I was talking to this ladyboy (yes, I knew from the beginning) for a while online, met him on okcupid. I never did anything with a guy, but I figure if he looks and sounds enough like a girl then fuck it, what's the diff? He was really nerdy and shut-in so I didn't figure he was the type to be hanging out in rest stop bathrooms. Turns out he lives pretty close and we started snapchatting. He looks short and skinny like a bit more chinful Alexa Chung in pics. So I ask him if he wants to hang out and he comes over a few days later.
He calls me to say he's here and the first time I answer I'm like terrified he's gonna sound like a dude, and I dunno if I can take that. He puts on some approximation of a girl which was comforting, I guess. I have to go out in the parking lot to find him and when I finally see him and I see his face and it's essentially a dude with a girls haircut; great big nose and chin; I'm like "yo!" and I am kind of struggling to not look at him again. I keep saying like "you want to drink? We need to go get some juice or something to mix". So we go to the store and every time he would get in front of me I would look at his ass in these girls jeans and it's so little and puny like the pockets are touching together.
So we go back to my place and we hang out and he beats me bad at Mortal Kombat. He's super easy to talk to though, so that wasn't a hurdle at all. Was like talking to any other guy or girl. I turn out the lights to watch some anime movie and look over and realize he looks way better in the soft light. Like could totally be a night model, and start drinking... and after about 3 drinks I start to kind of rub his elbow, and he's not shying away or anything.
Let me take a moment to address the way this dude smells. I don't know if its the shots of estrogen or some weird perfume, but this dude smelled so fucking weird. Like a nursing home, I think. Not rotten, almost like mildew. And it is so strong.
Now I start pushing up on him and I got my hand up his shirt rubbing his stomach and stuff, and I start inching a pinky down the top of his pants and this is the first realization that what I'm doing is pretty gay. Because my finger brushes up against the tip of his dong. I start thinking like "what the fuuuuck am I doing?? Why am I doing this?" But I'm drunk and the train is already building up momentum. With any girl, I'm just like "target acquired", and it's just go time. So I kiss his cheek and I start rubbing his butt and he's kissing me back and I touch his dick and it's so weird and little, like he's wearing low rise girls pants and the thing is hard, but it's still not making it out of the top of his pants.
He kind of rolls over and sits on me and is like "what time is it?" and I hop up and grab my phone and am like "midnight", so he's been there about 6 hours. He goes and I walk him back to the car. People see us and I immediately begin to appreciate how a lot gay people must feel all day every day, like "I hope they don't just decide to jump us for walking past them." Anyway, we say goodbye and he goes.
I immediately block his number and snapchat and all that, but after a few hours I think "Dude's fun to hang out with. We like the same stuff and he's pretty funny and all that." So I unblock him from everything and he doesn't seem to notice. And we talk some more and I'm like "want to hang out Monday?" and he's like "sure." He sends me some snapchats of him in some lingerie and he looks like a skinny hot girl! Face and all, looks good! And I'm so fucking confused! So I'm like "gonna wear that skirt Monday?" and he's all "if that's what you want."
So he shows up in this skirt and some weird white leather cowboy boot things and I'm just so bummed because, once again, it's a dude in a skirt and some fruity boots. This time I just immediately start knocking back the vodka. We're watching a movie. We drink all the vodka, and I just starting drinking Jager from the bottle. Which isn't abnormal, I like the taste of it, but I'm really trying to get drunk for this. I start touching his legs, and they're like girls legs. I start rubbing his butt and it's like a girls butt. He's wearing a thong which makes me laugh now when I think about it.
I start rubbing his gooch because I don't know what the fuck I'm doing. I know what girls like, but what the shit do I do with this stuff? So I start rubbing on his asshole... start pushing some digits in. Rubbing his dong and stuff and I'm so bummed. I so badly want it to be girl parts and I'm treating his dong like a big clit refusing to stroke just rubbing it with the middle and ring fingers. I start using more and more fingers and I stop for a second and think of Band's sig of that dude greasing his hand up. I grab a bottle of lube from the other room... I come back and start doing three digits. Then four. I'm literally doing my best to fist this DUDE'S. ASS. And it starts smelling so bad like a fucking broken sewer pipe. I just start thinking "How the fuck does GAY do this? It's so horrible." And I can't quite get past the knuckles and he's into it, I guess? I can feel little bits of shit going up in my nails and getting all over his ass. Eventually he says it hurts, so I stop, and go wash my hand for five minutes. He wants to go lay down, so we go lay on the bed. He starts bending over and pushing his ass at me and saying "You have a condom, right?" and I am so fucking limp like a fucking shoe string no way no how that is going to happen. So I just flip him over and I'm kissing his stomach and hips and I can feel his ball hairs brushing across my mouth and I'm biting his thighs and tugging on his ridiculously hard crooked little dong and stuff but I just CANNOT BLOW HIM, no, no-no. So I just kind of roll off and am like "my arm's tired." And I go back to the other room and start the movie up again (we were watching Arachnophobia). He goes into the bathroom and I can hear him farting like a fucking whoopee cushion. He comes out and sits down and after a few minutes he says he needs to go.
So he takes off. I washed my hand for, at least, another 20 minutes with vinegar, bleach, peroxide, rubbing sliced lemons and limes all over it, I boiled my ring for like 45 minutes. It took 2 days for it to go away, or at least for me to be able to notice it anymore. Haven't talked to him since, blocked him on everything. Anyway, if you ever see a tranny and think "what's the diff?", that's the diff.
Topic: Awkward Sexual Experiences (Read 464563 times)