(sigh, I guess my account has once again been locked out. Whatever so I made a new one. I'll post pics again later but here are some things I was planning on posting on my /u/gurlypussy account.
A few chats this weekend led to me retelling a few stories that I thought I would compile here. I'm not trying to write a book but a few people asked some cool questions, I told some stories and copy and pasted most of it here.
My first time with a guy
My first threesome
The first time I was really slutty.
My first time with a guy.
My first time with a guy was when I was in college. I'd had girlfriends in high school but I was just starting to explore crossdressing and was really interested in following through with it so one weekend I did just that. I met a few guys in a chatroom online, exchanged a few photos and picked out one guy in particular. He was nearby and could host which was good because I had roommates at the time and was still pretty secretive about my sexlife. So we agreed on a time for later in the day for me to go to his place with no pretenses other than I wanted to see what it was like to be fucked.
I gathered an outfit and my makeup and went to a local mall that had a few unisex bathrooms. I took one over and changed and did my makeup in there – at the time I wore a wig as well. Once I was finished, it hit me like a ton of bricks that as soon as I opened the door, this would be the first time that anyone would see me dressed as a woman. I practically had a panic attack right there but I put on some sunglass to help hide my face and walked out. I had only practiced walking on heels on my carpet and I nearly fell flat on my face as soon as I stepped out but I wobbled for a moment and then headed toward my car.
As I pulled up to his apartment, I could see him looking out the window for me and he buzzed me in as I stepped up to the door. His door was open and he invtited me in, being a bit more in private made me feel a little more comfortable about how I was dressed but now I was shaking like a leaf and rethinking what I was doing because I was scared shitless of being with a guy. Not that there was anything wrong with him. He was handsome and much older than me. Nothing stunning but a good looking and in shape guy. I followed him into his living room and while I was setting my bag down, he didn't waste any time. I felt his hand slide across my ass and as I stood up, he slid his other hand around my hips and pulled me into a kiss. There it was – the first guys tongue in my mouth. The thing is, it immediately put me at ease and I was glad for him to take charge.
I didn't have much to choose from back then but I was wearing heels, nylons with garters, a short "pleather" skirt, lace panties, a simple blouse with a bra and back then I had to stuff my bra with falsies. He wasted little time unzipping my skirt and getting me down to my panties. We art of erotica kissed and he fondled me all over and then he pulled us to the couch. By this time he had moved my hand to his crotch and I had been rubbing his hard cock through his pants. He undid his belt and then looked at me like it was my turn so I unbuttoned and unzipped his pants...his hand sliding up to my head and gently directing me down toward his cock.
I just sort of closed my eyes and let it happen and it was much better than I thought it would be. I really thoght that I would gag or something but I didn't have any problems at all. He was average size but I was able to take him all the way without any problems and I really liked it. I mean, it was really turning me on. I held his cock with one hand like I like and started licking, slurping and bobbing my head up and down. Moaning and really getting into it. He just tilted his head back and I really think he liked it.
After a little while, he had managed to pull his shirt off and kick his pants and underwear off and was sitting on my couch completely naked while I sat next to him sucking him off. He had also slid a hand down and had started fingering my ass, one finger then two and I think three at some point, getting me worked up and ready for him. Then, he pushed me back onto the couch, opened a drawer on his end table and pulled out a box of condoms and lube. I just laid there, watching as he unrolled a condom onto his cock then lubed it up and followed up with my ass pulling my panties to the side to reveal my ass but leaving them on and hiding my penis. I spread my legs as he laid down onto me, pressing into me a little at a time, moving his hips slowly and moving a little deeper with each thrust. I gasped each time and then he kiseed me, deep with all of his body weight on me and I couldn't breathe he thrusted all the way, stretching me, making me gasp more and pushing me down. I wrapped my legs around him and pulled him deeper and wrapped my arms around his back as he fucked me and we kissed.
