A Night to Remember

A Night to Remember

I had experimented with crossdressing for years. First swiping a pair of my wife's panties, then when I found how excited I got, buying my own selection of feminine underwear. It's not a giant leap from dressing up as a woman to wanting to experience sex with another man. Even while I was still married, I had fantasies about gay sex. My wife and I had gotten less and less active in the bedroom, to the point that our sessions were more work than fun. So, I ended up looking for my own fun and as long as that didn't involve another woman, she was happy with it. She had no idea of how far I would take it, but we ended up splitting not long after that.

On my own for the first time in years and with no restrictions on following up on my fantasies, my adventures began. I started slowly at first, dressing at home, from just lingerie to full regalia. Make up was a bitch, getting it applied and not looking like a clown in a circus was a challenge, but with practice I got fairly good at it. I didn't dress every day, just occasionally at first, when I found myself getting really horny. After a few months the sessions began changing for me, they were less and less satisfying and I knew I was going to have to step things up.

I again started slowly, with wearing panties under my regular clothes then pushing it further to wearing a bra and stockings. This peaked out after a month or two, requiring me to up my game again. At this point I'd not explored actual sex with men, but the rate things were changing I knew that wasn't going to last much longer. I was about to begin a whole new life style.

My first experience was at a local book store, the kind with the booths in the back. I had to checked several before I found one that didn't smell like a bad time and had the kind of peep shows I was looking for. I soon stumbled on a small store, quite, but still rather active in the clientele area, lots of patrons at night especially on the weekends. I dawned my sexy panties, slipped into some matching stockings and headed out. After I arrived at the store, I moved to the booths, found one showing man to man sex and settled in to wait. I had checked out the booths before and found they all possessed a classic glory hole, so knew someone would be along.

I wasn't long before a neighbor entered the adjacent booth. A video was showing in my booth and I soon heard a video start up in my neighbor's booth as well. I peered through the waist high opening and was pleased to see my neighbor had freed his cock and was slowly stroking it. I guess my attentions were noticed, because he stirred, standing up, he quickly slipped his cock through the hole. Here it was, my first real cock, time to put up or shut up. I reached up and took his hard member in my hand. The firmness of it was intoxicating to me. I slowly stroked it and felt his immediate response. His cock began pulsing as I stroked him, but I knew he'd soon get bored if I didn't take the next step.

I leaned down and tentatively, ran my tongue over the swollen head. I was rewarded by a moan from the man. I was apparently getting it right. I ran my tongue down the shaft, flicking it back and forth, then slowly worked my way back to the tip. Now was the time, I opened my mouth and closed my lips around the head. I was rewarded again with an even longer moan. Then I slide my mouth down along the shaft taking most of his cock. He wasn't overly large, maybe 7 inches and not too thick. This turned out to be easier than I had feared. I began working his cock with my mouth until I felt him begin thrusting with my rhythm. I knew he would soon be cumming and I was faced with my next big decision, was I going to let him cum in my mouth. My indecision left me open for a surprise that negated my preference, because I soon felt his cock begin spurting hot thick cum down my throat.

He seemed to have an endless supply as I lost count of how many times his cock pulsed, spewing cum with each pulse. As if I had been doing this for years, I swallowed and suck every drop he had to offer. The taste was amazing, salty and musky. The scent filling my nostrils lit a fire inside of me. My own cock was responding now, rigid and pulsing, demanding attention, but I had to finish what I had started before I could take care of myself. I had stopped sucking when he started cumming, now I gently began milking his cock, trying to get just a little more of that heady nectar. I could hear his harsh breathing and I knew he was spent. He pulled back and his cock slipped from my mouth with a soft plop.

It had been almost disappointing that it was already over. A funny thought entered my dazzled brain. More than once in my life, I had heard a woman say, "Is that it?" I could never fathom what they meant by that until now. Well I wasn't done for the night, not matter how much I wanted to retreat to my home and satisfy myself, I'd had my first taste of cock and I would have more before I was finished. Three more neighbors had their nights joys before I finally gave up and headed home.

I spent many nights waiting by glory holes for my next meal of hot delicious cum, but even this started to get routine. It was time for another change. It was time to consider my next step. Before I could take my next leap into gay sex, I needed to prepare myself. I had seen enough videos and managed to find reading materials on how to prepare, because I was ready to have a man slip his cock into my virgin ass. I had made up my mind that I wanted it long ago, but I hadn't worked up the courage to more than fantasize about it, until now. My oral expeditions had provided me with the incentive I needed. Those cocks spurting delicious loads of cum in my mouth had to be even more pleasurable when you felt them exploding inside of you.

I hit some of my usual spots, only this time I was after training materials. I need something to practice with and I knew I'd need to start small and work my way up. Though my first cock had been average, I had run across a couple that I had difficulty getting my lips around, much less in my virgin hole. I had no idea what my first anal experience would be like or who that lucky man would be, but I needed to prepare in case I got more than I bargained for. Now even though I was shopping, that didn't mean I couldn't drop in for a snack once in awhile. Though I had visited a number of shops, I never really paid much attention to the other goodies they sold. I had no idea how many variations there could be, but I worked through my amazement and eventual had several different size dildos, from small to OH MY GOD! Need to be prepared!

