Gay stories 

Sexy Surprise

August 26, 2013 / by gaystory

First I would like to thanks Chibiminty for the editing.


What day is it…?

Oh, yeah. It’s Sunday. I always have issues on Sundays, but this time I feel like I got hit by a freight train, and waking is like coming out of a coma. With great effort, I crack open one eye. The familiar sight of my ceiling greets me. At least, I think it’s mine. I shift a little and see my bureau along the wall. Okay, definitely my place.

The sheets rustle, even though I’m still. Someone’s with me; guess I got lucky last night, but I can’t remember a thing. I need to focus and see what I do remember, so I close my eyes. Like a rusty projector rattling to life, the events of last night start playing fuzzily.

It was a usual Saturday night for me. Having moved to Miami just recently, I don’t have a lot of friends, so I go out alone on Saturday to try to catch some girls and score. I have to tell you that Miami is the perfect city for that if you have a good body and a good credit card, both of which I possess.

I was still discovering the nightlife of Miami and this week I tried a new place. Before leaving I had a couple drinks at home, and I arrived in an extra good mood at the club. After some mingling, I began talking to this young girl that was here on holiday with some friends. I started the usual BS; we danced, had a few drinks, and soon we were feeling a connection. We started kissing on the dance floor, and the ambiance jumped up about 10 degrees. I was totally turned on, and she knew it. Soon it was like, 3 or 4 in the morning, and we were pretty hammered by all the cocktails and shots. I remember we were talking about going back to my place when her friend– you know, the not-so-cute girl who doesn’t want to drink and doesn’t want to go back to the hotel alone– showed up. And of course this bitch convinced my girl to go back with her to the hotel.

I cannot tell you how frustrated I was. I was really having a good time with this girl. I remember that I even asked her to bring her friend to my place for a threesome. I think that’s when her friend left. By then I must have been really drunk, because the movie in my head turns into confused snapshots. I remember walking back to my condo; I think maybe I got a bite to eat at some café; now I also remember the girl with me, a Latina in a blue dress. She talked to me, but I don’t remember what she said, just the feeling of her whispering sensually in my ears. We were in the street the as the sun began to rise, walking to my apartment. We made out like crazy in the elevator, and by the time we entered my apartment she was already topless. She had the nicest fake boobs I’d ever seen.

She pushed me onto the bed and immediately got my cock out of my pants. As soon as she started working on my cock I was in another world, paralyzed. I’d never had a blow-job this good before. She blew me like a queen and I think I fell asleep as soon as I came.

I just can’t remember her name…

I open my eyes again and look over at her. She has her back turned toward me; I can see she’s just wearing a white tanga that goes well with her caramel skin. She has a beautiful round ass. I decide I have 2 choices. One: showering and then preparing breakfast. Or two: try to continue what we started a few hours before. My cock was hard again, just from remembering the amazing blow-job she gave me when we get here.

Naturally, I choose the second option. I move over and press myself against her back, kissing her neck, rubbing my cock against her ass. I reach across her to play with her boobs. She stirs, moaning softly, and turns toward me to kiss me. Soon she start moaning and turn a little bit her head to start kissing me, Taking that at a go to explore more of her body, my hand slowly moves from her boobs to her tummy, then to her side and finally down toward her pussy when I encounter a big surprise. Never in my life have I gotten out of bed this fast.

She’s a he, heshe, tranny, wha? My brain is going a mile a minute, thinking not very nice things. The girl has a dick. Whoa. Just so you know, I have never, even in passing, been interested in having a same-sex encounter, let alone… whatever this was. I don’t have a problem with it, anybody can do what they want and all that, but it’s not for me.

So here I am, naked and still hard, trying to understand what’s happening.

“What the fuck are you doing?” she asks. “You just realizing that now?”

“Yes,” I reply. “Sorry…”

Now, most guys would be pretty pissed off in this situation, probably even get violent. Maybe it’s the hangover, or maybe it’s the lovely disappointed face she was giving me, but I really am feeling apologetic for my reaction.

“I am sorry I didn’t know, and I like girls, it’s nothing against you,” I say, going back to sit on the bed.

“But yesterday you were saying so many nice things to me.”

I don’t know what to say. I’d rather have her leaving right now, but she was not moving. What to do? I don’t want any drama… But I wanted her out of the apartment, preferably discreetly.

