Putting on a Show, Part 1 By Stevie 4280
This story and its companion "Putting on a Show, Part 2" are based on events over a weekend of my life in the late 1980s. The names have been changed. No insult is intended to anyone who may find similarities between themselves and the people and events described.
I had met the couple through a personal ad in an alternative newspaper. They were in their 40s and attractive and sought a bisexual cross dresser for evenings out. I had met the husband alone and we had enjoyed one another's company. I doubted that I was his first male partner. His wife joined us on our second meeting and I stood in a corset and stockings while he sucked me and his wife watched. Now it was a month later and I was back in town in a motel room dressing for another evening with the couple and on this evening he called to say his wife wanted to watch me.
I was in my 20s then and although I was smooth shaven, dressed regularly, generally passable and had recently spent a five days traveling comfortably in drag I wasn't an experienced gay lover. I had been with only two other men. I had learned all of what I knew in sex with my steady lover, Kenny, and a few porn videos. Most important, I had never been watched. Cross-dressing is of course all about display and I loved being eyed in bars and didn't even mind being read in public. I was still discrete. I flirted, but refrained from displays of sexuality. I liked the feel of a hand on my thigh under a bar table, but only if unnoticed. I kissed in public, but only in polite kisses with Kenny. Frankly, I felt that I had enough on the line as a young man dressed as a woman and I wasn't confident I could risk any more by putting myself on display.
But I had watched women performing oral sex on men. Occasionally it was even a woman I was dating giving the service when we swapped with other couples. A blowjob was intensely sexual for me and so was the watching of one and the thought of performing for others was intoxicating and terrifying. I was fearful of abuse. I was fearful of being incompetent and embarrassing myself. What I feared most was being helpless.
That changed that February night when I discovered that oral sex is powerful. The image of someone on their knees doesn't suggest that, but as a guy melts into passion between your lips people's impressions can move with tectonic results. Debbie, the wife of the couple I was meeting, had watched her husband, Frank, suck me a few weeks before with little response. She sat on the couch the entire time and they left immediately afterward. But that evening with the roles reversed, she was in rapture. At points in the evening she knelt with me over her husband on the bed and passed his cock from her lips to mine. When I first took it into my throat you would have thought it was her cock in my mouth from her response. The sight of his cum on my lips brought both of her hands to her chin in surprise. And then it was my turn to be surprised when she kissed me. She had her husband put me on my back at one point while she pulled my cock out of my panties, sucked me hard and straddled me. But she hopped off when she feared I might cum.
After that her husband asked me to kiss her breasts. It was a roller coaster of sensations. Her body was damp from the exertion of a few minutes before and tasted of salt and perfume and maybe bath oil too. She guided my mouth over her body and then pushed me to her crotch asking me to suck her like I had her husband. "Let him watch," I recall her saying. And so I did.
I had given women oral sex many times and enjoyed it so I began enjoying myself again. I slid my tongue through her labia, keeping my face as far as possible from her body to give Frank a view and also preserve my makeup. She cooed as I pinched her clitoris against my upper lip with my tongue and slowly the similarities with a blowjob dawned on me. What I was doing with my lips and tongue was like working my tongue on the cock head. Pressing my tongue up on the clitoris was like working my tongue on the loose flesh below the cock head. It was something I'd learned from my lover Kenny. It was a sure way to speed him to ejaculation. I sucked her enlarged clitoris into my mouth and pulled back, just like on a cock. With her clitoris taunt between my lips I would flick my tongue flapjack, then lap after lap around the knob and she bucked beneath me, not unlike a man thrusting. She yelped when she came.
The three of us were on the bed and her husband had been stroking himself throughout. She asked him to get on his back and she quickly mounted him and began grinding herself into his hips and brought her orgasm back to a boil in minutes. Frank soon came as well. Finished, we lounged on the bed smoking, after which they dressed and left.
It was a thrilling evening, but not satisfying. Within minutes of their departure I was in front of the mirror redoing my makeup and hair and preparing to make my first solo trip to a gay club. I had been in a gay club in drag twice that winter in Seattle; once with my partner Kenny and a second time with an acquaintance. This time I was in Portland headed to a club called The Embers that I had visited in street clothes when I was in Portland the month before. There was a bar and dance floor in back and a second bar and drag review on a separate stage at the front of the business. I had never visited a club in drag alone before. Like earlier in the evening, I was thrilled and terrified at the prospect of doing something so foreign. From my previous visit, I knew there would be beautiful transvestites there, both on stage and in the audience. I wasn't dumpy, but I doubted I wasn't in the same league with them. There were lots of attractive dressers there with poise and chutzpa. I had little of either. Despite that, I hoped I would be propositioned, which had already happened to me once in a gentlemanly way in Seattle. I doubted it would be so gentlemanly tonight. And given my behavior already that evening, I new I may not be so ladylike myself. As I stood in the mirror I admitted to myself that my real intention of going was to be picked up. It excited me to realize that and it made me nervous. I welcomed and feared it both.
