I am a bi crossdresser and I started dressing up like a sexy slut in my early teens. At 15 I gave my very first blow job and at 16 I got laid and was hooked from then on. For what ever reason I loved being a submissive boy-toy slut for boys! However, by the time I graduated from high school I had quite a reputation in the small Texas town I grew up in and decided it was time to move on.
I moved to Dallas and found a gig as a bookkeeper for an auto dealership but spent all my free time dressing up like a hooker and partying and sucking a lot of cock. It was fun while it lasted but I felt like it was a road to nowhere, so in an impulsive and sober moment I joined the Navy, thinking it might straighten me out and take my life in another direction, What was I thinking?!
Basic training was a total bitch! I had no free time or privacy and my urge to dress and have sex was totally suppressed. Those of you that know this compulsion know it just makes you want to do it even more! Being amongst all those good looking boys in close quarters drove me nuts with lust. I often had a difficult time keeping my cock from getting hard, especially when we hung around just in our shorts, and in the shower, forget it! The other guys gave me crap about this and called me homo all the time but I tried my best to act macho and talk about pussy at every opportunity.
A guy named Frank started being friendly with me and I certainly was attracted to him. Frank was a good looking hunk of a black dude from Maryland. He was about 6'5" tall, well built with a big chest and trim waist. We were friendly with each other but without any privacy ever, we were just friends but underneath, we both felt a sexual tension. Frank said he wasn't at all bi or gay, in fact cracked a lot of anti-gay jokes but everyone knew he was a hound dog and he talked about fucking chicks all the time.
I would lay in bed every night, exhausted by our training, but fall asleep fantasizing about being all dressed up in my make-up, high heels, hose, and mini skirt and sucking Franks big black sexy dick.
Finally, one day near the end of basic, Frank and I were told to unload a truck at the mess hall. As we were working our chatter soon became about sex and Frank said he was so fucking horny. In a way not directed at me, but in a general sense he said he needed a blow job so bad it was all he could think about. My heart was pounding when I heard him say that but I acted like I didn't hear him. He repeated it a short while later and this time I looked at him and smiled but again didn't say anything. Just a few minutes later I was at the front of the semi trailer sitting on the floor and sorting thru some boxes when I heard the trailer door close, putting Frank and I in total darkness and privacy. Without a word between us he come over to me and dropped his pants. I eagerly pulled down his shorts and put my hand around his hard cock and wrapped my lips around it. It was by far the biggest dick I ever sucked. It must have been about 10" long and very thick. Frank put his hands on the side of my head and I took my hand from his cock and let him fuck my mouth and that he did! I don't know how long it was but I was in a trance having this big strong black man fuck me like that. His huge cock head was pulsating in my mouth until he filled me with his warm musky cum. I eagerly swallowed all I could but this guy was saving it up and I swear I never saw a guy shoot so much cum for so fucking long as Frank did that day!
We heard some guys outside the truck so we had to both regain our composure quickly. Frank pulled up his pants and reopened the door and we went back to work, nobody the wiser. Later on the way back to our barracks Frank told me he really enjoyed that and I told his that I did too, immensely. I shared with him that I was actually a crossdresser and would love to dress for him sometime and do it right. He was very interested in my crossdressing and asked me a lot of questions. I told him I dress slutty and love to be the submissive slut. He said he has a real fetish for red lipstick on chicks and I told him I did too!
Thru the next two weeks of basic I managed to suck him off three or four more times, each time as exciting and pleasurable as the first.
We were happy to hear we both were to be shipped out to San Diego for schooling after a brief four day leave. I had my brother send my suitcase containing my girlie clothes to a sister CD I knew in Chicago, and Frank and I made plans to hook-up at her place.
I met Candi over the internet before I joined the Navy and we became friends quickly. She was a very hot CD living on the North side of Chicago and I stopped in to visit her on my way to basic training. She greeted me dressed and was even sexier than her pictures and we spent a nice evening together getting pretty loaded. I didn't dress that evening and we didn't have sex or anything but we had a nice time together that ended in a big wet kiss and plans to get together in the future. Candi was more that happy to have me crash with her at her place while on leave.
