My First Adventure In Drag

It had always been a fantasy of mine. I have very feminine features and long natural straight brown hair–which I recently had shortened to chin length.
I have been dressing in women’s clothing now for many months and had decided that this was the night to get made up totally and head out into public.
It took me a while to get ready because I wanted my look to be perfect.
I chose my favorite black lace hipsters with the matching garter belt. My stockings were new, silk, and black with lace trim. They felt so good against my freshly shaved legs and trimmed pubes.
I finished the underwear off with a black lace bra I had just bought because it matched the panties, garter, and hose. I felt so good after taking a long hot bath and shaving everything I needed to. My make up turned out wonderfully–with mascara accentuating my long lashes and earth tone eye shadow highlighting my coffee brown eyes, and of course ruby red lipstick making my lips look full and juicy. My skirt came just below the knee and was a deep red color–made more red by the black stockings–and hugged my little ass nicely. I put on a silk top that was two tones of blue and was tight enough you could see the bra outline underneath. The neck line was modest but if I bent the right way you saw the lacy bra. My outfit was completed by high heeled black leather shoes that had brass buckles up the sides and made my ass look hot. A small hand bag was all I needed to hold money and house keys. A dab of a nice flowery perfume and I was in character.
The cab dropped me in front of a local bar where I was sure I could be seen, but not by anyone I knew. I swear the whole ride the cabby stared at my legs.
So far so good.
I went in and sat at a table, ordered a white wine, and watched the people float around the bar. As I finished my first glass the waitress brought over another and said it was from the man at the bar in the grey suit. I accepted and waved him over to sit down. He was very attractive with a chiseled jaw and salt and pepper hair. He was tall and dressed like he just came from a board meeting; he introduced himself as Derrick. I shook his had and we had a drink and flirted; he did not seem to realize I was a man until we got out on the dance floor and he held me close and I let his hand wander all over my ass. It was making me a little hard knowing this man wanted to have sex with me. Although I had been fantasizing about having sex with another man I had not followed through yet, but the point of no return was here and I felt this was the time to do it.
He felt the bulge beginning in my skirt and all of a sudden had this look of fear on his face.
“Are you a man?”
“Not tonight. Tonight I am Ruby.”
“You are a freak.”
“If you say so, but I would still suck your cock in the bathroom if you wanted.” I walked him back to the table and we ordered another drink round. He sat quietly for a few minutes, finished his martini, and leaned in to tell me he was going to the washroom and if I wanted to earn a hundred dollars to follow him into the stall and get on my knees. I licked my red lips and followed at a discreet distance. He checked and there was no one in the first stall so I quickly went in and he followed, locking the door. I began unzipping his pants. He stopped me at first and told me not to speak. He found me very sexy but did not want to think about the fact I was a man; all he wanted was a quick hummer and he was going to get a cab home to his fiance. I just shrugged and told him to show me the money. If I was going to do this for money, I wanted to see the money first. He reached into his inner pocket as I took his cock out (all four inches of it) and began jerking him slowly. He fumbled at first but produced five twenty dollar bills. I had him stuff them in my bra and sank slowly to my knees. My first blow job was going to be for money! What a night; I totally became a whore.
I licked all down his shaft and sucked his balls a little but I could tell he just wanted me to blow him so I took all of him in my mouth and as his balls tapped my chin I sucked him hard and slow. He soon has his hands on my head and was guiding my rhythm as I coated his skinny little dick with my spit, so much in fact it dribbled out of my mouth and left little strings on the end of him when I came out for air. I grabbed the base of his shaft and continued shallow sucking him as I jerked him off. It only took about two minutes to make him come in my mouth. He twitched as I drained his cock of come and licked him clean before tucking him back into his trousers and standing up.
“How was that, hmm?”
“Holy shit, that was hot.”
“Glad you liked it. Now on your way little man, kiss your girl for me.”
