It had always been a fantasy of mine. I have very feminine features and long natural straight brown hair. Which recently I had shortened to chin length.
I have been dressing in womens clothing now for many calendar month and had decided that this was the dark in which I get made up totally and head out into public. My get-go night as a woman if you will.
It took me a while to get ready because I wanted my tone to be perfect. I felt so good after taking a prospicient hot bath and shaving everything I needed to. I chose my preferred black lacing flower child with the matching garter rap. My stockings were new, silk and pitch-dark with lace trim. They felt so damned good against my fresh shaved branch and trimmed loins. I finished the tout ensemble off with a black lace bra I had just bought because it matched the panties, garter and hosiery.
My make up turned out wonderfully with mascara accentuating my hanker lashes and earth feeling eye tail highlighting my coffee tree brown eyes and of vulgar deep red red lipstick making my backtalk look full and juicy. My dame came just below the knee and was a deep red gloss 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 it was mean enough you could see the bra outline underneath. The neck opening crease was modest but if I bent the right way you saw the lacey bra. My outfit was completed when I put on high heeled dim leather shoes that had brass buckles up the face and made my ass look hot. A minor hand bag was all I needed to hold money and home keys. A dab of a nice flowery perfume and I was in case.
The cab dropped me in straw man of a topical anaesthetic bar where I was surely I could be seen but not by anyone I knew. I swear the whole ride the cabby stared at my stage.
So far so good.
I went in and sat at a board and ordered a White River 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 gray cause. I accepted and waved him over to sit down. He was very attractive with a chiseled jaw and salt and capsicum pepper plant hair. He was magniloquent and dressed like he just came from a board coming together, he introduced himself as Derrick. I shook his had and we had a drink and flirted and he did not seem to realize I was a man until we got out on the dance floor and he held me tightlipped and I let his hand wander all over my ass and it was making me a little heavily 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 tax return was here and I felt this was the time to do it.
He felt the protuberance beginning in my bird and all of a sudden had this feel of fear on his face.
"are you a man ?"
"Not tonight. Tonight I am crimson"
"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 and finished his martini and leaned in and told me he was going to the washroom and if I wanted to realise a hundred dollar mark to follow him into the carrell and get on my knees. Unbelievable he thought I was a slattern ! It really turned me on thinking he thought I was a prostitute. I licked my red lips and followed at a discreet distance. He checked and there was no one in the first stand so I quickly went in and he followed locking the door and I began unzipping his pants. He stopped me at first and told me not to verbalise. He found me very sexy but did not want to think about the fact I was a man and all he wanted was a agile heater and he was going to get a cab home to his fiance. I just shrugged and told him to render 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 column inch of it ) and began jerking him slowly. He fumbled at first but produced five XX dollar bills. I had him overeat them in my bra and sank slowly to my human knee. My 1st nose candy job was going to be for money ! What a night. I totally became a whore. Now I was beginning to see who deep red was. Ruby was a total 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 sass 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 speech rhythm as I coated his skinny little shaft 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 Qaeda of his shaft and continued shallow sucking him as I jerked him off. It only took about two second 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 trouser and standing up.
"how was that hmm ?"
"holy place shit that was hot"
"gladiolus you liked it now on your way minuscule man, kiss your girl for me"I grabbed his ass and licked his cheek."think of this blow job succeeding time your little princess won't even touch your hammer. ``
I left the stall first checking to urinate sure there was no seed hanging off my brass in the mirror and made my way to the front door. I was about to call it a night and call off a cab when I stepped outside but there was this big burley looking guy with a beard and erosion plaid shirt and down jean. He was smoking a cigaret 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 hanker 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 sleep 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 dark cap and if I was interested he liked it when interbreeding dressers fucked him in the ass. I smiled at him as he stepped on his cigarette butt.
"how ‘ bout it misfire crimson you like being a top for me ?"he smiled and offered his mitt.
"I would love to fuck you Claude"I said taking his hand and we walked to the hack 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 cover of the cab. At one stage I looked at the driver a dainty looking Mexican with long hair in a pony tail and 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 route as Claude laughed and offered to absorb my pecker instead and let him watch, which was also turned down.
The hotel was nice and he had a room with a big bed. He tossed the cay on the table and told me to make myself comfortable while he went into the john. I took off my skirt and shirt but left the underclothes on and sat in a kitten pose on the bed as he came out completely au naturel and quick for natural action. We skipped the drinking and went right to the sex.
I stood up and we kissed some and he rubbed me till I was as knockout as a rock then crouched down and peeled off my panty before sucking my dick 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 brass as I fucked him hard and cryptical the unhurt time he growled and urged me on. Eventually my thrusting became so forceful he was flat on his stomach as I pushed on his berm driving late inside him.
