I know what you're going to say - not another Halloween cross-dressing story. But Halloween is a classic time for those of us who like to garb ourselves in the accoutrements of the opposite sex, and my last outing during that time was quite an adventure.
As I've mentioned in my previous postings, I'm a pretty typical example of the cross-dressing guy: tall, slim, professional, and for all outward appearances a regular everyday straight laced "Joe". But since I was just a kid I've always had a hankering to don a skirt and heels for fun and excitement. I only dress up and go out a few times a year, but when I do it I really enjoy it!
I consider myself to be "straight" - but over the last few years I found myself occasionally enjoying the company of men while I was dressed as a woman. The first time was really nothing more than a drunken tryst in a dark parking lot. A few too many cocktails at the local TG bar, a few hot dances with a persistent tranny chaser, and before I knew it I found myself bent over the hood of an SUV with my skirt pushed up, panties pushed aside, legs spread wide, and a cock stroking in and out of my virgin ass. Much to my amazement I found I enjoyed the experience.
The next time was a bit more deliberate. I had enjoyed my first time letting a man have his way with me while I was dressed in a skirt and heels so I wondered if I would enjoy it a second time. Curiosity led me to an ardent internet admirer who wanted a last "fling" with a t-girl before he tied the knot. We had conversed online for several weeks until I finally relented to his requests for a meeting. I invited him over and let him seduce me - sucking him off for my first taste of cum and then letting him lay me on my bed, spread my legs and ride me. I still vividly remember the feeling of my stocking covered legs wrapped around him, my nails digging into his bare ass, and the sensation of his cock pulsing as he shot his load deep in my ass.
Unfortunately, since those two encounters I've had little time to indulge my alternative wardrobe activities and have only managed to dress up and go out a small number of times. Grad school, work, and family responsibilities kept me pretty busy. Then I met a woman named Rita - a fiery raven haired Latina with medium brown skin, perfect 36C breasts, a tiny waist, round full hips, shapely legs, and a full set of kissable lips. Her hair is glossy and tumbles down in great curls past her shoulders and she is rarely seen without perfect makeup, impeccable clothes, and 4 inch heels. We started dating and I knew beyond a shadow of a doubt that she could be the one for me. But before things went too far I needed to confess my penchant for putting on a dress. I was nervous, but she had exhibited an open mind to erotic deviations - confessing her occasional fondness for other women and a love of light bondage. So I figured if anyone would be accepting of a cross-dressing guy she would be. Much to my amazement and joy she was completely cool with the concept.
We'd been dating for about a month when I owned up to my alternative wardrobe activities. After I confessed to her she smiled slyly and asked if I had any pictures. When I showed her the rather large collection of images of myself in drag she was speechless. She said I looked amazing. She had expected to see "a guy in a dress" and not some tall blonde hottie - adding that she was definitely jealous of my legs. I was flattered and stunned at her level of acceptance. I guess her being "bi" helped. She quickly urged me to dress again for her sometime. I didn't wait long. A couple of weeks later I got all dolled up and we went out - both in short skirts and heels. After leaving the bar we had a great time back at my place.
That was about a year ago. Rita and I continued to date and rapidly became a "couple". But the demands of everyday life seemed to leave us little time to explore any erotic adventures. We managed to hit a "swing" club a couple times and I even let her pick up another guy at a bar and bring him home so she could have a mind blowing session of double penetration. But the opportunity for me to dress and play just didn't seem to surface.
Finally, as fall approached we decided that I should don a dress again for Halloween - perhaps in some theme costume we could both enjoy. After looking online for about a week we settled on a fun little combo of the cop/prisoner combo.
Finding an outfit for her was easy - a spandex prisoner costume dress in bright orange with appropriate numbers stenciled on the front. It was short, coming to just below her crotch, made form fitting spandex to show her curves, and low cut to allow ample cleavage. She accessorized the outfit with a wide leather corset belt, thigh high leather boots with four inch heels, black fishnet thigh highs, and a black lace push up bra which was clearly visible.
My outfit was a bit more difficult to find. I looked online at many different "law enforcement" style outfits but none of them looked like they would flatter my form. They just didn't screamed "buy me!" Finally I found an outfit that would work. It was a khaki colored "sheriff" mini dress with short sleeves and a short pleated bottom which rode a good seven inches above the knee. I accessorized the dress with a wide black leather belt with silver buckles, black knee high boots with three and a half inch heels, requisite badge and patches, and of course a sturdy pair of handcuffs. For under the dress I chose a black lace bra, black lace cami top, matching corset with six garters, tan stockings, black satin thong, and a black lacy petticoat to fill out the pleated bottom of the dress.
