Tranny Tales Stories of an amateur cross-dresser's fantasies and true adventures
The Tail Light
I've dressed up and have gone "out on the town" surely a hundred times or more over the years and with just a few interactions with the police. Knowing that I'm cross-dressed, they have always been very polite and courteous. They're kind to address me as "ma'am" although I would rather be addressed as "miss". I don't think they really want to deal with cross-dressers unless they are misbehaving rather badly. I respect them and don't want to invite trouble. As such, I'm very careful about drinking, avoid the appearance of soliciting men for sex, don't get obnoxious and am always polite and friendly. The one thing I am meticulous about is my car. When cross-dressed, I want to be sure my car is in sound mechanical shape with all lights working and the registration up to date. Oh, but was I in for a surprise!
Business travel allowed me a night to myself in a good sized city just across the state line. The bars and sex shops are few. But, the ones they have are usually fun and I would frequent them whenever I had the opportunity to dress up. So, once my business was done, I hurried to my motel to douche (just in case the right opportunity came along) and applied my make-up before dressing up. Being mid-Spring, I chose a simple combination of a light blue blouse, a charcoal gray mini-skirt with a pretty floral scarf. Underneath I wore my usual black corset with a pink bra and matching panties. With my fish-net thigh tops on and long curly black wig carefully fitted, I was ready by early evening. I checked my make-up once more, added some jewelry and I was out the door to my car enjoying a few curious looks from other motel guests.
I first stopped at a popular gay bar near downtown and enjoyed some wine and few winks from some of the local men who strolled in, possibly from work, for a drink before going home. I glanced through the local gay publication before gathering up my things and left for another bar on the far south side of town. It was all routine as I made the "circuit" visiting the usual places at about the usual times. I wasn't in any hurry. I was totally relaxed, dressed up and feeling pretty and confident. So, it didn't bother me when I noticed a police car parked across the street from the bar. Actually, I felt safe knowing they were there and never gave them another thought. They certainly could have noticed my legs. At least they had the opportunity!
The bar was somewhat quiet as it wasn't quite 9 pm. I settled down for a tonic water and lime being careful not to imbibe too much wine at too many bars. I struck up a conversation with one of the patrons, munched a little popcorn and watched part of a baseball game. The time passed very quickly as it always does when I'm dressed up and out for an evening. Visiting bars and sex shops is so much fun when cross-dressed. I didn't want the evening to get too late with more places to visit. So, I made a quick trip to the restroom to "tee-tee" and checked my make-up before leaving. I went to my car and left the parking lot not even thinking to check if the police car was still parked where it was earlier. And then,
My car was lit up with flashing blue and red lights and then I heard a short burst of a siren that usually is an "invitation" to pull over. I carefully signaled and pulled off from a busy thoroughfare to a quiet residential side street, turned off the motor and waited. I could hear my heart pounding as not one but two policemen approached my car, one on the passenger side with the other at my window motioning me to roll my window down. With his flashlight illuminating my face he asked in a very even voice, "License and insurance, ma'am." I fumbled in my purse for my wallet and driver's license and fished around in the glove compartment for a current insurance card. Fortunately, I produced both and waited for the inevitable comment....
"You don't quite match the picture on your license, ma'am", again in an even voice. I responded with "No, I don't, at least not this evening, officer" in a firm, confident if not completely feminine voice. Surely, he could hear my heart pounding. While he and I were establishing my true gender, his partner tapped on the window instructing me to roll it down. I complied and he turned on his flashlight looking in the back seat, the front passenger seat and then on my legs. I could almost feel the hot beam of light working its way from my heels to the hem of my skirt about mid-thigh and then to my tight blouse. He didn't say anything. His flashlight was doing all the talking. Finally, I summoned my courage and asked in the softest voice I could muster, "Is there anything wrong, officers?" The officer on my side of the car, officer "Williams", from what I could read on his name plate, said, "Your left tail light is out. We're just doing a routine check. We want you out-of-state folks to be nice and safe." His response seemed a little too courteous if not condescending. Oh, but I was relieved. I could deal with a little condescension. Surely, they would let me go with a warning.
While his partner continued to hold the light on me, officer Williams took my information back to the police car. Obviously, they were enjoying my "situation" as my name and license plate were checked for any warrants or other infractions. Ok, it would take a few minutes, but I could feel myself relax. Yes, in a few minutes he did return, handed back my license and registration. "You be careful, dressed as you are, ma'am. You could get into a lot of trouble around here." I thanked him for his advice hoping our visit would be ending soon when I saw the flashlight shine behind me and heard "Hey, what's that under the passenger seat? "It looks like a bag of something. Oh, shit, Pete! It looks like a bag of weed! Hey, Bud, there's a lot there, enough to get `him' on distribution." Instantly, I became "masculine" again and things were only going to go from bad to worse!
