The Wild Night

I was visiting Newark, NJ on business for a couple of weeks. This was my chance to act out a couple of sissy whore fantasies I had been entertaining for a long time, and I intended to take full advantage of the free time I would have every night after work.

I spent the first couple of nights gathering up what I would need. First I visited a thrift store and did some shopping for clothes. I found a cute little pleated tennis skirt in my size that was just adorable. It was white with a thin line of red and blue trim about half an inch up from the bottom edge. It was just long enough to cover my ass, and not a lot more. I also found a very light weight blouse that was almost completely see-through. There was a nice little silky camisole. I also picked up a men's golf shirt and a pair of khaki shorts, along with some cheap sneakers in my size. The last thing I found was a small purse, just big enough for what I had in mind, with a little thin strap. I already had a pair of 3" high heels that fit me, carefully tucked into my luggage before I left home.

A couple more stops got me some matching red lipstick and nail polish. I found a cute little lingerie set with matching red lace panties, garter, and bra in a size close enough to mine that I could make it all work. I went to Wal-mart and picked up a box of condoms and some lubricant, as well as makeup and nail polish remover so I could be presentable at work and not arouse any comment. I also found a couple more panties that I liked. Finally I added an enema kit to my cart. The woman at the register gave me a knowing look that fell somewhere somewhere between amused and disgusted when she saw the collection of things I had in my cart.

After work I returned to my hotel and showered, then applied nail polish to my toenails and fingernails. I slipped into a pair of panties and bra, but put the garter belt, nylons, and heels in my purse along with a few condoms, the lube, and the lipstick. I put on the skirt and then the shorts, then pulled on the golf shirt over my bra and slipped on my sneakers. I was more or less presentable as a male, at least at night under casual observation.

It was a ten minute drive to get to the area of town where there were a couple of porn theaters. From my online research I knew that one was reputed to be more heavily frequented by black men than the other, but I planned to check them both out. The first was fairly tame, and there wasn't much going on there. I hung around a bit and gave one guy blowjob, but left soon after to go to the other. It was a couple of blocks to get there, so I just walked and left my rental car where I had parked it after retrieving the purse. I left my wallet hidden in the car, and just took some cash in my purse. The area was all offices and businesses that were mostly closed, so there was very light traffic. I carried the purse in my hand so as not to be too obvious.

The second theater had an interesting layout. The first floor had two good sized theaters, one showing straight porn and the other showing gay porn. Up a flight of stairs was another, much smaller theater showing gay porn. I checked out all of them over the next half hour or so. The large gay theater had a fair amount of activity going on, mostly just discreet stroking and blowjobs in the rows of seats. One white guy came and sat next to me, taking his cock out as soon as he sat down. He had a nice sized cock, circumcised and with a large mushroom head. The blowjob I had given at the other place had only whetted my appetite for cock and cum, and I was soon on my knees giving him head. I slid my tongue slowly up and down his shaft, at the same time checking to make sure it was nice and clean and showed nothing that would indicate it would obviously be unsafe to suck him off. Once satisfied, I swirled my tongue around the head a few times before engulfing as much of his throbbing dick as I could. I have never been able to get past my gag reflex, so I don't deep throat but I took as much of him as I could. I gently massaged his balls while I sucked on his cock, which got me a low moan from him as my reward.

After a couple of minutes I slipped my hand up under his shirt to caress and gently roll his nipples between my fingertips. That was pretty much all it took to take him past the point of no return. He only lasted a couple of minutes more before blowing his load in my mouth, which I of course dutifully swallowed. He rested for a few seconds, mumbled a hasty thanks and left.

That scenario repeated itself one more time before I moved to the back row. At least I had planned to move to the back row and sit there, but it was soon obvious that there was another job for my mouth in the rear of the theater. I noticed that there were three guys standing with their backs against the back wall of the theater, two of whom had their cocks out and were openly stroking. The one in the middle was hard and massaging his cock through his jeans.

I knelt in the seat directly in front of the first one and leaned over the back of the seat, taking the head of his cock in my mouth while he continued to stroke. The other two watched while I sucked. He soon released his grip on his dick and put his hand on the back of my head, face fucking me until he shot a load of his warm, sticky cum in my mouth. It was a very nice tasting load, and I swallowed it eagerly before moving on to the next one. This was the one who had been rubbing his cock through his jeans, but he had taken it out as he watched me suck the man next to him. This guy was black, the first black man I had sucked that night. His cock was well above average in size; not huge, but at least a good solid 7 or 8 inches. I loved sucking on him and was soon using both hands as well as my mouth. I was stroking his cock with one while I worked on it with my mouth, and playing with his balls with the other hand. Occasionally I would switch off, stroking his cock with my hand while licking and sucking on his balls. He lasted a good while. The third guy was now massaging my tits through my shirt, quickly discovering my lace bra. He tried pulling off my shirt, but I was not willing to release the cock I was sucking long enough to take it off. Eventually he settled for having it pulled up so he could see my bra, then started slipping his hand into the bra to play with my nipples. That just made me moan around the dick I was sucking, and give it even more attention.