I left the stall, first checking to make sure there was no semen hanging off my face in the mirror and made my way to the front door. I was about to call it a night and call a cab when I stepped outside, but there was this big burly looking guy with a beard and wearing plaid shirt and blue jeans. He was smoking a cigarette by the parked cars and called out to me.
He introduced himself as Claude but I suspect that was made up. I told him my name was Ruby. He laughed and told me that he knew I was a guy. I just smiled and assured him I was anything he wanted me to be.
He smiled as I took his cigarette and took a long drag and handed it back exhaling slowly. I smiled at him and he looked me up and down before telling me he thought I was dead sexy and wanted to know what the rest of my evening held. I simply told him that I was up for anything. He was staying at a motel for a while as his wife had kicked him out because he was sleeping around with trannies. He invited me back to his hotel for a night cap and if I was interested; he liked it when cross dressers fucked him in the ass. I smiled at him as he stepped on his cigarette butt.
“How ‘bout it Miss Ruby? You like being a top for me?” he smiled and offered his hand.
“I would love to fuck you, Claude,” I said taking his hand and we walked to the taxi stand.
As luck would have it, I got the same cabby that dropped me at the bar. All the way to the hotel he watched as Claude and I made out and fondled each other in the back of the cab. At one point I looked at the driver–a nice looking Mexican with long hair in a pony tail, strong shoulders, and kind eyes–and told him if he wanted to give us free ride to pull over and I would blow him. He just blushed and turned back to watching the road as Claude laughed and offered to suck my cock instead but let him watch, which was also turned down.
The hotel was nice and he had a room with a big bed. He tossed the keys on the table and told me to make myself comfortable while he went into the bathroom. I took off my skirt and shirt but left the underwear on and sat in a kitten pose on the bed as he came out completely naked and ready for action. We skipped the drink and went right to the sex.
I stood up and we kissed some; he rubbed me till I was as hard as a rock then crouched down and peeled off my panties before sucking my cock to its full eight inches. He moved to the end of the bed and got onto all fours.
“I believe you know what I want,” he said as he wiggled his ass in the air.
I stepped up behind him and quickly drove my cock into his gaping ass. He groaned in delight as I began pumping deep into his well plowed ass. I grabbed his ass cheeks as I fucked him hard and deep; the whole time he growled and urged me on. Eventually my thrusting became so forceful he was flat on his stomach as I pushed on his shoulders driving deep inside him.
“Jesus Ruby! You’re fucking fantastic, just keep giving it to me… fuck!”
I spun him over on his back and lifted his right leg over my shoulder and put his left leg between my knees and re-entered him, going at it hard and slow as I began to jerk his hard hairless cock.
The sweat on his chest and face told me he was totally about to loose it.
“C’mon stud, come for me. Shoot all over the place,” I commanded. “Don’t I turn you on, hunh?”
He, as if on cue, threw his head back and shot giant loads of come all over the bed and my bra as he grasped the bed spread. It was so fucking hot I lost it too and came deep in his hungry anus.
I collected myself, cleaned up a bit, and got dressed again; by this time it was midnight and Claude was passed out naked on his bed. I left quietly and thought my night was over until I realized I left my phone at home and needed to call a taxi. The room locked behind me and the only light around was in the motel office, so I went in to see if I could use a phone.
The black guy behind the desk was tall and bald with a diamond in his right ear. He smiled knowingly at me as I entered the room and he asked what I needed. He was not worried about me seeing him checking me out as I walked to the desk. He asked me if I came from the room at the end of the complex and when I said I did he came around the desk and asked if I was a man in a skirt. When I said how did you know, he explained that I was not the first one to need a phone after a quickie with Claude. He then said I was by far the most attractive and put his hand on my ass.
“You like dark meat baby?” he asked as he ran his hand up the small of my back and back down to my ass again. “Cause you sure do somethin’ for me.” He put both hands on my hips and I felt his warm breath on the nape of my neck. I could not believe how well the night had been; it seems guys liked the sexy new me! Now a hot black man was coming onto me.
