A Bet Is A Bet free porn video

A BET IS A BET by Throne Darren and I had been pals since grade school. We had even remained buddies after he revealed his penchant for crossdressing. I wasn't thrilled about it, but he didn't dress that way when we were together, so it was acceptable. I had a good job in accounts analyzing. He had gotten into the costume department of a major movie studio. I'll admit that, because I'm such a movie buff, I was jealous of his opportunities to meet major stars. He never made a big deal about it, though he did drop names once in a while. I tried to stay cool whenever he mentioned one of my favorites but a while back, when he said he would be dealing with Tim Cross, I couldn't hide my excitement. Tim is my absolute favorite star and I acted like a fan fanatic, asking questions and dropping hints about being invited to the set. Darren laughed good naturedly at my attitude, and gave me the disappointing news that the set would be absolutely closed. But he said he might be able to get some kind of small souvenir. Because I was between girlfriends I had plenty of time to think about that. I was on tenterhooks for the next several weeks. Then I began to lose hope. When I had finally made up my mind that nothing was going to come of this unparalleled opportunity, my friend dropped a bomb on me. He showed up at my apartment with a dry cleaning bag that obviously had something in it. "I got a personal gift from Tim on the set today and thought you'd like to see it." Darren sat down with the bag across his lap, in no hurry to show me its contents. He smiled and said, "This is where the host is supposed to offer his guest a drink. "What?" I took a second to compose myself. "Sorry, Darren. Would you like a glass of wine? White?" "Do you have any pink?" "No, I'm sorry. But..." Again I had to rein in my eagerness to see what he had brought. In a calmer voice I asked, "Will white be okay?" "Sure," he said. "No problem." He ran his hand slowly, almost caressingly, over the hidden item. I hurried to open the bottle and pour him a glass. Before I took it to him I realized it would look better if I also got one for myself. So I filled a second stemmed glass and was careful to move slowly as I returned and gave him his. Then I sat down and crossed my legs, the picture of relaxation. I even managed to compliment him on the pullover sweater he was wearing and ask if it was new. "Barry," he said with a roll of his eyes. "You've seen me in this old thing plenty of times. I'll have to teach you to be more aware of what people are wearing." Giving him an easygoing shrug, I said, "Sure. Sorry. I'm just a typical guy who doesn't notice those things." "Oh, you're not that typical. Certainly not some uncouth jock. There's nothing wrong with you that a bit of instruction couldn't fix." He paused to take a sip of his wine. "But I don't think that's what you want to gab about right now." "It isn't," I admitted. My eyes went to the white plastic bag. "And you know that." "All right," he said merrily, lolling his head side to side, the way he did when his feminine persona occasionally showed itself. "You win, tough guy." I squirmed a little on my chair and took a swallow from my glass. He knew I was slightly uneasy any time he became less Darren and more of his feminine self, who he called Darling. We had talked about it several times over the years, and he always joked that he'd like to see me in drag. His opinion was that, with my smooth and regular features, and small frame, I would look great as a woman. Or a she-male. But he knew I had no interest in actually trying it. It was fine if he wanted to dress up and prance around, especially if he limited himself to doing it at the particular club that he favored. Raising my eyebrows expectantly, I waited for him to share what Tim Cross had given him. Darren took another delicate sip of wine and daintily replaced his glass on the end table. He really was slipping into his girly role. But then he held up the bag with one hand inside, got a grip on the top of the plastic, and swept it away with a flourish. I sat there gaping at what I was seeing. My mouth moved without producing words. "That's not possible," I finally said between deep breaths. "Oh, but it is," he insisted, standing and running his hand over the familiar piece of clothing, presenting it as if he was on some game show, displaying a prize. "You're telling me that Tim Cross gave you the jacket that he wore in Jets Fly High?" "Actually, there were about a half dozen of them, all alike. He took two home with him. This is one he wore in the cockpit scenes. Would you like to try it on?" Feeling numb, I got to my feet. "Of course I would." He held it out to me. "And it should be a perfect fit. After all, you're both short guys." I ignored that remark and accepted the proffered bomber jacket. Slipping my arms into the sleeves, I could smell the leather. As I got it on just right and zipped it halfway up, I was nearly in a trance. Darren handed me my wine and I drained it. He took back the glass and set it aside. Incredulous, I wanted to know, "Why would he just give you this?" "Well, I showed him a few tricks to make him look even more handsome on screen and he had to agree I was right. So the next day he showed up with this and said he wanted me to have it. Of course, I thought of you immediately. And that you'd appreciate