Halloween quickly came and we rented a suite that was near the bar we were planning on visiting. It was a nice set of rooms consisting of a small kitchen area, living area with couch, chairs, and a fireplace. It had a large bathroom and a spacious separate bedroom with two queen beds. We quickly got settled in, stocked the kitchen with some drinks and snacks, and started to get ready.
Rita's preparations were done in a short amount of time. She has a natural beauty so a bit of makeup, fluffing the hair, and donning her outfit was done with relative speed. That left her time to help me with my preparations.
My transformation from "average joe" to hot tranny is a bit time consuming and it takes a full two hours to shave everything (and I mean everything), apply makeup, don the blonde wig, and get dressed. Rita helped lace me into my black corset, assisted with my chest tape to make convincing cleavage, and with snapping the garters onto stockings at the back of my thighs. Next, I pulled the satin thong on and tucked my cock back between my legs before pulling the thong all the way on.
For me the dressing process has a strong sensual aspect. The smell of the makeup, sound and feel of the lacy clothing, and most of all the sensation of sliding silky stockings up my freshly shaven legs is an incredible turn on. I can't really say why - just that it is an amazing feeling that I never tire of.
The rest of the outfit went on quickly - bra with breast forms, camisole, petticoat, and dress all slid into place with ease. The final step was pressing on the press on nails with a French manicure look.
Once I was fully dressed I pulled on my high heeled boots, tossed a few things into my small shoulder purse, and we were ready to go. But before we headed out, I naturally wanted a few pictures. I, like many of the cross-dressing clan, are true camera whores. I love posing for pictures while dressed so Rita snapped a dozen shots of me on the bed and standing in front of the door. Then I popped the camera into my purse and we headed out the door.
It was a short drive to the bar. The parking lot was full but we managed to find a place to park near the back. As we exited the car and started to head inside I snuck a furtive glance toward the dimly lit back of the parking lot, remembering fondly and with some chagrin how not that long ago in this same parking lot I had let a perfect stranger bend me over the hood of his truck, push my skirt up around my waist, and pound his meat up my ass. I'd never told Rita about that little adventure and had decided to keep that gem of a memory just for me. Focusing once again, I straighten my dress and we headed inside the bar.
As expected the bar was packed with a variety of folks in all kinds of costumes. There were plenty of transgender folks and a good mix of gay and straight - and the costumes were a smorgasbord for the visual senses. Everything from complex lighted costumes to funny outfits to slutty attire - it was amazingly fun to look at.
Rita and I blended in and quickly made our way to the bar. We were lucky and found two unoccupied seats at bar and ordered drinks. The music was loud, but not so loud you couldn't talk. As we chatted we marveled at the range of costumes. And while we talked I scanned the room for potential playmates for the evening. There were several attractive cross dressers in attendance and I had a hankering to play with another like myself. As I ogled the crowd Rita downed her drink, grabbed my hand and dragged me out to the dance floor.
Dancing in drag is always fun. The feel of the clothing while getting lost in the pounding rhythm of the music adds to the feeling of femininity. While we danced I could glimpse myself in the mirrors surrounding the dance floor. When I looked at myself I could see a tall, fit, sexy blonde dancing with a hot little Latina. It was intoxicating. And there's just something about wearing four inch heels that makes it easy to shake your ass! Rita was getting her share of attention - she looked incredibly hot in her form fitting outfit and several times a random guy would try to cut in on us or sneak a grope of her ass. But she's well versed in fending off unwanted attention and deftly maneuvered away from the superfluous suitors. We danced a few numbers and after some minor protests I finally convinced Rita that I needed another drink. She smiled and nodded and I led her off the floor and out onto the bar's outside patio to get some cool air and another cocktail.
