My first time with a tgirl [MT]

This happened over 10 years ago after I had dropped out of college and was trying to “find myself” so the details are hazy, but I wanted to share it because I still think about it to this day. I still jerk off thinking about how hot it was.

Some backstory… I grew up in a pretty big city (I won’t tell you which one). After high school, I went to a state college that was about 3 miles away from where I grew up (I wanted to be a teacher… I didn’t become one, but that’s a different story) and my dad died suddenly when I was 21. He was diagnosed with cancer and the doctors said he had a really high survival chance but he was one of those weird cases where he suddenly died about two weeks after the diagnosis for what seemed like no reason. I’d gotten about $30,000 from his will when he died and just didn’t feel like working or going to school. I was really lost.

I was living in a crappy converted garage in the backyard of a house near where I grew up and I started going to a shitty bar down the street regularly. Regularly = like 5-6 times a week, sometimes at night, sometimes in the afternoon as soon as they opened. Most of the time I was the only person in there under 40. The night bartenders were smoking hot girls in their 20s, most of whom were from Mexico or Central America. But the afternoon bartender during the week was this sexy middle-aged woman named Marisela. She was from Mexico and had these big fake tits that were always just like an inch away from popping out of her tops. For a visual idea, her and Vanessa Jhons had a similar look, although you never would have confused them for each other.

To be fair, I’ve always had a thing for Latin MILFs with big fake tits ever since my friend’s parents got divorced when we were in high school and his mom went to Mexico and got these big DD implants. She started wearing low cut tops and tiny bikinis at the beach and it was so hot. I think maybe she was teasing us. I know he hated us talking about how we wanted to fuck his mom all the time. None of us ever got the chance. Back to the story.

I was instantly turned on by Marisela, but I could tell she was keeping me at arms length. However, she smoked about a pack a day, and I smoked as well, so we used to go to the side patio and smoke and chat. We got friendly but every time I tried to hint at taking it beyond friends or get flirty, her walls went up. Other guys hit on her in the bar and she would brush them off as well so I figured she was either married and not telling anyone about it so she could get bigger tips, or she didn’t date customers.

After a couple of months, I had resigned myself to thinking about fucking Marisela while I masturbated. I thought nothing was going to happen with her anyways, and I was occasionally hooking up with girls so I thought it was best not to pursue her anymore lest I creep her out and get myself banned from a bar I could walk to.

However, something changed, and to this day, I’m not sure why it did. She lived in the same apartment complex as one of my friends and his family. I used to see here there every so often. A couple months after I figured I was just going to be jacking off to her for the rest of my life, I went to a birthday party there and she was there. I will never forget the sight of walking in and seeing her drinking out of a plastic cup. We started talking and her and I went up to her apartment a couple of times for smoke breaks because she had a balcony. During one of our smoke breaks, she was leaning against the balcony railing and there was an awkward silence, and I reached over and grabbed her hand. She kind of looked at me out of the corner of her eye and smiled, then she pulled her hand back and said something about me being so much younger than her. I told her that didn’t mean anything and she told that she’d had a rough time with dating and she didn’t think I’d stick around. I kept pushing her on it, saying it could be something good, and she kept saying I wasn’t going to stick around, and we went around in circles like this, blah, blah, blah, until she was finally like, “If I tell you something, will you promise me you won’t tell anyone else?” I told her yeah, and she made a very big deal about me promising not to tell anyone, making me promise repeatedly not to tell because she said it would ruin her life. She took me inside then and had me sit on the couch and she sat next to me, and looked me in the eyes, and said, in these exact words, “I’m a tranny.”

I had no idea what that meant. She had to explain to me that she had a penis and that us doing any sort of dating would mean I had to be OK with that, and then she stressed again that I couldn’t tell anyone about it.

I need to add at this point that I had no idea she was trans, and I’m almost certain no one else who went to the bar knew either because no one ever said anything about it. And this was back in ’07-’08 when people in a local bar would have said something about it. Marisela did have kind of a raspy voice, but it was the kind of voice you would associate with a heavy smoker. She didn’t have a visible Adams apple, and her hands and feet were kind of big, but not anything out of the ordinary for a woman. I’m just relaying this to let you know how completely shocked I was when she told me.

I remember being silent and staring for a while. She said, multiple times, “It’s OK honey, it’s OK, honey” and “It’s happened to me before. Don’t worry.” She was so vulnerable at that moment, and I could tell she was very afraid of the way I would react, and there was an openness in her big brown eyes that just drew me in, and I leaned in and kissed her. She kissed me back, grabbing the back of my head, parting her lips and accepting my tongue into her mouth. I was so turned on. We made out for a while on the couch, me grabbing those big fake tits I’d been dreaming about for so long, pulling her shirt down to get at her big brown nipples, feeling her cock get hard inside of her jeans, her reaching into my pants to rub my hard dick… then she told me to wait a minute and she got up and closed the blinds, then told me to get naked and went into the bathroom. When she came out, she was totally nude, her hips swinging and her soft little cock bouncing side to side, her big round tits drawing my eyes.

