So I have decided that I like posting my personal experiences to Reddit and I will be continuing. So at the time I was still in undergrad (f21) and it was a little while after my pervious post about the hookah bar. I was a little more bold at this point but still a little on the shy side. I was still trying to learn what I liked and who I liked in a sexual sense.

Start of Spring semester I had the pleasure of meeting a guy in one of my classes who I got to know better then became friends with. One night we are hanging out and the topic gets to sex which isn’t surprising considering we were getting wine drunk. He then tells me about how he is bisexual and that he went through what he called his “Man Phase”. He then detailed some of his sexual encounters and how some of them almost became full blown romances. He mentions that when he was feeling horny some nights he would go on Grindr and could find someone to spend the night with extremely quickly. I was intrigued because on Tinder and Bumble it can be quick but not as fast as he was describing. He then talks about how in his opinion bi-guys are the best lovers and they are always down for three way. Ignoring the blatant generalizations of bisexual men I was still curious. He then says that is where a lot of transwomen are at because it’s a far more tolerant dating app; I didn’t know it at the time but this would be important later. I take this information and sit on it for a while.

One night I was feeling especially horny and I just didn’t know what I wanted. It was too late to set up something using the traditional apps so I reached into my night stand to get my vibrator out and finish that way but I remembered what I’m my friend told me. So I picked up my phone instead and downloaded Grindr. I made an account filled out the information then put some pictures that I liked on it. Barely any time passed after the photos were added before I got a notification. Some guy messaged me asking if I wanted to meet up right now. I checked his profile and he didn’t have his face in any of his pictures but he was fairly attractive, slim build, defined muscles. I messaged him back saying that I was down to meet up now depending on what he had in mind. Barely a moment went by before he said that he was down for anything and asked if I wanted him to come over to my place, do it in his car, or come to his place. Now normally I wouldn’t meet a strange man from the internet in the dead of the night for sex for obvious reasons but I was not thinking very clearly at that moment. I didn’t feel like having car sex and my place has a roommate who will judge me so it had to be his place. I messaged him and he gave me an address. I got myself put together and luckily I had the sense to grab some condoms. I get in my car and make my way to his apartment, it’s in a nice area of town so I felt a little safer. I get to his apartment number and knock on the door. He opens the door and finds me a curvy petite woman in old stained sweats with hair that was thrown into a pony in the dark (real sexy stuff right). Him on the other hand, he is wearing a tight shirt and some designer sweat pants that fit him amazingly, his hair looks like he styled it right before I got there. He invites me in and asks if I wanted anything to drink, I declined but I did sit down on the couch. We made some chit chat and he then asked if I wanted to move to the bedroom, I agreed and he let me to the cleanest bachelor bedroom I have ever seen. I sat on the bed and he asked me if I liked music on which I said “why not”. He then asks me if I would like a sensual massage and being in a “why not” attitude I agreed. He asks me to remove my top which I did and he was all compliments on my body. He said that my figure looked amazing and that I had lovely boobs. With me sitting on the edge of the bed and him behind me he starts rubbing my shoulders and back which felt amazing. In my mind I was thinking “finally a man who gives a good massage before sex”. After a while he gets close to me and I didn’t notice that he had removed his shirt too, his chest pressed against my back felt so warm and nice. While pressed against me he starts massaging my chest and teasing my nipples every so slightly while his breath runs against my neck. This is the moment when the juices start flowing and I’m getting into it. My tummy tightens and I feel my skin get warm and feel like electricity is running through me.

He then takes this opportunity to start kissing my neck and really put in the work for some quality foreplay. We make out and he plays with my nipples more, gives them playful twists every now and again. Finally he decides to make his move comes around to stand in front of me. He kissed me deeply with a lot of tongue (but in a good way). He then asks me if I would give him oral. I pull him close and pull down his pants to reveal a pretty average penis and honestly I was not disappointed because his grade up till now was A and I’m a firm believer in skill beats size any day. He gives some great vocal moans and politely asks if he can put his hands on my head. I agree and he starts to guide me up and down. After a while he starts to say he is close and let’s go of my head but I want to be nice and reward his awesome massage so I let him finish in my mouth. He said that I did great and that he wants to return the favor. He pushes lightly on to my back and starts to pull my bottoms and panties off before he gets them to my knees and stops.

So here is where I get clued in to the fact that he thought I was one of the most attractive transwomen he had the pleasure of meeting. His comments through out the night started to make sense. Embarrassed i then explain that I was really wanting to be with a bisexual man because I thought it would be fun to try. I go on to say that he is one of the most tender male lovers I have had so far. He and I laugh about the situation. We sit on the bed now both naked talking and he explains that he wanted to see if he was attracted to transwomen because in his words they are the “best of both worlds boobs and penis”. We talk for a little bit before he asks since the moment was ruined if I wanted to take off. I say I’m still game if he is, he then asks if we could change things up a little bit. He then asks if I would be ok topping, which he explained that he wanted me to wear a strap-on and go to town on him. At this point I had very done this so I said yes and explained that I was new to this. He goes and gets the toy and helps me put it on. This toy is apparently a really nice one because not only does it have something for him but me too. One end goes in me and the other end for him with a strap to hold it in place. He then gets everything lubed up and in place, with him being taller than me he suggest we do it prone which I agree. I guide it in and push into him as he lets out a moan, the vibrations of my end give me a really nice sensations. I start to move my hips and I get into it, honestly it made me feel powerful and just a little bit envious of people who have penises. That feeling fucking someone and being the penetrator was pretty awesome. He had me spank him, pull his hair and generally be rough with him. I got super turned on seeing a man squirm under me. Eventually once I got the hang of things we switch positions, finally we landed on cowboy (not sure if people actually call it that when a man is riding). That position got us both going he was moaning super hard and I was getting into too because my side of the strap on was hitting the right places. I’m a quiet person but see him bouncing on me got me into the dirty talk. Soon he got to the point where I knew he was about to burst again, I moved my hips a little more till he burst. He covered my stomach with his cum and collapsed on me panting, I finished too when I saw because honestly it was super hot, it may not have been the hardest orgasm I have had but one of the most fun I had to that point. I moved my hips a little bit because he would squeak since he was so sensitive. We made out a little bit, before I got up and got dressed. I went home and I remember feeling very pleased with myself. I got to have sex with a bisexual man just not in the way I thought I was going too