I got to Candi's place around 3:00 in the afternoon and she greeted me at the door in a robe and high heels and was in the middle of putting on her make-up. We had a glass of wine and talked and I told her about the crap in basic training and about Frank. I also told her Frank was visiting his sister in Milwaukee and would be here tomorrow night. Candi was excited to meet him after my vivid description of him and his monster cock.
I told Candi I was so very excited to dress-up after this loooong dry period of time and she agreed we should get right to it. Candi thought I would enjoy a night on the town and told me about a great club she goes to that welcomed transgendered, gay, as well as straight people, to which I eagerly accepted her suggestion! She got my suite case I had shipped up from Texas and it was in the spare bedroom waiting for me. I showered and shaved my face, legs, and underarms and already felt my fem side starting to emerge. I laid out my make-up on the bathroom counter and felt so wonderful putting it on. As I mentioned I love the dramatic and slutty look so lots of sexy make-up is required. I slipped into a red bra and panties and then I applied a blueish silver eyeshadow liberally to my eyelids, a darker blue in the crease, lined my eyes with a black pencil and carefully applied long false eyelashes. By now my cock was hard and poking thru the leg hole of the panties and damn, did it feel nice. As I was putting on my mascara Candi came in, having finished dressing, with a glass of wine for me. She looked stunning in a washed denim miniskirt, low cut pink blouse and denim bolero jacket. She was wearing a pair of pink strappy high heel sandals, tan stockings and a striking blonde wig. Her makee-upn was perfect.long false lashes like me, and perfectly shaped full lips with a bright magenta lipstick! Oh my gawd do you look yummy, was all I could say.
Candi complemented me on my eye make-up too and seeing my boner commented on how excited I seemed to be. I agreed that I was. Candi gave my cock a little squeeze and asked if it was OK to watch and talk as I finished. I hardily agreed so she put the seat down on the toilet and we talked as I finished my make-up. We talked about guys, sex, past lovers, sex, the club we were going to and more sex! Candi was experienced (like me) and adventuresome (like me) and loved cock, (like me), so we were pretty sure we were in for a fun couple of days.
I carefully lined my lips with a brick red pencil, exaggerating my natural outline a little and filled them in with a glossy red lipstick. Candi asked me more about Frank and it asked if maybe I would be willing to share him. I not only agreed but told her maybe Frank would be interested in a threesome with both of us. Needless to say that was an exciting possibility to both of us!
As I applied the finishing touches to my make-up, blush, several more coats of mascara Candi was gently playing with my cock, almost absentmindedly as we talked. When I finished I turned to face her and picked up my wine glass and took a sip as she slipped my cock between her warm inviting lips and softly sucked me. I knew I wouldn't last long and sure enough in just a few short minutes I came between those sexy magenta lips! Candi smiled up at me and looked at herself in the mirror and said she was proud of the fact that she can suck off a cock and not even mess up her lipstick! I offered to return the favor but she said she was good for now.
Candi went back to the kitchen to wait for me and I got dressed, feeling much more relaxed after having cum. I almost forgot how luscious it feels to slide on my stockings. Fortunately I have long shapely, girly legs that look terrific in nice stockings. I wore black hose, with 5" high heel pumps and a black, tight leather mini skirt. I felt my boner stir and though how delicious it was to be able to turn myself on so fucking much by dressing up! I also wore a red low cut sweater and a sexy blonde shoulder length wig with reddish brown streaks. A rhinestone necklace and earrings and two bracelets completed my ensemble. I put some essentials in my purse. lipstick, compact, blush, mascara about $40, and my drivers' license, headed to the kitchen to meet Candi.
Candi was as knocked out by my appearance as I was of hers and insisted we take some pictures together. She told me to pour us some more wine as she set up the camera for us. Candi put the camera on a tripod and we took several photos together. We looked very feminine and slutty and agreed we didn't think anyone would clock us as a guy in drag, that's for sure. Except maybe that very few genetic girls dress so damn sexy!