Their sudden "discovery" had me shocked and as scared as I've ever been in my life! The last thing I needed was to be arrested while cross-dressed and charged with attempted distribution of marijuana. How on earth would I be able to keep this from my family, friends and my employer? Oh, but what they told me next was even more frightening. "I guess we're going to have to book him' and send him' over to county, Pete." "Yeah, Bud, and you know what will happen to him' at county!" Pete said with a chuckle. "Shit, Bud, he' could be not only raped but killed!" "Yeah, too bad for `him'", Pete answered, "He'll' be a lot of fun for Bubba and his gang!" Why was I being framed in such a terrible way? What were they up to?
Now, the realization came full force! I was not only going to jail, I was going in cross-dressed, a sissy in a skirt, exposed and possibly raped by a bunch of thugs in jail. I would be lucky to survive arraignment. I would likely not need to worry about my little secret being revealed to friends, family and employer! I don't remember who. It may have been Pete that "Mirandized" and cuffed me, placing me in the back seat of the patrol car. While I sat, with the cuffs digging into my wrists, they returned to my car searching for more "evidence". It all seemed so surreal. I was bewildered and frightened. But, I managed to collect my thoughts thinking that I would be in deep shit no matter what I did from this moment on. And, the thought of Bubba and his boys enjoying me necessitated a plan, a desperate plan with risk, but a plan that might work! I had two names: Pete and Bud and I decided I would appeal to them in the only way a "woman" could!
In minutes, Pete and Bud returned to the patrol car. Pete got into the driver's seat while Bud took the seat next to me in the back. It was time for my "performance". "Guys," I said, "I don't do weed, and I don't have friends who do weed. I don't distribute weed" I said in an ever mournful way. "Furthermore, you know I'm a guy just being a girl for a little while. I never cause trouble. I'm clean. Please, Oh, please! Is there anything, ANYTHING, I can do?" I asked with a sniffle. Pete and Bud looked at each other and then they looked at me. Almost simultaneously, they both said, "Let's call Mike". I had no idea what that meant or who Mike was. But, I sensed I might be safe hoping that this Mike guy might have mercy. If it took a few blow jobs or getting my ass fucked my some policemen to avoid being raped and my secret life exposed, it would be well worth the experience. And, the naughty side of me thought that it might even be fun!
Pete and Bud left the car to call Mike. For some time they looked back at me only to continue talking. At one point, Bud returned to take pictures of me apparently intended for Mike. Several minutes later, they returned. Pete, who seemed to be the senior of the two, said, "Mike said to blindfold you and bring you and your car in. But, don't be frightened. Mike thinks we can work something out." Bud took my car keys and proceeded to my car while Pete blindfolded me with an old rag from under his car seat. Just before he secured the blindfold, Bud had already started my car and it was then I noticed that one of my tail lights was indeed out! Yet, I knew I was being framed, framed for what purpose I wasn't sure but I was soon to find out.
Blindfolded as I was, I had no idea where we were going as various turns were made that apparently put us onto a freeway as Pete accelerated and the pavement smoothed out. It wasn't long though, that he slowed down to exit and we were back on a surface street as he stopped at traffic lights or stop signs. I then sensed that he pulled off on a county or farm road as I could hear gravel under the car. It seemed like another fifteen minutes or so when he turned again, this time it felt like a bumpy dirt road, perhaps an entrance to a farm house or a pasture. Finally, the car stopped, Pete opened my door, assisted me out of the car and then led me some distance until we arrived at a door. Once inside, he helped climb a flight of stairs and through another door. I sensed there were others present with some country music playing in the background.
My blindfold was removed and I was blinded once more, this time by a brightly lit bedroom. As my eyes adjusted, I became aware that there were various people looking me over and talking. Off by himself, was a giant, rough-hewn Hispanic male, seemingly a confused captive, just like me. There were my two policeman "chaperones", another tall, muscular black man and a very attractive white woman sitting in an easy chair. Everyone was clothed accept for her. All she wore was a smile as she inspected me and the Hispanic man while giving instructions to Mike and Bud as to where to place various lights and reflectors. She looked almost exactly like a Liz Taylor with the same pretty eyes and long, thick, dark hair. Oh, I was no match for her. She was of course anatomically correct, in every way a total female right down to her shaved pussy and with beautiful D cup breasts while mine were only little sissy A cup sized.