it even more than I would." "You mean... you would give me this?" "No, but I'd make it possible for you to win it. We could make a simple bet and, if you come out on top, I give you the jacket. I told Tim about you, what a maniac fan you are, and he said it would be okay." Struck speechless for the moment, I gestured for him to wait, then hurried to the kitchen to refill my glass. Drinking half of it right there, I topped it off again. I brought back the bottle but then saw that his glass was still mostly full. Feeling a touch sheepish, I set the bottle aside and sat down. With a casual attitude I didn't say anything, trying to convey that I wasn't overly anxious. He responded with a similarly cool demeanor, though he did put one hand lightly on the side of his face, again showing his Darling side. Finally, unable to contain myself, I wanted to know, "So what's the bet?" "It's simple enough. If you can pass as a woman... or a very convincing TV... I give you the jacket. How does that sound?" Overcome by uneasiness, I blurted out, "But I can't go out somewhere all dressed up like you do. I'm not..." I caught myself just in time, and finished with, "... I'm not attracted to that lifestyle." "Oh," he said and gave a limp wristed wave of his hand, "don't knock it till you've tried it." I wanted that jacket badly enough to make myself act unflustered. "I don't see any way to accurately judge me anyway, so if you can think of a different bet..." "There's a very simple way to decide if you pass the test," he pointed out. "Just come to the club that I frequent, I'll have some of the girls give you a makeover, and then you can enter one of their funny little contests. The crowd decides if you're properly princess-like, and if they think you are -- snap -- I give you the jacket. But if you lose, then..." He thought for a few seconds. "... you can clean my apartment for a month." Taking one more fortifying swallow of wine, I squared my shoulders. As much as I desired owning that jacket, and with the amount of alcohol in my system, something clicked. I told him, "All right, you're on. And a bet is a bet. No backing out after I win." "No backing out," he agreed, and added, "for either of us." So everything was arranged. On Friday night I would go with him to a place called The Pink Peach, a couple of his peers would dress me and do my face, probably give me a foolish looking wig. I'd strut around in front of whoever was visiting the club that evening, there'd be some sort of voting, and if I passed, I won. My thinking was that the roomful of sissies would like seeing a new face, so with a little effort and a minimum of luck I'd win our bet and that would be it. I could jump back into my male clothes and be out of there. Very soon that coveted jacket would be mine. The weekend arrived all too soon. Darren showed up at my door, ready to take me to the club. I wasn't happy about what I was going to have to go through, but kept reminding myself that the reward would be worth it. Besides, no one there would know me. I got into my pal's car and off we went. Soon we were in the heart of the city. He drove down a narrow street and pulled into a private lot. There was a plain door with a single, shaded light above it. I followed him to the entrance, my stomach full of butterflies. He opened the door and ushered me in. At the end of a short corridor there was a second door. He knocked and it was opened by a tall Black woman in a sequined gown. Except that she was no woman. Her broad shoulders and strong jaw told me she was male. Even so, she didn't come across as at all masculine. Her body language and modulated contralto voice were entirely feminine. Though my friend was in male clothes, she addressed him as Darling and passed us on. Just beyond there was a side door and Darren opened it. I began to feel like I was getting deeper and deeper into a maze. He told me, "The dressing rooms are right through here. And you ARE going to be dressing, now, aren't you?" Shifting my feet nervously I conceded, "Yeah, I guess I am. This one time." "Of course, sweetie. Just once. Absolutely." As we entered, I wanted to tell him not to address me that way. But I held my tongue as he gestured to several figures who were seated in the low ceilinged space. They had their backs to us are were facing a mirrored section of wall with focused lighting. As we drew nearer I saw the reflections of their faces as they applied generous amounts of make- up. "Hello, ladies," Darren said, sounding more like a drag queen than I'd ever heard him. "Look what I've brought you." One of them turned partway around, sitting sideways on her chair, looking at us with eyes decorated with heavy liner and purple shadow. "How cute. Short. Petite. And with a sweet oval face. Where did you find her?" "This is my friend Barry. My STRAIGHT friend. We made a bet and he has to get all gussied up, go out into the club, and see if he can pass inspection. Could you be dears and get him ready for his coming out?" "Turn a good looking straight boy into a princess? Sounds like a dream come true." I was caught in Darren's world. The man speaking to us introduced himself as Lotta Lips. As he rose I saw that he wore only a corset and panties. There wasn't a single hair visible anywhere below his high arched eyebrows. He pursed his magenta-hued mouth and appraised me, so that I felt like I was being