He didn't last long and when he came, he came in the condom but it was REALLY good sex. I'll never forget it. We laid there for a little while chatting and he got hard again so I crawled on top and rode him the second time around, then doggie and on my back again and pretty much anything I wanted to try. I didn't stay the night though and after he came a second time, I got dressed again, went home and never saw him again.
My first Threesome.
Several years later, prior to starting to transition but I was already dressing full time, I had a female friend that I was close to and would later be sort of a fuck buddy but wasn't at this point. She was super nice but a little heavy and hard on herself about it but we really got along well and hung out quite a bit. She taught me pretty much everything I knew to that point about makeup and girls clothes and I had come a long way (plus no more wig as I'd grown my hair out).
We had a very kidding, flirty and grabass as sort of relationship. She liked to flash me her huge tits alot and was constanly touching them herself. I think, looking back she probably wanted a relationship with me but sex is one thing and I'm more attracted to guys for that. Anyway, one night we were hanging out at my apartment and she had invited someone that she knew for a while (I can't even remember how) but I had just met that night. We'd gotten together to have a few beers and play some board games on a Friday night. I didn't really expect much other than Jamie (it just occured to me that I should give her a name) coming over and the guy was her sort of saying "oh by the way" at the last minute so I wasn't even really dressed when they arrived. Just PJs, my hair in a pony tail and no make up. Oh well. We went into the living room, threw on some music and started playing....I think Scrabble. We were drinking so I don't remember what we were playing and somehow Jamie was turning into a flirtatious drinking game complete with shots of Yager which she dug out of my freezer.
Pretty soon that turned into quite a display and before I knew it, Jamie and I were making out and putting on a show for her friend Jeff. I think we sort of made out over some kind of dare and Jamie looked at both of us sort of looking for permission and then her shirt was off and she was pushing me into Jeff trying to touch us both.
Before I knew it, I was in just my panties and both Jamie and I were on our knees sucking Jeff's cock....which was magfuckingnificent by the way. It was by far the biggest cock I'd ever seen and probably still is. Not like horse cock but it was just nice, thick and had a big head sort of like a butt plug. Jamie was moving back and forth between me and Jeff and had us both turned on pretty well. She was definately the one in charge and when she pulled me up onto the couch, I moved with her. She pushed me down onto my back and swung a leg over, moving her shaved pussy down onto my face. She had a big ass but I enjoy it when she sat right down on me. She bent forward, spilling her tits onto my stomach and trying to slide down my panties to reveal my hard cock for her. She pulled Jeff close as well so that he was sitting between my legs and she could suck both of our cocks while I ate her out.
Soon though she was just sucking my cock, and rubbing his cock up and down against my asshole, her drool running down my ass crack and making a wet spot but plenty of lube too and I could hear her come up for breath every few seconds talking dirty to both of us. Telling Jeff to "get big cock in my ass and fuck me like a slut" and telling me to "put my tongue in her asshole and make her cum."
It was fucking hot.
Soon Jeff was balls deep in my ass, I was hugging her ass tight, licking her ass and pussy and moaning while she sucked me so hard I thought she might rip my penis off. And then, I just came. I didn't actually expect it and it came on in a second without time to give her warning and I just started shooting in her mouth. She didn't have any problem with it though and sucked me dry. Leaning back and sitting on my face, rubbing her tits once I was done and concentrating on cumming herself. Cum she did. I think I could have drownded with the wet spot she left on the sides of my head. She rubbed her pussy all over my face and scremed and screamed while she came on me.
Then, Jeff is still fucking me, Jaime laid down next to me with her head on my belly and started talking dirty again, telling Jeff to fuck my slutty ass and then cum on her face. Again, it was fucking hot. He pumped me harder and harder and then pulled out, shooting his cum (at this point I realized he wasn't wearing a condom) all over Jamie's face. She turned right around, slid up and kissed me, I could taste my cum on her tongue and Jeff's cum slid all over her face, us licking it off.
