r/transstoriesgonewild

I was working upstate near Massena. Off and on for two months, driving back to Buffalo every weekend. I was fucking exhausted. Construction by day, safety boat work patching a dam. Hot. Grueling. Miserable. Like most of you reading this, I’m just some guy. Tired. Burnt the fuck out. Then one weekend driving home the endorphins hit me so hard I couldn’t think straight. 11pm, still on the road, I redownloaded the app. You know the one. Notifications blowing up every time I passed another town. Nothing. Until this beautiful nurse messaged me. We started talking and she straight up told me she’s strictly a top. I started shaking. Like actually shaking in the driver’s seat just thinking about this 5'6" woman gently taking control of me. Her body was perfect — hourglass, nice tits, tiny waist, that bubbly ass, southern accent, glasses. Totally proportional. Except for the thick 8.5-inch girl cock she was hiding. We kept texting. She told me to hurry the fuck up and get over there. I took a shower, heart pounding, half thinking about bailing the whole time. She said meet her in the bedroom in just my underwear. When I walked in she was wearing this silky robe and I could already see her bulge swinging underneath. My brain short-circuited. I was visibly nervous. She didn’t even hesitate. Just looked at me and asked, “How nervous are you?” I told her I almost left. We both laughed. She goes, “Here… this might calm you down.” Next thing I know I’m on my knees and she’s opening that robe. Right in front of my face — this beautiful, thick, veiny girl cock. She told me to open wide. The second it hit my tongue I knew I was done for. I would’ve done anything she wanted that night. Only problem? She only let me have one position. Made me desperate to come back for more. I never did. That was a year and a half ago. Please breed me again, Mommy. She eventually put me on my side and gave it to me deep, but she wouldn’t let me touch myself. Every time my hand drifted toward my cock she’d growl “You’re not listening” and shove in even deeper. I came so fucking hard I saw stars. She had my wrist pinned behind my back, one hand on the back of my neck, holding me down while she unloaded inside me. Whispering that I was a good boy the whole time. I still think about it. Constantly.

I am a MTF (19) and I posted here the other day about my first time. It was great but the guy has now started ghosting me and after we’d had sex kept asking if it made him gay.

I sucked off a guy on Saturday night and let him cum on my face like he wanted but then he wouldn’t return the favour and got really weird after. I’m desperate for more experience but I don’t know what to expect maybe I should just embrace it?

I’m a 19 MTF from UK and had sex for the first time last night. I’ve lurked on Reddit subs for sometime and always wanted to be able to share my story and now I can.

I’m at university and have been super cautious telling people I’m trans and have never been close enough to a guy to tell him. I’ve had crushes & sucked my brothers friend off last summer but nothing else.

I’ve been chatting to a guy for a couple of months and we’d been meeting up on nights out. He kept asking me to go over and I was so scared how he would take it but eventually I knew I needed to do something so a few weeks back I plucked up the courage to start talking about trans girls and what his thoughts were, I was shocked that he said it didn’t matter to him. I had been bullied when I was younger for being feminine so didn’t expect him to accept me at all.

Anyway, that night I plucked up the courage to tell him that I asked as I was trans and he was really into it. I went over and gave him a handjob which was hot and I let him cum on my chest, I really enjoyed it, I told him he’d have to wait for more.

Our texts had got naughtier and he asked me to go over yesterday afternoon, I kind of knew what was coming so I had prepared myself for this.

Within no time at all we were kissing and his cock was in my mouth, I sucked his cock and eventually he asked if I would like to fuck him. I was so horny I couldn’t say no but I told him I was a virgin which he seemed to enjoy even more.

It took him a while to get me ready but eventually he was able to slowly slide his cock into me, it hurt at first but after a while I got used to it. He fucked me for a few minutes until he told me he couldn’t hold it any longer & he came.

I stayed the night and left this morning very much not a virgin.

I’m happy to chat to anyone if they want to & it is allowed.

