and panting ever more heavily. Then she began to moan incessantly, on the verge of climax; sensing she was ready, Arthur delivered two powerful thrusts and held himself deep inside her, arching his back and shouting out his pleasure, which sent Cathy into a violent orgasm. After a brief rest, he went to the bathroom and returned to approach Cathy:

"My dear Cathy, making love to you was an incredible pleasure. You really are a great partner for sexual play; you give it your all. Thank you for a lovely afternoon. And as for your female friend—she played her part well and was very discreet. I appreciated that."

"You know, Arthur, you were wonderful. I never imagined I could experience such pleasure in your arms. And Michelle—thank you for introducing me to Arthur and for your discretion while we were making love. I truly love you; you always make me so happy."

Arthur stepped closer, claimed her lips in a deep kiss, then got dressed and left.

last part tomorrow. Good reads all

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u/michelle_sissy100 — 1 month ago
▲ 6 r/SissyRewired+1 crossposts

How my wife pushed me to become a sissy. (2/4)

2.Our life goes on with other new ways of pleasure.

Now I know that my tits, my cock, and my hole are sources of pleasure; Cathy has super-sensitive breasts, and her three fuckable holes—her mouth and throat, her pussy, and her ass—give her amazing orgasms, even several in a row.

But Cathy didn’t stop there. One day, she came back wearing a strap-on and said:

"Right, now that you’ve completely taken possession of my body, I want to do the same. I want you all to myself. Get on all fours at the edge of the bed; I’m going to really fuck you to see what it’s like to have a cock and take possession of someone else—to enslave them to your cock!"

"Yeah, but take it easy."

"Don't count on it; I’m going to fuck you just like you do when you use me and ride me at a frenzied pace."

"Please, Cathy, be gentler."

"Just like you, darling—when I’m impaled on your cock and your pleasure builds as you speed up to fill me. You’re going to see what it feels like."

Once I’m in position, I feel the cock against my asshole, then sliding inside me—painful because of the dildo's size.

"You’re hurting me, stop!"

"No, you’ll see—the pain will fade, and you’re going to love it."

"Ouch!"

"There, there, fragile little girl! My cock is buried deep in your guts now. Time to really pound you!"

I feel her hands on my hips, pulling and pushing to impale me on her cock and pull me back, keeping a steady rhythm. Sure enough, the pain almost vanishes, giving way to pleasurable sensations. I hear Cathy panting behind me as the thrusts grow more violent; then suddenly, she drives it all the way in and climaxes in a magnificent orgasm! It was true that she was going to fuck me hard.

- "You see, Mike? You’re confirming your status as a fuckable girl! All you’re missing is a real cock emptying itself deep inside your ass. When you’re dressed in female lingerie, I think you should go by the name Michelle."

- "I’m okay with the name, but there’s no way I’m becoming a 'fuckable girl'! I’m your guy; I’m fine with you playing around with me—even cross-dressing—but no man is ever going to do to me what you just did!"

- "Fair enough. But you mentioned cross-dressing... you’re right, I’d love to see you in women’s underwear—or even more, since you brought it up."

- "No, that’s not what I meant."

- "Maybe not, but you gave me a great idea—just to see you in a different light."

A while later, right in the middle of things, she asked me to put something on and handed me a bag. Inside were black lace panties and a matching bra. I smiled, but seeing her serious expression, I got up and did as she asked. I turned around in front of her to show myself off.

- "You look amazing! It suits you perfectly! And look between your legs—you’ve got a tiny cock hidden in those panties, barely visible. Your body is embracing this feminization and getting into the mood." (She steps in front of me and cups my breasts, pulling the skin to fill out the cups a bit.) "And look in the mirror—you’ve even got a small bust!"

I do indeed see a fairly feminine body, which surprises me. She hands me her 2.5-inch mules and places a medium-length wig on my head, adjusting it. Stepping back, she says:

- "Now you look really cute! Stay right there—I’m dying to fuck you!"

I stand there looking a bit sheepish, yet proud that I can pull off the look of a girl. She comes back with her strap-on and the dildo (there is also an internal dildo that she takes inside her, fucking her at the same time she uses it on me, which makes her climax). Down on all fours, I get thoroughly taken, and she has a wonderful orgasm. As for me, I’m overcome by spasms and let out little high-pitched cries with every thrust—thrusts that feel nothing like a man’s! How could I be doing this? Is my body adapting to my clothes? But I realize that when I’m dressed in women’s clothing, in my mind I *am* a woman; I think like a woman and I want to be fucked!

These games have continued, and now I sometimes dress fully as a woman—with a wardrobe that’s becoming quite extensive—and apply makeup, which allows us to go out "as women" whenever we feel like it.