I was rock hard, and she came over to the couch and sat on my lap, facing me. She leaned forward and kissed me, deeply, then reached down and grasped both our cocks in one hand, stroking them together. I was sucking her tits, grabbing her ass, kissing her like I was crazy — the way you get when you’re so turned on and you just want to fuck. I kept trying to get her to stand up and move to the bed, but she just kept calm and wouldn’t move off of me so we could go to the bed. Finally, she leaned in and whispered into my ear in the hottest, sexiest voice I could ever imagine, “You can play with my ass.” She had a big, tight ass, and I was spreading the cheeks already, and she reached back and guided my hand so that my middle finger was touching her tight hole, then she let go. I moved my finger around her little asshole, feeling it give as I pressed on it, trying to get my finger in, but I could really only get the tip of it in because of the angle. I’d never had a girl who let me play with her asshole before, and I was so turned on. I’d always wanted to fuck a woman in her ass, but I’d get a “No” everytime I brought it up.

Finally, Marisela stood up, grabbed me by the hand, and led me to the bed. I grabbed her cock as we laid down on the bed and stroked a little bit because I was curious what it was like. We kissed for a few moments, then she moved down the bed and took my hard cock in her mouth. I felt the moist, soft heat of her mouth enveloping my erection, and I felt it hit the back of her throat before she let my cock slide out again, making eye contact with me, then bobbing her head to take my cock back in again. She stroked with her right hand while she worked my cock with her mouth, taking me in and out, in and out. Her blowjobs were so good that they will always be what I compare every other blowjob too. The best comparison I can make is that it was like getting a blowjob from a pussy. I never felt her teeth once, and she was able to cradle my cock with her tongue in a way that was just mind blowing. Most women I’ve been with are either just OK at blowjobs or can do well in only one position, like on their knees and you’re standing up, or when they’re perpendicular to you, or when you’re 69ing, or when you’re laying on the bed and they’re sucking you looking into your eyes, etc.. Marisela was so good at sucking dick in any position that she could get me cumming in under a minute regardless of what angle she was at. We went camping one time with some friends a few months later and she sucked me off so quickly in the tent that no one had any idea it had happened.

At this point, I was on the edge of cumming, but I wanted to fuck her, so I gave her the standard pull on her shoulders and she stopped sucking me and asked “How do you want me?” I told her I wanted to look into her eyes as I fucked her, and then I asked if she had any condoms. She said no, but that she was clean. Now, it turned out Marisela was clean, and I didn’t have anything to worry about. However, with the wisdom of age, I know I should have insisted on using a condom. It’s just too dangerous to have unprotected sex with someone.

Marisela pulled a bottle of lube out of her night stand, then laid on her back and lubed her asshole up, holding her balls up with one hand while gently inserting a finger with the other, then she reached for my cock and rubbed lube on it, pointing my dick in the direction of her hole.

The first time, I went in way too fast and she gasped and closed her eyes in pain. I’d never actually used lube during sex before, so I had no idea how fast it would go in. I asked her if she was ok, and she said “Yes. Go slow. It’s OK honey.”

Fucking Marisela’s ass was amazing. I slid in balls deep and closed my eyes, luxuriating in the feel for a moment. I started thrusting slowly and she began moaning, running her hands down my chest and sometimes grabbing my butt and holding me deep inside her while she bit her lip. She loved talking dirty, which made it even hotter. She’d say things like, “Fuck my ass, papi” and “Soy tu puta (I’m your slut)”. I almost came too fast because it was so good, then we switched positions so we were kind of scissoring because she told me it would keep me from cumming and work me back down from orgasm. Then, I got her in doggy style. I reached around to stroke her cock, and I was surprised it was rock hard with a long rope of precum hanging from it. She was moaning, and I was alternating between squeezing her tits and stroking her cock, when she started contracting her sphincter muscles and tugging on my cock with her ass. I nearly exploded right then, but I knew I wanted her to be on her back when I came, so I flipped her around and laid her on her back. At this point, I grabbed the bottle from the nightstand, lubed her cock up and started jacking because I really wanted her to cum with me. It really didn’t take long. I fucked her in missionary for maybe another 2-3 minutes, and she started cumming, spurting cum all over her chest while she moaned and arched her back, while she started milking my cock with her ass again, which just sent me over the top. I slammed home deep inside of her and just filled her full of cum. She kept milking me with her ass, pulling, every last drop out of me and we kissed long and deep, both of us breathing heavy.

That was our first time together, and we stayed together for almost a year, until the age difference got to be too much for her and she broke it off. I stopped going to the bar for awhile after that… didn’t call her either. I finally went back to the bar a few years later, hoping maybe she’d be working and we could catch up. She hadn’t worked there in a while and I tried calling her later in the evening but her phone number didn’t work anymore. I talked to my friend who’d lived in the same building as her about it, and he told me she’d moved a couple years ago but he couldn’t remember where to. I wonder sometimes what she’s up to and if she’s alright.

Source: reddit.com/r/gonewildstories/comments/c16okk/my_first_time_with_a_tgirl_mt