I was wearing a black shoulder length wig, black satin corset, bikini panties and stockings. Over it I wore a purple suede miniskirt and crushed velvet pull over in pewter with three-quarter length sleeves. It had a hint of Lycra in it that made the velvet hug my body and fit nicely into the waistband of the skirt. It had a wide boat-neck collar that drew attention away from my shoulders to my neck and face that were made up in muted plum tones. I grabbed a long coat and a purse and left.
Each room of the hotel opened to the outside and it was refreshing to step out into the cold. A man and woman were climbing the stairs toward me on the second floor and I confidently walked past them and down the stairs. The drive was uneventful and I parked in a lot across the street from the bar. It's only when I saw the line into the door that I realized there was a cover charge. When I had visited the prior month, it had been earlier in the evening. It was now 10 p.m. and they were charging admission. I couldn't slip in unnoticed. But I was determined and waited until the line dwindled to about 10 people and made a beeline from the lot to the door. The couple in line ahead of me didn't even turn to look at me. The door clerk and a bouncer lounging nearby couldn't have cared less.
The bar with the show stage was packed. There was some space around video game terminals and the few tables at the back of the room, but the rest was filed with an array of people in glamour, gothic, biker and ordinary attire. The room contained twice as many people as I had seen on my earlier visit and there were at least two groups of lesbians. On stage a TV lip-synched "What's Love Got to Do With It" by Tina Tuner. She was a white TG, so comparisons to Tina were vague, but she had the skin-tight dress, stockings and strut down to a "T" and the crowd loved it. After a couple verses sung amid the tables, her bosom overflowed with dollar bills tucked into her bra by admirers. I took in the whole act standing at the back being jostled by passersby headed to and from the dance floor. After she finished I worked my way to the bar and ordered a drink, then spotted an empty stool about half way down the bar and made my way to it, took off my coat, folded it and placed it on the stool and sat down. I lit a cigarette, tipped the bartender heavily and tried to strike up a conversation with him but he was way too busy.
I was alternately rattled and comforted by the commotion. The acts were great. The emcee was a gorgeous TG in a cream colored sequined gown with a neckline that plunged nearly to her navel and a hemline that was slit nearly to her crotch. Add to that 4-inch heels and surprisingly thin legs for a TG and she was intoxicating to watch. I dreaded what would happen when a heavy set cross dresser took the stage, but ended up laughing nearly to tears when she produced a teddy bear with a strap-on dildo and squatted over it on stage while singing a rock version of some nursery rhyme about bears. The audience began throwing condoms. I was entertained, but alone. It was so loud talking even with those on the next stool was almost impossible. The guy on my left was with one of the performers, who he introduced me too. She was performing LuLu that evening, complete with a blond shag wig and skin-tight turtleneck knit dress in black. The guy on the other side was with a woman, who told me I looked nice and asked what lipstick I was wearing. I drank too much.
So I was more than a little surprised when during an act I felt a hand on my arm and turned to find myself eye-to-eye with a man about my age. His name was Don and he wanted to buy me a drink. He wore a flannel shirt unbuttoned over a white T-shirt and jeans. He was clean shaven and about my age and I said yes. I shouted my introduction into his ear and the conversation went that way until our drinks came and he led me to a table in back and we learned we were both college students and both there for the first time, or so we said. He told me I looked nice. As we finished our second drink he asked me to his apartment.
I knew I would say yes, but fascination and fear swept over me. His invitation came suddenly, or so it seemed. By then we had moved our chairs closer and his arm had slid around my waist on a couple of occasions as he leaned in to hear me during an especially loud song. His fingers had explored the pattern of corset laces beneath my blouse. His knee had grazed my nylon-covered legs many times and gently pried them apart once. I had let him do that. I said I would go to his apartment if he would bring me back to my car later and he said yes. We kissed in the car and he fondled me until I became hard in my panties. He asked me if I had condoms and I told him that I did.