The bar at the outside patio was less busy than inside and we quickly found a spot at a nearby table. Rita went up to the bar to order drinks and while she was gone I noticed a rather tall guy dressed like a baseball player sitting at the next table checking me out. When he realized that I had caught him looking at me he quickly looked away, but when he glanced back again I gave him a sly flirty smile and was rewarded with a smile in return. Just then Rita returned bearing a couple drinks. As we chatted I continued to catch Mr. Baseball looking over at me from his position behind Rita. I noticed that he was with a petite Asian woman. She was pretty with a round figure but not fat. She had black straight hair down to her shoulders and was dressed in a French maid outfit with fishnets and black patent spike heels. As Rita and I chatted about random topics I furtively watched my baseball playing fan and he continued to sneak glances my way. I wasn't sure where this was going but I was rather intrigued at the possibilities. I decided to take things into hand, got up from the table and told Rita to follow me.
We walked up to Mr. Baseball and his hot little French Maid friend and all I could manage to come up with was an incredibly lame, "Have I seen you two here before?" He looked rather taken aback but quickly recovered and said it was their first time at that bar. Rita quickly jumped in complimenting the woman on her outfit and we all started exchanging compliments all around. We introduced ourselves and they quickly followed suit - his name was Ken and his wife was named Amy. They were both professionals, had lived in the area for several years, and had been married for about five years. Within minutes the four of us were chatting like old friends.
As the night progressed we learned more about each other. Amy, like Rita, was bi (and they definitely seemed to be hitting it off). Ken confessed he had some bi experiences in the past and was open to almost anything. After chatting for awhile we all got up and headed for the dance floor.
We started out in typical couple fashion with me dancing with Rita and Ken dancing with Amy. Before long Rita and Amy started dancing with each other and as the drinks flowed the two of them began to get closer and closer to each other on the dance floor, running their hands over each other and grinding into one another. Needless to say it was an unbelievably hot show that they were putting on. As they danced Ken moved out of the way, stood awkwardly for a moment, and then he started dancing with me. He had a goofy look - sort of embarrassed - when he started to dance with me. At one point I leaned in close and asked him if he liked how I looked. "You look very hot!" he replied in a breathy whisper.
The girls continued to dance together, lost in their own sexual tension and oblivious to the rest of the world for the moment. Ken and I continued to dance together exchanging looks and occasionally brushing up against each other. At one point I leaned in close, put my face in towards his neck, and slowly breathed warm air along his throat. As I did this I felt him tense slightly and noticed what was obviously a growing erection move against my thigh. As we continued to dance he moved in closer and I felt him press more of his crotch against me. Slowly turning, I wrapped his arms around me and pressed my bottom against his crotch and let him slowly grind his hard cock against my ass. Feeling a flush of sexual excitement I turned back to him and suggested we move to the bar for another drink.
As we sat next to each other we watched our women continue to dance and grind with each other. I looked over at him and with a smile I said, "Looks like the girls have their evening planned...so what do you think we should do?"
He gave me a quick smile and I felt his hand move on my thigh under the bar. His hand slid up my stocking covered leg and under my dress as he replied, "I think we'll find something to do." I smiled back and suggested we head back to our hotel.
We finished our drinks and headed out to the dance floor to get the girls. We got no argument from them. We left the bar and Rita and I piled into our car and Ken and Amy followed in theirs.
Once we got back to the suite I quickly lit a few candles that we had brought and placed around the room. Rita offered up some drinks. I wasn't sure where all this was going next - but there was no need for me to worry. Rita, not being one to waste time, grabbed Amy by the hand and led her into the bedroom. They stopped at the edge of the bed and started kissing each other with surprising zeal. They held each other, hands roaming over each other's bodies with an intensity born of their building passion. Rita, being a bit dominant, pushed Amy onto the bed. Amy kicked off her heels and Rita pulled off her own thigh high leather boots and climbed onto the bed with Amy where the two of them started to kiss and fondle each other.
Ken and I were stunned into silence and inaction. I knew Rita was bi but had never seen her with another woman before. I glanced at Ken and he just grinned, watching the show the two women were putting on for us. I looked back toward the bed and Rita had pushed Amy's skirt up, pulled her thong to the side, and was beginning to slurp noisily at her neatly trimmed pussy. Amy moaned loudly and arched her back. I immediately felt my cock start to strain at the front of my own panties. The sights and sounds were surreal. Two incredibly beautiful woman were going down on each other like there was no tomorrow. My first thought was to climb up behind Rita, push her dress up and plunge my cock into her. I trembled in my high heeled boots slightly at the thought. But before I could react Ken placed a hand on my shoulder and turned me to face him. He bent toward me, circled his arms around my waist, and started to kiss me.
