u/ts2054

This happened after my wife told me she wouldn’t let me fuck her anymore. She’d been fucking other men and the closest I had come in months was using a strapon to fuck her.

One afternoon while I was at work she was complaining about how horny she was. She was off that day and told me she’d masturbated 5 times already. Her bull was out of town and she told me she was dying to have a dick inside of her. Eventually she told me if I could come home early she’d let me fuck her because she was “desperate.”

I made up an excuse and basically ran out the door of work. On the way home she was telling me how horny she was and dirty talking me about how hard she was gonna make me cum. It was amazing.

As soon as I walked in the door, we started making out. My dick was already throbbing and leaking precum into my underwear. I grabbed her by the ass, spun her around, and leaned her over the table to grind on her from behind. Before I could she let out a moan. Her pussy had rubbed against the rounded corner of our kitchen table. She had leggings on but it clearly felt amazing.

She held me at arms length. “Holy shit baby.” She moaned as she started grinding against it. “Oh fuck maybe I don’t need you after all” she moaned as she pushed me away. She grabbed both sides of the table and started grinding against the corner harder. She slid a hand up her shirt and started rubbing her nipples as she kept going. I tried to grab her ass but she pushed me away.

“Stop. you can watch but I don’t….mmmm….need you anymore. Holy shit” she moaned barely able to speak. She grinded the table for 3-4 minutes before clenching the edge and smacking the tabletop as she had a powerful orgasm. It went on for quite a while before she stopped moaning. As her breathing slowed, she started grinding again.

“Fuck that felt good.” She looked at me and pointed to my dick leaking through my pants. “That has never made me feel this fucking good. Holy shit.” She moaned as she kept going. Then the teasing started. “How fucking humiliating…mmmmm….for you” she struggled to talk through the moaning. “A kitchen table fucks your wife better than you can…but…mmm…fuck…this is actually a big piece of wood…unlike that…” she moaned pointing at my small cock again.

By now I was pulling it out and started stroking it. “That’s it. Stroke it with two fingers like the tiny dick loser you are” she moaned “just know….ohhh fuck…fuck fuck fuck” she said moving her hips like she was riding the best cock of her life. “Mmm just know I’d rather have a fucking table than that pathetic thing” she moaned. I watched a few more seconds and exploded. Blowing a load all over myself and the kitchen floor.

She laughed and kept grinding for another few minutes laughing at my small cock and telling me how horrible of a fuck I was. Then she came again. It was just as loud and powerful as the first one. She leaned over the table to catch her breath. Then she stood up with a huge wet sport on her gray leggings.

“I guess I wasn’t desperate enough for that after all. You can go back to work” she said as she went upstairs. I cleaned up and went back to work wondering what the hell just happened.

This happened after my wife told me she wouldn’t let me fuck her anymore. She’d been fucking other men and the closest I had come in months was using a strapon to fuck her.

One afternoon while I was at work she was complaining about how horny she was. She was off that day and told me she’d masturbated 5 times already. Her bull was out of town and she told me she was dying to have a dick inside of her. Eventually she told me if I could come home early she’d let me fuck her because she was “desperate.”

I made up an excuse and basically ran out the door of work. On the way home she was telling me how horny she was and dirty talking me about how hard she was gonna make me cum. It was amazing.

As soon as I walked in the door, we started making out. My dick was already throbbing and leaking precum into my underwear. I grabbed her by the ass, spun her around, and leaned her over the table to grind on her from behind. Before I could she let out a moan. Her pussy had rubbed against the rounded corner of our kitchen table. She had leggings on but it clearly felt amazing.

She held me at arms length. “Holy shit baby.” She moaned as she started grinding against it. “Oh fuck maybe I don’t need you after all” she moaned as she pushed me away. She grabbed both sides of the table and started grinding against the corner harder. She slid a hand up her shirt and started rubbing her nipples as she kept going. I tried to grab her ass but she pushed me away.

“Stop. you can watch but I don’t….mmmm….need you anymore. Holy shit” she moaned barely able to speak. She grinded the table for 3-4 minutes before clenching the edge and smacking the tabletop as she had a powerful orgasm. It went on for quite a while before she stopped moaning. As her breathing slowed, she started grinding again.

“Fuck that felt good.” She looked at me and pointed to my dick leaking through my pants. “That has never made me feel this fucking good. Holy shit.” She moaned as she kept going. Then the teasing started. “How fucking humiliating…mmmmm….for you” she struggled to talk through the moaning. “A kitchen table fucks your wife better than you can…but…mmm…fuck…this is actually a big piece of wood…unlike that…” she moaned pointing at my small cock again.