Noon struts confidently towards me and leans in for a kiss. Her soft glossy lips shimmer under the dim lights of the room and we make out passionately, building a gradual intensity as our lust for one another is laid bare. She moves to unbutton my shirt but I whisper 'I want you to dance for me first'.

'Dance? Sure darling what is the song?' I take my phone out of my shirt pocket and tap on the screen, and a club beat starts to play. It's a sleazy, hazy rhythm, and Noon's body immediately becomes magnetised to the energy of the song. She sways her hips and tilts her head back, looking at me with a flirtatious smirk. She takes her fingers and rubs them on her shiny lips before guiding them down her neck and teasefully playing with her nipples. All the while I see the outline of Noon's cock pressed ever harder against the tightness of the latex thong, the fabric showing off every curve and crevice of her beautiful package.

'You like ladyboys dancing for you?' 'I do honey' I reply. There is a warm intensity in the room and I see a bead of sweat running down Noon's body as her dance becomes more pronounced, more deliberate as the song builds to its climax. By now Noon's cock is so hard that it's stretching the latex thong in its entirety, so she readjusts the outfit to let her balls hang out, swaying her body until the song concludes. Somewhat exhausted, I pour her a drink to cool down and beckon her towards me. She sips the Gin and Tonic from the cocktail glass while I suck on her balls, they are hot and sweaty but taste delightfully sweet as I run my tongue over them.

The rest of the night is filled with passion. After the seductive dance Noon sucked my cock with vigorous desire, before taking my hand and leading me to the bedroom. She took every inch of my cock in her tight ass that night, but I made sure she kept the latex thong wrapped tightly around her own package. 'You like that ladyboy?' 'Oh yes darling, I think this thong is making me cum'. I look down to see Noon's sweet cream leaking from the thong, running down her legs. Her orgasmic grin makes the sight even more satisfying and I pound her ass until I finish too. Sweaty and a little breathless, I pull Noon's leather necklace towards me and make out with her before we both take a shower.

As Noon departs my hotel room she flashes me her charming smile, knowing she has given her client everything he wanted and more - her perfect job for a foggy London evening.

It was a dark foggy night in London. I was in the city for business and after a long day in the office I'd finally arrived back at my hotel room. I sat in the chair in the corner as the hazy orange hues of the street lights streamed through the hotel blinds, the murmuring of traffic outside.

The previous evening a card had been slipped under my hotel door. 'Slim and sexy Thai ladyboy, an erotic experience for men who crave pleasure' and a phone number underneath. The wording had intrigued me, and during the following day I knew that it was an opportunity I had to take, not least because I wouldn't be in the city for another few months and would miss out on the fun otherwise.

So I picked up the phone and dialled the number, and sat waiting as the phone rang.

'Hi I saw your ad, are you available tonight?' 'Yes certainly, what time would you like to meet?' '9pm please, here is my hotel address and room number.' 'Thank you, I'll see you then'.

I hung up the phone with a grin on my face. She'd be here in an hour, so I had some time to get ready. But before that I was going to lay out what I wanted her to wear for the evening. During the day, between busy meetings, I'd slipped out of the office to a nearby sex shop in preparation for the evening ahead. When I entered the shop the first thing that greeted my senses was the glorious smell of leather and latex combined with the dark, musky perfume of the shop. A couple of minutes browsing and I'd picked out the items for her to wear and paid the bill.

So now I'm back in the hotel room, the items laid out on the table, waiting for her to arrive.

Intrigued to find out more? Like or comment for Part 2!

9pm sharp there's a knock at my door. I look through the peephole and see a tall slender ladyboy standing in the hallway, much to my delight.

As the door opens she immediately holds out her hand. 'Hello darling my name is Noon'. 'So nice to meet you Noon, come on in'. She is tall, presumably in her early 30s, and her tight toned body fits gloriously in the silky silvery dress she is wearing. Noon has rich golden skin and tattoos running down the length of her right arm. Her somewhat angular jawline and seductive smile are the perfect combination, and she winks at me before gazing around the room.