I spent the next few weeks working my tight hole until I could easily accommodate a fair sized cock. Ready now, I began my search. The glory hole thing was out for this. I knew guys did that but it was a complete turn off for me, so I turned to the clubs. There weren't many gay clubs in town but there were a few and I spent time in every one of them. After a couple of weeks I began to realize I was back on the dating circuit again, but this time I was the prey and the hunters were few. I wondered if women had the same issues when they dated. Another week went by before I got my chance.

The guy wasn't anything to write home about but he wasn't unattractive and he was interested. He'd bought me a few drinks and finally worked up enough confidence to ask me if I'd like to go some place quite with him. Rather than answer verbally, I slipped my hand to his thigh then to his crotch, giving his stiffing member a little squeeze. Well some place quite turned out to be his car, but after three weeks I was desperate. The whole thing didn't' last very long and neither had he. His cock was luckily another average one, so when he entered me there wasn't much pain. He pounded my virgin hole for several minutes before grasping my hips and thrusting hard. His cock exploded inside me, filling me with his hot seed. I knew I had been right, the feeling was much better, even if there hadn't been anything magical about it.

I kept up the pace and ended up having several more encounters over the next few months, a couple of them were regular dates. Most of those ended up in my bed and were far more pleasurable than the first. I hadn't broached my desire to dress for most of those men, but did explore that with one in particular. His name was Allen and he almost creamed his pants when he found out. We had great fun together and I got to fulfill most of my fantasies about dressing as a woman. Allen would even spend the night or a weekend, where I would play as his mistress, satisfying his every sexual desire.

Time moves on and so did my desires. I still had fun with Allen and a few others, but I was getting that old itch again, time for something new. I continued to satisfy my need to dress, to the point of dressing in public. I got a kick out of watching guys give me that look. Girls know the look. The one where the guy was trying to imagine how she'd look naked and attached to his cock. The looks often made me smile realizing they had no idea I wasn't what I appeared to be, but a few, well I had to wonder myself, just what it would be like to be attached to their cocks. Still, this wasn't the next step I was looking for and I wasn't sure I wanted to live as a woman. What I was looking for was pure sex, complete sexual abandon. When the time came, it came at me without notice and I even surprised myself.

I had gone a couple of weeks without a man and was getting pretty horny, so I decide it was time to at least find me a nice cock or two sate my desire for some cum. I decide on this evening to dress in my sexiest panties, stockings, garter belt, and bra, then head to one of the local adult theaters to see what I could scare up. On this night, I wore a loose pair of slacks and just to be different, a loose satin shirt. Sort of feminine but still a man's shirt, I was ready or so I thought.

I had begun painting my nails when I dressed. Though my nails were short for a woman they were longer than most men's and mine were painted pink. I had forgotten that until I was paying for my ticket. Well too late now and just maybe that would get someone's attention. I found a seat and settled in to allow my eyes to adjust to the darkness. These places were very dark except for the light for the movie screen, no other lights were present to accommodate the patrons. After a time my eyes adjusted and I started checking out my fellow patrons. There was a couple on the back taking care of business as if they we all alone, but it was a little early so there were not many other people here yet.

After 30 minutes or so, traffic picked up and I noted a few possibles seated alone. I casually left my seat and picked one of my targets and asked if he'd mind if I sat next to him. His smile said it all and I took my seat. The film turned out to be one of those almost X-rate ones with not much happening. Still I noticed the bulge growing at my friend's crotch and decide it was time to act. I rested my hand on his thigh and when I wasn't rebuked, I began sliding it towards his bulge which was getting even larger. When my hands finally touched his stiff member a moan escaped his lips. I smiled at him and began messaging his hard cock through his pants. He adjusted his legs to provide me better access and I switched hands so I could get at his zipper.

I soon had him free and was pleased to find that he had a nice 8" uncut cock, my favorite. I looked him in the eye and slowly licked my lips. His smile told it all, so I leaned over and began sucking his cock. His hand rested on my head as I work his cock down my throat. The deep throat thing I picked up turns out to be very exciting for most men and this guy was no exception. As soon as his cock slid into my throat he groaned loudly and I felt his cock begin to pulse. His hot sperm explode from his cock as I greedily sucked down every drop.

When I finally came up for air, licking my lips and swallowing the last of his sweet juices, I was greeted by his nice smile again. This time he leaned forward to whisper, "I had some great blow jobs in the past, but that one was the best I ever had. You suck cock like a woman." That brought a knowing smile to my own face. He straightened up his clothes, rose and left, so I turned my attention to finding my next victim and I spotted him just a few seats away. As it turned out he'd been watching and had a raging hard on. Seeing it trapped in his pants I asked if it was painful and maybe he should let it out. No sooner said than his cock was airborne and my lips were seeking it's pulsing warmth.