Again, I don't consider myself to be gay or even bi, but there is something that happens when I wear a dress. So after a fleeting moment of resistance I opened my mouth and let him kiss me fully. As he held me I could feel his hand play across my back and down to my ass. One hand slipped deftly under my skirt and started to massage my ass and tugged on my garter strap.
We broke the kiss and I looked over to see if Rita had noticed. She was oblivious - gone now in her own world of pleasure as she and Amy continued to lick and suck and finger each other. Their clothing was slowly being peeled away and now they were both clad only in bras and stockings. The site was entrancing and erotic, and as much as I wanted to stay and watch I had some needs of my own that demanded filling. I took Ken by the hand and led him into the living area of the suite.
My new friend didn't waste any time. He quickly stripped off his shirt, shoes, and pants and stood before me in nothing but his boxers. His cock - which measured something around six inches - stuck out noticeably from the front. I moved toward him intent on dropping to my knees to suck him off but he seemed to have other ideas. Before I could move he stepped toward me, dropped to his knees, and pushed my dress and petticoats up. With a quick motion he jerked my thong to the side and released my stiff prick from its satin prison. Then he leaned in and took me fully into his mouth.
I leaned back against a chair as his warm mouth engulfed me. It felt so good I almost shot a load right there. I gasped as his tongue circled the head and he slid down along the shaft until I could feel his tonsils pushing against my swollen head. I lifted my dress up a bit more so I could watch him sucking my cock. His warm mouth and quick tongue movements felt unbelievable and as he slowly slurped and sucked he moved his hands up and down my stocking covered legs, occasionally stopping on my ass under my skirt. As he sucked he slowly started fingering my ass and then used his other hand to stroke and fondle my smooth shaved balls.
I looked down to watch and visually take in the moment. I saw his head bobbing slowly on my stiff cock, his face disappearing under my bunched up dress, the tops of my garters holding up my stockings, my legs spread wide with high heeled boots planted on either side of his kneeling figure. I was almost overwhelmed with the sexual environment - the soft candle light, the feel of his hands roaming on my stocking covered legs and exploring my ass, the sounds of the girls in the next room moaning in their own self contained world of pleasure. All of this combined to bring me to a quick and amazingly powerful climax. I gripped the chair and cried out as I shot my load into his greedy mouth. He slurped it all - not spilling a drop. The intensity of my orgasm left me weak and slightly dizzy and I almost slumped to the floor. Before my head cleared from the intensity of the orgasm Ken stood up and wrapped his arms about me and drew me in for a kiss. Our tongues met again and I could taste my own seed. The texture of his lips and tongue mingled with my cum was an incredible turn on and my softening cock twitched again in growing excitement.
The sounds from the next room were growing in volume and intensity and I moved on wobbly legs to take a peek into the bedroom. The girls were lying side by side in a slow sensual sixty nine, each licking the other with languid movements. The air was thick with the smell of their sex and they moaned and cooed softly as they continued to pleasure each other. Again I was filled with an urge to climb up onto the bed and join in. But once again Ken, who had joined me in the doorway to watch, had other ideas.
He gently placed a hand on my shoulder and turned me to face him. We kissed again and he fumbled to unbutton my khaki costume dress. I helped him along with his quest by undoing the belt and shrugging out of the outfit. He stepped back and looked me up and down again as I stood before him in my bra, camisole, petticoat, garter, stockings and boots. He moved forward again and wrapped his arms around me for another kiss. As our mouths met and tongues intertwined I felt him exploring my body. His hands moved down to my waist and then up and under my petticoat. He then proceeded to tug on my thong - pulling it down toward my knees with a swift strong tug. I got the hint, stepping away briefly to slide the panties down to the floor where I stepped quickly out of them and moved toward small table in the suite where various bottles were sitting including a rather conspicuous container of lube.
Ken came up behind me, lifted my petticoat slip, and pressed himself against my back. I could feel his throbbing meat against the crack of my ass. He took me by the shoulder again, turned me around, and pushed me back until I was sitting on the table edge. He then lifted my legs until I had to lean back and balance myself with my hands on the top of the table. He gently grasped each leg and unzipped and removed my high heeled boots in turn. Then I watched as he poured lube onto his fingers and stiff cock. He lifted my legs higher and placed my ankles onto his shoulders and I had to surrender my position and lay down on top of the table. He then started working his fingers into my ass. First one and then two of his digits moved quickly and smoothly into my tight hole and I trembled at the intense sensation. After a few moments of this he moved forward slightly and positioned his cock to enter me.