By now I was pulling it out and started stroking it. “That’s it. Stroke it with two fingers like the tiny dick loser you are” she moaned “just know….ohhh fuck…fuck fuck fuck” she said moving her hips like she was riding the best cock of her life. “Mmm just know I’d rather have a fucking table than that pathetic thing” she moaned. I watched a few more seconds and exploded. Blowing a load all over myself and the kitchen floor.

She laughed and kept grinding for another few minutes laughing at my small cock and telling me how horrible of a fuck I was. Then she came again. It was just as loud and powerful as the first one. She leaned over the table to catch her breath. Then she stood up with a huge wet sport on her gray leggings.

“I guess I wasn’t desperate enough for that after all. You can go back to work” she said as she went upstairs. I cleaned up and went back to work wondering what the hell just happened.

I will preface this by saying, this is not an incestuous story. This is a story of stupidity and embarrassment. My cousin and I have never, nor will we ever, be physically intimate.

I have always had a bad habit of getting conversations confused. I still do it to this day. If I am texting more than one person at a time, there’s a good chance I’m going to send a text to someone I don’t mean to. This story is back when Snapchat didn’t allow you to unsend snaps. This is also when if you were replying to someone it didn’t say their name on the screen until you hit send.

My cousin and I used to be best friends. She and I talked to each other about our relationship troubles and pretty much everything else in life. One spring I was having a particularly rough time with women. I’d go out with them and even hookup and then they’d ghost me.

Well one night I was snap chatting my cousin and a girl whose name started with the same letter. Let’s call my cousin Amy and the other girl Ashlyn. The conversation with Ashlyn was getting hot and it was time to send a dick pic. This is before I realized how small I really am so I sent a regular dick pic with all skinny 3.5” throbbing between my fingers. I hit send and then the screen went to the list of people I’d been snapping. And that’s when I noticed it. I’d sent it to Amy instead.

I immediately sent her a text. “DONT OPEN THAT LAST SNAP!! It’s for someone else!” She laughed and jokingly said “lol I can guess what it is.” We joked around and chatted for a little bit. Hours went by. Then I got a snap. It was my cousins face palming with the words “I forgot.”

I text her and she explained she totally forgot our conversation and saw she had a snap from me and opened it. I told her I was about to die of embarrassment and I profusely apologized. She said it was okay but “I think I figured out your girl problem.”

I’ll summarize but she told me that she hopes I’m good with my mouth because girls usually like a guy to have more girth. I asked her for advice. She was very helpful and we talked a lot about what i could do to make up for it.

One night, my ex and I had gotten into an argument. A lot of it centered around me crossdressing. There are plenty of stories on here of me dressing with her, but her support of it came and went. Anyway, she decided to go see her sister and stay the night there. Which left me with a chance to get all dolled up.

I drove about an hour away, found a rest area, and started getting ready. I threw on a tight little burgundy dress, 4” pumps, some lace panties and a matching bra, and did my hair and makeup. I rode around for a few hours, flirted with some strangers, and took some photos.

After a little bit she started blowing up my phone wondering where I was. She’d gotten home and started drinking wine. I was honest about where I went and she freaked. She told me to come home right now or else. I don’t like confrontation so I just told her I should wait until we both cool down and I’d be back in a bit.

About an hour goes by and she sends me 4-5 pictures. They’re screenshots of a video of me getting railed by a stranger in a hotel. A couple were of me with a cock in my mouth, one was me smiling up at the camera, and a couple were of me getting fucked from behind. “Which one do you like best?” She asked. I asked her what she was talking about and why she was asking. “They’re the thumbnail for your big debut” she said.

Then she sent me screenshots of profiles from multiple different porn sites. She’d made me a full on profile full of face pics and info about me and the video of me getting fucked was in the drafts just waiting to be posted. This was before any of the ID verification or anything on a lot of these sites so she was just making profiles anywhere she could.

I begged her not to post them. She told me she’d started uploading them but if I was home before they finished she’d delete them. I was an hour and some change away. There’s no way I could get there. Then she stopped replying. I raced home and found her passed out with her laptop next to her. All the tabs were open and all the videos had been uploaded. I worked as fast as I could to delete them, but they’d all had several views. By the time I got done with the last one it had over 500 views (including some downloads).