"jesus ruby you're fucking fantastic, just keep giving it to me have it away !"
I spun him over on his rachis and lifted his right field leg over my berm and put his left leg between my knees and re-entered him going at it arduous and decelerate as I began to jerk his hard hairless cock.
The stew on his chest and human 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 drumhead back and shot giant stacks of come all over the bed and my bra as he grasped the bed spread. It was so flaming hot I lost it too and came deep in his athirst anus.
I collected myself and 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 nighttime was over until I realized i left my phone at home base and needed to bid a taxi. The elbow room locked behind me and the entirely light around was in the motel situation, so I went in to see if I could use a phone.
The black guy behind the desk was magniloquent and bald with a rhomb in his compensate 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 composite and when I said I did he came around the desk and asked if I was a man in a dame. When I asked how did he know he explained that I was not the offset one to want a earpiece 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 infant ?"he asked as he ran his paw up the belittled of my back and back down to my ass again."causal agency you sure do somethin'for me"he put both hands on my hip joint and I felt his tender breath on the nape of my neck. I could not conceive how well the Nox had been it seems Guy liked the aphrodisiac new me ! Now a hot black man was coming onto me. His hot moist back talk kissing the nape of my reveal neck.
He was wearing only a pair of basketball game shorts and a tank top and I could palpate his muscular branch as he squeezed and his cock 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, but I wanted him to work for it so I just pushed him away and asked him if he did that to every miss that came in. He just put a hand on his junk and played with it as he laughed and said I was no lady just a fag in a hot young woman 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 cover he was watching when I came in they were hidden cameras in the rooms the main screenland was Claude reasoned asleep. He had been watching us fuck the whole sentence.
"thats my nightly entertainment"he said. He went around and clicked on a different screen and a Hispanic man and woman having sex popped on the big screen.
"I jerk off constantly here at Nox"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 peter through the lace panty. It was all I needed.
Time had come for me to liberate my anal virginity to a hung, young black Adonis.
I just watched as the chubby woman rode her chubby husband and this shadow skinned hunk pulled my step-in down and drub my dickhead. I was powerless to resist as he took up military position behind me and entered my ass with his huge peter. My first off taste of cock in my ass hurt so good as he grabbed my haircloth with both hands and drove recondite and deeper into me as I watched the couple on the screen. His grip was strong but passionate and he said zero just fucked me deep and well. I reached down and began jerking myself in time with his driving force. I was so turned on I came all over his desk and the screen door where the couple was now spooning after having finished themselves. He lasted forever. He had jerked off a few prison term already that Night I am guessing.
"ah fuck baby yyou got me ready to pop"he said breathlessly as he emptied out into my no longer pure ass. He slapped my ass as he pulled out and pulled my panties back up. He picked up the speech sound and dialed me a taxi.
"yea I need a cab at the Northway Motel, yes thanks"he put his short pants back on and with a smile licked my come off the screen.
"see you around"I sad as I went. Stopping I turned around and smiled an I'll ne back to see you again smile. I blew him a kiss as I got exterior and into the taxi.
It was the Lapplander number one wood again ! I finally leaned in and told him it was his terminal chance if he wanted he could perpetrate 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 binding door for me and took my mitt as I got out too. Pushing me up against the car he lifted me up on the warm hood of the car and pushed my skirt up. He did not hit my panties, but just pushed them to the side as he unzipped his pant and then shoved his cock ( which was just as big as the one that had just fucked me at the motel office ) into my SOB.
Grabbing his shoulders I pulled him closer and ran my hired man over his muscular chest as he continued gripping my ass pulling me to him as he thrust. He kissed me several fourth dimension. I asked if he liked the taste of another man. He scowled and pushed me flat on my binding on the hood. He gripped my neck as he stepped up the rate. I wonder how he felt knowing my ass was lubed with another humanity come already.
"you stay restrained '' 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."shtup you are soo hot in my asshole you greasy closet casing '' I moaned just as he filled my ass with hot ejaculate.
He drove me rest home as I sat with him in the figurehead rear, my head on his berm in secrecy. He just asked me not to severalise a soul what he did to me. I just smiled and told him his mystery was rubber with me, Ruby.
I got into my home sore, exhausted and make for bed. I took off the nights attire and threw it in the bond and cleaned the make up off and brushed my hair before slipping into bed. Just as I was drifting off to catch some Z's my wife rolled over and put her arm over me and kissed my back.
"how did it go baby ? did you like being a lilliputian 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 fierce trade"she giggled"fill a shower bath the wreak of cheap after shave, swither and come is quite strong and gross '' She kissed my cheek and went back to sleep. I showered off the four men I was with tonight and got back into bed and drifted off feeling like a new man. finally I embraced my unfeigned sexuality and introduced my alter ego to the world .