This is a true story about one of my experiences. As usual I changed people's names for their own privacy. I know it starts out a bit slow, but just wait and see. XXXOOO Alissa.
It was the late 90's and I was living in the East Bay area of Northern California in a medium sized city called San Leandro. I was in probably the best shape of my life, which ironically was due to my lack of money at the time. Although I had a full time job I didn't make very much per hour so I was forced to eat quite sensibly and I ran almost everywhere because I didn't own a car. This wasn't really a problem since my place of employment was a local gym.
I should start by telling you that I actually did quite good with the ladies. In fact I had more female bedroom guests than all three of my roomate's combined, except of course for the one roomate who had a live-in girlfriend. If you were to see me on the street you see an attractive, in-shape, heterosexual male. The purpose of this story is to tell you that looks can be deceiving.
The gym was also an excellent cover story for why I shaved my body on a daily basis. Many of the other employees and members would shave or wax their bodies in order to show off the muscular definition they worked so hard to achieve. As for me I wasn't what you would call heavily muscled, but I was in pretty good shape. I was moderately tall , (5'11"), and about 180 pounds. I had a nice sleek physique with flat defined abs, nice muscular legs and a bubble butt from my hours of running. Combine this with my completely smooth body and you had a recipe for some very kinky playtime.
I suppose this is as good a time as any to mention that I was also an avid lifelong crossdresser. I started at a young age trying on my moms clothes and lingerie. I suppose the fact that she was a biker chick and had plentry of trashy outfits was quite a bonus in this area. I even used to dabble in playing with her collection of sex toys, but that is a different story for another day.
Every so often throughout my life I would get the uncontrollable, (literally once the idea got in my head it was all encompassing), urge to dress up in sexy women's clothes for sexual gratification. As I got older my fantasies when dressed would steer more and more to the idea of getting fucked by another man. Soon enough it was the only thing I could think about when I was dressed enfemme. My intent in chronicling this story is to tell you about one of these events, (one of many), and hopefully provide you with some sexy reading.
Anyways back to my story. I definitely wasn't what you would call passable, but when I was done up in full make up, wig and my sluttiest outfit I was definitely hot. Don't get me wrong, I didn't just look like a guy wearing a dress either....lol.
Fortunately for me San Leandro was a lower middle class city with lots of Hispanic and black citizens. The local women's clothing stores catered to this demographic by selling lots of tight pants, short skirts, slutty shoes and skimpy lingerie at a reasonable price.
When I had a little money and the urge overtook me I would wander into these stores in guy mode and shop for the trashiest outfits I could find. When I say "urge" it was actually much closer to a compulsion. If any of you have ever crossdressed then you probably know what I'm talking about.
My heart raced in my chest and I got an incredible thrill from wandering through a womans clothing store, looking through the racks of delicious feminine clothing. I knew it was obvious I was alone and I enjoyed the stares of the sales girls as I held skimpy outfits up to my torso to judge if they would fit me.
I would even wander in to PAYLESS shoes and try on the latest women's shoes. It was an incredible thrill putting on a pair of sexy high heels or knee high womans boots dressed entirely as a man. My cock would be hard as a rock and leaking precum as I stood in the aisle wondering if someone was going to walk around the corner and see me.
Of course the biggest thrill came when I actually brought my purchases up to the register to pay. The sales girls had mixed reactions. Some would shake their heads in disgust, some would smile uncomfortably and some.....would grin knowingly. Either way it made my blood pound in my veins and my cock harder than spring steel to know that they knew these slutty clothes were for me.
I would dress as often as I could which was 2-3 times a week as I had roomates. Once dressed I would cruise the YAHOO chartrooms for local men. At that time YAHOO allowed user created chartrooms and it was actually quite easy to find a local chat partner. Most often we would cyber which always ended with my Cummings into the palm of my hand and coating my freshly painted fingernails.
Other times I would chat hoping to find a local guy willing to host for some in-person play time. It was one of these times that I started chatting with Michael. He was very sweet as we chatted and quite honest about himself. He told me that he was 30 years old, ( I was 27 at the time), he was black, and he was on parole for drug sales. Being a white guy who had never touched more than a little weed as a kid that honestly kind of scared me.
Michael and I, (Alissa my female name), chatted on-line for about a week straight. I admitted to him that I was a bit scared to meet up with a black thug when I would be so obviously vulnerable, (being a boy dressed up in slutty female clothing), and unable to defend myself if things were to turn out bad. Michael was very reassuring and genuinely nice. He told me that he had never been with a guy before but really wanted to meet me after seeing the pictures that I emailed to him. Michael told me that although he was straight and did not consider me to be female, he wanted to know what it was like to feminize a white boy for his pleasure. Little did he know that that was exactly what I was interested in too.
For many CD's, TV's, TS's it's all about becoming female in the eyes of their lovers, even if it's just for a short time. For me it was never about that. I never considered myself to be female, although I did my best to look and act feminine. For me the thrill was highest when my lover and I both acknowledged my masculinity, then did our best to destroy it. In other words I loved being a boy, dressed like a sexy slut who willingly gave up their manhood to another stronger, more dominant man.
After a week of reassurances and dirty chat with Michael I finally agreed to meet him. I have to admit the pictures of his large black cock he sent me had me more than a little excited and nervous.