considered for purchase. "Yes, Darling," Lotta said. "I can work some magic on your girlfriend." The figure next to him swiveled his head around. He had some sort of cover holding his male hair down and his face was garishly made up. "Hello, honey," he said to me. "I'm Carmel Candy. And I'll be thrilled to lend a hand. Or two." He had on a what looked like a normal, short- sleeve blouse, except that it ended at mid-chest, along with ruffled panties, and both items were pink. Darren stepped in front of me and began unbuttoning my shirt. "That jacket is almost yours, Barry. But we can't keep calling you that. You need a femme name. How about something simple like... Berry? Now you let my sisters here do their thing while I get into my own glamourous goodies. Don't worry, I'll be right down at the end of the row. Just holler if there's any problems." He giggled foolishly as he finished opening my shirt and pulling it out of my pants. I watched as he sauntered off to vanish beyond a shower curtain that was hung on a horizontal pole as a room divider. Not being able to see him made me feel especially vulnerable. Lotta and Carmel got on either side of me and continued with my undressing. I wanted to stop them but everything was happening too quickly. In moments I was standing there in just my white jockey shorts. "How butch," Lotta said. "But we have to do something about that obvious basket," Carmel commented, almost but not quite touching my privates. "Of course," Lotta agreed. "After we get rid of that unladylike body hair. Not that there's much of it. And it's blond and kind of hard to see. But the girls out in the club can be so picky. And we don't want our sweet Berry to lose that bet by being too macho. So..." He clapped his hands several times. "Out of the shorts and into the shower with her." Her? Was she... I mean he... referring to me? I took a deep breath, determined to get through this as quickly and painlessly as possible, and peeled off the shorts. The girls -- let me just refer to them that way - - looked at my crotch and raised their eyebrows, which I ignored. They led me to a stall shower and handed me a plastic bottle of something. When I looked at it in puzzlement, not recognizing the brand name, Lotta explained, "Depilatory, dear." Carmen clarified, "Hair remover. Just rub it all over yourself and wait a few minutes for it to work." "And then let warm water run all over you, soothing, relaxing, awakening the woman inside." She tittered. "And once you're dry we can proceed to hiding your three-piece set." I closed the swinging glass door on the shower, which unfortunately wasn't frosted or rippled. The two TVs had a clear view of me, which they were enjoying shamelessly. I quickly smeared the creamy substance from the bottle all over me, making sure to do a thorough job so this wouldn't take any longer than necessary. Then I turned my back. Belatedly, I realized that now they were looking at my naked butt. But I didn't want to let them see how much that bothered me, so I just stood that way for several minutes, with my skin tingling, until they told me to shower off. There wasn't much room but I managed to get the water adjusted to a comfortable temperature before stepping under the spray. After I ran my hands all over myself I looked down and saw that I was hairless all over. Smooth and pink. It was a blow to my male ego. I was beginning to feel like I was being pulled down into unknown psychic territory. "Out you come," Lotta sang, holding up a large towel. I stepped from the shower and she wrapped it around me. Carmel patted my back through the thin covering. She was helping me to dry, though probably enjoying the touching as well. The contact bothered me. I stepped away and did the rest of the drying myself, hiding my nudity as well as I could. They each took a hair dryer and aimed them at me, sending twin jets of heat to finish what the towel had started. Special attention was paid to the area between my legs. When I was dry enough they hustled me to a seat. I tried to say something but was so distracted that I only produced a few disjointed syllables. Lotta took an old fashioned atomizer from among the plentiful cosmetics. She held it in front of my mouth telling me, "This will help your voice." Carmel instructed, "Open wide, angel." When I reflexively stretched my jaws apart, Lotta squeezed the bulb several times, sending plenty of the bottle's contents into my mouth. I breathed in the fumes and felt liquid run down the back of my throat . All at once my vision grew fuzzy. I felt lightheaded. And relaxed. Very unconcerned. Those feelings persisted as the two drag queens took an icepack from a nearby mini-fridge and pressed it against my genitals. My mind was curiously detached while they worked my privates into something extremely confining, and then applied some sort of medical- smelling preparation to the edges of whatever was now covering my crotch. The hair dryers were used again. A few more shots of whatever was in that atomizer were sent down my throat, leaving me even deeper in my artificially induced peacefulness. As they did more work in that area I was dimly aware of time passing. Then I slowly began to come around. "What...?" I blinked several times. "What did you do to me?" "Nothing much," Lotta insisted. "Just put a little something over your boy parts so you could pass as an