Hitchhiking After Dressing Up as Girl for Halloween Party

Here is something I will share, that actually happened to me a few years back. It seems like yesterday, but I was much younger, so I guess it was longer. The year was 1986, the year of the expo, and I was a foolish young man. I wanted to go to a party in the fall, a Halloween party, but with no costume, I had to think quick, the old stand by was to dress like a woman again, I had done this before and really wanted something new, but on short notice, I did what I had to do.

I decided to ask my sister for help as I had done before, and she was willing to help. We care about the same size, being I am a small frame. I am smooth, almost hairless can't help that, but it is what it is. After trying many things the one we found that was the best and well maybe most provocative was a short blue leather skirt, it fits around the waist the best and is comfortable, followed by a blouse tied in a knot in front and a pair of flat girl shoes, all her panties are too tiny they squeeze my parts, so I ended up with a g string.

So not we know what fits, so let's do some prep, and while wearing the g-string, my crotch hair is showing what hair I do have, lol. Still, I shave smooth, then my sister does makeup, and I have short hair, so easy to try a wig from mom's closet, and after a couple of hours, I am transformed, unbelievable I can't really recognize myself even my sister is in awe.

All ready to go, I get a ride from her to the party. We part ways. When I entered the party, the looks I got were wild. I just walked around looking for a couple of friends there and soon found them. They could not believe the transformation we all laughed, there were 100 people or more it was huge and lots of fun and as the night went, my friends left. I stay, thinking I will get a ride with someone else.

Now it's getting late, and I'm drunk, well happy, not pissed, and men are flaunting over me, catcalling me, and you know drunk guy stuff. I take it with a smile, soon it's like 11.30, and I kind of had enough most couples have left, and it's mostly guys who drank too much, and the catcalls are getting rude, so I decide maybe I should just go and hitchhike home, it's about 10 miles.

Get out and walk to the highway service road and stick my thumb out and nothing. It's like a little after 12 now. I keep thumbing, and this white van drives by with two men. They slow as they drive by but don't stop. 10 minutes later, I recognize the lights. It's the van again and the slow-down look, but drive on by. Well, it's getting late, I feel, and hoping for a ride. Still, no luck, and another 10 minutes and the van reappears. This time it stops. As I get to the truck and try and use the side door, the passenger tells me it's broken, and I have to use the passenger door. He is a much older man than I am, kind of dirty looking and ruff unshaved, and as I step up, I feel a hand on my ass. He says, there you go, little lady, and I quickly replied I'm a guy.

The van takes off, and I find a place to sit in the back. There is a mattress, and I sit on it at the back, facing the front. I sit with my knees up, the old guy turns to me and looks and says I am a sight for sore eyes, and I laughed telling him where I was, and once most people left, I was getting catcalls, you know drunk guys, and I laugh. He replies I can see why you look fucking amazing, hot as fuck! You're giving me a boner, lol. So I told him my sister helped I even had to shave to hide my pubes. He's like, oh ya let's see, the driver is just driving he is younger and pretty stocky, so I said now you know I'm a guy right, and he said guys can suck cock too, bet you are one of those, wow where did that come from I reply, just saying he replied.

We are on the service road going slow. Just like that, the driver says he has to piss and turns off in the industrial park, drives till he sees suitable parking, and move around the back of the building and stops. He gets out, does his thing, and the old guys come to the back and kneel in front of me, saying, I am so fucking hot, show me your shaved cock, I want to see it. I tell him noo, really, he says, show me. He spreads my knees, exposing my g-string, just like that he says we're going to fuck you, you dress like that and hitchhike well you are getting some, now I'm worried as he makes a move on me, we wrestle a bit, but he is way stronger than me and I tell him I don't want to fight I just want to go home.


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Just then, the driver reappears and sits in the driver's seat, looking up in the back when the old guy says. I said I would suck him off for the ride, and the driver went, mmmm, come on, boy, let's see, and he started to wrestle me again, so I said, ok, ok, just don't hurt me, and it started. I watch him take off his jogging pants and out flop a limp dick. He grabs the back of my head and brings my mouth to his dick, and says, go ahead, I'm waiting. So just like that, I open my mouth to take him, I can feel him growing in my mouth, and he is kind of ruff sticking it deep down my throat, he starts peeling off my little over the shoulder coat and banging my mouth as his friend is taking his pants off, soon both of them in the back. I am being stripped of clothing, I didn't have much on, and now I am naked, shaved smooth like a little boy, and it gets then going, they want to 69 me, and I have to oblige as I get on top of the driver he starts to suck my cock and I take him, it felt pretty good for sure but strange too.

I feel the old man caressing my ass and spreading my cheeks while in a 69 position, and I feel him kneeling behind me and rubbing the tip of his hard cock by now up and down my ass crack while I am being sucked on. I can't help it. My cock is hard, and rubbing my hole with his cock is not helping. I am horny now. I feel some gell pushed in my hole from a tube and a finger to push it in more. Soon I feel him pushing his cock in me slowly while I'm being sucked, the feeling is intense, and I am helpless to those two, then he starts to fuck me slowly at first and the picks up the tempo, omg this is really happening he is fucking me as he said, he would.

I am ready to cum and can't help it when I let go. The driver doesn't stop sucking me, and I am squealing. The orgasm is so powerful, and I want it to stop, but he keeps sucking, my knees get weak. I just lay on his face while his friend is plowing me. Then he tells his friend to let me up, so we stop and reposition, now I am on all four, and he shoved his dick back in me. I have to start sucking the driver. I am being spit roast and can't stop it. It's happening; I am being manhandled as I feel the guy fucking start ramming me hard all the way, and I hear a big grunt. Finally, he is done, I think, and we stop for 2 few minutes as he tells me I have a great ass, the best he's had in a while. His buddy told me to lay on my back. I do it but really taught we were done. Still, not so. The younger driver is average in length but really wide. I had to open my mouth big to take him. The old guy kneels with my head between his knees. As the driver lifts my legs over backward, the old guy holds them like that. I am so venerable at this point. My lubed open hole is in the air for his, and I see him get in position.

Just like that he had no problem going in, but it hurts in that position and he goes deep and I scream, stop ouch stop, he didn't instead he just kept going in and out deeper each time and he was all in in a couple of strokes, my lord did he ever hurt, he lays on top of me and starts to fuck the life out of me, he's worst then the old guy he's banging me hard and it does hurt but he doesn't care and soon the pain starts to get less and I just let it happen, im not sure what time it is but it's late and I can't stop this, we change positions again as I sit on the younger guy and get a mouth full of old cock that's been up my ass in my mouth, and here we go again getting royally fucked, they both fucked me several times over the next few hours, they had a good old time and finally I think their done and I get dressed, but now they want to drop me off at my door, and I don't want them to know where I live, but he had my id and drops me off right in front of my place, before letting me out he told me if I wanted this to stay secret he want to do this again, or he will put it in the news papers personal adds and expose me, I said ok ok no need to do that what did you have in mind, he said friday you meet us at the back of the shopping mall parking, you dress normal or not I like both, but you meets us there and were going to fuck you again.

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written by bottomjo

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