We all slept in my bed that night and fucked again in the morning, all three of us, still drunk and running around naked. Jamie became a "fuck buddy" sort of fag hag I guess if you like that term but I only saw Jeff once or twice more and never had sex with him again.
The first time I was really slutty.
Fast forward a few more years, I'm transitioning with HRT (no I'm not having my penis removed but this makes my penis smaller, harder to get erect and even to have an orgasm artistic nude girls but he's me look more feminine and grow breasts.) I live as a woman full time and pretty much date guys exclusively (although ladies are still welcome in the bed from time to time). Jamie and I grew apart and she moved away. I think she's married now and has kids but we hadn't kept up. I kinda think she doesn't want everyone to know that part of his "exploration" and that's okay with me.
Anyway, I have new friends, and it's a Friday I think, maybe Saturday and we're out to a bar a few towns away from where I live. I'm actually not familiar with the place but a few of my friends wanted to go and why not? It's a club atmosphere...dance floor and loud music. I think it's a gay bar....not sure. To be honest, the gay bars in my area are mpl studio galleries actually the best clubs too so it's hard to tell sometimes. Anyway, I'm there, dressed to fucking kill with a very short skirt, thigh high nylons that barely reach my skirt, heels, a transparent shirt and a very sexy lacy bra that shows plenty of cleavage. I've had, waaaay too much to drink and I'm dancing pretty provocatively I'm told. One guy is dancing with me for quite a while and we touch quite a bit. Another guy comes in later and makes essentially a sandwich of me, I think later I decide that these guys know each other but basically I'm letting them feel me up and rub whatever they want. I know that my tits were grabbed and a friend told me that at one point they had my skirt up, my panties pulled aside and my, tiny floppy dick or clit or whatever you like to call it was hanging out.
As the night wears on, more dancing, sweating, drinks and of course, going outside for some air...
At some point, I find myself in the parking lot with these two gentlemen, both touching me everywhere and anywhere they want, then I'm kneeling, two cocks are out of their pants and I take one in my hand, the other in my mouth. I alternate back and forth. I'm literally in a parking lot, leaning up against a strangers car, sucking to strangers cocks. Holy fuck.
One of them steps away and I concentrate on the other. The one that stepped away moves behind me, grabbing my hips and pulling my up to a bent over position. He slides my skirt up over my hips and pulls down my panties to the ground, I step out of them and instinctively spread my legs. I somehow to don't miss a beat sucking cock while reaching into my purse, finding a small bottle of lube and handing it to the guy behind me. He pours it over my ass and is fucking me within seconds.
I think the whole affair lasts another minute or two, the guy I'm blowing grabs my head and starts shooting his cum into my throat, causing me to gag, hack and tear up. A minute later the guy fucking me starts cumming in my ass. I can feel it shooting deep into my ass, not just his cock throbbing and it occurs to me that he's not wearing a condom – fuck.
Another minute later and I'm alone, hands on a car, gasping for my breath, feeling cum and lube slide down my thighs. I look around but can't find my panties. I get down on my knees and look under the cars but the guy who fucked me must have kept them. I'm dripping with lube and cum and can't find my panties. Fuck. Turns out, I also have mascara dripping down my face but I didn't know that until later. I stumble back into the bar, the bouncer instantly telling me to fuck off because I'm clearly way to drunk but one of my friends finds me, helps me into a cab and sends me home. She said that I was popping a tent with my skirt because I could tuck my dick but walking aroudn like I didn't know it. Even better is that I got home, went to my bedroom, stripped off my clothes, plugged in my hitachi, made myself cum all over my belly and tits, turned off the hitachi and then fell asleep. With my bedroom door open to which my roommate found me later that morning. He threw a blanket over me but I was basically laying there, covered in the cum of three men, including me, and lube, naked and having just masterbated.....Yup. I'm a slut and he could have had sloppy thirds if he wanted.
I'm a much bigger slut now. AMA? (edit – formatting)
SarahtheTGurl