“Again, I am sorry if I gave you the wrong idea yesterday but I was really drunk. This—you and me—it’s not going to work,” I say, as calmly as possible, trying to keep things under control.

She pouted a little. “Are you sure you don’t want to see what it’s like?” she says, scootching behind my back and draping an arm across my chest, kissing my neck.

I take hold of her arm, trying to displace it. “Stop, please,” I say, a little desperately. “I—I’m really not into that.”

She moves back a little, I’m hoping she got the message and she’s going to go. But I forget she’s a he also and when a man is horny he has the tendency to insist.

“Look, I am going to be really direct here,” she says. “I know we’re probably never going to see each other after today, and I know you want me to leave, but I am horny and I want your dick. You don’t have to touch mine, but I want to feel you in my mouth and in my ass.”

Part of the speech reassures me. First, she is going to be only a memory in the very near future, and second she doesn’t want to take my ass or have me blow her. Maybe it’s the alcohol still in my blood, or the memory of the blow-job she gave me, or the lack of sleep, but it seems like a reasonable offer.

“Ok,” I reply, “but keep your you-know-what inside your tanga.”

I stand up and turn to face the bed. She jumps on my cock, like she’s expecting me to change opinion. My memory is right, she sucks like a queen. I close my eyes and try to imagine it’s somebody else working on my cock. My hard-on had gone down, but it’s right back up now from the treatment she’s giving it. I open my eyes for a moment and look down. From my point of view, it’s like she’s just a woman. There’s no denying I’m turned on.

She guides me down onto the bed on my back and continues working on my dick. Her mouth slips little by little from my dick down to my balls… and then to my ass. Her hands were still keeping my dick busy, but she was licking my asshole. It’s a first for me, and I found I was enjoying it, so I let her continue. I don’t know how many of you have tried this, but it’s a beautiful sensation. My legs spread of their own accord, letting her tongue go deeper into my ass. A few moments later, her mouth returned to my cock, and I had mixed feeling of regret and relief.

The relief, however, doesn’t last for long. Suddenly I feel her finger sliding into my ass, and I realize she’s not done. Her finger goes inside so easily that I’m surprised. I kind of want her to stop but every time she move her finger a certain way she does a move on my cock that makes me moan. I’m being played. She’s controlling me. I’m her toy. And thanks to the fucking alcohol and her knowledge she’s keeping me on the edge.

She has a second finger in now, and she’s still working my cock with her mouth. I feel like I’m about to come, but she takes her fingers out of my ass and removes her mouth from my cock after a moment.

“Got a condom?” she asks me.

Dazed as I am, I barely manage to nod. I open the drawer on the night stand and give her one. I put my head down and close my eyes, waiting. I hear the sound of the packet ripping open, but it’s several seconds and I don’t feel it on me…

Oh. Right. My brain is back in full gear, and I realize why she needs the condom. I open my eyes, see it on her, and before I can protest she takes my legs, places them over her shoulders, and pushes into me.

“Oh,” I gasp, not managing anything else. She’s still rubbing my cock with her hand, and moving inside me, and it feels amazing. I didn’t know a man can feel so much pleasure. I half-expected to feel like her bitch, violated like this, but it’s nothing like that, just 100% pleasure, but I’m not sure it would have worked without her giving me a handjob.

When my orgasm hits me, it’s like an electric shock in my balls. A n amazing quantity of come shoots out in 4 or 5 bursts, onto my chest. She’s out of me now and I think she’s coming too, but I’m too wrapped up in my pleasure to be sure.

We lie next to each other, not touching, trying to get out breath back. I can’t bring myself to move.

“Thanks,” she says finally.

“Thank you,” I answer. “I’ve never felt that before. How did you do it?”

She smirks knowingly. “Honey, I have the same equipment. I know a thing or two about how men work.” My face heats up, knowing she’s teasing me, but she laughs, and so do I.

Afterward, I hop into the shower. She takes one after me. Then we end up having breakfast together and chatting about whatever, totally normal.

Before she left, she gave me her number. “You never know,” she says, with a grin.

When I think on it now, I’m not sure what to think. I’m not about to tell anyone what I’ve done, but I don’t feel any shame. I’m not questioning my sexuality, either. I know I’m straight; I have no desire to kneel in front of a guy and suck him off. And this… this is different, somehow. I really enjoyed it. I’m not sure I want to do it again, but I’m keeping her number, just in case.

Because she’s right. You never know…

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