For privacy purposes, their names are Valerie (35TF) and Elliot (32TM) who is a slim, 5’7, chicano transman with a country/southern accent who is clean shaven facial hair wise with short/medium dark hair. It’ll also help to read what happened between me and Valerie for a backstory. Also, this is a warning for accidental front hole use.
So after that night when Valerie and I had sex, we continued to do so somewhat regularly whenever we saw each other. We had a routine where I would eat her out and then she would either ride me or be spoon-fucked until she would cum except I became more dominant in eating her ass to where I would make her cum from that in which she would complain about me not cumming since I would stop when she would orgasm as she had to push my face away from her ass because of how good she felt and just continue on with our night. One night,she came twice from riding me with the second time being at the same time as me. She said that she needed a cum-catcher as she told me that hers is nowhere near as viscous as mine in which I mentioned having a threeway to do so as long as he’s the only one getting attention from her since I won’t say no. She followed through on that.
Two weeks went by and I was hanging out again with her and some of her friends. She then tells me and points out Elliot. She reminds me of the conversation we had since he and I had similar views if we were to have a threeway which she also tells me that she’s surprised he’s comfortable enough since he is straight and usually has a hard time being comfortable around straight cis men. I also was told that for tonight that I would have to wear a condom for his comfort despite me only having sex with her and that I can touch him in terms of positioning/communication purposes. It was interesting that despite talking through the night and being friends already, he and I never talked about it.
So after a little bit of drinking and talking with her friends, the three of us ended up on the couch at her place. At some point the conversation turns in which he and I briefly exchange glances as if we were in sync which she starts making out with the both of us and we head to the bedroom. I noticed that as we were undressing, he would nervously look at me, especially around my dick. He had on compressed boxers which I only saw from the front, and a black tank top on as well. At one point I was standing behind her kissing her neck and playing with her boobs as she pressed her ass against my dick and then trying to move the head of my dick against her asshole while he was on his knees and sucking her from the front. It was the first time I also saw her dick since she usually covers it. While she’s still standing, I tell her to hold open her ass so that I can eat it. So I kiss my way down her back to it and while he was blowing her, I was able to reach around and grab his face to make him deepthroat her.
After a little bit of that, he mentions that what I did was hot as she talks about wanting to ride me while he sucks on her. As she puts the condom on me, his eyes briefly widen in surprise or fear. As she sinks down on it and looks at him and says “He doesn’t want to see this, so make it disappear in your throat. He responds with, “Yes ma’am” as I can hear the rhythmic clapping of her ass on me with him getting his throat fucked while his hand is on my chest sometimes to keep himself balanced. She stops him since she was about to cum and tells him to just stroke her. He pauses to breath and looks at her and then looks at me and says for me not to be weird or freak out. He takes off his shirt, boxers, and socks and thats when I was able to see his body. I found out that his cup size is AAA, so to him there was almost no need for top surgery. For someone of his build, he is slim all around except that his ass is really round to where it almost seems like it belonged to someone else considering how well he hides it with clothing and it jiggles. All of the hair he had on his body was only around his ass and armpits. As he’s about to continue what we were doing, I tell him he can sit on my chest so that she can fuck his throat. In which he awkwardly, but more comfortably thanks me and gently, but quickly sits on my stomach instead and I can feel how wet and warm he is as he makes out with her at the same time since he can’t reach her dick as she’s now leaning back with her hands on my legs supporting herself.
As he is kissing her and stroking her, he progressively moves his ass toward my face leans forward trying to suck her as she’s slowly riding and with him exposing his really hairy, pink, puffy/meaty asshole which was very tempting and inviting. I stop and ask him how he would feel if I just ate his ass in which he takes a second to process, moves to where his hole is right over my tongue and says, “I’ll just have to find out how I’ll feel” and then presses his weight down on my face while letting out a moan. I also noticed that his smell was different, not in a bad way, than what I was used to and the shyness he had instantly went away as he started dirty talking. What I remember the most is that while he turned his head to face and try to look at me while lifting my head up to his ass as he grinded his asshole back against my tongue as if his ass was fucking my tongue “I can see how horny you’re getting as you’re fucking her ass while your chest is getting soaked from you just eating my ass. Sadly, the most you’re allowed to do is eat my ass, but if you keep this up, I’ll let you rub that dick against mine until I cum as she has told me stories about what that dick can do. This was good as Valerie was getting tired physically. Part 2/3 will be the next post due to length
Source: reddit.com/r/gonewildstories/comments/waoxoe/group_mtftm_my_first_threesome_with_a_trans_man
Next part asap