I was thinking that Mike must have been the black man when my thoughts were interrupted by the woman calling out to me in a rough, condescending tone, "Hey, bitch, you know why you're here, right?" Not knowing how to respond, I nodded my head up and down. "We've got something on you, don't we?" she snarled. "We've got enough on you to put you away for a few years. This state doesn't tolerate sissy cross-dressers that sell marijuana across state lines", she continued. "Yeah, you can fight the charges and claim we framed you. But, there's all of us and just one of you." And, with even more harshness she added, "Yeah, you can fight us. But, we can fix it so you'll be several hours in jail. Dressed as you are, your jail mates will have lots of fun with you, you little bitch!" I hung my head, weighing what options I had when she said, in a much softer, motherly tone, "Or, with the right attitude you can have some safe and fun play time with us. Would you like that instead?" Again, I nodded. She then turned to Pete and asked "Is our little bitch clean?" Pete responded, "Yes, Mike, there are no priors, no warrants, she's clean." It was then that I realized that "Mike" must have been a nickname for this woman who seemed to be in total charge. Perhaps it was short for Michelle.
Anyway, Mike responded with "Fuck, I figured that. What I meant was is her ass clean?" My arresting officers looked at each other and they looked at her gesturing "we don't know" to which, Mike grumbled..."Must I do everything myself? Henry, check her ass!" This time, the black man spoke up asking me "Are you clean, bitch?" Once again, I nodded yes. "Un-cuff her and bring her over to me." It was a great relief having my wrists un-cuffed. I massaged them as Pete escorted me to where Henry stood. Henry said. "Lift up your skirt, bitch and pull down your panties". I did as he commanded. From out of night stand drawer, Henry grabbed a large dildo and a jar of Vaseline. "You better be telling the truth, bitch!" He took the Vaseline, smeared some on his fingers and inserted them in my pussy. First his middle finger followed by two more fingers entered me thrusting deeply into me. I winced with pain as he forced them still further. Finding nothing, he lubed the dildo and instructed me to bend over.
I could see Pete and Bud operating some cameras. Pete was taping my "inspection" while Bud started taking still shots. Henry led me over to the back of another easy chair and forced me to bend over the top. While Mike held my arms down, Henry shoved the dildo into me. Oh it hurt! But, I was so glad that I cleansed and tested myself with my own dildo earlier that evening. Otherwise, it could have hurt far worse! While Henry repeatedly fucked me with the dildo, Mike continued to hold my arms securely against the chair. She was extremely strong for her size and my arms ached as she held them firmly. Satisfied that I was clean, the cameras stopped and Mike said. "Good bitch, nice and clean! But, either way, that Mexican is going to fuck you tonight!" I glanced over to their Hispanic "guest" who looked very confused and somewhat frightened. However, there was a noticeable bulge in his jeans!
"But first, bitch", Mike continued, "You're going to eat my pussy and suck Henry's dick. Remove your blouse, skirt and bra!" she ordered. The cameras started again, focusing on me as I undressed feeling very self-conscious as everyone gazed at my little breasts and pink "perky" nipples. I was told to kneel on the floor facing the bed. Mike sat on the bed with me in between her smooth shapely legs. "Eat it"! She ordered and I eagerly complied. It had been several years since I had pussy to eat. Although I much prefer sucking dick, I do like eating nice clean pussy. I slowly started licking her crotch getting it nice and wet before tonguing her labia finding it very sweet. Her pussy tasted good as I tongued deeper into her vagina taking time to tease her clitoris. I could tell I was making a good impression as she began to moan while forcing her pussy against my face. She moaned louder as my tongue probed deeper, as deep as it could go! She started to moan even louder as I brought her to orgasm alternating between licking her mons venus, nibbling her clit and fucking her with my tongue. She was now wet from my saliva and her cum. I must have passed the first test as she withdrew, saying, "You're pretty good, you'll be my little bitch-kitten". Now, let's see how good you are at sucking dick.
