[M/F] First Time with a Transgender Woman

TLDR: My tinder date had more than I expected, I didn’t stop.

–This is my story from college last year. I’m reposting because I don’t have access to my old account, I want all the people who followed me to be able to find me!–

Hello everyone, I am 24 and not exactly sure what I’m into. I always thought I was straight into cis women exclusively then I met a beautiful woman who happened to be trans a few years ago. I had no idea which to me at the time was surprising, I always thought you could tell, either from the body type or the way of speech. This experience really confirmed to me that trans people are the sex they identify as. Anyway, the date went really great! We went ice skating and to dinner and had a great time talking. Definitely my best tinder date ever haha.

After dinner we were holding hands walking back to my car and when I opened the door for her instead of getting in she turned to look at me, tell tale kiss me sign, so I did. And we were heavily making out in a maggianos parking lot lol. She broke off the kiss and asked to get into the car so we could talk. I assumed she wanted to go to one of our places to have sex.. I was right but that’s not what she said.

She explained to me that she was not born a woman, she did not have all the “Parts” I was expecting but wanted to be upfront with me. She didn’t expect to get to the point where we would be naked so she didn’t feel the need to disclose it before the first date. I understood that. Honestly I may have unmatched her due to my preconceived notions about trans people. I do appreciate her telling me now, it definitely would have been a shock for me to undress her and a hard cock to have fallen out lol.

She asked if I wanted to end the date and I thought for a few moments. I had a great time. She was awesome. We connected and had a great conversation, should all that go to waste because of a penis? 

I let her know that I didn’t want the night to end but also that I’m not sure how my body would respond. I’ve never been with a man or a trans woman before, before this night I never had the desire too, I have no idea if we will be sexually compatible. But I wanted to find out.

She was THRILLED I said that, very touchy feely in the car on the way back to my college apartment. I glanced over at her waist every now and again and never saw anything that looked like a dick. I was surprised because I was hard the entire time, I figured she would be too.

We got back to my place and chilled and talked with my roommates for a few minutes. They were in the couch so we took the loveseat, she sat on my lap and shook her ass on my hips multiple times, I was embarrassed at first but damn did it feel good. I’ve never been an exhibitionist at all but over the years being watched is so hot. I’m not shy about my body or my nudes and when I find the right partner I want to go to sex clubs and make amateur porn.

As soon as my door closes she is on me, she takes control and makes everything about making me comfortable and aroused. Kissing me biting my neck and ear, moving her hands all over my body. My clothes are gone before she even takes off her shirt. All worries about me not being able to perform vanish when I see her get on her knees, those beautiful blue eyes of hers, ugh I’m horny just writing this now! She grabs my cock and licks me from the base to tip. RIGHT there is how I knew I had been missing out sexually for so long. I got the best blow job of my life. Every cis girl I had been with prior seemed to do it to reciprocate oral, she did it because she desperately wanted my cum down her throat. 

At the time I masturbated more than I should and even though oral felt amazing I didn’t often cum from it. I told her i probably wouldn’t cum after several minutes of her almost deepthroating me (no one ever has ): ) and she was DETERMINED. she pushed me back onto my bed and knelt again in front of me, this time lifting a leg onto her shoulder. She began jerking me off and knelt lower, sucking on each testicle before I felt her tongue dance across my asshole and for the first time ever I moaned sexually. It felt fucking amazing. She alternates back and forth between licking around ass, putting her tongue inside me and sucking the head of my dick. I had my eyes closed, I was in heaven. She was definitely going to make me cum, I didn’t want to because I didn’t want her to stop.

I felt something on my ass, I thought it was her cock but realized it was a finger, she teased me some more and I told her to put it in me. The feeling was intense. She massaged my prostate and my body fucking shook as I came. By far the most intense orgasm I ever had, I felt like I emptied everything I had into her hand and mouth. She quickly got on top of me and kisses me aggressively. I never tasted cum before and honestly it wasn’t bad. Not great but not bad and I was too horny to care. We just made out for what seemed like hours.

Usually after I cum I’m spent, I lose all horniness. Not tonight. After cumming and tasting it I wanted more of her and it was my turn to take the lead. I undressed her and this was the only point I was nervous, all this time she was focused on me. I hadn’t touched her, I haven’t tasted her. What if I hate it? What if I’m not turned on? I worried about disappointing her. But I kept going. When she was only in her panties I finally saw the outline of a cock. My mouth dropped and she chuckled, asking if I liked what I saw. Her body was perfect. I kissed her again and reach down and ran my hands over her panties, I felt her cock twitch and right then I knew I was into this. 

