Got fucked for the first [T]ime over the holidays. He's [M]arried, and it was his first time with a T. [Part I] | 2016

So in the past I've done a lot of playing with toys and chatting and flirting with men online, but never had quite built up the courage to take the dive into a real life experience. I had a lot of alone time over the holidays and kept thinking about what it would be like to be with a man--really be with a man. If I wasn't toying my ass, I was wearing a butt plug, and I was always thinking about cock, about finally being fucked. A few weeks ago, I finally reached the point where I couldn't take it anymore, and knew I just had to go through with it.

I got all dolled up, and posted an ad on Craigslist along with a few pictures. I showed off my smooth, slender body, my silky, toned legs, and my round, milky-white, girly butt. In my ad, I basically said I was looking for my first experience with the right kind of guy. That I wanted someone who knew what they wanted and would treat me like a girl.

I got a flood of responses, most of them from the wrong kind of guys who can't apparently read an ad. I trashed a ton of them that were asking me to fuck them, or if I liked having my cock sucked. Was I not clear? :)

I narrowed down to a handful of responses that seemed to have been written by more dominant guys who were talking about how much they liked my body, liked my ass, wanted to fuck me, make me suck their cock, use me like a slutty girl, etc. (I got really hot reading some of those!)

I sent a few emails back and forth and found myself really attracted to this married guy. He had a nice body, a nice, thick cock, and was telling me how he'd spent Thanksgiving with his family, but that they'd be away for Christmas. He was bored and prowling Craigslist for some strange. He said the girls were playing games and hard to get, but that he had always been curious about girls like me, and so was just having a look for fun when he came across my ad. He said he'd never done anything with a trans-girl, but when he started looking at my pictures, he could easily imagine himself having a good time with me. (That really got me!)

We started texting. He had a few days to himself, so I could come over. We could hang out and have a few drinks and get to know each other a bit. He said there were things his wife wasn't doing for him, that he was really just looking for a slutty girl who would do whatever he wanted, and get him off really good. He wanted to get rough with me, slap me around a little, spank me, etc. Make me suck his cock, and fuck my ass. He said he was really horny and might want me to spend the night so we could go a few times.

I was so turned on! I was super nervous and trembling, but told him it sounded great and agreed to meet him at his place in less than 2 hours. I just wanted to feel really feminine--and just arranging this meeting was making me feel that way, moreso than I ever had before. I wanted someone else to treat me just like a girl. This guy was saying all the right things. The idea of submitting to his desires while his wife was away was enough to get me out the door, into my car, and driving to his place.

I had on a short skirt that came down just below my ass. It was nice and tight and hugged my butt and thighs really well. Underneath, I had on thong panties. To bring it all together, I had on a white, lacy top with no bra, and 6" high heels. Not really an outfit I'd wear if I were going out somewhere, but I wasn't exactly planning on going out! I put a butt plug in with lots of lube before I left. After I checked my makeup, I was out the door, nervous as hell!

I was literally squirming in my thong the whole way there, loving the feel of the plug inside me, just thinking over and over about the cock I saw in the pics he'd sent, and how soon, I'd be feeling that inside, for the first time.

When I got there, we had a long hug, and he ran his hands up and down my sides and back, and then down over my ass, squeezing it just a bit before giving it an almost friendly pat. Surprisingly, it felt really natural. He told me how nice I looked, and I felt myself answering with a huge smile.

He lived in a really nice place, really nicely decorated, and clean. He smelled really nice, and was well-groomed. Honestly, this was a relief! At that point, I figured I struck gold, because I was honestly worried about what kind of person / place I'd wind up with through a match-up on CL.

Anyway, he was playing some kind of electro-jazz-chill music when I got there, which made me think he just picked out a random station on Pandora. He asked if I wanted a drink, and we sat down on his couch. We started making small talk, and he started sliding his hand up and down on top of my thigh, pausing every so often to give me a little squeeze there.

He knew it was my first time with a guy, and although he'd never been with a t-girl before, he'd obviously been with women (I'm guessing lots of them!), and had told me that to him, I was just a girl like any other. He said he wasn't concerned with that part of me, but was just interested in finding a girl to play with for the night. He said that since I was interested in being a girl, that's why we were meeting. All of this was absolutely music to my ears and had my hole trying to pucker around its plug. Pretty much from that point, I think he had me right where he wanted me.

Anyway, I guess what I'm saying is that he seemed really confident when we met, and could tell that I wasn't confident at all. So we sat and talked a while and had some drinks while he did some light touching until I calmed down.

