My first sexual experience with a man happened relatively recently, over the holidays. I gave full details about it a couple of months ago in my [first posts to this sub](https://www.reddit.com/r/gonewildstories/comments/3zxoal/got_fucked_for_the_first_time_over_the_holidays/). I took a long time building up to it, but reached a point where I knew I had to take the plunge and just hook up with a guy. It was an amazing night, and I saw him twice afterward, but he was married. Things got complicated, and he decided to break it off with me.
Back then, I was in full girl-mode around my house and with close friends, but for the most part, my public appearance was more genderqueer. Recently, I’ve become a lot more confident and am now a full-time girl. This wasn’t as big of a leap as it probably sounds–everyone in my life has known, for a couple of years, that I’ve been in the process of transition. I was just more comfortable experimenting privately with my look before going fully public. Still, the reactions have been interesting, with some friends being more accepting than others.
I’d known Chad probably for about a year before all of this, and mostly from hanging out at a local dive and sometimes at house parties. We’d had lots of great convos, but there wasn’t any apparent mutual attraction. We never hung out one-on-one, though he did invite me to a few smaller get-togethers that were a lot of fun. I’d describe the relationship as being somewhere between good friends and drinking buddies. He eventually left town for several months, far enough away that he visited rarely, and so we hadn’t bumped into each other for quite a while. My full transition happened over this period, and a little over a week ago, we saw each other at the local dive.
At first, he didn’t even recognize me, but of course, knew my friends. It was really strange, but also amusing to sit at the table with him. He was really polite, but there wasn’t any sign of recognition, and I could tell he was attracted to me. He eventually asked my name, and that’s when I asked him if he wanted to call me by the name he always had, or by the one I was using now. That really confused him, but at that point, he stared at me intently, and then there was the sudden look of recognition.
He seemed really blown away, and said as much. He was really congratulatory and flattering about my new look, and we really chatted it up that night. He’d moved back into town, so I’d be seeing him more often, he said. We’d chanced onto the topic of Fallout 4, and he offered to show me a few things about it. (I only started playing recently, sue me!)
Let me say here that it had been almost three months since my last hookup, and I couldn’t stop thinking about finding a new guy. Instead of satisfying my curiosity, my experiences with the married guy really lit the fire for me and I’d been burning for more. To be honest, this greatly contributed to my full transition–I felt it was time to start sending out the message that I’m into guys. The thing is, it didn’t exactly start a sexual revolution for me. I started getting lots of flirtatious advances from guys who I didn’t know from before, but I wasn’t sure how to handle that. Reactions among my friends had been generally good, but nothing there seemed to hold sex potential.
I wasn’t sure how things with Chad would go. We’d been friends for a good while before, and I was afraid it might feel awkward for him. I knew I found him attractive, but he’d always been Chad–I’d only been Lexi for a short while. On the other hand, he’d never asked to hang out solo before, and I was getting a very different vibe from him. And like I said, my panties were, in general, getting hot.
So the night for him to visit came. We hung out and watched Netflix for a bit, and then we did actually play some Fallout 4! The vibe continued. It wasn’t super flirtatious, but he was definitely being different, in a good way. It felt more than friendly, but it also felt a little cautious. He was just being a guy and letting me be a girl around him. It was nice, but nothing happened that night. Here is where I will link some text messages and let them start to tell the story. I have edited these together to avoid the pain of scrolling multiple images, but have changed nothing else, save for hiding Chad’s number:
[Part I.](http://imgur.com/UcXfU02)
My heart sunk a bit when he said we’d always be friends. But then, he also clearly found me attractive, and I felt butterflies when he asked if we should hug, and of course, happy that he wanted to hang out again.
I spent the next day shaving (everywhere), trying on different outfits, and making sure my makeup was impeccable. I settled on a tight-fitting sweater dress that came down to the middle of my thighs, and a pair of lacy black panties in case things got hot. I wore nothing else except my favorite body spray, and really enjoyed prancing around in front of him, knowing for sure that he was into me.
Continuing that night: [Part II.](http://imgur.com/AFzjI0y)
While we were watching a movie he had placed his hand on my thigh. I really did feel like I was going to faint when that happened. He’d rested his hand there for a while, and then started teasing just a little by letting his fingers brush down the inside, and squeezing me there just a little bit every now and then. He casually worked his hand up to the bottom of my hemline, but never went further. When it was time for him to leave, we hugged. Really tight. For a long time. Then he slid his hands down my back and started rubbing them over my butt. I looked up at him and we started kissing. We made out like that for a couple of minutes, kissing ever more passionately as he became less shy about squeezing my ass. Before too long, though, he said he had to work early and made a hasty retreat. I wasn’t sure what to think when he left, but it was still an amazing feeling. And god, was I getting horny!
I didn’t hear from him the next day and became a little worried that he’d had a crisis over what happened. He didn’t leave me hanging for any longer than that, though:
[Part III.](http://imgur.com/H4Yst5j)
I can’t tell you how horny I was getting during this conversation and how happy I was that he really seemed into me. At this point, to be honest, I’d have let him do anything he wanted if he were there. He was becoming a lot less shy:
[Part IV.](http://imgur.com/nDuyFQB)
Full disclosure, I couldn’t resist toying myself after I sent him the naughty pictures. I was loving the feel of teasing him, and the feel of knowing he wanted me. Things were clearly going to pick up the next time we met and I was soooo overdue for it.
If there was any doubt about that, though:
[Part V.](http://imgur.com/EvRhZnT)
I was definitely playing coy, there. I was glad he seemed interested in more than a one-time hookup, but I honestly didn’t care at that point: All I had on my mind was finally getting some cock. If he’d told me he just wanted to hit it and quit it, I’d probably have asked how soon he could get over to my place. Still, I seemed to have the upper hand and was *really* enjoying making him sweat me and show how much he wanted me. The pauses in conversation where I wasn’t answering were intentional. I got so turned on when he started to apologize, I guess because it was just reinforcing for me how important this was to him.