The next day she apologized. She said she thinks I deleted them all but she couldn’t remember where all she’d posted them. Anyway, if you have my videos please don’t expose me 😅

It’s okay. You can be honest

Not long ago a girl that I’d been passively flirting with for months text me late one night. We were both horny and she invited me over. The only condition was that I had to wear a condom. Which is understandable. I was all out so that meant I was stuck stopping at a cvs on the way.

I’ve always hated buying condoms, even before I discovered the small sized ones, but now I almost always just order them online because I try to avoid what happened that night.

I walked into the store and made a straight path to the condoms. The only people in the store were me, the 2 employees, and like 3 women walking around minding their business. One of the women working was restocking the front of the aisle where the condoms were but I walked right by her until I realized the condoms were locked in one of those security cases. They were all jumbled together but I finally found the Skyn snug fit condoms. Which generally work okay for me. I’ve only had one or two come off.

I worked up the courage and asked the lady if she could unlock it. She was nice and walked on over to the case and unlocked it. She stood there as I grabbed a box. I kind of blocked her view as I put my hand over the “snug fit” label. I thanked her and began to walk away. “Hold on dear, since the item is more than $15 store policy makes me carry it to the cashier for you.” I just kind of looked at her. I’d never heard of a policy like this but I’m not one to cause service workers issues over policies they don’t control. I handed her the box(face down) and followed her up.

We got to the cashier, a pretty cute 18-19 year old girl, and the lady handed me the box. “I think you got it from here.” She said smiling and walked away. I stood in line for a couple minutes while the cashier checked out the older lady in front of me. While I waited, the other woman in the store got in line behind me. She was a very naturally pretty girl. Not flashy, but one of those girls that didn’t need makeup and somehow always looks refreshed and put together. If that makes sense.

Finally, I stepped up and slid the condoms to her. She slid them over the thing but they wouldn’t scan. She tried like 3 times before flipping them over. “Ughh they always do this. They put the freaking security sticker over the barcode” we kind of laughed and she tried to peel it off but the barcode came with it. “I can just go get another one” I offered. She shook her head and grabbed her little radio mic they wear. She had an earpiece so I only heard the one side of the conversation but it went like this:

“Hey Mary, are you still on 12?”

“Can you get a price for the 12 pack of Skyns you brought up here?”

“No, they’re the small ones” she picked the box up and read it “the ones that say ‘snug fit’ on them”

“Wow, she’s really putting your business out there isn’t she?” The girl behind me chuckled. I just turned and kind of smiled at her.

I paid for them and went to walk out. I smiled at the girl behind me and she said “remember, motion of the ocean not the size of the ship” and smiled at me.

The motion of the ocean only lasted 45 seconds that night but that’s a whole other story.

So continuing on my sissy journey, my wife was well aware of everything by now. Sometimes she loved it and sometimes she hated it. By now, I was basically pussy free and she was fucking other men. One Friday night she invited her best friend over. Her best friend happened to be a girl that I’d hooked up with years before my wife and I started dating. By “hooked up with” I mean I came all over myself trying to put it in and then the next time we tried I lasted 15 seconds and came in the condom.

Anyway, my wife, Emily, and her friend, Sam, started their girls night while I was out in the yard working. I worked until dark, and by then they were both pretty wine drunk on the couch. Both girls were flirty, bi-curious, and very touchy with each other when I got inside. Emily and I had talked about a threesome with Sam before so I thought tonight was the night. I said hello to them both and went to clean up. I showered quickly and stepped into the laundry room to get some clothes. Our laundry was right around the corner from the living room, and I could hear some soft moans. I quietly peaked around the corner and saw them both making out. It was insanely hot. This was my chance.

I stepped around the corner and knelt beside them. I slowly rubbed up their legs and stopped at their asses. Once I got to their asses they both stopped and asked what I was doing. “Well I figured I’d try to join the fun…” I said squeezing their asses. Emily just laughed at me, “I don’t even let you fuck me anymore, you think I’m gonna let you embarrass me in front of my friend?” Sam kind of giggled and responded, “besides…from what I hear you’d rather be the one getting fucked than doing the fucking.” They both laughed hysterically as they fell over each other. I just looked in disbelief with what I’m assuming was a dumb look on my face.

“Oh come on, she’s my best friend. You think I’m not gonna tell her my husband dresses like a slut and sucks cock?” Sam continued to laugh. I stood up not sure what to really say. “Not to mention I know for a fact Sam doesn’t want to try that little shrimp dick again. Do you dear?” She said rubbing Sam’s hair as Sam shook her head. “I tried to block that out actually.”