Soon next part. Good reads, and don't deny giving me a feedback if you like the story.

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u/michelle_sissy100 — 1 month ago
▲ 179 r/cdstoriesgonewild+1 crossposts

How my wife pushed me to become a sissy. (1/4)

I’m Mike, a man living an ordinary life; after various adventures, I married Cathy. We shared a perfectly normal life as deeply in love partners, which included a spicy sex life where we experimented quite a bit to discover our desires and the best ways to caress, kiss, and give each other the most intense sensations and orgasms possible. During these moments, our caresses awakened various sensations—particularly on Cathy’s breasts and on my own anus, which had become sensitive.

As for her breasts, I often caressed them and loved teasing her nipples; she enjoyed it too, almost reaching orgasm just from my touch—caresses, gentle pinches, and sucking. A little extra stimulation on her clitoris or the feeling of my cock sliding inside her was enough to tip her over the edge into a deep orgasm.

Regarding my ass, I felt pleasant sensations when she ran her finger around the rim and then pressed slightly against the opening. It had become a little game for her, though she refused to let me do the same to her. Gradually, her game evolved into pressing against the ring of muscle, which felt good. Then she had the idea of ​​wetting her finger; this made it easy for her to start opening me up and inserting the tip of her finger, moving it back and forth. At that point, the sensations became much more intense and pleasurable. One day, she said to me:

- "Honey, would you be okay with me inserting my finger all the way?"

- "Hmm, I don't know... could it hurt?"

- "I'm not sure, but if I try, you can just tell me to stop if it starts to hurt."

- "Yes, of course—but I suppose I need to be relaxed, so lying on my stomach and staying calm."

- "That’s probably the least painful way to do it, if you do feel any discomfort." "Alright, I’m willing to let you try, but take it easy."

Once I was lying on my stomach with my legs spread wide, I felt her well-salivated finger circling "the spot" while applying light pressure. As she pushed a little harder, she would gather more saliva from her lips, keeping me well-lubricated for the next step. Then, I felt the first joint of her finger slide in gently, without pain. When she reinserted her wet finger, I felt her push a bit further; suddenly, the finger slipped all the way in easily, having passed through a sort of "closed door" that opened the way. When she moved her finger back and forth, there was no resistance and only a hint of discomfort. She began moving in and out of me just as I do with her pussy, which gave me little waves of pleasure. After a while, she inserted two fingers—sliding easily into my saliva-drenched hole—and the sensation was incredible. Then we made love like never before, aroused by our new discoveries.

Since her own breasts were so sensitive, she wondered if I might feel the same things; she often caressed my nipples and teased the tips, though I didn't feel much at first. However, as she kept playing with them, I began to feel a mild, not unpleasant tingling sensation. Cathy persisted, and gradually, the feeling spread across my entire nipple; as she continued, that sensation slowly washed over my whole body.

She asked if I’d mind her removing the sparse hair growing on my chest, as she didn't care for it much—it bothered her to have the hairs in her mouth, especially when she was sucking on my nipples. So, she got into the habit of waxing my entire chest every now and then.

One day, while I was really enjoying her caresses—her mouth sucking one of my nipples while her hand stimulated the other—I found myself squirming with pleasure. Suddenly, I let out a moan, but in a high-pitched little voice I didn’t recognize—like a woman right before climax! Cathy laughed and said:

"Well, well, you little slut! You seem to really like it when I caress your tits!"

"Oh yes, darling! It feels so good!"

"I can see that! But are you going to go all the way?"

She clenched her teeth around my nipple, while her hand pinched and twisted the other one.

"Ouch! That hurts! Stop!"

At that exact moment, feeling my cock rock-hard, I arched my back and shot my load all over my belly, crying out, "Aaaahhhh! Ooh-ooh-ooh!" As I collapsed back onto the bed, Cathy was in stitches: "Just like I said—you’ve turned into a real slut! You cum like a chick! Just from having your tits played with!"

"No, darling, don't say that! You know I'm not a girl!"

"You just proved otherwise! You dirty little pig!"

Little by little, our experiments went further. As for my hole, I loved it when she worked on it—and she certainly didn't hold back! By now, I could take three fingers with ease, and the pleasure was always intense—until the day she came up with a devilish idea! Without warning, she slid her vibrating dildo inside me and turned it on deep within. What a sensation, being completely taken over by something beyond my control! We kept caressing each other, but my belly was churning with the mounting pleasure! She moved down to my stomach and took my rock-hard cock into her mouth, sucking it vigorously! The effect was immediate: the vibrations sent the heat soaring, and I was struggling to stay conscious. Having my cock sucked deep into Cathy’s throat topped it all off; I was utterly unable to react, my mind consumed by the rising pleasure, until suddenly I felt myself explode—my body arching, letting out high-pitched, feminine cries I couldn't suppress, while feeling my cock deep in Cathy’s throat as she swallowed every drop of my cum with genuine delight. Once I’d come down and calmed a bit, Cathy asked:

"So, Mike, how was it?"