The day arrived and I thanked my lucky stars for two things, 1) my roomates weren't home and 2) one of them lent my their car for the day. Going out in public dressed enfemme was always a special thrill for me. I truly enjoyed the looks of shock, disgust and sometimes even lust that I received. As I stated before, I knew I didn't pass 100%, but I did look deliciously androgynous and I would say my body was very sexy. My goal was never really to pass for a female, but rather to pass for an attractive guy who was was wearing womens clothes, a wig and make up and trying to look hot. I looked, for lack of better words, like a hot crossdresser on the prowl for cock.
I started my transformation the same way as many of my peers, with a nice long soak in a hot bath. I took my time shaving my body, bring careful not to leave any stray hairs or knick myself. Once I was done I used some of my roomate's girlfriends lotions which left me feeling smooth, and smelling sexy. Next came a liberal amount of deep red nail polish on my toenails and my mid-length press on nails.
Next I took the time to douche myself. I wasn't sure if things would go that far, but if they did I was determined to be clean down there for Michael. I really didn't need to worry because I had barely eaten in the last 24 hours anyways. I do have to admit that having the douche stem up my bum felt sexy as he'll though...lol. Once my boy-pussy sparkling clean it was time to start getting dressed.
Earlier I mentioned my roomate's girlfriend, (I'll call her Allison). She was a very attractive girl of 23 years old. She worked in women's clothing retail, (no I never shopped at her store...lol), and always had very sexy clothes in her closet. I decided that there was a bit of an added thrill that came from the idea of wearing a real woman's clothing when I stepped out to meet a male lover. So after some consideration I picked a pair of skintight low-rise jeans from her closet.
First I slipped into my powder blue Lycra thong panties, taking the time to tuck my cock back perfectly. It was no small feat because believe it or not I have a pretty nice package, 7 1/2 inches long, circumcised and thick. Once I was sufficiently tucked away I slithered into Allison's skin tight jeans. Lucky for me she had a nice big butt and the jeans were stretch fit. With a little hopping around my legs and ass were encased in the dark colored jeans and the waist came to exactly the level of my hips. I knew that if I bent aggressively at the waist my whale tail would be showing...yum! I took a look at my ass in the full length mirror and noticed how big and round it looked. I smiled to myself because i knew it was exactly the kind of ass a black man would drool over.
Next I put on my matching powder blue Lycra bra and filled the cups with my c-cup false breast inserts. Once they were adjusted and hanging naturally I put on my semi-see through long sleeve top. The hem of the shirt came to just above my navel and was an excellent addition to the low cut jeans. I completed the outfit with my black knee-high zip up boots with a three inch stiletto heel, and my black pleather jacket with a hem matching my pink shirt.
Next I sat down in front of the mirror to apply my make up. Rather than use my own supplies I decided to take advantage of my roomate's absence and use Allison's MAC makeup. I took my time, making sure to apply liberal amounts of eyeliner, eyeshadow, blush and bright red lipstick. Once I was done putting on my face I put on my shoulder length chestnut real-hair wig and bobby pinned it in place. The wig cost a small fortune but was worth every penny because of the realism it added.
I was ready....and I was actually short of breath from excitement, mixed with fear and adrenaline. Was I really going to do this? This guy could be dangerous, besides I had never even considered hooking up with a black guy before. I poured myself a tall glass of white wine to calm my nerves and took a moment to check myself out while I sipped my vino. What I saw made my already semi-erect cock strain to free itself from my panties.
I looked amazing! My makeup was flawless. My lips shined with damp desire, my eyes were dark and mysterious surrounded by the lines of black liner and dark shaded shadow. As I sat applying it I tried my best to mimic the sexy style of the Latinas I saw every day at the gym and I was delighted to see that I nailed it.
My ass and legs looked to die for, Allison's jeans showed the thick muscularity of my thighs, made my calves taper seductively down into the top of my black boots while forming a perfect frame for my already plump ass cheeks. I also noticed that the cut of the jeans made my cock virtually invisible, leaving a sexy cleft between my thighs right where they met at my crotch.
I involuntarily grinned at myself in the mirror noting with delight the natural seductive femininity oozing from my features. Any hesitation I had been feeling vanished immediately. I grabbed the car keys, threw a tube of lip stick and a few condoms into my purse and headed out the door, not caring if any of the neighbors saw me.
As I started the car and put it in gear I could feel my hands shaking and my head swimming. I was still scared, more scared in fact but the fear made my desire all the stronger. I loved the feelings I was experiencing as I drove to our agreed upon meeting place, (a 7-Elleven parking lot), a short distance away.
I arrived quickly and parked in front of the store to wait for Michael. I was feeling extremely sexy and confident for some reason so I decided to go in to the store to buy a drink while I waited. Truthfully I wasn't sure if Michael would actually show up, (people flaking on you is a big part of this lifestyle), and I was hoping I might get some inviting looks from some of the customers. I paid for my drink after making eye contact with a few guys and walked back out of the store, watching the guys watch me go in a mirror posted near the door.
As I opened the door to my car I heard a deep baritone voice call out "Alissa?" from across the parking lot. As I looked in the direction of the voice I saw an older model Buick with a large muscular black man sitting behind the steering wheel. He had black dreadlocks that cascaded down to just above his shoulders and tattoos were visible covering both big muscular arms. My heart immediately began pounding in my chest! This guy looked scary and I think I made a really big mistake I thought to myself.