The first time I touched a dick other than mine I was surprised, it was warmer than I thought it would be. Really soft yet incredibly hard. Idk why this was so surprising I feel mine all the time haha. I knew I couldn’t reproduce the oral she gave me but I tried my best. I wasn’t great and she gave me pointers, what to do with my tongue how to avoid teeth. She wasn’t very big at all so after some practice, and gagging, I got her cock all the way in my mouth. I moved my hands all over her body, grabbed her breasts, choked her, teased her ass. I flipped her over next, I needed to taste what I was going to fuck. 

I was surprised I wasn’t grossed out or nervous at all I was just so fucking turned on. I tasted her ass and really enjoyed it. Jerking her off as I pushed my tongue inside her and moved it around. I replaced that with a finger, then 2. She was a moaner! Luckily I had lube, I tried that instead of lotion when I masturbate and I really prefer that feeling, if you have a penis you should try it!

I lubed up her ass, put a condom on then preceded to have the best sex of my life. Of the positions we did I loved missionary the best, being able to kiss you as we have sex is my favorite by far, it’s so intimate and romantic! We finished in Cowgirl and that was amazing. Watching her cock flop as she rode me was so fucking hot. I started to jerk her off and she told me she was about to cum, I leaned my head up and stuck out my tongue and moved my hand faster. Unfortunately it didn’t reach my mouth, I made up for that by scooping up what I could and brought it to my mouth. Apparently diet really affects semen because wow she tasted a lot better than me. Seeing me did this mush have drove her wild because she really aggressively started to ride me. Slamming her hips down into me to get me deep inside her. She leaned forward and kissed me as I came inside her. 

I just came twice and I was still horny!!!! I asked her to fuck me when she was hard again, I never thought I would say the words “please fuck me baby” but I NEEDED her cock in me. Unfortunately she said she didn’t like to top and I left it at that although I was disappointed. We cuddled for the rest of the night, I woke up in the middle of the night, went to the bathroom and I was crazy horny. We both were sleeping naked so I got between her legs and took her soft cock in my mouth. We had sex again this time exclusively in prone and that was just so primal. She said she was clean and said to just fuck me but I have such a fear of STIs lol. I always use condoms except if we are in a committed relationship, I did not last long this time.

In the morning we said our goodbyes and said we would set something up again. We never did. She really didn’t like that I wanted her to fuck me and I never saw her again. I was upset, the sex was mind-blowing but the date was perfect, I would have loved to have dated. Anyways, after that I wanted to explore more sexually. I found out I love my ass getting played with. I bought toys. I haven’t found another trans woman I have a connection with so no more sex stories there. I want a cock inside me so fucking badly. So I started looking into men. I was never anti gay sex I just was never attracted to men. I sexted plenty and was always so turned on at the sight of a hard cock, thinking of how I would make them moan when I suck it or how badly I’ll tremble when it’s inside me.

Every single time though when it came to the date or the hookup I would get so nervous. The same nerves I got when SHE first told me she had a cock because I wasn’t sure if I would respond sexually and I didn’t want the awkward, hey I’m not sexually attracted to you talk. So I never actually had anyone over or went on those dates. I think I would love it, turn into a little dick slut lol if I just push myself and do it like I did with a trans girl for the first time.

I figured the best way to try it out would to find a cis girl to peg me as I haven’t been able to get fucked by someone with a cock yet but every girl I’ve connected with since has been extremely submissive!!

So I’m unsure of what to do. I’m turned on when I flirt with men, I get hard and sext plenty. I get off at the thought of being pinned down and fucked but I can’t bring myself to actually invite someone over or go on a date. Is it the thought I just get off to? 

Did this date with her and the night make me realize I’m bi? Pan? Am I just straight and into girl penis? Anyone ever been in a situation like this? It just seems so unique and weird and idk what to do. It feels like the obvious answer is to just keep looking until I find a woman to fuck me, either with a strap-on or her dick but I can’t help but feeling I’m missing so much sexually that I would enjoy if I just could calm my nerves and date/hook up with a guy.

Well this was a novel!!! I’m sorry I hope this belongs here. I didn’t mean to go so in detail with the sex but I’m so horny thinking about all this lol.

If anyone has some good advice after dealing with their own sexuality could you kik me (bep.2014) and give me some advice on how to sort out actual feelings from just horny lust?

Source: reddit.com/r/eroticliterature/comments/m6igw9/mf_first_time_with_a_transgender_woman