Still on my knees, I turned to face Henry or, more accurately his dick, completely erect and pressing against my face and lips. I could almost feel the cameras on me as I gently kissed and licked his large pendulous black balls enjoying that musky manly aroma, I then kissed the head and then licked it getting it nice and wet. I then proceeded to lick up and down his shaft. Oh, it was very large, easily 8-inches and thick. I continued to lick it getting it nice and slick so that it would easily slide down my throat. But, Henry wasn't a very patient man. He forced my head against the edge of the bed and began to fuck my mouth, driving his dick down my throat. I couldn't breath and gasped for air between each thrust. I started counting trying to focus on breathing and not gag but soon lost count after about 50 thrusts when Mike said. "Hey, honey, don't forget you're supposed to be fucking me! Don't let our bitch-kitten make you cum!" With that, Henry withdrew allowing me to gasp for air. I couldn't help but notice that their other "guest" was watching very intently and the bulge in his pants was even larger!
The cameras switched to Henry and Mike as he mounted her driving his huge dick into her pussy both lubricated by me as preparation. While they fucked, Pete lifted me up by the arms and pushed me over to the Hispanic. He looked me over in a very curious but friendly manner. Our language barrier didn't seem to interfere with what I could only interpret as mutual interest. Not knowing his name, I decided to name him Jose'. But, our attention was drawn back towards Henry and Mike as she squealed and moaned with each thrust. They then changed positions with Mike on top of Henry, sliding up and down on his gorgeous cock. Oh, how I envied her for having a real pussy. I could only imagine the pleasure she was feeling! Yet, I enjoyed the pleasure of a good dick in my sissy-pussy and my attention returned to Jose' who was fondling himself watching the action on the bed. Mike and Henry continued to make love while we watched. Finally, Henry let loose with a loud "FUCK!" and I could almost feel his cum pumping into Mike's pussy!
Come here, bitch-kitten," teased Mike. "Come and have some cream. Come fetch, bitch-kitten". I was somewhat familiar the term "fetch" in sex play and yes, Mike motioned me over to the bed telling me to get on my back. Again, the cameras focused on me as Mike straddled my face instructing me to "fetch" Henry's cum out of her pussy! Her pussy was just above my mouth as I licked it with my tongue, gingerly at first and then my tongue reached up inside her labia, licking it harder and stretching it such that Henry's cum could slide into my mouth. My tongue, Mike's pushing and gravity all seemed to work in unison as Henry's cum started to drip from her pussy. As the cameras closed in, still more of Henry's cum spewed from her pussy and onto my tongue and lips. The taste and scent of his juices mixed with hers made for a delightfully tangy cocktail as I eagerly swallowed and swallowed. Finally, the flow of cum slowed to a few drips and Mike rose, getting off of my face. The cameras stopped once again and everyone seemed to be delighted with my "attitude". It seemed all eyes and the cameras were now focused on my Hispanic friend and me!
We needed no rehearsal or directing as Jose' and I turned to face each other, oh so very close to each other. He reached out putting his hands on my hips while I put my arms over his broad shoulders. Even in my 4-inch heels he was still a few inches taller. It felt so warm and natural to be in his embrace. He gradually reached down to squeeze my ass while I started to unbutton his shirt to caress his chest feeling his coarse, wiry hair underneath. He kissed me hard on the lips, tonguing me, leaving me with the faint taste of chewing tobacco. Oh, but I didn't mind. I love being hard kissed by a real He-Man! He then grabbed me by my shoulders and reached down to take my left breast in his mouth, licking and nibbling the nipple. He then went to my right breast, holding me tightly against him. He smelled of sweat and a little bit of gasoline after what I assumed was a hard day of yard work. Oh, but I didn't care. I imagined myself as his wife, welcoming him home and offering my body to relieve the stress of his day. I quickly removed his shirt before undoing the button of his jeans that could barely contain the bulge between his legs. His large dick almost leaped out of the confines of his briefs pulsing with anticipation as I gently caressed it. It wasn't quite as long as Henry's but even thicker! Oh, this was going well and our audience seemed to enjoy each moment.
I was scarcely aware of their presence, the cameras, and lights as I went to my knees wedged between his delicious looking cock in front of me and the edge of the bed behind. His musky, manly aroma was even stronger and that was understandable after a hard day of labor. Again, I didn't mind as I caressed the head of his dick. Oh, it was so large and already oozing with pre-cum. I gently kissed and licked the pre-cum and then commenced to lick the shaft of his dick getting it nice and slick before taking as much of it into my mouth as possible. My hands caressed his balls, his legs and reached up to his chest to caress his nipples. He whispered something in Spanish before ramming his dick into my mouth and down my throat. My head was already against the edge of the bed. I had no choice but to take it, take it all as deep down my throat has he wanted. I choked and gasped for air. I heard still more Spanish. But, it was unintelligible to me as I struggled for my next breath. Oh, but I was loving this, loving taking a Man, this beautiful, dark man in my mouth!