After they both got done laughing, Emily looked at me “you know what would be fun? If you dropped that towel, show Sam what she’s NOT missing and then go put on something cute for us.” I knew better than to argue, and to be honest I was insanely turned on. My cock was hard under the towel and leaking precum already. I dropped my towel and my rock hard 3.5” sprung free. Sam almost choked on her wine. “I forgot how skinny it was….and short…” she laughed and then gave a sad “awwww.”

I went to pick the towel up “no. Walk to the bedroom naked like the slut you are.” I walked into the bedroom and started getting ready as their laughs echoed down the hall. They spent the whole time I got ready either making out or laughing about my tiny dick and how fast I came.

I did my hair and makeup first then slid on a pair of black thigh highs, black lace panties, a black lace bra, black 4” heels, a black skin tight miniskirt, and a cute pink flowing blouse. I looked pretty cute not gonna lie. I’d never dressed for another woman (especially a hot one that I’d always wanted to try fucking again) but I worked up the courage and stepped out into the hallway and down to the living room.

As I stepped into the living room, Emily told me to give a little spin. I did as I was told and both girls clapped a couple times. “You are a cutie!” Sam said hyping me up “maybe you were meant to be a girl and you just have a big clit.” Then Emily told her all about how sissies like me called our small dicks “clits.” I spent the next 30 minutes answering a million questions. Mostly about how much of a slut I’d been and all the cocks I’d been with.

Then Sam finally asked, “so what do you two do since he doesn’t fuck you?” Emily just laughed. “Oh girl, sit back and watch…” she turned to me “on your knees.” I did as she said. She came back soon with her strap on around her waist and over her clothes. “Why’s it over your clothes?” She asked. Emily looked at me, “tell her.”

I looked up at Sam from my knees “because I don’t get to see her…” Emily quickly cut me off. “No. Tell her the real reason exactly like I told you.” I kind of looked down and then back up at Sam “because dick sucking faggots like me don’t get to see hot women naked.” Both girls just laughed as I began to suck the strap on. I deepthroated it passionately while the girls talked.

Emily told her how she couldn’t take me being such a bad fuck anymore and she started fucking guys we all knew. It was a small town and we all worked in the same field, so I’m sure many people learned my secrets.

After sucking her for 10-15 minutes, Emily bent me over the arm of the couch. She spit on my tight little hole and slowly slid inside of me while Sam watched. I gasped as she stretched me out and grabbed at the couch cushions. Sam was amazed. Emily called her over and they whispered quietly. As Sam stepped away Emily said “remember, she’s a dumb cock sucking loser so she doesn’t get to see you naked…but a little teasing should do the trick” they both giggled.

Sam stood in front of me while Sam kept pounding my ass. She was fucking me deep and very steady. Her pace wasn’t that fast but she was slamming the fat cock inside of me hard. Sam slowly started to strip. She’d always been hot, but it was clear she was in better shape now. She had defined abs, toned legs, a perfect bubble butt, and the cutest b cup tits with rosy nipples. Once she got to her panties and bra she stopped stripping. She sat on the couch and spread her legs in front of me. Just out of reach. And she started rubbing her pussy through her panties.

“Oh fuck.” I moaned as I was amazed at how hot she was and how close her perfect body was. I wanted her so bad, but here I was with a dildo in my ass dressed like a sexy girl. “I bet you wish you could fuck a girl that hot don’t you slut?” I just moaned through the thrusts “mhmmmm.” Emily kept thrusting as Sam began to moan watching me get pounded. “You know even if you weren’t a cum guzzling faggot she wouldn’t fuck you. Tiny dicks like you don’t fuck hot girls like us. Do they Sam?” Sam just moaned and laughed “definitely not. Worst sex of my life. If you could even call it that.”

Both girls continued to tease my little dick, call me a dumb slut, and tell me how I’m a better girl than a man. I couldn’t take it anymore. I grabbed the cushions and my little cock grinding against the arm of the couch exploded. I screamed and moaned so loud as my body shook. Then I collapsed on the couch. Sam was amazed how hard I orgasmed. They both teased me about orgasming like a real girl.

Emily pulled out and reached out to Sam. They kissed and Emily led her to the bedroom. I got up to follow. “No no no. You don’t get to watch. But I’ll leave the door cracked so you can listen” and that’s what I did. I laid on the couch and listened to the two hottest girls I knew hookup while I was dressed like a total slut.

