The Decision

I'm taking quite a risk in putting this on paper. If it ever sees the light of day, I'll be in deep shit in at least one of my lives. But I'm faced with a life-changing decision, and I need to set down the facts so I can sort them all out in my mind. How did I come to this point? Will I make the right decision? Am I being stupid? I have a hell of a choice to make, unless I find that I've already made it. So, fingers crossed, here goes.

I'm not much for memoirs, but I can write; I was an English major, after all, and make my living in large part by writing, in the daytime, anyway. Just to be on the safe side, however, I think I'll withhold any real names here, though realistically I suppose a good detective could figure it out.

Where to start? I suppose the fork in the road came several months ago, not long before college graduation. Perhaps if I had come from an ordinary family, a good, simple family with fewer trappings of wealth and more plain common sense, what happened then never would have happened, and I wouldn't be writing this now. Should I regret that? I'm really not sure. Anyway, at the time I was just beginning to transition into what I expected would be the rest of my life. It was the life I had been brought up to expect, the one my parents and friends expected as well. Through family connections I had already secured a job as an intern at a good law firm in Manhattan editing legal briefs, primarily to fill in the space between graduation and my expected marriage. My fiancé and I had begun to discuss our plans for the future. It all looked so bright, so predetermined. Both our parents were happily making plans for a gala wedding.

Toward the end of my senior year at a prestigious upstate formerly all-women school, a few of us decided to rebel against the strict Protestant upbringing that had been our typical past. Ok, lots of kids do that, but perhaps the higher you are on the artificial rungs of society the further you have to descend to prove your independence. At least, that's how it seems. Of course, I didn't really think it would be so dangerous when we decided to head down to the city and explore the darker side of the Village. Just a little rebellion, that's all.

That's where I met Sly. Oh, I knew he was no prince. He was unkempt and shifty, but hell, I was out to prove something. He said he'd love to show us places in the Village and score some good weed. Amanda, the only apparently sane member of our group, balked.

"You guys are nuts! What do you know about this guy? Who knows what he could get us into."

"Oh, Christ," Sly said. "What a bunch of princesses! You're so used to your privileges you don't dare take a chance. If I showed up in a limo, you'd jump to go with me, wouldn't you. But no, I don't look all-college, so why trust me. Go fuck yourselves then."

Well, that was a challenge we couldn't turn down. We would show him we weren't some stuck-up society girls. I wasn't sure how the other girls felt, but I was scared. But I figured dammit if you're going to go adventuring you gotta go adventuring. And being scared is just part of it. Oh boy, what a dummy!

"Oh come on," I said. "Don't be a bunch of pussies. I'm here to have some fun. Are you with me or not!" That's me, the ringleader. Jeez! But I guess I was persuasive enough.

Amanda told us what she thought of our 'adventure' and left to go back to school. Sly called a few of his buddies and all of us bar-hopped for a while until we were all pretty well oiled. I suppose I could offer that as an excuse, but I think that the real reason we all went to that fleabag hotel with Sly and his pals was we kind of felt committed by then. So yeah, we fucked. And no, it wasn't great. I think I passed out while some guy was slobbering into my pussy. Anyway, by morning we found ourselves alone and deserted, our pocketbooks rifled, our credit cards and valuables gone.

We swallowed our pride and called Amanda to come and get us, swearing her to secrecy and vowing to each other that we'd just swallow our losses and never mention the escapade again. To be safe, we all went to health services to get checked out for STDs, and then cancelled all the credit cards. That seemed to be the end of it, until a couple of weeks later when I didn't have my period. Oh shit! I did the test, and sure enough, one of those bastards must have fucked me bareback and I was knocked up good. So much for birth control pills!

Clearly, I needed to get rid of the baby before I began to show. Unfortunately, I had no-one that I could trust who also knew a no-questions-asked abortionist. There was only one place to go. I swallowed my pride and my anger and tracked down Sly.

"Not my problem," he said helpfully. "I never laid a hand on you."

"That's not the point," I said. "I'm willing to pay. I just need it done quietly, and soon."

He allowed as how he'd get back to me. Next day I got a text from him with a phone number. I made the call. I don't need to go through the details again here, but the job got done.

Now, I thought, I could put all that behind me and get on with my life.

Of course, it didn't turn out that way.

