Long time lurker, first time poster, etc. This is a story about one of the hottest things that has ever happened to me.
I know you guys tend to like descriptions, so here:
I’m a trans man, on HRT but still pre-top surgery. So I look fairly masculine but I have something like 32C tits and, if I crossdress, I still look pretty fucken’ hot. I’m about 5’3″ and petite. My finace is tall, handsome, slim while still having muscles, and has a big dick – 8″ and wide, it’s an effort to get it into me sometimes. Anyway. Storytime. If you want to skip directly to sex stuff, go to the second bar in the text.
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I was visiting my fiance (we’ll call him Alex) over Christmas break, but he had to go back to work after New Years so I was sitting home a lot with nothing to do. One day, fairly horny, I decided to dress up and surprise him when he got home. I started playing with myself, decided I *really* wanted him to fuck my ass, and made sure everything was clean back there and stuck my plug in for him to find. I showered and shaved so I was all smooth and nice for him, then started getting all dressed up.
Crossdressing is something I do for mostly sexual purposes sometimes, because I still have old girl clothes and they look good on me. So I pull out some of my old lingerie – a black lace thong and lacy black pushup bra – and pair that with some sheer black thigh highs with lace bands at the top. The thong barely covers the head of my plug and the bra makes my tits look amazing. Finally, I pull on a dress – skin-tight and fairly short, black and white striped, with sheer black material covering my back and the top of my chest. It goes up to my throat with a little collar of the striped material there, so it looks a little bit like a collar and I like that. Regardless, I look like a whore. Finally, I pull on a pair of heels – mostly for utility. Alex is taller than me, so if he bends me over he usually has to bend down a little to actually fuck me, and I was hoping that the heels would solve that problem. Also, they make my ass look great.
I waited sort of nervously for him to come home. I knew he’d like it, but I was still wondering how exactly he’d react given that I don’t really do this often. I play with myself a little while I’m waiting – move the plug slightly, touch my clit. I’m already soaking wet just thinking about him. Finally, I hear him at the door. He comes in, drops his bag, and then walks into the kitchen to see me.
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Alex pulls me into him and starts kissing me and moves his hands down to grab my ass. We both decide to move to the bedroom. He and I kiss a bit more, then he tells me he wants me on my knees. I drop down and unzip his pants to pull his cock out and start sucking him off, deepthroating him and letting him fuck my face. I had to practice for ages to be able to take all of him in my mouth, but now he can grab my hair and pull me on and off his cock, which I love. At some point, he gets impatient and pulls me up, turns me to face the bed, and pushes me so I’m bent over the bed. Quickly, he pushes my skirt up and pulls my thong down – and then he finds the plug that I left in for him. He pulls it back and forth a little and I moan, but doesn’t immediately decide it’s an invitation to fuck my ass; instead, he thrusts into my pussy. It’s a little fast for how large he is, and I try to lean away but am already pushed into the bed, so I take all of him in one movement. Even though I was playing with myself earlier, he still feels so huge inside me, but I want him to use me so I don’t try to slow him down. (Side note: the heels fucken’ work. I’m exactly the right height bent over.)
He fucks me fast and hard, grabbing my ass and occasionally sliding a hand up my dress to run his nails down my back. At one point he grabs my tits and pulls me so I’m standing with him still fucking me, my head turned back a bit so I can kiss him. Finally he pushes me back down and is leaning over me. He asks if there’s anything in particular I want. I’ve admittedly gotten to the point where talking is a little difficult, but in between moans (I’m noisy, sorry neighbors) I tell him he can fuck my ass if he wants.
Now, it’s important to note that while I did fuck my ass with a dildo earlier, I’m not really warmed up. I’m expecting him to go slow and use lube. He sort of missed that memo. He pulls the plug out of my ass – I moan again – and then he starts to slide into my ass right away, with just how wet he is from fucking me as lube. Again, I try to lean away or slow him down, but there’s not really a place I can lean to as I’m pushed into the bed. I slow him down a little, but it’s going much smoother than I expected – my earlier play means that I can actually take him, even though it is quite a stretch (he’s a lot wider than my dildo, christ) and his cock is still fucking soaked from me. He finally bottoms out and I can feel his hips pressed against me – and then he starts to pull out. He quickly speeds up, and all I can do is lie there and take it. Normally when he fucks my ass, I ride him and have some control over the intensity, so this is new to me and it feels *incredible.*
I’m clutching at the sheets and moaning into them. He again pulls me up to kiss him while he fucks me – this time by my hair, I wasn’t expecting it – and is still thrusting into me hard while kissing me. My legs start to shake – it all feels too good and standing up is too much for me right now – and I warn him that I can’t support my own weight for very long. He decides that I don’t have to support my weight if I’m just facedown on the bed, and pushes me back down, saying that I just need to lie there and be a hole for him to fuck. I have zero problems with that. He continues to go hard and fast (at this point I’m getting impressed by the energy he has, even after a work day), grabbing and slapping my ass and pulling my hair while I stay there, still grabbing the sheets and moaning. He starts saying my name and his thrusts get a little more irregular until he finally cums in my ass and slowly pulls out. I reach over and slide the plug back in (don’t want to drip on the carpet), but I’ve been fucked so hard that my little plug doesn’t really stay in and drops on to the carpet when I stand up. Oh well, I put my thong back on and slowly work on being able to stand and walk again (I’m still all wobbly). We kiss and head into the kitchen to make dinner.
Source: reddit.com/r/gonewildstories/comments/5pq8ut/i_tm_surprised_my_fiance_m