Contrary to popular belief, I was not always premature. Now I struggle to last more than a couple minutes, but I used to last forever. This is the story of my first time experiencing premature ejaculation…

When I was 21, I met a girl named Katy. Katy was a cute brunette. She had very soft features, sweet eyes, a cute smile, a nice round ass, and cute, perky b cups. We chatted for a bit on tinder then decided to meet up. We went out to ice cream and had dinner (in that order) and then I went back to her place. I ended up having sex with her for 48 minutes. Which was amazing. After a very successful night together, we continued to chat through the week.

The next weekend, she was house sitting for her grandmother and invited me to come over. She said she couldn’t wait to experience it again. She was amazed at how long the sex lasted and was craving that again because all the guys in her past came too quickly. She was sweet so she didn’t put anyone down, but said she always wished sex lasted longer.

The weekend came and I met up with her at her grandmothers house. We chatted for a bit, but it was clear why I was there. We started kissing in the living room and it was on. We made out all the way to the bedroom. Breaking momentarily to makeout against a wall in the hallway.

Finally, we made it into the guest room. We stripped each other down and she laid on her back as I kissed down her body and began to eat her out. I played with her tits and ate her pussy for quite a while. Eventually her squirming and moans became too much and she pulled me up by my shoulders. “I need you inside of me” she moaned.

I reached over to the night stand and grabbed one of the condoms off of it. I was sitting between her legs with them wrapped around me, her wet pussy waiting for my hard cock as it rested against her. I unwrapped the condom and grabbed my hard cock. I was watching her squirm as I slid the condom over the head of my cock. As I did, I let the head rest against her wet pussy. I finally rolled the condom all the way to the base of my cock and it happened.

I was checking out her tits as she rubbed them waiting on me to stick my cock inside of her when suddenly and without warning my balls tightened and I unloaded into the condom. My eyes slammed shut and my body shook as I came harder than I think I ever had before. Finally, I stopped cumming to look down at her face in amazement. “Did you just cum…?” I simply nodded. She giggled, not in a mean way but in a “I can’t believe this” way. “I didn’t know that could happen” she said confused. I told her I had no idea it could happen either.

We ended up hanging out the rest of the night and hooking up again for a totally normal amount of time. And I went years between that time and the next time I prematurely ejaculated. But the next time it was here to stay.

Whenever my (now ex) wife found out I was a sissy, she had a mix of emotions. We played around with things a lot and it opened up our kink world, but she definitely wasn’t 100% supportive. Lots of times she would just tease me about it. Sometimes it was in a backhanded way but was still hot. This story she was just kind of mean tbh. But it was pretty hot. Also, she used the word “f*g/f*gg*t” a lot. I don’t like that word, but I’m just quoting her. So if you also don’t like that word maybe avoid the story.

It was late one night, and she had been drinking some wine. She was feeling frisky, and I thought I would get lucky. We hadn’t fucked in a while and I was so horny! I walked over to where she was sitting on the couch and started kissing her neck and rubbing her inner thigh. She quickly pushed me away. I looked at her confused. “Don’t pretend like you even want me. I can’t give you what you want.” I asked her what she meant. She opened her phone to her photo album. “You have never enjoyed fucking me like you enjoy this” she said opening a video of me giggling as i sucked a man’s cock. “It’s okay. I love you for it, but you’re gay as fuck and you need to stop pretending.”

I tried to reason with her that I could enjoy both, but she wasn’t having it. “Stop.” She basically screamed at me. “Tell me you wouldn’t rather be dressed like a fucking whore right now.” I didn’t really answer because I didn’t know what to say. I was confused so I just looked at her. “See. You’re a faggot. Or a sissy. Or cross dresser. Or whatever the fuck you are. And that’s okay. But i don’t have a cock and we both know all you’re gonna be thinking about is this while you fuck me” she said swiping through her album of me being a sissy.

I just kind of stood there while she swiped through them. Then sat back on the couch. “Just go put it on” she said. “Put what on?” I asked. “Whatever slutty outfit you’d rather be wearing.” We just looked at each other. “Go! You dumb fucking sissy.” I jumped up kind of losing my arousal at her tone. But I went upstairs and threw on a black set of lace lingerie and a little black dress. As I was putting on my heels, she walked into the bedroom with her makeup bag and a long brunette wig.

She let a homemade sex video I made with a man play as she did my makeup. She teased me the whole time about how I was a cock hungry whore and a cumslut. And how she supported me and would even find me a guy to fuck me. But then it would switch back to her calling me a faggot and telling me how it should’ve been obvious because my cock was so pathetic.