About a month or so after graduation, just when I was newly set up in my own apartment in the city working at my new job, and all seemed to be going according to plan, I got a text from Sly, which included some truly remarkable pictures of me lying there on the bed naked, legs spread wide, with this Black guy's head deep in my crotch and at least more than one person's cum decorating my chin and breasts. And if that weren't enough, the text included a copy of a bill from the guy who had done the abortion!

Sly's text just said "Give me a call when you get a chance. I could use some help in picking out the best pics to send to mom and dad. If you need help paying this bill, your kid's dad will help, though he's pretty pissed that you didn't let him know, and he's threatening to take you to court over it."

Well, I clearly was hooked, and good. One fucking (so to speak) night and my whole life was in ruins. I like to think that I've shed the prejudices I grew up with in our lily-white Connecticut town, but I knew that that little vignette of racial harmony would not sit well with my parents or others whose opinions of me mattered. I had no choice. I called Sly.

We arranged to meet at his place in the city. Not a bad place: a couple of rooms in a moderate apartment building on the west side, sparsely furnished with a bed and a dresser in the bedroom and a couch and a few chairs in the living room, a small kitchenette that looked like it had never been used. Two windows curtained over. He sat me on the couch and there he laid out the terms for me. He told me the price for the pics and associated material. Well, it was clear that there was no way I could come up with that kind of money without raising all kinds of questions.

"Well then, honey, I guess you're just going to have to work it off. For starters, I could use a good blow job." (Sly was all class!) "Take off that blouse and let's see what you got.".

Well, it wasn't like I never heard of blow jobs. I'm not a virgin, for Pete's sake. I mean, I'd given hand jobs before, but then only for guys I'd liked and whom I could satisfy that way. I'd always avoided the oral stuff, though. It seemed pretty humiliating and frankly rather messy. But I couldn't see any way out of it now. First time for everything. So, like a good girl I unbuttoned my blouse and took it off under Sly's watchful eye. He whistled in appreciation, and then told me to stand still while walked around me. He took off my bra.

"Jesus,", he said, "you got a real rack, Babe," and he proceeded to help himself to my chest, cupping my breasts and licking and pinching my nipples until the little traitors got hard. "Ok, assume the position." I must have looked blank. "Down on your knees, dummy. Now." So I did. What else could I do?

First, he took my hair (I was wearing it long in those days) and brushed it back so as to have a clear approach to my face. Then he played with my mouth a little, parting my lips and sticking his fingers into my mouth to wet them, then rubbing my own saliva on my lips to lubricate them. He stepped back and dropped his pants, real slow-like as if to give me a show, which I sure didn't need. I mean, a girl can't get through high school much less college without seeing a cock or two, especially if she's pretty and has a great bod (yeah, like me. Deal with it.). But man, this one was huge! How the hell I was supposed to get that thing in my mouth I had no idea. I guess I looked shocked.

Sly just smiled and said "Nice one, hunh. Gonna stretch that tight little upscale mouth of yours a bit, but trust me, once you get it in there you're gonna love it."

He stroked his dick until he got some pre-cum. He wet his fingers with it and then spread some on my lips and pushed his finger into my mouth so I could taste it. With that he moved in on me and put his hot dick right up against my lips, wetting them more with his pre-cum. It was pretty scary. I just knelt there, afraid to move, while he pushed his hips toward me and held my head so I couldn't pull back. The next thing I knew that big cockhead of his had shoved my lips apart and was pressing hotly against my teeth.

"C'mon, girl," he said. "Open up. Relax, you're gonna like it. Trust me." Yeah. Sure. But I had no choice now but to get it over with to get my freedom back. Besides, I mean, how bad could it be? Some of my friends had done it, and a couple of them declared that they actually liked it. And, I have to admit, I was kind of curious. So I did as I was told and opened up.

Sly wasted no time. I felt my lips stretch as that big head forced its way past them, riding on its own pre-cum. Then they relaxed a little when they got on to the narrower shaft. Before I even realized it the damned thing was maybe three inches or so in my mouth. Jesus, it slid so easily over my lips! I could feel the weight of it sliding along my tongue and resting on my lower lip, like it belonged there. To my surprise, though, it wasn't really all that unpleasant. I mean, it was so alive, pulsing with energy. It was soft and smooth on the outside, but I could feel the stiff and solid core to it just under its surface. Pretty special, actually. I could feel all the little bumps and irregularities of the shaft as he kept probing into my mouth. Finally, thankfully, he stopped before he got to my throat and just waited while I got accustomed to the presence of his cock in my mouth.

