I travel a lot for work. I’ll be gone for a month or more at a time, several times a year. I am in a big city now, and with work back at HQ and being out of town, my girlfriend said she wanted a guy who would be around for her. I couldn’t blame her for that. I’ve lost other women because of that too. I am bi, turned bi due to being so damn horny on the road at time. I usually find a woman but it is my first week here and I needed some relief. I have fucked homeless women before, paying them, feeding them, even having a couple come into my temporary apartment sometimes. I didn’t want to call an escort, and didn’t want to go to some gay club or something. It’s usually easier to find a guy to fuck than a woman but I wanted pussy. I wanted tits, a womans body to fuck. I looked around for a homeless target or two and they were all men. Finally on the third night I saw what looked like a younger girl in the shadows in an alleyway. I passed the two old, bearded men and went to her. She looked kinda tall for a girl, probably 15 or 16 I guessed, dark blonde hair to her shoulders. She was wearing a hoodie, and torn jeans. I went to talk to her. To my surprise it was a young guy. I excused myself saying I thought he was a girl and started to leave. “Why? What were you coming to say to me if I was a girl?” he said in a pretty light voice. “Well, I thought maybe a girl might want some hot food, maybe some money and stuff” I told him. “in return for what?” he said right back. “Well, to keep me company for a bit”.
“I can do that” he said. I told him I didn’t think he knew what I meant. His response was that he’d had to suck off guys before. It was usually older homeless or drunk men who made him do it. “Well, I may want more than just to get sucked” I told him and he said he’d be willing, adding. “There are no women around this area”. I asked where we could go and he had a place half a block away we could not be seen. I told him I’d buy him some hot food, and pay him with a $20bill. He got up. Walking with him I noticed a distinctly feminine figure. He was thin, only about 5ft. 6in tall and had a great looking ass. On the way I figured to myself that fucking his ass would be really nice actually. At the abandoned house, he went to the garage. There were some old blankets around and he immediately turned and dropped to his knees. I fished out my cock and he was on it. “How many cocks have you sucked on?” I asked him. “Four, this is fifth” he mumbled. It felt good, I was going to get some relief. “OK get up, and turn around” I told him as I pulled him up and turned him around with his butt to my exposed cock. I didn’t have to undo his pants and belt, I just pulled his jeans now exposing his super cute, very very tight, beautiful ass. I brought out a tube of petroleum jelly and creased up his ass and my cock. I had him lean on the wall with his hands, and bent him over. Pushing up to his tight and tiny little sphincter I pushed in about a inch past the head of my cock.
He bolted upright, my cock popping out of it’s new home. “Oh damn that hurts, I can’t do it” he said grabbing his ass with his hand. “Oh damn that hurt it really hurt” he kept saying over and over. I pulled up against his butt with my cock, holding him firmly and pressed my cock up against his ass crack. “No no, please don’t do it, here you can keep your money, I can’t do it, it hurts too much” he was saying. I was at the point of no return. I pushed him standing up against the dirty garage wall, and shoved my cock up his tight little ass. I was all the way in him, he started begging at me to take it out, to give it time, to do anything but fuck him. “You’re getting fucked kid, right up that hot little asshole”. I continued fucking and fucking, but only for about 5 or 6 minutes, then I shot up his ass. To his now crying and moaning, still talking about how much it hurt, begging me to take it out, I was sated. I let it go soft till it popped out on it’s own.
“Here’s an extra $10 for you, pick up your $20 your threw down, you deserve it all. Hey, look, I’m sorry it hurt so bad that i had to do it that way to you, you know, to MAKE you do it” I was trying to apologize for raping him but he just looked at the $30 in his hand. “If you want to go to the diner I’ll buy you some food” I told him. “OK” he said and pulled up his pants and went out the door. I walked with him to the diner took him in and sat at a booth and let him eat whatever he wanted. I even let him take a burger and drink out with him after. “I still hurt a lot. I’m really sore back there” he said continuing “I think I have to go to the toilet, I think it’s coming out back there”. “What’s coming out?” “You know, you’re stuff, you shot off in me, all of it I think it’s leaking out” he explained. “You mean my cum, the cum I put in you when I fucked you?” I asked. “yeah, when you forced me to let you fuck me” he added. He went to the toilet, and came back and finished eating. “Did you get it out of you?” I asked him. “I don’t think all, a lot came out though, a real lot and it’s in my underwear too. “That happens to girls when they get fucked, a mans cum leaks out of their pussies” I told him. “I’m not a girl, I don’t have a pussy, you forced your cock into my butt” he said. I answered “To me your a girl, now, and I fucked your pussy. Look I’m here for a couple of months I’d like it if you’d come with me and be my girlfriend while I’m here”. “I’m not a girl” he again stated. “You are to me, I mean I fucked you and came inside you, I’d like you to be my girlfriend. Can you do that for a couple of months? Be my girlfriend?” He pondered for a while. “Will it be in your place or outside like tonight?” “Inside, my place”.
So the one stipulation was that I admit what I did to you was not what he wanted. I raped him, even though he agreed to do it before, then couldn’t I raped him anyway. So now he wears makeup, dresses, high heels, panties, stockings, a little training bra. He is my girlfriend for a couple of months. I’ve dumped a lot of sperm in his little mouth and his tiny little boipussy.
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