Transition From Man to Lady

I was born male, but both physically and emotionally I was more female. I went out of my way to - just barely - avoid being regarded as a sissy by my peers growing up. But after I hit puberty I never really developed the physical characteristics associated with manliness. By age 18 I had reached my full height of 5',6", and was small boned and delicately built. My jaw, for example, remained small and heart shaped, and I developed breasts. I first experimented with cross dressing at that time. Then, the worst thing I could imagine was being a "queer." I masturbated constantly, but assured myself that I must be straight because I was so turned on by the gorgeous naked women in the magazines I used as visual aids. Of course now I realize that I was actually Identifying with these women.

One afternoon, when I was 18 and my mom was at work, I wandered into her room and began rummaging through her dresser - her underwear drawer in particular. She had an array of lacy and string bikini panties. Impulsively - I was naked and was beating off - I put on a pair of black string panties. Almost without thinking, like I was being guided by an invisible hand, I applied some of her red lipstick to my pouty lips, and looked in the mirror. I was shocked; instead of seeing the plain little boy I was used to seeing, there was a sexy looking woman! A thrill ran through my entire body as I slipped into a pair of her high heeled pumps, and I walked to the full length mirror to view myself. I ran my fingers through my thick blonde hair, teasing it up, and what I saw made me shoot a load all over the mirror.

From that day on I was hooked. I would wear her lacy silky underwear, shoes and lipstick all the time she was at work, and jerk off several times. And I never had a learning curve walking in heels; I was a natural, and never stumbled or had my ankles turn in. Thing is, the minute I'd shoot my load, I'd be disgusted with myself, and make excuses why I had done what I had done.

During high school I never had a girlfriend. I was extremely shy around girls, none of whom ever really showed an interest in me anyway, due to my plain boyish appearance. I met my wife online through an Asian dating site. Her name was Emi and she was really gorgeous, a real girlie-girl. I knew I could never get a wife like that in America, but girls from the Philippines wanted to come to the U.S. and would pretty much marry anyone to do it. After a year I was able to bring Emi to the U.S. and we were married.

It was Emi who cherried me. She on the other hand had led a very active sex life from the time she was young. She was surprised that I was nervous and actually reluctant to have sex with her, and gave me a really strange look. She began talking about living as brother and sister. But after our first fuck, all that went away. Soon we were fucking all the time. I was 23, and she was 20. But my problem was, every time we fucked, I was fantasizing about being a woman in bed with a man!

Within a few months my true nature began to leak out and Emilynne began questioning me about my sexuality. At first I feigned outrage, but when we were in bed, having sex, I grew weak, and began confessing bit by bit, some of my fantasies. Emi was supportive and didn't judge me, but she began dressing in revealing clothing and openly flirting with guys when we went out. At first I was angry, but then began urging her to be sexy and tell me about the things guys said to her. If she mentioned a particular guy, I'd probe her about what it was she liked about him - that sort of stuff. When I got laid off from my job, Emi expressed interest in getting a job. She had been a dancer in the Philippines, and one day, when I was looking through the Help Wanted section, I saw a club that was hiring "waitresses." I began getting hard, thinking about Emi doing that. I showed her the ad and she called them. They told her that it was a bikini bar and to be sure and wear high heels to the "audition," as they put it.

The place was called the "Ace of Spades, and they gave her the address and an appointment for 2 p.m. that day. After she left I beat off to internet porn until she called. She had been hired and they wanted her to start immediately. Long story short, the job was less about waitressing and more about hostessing. The girls were expected to entertain the clientele - sit with them drink with them, encourage them to buy drinks, etc. And after the midnight the place became members only, and I found out that the girls danced nude on the bar, and took men into the bathroom for private sex. It was a whore house. Emi was totally unashamed by this and began bringing home more money than I had ever had in my life. I stopped looking for work, and spent my days masturbating to porn online.

The fact that the Ace of Spades was a black club got me interested in interracial porn, and I soon began fantasizing about being a woman again. I went to Walmart and bought a pair of high heels - red and black 6 inch pumps - and some red lipstick and green eyeshadow. One really scorching July afternoon, around 4 p.m. I decided to go to an adult bookstore to check it out. The route to the adult bookstore took me right past the Ace of Spades. As I drove past I saw a group of gangsta looking black guys out front. when the door opened I heard the loud blast of rap/Hip hop music, and I got a hard on just knowing my wife was inside. I watched as a petite white girl with a shaved head made her way inside. She was wearing a halter top and jeans, and the black guys were howling as she went inside.