He was wearing only a pair of basketball shorts and a tank top, I could feel his muscular arms as he squeezed and his dick pressing on my ass as he freely ran his hands over my tummy and down my crotch. I suppose his aggressive approach should have scared me away but it was turning me on. I wanted him to work for it, though, so I just pushed him away and asked him if he did that to every girl that came in. He just put a hand on his junk and played with it. Laughing, he said I was no lady just a fag in a hot girl disguise and I should be flattered a guy like him was interested.
His cock was tenting the shorts nicely and I got a look at the screen he was watching when I came in, they were hidden cameras in the rooms; the main screen was Claude sound asleep. He had been watching us fuck the whole time.
“That’s my nightly entertainment,” he said. He went around and clicked on a different screen until a Hispanic man and woman having sex popped on the big screen.
“I jerk off constantly here at night,” he bragged as he took off his shorts. He attempted to bend me over the desk and pushed the skirt up as he rubbed my dick through the lace panties. It was all I needed. Time to loose my anal virginity to a hung, young black Adonis.
I just watched as the chubby woman rode her chubby husband while this dark skinned hunk pulled my panties down and licked my asshole. I was powerless to resist as he took up position behind me and entered my ass with his huge dick. My first taste of cock in my ass hurt so good as he grabbed my hair with both hands and drove deeper and deeper into me as I watched the couple on the screen. His grip was strong, but passionate, and he said nothing… just fucked me deep and well. I reached down and began jerking myself in time with his thrusts. I was so turned on I came all over his desk and the screen where the couple was now spooning after having finished themselves. He lasted forever. He had jerked off a few times already that night I am guessing.
“Ah, fuck baby. You got me ready to pop,” he said breathlessly as he emptied out into my no longer virgin ass. He slapped my ass as he pulled out and pulled my panties back up. He picked up the phone and dialed me a taxi.
“Yeah, I need a cab at the Northway Motel. Yes, thanks.” He put his shorts back on and, with a smile, licked my come off the screen.
“See you around,” I blew him a kiss as I got outside and into the taxi.
It was the same driver again! I finally leaned in and told him it was his last chance if he wanted to pull over and do what he wanted to me. He looked around as we stopped at a traffic light. He turned off the meter and pulled into a low lit parking lot and got out of the car. He opened the back door for me and took my hand as I got out too. Pushing me up against the car he lifted me up on the warm hood and pushed my skirt up. He did not remove my panties, but just pushed them to the side as he unzipped his pants and then shoved his cock into my asshole.
Grabbing his shoulders I pulled him closer and ran my hands over his muscular chest as he continued gripping my ass pulling me to him as he thrust. He kissed me several times. I asked if he liked the taste of another man. He scowled and pushed me flat on my back on the hood. He gripped my neck as he stepped up the pace.
“You stay quiet,” he barked. “I pretend you lady, not faggy man,” he gasped.
“Whatever you need to do you big cocked bastard,” I smiled. I came again soiling my pretty panties. It soaked through to the front of the dress too. “Fuck, you are so hot in my asshole, you greasy closet case,” I moaned just as he filled my ass with hot come.
He drove me home in silence. He asked me not to tell a soul what he did to me. I just smiled and told him his secret was safe with Ruby.
I got home sore, exhausted, and ready for bed. I took off the night’s attire, threw it in the hamper, cleaned the make up off, and brushed my hair before slipping into bed. Just as I was drifting off to sleep my wife rolled over and put her arm over me and kissed my back.
“How did it go baby? Did you like being a little whore tonight?” she said sleepily.
“Mhm, darling, I did. Thanks for letting me do it.”
“You are welcome. You’ll tell me all about it over breakfast.”
“Okay.”
“You must have had fun, you smell like rough trade,” she giggled and went back to sleep. I drifted off feeling like a new man. Finally I was ready to embrace my sexuality.