"Good girl,", he said. "You're doin' fine, so far. It feels real good in there, don't it? Nice and fat and warm. And full, too. Now, you just relax, and I'm gonna make your day."

With that, he starts sliding in and out of my mouth, never taking the head of his cock out. Pretty soon my mouth starts watering and that makes his cock slide easier and makes me more comfortable. I was starting to get used to this, so in spite of it all I did relax a little and began to explore the new sensations I was feeling. The first thing that hit me was that it was actually sexy! I could feel my breasts getting harder and there was an undeniable tingling in my clit, and I knew I was getting damp down there. I really wanted to reach down and rub myself, but I didn't want Sly to get the wrong idea, so I just moved my thighs a little and hoped he wouldn't notice.

Well, Sly kept stroking in an out, sometimes faster, sometimes slower, and sometimes he would just stop for a couple of seconds. I could hear him breathing harder and harder, and when he put both his hands on my head to steady it I could feel the tension in them building. His arousal was getting to me, too! I started sucking on him, a little tentative at first, then getting more into it. We were kind of building off one another. Pretty soon he was gasping, and I knew any second, he was going to cum in my mouth. At that I got a little scared again because I had no idea how much cum he had for me, what it would taste like and whether I could handle it or choke on it. Was I supposed to swallow it or could I spit it out without pissing him off. By then, though, he was beyond caring about anything but his burgeoning orgasm.

That's when he really grabbed my head and shoved his cock pretty deep into me and held it there. I heard him moan and gasp, and with my lower lip I felt the big vein on the underside of his cock swell. The whole cock seemed to swell and get heavy with the sperm he was about to pump into me. And then he came! I felt his semen shoot out of the tip of his cock and hit solidly on the roof of my mouth. It seemed so hot! But it was followed immediately by more, and in seconds my mouth was filled with his salty-sweet discharge. God, there was a lot of it! With his big cock filling my mouth I didn't dare swallow for fear of choking. My cheeks puffed out and his sperm pooled on and under my tongue. Some began to leak out past my lips embracing his throbbing prick. I felt the warm discharge run down my chin and splash onto my breasts. Still he didn't stop cumming. Damme if I wasn't by then caught up in the frenzy myself. All his panting and moaning accompanied by the heavy cock pulsating and squirting his semen into me really got me fired up so I nearly came myself! All I needed would have been a touch on my clit to set me off. Hell, this wasn't bad at all!

I have to admit that I felt somewhat disappointed when at last his ejaculations eventually stopped, the last just oozing out and slipping almost casually onto my tongue. By then my head was swirling with all these new sensations. Mixed in was a bizarre sense of pride that I had taken that great big cock in my mouth and brought it to a frenzied climax, all on my own, and took his copious load, too. I must be quite the woman.

Sly left his cock in my mouth for a long time after he stopped cumming, just breathing hard, his hands resting on my head so I wouldn't pull away. Truth to tell, that was ok by me, I wasn't in any hurry by then. I was still sorting out my reactions. But at last, he backed off and the big thing slipped out of my mouth and slowly began to deflate even as I watched. It dripped some sperm that I had missed, but I still had a respectable mouthful remaining. I swallowed most of it in one big gulp and felt the warm mass slide easily down my throat and land in my stomach. My mouth was full of his taste, and I could feel it cooling on my chin and breasts. To my surprise I didn't even feel sick, just kind of warm inside.

"Sweetie, for a princess you're not a bad cocksucker," Sly said. Believe it or not, at least at that time I felt a perverse pride when he said that. But then I was still pretty confused by all that had happened in the last few minutes. I gathered what I could of the shards of my dignity.

"Good," I said. "I hope you're satisfied. Now let's have those pics and the other stuff and I'm outa here."

I had a feeling it wasn't going to be that easy. And it wasn't.

Sly looked at me with a kind of amused disbelief.

