Date: Wed, 11 Jan 2023 17:05:57 -0600 From: Timi Darlington Subject: Settling a Bet Tranny Tales Stories of an amateur cross-dresser's fantasies and true adventures Settling a Bet Nearly everyone at the office gambled on something whether it be the lottery, the nags at the local track, sporting events or even election results. It really didn't matter as long as there was a bet being placed or being settled. Betting activity intensified especially during football season as we all chose the team and conference of our allegiance and negotiated the "over/under" endlessly. While cash was always a desirable form of settlement, some of the guys became rather creative in determining other forms of repayment including yard work, meal preparation, gift cards, theater tickets, etc. It was always in good fun and everyone cheerfully paid up on whatever arrangement was hashed out with the usual loser's retort of "wait `til next year". There were about six of us who were always involved. I was strictly an "Orange" fan and usually lost to the "Crimson" fans, Bob and Vick. There were some guys from south of the Red River, Buck and Richard. And, there was one man from the Deep South, Daryl, who moved here after a divorce that left him emotionally struggling and somewhat lonely. He never complained or talked about his past. Rather, he was always friendly and engaging especially when it came time to collect his winnings. And, being very loyal to one team of a certain maroon color back home, he collected quite often. Most of us were married but we were always welcome over at Daryl's apartment for cards, television or just to drink beer and shoot the bull. Everyone liked him and the women in the office loved him. He seemed to do well with the ladies but never settled on one. He stood well over 6 feet, with a square jaw, wide set green eyes and a dark, thick moustache. He was in his mid-40's, had a very attractive presence with a thick head of black hair with a tinge of gray and a muscular, hairy body from working out very regularly. He played some ball back in college but a badknee kept him from going further. Yes, I found him especially attractive. In a way, I admired him, wanted to be like him and enjoyed his personality. While I was happily married with kids, I enjoyed the male to male comradery at the office or at his apartment weekends. Ok, I was attracted to him for another reason and apparently he seemed to know. I was about average height and a little on the skinny side. I kept in shape, stayed groomed and ate all the right things. I fit in well with the guys in almost all of their manly activities. I lived the quiet "married with kids" life and by all appearances, I was just a well-balanced regular guy. However, I had two secrets. I was bi-sexual having various long term relations with mostly other married men. I loved being submissive when it came to man on man sex. While I was a little big to be considered a "twink", I easily attracted dominant men at bars or sex shops submitting to oral or anal sex. And. while not particularly promiscuous, I knew how to attract a man when I had the urge. However, my second and very delightful secret was that I loved to cross-dress. I'm not a stunning beauty. However, with the right makeup, clothing and a long, thick and curly dark wig, I can "pass" at a distance and in soft light. I took time off from work or had overnight business trips allowing me to dress-up and meet men or, when alone, play with an assortment of dildos. So, I was rather well seasoned by the time I reached my 40's settling in with a few mostly married men on a fairly regular basis. I could tell when a man might be coming on to me and, over time, I began to sense that from Daryl. There was the hand on my shoulder, or on the small of my back. There was the nudge with a foot when we sat together at meetings. But, most of all, it was that piercing look he gave me with those gorgeous green eyes. It seemed he could look right through me, reading my thoughts and knowing that I found him sexually attractive and would have loved a chance to be with him privately dressed up or not. Little did I realize that chance would come quite unexpectedly! The college football season was winding down with one of those very infrequent non-conference games in early November. It just so happened that it would pit my orange team against his maroon team. The guys were wondering how Daryl and I would wager on the game. The teams were about even with the game played at Jerry's World, a neutral site. We agreed that the usual wagering terms were a bit stale and, as usual we agreed that we had to accept whatever settlement the winner chose. Anything was open as long as it was safe and legal. It had to be accepted or we would face the wrath of our office colleagues. With a sly smile, Daryl insisted that I go first. I thought I was rather clever in deciding that if he lost, he would have to dress up as our mascot, a cowboy, and serve me lunch at the office. Not being able to reject my terms he accepted. Now it was his turn and I was shocked when he required that, if I lost I would have to dress up as a cocktail waitress and serve him drinks at his apartment. I thought it very strange that he would come up with this idea and pretended to be reluctant in accepting. Of course, very secretly, I was thrilled at the prospect! Oh, if only my team would lose. I wasn't sure if I should look like an amateur