tagFetishBack-alley Sissy Boy

Back-alley Sissy Boy


I saw you while I was walking through the grocery store. You were bent over, picking up something off the bottom shelf. At first, I thought you were a girl, because of your nicely shaped ass and the fact that your low rider jeans were riding down, exposing a lacy white thong.

I was so turned on, my cock started to get rigid right away. If I had been wearing jeans, I probably could have hid it, but as I was coming home from work, I was in a suit and tie, and the thin fabric of my suit pants did little to reveal my hard dick.

I walked up to you, expecting to hit on a hot chick. "Hey baby," I said. I was shocked when you stood up and turned around, revealing a skinny boy.

My shock passed quickly as I checked you out. Light hair, sparkling eyes and a shy smile on a feminine face. A rail thin body and flat stomach, just like I like all my conquests to be, be they male or female. You might not have been a young, female slut, but you were just the kind of young slut I was looking for.

I still wanted you, but decided that you would have to earn it.

"Whoa," I said. "I wasn't expecting a dude. When I saw that ass barely covered by those girly jeans and that slutty thong, I figured I would be getting a chick that was good to go, not some boy in whores clothes."

You looked down at the ground, flushing red with embarrassment. You playing shy just turned me on more.

"Is that what you are, some little faggot in girls clothes? Do you like dressing up like a girl?" I asked.

You didn't say anything, just nodded your head.

"Oh yeah," I said, moving in closer to you. "You know what else girls like?" I asked, thrusting my hips forward enough that my hard-on would have been impossible for you to miss, even though you were still staring at the floor.

"I don't know," you whispered.

I leaned in close and whispered in your ear. "I bet you do know. I bet you want to reach out and touch it. Go ahead, reach out and touch it like the little slut that you are."

You reached out your right hand and started to rub my hard-on through my pants. I shivered with excitement, my boxer shorts already starting to get wet and sticky with pre-cum.

I pulled away a little, but not so far that you couldn't still keep rubbing my stiff cock. You ran your fingers along the entire shaft, measuring out the 7 inches of thick meat. You still hadn't looked up, but I could tell you were liking it.

"God, you are a slut," I said, "rubbing some stranger's dick in a grocery store where anyone could see. It feels good, but I can't have some sissy-whore making me cream my pants in public. I don't want any of the hot girls I am trying to pick up who shop here think I am some kind of fag. Do you live close to here?"

"No, I'm about 20 minutes away by bus," you said.

"Fuck, that sucks. I live near here, but I can't take you back to my place. I have some friends over, and while I bet you'd like to have cocks coming at you from all angles, I don't want to share that hot ass with anyone else tonight."

I could see confusion in your eyes. I think you couldn't decide which had sounded better, a group gang-bang with me and my friends, or some one-on-one attention from me. Either way, it didn't matter because you didn't have a choice. You would only be getting my dick this evening.

"Okay, here's what we'll do. I know a quiet little corner in the back alley behind the store. We'll go there and I will let you suck me off. Follow me," I said. You obediently put down your shopping basket and followed me out of the store without a word.

We went through a dark pathway and came to a back alley that was used for deliveries. Most of the stores that backed on to the alley were closed, and the grocery store wasn't taking deliveries this late at night. It was perfect for me to fuck your face without anyone seeing.

We found a corner that was out of the way, but still had some light and I commanded you to get down on your knees. You started to lower yourself, and then I reached out, grabbing you by the chin and pulling you back up to your feet.

"Actually, take off those jeans. I want to see that beautiful ass in that slutty thong while you are servicing me."

You undid your jeans and slid them off, draping them over a nearby garbage can. I kept my hand on your chin, holding you in place for a moment as I checked you out.

"Pretty, girly face. Tight little t-shirt showing off your flat stomach and thin body. Nice skinny and hairless legs. Very good. You almost look like a chick. The more you look like a chick, the less gay it is," I said, adding, "for me, that is. For you, it's still very gay."

I looked you up and down one last time, this time my gaze stopped on your white thong. There, sticking out hard and small, was your cock. I reached out and grabbed your cock and balls with my hand and gave them a squeeze.

"Would you look at that," I cried. "You are rock solid, though it isn't much of a package to look at. But your thin, short girly-dick is rock hard. God, you are loving this, aren't you. I bet you can't wait to get down on your knees in this dirty alley and start to suck on my big cock, can you?"