His apartment turned out to be a second floor walkup on the edge of an industrial area near downtown. On the way up we paused on a landing for kisses. Once inside, he poured more drinks and I excused myself to the bathroom. When I returned he was already on the couch and he raised his glass as I walked into the room. I took my glass and sipped as he did. We kissed the moment I sat down.
There's something comforting in knowing exactly what you want and in that sense Don and I were a comfortable couple. He had kept his hands on the wheel on the drive over, but no longer. He had my skirt up over my stocking tops during the first long kiss. His hand was warm on my thigh and nimbly flicked into my panties and took my cock. Somewhere among the alcohol and my own racing pulse I remember he had said earlier that evening that it was his first visit to The Embers. It was a lie. He knew exactly what he was doing with a cross dresser. He stroked me hard and gently pushed me onto my back as his lips fell around my cock. After the selfish couple earlier that evening, I was eager for the attention. He had me in his throat quickly and I ran my fingers through his hair as he moved his lips over my cock. Then he pulled back and lifted me up on the couch for a kiss and told me it was my turn.
I knew of course what he meant. My hand was traveling up his jeans to his crotch even before our lips met. The bulge was noteworthy and like he had done to me I kissed him as I undid his clothing and gently pushed him onto his back. His cock was a slender 7 inches and like his chin, clean shaven. It was my first experience with a shaven man and it felt wonderfully sexy. The evening, the alcohol and the vaguely illicit way we had met combined to make the silky phallus gliding through my lips that much more erotic. This was a bad boy and he made me want to be a bad girl. After several passes I lifted my lips off his cock and looked at him as I dribbled saliva between my lips onto his cock. I dropped my mouth over the cock and gathered up all the liquid and repeated the process again. Then again. He smiled and asked me if I liked sucking cock and I said I did.
I pulled back and took off his shoes and socks and tugged his pants down from the cuff. The short tugs aggravated Don, who wanted his pants off in a rush, but I told him to be patient. He swore at me and smiled. I lifted my blouse over my head and tossed it onto the couch. With the first view of my corset he sat up and pulled me into his arms for a kiss. He undid the button and zipper of my skirt and slid it over my hips. His hands felt the corset laces and my taunt waist. He asked if I wore corsets often. I told him every chance I get, "because it makes me feel sexy." He told me it was sexy and leaned back again on the couch and I crawled out of my skirt and closer between his legs and held his eyes with mine as I took his phallus back in my mouth.
Again I slathered his cock with saliva and let it flow back between my lips over him. I lifted the cock and licked the scrotum. It was shaven and entirely hairless. The texture was smooth between my lips. I took each ball in my mouth circling it with my tongue slowly, then faster, then slower. I'm not sure how long it went on before I distinctly heard a squeak and jerked my head up to see another man leaning on a chair just inside the doorway to the living room. Don rolled his head to the side and I recall him saying clearly: "Hey Rob, this is Stevie."
I'll admit I was naïve about the gay scene and what it meant being a cross dresser at a gay bar. Sitting on a bar stool in a miniskirt made it apparent I was out for adventure but that didn't mean I was public property, or at least I didn't think it did. It appeared Don and his friend thought otherwise. Rob was taller than Don, a little scruffier and his hair was longer. He sat down casually in the upholstered chair he had been leaning on and complimented me on my appearance like we were familiar acquaintances. Then he slid his hand over his crotch and added: "I heard the part about you liking to suck cock and I just had to see what was going on."
Who could deny it? On my knees in a corset with Don's cock in my hand I knew you could also say a lot of other things about me that I would have a hard time denying. I was also more than a little angry. Everything about Rob's behavior indicated he didn't just want to see what was going on, he expected the same. After traveling across his crotch a couple of times his hand cupped his manhood and he looked me right in the eye.
"So do you guys take turns?" I asked with obvious anger. To my surprise, they admitted that yes they did. Sometimes they went to the bars together, but not that night. Don said Rob was working late and Don had no idea Rob would come home so early. But what if he had, I was giving such a wonderful blow job why not just go on with it and let Rob watch or not. It was up to me, said Don. "Tell him to leave if you want Stevie."
My head was swimming again. Don's tone was so casual and confident he was certain he would get what he wanted regardless. I was probably being lied to, maybe I was being tricked, but the outcome wasn't a bad one. I left the motel looking for a stud and now I had two. Earlier in the evening I made a show out of sucking a man's cock for his wife. Was there any difference? Rob's eyes were still locked on me and I turned back to Don and slowly lowered my lips to take in just the head of his cock and nursed it. I lowered by lips just past the head and then back to the tip and nursed it some more. Don smiled and laid his head back on the couch and let out a slow "jeeeeezzzzzzzz."