About that time I could tell the man I was sucking was about to blow. His cock was getting noticeably stiffer and I could feel the head starting to swell up. Shortly after that he grabbed my head with both hands and thrust deep into my mouth, grunting "shiiiiiiitttt..." as he unleashed spurt after spurt into the back of my throat. It was all I could do to keep from choking, but mercifully he backed off just enough that I could swirl the mouthful of cum around his cock head before swallowing it all down. He let me continue to gently work on his cock until it went soft, finally pulling it out before he patted me on the head and left.

Telling the third guy to wait a minute, I stood up and made my way to the mens room to finish changing. I slipped out of the shorts and shirt and folded them up. I pulled the thigh highs and high heels out of my purse and put them on, then put a shiny coat of bright red lipstick on my lips. There was no doubt at all what I was or what I was there for now. I tried putting my "boy" clothes into my purse, but it was too small to fit all of them. I guess that was a little bit of a planning failure on my part. I decided to leave the shoes and just wear high heels for the rest of the night; I could always take them off if I needed to. The last thing I did before leaving the restroom was to use some of the lube I had brought along to lube my ass. I slipped a finger up inside to spread as much in there as I could, then washed my hands and left the restroom to go back to the theater.

The man who had been fondling my tits was nowhere to be seen, so I sat down in the back row and just watched the porno showing on the big screen. Over the next half hour a couple of men came over to sit next to me, and like a good whore I sucked their cocks and swallowed two more loads. Neither one of the men were in any way remarkable, but I felt I was doing my public service, providing some relief for middle aged married men who probably weren't getting laid at home. I sent them on their way with empty balls and a satisfied smile.

While all of this was going on, though, I had noticed that occasionally a man would enter the back of the theater, then disappear through a curtain in the back corner opposite where I was sitting. No light escaped into the theater when they did so, and I was getting curious. As there was no one using my mouth at the moment, I got up and casually swished my way over to the curtain and peeked behind it. There was nothing there but a very, very dark stairway. I decided to check out where it went.

When I say it was dark, I mean pitch dark. There were no lights at all, and once the curtain fell behind me none entered from the theater. I had to feel my way up the stairs, which was even more of a challenge with the heels! Fortunately there was a railing, and eventually I reached the top of the flight of stairs. By now it was absolutely pitch black without the slightest glimmer of light at all. I literally could not see my hand two inches from my face. It was also very quiet, with only a faint sound from the theater below. I cautiously felt my way around. There was a doorway, then the cool smoothness of a tiled wall. A couple of feet down the wall I discovered a metal structure and figured out that I was in a restroom, and had just found the wall of a stall.

Armed with that knowledge I kept feeling my way slowly around the perimeter of the room. My heels made a hollow click with each step I took that echoed oddly in the room. It was the only sound. There were three stalls, then a bare wall... and then a man. All I could tell was that he was standing with his back to the wall, and I could feel his arm slowly moving - he was stroking his cock! I dropped to my knees and took his engorged member between my lips, once again feeling the luscious smoothness of a hard cockhead slide into my mouth. I could tell by feeling my way around his crotch that this was a black man, and his dick was definitely above average. Long and thick, it felt wonderful in my mouth and I gave him the best blowjob I knew how. After a couple of minutes, though, he pushed me gently away and went back to stroking.

I continued along the wall. At one point someone flipped open a cell phone, and in that few seconds of dim light I could see there were at least half a dozen men standing around the perimeter of the room. As far as i could tell all were black, and most had their cocks out. One caught my eye, and I made my way toward him as the little cell phone screen blinked off and once again plunged the room into total blackness (in more ways than one). When I found the man I was going for, I reached down to find his cock... and gasped in awe. His was the single largest cock I have ever seen or felt in my life, either before or since, and I have seen and sucked a LOT of cocks. This monster was easily eleven inches long, possibly more, and at least twice as thick as mine. It was, in a word, huge. I immediately went to work on it, trying to stuff as much as I could into my mouth until I was gagging on it. There was still room for both of my hands on his shaft.