honest-to-goodness girl. Remember, we're trying to help you win that bet with Darling." Everything came back to me. I stood up unsteadily and each of my he-she helpers took one of my arms. I still didn't like them touching me, but wasn't as bothered by it as before, because of whatever had been in that spray, no doubt. Carmel took a hand mirror and held it low and at an angle, so I could view what they had done to me below the waist. I gasped. Where my penis and testicles should be there was the perfect image of a hairless female vulva, so realistic that no one could have known it wasn't the real thing. I got my thumbs and forefingers on the labia and gently tugged but it refused to come off. "Oh," Lotta said with a sly smile. "That's not going anywhere. There's a snug little sheath that we tucked your candy into. And then the pretty pussy we put over top. Everything is glued on with a special adhesive that bonds wonderfully. I mean, there's no way to counteract it without a specific solvent." Carmel added, "But not to worry. We arranged you so that you can still pee through it. Of course..." She switched to a confidential whisper. "... you'll have to tinkle sitting down, like a real girl." She tittered and waved her hand with a limp wrist. The room seemed to tilt and I stood there swaying. They eased me back onto the chair and gave me several more squirts from that all-too- familiar atomizer. This time, in an even deeper stupor, I felt pinpricks on both side so my chest and then, while one of them assisted me in standing, each of my buttocks and hips. I drifted away for a timeless period and when I came out of it a got a shock that was worse than the false pudendum. Looking down at myself I saw that I had -- breasts? I lurched to my feet and leaned against the make-up cluttered ledge. In the mirror I saw a pair of round bosoms with protruding nipples. They were the size of grapefruits. The girls turned me around and said I should look back over my shoulder. When I did, I saw that my backside had become wider and fuller, a balancing accompaniment to my new bust. Lotta told me, "We just gave you some shots, dearest. They're almost done working. I mean, you might still gain another inch up top." Carmel added, "And a few downstairs. You won't have to use padding, or shaping garments, the way we do." "But, I didn't ask for any of this," I protested weakly. "You made that bet, didn't you? And you're determined to win it, aren't you?" I wasn't so certain anymore, but I also didn't see any way to back out. Maybe I could think more clearly if I could get into my own clothes again. "Listen," I said. "Just give me my shirt and pants, so I can feel more like myself for a while. Okay?" "Not okay," Lotta told me and then pouted. "Your male drag went into one of our lockers that wasn't being used. You know, to keep your property safe." "After all," Carmel reminded me, "your wallet was in your pants. And I'm sure there was cash in it, along with credit cards. Plus your ID. Not that you'll need anything to prove that you're Barry. Because you wont' be him. I mean not once we finish turning you into Berry. Besides, I don't know the combination for the lock. Oops." It was as if I had been dragged down into a vortex of feminization. I was still rather helpless from the spray as they dressed me. Then a make-up bib was put on and they worked on my face. My fingernails and toenails were painted. Finally, a long, reddish blond wig was settled on my head and somehow affixed. I had a bad feeling that they might have used that powerful adhesive again. That was when Darren reappeared. Except that now he was completely Darling. He had on a clinging mini-dress of metallic blue that showed off an attractive figure. As I sat there, gradually recovering from the most recent dose of the spray, he studied my face critically. "Our girl Berry looks stunning but needs a finishing touch, and I know exactly what it is." He opened a drawer and produced a hypodermic with a large chamber full of green-tinged liquid, and a short needle attached. "This won't hurt, Berry," he said as he removed a sterile cover from the tip. "Not much." As if at a secret signal, the other girls took hold of my arms. Darling began to inject my lips, moving from spot to spot until the fluid was all gone. I tried to say something and my mouth felt odd. When I managed to speak a few words, trying to question them, my speech was muted and slightly distorted. "That sounds good, Berry. Just pitch it a bit higher. Let me hear you." Feeling powerless, and deciding I had better go along with her request if I ever wanted to get out of this fix, I said, "Darling. What did you just do to me?" My voice sounded girlish and unfamiliar. "Just a little something extra to help you when you're out there under the bright lights of show business, Berry. Even though I made the bet, I honestly want you to win. Stand up, please, sweetie." I got up and she guided me as I was told to put my feet into shoes with three inch heels. They took turns leading me around until, in a surprisingly short time, I was walking with a minimum of trouble. That was then they pointed me to a full length mirror. The shoes forced me to take small steps. I minced toward the mirror and, as I got directly in front of it, someone turned on an overhead light that shone on me at the perfect angle. When I saw my new self, I was too startled to