The adult bookstore was about half a mile down the street from the Ace of Spades. I bought 5 bucks worth of coupons and went into the arcade in the back of the store. It was very dark, lit only by red dim bulbs, and it was a long corridor lined with private video booths. as the corridor went on, you could either go left or right. There were a couple of men hanging around in the dark corners, smoking cigarettes, despite the No Smoking signs. I got a booth and went in, locking the door behind me. I was wearing flip flops, shorts and a tank top. When I masturbate I always do it nude. So I quickly undressed and began watching some interracial porn. After a while something caught my eye; it was a hard cock sticking through a hole that had been cut out in the wall of the booth. I didn't hesitate, I knelt on the floor and began sucking that cock. I heard a groan and felt the hot splash of liquid and the taste of fresh semen. It was so weird and strange, but I swallowed it all. I got back on the bench - I was so HOT after sucking that cock - that I jerked off and shot cum all over the place! Once I came I was so embarrassed and ashamed! I quickly dressed, ignoring that another cock was sticking through the hole, and almost ran out of the store. I got outside and the bright sunlight and stifling temperatures hit me. I drove home, past the Ace of Spades, my head reeling with conflicting emotion. I had sucked a fuckin' COCK! what the fuck was WRONG with me??

When I got home I couldn't stop thinking about what I had done; I was a queer - a faggot. I was so disgusted with myself. But then I found myself in bed, my laptop showing porn - a sexy white girl taking care of a hot black man - and I had a hard on again. I jerked off for about 15 minutes and I realized that I was going back to the adult arcade. I hurriedly dressed and within a half hour, I found myself naked in the same booth, this time prepared and desiring for what was to happen. By now it was almost 6 pm and there were a lot more men in the arcade. This place was located in a very seedy, ghetto part of the city, and there were a lot of blacks there. I heard a noise and looked at the hole. I could see someone looking at me. I pretended not to notice, but seconds later the doorknob on my booth wiggled, followed by a knock. I reached over and unlocked the door. It cracked and I saw an older black man wearing a suit looking at me. I was nervous and just kept watching the porn.

He stepped in, closing and locking the door behind him. I was sitting on the bench, completely nude as he stood in front of me, massaging the lump in his pants. I reached over with my small hand and squeezed his bulge. I unzipped his pants and reached in and pulled his hard on out. I got down on my knees and tasted it, then put it all in my mouth. He unbuckled his pants, allowing them to drop to the floor. He was wearing boxer shorts, and I pulled them down and began giving him a hot slobby knob job, feeling up his iron hard thighs, lowering my head to suck on his balls. As he got more horny he got a little rough and took my ears in his hands and began fucking my head violently. Suddenly his legs began to tremble and he shouted out, emptying his load into my mouth - LOTS of cum! I had to struggle to swallow it all! He pulled up his pants and quickly walked out of the booth without so much as a word. I stayed until past midnight, sucking so many cocks. I had a couple of men who were trying to fuck me, but I was afraid of that, so it would have to wait.

The next week I bought a tube of Anal-Eze, which is a lube with a topical anesthesia in it. I was determined to get fucked in the ass! Believe it or not, my first fuck was a black guy with dreadlocks - and a 10 inch COCK! As I was blowing him I asked him if he wanted to fuck me. He said he only wanted a blow job, but I was persistent, and I kept begging him to do it. He told me he'd do it, but once he began he wouldn't stop. He said I had better be sure. I was scared, but I promised him I'd take it all until he came. He had me lay back on the bench and he raised my skinny legs up over his buff shoulders and I felt his dick at my ass hole. He had me pinned down with his weight, so I couldn't really move, and he began pushing it in. I began to panic, and tried to move but I couldn't, and I cried as it broke into my cherry anus and slid into me. Because of the Anal-Eze, the initial entrance wasn't too painful, and once it was in it began to feel divine! He fucked me for a minute then came into my asshole. I was in heaven. Now I was no longer afraid to do anything! I began to spend all of my nights in the arcade, and while I was giving blowjobs and getting fucked, about a half a mile away, so was my pretty little Filipina wife! And that's how my life as an adult bookstore sissy began. In a matter of weeks I began wearing high heels and lipstick.