Worth Every Penny

I had only had a few drinks, and so was thinking and talking pretty clearly, despite me swaying every now and again. The cold air and dark streets made it harder to walk in a straight line, but mostly the alcohol in my system was mostly just making me light-headed. I had been ditched by my friend at the bar, who'd sauntered off with a hot guy from France, but I was in a good mood. I gave an overly-friendly smile to a passing woman, who looked at me suspiciously.

The streets were dark and I was quite a long walk from home, but I wasn't worried. This area of town rarely saw any danger, and besides the booze had made me optimistic. I turned down an alley that connected two quiet roads, taking a route I hadn't taken before.

Sitting on the floor was a man, indiscernible under the shadow of the wall that he leant against with the glare of a streetlight in my eyes. I made the connection that he was a homeless guy, with nowhere to go for the night. Being in my overly friendly frame of mind, I walked over and slumped down next to him. "Howdy."

He looked at me and gave a humoured smile. "Hey there. Been out?" When I nodded, he prodded further. "Had fun?"

"Yeah, it was a laugh. And the booze was cheap." He laughed at that. I gave him a sympathetic smile. "Got no place to go tonight?"

He opened his mouth to reply, but then registered what I had meant and started to laugh. "I'm not homeless, you know. I just had a few too many drinks and sat down. I live up on Newgrate."

I went a deep shade of red, but he seemed to find it funny so I let it drop. "Newgrate? Not in the big houses, with the columns and french windows?"

He chuckled. "I'm afraid so."

"You must be filthy rich then!" He gave a modest smile, but I pushed further. "How much money have you got on you, right now?"

At this he looked around, saw nobody was looking, and brought out his wallet. In it was a thick wad of money, more than I'd ever seen before. The look on my face must have been priceless - he at least had the decency to go red. "Earlier today I was meant to put a deposit on a car but never got round to it. This is one grand, but I don't normally carry this around."

Since I'd started at Uni I had been constantly low on money, always having to borrow from my friends. I could never have asked my parents, who had been in debt since they'd first had me. This was about ten times as much money as I'd ever seen in one go.

I realised I was staring and tried to smooth it out but he was interested in my reaction. "How far would you go for this money?" he asked, seeming genuinely curious.

"I would do a lot of things," I laughed.

"Would you kill someone?" At first I was startled, but seeing the glint in his eye showed me he was joking and I laughed. "Maybe not that far."

"Would you suck a dick?" This time I actually thought about it. It did sound a tempting offer, and it was a lot of money, but my conscience went into overdrive and I came out with, "No."

However, even though it had been for only a second, I had hesitated on this one. He noticed straight away and grinned. "I think you would!"

"That'd be prostitution!" I protested.

"It'd be you having some fun, and getting a whole lot of money at the end of it." His voice was smooth, and he put it like it was a fun game that I could be playing.

I snorted. "Well, it doesn't matter anyway. What do prostitutes get, 100 for the night? If they're lucky. Nobody's gonna pay me one grand to suck their dick."

"I would."

My head snapped round to look at him. The gleam was back in his eye, but it wasn't one of jest this time. This was a genuine proposition. I laughed loudly but nervously. "You'd give me all of that money to suck your dick? I don't think so."

"Why not? It's just a bit of fun. And it's not like I don't have the money to spare." I declined, but again I allowed myself a second's hesitation, so he dove in head first. "You're a college girl, am I right? You need this money, and it's not like the job market's forgiving. So what's the worst that can happen? I'll get pleasure, you'll have fun and get a big wad of money at the end of it, so nobody loses!" I laughed, but it was an uncertain one - why was this so tempting?

I imagined myself doing it. I'd take out his dick, and just suck it, right here in the street. I felt my mouth water slightly but there was no way I could do it. What if someone saw? The rumours would destroy me completely. What if he had an STI? Unlikely, from his background, he could get all the attention he needed, but it was a risk. Anyway, it was degrading to women, and was morally wrong.

And then he did something completely wrong, completely inappropriate, but it silenced every single voice in my head telling me that I shouldn't do it.

With that hand that wasn't holding his bulging wallet, he reached into his bulging trousers and pulled out his dick.