move. Looking back at me with wide eyes was a gorgeous, albeit overly sexualized, girl. She had thick hair, falling in gentle waves to her shoulders. Her face was heavily made up, with darkly outlined eyes, deeply shaded lids, pink cheeks, and a plum-colored mouth. But her lips were larger than they should be. She had a permanent pucker. As I experimentally opened and closed my jaws, the bizarre mouth stretched and contracted, those lips showing full mobility. When I really did pucker, they ballooned out even fuller. My body was encased in a shiny red dress that hugged me like a second skin. The scoop neckline exposed the tops of two boobs that had expanded from grapefruits to cantaloupes. I even saw a hint of nipple peeking out. I turned side to side, seeing how my newly thickened bottom was also shown off. My legs were in sleek stockings and those heels added definition to my calves. The complete absence of body hair heightened the overall effect of total womanliness. "Darling," I said to Darren, automatically maintaining my wispy falsetto. "Please. You have to do something. Just give me back my male clothes." "Well, if that's what you want. Okay." She paused, creased her brow, frowned, and said, "But I don't know the combination to that locker either. Gee. And here you are with no cash or credit and not one piece of identification. So unless you want to leave here looking like you do now, Berry, I suggest you do what I planned and compete in the club's contest, and do your damnedest to take first prize. If you lose, Lotta and Carmel are going to be extremely disappointed to see all their hard work go to waste. I can't be responsible for what they might do to you. I mean, an angry TV can be a nasty bitch. So how about it, hot stuff? Ready to strut it for the guys and gals in the club? Prepared for your premiere at the Pink Peach?" Instead of just passing as a girl, now I had to win some sort of competition. When had that change occurred? Still, seeing no other choice, feeling as if I had been separated from my male self, I nodded. In my new voice I said, "I'll do it. And then afterward, you can try to get the combination to that locker." "Positively. After you win." My astonishment at the transformation and concern over my predicament had sobered me up completely. Lotta and Carmel finished preparing themselves with the efficient speed of long practice, changing into showy dresses and donning exaggerated wigs. It was fascinating to watch them. They told me to lead the way. I moved toward the dressing room exit, my breasts jiggling in their braless state, and my enlarged buttocks rubbing against each other. As I moved I was very aware of how tightly my genitals were confined, which added to my sense of having been unmanned. They accompanied me down a dimly lit corridor. There was an open doorway through which I could glimpse the club. To my dismay, there was a full house. The audience sat at small tables, several on each of a half dozen risers, so that everyone had a good view of the stage I was about to step onto. I saw men who appeared entirely masculine, others who looked and acted like mixed-gender sissies, and what I had to assume were males attired and made up as females. Some of the latter group were obviously in drag but others might have been actual ladies. And I was pretty sure that there was also a smattering of biological women, though in that place there couldn't be absolute certainty. The confusion added to my mounting disorientation. I definitely had to do my best in the competition or I might find myself in some new difficulties. A Latino TV in a slinky yellow dress and piled-high hairdo introduced us simply as the evening's contestants. We sashayed out onto the stage. Darling, Lotta and Carmel swished around, struck poses, and threw kisses to the onlookers. I stood there for long seconds, numbly unresponsive. Then I got my mortification under control and began to mimic the others. I did everything they had done, despite my reluctance. Next I bent forward to put my hands on my knees. The posture made my plump boobs nearly pop free. I pursed my inflated lips and made a series of air kisses. Then I swung around, thrust out my burgeoning butt, and gave it a few wiggles. The onlookers clapped and whistled. I faced them again and pantomimed a deep curtsey. From the corner of my eye, I spotted Darling giving me an approving smile. Maybe she just wanted to put me through this to satisfy some whim of her own. And then I could return to my male self, with that prized jacket as my property. The others stepped down off the low stage. Darling reached back, took my hand, and tugged gently. "Come on, sweet cheeks. We have to do a walk- around so everyone can make their final decision. Unless you stopped being interested in winning." I moved off the stage and went with them, between the nearest tables. As they spread out to give everyone on that level a closer look, I saw some of the most manly patrons patting bottoms and squeezing thighs. My face grew warm and I knew I was blushing with shame, though it probably wasn't visible through the heavy rouge on my cheeks. But I wasn't going to lose the contest now, no matter what. I circulated, making sure to hit every table. Male hands fondled me appreciatively. My insides quivered. When men made suggestive remarks I was coy. It was awful to be handled and spoken to that