"There is nothing I want more," you said. With those words, I let you go for it. You quickly fell to your knees and undid my fly. You reached into my boxer shorts and grabbed my cock and quickly put it in your mouth. I had never seen anyone so hungry for a big dick. It was such a turn on, I nearly gizzed myself right then. I was glad I didn't, though, because once my cock was in your mouth it felt so good.

You started by taking just the tip of my dick in your mouth, and swirling your tongue around the head, licking up all the juicy pre-cum that the thoughts of your ass in that white thong had caused. Then you slowly moved your mouth further down the shaft, eventually getting all of my 7 inches into your wet and warm mouth. It was surprisingly good, I tossed my head back and moaned with pleasure.

I didn't keep my head back for long, though, because I wanted to watch that ass as your sissy-boy face sucked me off. "Stick out your ass so I can get a good look at it," I commanded. Wordlessly you stuck it out to give me a nice view of it. As you gave me a very sexy blow job, you moved your ass slowly up and down, driving me wild with passion. Watching that beautifully, girly ass in those slutty white thongs, I was torn what to do. Fucking your pussy-mouth was feeling so good, it was warm and wet and soft, but watching that ass made me wonder if your little fuck-hole wouldn't feel any better.

After a couple minutes I had decided, I needed to fuck that ass.

"Jesus, whore, I can't take watching that ass anymore. Get your face off my cock and pull off those panties so I can fuck your pussy," I screamed.

You got up off your knees, and leaning up against the wall of the alley, pulled down your thong to reveal the most glorious ass I might have ever had the pleasure to fuck. I wasted no time in positioning myself behind you, and got my cock pressed up against your tight little hole. I started to press in. At first, your sphincter gave resistance, but then your expert and well-used butt opened up like a flower blooming, and I was able to slide all the way in without any trouble.

Lucky for me, I had made the right choice. Your ass was better than your already incredible mouth. It was tight enough to give me a really nice ride, without giving too much resistance. It was warm and deep, and it made you moan with pleasure when I shoved myself all the way into you.

"Oh, you little slut whore, you have such an incredible ass. It's too bad that this ass is on such a sissy boy, otherwise I would make you my girlfriend right now. You would like that, wouldn't you, being my girlfriend?" I asked.

"Oooooh, yes. I want to be your girlfriend," you cried as I pounded into you.

"Fuck, this beautiful ass, I wish I could. But you're just a sissy boy, so all you can ever be to me is a fuck thing. I'll call you up, come over and fuck this beautiful ass, and then leave you to go and date my beautiful women. You'll wish you could be more to me, but all you'll be is my fuck-toy. Do you want to be my fuck-toy?" I growled in your ear.

"Yes, I want to be your fuck-toy!" you cried.

"Do you want to be more than my fuck-toy?" I asked.

"Yes, if you'll have me as more, I'll be more. I'll do anything," you groaned, your face was pressed up against the brick wall as I pressed myself deeper and deeper into you.

"Well, you'll have to try really hard if you want to be my girlfriend. You'll have to dress up pretty for me and be my little slut whenever I want. Then, maybe if you can look like a pretty little girl and be the kind of whore I want you to be, in the future, I'll think about making you more than just a cum-bucket," I said. "But for now, and I do mean right now, you are just a cum-bucket to me."

My pace quickened and I came in your ass, thrusting stream after stream of white goo deep inside you. I pulled myself out of you, and like a good little slut, you cleaned up my cock with your mouth before I slid my cock back into my pants and zipped myself up.

"Now, give me your mobile number, boy. That way, I can call you whenever I want to arrange a fuck-meet. You aren't going to get my number, not yet," I said. I took your number and programmed it in my phone, making sure to put the code in to block the incoming number if I called you. Like I had said, for now I would be the only one who could initiate a session.

You stood there, naked from the waist down in that filthy alley, and looked at me. I might have treated you like a whore this night, but looking at your pretty, feminine face, I could see you had potential. I grabbed you by the hair on the back of your head and pulled you to me, kissing you hard on the lips for 10 seconds, letting your tongue explore my mouth.

"Mmmm," I said, "that could be a taste of things to come. If you can make yourself a pretty little girl for me, then you'll get more kisses in the future."

With that, I left you in that alley, naked from the waist with my cum dripping out of your ass. I didn't look back, but I knew you were watching me. And I think that you knew that it wouldn't be long until your phone would be ringing, and I would be seeing you again.

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