"Jesus, Princess, you have one hell of a high opinion of yourself, don't you. You were good, but just how much do you think one blow job is worth? I mean, I could get sucked off by a professional for maybe hundred bucks, and you're just an amateur with a lot to learn. A good one I admit, but still an amateur. Maybe fifty bucks or so? You owe me a hell of a lot more than fifty bucks. So, darlin', if you're gonna work it off with your mouth you got a lot more suckin' to do, don't ya think?"

Now I was really angry. "You're a real bastard, you know that? I did what you asked, and now I want my stuff. I'm not gonna spend my life sucking you off, you son of a bitch."

Sly smiled and made a placating gesture with his hands. "Now, now, honey," he said. "Much as I enjoyed that (and I know you did too), there's a limit as to how many times I want it. Not, I'm afraid, enough times for you to work off what you owe me. However, I'm sure we can work something out. I've got some friends who would just love to meet you. And hell, maybe you could even do some free-lance work to earn some extra. Plenty of guys patrol the streets and bars around here lookin' for someone like you. You'd be surprised how fast you could work it off if you're willin' to work hard at it."

And that's how it all started.

Sly had me come back to his place a week later, after work. All week I'd been dreading this, but I really couldn't see any way out of it without him ruining my life forever, so I resolved to do what I needed to do. I dressed as demurely as possible, took a cab to his place and rang the bell. He let me in, looking me over from head to toe and smiling to let me know that he knew exactly why I looked as I did.

"Glad you showed up, luv," he said. "You really are as smart as you look. I think we're gonna make this work out just fine. But first, get out of those clothes and put this on." He handed me a package that felt much too light. My heart sank. "Go on, go into the bedroom there and put it on."

In for a penny, in for a pound, they say. I had always been taught that if you commit do doing a job, however distasteful it might be, you just do it and get it over with. But when I opened the package I nearly fainted. The handful of material that was in it was silky black, nearly transparent nylon. The panties had a split in the crotch and the top tied at the front with a simple bow. No bra. Shit! It looked like a Victoria's Secret wet dream. Why guys needed all this stuff just to get off was beyond me. Oh well, whatever it takes to get through this, I thought.

When I came out of the bedroom Sly's eyes got real wide, and I felt more naked than if I didn't have anything on at all. But I'd be damned if I'd show him. So I smiled back and sauntered over to the couch and sat down and crossed my legs as casually as I could.

"Jesus Christ, you look good in that," Sly said admiringly.

"Yeah, well thanks, I guess. But if you don't want me to spoil it by breaking out in goose bumps and turning blue, you'd better turn up the heat in this place. This isn't the warmest outfit I've ever worn. And by the way, you got anything to drink around here?" So cool, I was.

"Sure, Babe," he said. "I don't want you getting looped before we even get started, but maybe a good shot of Vodka'll set you up." Like I didn't know that vodka wouldn't leave a trace on my breath. But he did pour me a stiff one.

I expected him to get down to business soon, but we just sat in awkward silence for about ten minutes or so. He glanced at his watch a couple of times, and then the doorbell rang. He got up and started for the door, but then stopped and turned around and looked at me very carefully. He reached over and rearranged my hair a little and pinched my cheeks to redden them a little. After another inspection to admire his work, He walked over and opened the door. In came this well-dressed good-looking Black guy. They shook hands, and then Sly pointed me out to the guy, and said "So, what do you think? We even?"

The dude looked me over with a critical eye like I was a new car or something. I guess I passed inspection. "Maybe," he said. "If she's as good as you say she is."

At that Sly brought the guy over to the couch where I was sitting. "Okay," he said, "Let her see it."

At that the Black guy unzips his pants and pulls out his cock. I'd never seen a Black cock before. It looked pretty big even though it wasn't stiff.

"I dunno," he said. "She looks scared. You sure she's good?"

"Trust me," Sly said. Then to me he said "Okay, now, you're on. Reach up and touch it."

Well, I was a little scared and a little in awe and a lot shy, so I hesitated and then reached out as far from me as I could while I scrunched back into the couch and rather tentatively touched the guy's cock. It was soft and warm. It looked harmless enough, and its mahogany color was actually kind of attractive. I lifted it up a bit and looked at it, turning it from side to side like I was some kind of cock inspector. What a dummy. But whatever, tentative or not, my touch worked, and that cock started to rise up and get fat and hard. Magic touch, I guess.