All at once, he lifted me up and dropped my on the edge of the bed. As the cameras zoomed in, he pulled my panties off, spread my legs and rubbed his massive dick on top of my little clitty-dick. I was still well lubed from being fucked by the dildo and could feel the wetness in my "pussy" as he fingered me. He then knelt down to lick my clitty-dick and pussy. His big, powerful tongue forced its way in scratching me, tickling me with his day's growth of coarse whiskers. Oh, it felt so heavenly! I squealed in delight, wiggling my hips from side to side and thrusting against his mouth. I couldn't get enough! I've enjoyed having my pussy "eaten" before. But, Jose' performed with such passion and intensity. It was ever so obvious that he knew what a tranny enjoyed! In an odd way I felt the same way Mike did when I was eating her pussy.
But, it was very obvious that he wanted more, much more! He rose, lifted and spread my legs wide and planted his huge dick just outside my pussy, caressing it with his dick head. He leaned over to kiss me telling me something more in Spanish, perhaps something very sweet. He then nibbled my perky little nipples once more as he thrust his dick into me. The initial pain was intense! I let out a scream as he held me firmly against the bed, his pelvis banging against my ass and his dick firmly in me. The pleasure-pain experience was the most I ever felt with a man. I've had bigger dicks in me but no one matched his passion, his intensity as he drove deeper and harder into me. I thought I was going to black out from the shock and pain of his entry. But, the pain finally subsided and I started to enjoy feeling him in me, watching his heavy body thrusting back and forth against my ass as he moaned with ever mounting pleasure.
Suddenly, he withdrew motioning for me to turn over on my tummy with my legs spread and my toes touching the floor. Again, he thrust into me and again the pleasure-pain sensation resumed. He must have enjoyed the soft tissue of my ass as he grabbed it, squeezing it, before putting his hands around me, holding me tight against his pelvis forcing himself still further into me. His moaning became louder until he climaxed with a loud, shuddering Spanish expletive. His thrusting subsided until he withdrew resting his still engorged dick on the groove of my ass. I could feel the last drops of cum dripping on the small of my back. Never had I felt so feminine, so complete, so satisfied in pleasing a man! I was in another world at least for these delicious minutes. I heard the cameras stop while Jose' rested beside me, holding me against him. The world seemed to be surreal, dreamy and relaxing as we cuddled. But, another reality set in.
"Get up, little bitch kitten, you did real well! That wasn't acting. You were really into it weren't you?" I shyly nodded yes. "You're going to be ok with us and what happened tonight?" Again, I nodded yes. How could I possibly deny having the time of my life, held captive during a fantastic, wonderful night? Part of me wanted to stay for more and part of me wanted to escape to my motel room just to savor what had happened as I could still feel Jose's dick deep inside me, still tasting his kiss. I rose, recovered my clothing and Pete handed me my purse and escorted me to a bathroom. There I dressed and did my best to restore my make-up. Mike and Henry thanked me for my "services", told me I was free to go and that Pete and Bud would take me back to town. I asked whether Jose' would be free to go as well. They assured me he would.
With their cameras stowed, Pete and Bud escorted Jose and me back to the police car. We were again cuffed and blindfolded as Bud again followed in my car. I was returned to the bar where I was "arrested". Our blindfolds were removed and I looked once more at Jose'. He was smiling at me with such fondness that I had to give him one last kiss before getting out of the car. Separated by language, geography and culture, Jose' and I would never see each other again. Oh, but the memory would linger forever. Bud tapped me on the shoulder. I turned to face him as he put a small light bulb in my hand. "Better get that light fixed." he said with a smile. "I'll be sure to." I replied. But, that bulb still remains in my keepsake box!
Greetings all!
While my tranny name is Tricia Louise i go by Timi these days. If You got this far, i hope you enjoyed my story. While i'm a little more into "retirement" these days, i still enjoy "femming up" a little and visiting friends, bars and sex shops occasionally.
Sweett53@zohomail.com
I'm married. But, I have nice Daddy friends who enjoy my services. I do enjoy corresponding with Men who appreciate us along with other like-minded "demigirls". You'll find me very responsive, caring, and friendly. I love swapping photos and stories and enjoy writing about my adventures, thoughts, feelings and fantasies.
Please be safe!
Love,
Tricia/Timi