After trying to give him a decent blowjob, I knew I had to feel him in my ass. Thankfully I had bought Magnum XL condoms. They were the biggest I could find and I bought them not because I was expecting cocks like this, but because they fit most men rather loosely, and guys like thinking they need an XL condom. I rolled the condom onto his rigid cock as far as I could, and turned around. He had his hands on me as I did, and I felt him flip my skirt up and rub the head of his cock against my hole. I pressed back to let him know it was OK to enter me, then gasped and moaned as he slipped the big thick head of that pussy splitting tool into my ass. After a minute or so to get used to this invader stretching my ass, I pushed back a little more and he started thrusting into me. Now he had his hands on my hips, and with each thrust he was going deeper. I felt that monster cock slide further into me than I had ever been fucked before. It was uncomfortable, then it hurt, but I wanted to take it all. I didn't want to stop until he was balls deep inside me.

My moaning sounded so loud in the room that I was a little embarrassed despite the fact that no one could see me! At that point, though, I was past caring. My world was now centered around this magnificent, huge, thick black dick that was stretching my ass wide open as he drove into me time after time.

About that time I could feel that another man was in front of me. He rubbed his cockhead against my lips and I obediently opened them. Another black man, his dick was not nearly as big as the one now pummeling my asshole but was still impressive. It was very thick, and he was fucking my mouth as the man behind me plunged deeper into my colon. It didn't take long for him to reward me with another warm, sticky load of semen that filled my mouth, and of course I dutifully swallowed every drop.

By now the one fucking me was grunting as he plunged his huge dick deep inside me. Yet another man took the place of the whose cock I had just sucked and used my mouth as his personal cunt, sliding his big dick in and out as I played with his heavy balls. I was dressed like a street whore, in a dark room above a porno theater, being spit-roasted by two cocks, both black, and one of them the biggest I'd ever seen. The one in front of me stiffened and grabbed my head as he unloaded his balls into my greedy sucking mouth, spurting his load as fast as I could swallow it.

My ass was stretched wide by now, I could feel the big dick invading it, but more so I could feel the discomfort as he rammed the full length of that monster into me. His heavy balls were slapping against my own as my dick hung limp and useless between my legs, flinging little droplets of precum onto the pleats of my skirt. Another man took his place in front of me; this one was older, I could tell, and had a very thick cock about six inches long. I sucked him until my jaws ached almost as much as my intestines that the guy fucking me was trying to straighten out. The one in my mouth finally blew his load, and was quickly replaced by a fourth. I didn't know how many were lined up to use my mouth, but at this point I just wanted them to keep cumming!!

By now my world had narrowed to nothing more than the pummeling of my now slack asshole, the head of his magnificent dick plowing deep, deep inside me, and trying to keep suction on the big black cock that was throbbing and thrusting in my mouth. I could tell the stud in my ass was getting close; by now he'd been fucking me for close to fifteen minutes straight, long enough for me to have sucked off four other men! Finally the man fucking my mouth erupted with a torrent of jizz that I could barely swallow, and seconds later my ass-fucking master slammed the full length of that incredible cock into me to the hilt. I could feel him stiffen; he pulled my hips back to impale me fully on his huge dick and I felt it jerk and spasm as he ground it in deeper than ever. He pumped his load of cum deep enough inside me that it felt like he was halfway to my throat. He stayed there, grunting and twitching, until the last of his cum had been drained from his big black balls and deposited deep in my well-used sissy cunt.

We stayed that way for a few minutes, until his cock finally began to soften. He pulled it from my ass and I immediately felt empty and very thoroughly fucked. My poor asshole was gaping open from the stretching given to it by this huge invader. Once I could walk again I made my way back down to the theater, and realized that I had a little bit of a problem. Somewhere along the way, I had lost the clothes from my purse, and now it held only my lipstick, lube, and a few more condoms. I was two blocks from my car, which was parked on public street. By this point, though, I was so well fucked and so full of cum lust that I was past caring. After catching my breath for a few minutes, I slipped out a side exit and into the alley beside the theater.

Mercifully, there was no traffic on the downtown street. I started walking back toward my car. The sound of my heels click-clacking on the sidewalk and the warm evening breeze under my skirt felt wonderful. About halfway back I panicked as a car came into view, rolling toward me down the street. Here I was, a forty-something white guy dressed in heels, nyons, a white pleated skirt, and a lacy red bra... walking down the street in the middle of the night!! Knowing my luck it would be a cop! But it wasn't. I got a couple of less than complimentary comments shouted by the young guys in the car as it drove past, but other than that the walk was uneventful. I drove back to my hotel and managed to make it back up to my room without being seen.

I woke up the next morning still in my skirt and bra, with my heels laying on the floor next to the bed, and my poor abused stretched asshole still barely able to close. I didn't feel much like breakfast, probably due to the fact that I had swallowed nearly a dozen loads of cum the night before. I managed to get the remains of the lipstick and nail polish off before dressing and going to work.