u/JustaXXXalt

I was hanging out with my housemate, we've been friends for years, ended up living together in his house. Very bro environment. Nobody knows that I'm a sissy, but I've been bisexual since I was super young, so I'm the gay guy of the house and the extended friend group we have.

Tonight, we're hanging out, chilling, smoking weed, and we are talking about life, and we are talking about what is going on with an ex-friend of ours who is now trans. He joked that we should call them up, apologize for some of our past behavior, and then say we are transitioning. Bearing in mind that we are both large men, it's a funny idea. And I'm immediately turned on, because I like this stuff, I like dressing up, I serve guys online sometimes, I use a vibrator, and sometimes I'm in chastity. I stay smooth shaven too. I'm an undercover sissy, as it were. And so I laugh along with the dumb joke, and I'm just thinking about him with big boobs, and his cock all tucked away or in chastity and wearing panties immediately.

I don't know why, but I said, "Yeah, and I already have the clothes for it."

And he raised an eyebrow, and I'm like, "Yeah, I got stuff."

Now we're in my room, and I'm showing him all my lingerie, bras, panties, the whole thing. He's straight; he's never shown any interest in me sexually. Shortly after I moved in, I told him I would blow him if he just needed some help draining himself; he thanked me but declined. So I'm surprised we're having this conversation, and I got even more surprised when he wanted to try some stuff on. And a few moments later, my straight alpha roommate is wearing a peach thong and a cute bra. My clitty is hard at this point. And he invites me to dress up. I'm not naked; my clitty is hard, and he can see it. I don't say anything and put on a bra and panties. We are both chubby, so the bras have something to hold. We're walking around, looking in the bathroom mirror. And he's like, "I get it, I feel kinda pretty." And I'm like, "Yeah, that's why I like it; it was the best thing I got into, even though it can feel weird."

We start smoking, and now we're hanging out in lingerie. I admit that I pretty much either don't wear underwear or wear panties. I actually just ordered a bunch more because I'm basically getting into this full time. I threw out almost all of my guy underwear. And so we're hanging out still; we're still both ass naked except for thong panties and bras. And I just kinda start laughing. I admit that I never thought this would ever happen. He let me tuck his balls behind him for a nice smooth look.

Then he stands up.

"I think I need to shave."

Now we're naked, in the shower, I'm shaving him down, he's already pretty smooth, but I'm shaving everywhere. We both shave our faces so our faces are smooth. We dry off, and I pull out my other makeup bag, and pretty soon we're painting our faces and giggling along. Again, never thought this would ever happen. I'm standing in the bathroom, smooth, wearing lingerie with my buddy and helping him with eyeliner. We're now basically in full girlie sleepover mode. It's kinda hilarious.

After we finish with our faces, we just spend a bunch of time looking at our handiwork. I noticed that his dick is hard.

"Your clitty is getting hard."

"Oh yeah, I guess that would be the right term."

"Yeah, do you...want to rub together?"

We're on the couch now, we're openly jerking, we've talked about doing this, but we've never followed through. I get some porn going mostly for atmosphere. We're mostly looking at each other. And I cant deny, its sexy. We do this, for awhile, I'm using a vibrator, like a good sissy and I like try it out too. I offer my ass to him but he waves it off, he keeps jerking. I keep rubbing with te vibrator.

I watched him tense up a few times, he's rubbing his whole body, he's loving the smooth feeling. He has some pretty puffy nipples and they are very hard right now. This is like a crazy dream come true for me. I don't want it to end. But I watch blow absolute ropes all over himself. I mean, its a real gusher. I get my sissygasm not long after, and we're just hanging out with our own cum, still dressed, still sissified.

It's been a couple hours; he gave me back the clothes and rinsed himself off. I asked if he wanted to take the make up off, and he said he did so I helped him with that. I jump in and rinse off and take my make up off. And he's like "Yeah, that was hot, I'm tired." And he just went up naked to go pass out.

I'm in one of my robes and I'm hanging out in my room typing this out as I'm trying to process what just happened.

Like I said, our night got very interesting.

Edit: I forgot a fun moment when I told him he had to sit to pee, he made the dumbest, cutest face as he dutifully pulled down his panties and sat to pee. I got a text from him a few minutes ago asking about "butt stuff" and if that was possible. I may have created a monster.