We finished our wine and Candi suggested we head out to the club and stir up some trouble. We were both a little buzzed from the wine, and absolutely intoxicated by our excitement so fortunately we didn't have far to drive. We did manage to get lots of stares from guys in cars next to us as well as a few waves and honks that made us giggle.
We got to the club around 9:30 and it wasn't very crowed yet, so we were able to get some choice seats at the bar and lots of looks from both the gay and straight crowd. As usual several guys moved closer to us. Not approaching us just yet, but circling us like a hungry pack of sharks. Candi knew several people there and introduced me to the bartender, a very sexy Latin girl named Tina. Candi told me she was transgendered, a lesbian and from Cuba. The other bartender was Tom no one knew if he was gay or not but Candi thought so. Several others came up to say hello and wanted to meet the new girl-me! I met a couple of other CD's a few gay guys and a couple (man and wife) that liked partying with CD's. A few guys said hi too, but Candi dismissed them I suppose from previous experience. We bought our first drink, but after that they were free, lol, another benefit of being a slutty gurl. We were getting pretty loaded by then having lost count of the glasses of wine we had when an attractive older CD named Tammy came over and asked if we wanted a hit of ecstasy, that we both accepted. Soon after taking the X, the music became much more sensuous and I felt a nice warm tingly buzz. I headed to the restroom to pee and freshen up to my surprise there was just one unisex bathroom! Inside were two guys making out right next to a GG fixing her lipstick while a guy was peeing at the urinal. It was kinda hot, I thought. I went into an empty stall, did my business. The two guys were still making out but the GG fixing her lipstick was gone so I took her place at the mirror and fixed my lipstick and powder. By now one of the guys next to me was on his knees with the other guys cock in his mouth. The guy getting sucked looked over at me and nonchalantly said hello. I said hello back and walked back out to my place at the bar.
When I reached the bar Candi was talking with two guys that I noticed looking over at us for quite some time. I was getting pretty hungry for cock and up till now we had no real good prospects, so I felt a little rush as I took my seat, hoping maybe... Candi introduced me to Steve and Kyle when I sat down. They were both there in Chicago on business from Kansas City. Steve was tall and good looking and Kyle was shorter, about my height (without heels) and sweet but not handsome. Steve was hitting on Candi pretty good and she was obviously enjoying it, but Kyle was a little shy so I did most of the talking. The more we talked the more I liked Kyle and besides I was pretty buzzed and really, really horny by now. As he told me about his work I was fantasizing about having his cock buried deep in my ass, so soon I was flirting and touching him as he talked. I brushed my knee against his crotch a few times and soon noticed a cute and welcome bulge in his pants. I noticed Candi whisper something in Steve's ear to which he smiled and said sure, let's go. Candi told Kyle and I they were going out for some air and would be back soon, and winked at me. (That's code for I am gong to suck this guys cock out in the car!- been there/done that. Kyle was loosening up some and he knew what Steve and Candi were up to. It was cute.first he casually rested his hand on my knee, then ever so slowly moved his hand up, eventually stroking my inner thigh at my stocking top. Little did he know that by now that I secretly wanted him the force me over the bar stool fuck my ass! Feeling his hand stroking my thigh was heavenly but poor Kyle just wouldn't make the move. Finally I remembered the bathroom situation, and in my most seductive voice asked if he would like to accompany me to the bathroom. He looked surprised but before he could answer I grabbed him hand and led him toward the bathroom. We got some knowing looks on the way and inside were 4 or 5 people either talking, or doing their business. I headed straight for an empty stall and took a seat and proceeded to undo Kyle's belt buckle and unzip his pants. He moaned softly when I took him between my red lips and I sucked his (rather small, but very hard) cock in my own special way. His breathing increased and his body twitched as he softly whispered yes, yes, to me. I sucked him a good five minutes before I felt his cock head swell and Kyle shot his cum in my mouth. He took a few seconds to catch his breath then he surprised me by kissing me, tasting his own cum (straight guys don't do that). He surprised me again by saying it was his turn now, and helping me up then taking my place on the toilet. I reached in and pulled my she-clitty out of my panties and Kyle sucked me! I rewarded his efforts with a real nice orgasm of my own, straight down his throat!
There's a lot more to tell, so stay tuned...