"Divine, darling! You’re a real sex goddess!"

"And you—a real slut in heat!"

"Oh no, not that—it was so good, the best orgasm I’ve ever had!"

"Yes, but an orgasm from getting your hole fucked like a female—a real dirty slut. You’d be ready to get taken by a guy!"

"Absolutely not!"

"Well, you know, your nipples stay hard now whenever I play with them, your breasts are sensitive just like mine, your chest is smooth, and your ass takes a dildo with no problem—and with such amazing results!" "Besides, your cries of pleasure speak volumes: they are the cries of a female climaxing, not the grunts of a male."

A while later, she put her vibrating dildo inside me again—but without sucking me off. As the heat rose, she positioned herself facing me, kissed me, and—just as I started writhing—grabbed both my nipples and twisted them; it hurt, but it also triggered a massive jolt of pleasure that made me explode, just like the first time.

"You see, Mike? You’re turning into a real female; you get off on being fucked, just like us women! One day, we’ll have to find you a real male—a stud—to fuck you and make you feel like a true woman, to let you experience what a good cock does to us."

"No, you’re dreaming there, darling; I’d never do that!"

"We’ll see."

Some time later, Cathy asked if she, too, could find pleasure using her other hole. When I agreed, she asked me to do for her what had been done for me: try to prep her and see how it went. I followed the same process she had used to train me to receive caresses—and more—in my own hole. After a long, tender warm-up, she had no trouble accepting first one finger, then several, and experiencing intense sensations. After a great deal of preparation and contemplation, she eventually took three fingers inside her; they fucked her and brought her to the brink of an orgasm, which was then triggered by caresses on her breasts or clitoris. The day I went down on her while working her ass with three fingers, she had a spectacular orgasm. Eventually, she agreed to let me deflower that hole. Once she was aroused, I moved in behind her with my hard, slick cock, pressed the tip against her hole, and pushed gently while pulling on her hips with both hands to ease myself inside. Once the opening gave way, I felt some resistance and paused; then I gave a little push, and I slid right in. I waited a moment, moving slowly in and out to go a bit deeper, and stopped when my balls touched her pussy.

- "So, darling, how does it feel?"
- "Good. I love it when you hold my hips; I feel fuller than when you fuck me. How deep are you?"
- "I’m inside you, darling—my balls are touching your pussy; I’m all the way in."
- "Incredible! I thought you’d just entered."
- "No, I’m deep inside your guts now! I own you completely."
- "You’re such a bastard!"
- "No, but now I’m really going to fuck you hard and fill you up."
- "Oh, you bastard—yes, go ahead, fill me up! I’m dying for it!"
I pounded her ass harder and harder, and the intensity of that first time meant I didn’t last long. The orgasm came on fast and hard—I let out a roar (a manly one!) as I filled Cathy’s belly; she was panting with pleasure (though she didn’t manage to climax that day).

Next part tomorrow. Good reads. Have pleasure.

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u/michelle_sissy100 — 1 month ago
▲ 24 r/SissyRewired+1 crossposts

How my childhood friend has changed: he's now a sexy woman! Part 6/6 and END

6. I become Lilly's guinea pig.

Lilly, being a surgeon, really loves to experiment. One day she told me she wondered if a man who had become a woman, like me, could produce milk. I figured the treatment for pregnant women to increase milk production should stimulate the mammary glands, and breast-milking sessions should be able to induce lactation.

"Would you be okay with me trying it on you?"

"And what would it do for me?"

"Probably make your breasts swell a little, and the pumping is quite pleasant, and if it works, we stop and everything goes back to normal."

"Okay, if that's all it is, let's try it."

She gave me a special diet, a few injections of medication, but nothing particularly noticeable. Then she brought a machine with two "funnels" and a pump. She had me sit comfortably in a chair, then placed the cups on my breasts and turned it on. My breasts, being suctioned, filled the machine's chambers, and it began to suction one side, release, then suction the other, and so on. It was strange but not painful. Lilly "pumped" me morning and evening. Little by little, I felt my breasts getting heavier, and Lilly was delighted but wanted more. After two months of pumping, I was getting a bit fed up and wanted to stop, but the persuasive Lilly asked me to stick it out a little longer. To keep me from complaining so much, she started inserting a vibrating egg or dildo into my vagina during the pumping, which raised the temperature and brought me to orgasm each pumping session. The longer I resisted before orgasm, the stronger it was. I resigned myself to pumping with orgasm. After three months of this treatment, one day, a radiant Lilly, as she released me, showed me the small container on the pump. "Look, Vic, you have milk!" she said. Indeed, there was a little whitish liquid. Soon after, I could see the milk flowing from my breasts with each pump, and the container filled up. Lilly took it to the hospital, which needed breast milk. It was tiring, but the orgasm was my reward. On the other hand, I had to buy new bras because my 36C had turned into a 38D—real breasts that were on display, and I was proud of them. Lactation made them very sensitive to caresses, and Lilly didn't hesitate to use them, even drinking my milk directly. Being breastfed by someone (a baby or another person) is a wonderful experience. The two bodies become one, and feeling the milk flow from the breast and into the mouth while caressing the other person's face and hair creates unforgettable sensations and a feeling of completeness, of the bliss of nourishing someone. No other experience has been so powerful.