'What would you like tonight darling?' 'Take the items on the table and change in the bathroom Noon, I'll be waiting here'. She runs her fingers over the fabric on the table and I see a cheeky glint in her eye. 'Oh certainly darling, I'll just be a minute'. The bathroom door closes and I lean back in my chair, ready for the show. Behind the door I hear the rustling of cash that I've left by the bathroom sink, and then the sound of latex running over Noon's muscular thighs. And then a pause, before the door opens...

Noon walks into the darkness of the bedroom, perfectly illuminated by the bathroom lights. I gaze up and see the latex thong wrapped tightly around her waist, and as she readjusts her outfit I can see the head of her cock pressed up against the latex, throbbing in anticipation. Noon is also wearing the leather necklace I bought for her, which she strokes playfully as she walks towards me. 'Darling, I can't wait to entertain you tonight'.

Did you enjoy Part 2? Like and comment to find out more!

I'm really struggling with this last uphill push. Maybe it's because my muscles ache and at this point, it feels like I'm pushing an elephant rather thank a bicycle. It's just a little less that a hundred feet until I make the turn onto my street but it feels like miles away. A lot has been on my mind recently and could be taking me out of it physically and mentally? I spot my neighbor, Beth, down the street working on her car in the garage. It's a vintage 80s Porsche. Looks like were both in the process of restoring older vehicles. Anytime she sees me it always looks like she's sucked a lemon. What she doesn't know is how obsessed with her 1 am. Her simple beauty is the most breathtaking sight I've ever seen.my tire is feeling low so let's finish this quick... I believe I'm going to pop over and see what she's repairing since I'm basically done with my exercise route.
"Wow, you look like shit",
, she said in a jocular sense. She
could have meant it thought it's hard to tell. Not to feel a hit to my pride as a man I invite myself to consult with the ongoing project hers undertaking. "Just like a woman to wear out these brake rotors like this, I'm more flabbergasted you're replacing them yourself on such a fine vehicle. Are you sure you can manage"? | comeback sarcastically. Or at least I hope she heard it that way...
In the awkward silence I take note of the vibe of the garage she has made into an auto shop. It seems oddly like how i set up my garage; man-cave like but defiantly having purpose besides drinking beer and watching the garage TV. Hers however is much, much pinker. Even has this DIY string light braided with a boa surrounding the room. "Well, are you gonna help, I know your mouth runs and truck doesn't so keep pedaling or get me that tube and glass bottle".

Without skipping a beat, she gets back to prepping her tool cart for the next step in the brake repair. With command she gave me for the bottle and tube and the worn rotors and pads, ld say she is flushing her brake lines. She's ready for fresh fluids. "Okay, I'm' going to work the pedal and add the oil. I need you to connect to the bleeder tip and let me know when clean" .. "Yeah, yeah, clean fluids gonna come out then I close it off and go the next tire". I interrupted. We start with the farthest tire; the passenger rear tire, then driver side rear, next is the passenger front tire, and finally the driver side front.
From this angle 1 get a peak looking up at her through open areas around the door and notice she is wearing the same biker shorts 1 am wearing. I could see how wide her hips were and how firm her legs looked. I know from past sittings she's got such a juicy peach of and ass. That's probably why she's got men's shorts.
After all, I got these shorts because they gave me room to breath and not constrict my cock to my thighs, so why wouldn't she be using them more room as well.
Next, I focus on is the beads of sweat slowly building up and dripping down her slim calves. Not paying attention to the task at hand I fumble to siphon tube, which comes off the tip and I take a load of squirt with two heavy steams of brake fluid. "WOAH, WOAH, WOAH"! I shout. She quickly gets out of the car and when she sees me laying down on the concrete in my oily state, lets out a snicker and cacks a side smile. "Oops, sorry there, you seemed like you knew what you were doing" she remarked. Did she notice me sneaking an up-close peak? No, I was looking at her the entire time, she didn't look down at me. Unless she just knew I was fawning over her lower half. She goes to help me off the floor, but I bounce up and rip my shirt off so the caustic fluid doesn't fuck up my skin or whatever it’ll do. We both make our way to the sink in the corner.

