Remember Yahoo Chat? I Sure Do

The news was unexpected. I can't say it was devastating. In fact, it elicited no truly emotional response from me whatsoever. But just a few months ago I was scrolling through my Twitter feed and a headline jumped out: "Yahoo Chat to shut down permanently."

I paused for a moment when I read that headline. Yahoo Chat. It had been probably ten years since I, now a 33 year old married man living the suburban American dream, had even logged in. Many of you reading this might remember the old chat application. If AOL Instant Messenger was the place for teenagers to awkwardly flirt with classmates in a way they could never muster up the courage to do so in person, Yahoo Chat was the seedy underbelly of the early internet chat world. It was anonymous. It could be local. Or it could fit pretty much any fetish you could imagine.

Growing up my very good, loving parents were a little naive. They left a young, curious and horny son alone in a house with the internet and no blocks whatsoever. I was caught looking at porn a couple of times and because my father had run into some trouble with my mother over the same issue a few years before, it was a tense subject that the family didn't feel comfortable discussing. They sent me, a young teenager, to a Christian sexual therapist to talk about my "porn addiction". I said all the right things and was deemed cured.

Within a few months - or if I'm being honest, probably a few days - I was back at it. I was cruising through chat rooms roleplaying and talking dirty, exploring my curiosity and pushing my boundaries with people I would never meet.

Then Yahoo Chat became a lot more real. It became something other than an imagination land.

I was 18 years old and a senior in high school. And the night before I had a little too much to drink (yes, even on a school night. Stop that judging, you!). So much, in fact, that I woke up vomiting. My parents, oblivious and perhaps in denial, called me in sick for school. So there I was alone at home, blurry vision and blurry thoughts with a little booze still on my breath.

What did I do, of course, but fire up the computer, pull out my cock and start to alternate between wanking, flipping through porn browsers and steamy roleplay chat rooms.

As I was searching the Yahoo Chat rooms I found the one for my location: North Carolina. I had never spent much time there because "North Carolina" is a big state and the rooms only held about 50 people, so even if I wanted to break my anonymity and dream world, the chances of finding a woman near me were next to none.

My user name at the time had my city as part of it. After watching some porn and beating off I noticed a blinking message from a user named "naafar". Naafar? Sounded weird.

I opened the chat box and fortunately for our purposes here I remember the conversation fairly vividly.

Here I was, a horny 18 year old into MILFs, busty teens and gangbangs, and here was "naafar," who turned out to be a 30-something year old black man from Africa who lived one city and 15 miles over. I could tell even through chat that he didn't speak the best English but he managed to get the basics of who he was across. Seemed harmless, but I wasn't gay so who cared?

But that's not the whole story. I was and am straight. Or mostly. Now we know there's a spectrum and it's never as simple as we think. I was also hung over. And I was probably still a little tipsy. I also had a raging boner and an empty house. So my decision was to humor this local African man and see what he had to say.

As we chatted I continued looking at porn. That means my hard-on was doing most of my thinking for me. When he found out I really was local, at home alone and so young he told me that he would love to come over. Instantly that raised red flags. For one, I WASN'T GAY! (But why did the idea have some appeal?). Also, what if my parents came home unexpectedly? And why would I let a potentially dangerous stranger into this house?

Here's where the story takes an even more twisted turn. "Naafar" started to become very explicit in his messages. He realized I was young, horny and impressionable and he told me exactly what he wanted. He said he liked that I was an overweight kid because that meant curves and a lot to love on and feel up. He also said he was wondering what I would look like dressed up in women's clothing. WOMEN'S CLOTHING!? At that point in my life I had never even thought about crossdressing except as it might have come up in jokes with friends.

Well, my hard-on and the booze won out over my inhibitions and normal preferences. "Naafar" told me to go into my parents room and pick out one of my mother's outfits. Lo and behold, I found myself doing it. Gosh, I felt so dirty but my dick stayed so hard.

I remember it clearly. I picked out a pair of shorter green pants that hugged my thighs and ass (my mother is in good shape so they were very tight on me). I also picked out a frizzy purple sweater with a V-Neck and built in cushioning in the chest that made my bust look something like a B or C cup. But I didn't stop there. I got into my own mother's makeup cabinet and picked out the deepest red lipstick I could find and put on some blush and mascara, just to satisfy my own growing curiosity.

Away from the chat browser but hearing the "ting" of his messages still coming across, I looked in my parent's bathroom mirror. I looked like a horny teenage sissy who wanted to come across as a hooker. I watched as I masturbated myself and felt my chest through the sweater.

Still tipsy and slightly hung over but more aroused than anything, I hurried back to the computer and without pausing to exercise any judgment ... I gave him my address. He quickly told me he would hurry over.