Lilly supported me in my role as a breastfeeding mother for nine months, during which she occasionally took me to the hospital to breastfeed real babies. And there, it's pure ecstasy, the culmination of a woman's role: having a baby who depends solely on her for life. Truly moments of intense happiness. In fact, after gender reassignment surgery, a woman can have a child after an embryo transfer, and the diet I followed will allow her to breastfeed.

I found it difficult to stop because even when I slowed down the pumping, my breasts became painful from being too full and required pumping. It took two months to stop completely. The only difference is that my breasts stayed a 38D, much to my delight (another purely female reaction!). When my former best friend Bob contacted me, I didn't know what to do. There was only one solution: meet outside so I could explain myself, and then we could see each other again. That's what happened. But since he wanted to know everything, he came to our place several times to find out all the details and tell everyone. During these sessions, some very steamy moments inevitably took place.

I'm Bob, and I'm continuing the story.

During one of them, Lilly said,

"Vic, show Bob what your whole body has become."

"Do you want me to undress?"

"Vic, darling, if you want him to describe your journey, he needs to know and see everything."

"If you want, OK."

Vic gets up, stands in front of me, and languidly (or should I say, femininely!) lifts and removes her skirt, then her little tank top over her head, unhooks her bra, and sways her bare breasts. Then she slips her fingers into her thong and pulls it down. There she is in high heels, naked in front of me.

"Oooh ouch! You're so beautiful, sexy, and desirable! Take a turn so I can admire you." She twirls in front of me like a dancer, and at the sight of that superb body, her generous breasts, her bouncy ass, my cock is rock hard in my pants. It's impossible to get an erection in front of an old friend, I'm crazy!

Lilly announces,

"If you want, you can touch her breasts, they're real, and look at her privates." As I feel her breasts, she moans and squirms.

"You can also see and touch her female genitalia." I'm crimson with shame and rising pleasure. I slide my hand down to her stomach and her thighs part. I can clearly see her large clitoris and her cleft with an opening in the center. A vulva practically like a woman's. I touch her lips and she shudders. Mmm. I slide my finger over her clitoris and she gives a little shudder and a small cry, then gasps.

Lilly says, "Bob, I can tell you're ready to make love to her, and you, Vic, I think you're dying to be your friend's woman. Go ahead. I admire you both." “And what was bound to happen, happened: Vic came over to me, undressed me, knelt down, sucked my fully erect cock for a bit, and quickly said, ‘Take me right here, quick, I’m dying for it!’ I made her wstand and lean over the back of the sofa, her legs spread and her ass in the air, offering me her most intimate parts. I moved closer and thrust my cock deep inside her, making her groan, ‘Aaaaahhhhaaaahhhhh, yes, that’s good!’ Then I grabbed her hips with my hands and fucked her hard, making her gasp harder and harder, until she exploded in an orgasm. I kept going, emptying myself inside her with an animalistic groan as she rejoiced at feeling my seed deep inside her.”

I finished my interview to tell you her story, and now I continue to see Vic and Lilly, and have become the lover of both women, much to our delight. It's possible that one day we might consider living together, all three of us. But at their request, I allow 'my' two women to continue seeing their regular lovers who come to have sex with them every month. As you can see, sexuality is very important to us, and we don't hold back.

We often have threesomes for our intimate moments, and I've had some discoveries watching two women making out in a very erotic, tender, very feminine way (we're more active and rougher with women!). In the end, I prefer to fuck Vic because it's more pleasurable. I have stronger orgasms because her vagina is a tighter sheath than Lilly's, and when she orgasms, it's so tight I can't move and it sucks my glans in, so as soon as she relaxes, I'm ready to explode. But I'll keep that to myself; I don't want to upset them.

I hope you enjoyed reading our story and that you had some hot moments and pleasure. Feel free to leave your comments; it's always nice to know that our stories are appreciated.

Big kisses to all,

Bob

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u/michelle_sissy100 — 2 months ago