cross-dresser or if I should go all the way drawing from my years of experience. I knew that I really wanted to seduce him and perhaps that washis plan for me. So, I quickly decided to go the full distance with clothes, make-up and accessories. I reviewed my feminine wardrobe deciding on a crisply starched, nicely tailored white blouse and my ultra-tight and short black mini-skirt. Underneath I would wear my thigh top fishnets, my black lace trimmed panties, black corset and matching bra. For accessories, I would wear my usual complement of bracelets, rings, a favorite pair of earrings and a maroon scarf in honor of his team. I made my arrangements as to where I would dress up. Over the years, I made friends with owners and managers at various gay or gay friendly shops and bars. One gay barin particular would allow me to dress up in the rarely used ladies room. An "out of order" sign would deter anylady visitors allowing me time and privacy to cleanse for sex, apply makeup and dress up which usually took usually took about thirty to forty-five minutes. So, I was essentially ready for the game and hoping for a respectable loss for my team. And, that is the way it turned out. My orange team held up pretty well through three quarters but lost by two touchdowns. Now it was time for me to pay up. We decided on the next Saturday night. I told my family that the guys had a card game at Daryl's and a fourth player was needed. By Friday night, I could hardly sleepbeing so excited about the following evening and how things would go with Daryl. I rose early, secretly trimmed and shaved what body hair I had, snuck up into the attic for my hidden "girlie gear" and secured it all in the trunk of my car. To make the time go by, I stayed busy around the house through the morning and after-noon. I then showered, shaved my face very close, put on my thigh tops and my sexy, black lace panties, the kind that would secure my "male parts" very securely between my legs. With jeans and a shirt, I looked perfectly "male" to my family as I left. On my way to the bar I stopped at a liquor store for a fifth of Wild Turkey, Daryl's favorite. Now, I was ready for my "transformation"! The bar was already crowded and a wink from the bar tender was my ok to proceed to the "out of order" ladies room with my female attire and a glass of wine. I quickly douched my "pussy" wanting to be prepared just in case things went "that" direction with Daryl. I next applied some smooth, feminine body lotion on my legs, ass, arms and face. I next applied my make-up and a nice bright red lipstick, put on my corset, and bra. Next came the white blouse and mini-skirt. I finished with my jewelry and my maroon scarf. I smoothed out my make-up, added a little blush, put the make-up and lipstick in my purse and made a last check in the mirror. Whew! I was ready, ready for the guys in the bar and ready for Daryl! In the soft light, I looked very fetching. I hoped he would see me the same way! From the whistles and cat calls from the bar, I knew my efforts were appreciated. I gave my male attire to the bar tender for safe keeping as he leaned over to give me alittle "good luck" slap on my ass. I couldn't have been more confident as I finished my wine, left the bar and settled into my car. The drive wasn't too far and I felt very comfortable with my appearance as I pulled into the parking spot nearest his apartment. All was quiet as I grabbed my purse, Daryl's "Wild Turkey" and climbed the steps to his door with my 4-inch heels "clicking" on each step. I stopped in front of his door, took a deep breath and rang the doorbell. I waited several seconds and rang it again. I felt a flush of anger thinking he stood me up and was probably out somewhere with the guys picturing me standing here and laughing. But, no, he wouldn't do that, would he? My question was answered as the door opened just a few inches. Lights were on inside and I could tell it was Daryl. He hesitated wondering who this "woman" was at his door and then realized it was really me. The door flew open and he stood there, gawking at me! Finally, he said "Holy shit! Is that really you?". "Yes", I responded, I've come to be your cocktail waitress, remember? Now, let me in." He stepped back apparently in shock from my transformation while I brushed by him and proceeded to his kitchen. My heart was pounding realizing that I must have made the impression that I had hoped for! He recovered sufficiently enough to close the door and followed me into the kitchen. I could feel his eyes on me,looking me up and down as though they had fingers. I proceeded to make him a drink and realized he had already been drinking judging by a half empty bottle in the sink. I reached for the ice in the fridge turning just enough to see him and I noticed a nice bulge in his jeans. Now, my heart beat even faster. Was I ready for this? My hands were shaking as I made his drink and I said, "Go make yourself comfortable and I'll bring your drink". He complied and I could hear him turning the television on to a football game. I brought him his drink, walking rather effeminately with a slight swing of my hips and returned to make a weaker drinkfor me. I had to hold my liquor. If we were going to have some "activity", I sure as heck wanted to remember it! I returned to the living room, not knowing exactly what a cocktail waitress does when her "customer" isn't ready for another round. So, I started