Those next 20 minutes were the slowest of my life.

I was terrified. What had I done? Who is coming here? Is he actually coming? Will we be caught? Should I change back to my normal clothes and tell him he has the wrong place? Are we going to mess around? Am I actually fucking gay? What would my friends say? What would my PARENTS say? Would I be disowned? No, my parents are loving people. But I would never have the same relationship with them, ever again, if they found out. What would the neighbors think seeing a dark African man, I assumed, slipping into our front door?

Eventually, sitting in that office with my penis now only half hard because of nerves, I heard a tap on the door. My heart was racing. My breathing elevated.

I was a virgin. Never with a man, never with a woman. I had wanted to be with women of course. I had a fiercely moral, evangelical Christian upbringing, so it would have been frowned upon and any fornication would have brought intense guilt upon my own conscience, but that didn't stop me from consuming copious amounts of porn followed by the same guilt after I would cum.

And I went to the door, opened in and let him in.

Here was "Naafar". He was about what I expected. Dressed in a very plain outfit, a plaid shirt buttoned up neatly and khaki pants. I couldn't even look him in the eye. I was so embarrassed. I wasn't even aroused. Because I was still dressed up like the curvy hooker boy taking orders online.

The next minute or so is a fog in my memory. We probably made small talk and very little of it. But I know I walked down the hallway and into the "third bedroom", the guest room. We had a low to the floor queen sized bed that took up much of the small room.

Once in the room, I stood idly by the bed not knowing what to do. "Naafar", as I'll always and only know him, stood a foot away from me. He was about 5'8, average build and a fade haircut.

I had never imagined that I would do anything with a guy. Much less a black guy. Now, to be honest, I had enjoyed a fair amount of straight interracial porn (who doesn't?) and I think any white male who picks those videos out probably fixates, at least a little, on the big dark cocks that are featured so prominently as the stars of the show against the contrast of their white female conquests.

I vividly remember the rest. "Naafar" didn't say much. He was quiet and shy himself.

But he was very gentle with me, at least at first.

He put his hand on my waist and pulled me close to him. Being 18 and dressed like a girl with full makeup, I just let him take the lead. I never made much eye contact. I was too ashamed even as my hint of excitement began to grow a little.

He put his other hand on my chest. Then both hands. His smooth black hands began to fondle my chest, which is naturally busty (even now after much weight loss) and was greatly aided in appearance by the sweater's padding.

What I remember most is his smell. My African guest was so close, I could distinctly make out a different aroma. He didn't smell good. It wasn't bad either. It was just different. All of this was so different, so foreign. It still feels like a different universe. But it was real. This man in his 30's continued feeling up my teenage male breasts and his breathing picked up. I could tell he was getting very aroused.

He put his hand on my shoulder and without saying anything pushed down. This was so new, but I knew what that meant. He wanted me to get on my knees.

I slowly obliged, first to one knee and then both. I didn't look up in his eyes although I can still feel his eyes looking down at me, chest jutting out and something between fear and desire on my lipstick covered face. I had watched enough porn to know how girls do this. But I was going to learn on the job.

My fingers found his belt and I managed to unfasten it even though I was trembling. Now I was also nervous because I found myself wanting to do it right. Naafar was very kind to me. He never said much at all, but his gentle prodding moans of approval and the way he used his hands were an encouragement and sign that he was pleased.

I unzipped his pants and opened them up. I half expected it to pop out right there but I had to go through his boxers. Even before I opened the slit in the front the musty smell of his pubic region emanated straight into my nose. I had never come close to experiencing anything like this. There was no going back.

I did look up once. I looked up to make sure I was doing it right before I took out his cock. His mouth was partially open and his eyes were tightened because of an intent grimace. This African man was totally ready. I knew then I was doing it right, indeed.

My hands fiddled and opened his boxer hole and there it was. A big black cock. It wasn't a monster like you'd see in some phony professional porn production. But it was probably a legit seven inches. There was a little curve to it. What I noticed was his pubic hair was different, just like a black man's hair is different.

Now was the moment of truth. My look hadn't scared him off. This man was definitely into me and into this. Emboldened and past the initial terrified feeling I instinctively reached deep into his boxers for the base of his cock and made sure to pull his manhood out in all its glory. I even mustered the courage to smile and say, "Nice."

I felt "Naafar" put his hands on my head and grip firmly but not too hard. Just enough to let me know he was in control, as if a first-time crossdressing 18 year old with everything to lose thought he was calling the shots.