I was super turned on when he arrived that night, his last text made it pretty clear that we wanted the same thing. I was wearing some yoga tights over the panties in the picture, along with the shirt that you can see the bottom of–it fits my body tightly and is a favorite.
We kissed at the door again, and he wasn’t the least bit shy about playing with my ass. He gave it a good spank and said we should get the root beer into the refrigerator.
In the kitchen, we started making out again and things got pretty hot. I started moaning softly as we kissed, at first involuntarily, but then intentionally, to let him know I wanted more.
He complimented my lips again and rubbed his thumb across them. At that point, he said he couldn’t believe he hadn’t seen my bedroom yet, and I asked if he’d like to. He told me he wanted to go back to my room and for me to suck his cock.
We did, and I did. He’s huge, by the way. Probably about 7.5″ and really thick. If he’d been any bigger, I’d have been afraid of doing anal with him. Actually, I *was* a little bit afraid, but was way too horny to care. I sat on my bed and he unzipped, pushing his super hard, slippery cock in my face. I didn’t waste any time, and started tugging and sucking him. He moaned really loud and started thrusting into my face. He told me I was really good at it and that at the rate I was going, he wouldn’t last long. I made it last. When I could feel him getting close, I’d squeeze his shaft and slow down. When I felt him settle down, I’d start back up again, edging him a few times that way.
He eventually had enough of that and pulled back, telling me he wanted to cum in my mouth. I got down onto my knees and stuck out my tongue, and he stroked himself to completion, shooting hot ropes all over my face and into my mouth. I sucked him clean and swallowed while he watched. After I cleaned up, I found him in the living room. He told me that I’d made him cum harder than he had in a long time. My cunt was burning. I wanted to go toy myself!
Instead, we snuggled on the couch for a while and drank the (hard) root beer and Netflixed. After a while, he got hard again and started grinding into me from behind while sliding his fingers down my inner thighs, under my butt, and into my panties, squeezing the hunk of flesh just below my entrance, teasing around with his thumb.
I could tell where things were going and so excused myself to the bathroom, where I lubed myself up really good. I came back into the kitchen to get another root beer, and he cornered me against a counter. He started squeezing my ass again, and his fingers found their way under the back of my panties and started teasing around my asshole.
When he realized I’d lubed myself, he just said, “Hell yeah.”
He turned me around, and slid my booty shorts down to my ankles. He played with my butt some more, slapping it pretty hard before slipping my panties down below my ass. He said that my ass was even more amazing in person and continued to play around with my hole using his fingers, before kneeling and burying his face in my ass, licking around my hole. We were both getting super turned on, I was moaning and he was pushing his cock up against the back of my ass. Finally, he grabbed my hips and told me to push my ass out. I put my hands on the counter and arched my back.
He eased in, sinking in only an inch or so at first before pulling out and then pushing back in about to the same depth. I was on fire! Moaning, arching my back, wiggling for him. He kept at it, teasing me by slowly going deeper and deeper that way. It was probably five minutes before he finally thrusted all the way in and I felt him slap up against my ass. The feeling was incredible. He really stretched me out good and I literally thought I was going to cry from the pleasure. I loved the feel of his hot cock throbbing in me, pumping in and out, pushing deeper every time until he’d taken me completely.
He grabbed my hips tightly and started fucking me in my kitchen, faster and faster, until we had a nice rhythm. I could smell the sex and loved the flesh-slapping sounds. His big balls kept slapping into my little balls as he took me from behind, and I remember him saying, “Love fucking your little twat, Lexi!” He kept saying things like that, until he started to say that he wanted to cum in my ass. That drove me over the edge. I trembled hard, my legs almost buckling. I held onto the counter tightly and tried to push back as the orgasm took over my whole body. I was moaning and trembling and twisting, and could feel my tight hole massaging his cock as it contracted involuntarily. I started to dribble on the floor, my flaccid clit flopping around as he continued to fuck my butt. I loved the feel of squirting while he pumped me, my hot, clear fluid wetting the floor and getting under my feet.
He said he was really close and asked if I wanted him to cum in me. At that point, I could tell it was going to happen at any minute unless he pulled out. I started saying things like, “Yesss, Chad, cum in my butt, I want your cum in my ass!” That sent him over the edge. He yelled out a “Fuck Lexi!”, pulled me really tight, and then started to erupt into my backdoor, gushing into me over and over.
I stood in the kitchen, catching my breath, sweating. He did the same for a bit. I pulled up my panties and my shorts, he pulled up his jeans and did his belt. We got our root beers, went into the living room, and watched more Netflix.
A little while later, he said he needed to get home, so we parted ways again, in much the same way we had greeted each other. I went to bed, my pussy filled with his cum, and slept *so* well!
~~~
**I’d love to hear any feedback.**
I also love chatting and receiving PMs!
xx
Lexi
Source: reddit.com/r/gonewildstories/comments/4dhlkq/the_second_guy_ever_to_take_me_his_first_time
What an amazing story and super hot. I am so happy for you Lexi. Also I love how you write and how you let me, your reader, into your life by sharing the phone messages. Chad is right about your ass :)
Incredibly hot and amazing write up. Love the passion you put into the story.
I agree with Chad, you have a fantastic ass. If only you were in the Boston area… ;)
Damn! With as good as this was, I really wanna hear about any and all experiences you have :D
I don’t think I’ve ever seen a [T] story here
I really loved all the buildup. Great story telling, and I hope to read more from you!