u/NYbiguy88

For context, I am a "straight" 37 year old man. I'm not getting into it really but I have hooked up with a handful of guys over the last 10 years, I can count on one hand. I'm what you'd call "vanilla" when it comes to gay hookups. My wife and I have a great marriage and a great sex life.

Why do I do it? I don't know, primal urge maybe?

Anyway, I finally give in to finding a smoking hot Trans woman online. I was searching online for weeks looking for the perfect one. Perfect tits, nice cock, great ass and beautiful face. The absolute perfect creature. "Okay this is it, I am doing this". I call Jenny, she even sounded sexy. I Ask to FaceTime verify it's actually her in the pictures, she happily obliged. We agree on a time and she texted me her location, it was a Hyatt about 15 minutes from my house. I'm working from home and had some time, wife was at work and kids were in school. This is it! the perfect storm to get away.

The whole drive there I'm amping myself up, trying to work out the nerves. Once I parked, I texted her to let her know I've arrived. she replied with a room number. "Shit" I thought when I saw the main lobby. Two receptionists and some guests mingling around. "Gosh I hope no one tries to ask me where I'm going". I make my way through the doors and as I am walking, one of the ladies behind the check in counter ask "Can I help you?" I reply very confidently "I'm visiting on old friend who's in town" and they tell me "elevators are to the left". "Phew, I'm good to go". I didn't know her last name or if Jenny was even her real name.

By the time I get to her room, I am ready. I have waited so long for this. I deserve this. I knock twice and I hear "coming!". She opens the door in a bathrobe and holy shit, she is hotter in person. An absolutely gorgeous smile, warm welcoming persona. I cant wait to get my hands on her. I would guess she was 5'6, 5'7, 140lbs. Long shiny brown hair almost down to her ass, which was perfect by the way. And perfectly shaped C-cup tits. We introduce ourselves and she asks "Is this your first time with a woman like me?" All I could say was "yeah" as I was now staring at her open robe. She throws her robe to on the chair, lays on the bed and asks "you like what you see?" as she's rubbing her cock with one hand and her tits with the other. I'm in a trance, at this point I would do anything she wanted. She told me to take off my pants and shirt and signals me over to the bed with her finger. She rubs my dick on top of my briefs and comments about the size. I have a 6" cut, nothing major. She pulls my waistband down and pulls it out. It felt heavy in her hand. She gives it a lick at first then starts taking me in her mouth. After a few minutes thats when she asks me if I want to suck her, and yes I did! We 69 for a while, playing with each other's asses, both our cocks are rock hard. I can taste her precum. I start giving her the corkscrew wrist motion while sucking (which makes me wild when its done to me) and she stops me and says "I don't want to cum yet" I didn't want her to either.

She hops off the bed and pulls me to the edge. Puts a condom on and pulls lube out of the nightstand. I'm thinking "wait a second, this isn't supposed to happen, I was planning on it being the other way around". To be honest, I didn't care. If I was going to be topped for the first time it might as well be by a smoking hot trans. She put my legs over her shoulders, teased my hole with her tongue and tip then slowly slide in, gently. My wife and I occasionally use toys specifically anal toys so this isn't anything THAT new but definitely a step up in size. The smile she had on her face when she finally made it in balls deep was angelic. Slow, long thrusts and my ass finally relaxed and "accepted her" as she put it. It went from slightly painful to total euphoria. I couldn't believe that this was actually happening. Her cock felt so strong and the fit felt perfect. Her hands stroking me and her soft long thrusts were totally in sync. Oh my god it felt so good. Too good. I muttered out in "I don't want to cum yet, oh my god keep fucking me" I was moaning like an absolute slut. It felt so good to submit and let this gorgeous person have their way with me. Her whispers of "cum for me baby, let me see that cum" as she was stroking me finally got to me and I exploded in her hand, blowing my load all over my self. It was so hot, I can still see her face when I finally came.

She stood there, still inside me while I was processing what just occurred. She let me breathe then pulled out of me. She asked me if I wanted to clean off before heading home to my wife (I was wearing my wedding band). I said "yea of course". She walked into the bathroom, I thought she was getting a towel or something and this was it, thenI heard the shower turn on. I hear a "are you coming?" I didn't really want to move but I wasn't passing up the opportunity to shower with her, plus I wanted her cum. The shower could definitely fit more than two people so there was plenty of room for us. I walk in the bathroom and she's already soaped up and started washing me once I got in. Once all soap was washed away we start kissing and she goes back down on me! I couldn't believe it. She stands back up and starts kissing me and tells me to get down on my knees and "work mommy's cock". I start sucking her, back against the wall she's fucking my mouth like she fucked my ass. "I'm close baby, you ready for mommy's cum". I feel the twitch snd she buried her cock down my throat and shot ropes. She was so far down I barely tasted anything. When she finally let off me, I sucked her until she went soft. After some more kissing we dried each other off and got out. I got dressed, went to say goodbye and she pulled me in a for the hottest longest kiss you could imagine and told me she'd let me know when she was back in town and showed me the door. I slipped out a side door of the hotel and headed home. I cannot say how much I needed that and I highly recommend trying it. It didn't go as I totally expected but am so happy with the way it did.

36 [M4A] Eastern Nassau Anyone in the Seaford/Massapequa area able to host a bj swap tomorrow morning around 9am? Pictures on my profile. All are welcome.