First thing we did was clean off the stuff that had gotten on my neck and cheek. Without the boggy cotton shirt clinging to my arms and torso she starts cleaning of my chest and stomach where the oil had seeped through the shirt. "Oh, your shorts as well". She pointed out. "Just give them a good wipe off, I have wears on under them anyway. I'm not too worried about that's spot, thanks". She proceeds to do some light dabs with a shop towel and some break clean. With one long wipe she inadvertently catches to edge of my contained cock and I couldn't help it and twitch it as she rubs up against my tip, making the dark wet spot a little bigger. Stunned by this blunder I take a step back and both of us lock eyes. She bursts into laughter, "'m sooo sorry, he he".
Standing there I watch her demeaner change from comical to flirtatious. Giving me a sultry look, I don't believe I have ever seen a woman give me before, she grabs the garage door clicker and proceeds to shut the door with us inside.
"I reckon I was out of line there, only right you get yours". She
spoke softly, then she slowly took off those matching shorts of hers. While processing what's going on in my head, her girl cock bounds out with a throb and drip.
Sweat, like wildflower honey, coming down her sun-kissed, caramel skin was already enticing me to have a taste, but watching a droplet from her hole glisten from the ambient light made my mouth soaked with saliva. With a sudden rush, I now feel the need to take in all her softness and innocence she may have and void her of any remaining purity. I let slip out with a deep breath whisper, “fuck”.

She starts towards me and swiftly rips down my tight garment to mid-thigh, enough to my member into the hot, fresh air. She clenches around it at the base and slowly stroked it up squeezing a surge of precum out of my dick. She then pulled me closer. Penis tips oozing with nectar, only hairs away. Both of our hole's kiss and move apart stringing along a mixture of our secretions. With the outside air cut off, the garage turned into an over of heat and lust.
Sweat accumulating fast on our exposed body parts.
I hesitate at first, but compose myself and go to grab her cock doing the same she had done to me, squeezing even more of her juices out. I lighten up the grip to sensually stroker her girl penis.
She does the same to me. In sync we both take one large breath in and exhale like doing the purest line of coke. Our synchronization of back-and-forth strokes draw us closer and closer to utter bliss. I take my remaining arm and drape it over her shoulder and she braces up against the basin. We are inter-connected like snakes twirling together during their mating ritual. I didn't want to release my grasp of the power that I held in my fingers, and I could tell she wanted to keep her grip to me as well. What was once drops of nectar quickly became a sudden spring shower, coming in hard and wet.
Reality shrinks around me, I center on the sounds of tips and taps of sweet perspiration braking on the cool concrete, the buzz of a run-down floor fan, and our bestial breathing.
This burst of intimate mutual masturbation is interrupted when she goes to reveal a multitude of extra velvety soft skin.