After she got my makeup done she went into the closet. She came back out with a strap on over her clothes. “Why is it over your clothes?” I asked confused. She’d pegged me before but she’d never worn it dressed. “Because faggots like you don’t want to see hot women naked. Now get on your knees bitch.”

I did as I was told and got on my knees. She was all gas no brakes as she shoved the dildo down my throat. She fucked my throat until tears were streaming down my face. I’d never experienced this side of her but she had no mercy. She finally pulled it out of my throat and I gasped for air. “Bed bitch.”

I crawled onto the bed and got on all fours. She quickly shoved my head down and began fingering my hole. She grabbed some lube off the night stand and worked it into my tight boipussy. She started rubbing my hole with the dildo. “Beg for it bitch.” She said teasing me. “Please fuck me. Please!!” I moaned as my hips involuntarily moved against her. “More!” She screamed and smacked my ass. “Ple..” I got out before she slammed the dildo all the way into me.

My hips fell forward as the pain pulled me away from her but she followed me down to the mattress and kept it buried inside of me. I pushed my head into the blankets and grabbed them clenching them between my fingers. “Fuuuuuck!!!” I screamed into the bed. “Oh don’t act like you can’t handle it. Your little boyfriend’s cock is bigger than this” she screamed as she started fucking me.

I regained my composure and moved my hips up so she could fuck me harder and deeper. She fucked me harder with every thrust. It was definitely an angry hate fuck. After a bit she grabbed my glass off the night stand. It had some water in it from the night before but she just tossed it on the floor making a mess. “Put this under your pathetic cock. And don’t spill a drop.” I did as she was told.

“Rub that little cock bitch” I did as I was told and started stroking slowly. “Just admit it. You’re a little sissy faggot that wished this was a real cock” I just kept moaning until she slapped my ass as hard as she could “fucking admit it bitch” I moaned and screamed at the slap. “Okay I admit it!”

“Fucking say it slut.” She said smacking me again. “I’m a little sissy faggot! I wish a real man was fucking me.” She squeezed my ass. “Keep going whore.” By now I was in an altered sissy mindset and just started blurting out every sissy thought I ever had. “I wish you were a man about to breed my sissy hole. I only want cock. I never want to fuck pussy again. Just whore me out to real men and let them breed me because I’m a tiny dick sissy faggot” I moaned as I started cumming. I shot a huge load into the glass and went limp for a second.

She pulled out and jumped off the bed. “On your knees bitch.” I did as she said and again she shoved the dildo down my throat as she took the glass from me. I’d never done ass to mouth but it was so intense. She fucked my throat again until she pulled out and grabbed my wig. She pulled my head back and poured my own cum all over my face. She tossed the glass on the floor and took a picture of me covered in cum.

“Gah you really are a fucking faggot. I can’t believe I married such a pathetic excuse for a man. I’ll be watching porn with real men if you need me” I cleaned the cum off my face and walked downstairs a bit later. And true to her word she was masturbating to porn. She let me watch but that was it.

This happened after my wife admitted to cheating on me. We had come to terms with things, and we were in the infancy of cuckolding. One evening she came home from work INSANELY horny. She was always horny, but this was next level even for her. She barely made it in the door before she was stripping her own clothes off. We made it to the bedroom and I ate her out for a few minutes before she pulled me up saying “I need a dick inside of me now.”

I slid a condom on as usual and guided my cock to her soaking wet pussy. I gave her all of 45 seconds of sex before busting in the condom and rolling off of her. She groaned and slapped the bed. “And you wonder why I fuck Zach.” She grabbed her vibrator and started using it brushing my hand away as I tried to help. After a few minutes, she expressed more frustration. “Can I at least call him?” I looked at her confused. “If I can’t fuck him for real tonight, can I at least fuck him on the phone so I can cum? I’m dying over here.”

We talked a little bit and we set some ground rules. I was fine with her calling but it couldn’t be FaceTime and I got to listen. She warned me I probably wouldn’t want to listen but if that’s what it took she was fine with it.

We both laid in bed as she called on speaker. He answered a bit confused. She explained how she was insanely horny and I had just busted in under a minute. She told him I ran to the store so they had a few minutes for him to help her get off.

He was clearly excited as he laughed about me cumming so fast. “Are you still making him wear condoms?”