Gripping the base, I began to pump my right hand gently forward, tugging his small amount of foreskin over the tip of his glistening, slightly moist black mushroom head. I'll never forget that moment of being maybe three inches away from a strong, horny black cock. The sight. The smell. How it seemed to throb and beg for release. It had its own personality, so much untapped potential and desire. I glanced over his balls and cupped them in my left hand, rolling them in his scrotum between my fingers.

As I stroked his cock to make sure it was fully hard, not quite ready to do more and not knowing the next step, "Naafar" reached down and began groping my chest again. He bent down at the knees and waist so slightly so he could cup my chest in his hands. It felt really nice. I'll also never forget realizing that his precum was getting thicker and there was more of it. It began to seep onto my own hand. The aroma was similar to what I would smell during those hundreds or thousands of my own private masturbation sessions, when I would blast my load into my hand before stumbling off to wash up.

I remember thinking something to the effect of, "Am I just going to jack him off? What does he want?"

He answered without words, seeming to read my mind.

Naafar's hands went to my head again and pulled me in.

It all happened too fast for me to even process what was happening. Certainly too fast for me to protest or pull back. If I had time to think I probably would have worried about STD's.

My mouth opened before my mind gave any instructions. And just like that, a stranger's middle-aged and erect black cock was in my mouth. Looking back, I like to imagine what I looked like to an outsider. The lipstick wrapped around him. Down on my knees, hands reaching around to hold his ass for support and to pull him in deeper.

I can't say I deepthroated him. I could take about four inches of his cock in my mouth before feeling like I couldn't continue. So I would pull back my head without taking him out of my mouth and slide back down on it. Most of the time my eyes were either closed, savoring the moment in disbelief or rolled back in my head. I knew that I had precum lodging itself in my mouth as he humped forward and I bobbed on him in rhythm.

I probably sucked Naafar's cock for about two or three minutes before he abruptly pulled out. At that point I became nervous. Was he about to cum? Did I do something wrong? Was he upset?

No, no and no.

What I'm about to tell you will make that 18-year old me seem completely naive and ridiculous, but hey, I was 18, horny and making bad choices.

Throughout our chat conversation, my crossdressing, our meeting and my first blowjob I had never even thought about the possibility that Naafar wanted sex. Real, actual anal sex. Had I thought that was a possibility I absolutely would not have gone for this tryst. Even with a condom. Without a condom, well, I would have known that would be stupid. Even with a condom I would have been terrified. My ass has always been tight and still is.

But Naafar, who had been so gentle and easy going to that point, didn't ask for permission. He was very horny, obviously, and muttered, "Get on the bed." Not in an angry or threatening way, but the message was clear. He wanted ass.

Here I got very nervous. I should have said stop. Or wait. Or something. But being so young and having let him go this far, my body was just doing what he told me. Part of me was just ready for this to end. I regretted it.

But in what was essentially a trance, gripped by the unknown and the newness of it and how fast everything was happening, I got on the bed. He manually moved my body around until I was on my hands and knees facing away from him. Then he hurriedly unsnapped my pants and pulled them down over my round ass just enough to be out in the open for him.

At this point in the story I must confess, for the sake of honesty, the limitations of what I remember. I wasn't even totally "there" in that moment. I couldn't believe it wasn't happening. What I do know is that Naafar put his hands on my hips and before I knew it I felt him pressing his slippery cock head against my ass entrance.

I clinched my teeth and my fists with the sheets between my fingers, pressing my face down into the bed's pillow and bracing myself for what I thought would be a horrible experience. I had never, absolutely never understood why gay guys enjoyed anal sex. It had just seemed like it would be such a needlessly, unnaturally painful and potentially damaging experience. "It doesn't even fit, the biology doesn't match up," I had said once before in explaining my opposition to man on man intercourse.

But here I was. Still dressed in that tight fitting sweater. Naafar reaching around to grab my tits while he forced as much of his cock in my ass as he could. I didn't resist. I just let him do what he wanted. He could have made it unpleasant but he didn't last long. After about only 90 seconds of pushing his head and a couple of inches of shaft into my very tight virgin hole he started to grunt loudly. It was the most noise he made during our entire meeting.

I knew what that sound meant. I don't remember feeling Naafar cum inside me and I don't know how much of a creampie he gave me. I do remember when he pulled out I felt some of his cum in my crack and for a couple of seconds as he came down off of his climax he moaned and slid his big black cock up and down my ass, smearing some of that creampie cum around.

He didn't say a word but left the room, only to return a moment later with toilet paper, which he used to wipe me up himself.

From there, it was awkward. The most awkward our meeting was at any point that day. Neither of us knew what to say. I was still somewhat horny because I hadn't cum, but I was mostly very self-conscious, now left with a man who wasn't horny and was looking at me dressed up like a hopelessly horny girl. I walked him to the front door, said goodbye and he left.

I never saw him again.