We eventually started making out. We made out for--I don't know--like half an hour to an hour, and he'd started sliding his hand down the back of my panties, playing with my plug, squeezing and slapping my ass a lot. He kept grinding me through his pants...he was super hard and had a huge cock. (About 7", I'd guess, and really nice and thick!)

He was whispering in my ear about all the nasty things he was going to do to me. At some point, he whispered to ask if I was ready to "slut" for him, and I nodded, whimpering back a soft "yes". We kissed again, and he told me he wanted me to suck his cock.

I felt like my heart dropped into my stomach when he told me that. I was so sure I was ready until he actually said it. Suddenly, I felt nervous, but in a good way, if that makes sense. There was just this crazy, nervous, sexual energy just taking control of me, making me feel like I might do anything. Mixed in with the drinks, and the fact that I was alone with this sexy married guy, exploring my greatest sexual fantasy, my head was really spinning, and I actually started to feel really high. High, as in absolutely euphoric. It was great.

I unbuttoned his jeans, and pulled out a raging boner. His head was swollen up to an enormous size, was wet with pre-cum, and was dark purple. Apparently, I give amazing head. He just did a lot of moaning and thrusting into my mouth and caressing my face while I sucked him, tugged him, and played with his balls. It was all new to me, but somehow, it felt totally natural really quick. Every now and then I'd stop and lick up and down his shaft while I tugged him, teasing around underneath his head with my tongue, slapping his cock up against my lips. I'd work my way back down like that and suck on his balls while I continued to stroke him. Basically, I was doing a combination of things I'd seen in porn videos, and what I thought would feel good. In a few minutes, I felt like a kid in a candy shop and was just going to town on his cock, really enjoying it, getting super turned on knowing he might want to cum in my mouth, but that if not, I was going to have this thick cock fucking me at any moment!

Anyway, he didn't want me to stop. I can tell you this for a fact, because toward the end he started saying, "Just like that, don't stop, baby... just like that..." He kept saying that over and over, moaning really loud while I squeezed and worked his shaft with my hand and sucked and worked his head with my tongue--until he finally lost control.

He groaned, and just kept saying, "Oh yeah... oh yeah... god, yeah..." in this deep, guttural voice while he flexed his hips and pumped his jizz into my hot mouth.

I'd tasted my own cum before, but his tasted a little different. It was super thick, and just really rich and salty. He asked me to show him, and I played around with it in my mouth before swallowing every last drop. He liked that a lot.

After that, we cuddled up on his couch and just talked and drank some more, probably for an hour or so. It might seem strange, but he was telling me about his wife and his kids and random things about his life while our feet flirted around and he ran his hands gently over my sides, sometimes gripping my hips and pulling my ass back into him, and it was just really relaxing. Like, something about it just felt really normal and safe, the way a girl might feel with her boyfriend. I guess it's just that when you meet a random person off the internet, you want to know they're not a psycho. And it was becoming clear to me that this really was just an ordinary Joe-next-door with the wife and kids. He had these powerful sexual urges (as did I!), but after cumming, he had calmed back down and was just being really genuine and sweet to me.

The more I got comfortable with that, the more I could relax, and the more I found myself becoming really attracted to him, and wanting things to go further. That, and by this point, I was admittedly getting pretty close to drunk. I was definitely in that place where rational thoughts had gone quiet, and animal lusts were taking over. If he'd wanted a drunken slut to play with for the night, I was quickly becoming that. At this point, I was starting to feel something completely alien, but amazing. Actual attraction to a specific man, and this growing desire to please him. That might be hard to understand, but up to this point, I'd never focused my fantasies on a specific person, and wasn't sure I could actually feel these emotions toward a man. Was it just the drink? I just wanted him to tell me his filthiest fantasies, because I actually wanted to please him, to see how much pleasure I could make him feel. Is this what it's like to be a woman? I wanted to be his slut, but also, just be his.

Things would soon go further. Talking and cuddling eventually became making out and grinding on the couch. His hands made their way back down the backside of my thong, and he started tugging and toying me with my plug again. I loved the way it felt, twisting around inside my tight hole, the feeling of his hands grabbing my ass cheeks, pulling them open, his fingers sliding up and down my crack, and around my hole, smearing my sensitive areas with lube that was working its way out. At this point I know I was moaning and squirming around a lot, absolutely wanting what I knew was coming next.

He told me that we should go back to the bedroom. He took my hand and led me back to the place where I'm sure he had spent so many nights sleeping with his wife, my tight skirt rolled up over my pillowy ass, my thick cheeks jiggling as I followed him...

~~~

I'd love to hear any feedback on the first part of my story.

Assuming the ratings are kind, I'll post the next part soon!

I also love chatting and receiving PMs!

xx

Lexi