Like it had had earlier in the evening I wanted my show to have a powerful effect on my viewer and I was going to use it. "Just sit and watch Rob," I said with a glance toward Rob. Then I rolled my tongue around the head of Don's cock and gradually gathered a mouthful of saliva that I pulled back and let flow onto his phallus. It danced beneath my lips as the warm liquid flowed from my lips. I decided to take my time lowering my mouth slowly and tonguing the bottom as I took the entire length into my mouth. Then, slowly, I moved my lips up and down his shaft. I pressed my tongue against the underside of his cock as I moved my head slowly up and down. I drew the nails of both hands lightly across his balls. Don was now quietly talking to me about how good it felt and that my mouth was so soft and deep. His commentary was the perfect compliment to my movements, or so it seemed, because the few glimpses I got of Rob were of a man in heat.
Keeping up the attention to his balls, I moved my lips out so only his glans was between my lips and I began to twirl my tongue around it. First quickly, then slower, adding suction now and then to great effect. Don was squirming and put his hands to my head and I quickly pulled back and pushed them gently aside. I lowered my lips to his testicles again and took one then the other into my mouth performing the same routine I had on his glans, twirling and sucking, fast then slow.
"Damn girl," I heard and looked across the room to Rob who had his cock out of his pants by then. It was then that I decided to do my best to drive him mad. I took Don's cock back into my mouth and began to gently massage his balls with my right hand as I slowly moved my lips up and own his cock. I would stop for a second at the bottom and swallow, massaging his glans with my throat muscles. Then I would pull out to the tip and twirl my tongue and suck. With each pass his cock head went to the back of my mouth and into the top of my throat and the effect was making Don squirm beneath me.
I took a fingerful of saliva from my lips and slid it under Don's balls and began slowly massaging his prostate. I was now moving my head slightly faster. Don's frustration was building I could tell because he tried to buck into my lips, but I moved with him to diminish its effect. His hands moved to my head but I brushed them aside and pulled off him briefly. "Let me," I whispered. Across the room Rob called out. "Oh jezzz baby let him have it."
Who I intended to let have it was Rob, the sneak, so I kept my pace deliberately slow. My mouth moved down, paused, moved up, paused. Down, up, down, up. Then Don tensed beneath me and I knew he was getting closer and slowly I slid my finger further onto his prostate and then to the edge of his ass and then across his ass hole as my lips fell harder onto his cock. The effect was electric and immediate. Don was moaning loudly and non-stop now as my finger moved quickly back and forth. I felt his cock jerk in my mouth and the splash of cum hit my throat. I pulled my lips back to the edge of the glans and moaned myself as the cum flowed across my tongue.
Don sighed heavily and I let him move his hands to my head. He gently wove his fingers through my hair as I used both of my hands to milk the last drops of his cum onto my tongue in plain view for Rob. From the commotion across the room I knew my performance was having the desired effect. I leaned back on my heels and ran my nails down Don's legs as I did so. He smiled and we ignored the squeaking in the chair across the room. Rob was obviously jacking off, but who wanted to see that. I smiled back at Don and without looking away from Don's eyes I said: "You can come over now Rob."
He was there in a flash standing to my left his cock rock hard and purple from the chaffing he had given it. He smelled of printing ink or some such odor but his hands were clean and his rock hard six inches were frankly appealing. I could tell it wouldn't take long. He reached for my shoulder and I slapped his hand away and Don laughed.
"You don't get it yet Rob. She's the one doing us," Don said laughing. I held Don's eyes with mine now and slowly took the new cock between my lips. It throbbed at my tender pressure and I decided to make this show for Don. I twisted my body slightly so I could watch Don as I took Rob's cock deeper and slowly began repeating the show. Unfortunately for Don, it was a short show. In a few strokes Rob quaked and his cum flowed into my mouth.
It was about 1 a.m. by the time Don took me back to my car parked downtown. He said he and some other friends were having a Super Bowl party that afternoon, would I like to join them. I asked Don if they would be friends like Rob and without hesitation Don said. "Yes." Even after the drinking, the long night and the adventuresome sex I was thinking clearly enough to understand immediately that I was being lined up again. Though he had never said so, Don thought that a cross dresser in a miniskirt on a barstool was a whore and I had not disappointed him. I had not disappointed myself either. "Sure," I replied. I asked him to pick me up at my motel and we kissed as he let me out at my car.