way, but I kept my eyes on the prize. The next level of tables was the same, except that one guy in an expensive imported suit pulled me down onto his lap. I wriggled to get free but he mistook it for flirting. Breathing hard, I finally escaped and moved away. The third level had several bottom pinchers on it. The fourth included two tit gropers. My nipples slipped out and got fingered. I couldn't believe how intense the stimulation was. Maybe it was a side effect of being given female dimensions there. In response my penis tried to get hard. But because it was trapped in that tight sheath, below my fake pussy, and because it pressed crushingly against my testicles, I felt more pain than pleasure. I pulled up the top of my dress to get my tit tips back under cover. But the buzzing in my erogenous zones continued. By the time I reached the fifth level I couldn't think straight. Rude hands goosed me and rummaged under my short dress. Now every touch added to my unwanted arousal. I squealed and writhed, which only encouraged them more. They passed me from table to table. As my libido soared into the sexual stratosphere, I moaned and panted. That made them paw me harder because they thought it was what I wanted. My poor cock and balls were registering extreme discomfort and wild pleasure at the same time, the two becoming mixed together in my mind. The final level of that private hell, though fun for the three voluntary TVs, was unforgiving to me. A tall Black man with a foreign accent I couldn't identify took a special liking to me. He seemed to be someone special, because everyone else deferred to him. They all just watched, amused, as he bent me forward over the table to reach around from behind and toy with my faux pussy, which kept my penis as stiff as it could get in its trap, sent my sensual temperature even higher, and doubled the piercing ache between my legs. I heard some of the other guests address the man as Tandy while they were urging him to even lewder behavior. He complied by tugging down the top of my dress, freeing my bobbling breasts, and tying the shoulder straps together in a knot, behind my back where I couldn't reach them. I turned to Darling on my left and then Lotta and Carmel on my right, for help, but all that accomplished was to make my tits swing side to side. There was spontaneous applause as Tandy at last let me go, sending me on my way with a hard smack to my bottom. As we slowly descended back toward the stage, I had to replay all the humiliations I'd endured on the way up. Except that now my top was stuck in its lowered state. Worse, after everyone had seen how Tandy used me, many more felt free to push me to those limits. I noticed that none of the other TVs were being treated the way I was, like a slut. My boobs still exposed, dress hiked up in back to reveal that I had no panties, I got shakily back up on stage. My runaway horniness made my head spin. Please, I begged silently, just let me win and get out of here. The Latino Mistress of Ceremonies returned. She gave each of the others a kiss on the cheeks. When she got to me, the dusky young queen took my face between her hands and locked lips, shoving her tongue into my mouth. She rubbed her thigh between my legs, sending my arousal to unbearable heights. Out of control, I began to hump her leg. She toyed with my nipples, making it impossible for me to halt my obscene display. The frustration of not being able to get fully hard or to finish, made me grab her thigh and assault it even more fiercely. I was aware she was making crude jokes about my lack of restraint and provoking gales of laughter from her listeners. My balls were throbbing, and not in a good way. At last I slumped to my knees and stayed there, hugging her lower leg, no longer caring that she was an artfully disguised guy. The hostess stepped away and I almost fell on my face. While I got awkwardly back to my high-heeled feet, she went to each of the others and held her hand over their heads to gauge the reaction from the audience. Darling, Lotta and Carmel all got similarly tumultuous responses. But when she got to me, the sound level exploded. I was clearly the winner. At last, I told myself, this ordeal was coming to its end. "There she is," the MC shouted. "Winner of the coveted title, Queen of Bondage." What? Did she say what I thought she said? As I was gathering my wits, trying to decline that title, the MC took something and shoved it into my mouth. It was a gag and, when she twisted some mechanism, it expanded so that I couldn't have remove it. I shook my head violently, which succeeded only in sending my tits swaying again. There were cheers and guffaws and catcalls. The other three contestants had rushed off the stage, only to return an instant later, each carrying a piece of bondage equipment. Darling undid the knotted shoulder straps of my dress. Before I could do anything, she bent my arms at the elbows and tugged something confining over them. It was a single leather sleeve that held my upper limbs behind me in their uncomfortable position as she buckled attached straps all along its length. The bondage sleeve had the secondary effect of shoving my boobs out prominently at the audience. Lotta stepped in with a high posture collar. She fastened it around my neck and locked it in place. The thing forced my chin up so high that I couldn't see where I was going