Now in the past I had always required my male paramours to sheath themselves in protection. But the heat of the moment (probably combined with the copious amount of alcohol I had consumed) pushed the thought from my mind. All I wanted at that moment was to feel his stiff cock deep inside me. He was more than willing to oblige.
He entered me slowly, my legs raised high, ankles on his shoulders, and his hands on my hips and he pulled me toward him. I gripped the edge of the table hard as he started to slide in and out of my tight ass. There was a bit of pain this time but it quickly passed leaving a feeling of fullness and excitement. I looked up to see him standing before me. His face, framed by my stocking covered feet resting on his shoulders, intense in concentration and excitement. His strokes were slow and steady - pulling almost all of the way out before plunging back inside me. It felt incredible.
After a few minutes he paused and reached over for the lube bottle again. Then, after pouring another copious amount into his palm, he started stroking my reawakened cock with his right hand while he continued to slide his meat into me. A few seconds after he started this the sounds from the next room picked up in intensity as Rita, who I recognized by her voice, had what must have been an earth shattering orgasm as she cried out in sheer erotic delight. This, combined with Ken's manual manipulation and anal plundering, pushed me over the edge again into an intense wave of orgasmic bliss. I gripped the table and shouted as I shot my load for the second time that night - a jet of hot sticky cum shooting into the air and landing on my petticoats and stocking tops.
Ken, much to my surprise and enjoyment, was still going strong. He slid his cock out of me and pulled me up into a sitting position. He then led me over to the center of the room and told me to get down on my hands and knees. Being a people pleaser at heart I quickly acquiesced to request and assumed the doggie position.
Ken knelt behind me and soon had his cock buried in my ass again. He kept up his slow and steady pace, sliding in and out with a regular rhythm. His hands grasped my hips and he fucked me long and hard, occasionally shifting position to grab the garter straps that ran down my ass and tug when he pulled me toward him. After a few minutes of this he picked up his pace and I could sense that he was getting ready to cum. He moved faster, sliding deep into my ass. Then with a cry he pulled me hard toward him, burying his cock deep in my ass and holding me there as he came. I felt warmth deep inside me as he shot his load. His hands held my hips tightly and he continued to hold my against him as his orgasm passed. Sweating exhausted, and happy, we both collapsed into a heap on the floor.
When I finally started to emerge from my post sex glow I slowly untangled myself from Ken and got up from the floor. The room was quiet and I peeked in through the bedroom door to see both Rita and Amy passed out on the bed, still tangled in each other's arms and sleeping with the peace that only comes after intense sexual pleasure. As I stood there admiring their beauty I noticed an unfamiliar sensation as Ken's seed leaked out of my ass and ran down the back of my thigh. I smiled at the feeling and looked back into the living area of the suite where Ken was rousing himself from the floor. He saw me and smiled back as he moved into the kitchen area to get a drink.
I plopped down on the couch, my clothing disheveled, a run in my stocking, and my makeup a mess. Ken joined me on the couch a few moments later he offered me a beer from the fridge. We both sat and chatted a bit like two old friends, talking about how hot it was to watch the girls and how we would all have to get together again soon. I asked him how long he'd been into t-girls and he told me a few years. I asked if he dressed and he told me no. He asked how long I'd been dressing and I told him about how I'd started seriously doing it a few years before - but didn't get to do it as often as I would like. As we sat there drinking our beers and chatting I noticed breaks in the conversation and that Ken's eyes were starting to droop. It wasn't long until he started to drift off to sleep. Figuring we were done for the night I got quietly up from the couch, crawled onto the second bed in the bedroom, and soon fell into an exhausted but happy sleep.
When I awoke in the morning Ken and Amy were gone, having slipped out sometime during the night. As I stretched and yawned, sore from wearing a corset all night, I looked over at Rita who was starting to wake up herself. As we talked a bit I asked her how she had enjoyed the evening. With a sheepish grin she said he had a good time. She admitted that much of the evening from the time we left the bar was a bit of a blur, but she remembered some intense orgasms due to the talent of Amy's tongue. Then, with a puzzled look, she asked me what Ken and I had done while she and Amy had played. I paused for a moment, glancing out the door of the bedroom into the living area of the suite where I could see my satin panties crumpled up on the floor where I had left them. Then, I simply smiled and answered "Not much. We just watched."