It wasn't that it was an especially nice dick. I mean, a dick is a dick, and admittedly his was slightly thicker than most, but it was average length and there was nothing special about it. But it was one of the single biggest turn-ons of my life. Partially this was due to his attitude, his confidence in just being able to take out his dick and expect me to suck it. Partially it was the fact that a part of me liked that he and his wallet had a dominance over me, a type of control. But mostly it was because it was just suddenly there. I didn't slowly get it out in the bedroom, when it was expected of me. It was in the middle of the street, at the most unexpected of situations, but it was just standing there, hard as a rock, pointing straight up towards the sky. It was completely out of place, completely inappropriate, and it was unbelievably attractive.

I was speechless. I had nothing to say, my mind was numb. My eyes drifted from dick to wallet to dick, but no thought processes were going through my mind.

The man seemed to sense my daze. He reached up a hand and pushed some of my hair behind my ear. His hand stayed on the side of my face, before moving round to the back of my head. He didn't push my head downwards - I'm not sure he even applied any pressure - but somehow his hand seemed to guide my head downwards towards his dick.

Had I been at another angle, had I had to shift my position in order to suck him, the spell might have been broken. But somehow I was sitting in the perfect position to just dip my head down. I bent over, and my mouth went over his dick. My lips softly traced his hard shaft, travelling further down his dick. Then I squeezed, and pulled my lips back up to his head.

There was a dick in my mouth. A rock hard, thick cock just sitting in my mouth, ham mocked by my lips and tongue. My heart beat was racing and my mind was whirring with a mixture of emotions. I felt confused, I felt a little bit scared, but mostly I felt excited. This was unbelievable, this must be a slutty dream - and yet as I pushed my head downwards it was a solid, real dick that twitched in my mouth.

His hand stayed on the back of my head, gently pushing every time I went down. I sucked up and down, caressing his shaft with my moist lips. My tongue traced his bulging veins and stroked the underside of his head.

He tilted his head back with pleasure and moaned, but then seemed to decide that his need to watch me was greater than anything else. He stared intently at my brunette head smoothly sinking down on his dick before pulling upwards with a suck of my mouth, breathing heavily. My nipples had hardened through my shirt and I longed to play with them, but all my focus was on his dick. I flicked the slit at the end with my tongue and his whole body quivered with pleasure.

I went down again but this time his hand pushed more firmly, not letting me come up. Realising straight away what he wanted me to do, I gripped my thumb and slowly pressed forwards. Fighting the gagging sensation, I felt the round head of his dick pushing past my uvula and into my throat. His dick twitched with the intensity and my throat automatically clenched on his dick. He gave a loud gasping moan at that, and I felt the head of his cock bulge.

I pulled out, tracing pleasure lines on his dick with my wet tongue, but when I pushed forwards I once again opened my throat to him. My mouth was deep, so when he was in my throat I was able to lick the very base of his dick with a stretched-out tongue. I pulled away slowly, allowing me to lick all the way from base to tip while sucking sensually on his shaft.

He was loud and the alley wasn't particularly secluded, so at some point at least one person must have seen us, but the alcohol working with the huge amounts of adrenaline made me blind to all else but his and my pleasure. I had forgotten about the money, it had left my mind - I was focussing purely on giving him as much and as many different types of pleasure as I could.

After a few more minutes of intense sucking, his dick began to twitch more violently and I knew he was going to cum. The head of his dick swelled up and, knowing it would be sensitive, I drew out and sucked only on that. His load was building up and building up but my sucking was teasingly minimal, only allowing him to get close. I carried out my fun as long as I could but, sensing that he couldn't last much longer, I plunged my mouth down on his dick. His thick cock exploded with cum, filling up my mouth almost instantly and swilling down my throat. I held back a gag until the urge to had gone away, at which point I sat up and swallowed my mouthful. We both sat there, panting.

He pulled out 900 from his wallet and stuffed it in my hand. "The last hundred is for when you clean my dick," he panted.

I bent back down without a word and put his now-limp dick in my mouth. It hardened slightly at the sensation but it was extremely sensitive, and he gasped loudly with every lick. I licked all the cum of his cock, gave one final suck and sat up.

He breathed deeply, his chest heaving up and down. As if in a trance, he slowly pulled up his trousers and did up the zipper. He leant back, and chuckled breathlessly.

"Worth every penny."