without bending forward. They walked me around like that, tottering on my heels, unable to speak, boobs and bottom jouncing with each step. Then the first two TVs worked down my dress, got it over my big butt, and had me step out of it. There were comments from the crowd about my false pussy. I desperately tried to hide it, as if I was truly a nude female, but to no avail. After letting me embarrass myself that way for several added minutes, Carmel stepped in with what she had ready to use on me, a red satin corset. As she pulled it around my middle and tugged on it, I could sense how tight it was going to be. Worse, there were pointed metal studs all over the inside, pressing into my tender flesh, not sharp enough to pierce me, but guaranteed to cause unending discomfort, especially when I moved. The others stepped in to help her as she snugged up the laces, more and more, until I was being squeezed without mercy. Carmel tied them off, compressing my middle further, until I had to breath carefully to keep from feeling swoony. The points dug in and made me whimper behind my gag. There I was, pink and smooth all over, pretend pussy blatantly shown off, head held high by that infernal collar, arms disabled thanks to the terrible sleeve, waist compressed to the point of torture by the diabolical corset. The MC wheeled out a long oval mirror mounted between two wooden uprights. The first thing I noticed was how weird my oversized lips appeared as they were stretched into a large 'O' by the gag. Then I took in the sight of the black leather and red satin contrasting with my white and pink skin. Cameras from the audience were taking pictures of me. Could this get any worse? I got a feeling that it could as I saw Tandy approaching, with a sheaf of twenty dollar bills in his hand. He called out, "I want to buy drinks for the entire room. And I'd also like permission to initiate our new Queen of Bondage with a good sound paddling. Does everyone agree?" The crowd roared. Sissies in various revealing outfits appeared from the wings, carrying round trays. I understood that they were waitresses. As they streamed among the tables, Tandy handed the wad of money to the MC, who held it aloft and waved it overhead, triggering more cheers. The party atmosphere grew as Tandy hooked a leash through a ring on the front of my collar and marched me around the perimeter of the stage, my tits bobbing and ass swaying, those heels again making me take dainty steps. After the third time around, he stopped in the middle of the space and attached the leash to a ring set into the floor. That forced me to bend far forward, my buns sticking out, the corset squeezing and jabbing me worse than ever. My arms hurt and my chin was still elevated by the collar. The MC had vanished for a moment but now reappeared holding a long, narrow sorority paddle, with the words Pink Peach cut into it. Tandy accepted the length of wood, hefted it, and took a few practice swings through the air. The MC stepped in to remove my gag. I took a deep breath. At last I could explain about that bet and how I honestly wasn't into these activities, didn't want to look female, and just wanted to get into my male attire and leave. I got as far as, "Please listen to me" before the first smack of the paddle landed on my bare bottom. There was a loud meaty slapping sound. I wailed. My feet shifted around but, with the leash hooked to the floor, all I could do was move slightly in my tall heels while more blows rained down. Tandy didn't let up until I had broken down and was sobbing, pleading incoherently for him to stop, and blubbering about being a good girl. He laughed and patted my blazing backside. His hand lingered as he stroked my sore buttocks, reached under to again tease my trapped genitals, and even used his other hand to diddle my nipples, which stiffened dramatically. My incapacitated cock tried once more to harden. I was soon a twitching mass of overexcited nerves, again seized by that unfamiliar tangle of pain and pleasure. The two were becoming inextricably linked in my mind. Suddenly Darling was there, with one hand on my leash. She unclipped it from the floor and took me for a shame inducing walk through the audience, where I was repeatedly caressed, tickled, and stroked. My sore bottom received lots of special attention. Afterwards, back on the stage, she used the leash to pull me near. "So," Darling whispered, wetting her fingertips and giving my firm protruding nipples some friendly feels, "congratulations on winning our bet. But the thing is that now you're looking all girly, with those desirable tits and that grab-worthy ass, along with oh-so-kissable lips. And there's no way for you to remove that lovely covering over your boy bits. Plus, all your male clothing, money, credit cards and ID are unfortunately in that locker... which is locked. So maybe we need to renegotiate our terms." "But that's unfair." "Yes." She smiled wickedly. "Isn't it? First of all," she went on as if she hadn't even heard my objection, "I think you'd better agree to cleaning my apartment for a month, like I said at the beginning. I have a perfectly yummy maid's outfit for you to squeeze your new curves into." "But..." I suddenly felt a new fear. "... aren't my... er... contours going to just go away?" "Well, here's the thing. You'd need a second set of shots to make the swelling go down. And