I didn't examine her that much but I could tell she was hiding something even being exposed as she was. I thrust my hips forwards signaling to her I wanted to stuff myself into her cock socket. Beth spreads her opening apart and I work myself in her foreskin enveloping my circumcised shaft. This reminds me of one of the masturbators I have back at the house, but warm and inviting. Within the steamy embrace we start to inset grunts and moans between breaths. While she holds our connection, I sneak a peek to see her radiant face. She's peering down concentrated on her tender grasp. I clench her small shoulders and bring my head closer to her neck and lick up her wetness before | start to suckle on her succulent neck.
Once she got the feel of our movements, she moved a hand to my girthy base making lengthy strokes of inverse of my trusting.
As I push forward, she would tug me backwards along with heaving her flesh over mine to keep me inserted with her other hand. We stay coupled as our self-lubrications makes our copulation frictionless. If she wasn't so petite I would traverse my tongue down to her sweet little nipples, but I feel the extra movement to tear her crop top off would halt everything, so 1 play with her protruding nipples. They were surprisingly defined for being under her shirt and bra. Massaging one betwixt my thumb and pointer finger it reminded me of threading a bolt into a hard-to-reach area on when you're underneath a vehicle. Her mounds aren't too big either, a perfect amount to fit in my blue-collar hands. I get enough of them to squeeze.
I begin to lose inhibition in her essence; I plunge further inside, 1 reluctantly move away from her neck so i can use my other hand to caress her bare ball sack. I fondle them gently, caressing them with every finger, clenching the ever so often like my personal stress ball. They seem to be relaxing me to the point of releasing what I have pent up inside. I want her to release whatever she has imprisoned as well.
Shivering, her strength in her legs give way. The reaction breaks us away from our tug-of-war as letting out guttural moans... I really hope know one heard that. I could feel she was close too, but she stammers towards the door going inside without finishing. Did I cross a line? She presses the garage door opener mounted on the wall leaving the clicker on the counter next to me. I think I get the memo without her having to say anything. As the door opens, she slinks inside tripping over herself because of the shorts around her ankles. I rush to make myself presentable for the public world that I had forgotten about for while within these girly walls.
For a moment my whole world had been an alternative actuality that I would never have dreamed of being in, but it was real. I could feel it. I could taste it. I could smell it. I could hear it. I could see it. I locate my bike and hop on; I walk out to the end of her driveway and survey the road and other houses wondering if there are any 'looky-Lous'. Riding home I replay the garage scene over and over. I'm only five houses down the hill, but I ran though the sequence over a hundred time.
In a trance like state, I drop my bike out form under me and
march to my houses side gate and go into the back yard. Peel down my shorts. Drop my underwear. And jerk off my swollen cock and balls. Pounding away vigorously, I drop to me knees now cupping my testicles how I fondled Beths'. Thinking about her small perky bosom and her pendulous sack. Her meaty shaft and tight waist. Her golden skin and perfect size. I brood over my obsession for only a moment until I ejaculate hysterically. I didn't register it had happened. It all just spued out like streams of brake fluid being pumped out of the caliper lines...

Just a rough draft I wrote on notes. Is there anything there worth a damn?

Happened a few years ago. The summer after graduating high school I was having a look on grindr for a fun time. I was still kinda "in the closet" but I was just beginning to spread my wings, so to speak. That's when I saw a familiar face. She was the trans girl from some of my classes. I knew her going back to pretransition days and we were friendly to eachother in passing. We spoke every once in a while but we never hung out or anything. Since we already knew eachother, I decided to shoot my shot. She replied pretty fast and we got to talking. We very quickly arrange to hook up the next day.

I walked over to her place and went up the stairs. As soon as i get on her floor she opens the door and rushes me into her room. She sits me on her bed and stands in front of me. I can already see her hard-on twitching in her gray sweatpants. I look up at her and she says "you want to suck my dick dont you?" I nod yes and then she says "you want me to fuck you too huh?" And I nod again. She pulls down her sweatpants and for the first time in my life, I have a rock hard cock in my face. It was pretty perfectly shaped honestly. Not too long but not too short and a little thick. I fell in love immediately. I took her dick in my mouth, first time I ever gave a bj. It was very strange at first but it reminded me of sucking my thumb (which I admittedly still do...). I gagged a lot but she was gentle and patient with me. I must've been doing good because pretty soon she started bucking and mouth fucking me. She pulled out and came all over my mouth and chest.

Before I knew it she had me stand up and she pulled my shorts down. I just turned around and got on the bed on my hands and knees. I felt her put lube on my ass and then rub her cock on my asshole. I had never been fucked before, and until then, I only did light finger play on myself. This was completely different. She started slow and it hurt for a little bit but I learned to love it quickly, to the point where I started to rock back into her cock after every thrust, yearning for more.