to straighten up his living room nervously waiting for him to say something, anything! It wasn't like him to be so quiet and he wasn't watching the game, he was watching me. Finally, he regained his usual confident macho composure and asked, "Why don't you sit down?" This presented me with a dilemma. There was only a sofa and his favorite easy chair. Instead of taking his easy chair, he was sitting in the middle of his sofa. I could either take the easy chair or sit very near him on the sofaeither to his right or his left. He seemed to enjoy my confusion and said, rather firmly, "Sit here" as he patted the sofa cushion to his left. Now, my heart was pounding, and I could feel my nipples tingle and my pussy tighten. He now seemed fully recovered from the shock of my appearance and I could feel a certain tension, a sexual tension, in the room. I sensed that this was going to be fun and "sexciting"! I smoothed my skirt behind my ass as I sat down next to him, not quite touching, but just a few inches apart! He immediately put his left hand on my thighs and began caressing them. "Nice legs, baby. I had no idea how nice." His hand went further up my thigh and under my skirt. Oh, it felt so exciting feeling his warm fingers working their way up inside my skirt. "You went all out for this, didn't you?" he asked. "I just wanted to settle this bet with no questions asked by you or the guys," I replied. His fingers reached all the way up to my panties and caressed my "clit" still tucked securely underneath. "I just want to be sure you're not a real woman," he said as he gently squeezed my balls. "No, it's the same me. Sorry to disappoint you," I said. "Oh, you're not disappointing me at all" he replied. As his left hand fondled me underneath, he reached over with his right hand and squeezed my breasts, or at least my falsies. "I really like what I see and would like to see more," he said as he leaned over me his face just inches from mine. I could smell liquor on his breath. He obviously had been drinking heavily perhaps anticipating this moment. He asked "who did your make-up?" I responded "I did". "Well", he said, "you did a fantastic job for an amateur." "Maybe I'm not that much of an amateur," I said. "Doesn't look to me like you're an amateur," he said as he pressed his lips against mine. I wasn't sure if this was happening or a dream or just how much booze he had consumed. He kissed me harder with his tongue searching for mine. He pushed me against the arm rest of the sofa and got on top of me. His left hand was groping rather roughly inside my panties, reaching around to my ass. His right hand was behind my neck pressing my mouth against his. "I really need you, baby", he whispered, "and I need you right now". Fingers were now feeling their way toward my pussy, and I could feel them dart in and out probing deeper and deeper. I wiggled and squirmed but he had me firmly pinned. "You really like this don't you?" he asked. "Mmmmm, this is turning out to be far more than what we agreed upon", I replied. "Well, why don't we take it a little bit further?" he asked as he looked into my eyes. "Yes", I responded. "But, please let me freshen up your drink," hoping he would let me go. He relented and released me. I grabbed his glass and escaped to the kitchen. Now it was my turn to be in shock. His advances frightened yet excited me! I fixed his drink and returned to the living room. I took my purse and excused myself to go to the bathroom and freshen up. The wine from the bar and the "Turkey" were getting to me and needed a moment to collect myself. I realized that I was enjoying this way too much and I was more than ready for what would surely come next. I wasn't disappointed. When I returned, the lights were out, the football game was replaced by some she-male porn and Daryl was reclining in his easy chair having stripped down to his underwear that barely concealed anenormous dick. "Why don't you put your pretty lips and tongue to work?" he asked as he caressed his "package" motioning me to kneel before him. I knew I wanted this, I needed this and I had to have him! I slipped out of my heels and knelt before him caressing his legs and thighs before reaching for his tight briefs. I pulled them down his legs and off. He eased forward just enough allowing my face to come within inches of his gorgeous, manly "equipment". His strong musky aroma aroused me more and I was almost salivating as my lips kissed the head of his dick. I then kissed his balls and licked around the base of his balls and shaft before licking underneath his dick and back up to the head. I next rubbed the head against my lips before taking it in my mouth still licking it. He moaned softly as I took more and more of his dick in my mouth. He was easily 8-inches, maybe more, as it thickened and hardened. As much as I tried, I couldn't get it all down my throat and gagged with each effort. I saw him grin. He knew the size of his dick was a challenge to swallow. Yes, I was too excited and forgot to relax. With a little more effort and attempting to manage my breathing, itfinally slipped past the back of my mouth and into my throat. He looked surprised but pleased. My hands continued to caress his legs, thighs, nipples and played with the thick black hair around his dick and on his massive chest. I don't know how long I sucked his dick. I was in another world enjoying the smooth flesh of his shaft gliding along