“Mhmm” she moaned as she already started using her vibrator again. “You know only big cocks like yours get to fuck me raw baby”

He laughed again “I have no idea how a slut like you ended up with him. I love my boy, but damn he’s got a little dick”

She laughed with him. “Tell me how bad you wanna fuck me again daddy” she moaned

By now I was already getting hard again. I’d never thought of doing this before but something about it was turning me on. I slowly began rubbing my cock already leaking precum again

He started going into detail about how he had fucked her before. They’d fucked on his boat when she said she was with her girl friends. He told her how tight her pussy was around his cock and it was the best pussy he’d ever had

“That’s because it never gets stretched by (my) tiny cock” she moaned louder and louder. “Fuck I’m gonna cum already daddy. Tell me how good it is”

He moaned into the phone and told her how he wanted to bend her over again and fuck her like a cheap whore. That’s all it took. She had an insane orgasm. With her free hand she grabbed at the sheets and screamed loudly. As her breathing slowed and her orgasm subsided she moaned “Moooore baby!! I need more!!”

“Mmm fuck that was hot baby. The only thing that would be better is if you were cumming all over my cock. Are you ever gonna let him fuck you bareback like I do?” He chuckled

“Never” she moaned “his dick is so tiny he should have to jackoff with a condom on.” I looked over at her with my dick between my fingers and she nodded at my nightstand and mouthed the word “now”

My friend laughed. “Awww don’t be mean to the little guy”

“You don’t know what it’s like to be this frustrated!!” She moaned as I slid a condom on my dick.

Their dirty talked continued. It centered around him having a way bigger cock than me and how she needs him to cum in her again. She missed creampies but they wouldn’t be right with me and big dick men like him get to use women however they want. She begged him over and over to fuck her and practically drooled over how good he had fucked her.

It took all of 2 minutes of this before I couldn’t hold it together. I busted again filling the condom up trying to stay quiet. But that didn’t matter because she was moaning so loud. My post nut clarity kicked in and I felt very strange about this whole thing. I ended up stepping out of the room as her moans continued for another 15 or so minutes.

After she was done she came out and thanked me for letting her get that out of her system. He managed to talk her through 4 orgasms during that call.

This story is a continuation of me telling my sissy life in chronological order...I'm sure I've forgotten some stuff along the way, but I'm doing my best. After my last story (here), I ended up getting married. She had no idea for a year or so, then she find my sissy email. I had sloppily emailed myself off the wrong account and she found everything. She struggled with it, as to be expected, but after a few months she ended up being okay with it. Up to this point, she had dressed me up but I'd never been full femme. I didn't do my makeup nor shave smooth...until this night...she had already started turning me into a cuckold, and this was just another push to me being totally pussy free...

I was at work whenever she text me "I think tonight's the night..." I responded very confused because we hadn't been talking about anything. "I think I want to meet Taylor..." That excited me. She'd never called me by my sissy name, but it made my little cock jump in my underwear. She told me she wanted me to go all out. Show off for her the way I had shown off for men in the past. The rest of the day drug by as I eagerly awaited 5 o'clock. Once I was off, I rushed home. The second I walked in the door, she handed me a bag from the store and told me to get cleaned up. She'd be waiting in the other room. I stepped into the bathroom and opened the bag. It had hair removal cream, a flowery smelling body wash, a razor, shaving cream, and lotion.

I quickly applied the cream then shaved my face nice and smooth. After the cream set for the time it needed, I jumped into the shower. Within minutes, I was silky smooth everywhere below my eyebrows. I quickly scrubbed myself clean and stepped out of the shower. I wrapped the towel around me and dried off. Drying myself off while totally smooth was always such an amazing feeling. After I dried off, I rubbed myself down with lotion. I felt so smooth and smelled so girly and feminine...I loved it.

I walked into the living room totally naked and totally smooth. Emily just looked at me...then looked down at my little cock. It looked even smaller and more pathetic than usual when I was smooth, and stepping into the cold living room it was barely more than a bottle cap resting on my balls. She giggled "No wonder you wanted to be a girl...you're basically one already" she said pointing to my tiny cock. She guided me over to the floor. I sat down and she did my complete face of makeup. I looked amazing when she was done. Seeing myself in the mirror I didn't even recognize myself, and I didn't even have a wig or outfit on yet. "Go upstairs...I laid something out for you...I'll be waiting" She said giggling. She'd always been bicurious and she said having a feminine looking guy fuck her might be a fun way to test her theory.

As I got upstairs, I saw a brunette wig, black lingerie set, black 4" pumps, and a black bodycon minidress. I slid the thigh highs up my smooth legs, the lace border snuggling fitting around my mid-thigh. I wrapped the garter belt around my skinny waist and attached it to the thigh highs. I snapped the matching bra/corset on and spun it around so it was fitting properly. I pulled the dress over my head carefully so not to mess up my makeup. I got my wig on and ran my fingers through it as it fell below my shoulders. I stepped into my heels then turned to face myself in the mirror. It was the hottest I had ever felt in my life. I didn't even recognize the woman standing in front of the mirror. I took a minute to enjoy the view then slowly walked downstairs.