My newest conquest wasn't satisfied to just sit back and enjoy, he felt the need to explore my body while I explored his cock. He ran his hand over my back, then I felt him hesitate as he discovered my bra. I stopped sucking him and looked up. I found him staring back at me with the eyes of a kid on Christmas morning. A smile spread across his face and his hands slid to my loose shirt. Two buttons and my bra was visible. He slid his hands down my chest until they rested beneath my bra as he twirled my nipples. This sent a tingling sensation through me and he obviously picked up on it.

He leaned forward pressing his lips against mine. My lips parted and his tongue slid quickly inside. This was no ordinary kiss. This guy could kiss and he enjoyed what it did to the ones he kissed. My body was practically vibrating when he finally broke the kiss. He whispered asking me to stand up, which I found myself complying before I knew it. Standing in front of him, his fingers found the last button on my shirt and he pulled my shirt apart. His hands danced over my skin finally ending up beneath my bra, his fingers gently tweaking my nipples. I bit my lip and moaned as he worked my nipples, then I felt him undo my slacks.

I had chosen them for just what they did, as soon as he had unfastened them the dropped to the floor, exposing my sexiest panties, garter belt, and stockings. His smile broadened, as he stood slipping his hands around me pulling me close to him. His lips found mine once again and he kissed me deeply. I felt his hands slide behind me to cup the cheeks of my panty covered ass. He gripped my cheeks pulling me even tighter against him grinding his rigid cock against my belly. His cock was pulsing by the time he broke away, he worked his way behind me and slid my panties down. His hand slid down, his fingers searching and finding my now wanton opening. He lubricated one finger slipping it into me and probing my depths. His lips found my neck and kissed it gently, finally ending up near my ear where he whispered he want to fuck me.

I couldn't find words, it was if I had forgotten how to talk, I simply gave his rock hard cock a gentle squeeze and before I knew it he had me bent over the seat, his cock sliding easily into me. As he began thrusting his cock into me, something deep inside of me released. An insatiable need began growing inside of me. Spurred on by the cock now pounding my tight hole, the smells of the sex all around me, and the fact that I had allowed a man to strip away my protection and expose the real me. I was lost in my wanton desire for sex.

I closed my eyes and relished the treatment I was receiving. I had to rest my hands on the seat in front of me to keep from toppling over the seat from the pounding I was getting. Moaning loudly, begging him to fuck me deeper and harder, I took almost no notice when a cock appeared in front of my gasping mouth, I just consumed it, sucking it deep into my throat wanting more of it, even after my lips rested in the soft hair at its base. I felt hands gripping me hard and final deep thrust as the first man shot his load deep inside me. I felt each pulse and resulting fountain of hot liquid. It's warmth filling me and stoking the flames of my desire. My thoughts turned to the cock in my mouth, sucking harder and faster, wanting to taste it's musky fluids, hot and fresh.

At some point the first man slipped from me and almost without notice, that emptiness left by the previous cock, was filled as another slid into me to take its place. I lost all sense of time at that point, lost in world of hard cocks. Cocks in my ass, cocks in my mouth, and cocks in my hands. They seemed to be endless and I didn't care. All I wanted was more. At some point the activity subsided, my whole body seemed to be covered in cum. The last cock had just retreated leaving my hole dripping. The cum oozing out of me soaking my stockings and pooling on the floor beneath me. I wiped at the cum on my face and when I looked at my hand, I could think of nothing more to do than lick my fingers clean.

I found myself alone, seated now, exhausted. Somewhere in the melee, my own cock had added it's own juices to the rest. As I licked my lips savoring the heady flavors of cum, I began to realize what had happened. As quickly as I could, I gathered my clothes and arranged them as best I could, rose and left theater. The drive home allowed me to clear my head even more and take stock of what I'd just done. My pants were soaked with the cum oozing out of my ravaged hole. My chest, neck and hair were covered with sticky drying cum. I couldn't recall much of what occurred after that first thrust of a hard cock, but I knew there had been many men. It seemed that once my nature was revealed, every man in the place wanted to have sex.

I soon arrived home and headed to the bathroom to clean up. I ran a hot bath to soak my aching muscles and ease the pain that now radiated from my soar ass. I lay for a long time in the hot soapy water, the heat of the water and the scent of the clean soapy water relaxing me and clearing my head. I had been violated. I had allowed myself to be violated. I couldn't exactly call it rape because I had wanted it, relished in the feel of every moment of it. Just the thought of it now warmed the fires inside me. But I knew what had happened had been dangerous beyond all else.

I knew also the wanton abandon I had felt, the countless hard dicks, and the endless spurts of hot cum, was something I desired to experience again. I was certain the exposure of my feminine side was what had set off the blaze of hot sex. I knew I would do it again, if the chance arose. I also knew that I couldn't allow another incident like tonight's to occur. It was amazing, wonderful, and exciting, but the uncontrolled nature of it, the random participants, was far too dangerous. But........... If I could plan and pick the men, well then.......................