those things aren't free. So you'd have to make a separate deal just to get me to think about helping you with that little difficulty. Or you could start buying bras and some sexy panties." I saw that my situation was not only bad, but complicated as well. Simultaneously, my attention was being divided by my TV friend's hands running over my smooth hairless skin. I'm afraid I didn't do a good job of bargaining. Which is why now, ten days later, I'm obligated to retain my sexy feminine figure and work at the Pink Peach every weekend, until further notice. In fact, I'm especially not looking forward to my special assignment for tonight. It promises to be particularly demeaning and to do a lot more damage to my already tenuous grip on what's left of my male personality. Here they come. Darling, Lotta and Carmel, who take a special delight in being my personal handlers. They are keeping me naked this time. And there's the clear Plexiglas box they've been dropping hints about. It's sitting on a low platform. I'm stepping into it, crouching down, lower and lower, sitting on the cool floor with my arms wrapped around my bent up legs. My boobs are resting on my knees. Now I'm ducking my head down so that my chin is in my cleavage and I'm looking straight forward. The hinged top of the box is being closed and it touches the top of my head. My three tormentors are reaching in through the round holes that there are several of on each side. Now someone is teasing one of my round tempting breasts. Another is tickling the sole of my foot. The last is behind me, poking a finger between my buttocks, finding their target and probing. Tandy appears in front of me. He puts his thick dark fingers in to stroke the underside of my chin. "My, my," he says with a smirk, his voice tinged with that exotic accent. "I hear you don't have to shave any more. You're smooth all over and will stay that way until you've finished your employment here at the club. And paying off some other deals you've made. Isn't that nice?" He retracts his hand and brings his face close to mine, kisses the tip of my nose. "And you know," he considers, "if this box were a little higher up, this opening would make it possible to use you for something really fun. I know they haven't started you on anything like that but I hear that, with all the feminization, and getting you all steamed up sexually while you still have your dick trapped under that pussy, it's changing the way you think. If you agreed to get into a relationship with me , well, with all my wealth and the influence I have around here, maybe I could help you with your dilemma." "I... I'll..." My uncertainty about so many things keeps increasing. "I'll think about it. Sir." "Well that's good," he decides, and winks broadly. "I hear that your friend Darling got you to take an indefinite leave of absence from your job. And she had you sign papers to put all your money and property into her name. In fact, she showed me pictures of all your male clothes being donated to a thrift store. You could certainly benefit from being with me, now that you're penniless and don't have anyplace to live. So think about it, Berry. I know you could make a fine housewife. Doing little chores in a cute apron... and nothing else. Being right there and available to me anytime I need to relieve some pressure. Maybe I could even take you back to my native country. But right now I'll leave you to be admired by your growing number of fans. We can finish this conversation later." As he walks away I see tonight's TV door minder greeting the first arrivals. They come directly toward me, where my box is sitting in a private alcove to one side of the stage. There's a light shining down on me, illuminating the non-removable cosmetics I've been given, my breasts and bottom which have grown in the past weeks, and the long eyelash extensions which flutter every time I blink. I force my pillow lips into a smile and lick them so they will glisten. More club-goers are entering in a steady stream. I'm really a hit. Darling is telling them, "We're going to play a game. Let's see how many times we can get Berry so excited that she ALMOST has an orgasm. She enjoys it so much when lots of people tease her and bring her right to the edge. She shudders and quakes but can't get there. Her dick is still squashed down under that lifelike pussy. But at least now she's learning to appreciate the pain she feels as much as the frustrated pleasure. So go on everyone. Get busy. And as other folks arrive, let them take a turn too. We're expecting a big crowd and Berry will be here all night, having her new kind of fun even while all our other activities are going on. For her it will be non-stop." That's where I am right now. I don't know what the future holds for me, though I've had some disturbing premonitions. Every time I make a deal to improve my lot in one area, it costs me dearly somewhere else. I'm becoming such a sex-obsessed airhead that I can't negotiate to my advantage at all. As more hands reach in to fiddle with me, to drive me to distraction, Tandy's offer sounds better and better. And please remember, if there is one thing I hope you've learned from my story, it's to be awfully careful if you make a bet with your crossdressing friend. ********* (This one is for my friend C.C. I hope you will check out C.C.'s engaging stories and leave comments on them.)