As I stepped back into the living room, I saw my wife in a white lingerie set rubbing her clit with her vibrator. Her moans were insanely hot and my cock was leaking already. Emily slowly opened her eyes and her jaw dropped as we made eye contact. She was amazed at how hot and feminine I looked. She stepped over to me and we began to makeout. As we did, I started getting handsy. My hands grabbed her ass and my cock pressed against her stomach. Everything was going fine, then she stopped and pulled away. "I cannot do this...you...you're a girl...." She said. She went on to explain how she thought this would be hot, but I am too feminine. She kept saying "you're not a man" and my cock barely even made a bulge in the dress even hard. She told me to wait there and then walked upstairs.

She came back down a few minutes later with a strapon around her waist. I didn't even know she owned one. She said she was going to ask me about trying it one day soon, but with me looking like "A total slut" she figured now was as good a time as any. I looked down at it; it was a girthy 8" dildo and it looked amazing. She saw me looking and grabbed my shoulder pressing it down. I instinctively dropped to my knees and began sucking her cock. "See that...that's a real cock" She laughed as she ran her fingers through my hair. I moaned on the big cock as my drool began running down her shaft. "I bet you wish it was real don't you little slutty girl?" she giggled. I moaned with a mouthful of cock "mhmmmmm." She laughed "no no...let me hear you say it." I looked up at her and pulled the cock out of my mouth "I wish it was a real cock in my mouth." She laughed as she shoved it back in my mouth. "I knew you were a slut...but who am I to talk...maybe you can suck Zach's with me sometime" she giggled (Zach was one of the guys she cucked me with). "Be sure to get it nice and wet baby...I'm gonna stretch you out with it soon..." she moaned.

I kept sucking her big cock until she'd had enough fun. Then she pulled it out and guided me up with her hand. I followed her to the end of the couch then she pushed me over the arm of it. I was bent over with my bubble butt in the air and my dress showing it off to her. She got behind me and smacked my ass squeezing it hard. She began to tease my tight little hole with the head of her big cock. I felt her pressing against me..."I guess I'll be nice..." She said as she stepped away. She grabbed some lube from the table and began to rub it into my boipussy. It felt amazing to have her finger me and my moans were instant and instinctual.

Her finger was quickly replaced by the head of the cock and she wasted no time pressing it into my ass. I gasped loudly as she stretched me out. I grabbed at the couch and let out a loud "ohhh fuck yes!!!!" as she penetrated me. She quickly began to thrust into my tight hole. The thrusts were consistent and deep and I was leaking precum everywhere. The whole time Emily was spanking my ass, telling me how much fun this was, and reminding me how she had a bigger cock than me.

As her thrusts continued, I felt a familiar feeling building. My cock was rubbing against the couch and I couldn't take it anymore. I let out a long moan and screamed "Fuck Emily I'm cumming!!!" as I exploded all over the arm of the couch. Emily giggled, "Wow even when you're the one getting fucked you can't last more than 5 minutes." She thrusted all the way through my orgasm. It felt amazing and my whole body shook for what felt like a solid minute. As I finished I collapsed, and I heard Emily unbuckling the strapon. She unbuckled it and stepped away. "Stay just like that...I want to admire my work."

I stayed bent over, face down ass up with the big 8" cock balls deep in my ass. Emily grabbed her vibrator and laid back in the recliner spinning it to face me. "Damn you are hot...you're definitely hotter as a girl..." she leaned back and began playing with herself. Her moans were loud and she continuously reminded me how I was no longer a man. She loved reminding me how feminine I was, how well I took cock, and how I never fucked her like a real man and it was obvious why now. Within a few minutes she was cumming. Her orgasm was powerful and it looked like she was going to rip the armrest off as she climaxed. As she finished cumming, she gasped loudly trying to catch her breath.

After she regained her composure, she walked over to me, kissed me on the forehead and said "that was fun." She started to walk upstairs as I started to lean up, "Get cleaned up...but dear...I'm having a girls night with Taylor all night." She smiled and winked at me "Get dinner started...I'm gonna go play with myself for a bit." I giggled at her orders, got up, cleaned myself up, and began cooking dinner dressed like a cute little slut as her moans echoed down the stairs.