my lips. He was rock hard and moaning as I licked, kissed and sucked him. I could tell as he moaned louder that he might cum and I immediately backed off to lick and suck his balls. Then, I resumed sucking him. But, this time I went a little longer as he moaned louder. I was now tasting his pre- cum.He lifted my face and said, "Oh, no, I'm not just getting a blow job. I want to fuck your tranny cunt". We rose and changed places. This time I was on my back in his easy chair, my legs spread with him kneeling between them. He unbuttoned my blouse, squeezing my real breasts under my bra, pinching my nipples. He then pushed my skirt up to my hips and pulled my panties off before taking my "clit" into his mouth. I loved having this gorgeous he-man sucking me with my legs around his neck. He sucked me hard and long and I was responding, moaning louder and feeling myself coming close to orgasm when he stopped, rose to his feet and positioned his still hard dick against my tummy. He spat into his left hand and lubed my pussy, shoving his fingers into me as I winced in pleasure and pain. Satisfied that I was lubed and clean, he lifted my legs over his shoulders pinning me against the seat cushion of the chair and shoved his dick through my sphincter and deep into me with one might shove. The pain was intense! I screamed and almost passed out as he thrust in and out of me quickly and violently. He put his right hand over my mouth to muffle my screams until I adjusted well enough into the rhythm of his pounding and moving my body as much as I could to cushion each inward thrust. "I didn't know how good this would be," he said. "Fuck, this is so damn hot!" He fell into a slower rhythm as he continued to fuck me and I began to enjoy the many pleasurable sensations of being taken by a man, being firmly in his grasp, hugging his shoulders with my legs, caressing his hairy chest with my hands, squeezing his dick inside me and feeling his hardness gliding into my softness. If this was evenremotely like being a real woman, I was totally on board! I was moaning softly now, uttering a sigh with eachthrust, thoroughly enjoying this man that I had secretly longed for. I could feel him slow and begin to moan louder. He started stroking my "clit" making me cum and then he started banging me faster and faster. As I climaxed, my sphincter tightened around his dick which only increased his pleasure until he yelled "Oh, Fuck!" as he came, thrusting even faster deep inside me. The combination of his intense sexual release and the booze finally took affect and he collapsed on top of me. We rested in each other's arms enjoying the after-glow of our experience when suddenly, the doorbell rang! We both took a moment to gather our senses. The doorbell rang again and we could hear voices. Daryl said in a hushed voice, "Oh shit, it's the guys from the office!" "Yes," I said, I recognize Vick's voice." The doorbell continued ringing and Daryl yelled' "Just a minute, assholes, I'm coming!" Daryl started straightening up the living room and handed me my panties and said, "Why don't you go to the bathroom, freshen up and I'll get the door." I took the panties, grabbed my purse and shoes then headed for the bathroom, straightening my skirt and blouse. I could hear Daryl pull the porn out and resume the football game as he headed for the door. Sure enough, the gang was all there with Bob, Vick, Buck and Richard rushing in carrying beer, chips and ice asking"Where is `she'?" to which Daryl responded "Well `he' is in the bathroom". Richard yelled, "Hey, cocktail waitress, show me some tail and I'll show you some cock!" much to the amusement of the others. With my panties back on and my make-up refreshed, I reluctantly returned to the living room. I managed to say "Hello, guys," in a semi-feminine voice to which I was greeted with whistles and lots of sexually verbal abuse. I could feel myself blushing, dressed as I was, in front of all the guys from the office. Daryl could have easily joined in their amusement. However, to my surprise, he jumped to my defense telling them to "shut the fuck up! `He' did a good job in settling a bet on my terms and my direction." And, he added, "there better not be any word of this beyond tonight or I'll kick some serious ass!" The guys reluctantly agreed as they circled around me, inspecting, and admiring, my wardrobe and make-up. "Wow, you sure look good!" Vick said and they all nodded in agreement, chuckled to themselves and then settled into party mode. It was getting late with a west coast game already into the 2nd quarter. There I was, cross-dressed with five guys from the office when ordinarily I would be just another one of "them". Much to their disappointment, I decided to excuse myself and left. I drove straight to the bar to change into my male attire and scrub off my make-up before returning home with my female attire safely stowed back in my car. Daryl and I continued to meet secretly several more times and our love play was just as intense each and every time as it was the first time. No one ever suspected or would dare confront Daryl if they did suspect. But, Daryl needed something more from someone full time. He longed for home and to return to his Deep South! Eventually, he found workthat took him back home. We parted friends and lovers remembering the hot sex we had. Oh, but I miss him still and smile every time someone mentions my paying up on "The Bet".