That's when it happened. About 3 minutes into getting absolutely railed by this hot trans babe, my mom calls. I try to silence it but instead I accidentally answered it. Being absolutely mortified at this point I decide to talk and end the call as quickly as possible. She just wanted to know what i was doing and where i was. I just said I was hanging out with a friend, except that sentence came out of me all broken up because my ass has been under constant "fucking" bombardment. There was a long pause on the other end of the phone as im sure she could probably hear my literal cheeks being clapped. She said "I hope you're not doing anything stupid." I assured I was not and quickly ended the call. After I hung up we started laughing as my date continued fucking me. A couple minutes later she came in my ass and made me clean her off. We made out as we touched cocks together and then got dressed. She told me she loved me and invited me back anytime. She later got arrested and I never saw her again... 🥺 I miss her and think about her sometimes, best fuck of my life!

**Author’s Note: Still new to writing stories like this, open to feedback and suggestions. Thanks for reading!**

I’ve been awake for almost an hour. Lying on my side, ass pointing at him, waiting. Waiting for him to stir. Praying that he would take me when he wakes. When I hear him roll over, my heart begins to race. Then I feel it…

A strong hand on my hip. Two fingers loop inside the waistband of my panties as he slowly slides them down around my thighs. The feel of his rough hands and the cotton underwear sliding down makes my skin tingle. I can feel the goosebumps rippling all over my flesh.

I know he’d rather I sleep naked so I can be even more available for his needs, but the sensation of him taking them off is just too exciting. I can feel a rush between my legs, a slight pain as blood tries to pump into my girlcock but is denied by the chastity cage I ware.

Next his fingers probe me. His hand spreads me open slightly and a large finger pushes against my hole. He rubs my bussy, growing bolder and bolder. Two fingers pierce me. They don’t fit, not really.

He doesn’t care.

I bite my pillow to keep from protesting. He doesn’t like it when I cry out. I’m his, and I should be grateful when he has his way with me.

My asshole strains and stretches as he drives further in. The pain of it is only surpassed my the pleasure. The pace of his fingers picks up, and he starts blasting my prostate. I know I’m leaking like the good little slut I am.

Suddenly his fingers are gone and my excitement grows. I know what’s next, I hear the drawer of his nightstand open. Hear the lid of lube snap open. Then his fingers are back, spreading the slick lubricant up and down the crack of my ass. Readying me for more.

The bed jiggles as he positions his hips behind mine. His thick cock spreading my ass cheeks apart as he slides against my hole, tip to shaft. He’s preparing me for what’s to come, but I’m more than ready. I’m eager. I’ve been waiting for this all morning. Then it happens. He stabs into me hard.

Fuck he’s big.

My tight bussy strains and resists the size, but I’m no match for the force he uses as he thrusts into me. The ring of my anus gives way, and I bite down hard, my nails dig into the mattress. I want to be a good girl. No crying.

His hand finds my tits. The tits he paid for. The hard squeeze distracts from the pain in my asshole that’s protesting the pounding. He begins fucking me harder and harder. He squeezes so hard I think one might pop, but then the hand slides down my side finding my hip. He pulls me into him with every thrust.

If a was leaking before, I must have a small puddle of girlcum forming next to me now. As good as it is I know there’s more, and I hope he gives it to me.

I’m rewarded.

He shoves a pillow under my hips and pushes me into my stomach. Climbing on-top, he mounts my now prone body. He renters me and starts jackhammering. His whole weight slams down onto me with every thrust.

I squirm. I can’t help it. He corrects me with a hand to the back of my head, shoving my face hard into the mattress. When I try to push up, he grabs both my arms and forces them behind my back. His legs pin mine down and I have no movement left.

I’m his and I love it.

He’s lying on me, forcing me down and humping. Shoving himself deep inside, I feel him start to strain. Hips flaring in a way that I know he’s about to fill me up. When I hear his grunting I know it’s time.

I feel his dick pumping inside me, shooting his warm seed. His sweaty body falls down on me, but his hips continue to fire and his balls continue to drain. He’s panting hard, and the breath tickles my face. He lays there for a minute before pulling on my hair, bringing my ear next to his mouth.

He whispers. “I hate how much I love fucking you.”

He slides off me and a moment later I hear the shower. I reach behind me and slip a finger inside myself. I remove it with a nice sample of cum and pop it in my mouth.

Moments later I drift off to sleep, satisfied. The taste of his cum on my tongue.