tagTranssexuals & CrossdressersProperty To Be Pimped

Property To Be Pimped


It had been weeks since I'd brought to light my idea of my wife, Suzie, strapping on a big dildo and taking me dressed as Desiree, the Hot to Trot Transvestite. While at first she teased me with possible participation, it never came to be, despite me bringing it up on several occasions. She really didn't care for me dressing up, jealous of my clothing expenditures mostly. I'd kept no secrets since marriage from her, including my desire for cocks when dressed as Desiree. She just couldn't seem to come to terms with the idea of me being butt fucked by a man. Best she'd done in the past was let me suck a dildo she held between her legs and fuck me with a handle of a hairbrush but that was so long ago, before marriage even, that this little sissy was very cock hungry.

I was quite surprised when she came home all excited last week announcing our friend Carrie was engaged to get married to a hairdresser in Buckhead. The best part was to be her engagement / wedding shower party. Not to be the normal all girl event, it seemed, as Carrie planned to have a dress up party for both men and women. Carrie always was a free spirited girl and one I'd longed for secretly over the years. Drop dead gorgeous and always the flirt, she had really enticed me at my own wedding when she arrived in the sexiest backless red silk mini. God, the dress and her body confused me so; I didn't know whether I wanted the dress or her out of the dress.

Carrie was one of Suzie's girlfriends that she'd shared my little cross-dressing secret with and I always loved it when Carrie would call and ask what I was wearing. My mind would always wander to lustful places when she teased me, just as it did now when Suzie said we'd be going as guy and gal, except she would be the guy.

I was beyond happy to hear of her plans. Suzie would dress up as a pimp in a zoot suit and me as her classy little whore.

Readily agreeing, I anxiously awaited the next Saturday and spent most of my free time shopping for the perfect outfit. I'm sure Suzie did the same.

By Saturday morning, I'd found exactly what I was looking for at Cache, a upscale boutique catering to the classiest of ladies. The sales lady was quite helpful and did not blink an eye when I told her of our plans and described the red dress I was hoping to find. Luckily, they had an almost identical dress to Carrie's.

As I entered the dressing room, I almost creamed my panties as I marveled at how the dress draped my male body. It'd draped cowl neckline would fall sexily over a pair of silicone breasts and the V-cut back dipped far enough to show my back. With my red any-which-a-way bra, it would cleverly give the illusion of me being braless and sporting real boobs. The length was perfect, short enough to showcase my beautiful shaven gams but not too short it would spell slut rather than classy whore. The sheer billowing sleeves just spoke femininity, highlighted with french cuffs.

I trembled with anticipation as I paid for the dress and a pair of gold spiked red patent stilettos, along with a few pairs of black noir stockings and a new red lace garter belt. Oh, how I could not wait to prepare for this most interesting evening. The ever so kind sales lady asked if I'd need any matching panties and I shamefully declined saying the feel of the silk would be scrumptuous on my soft buttocks.

"Yeah, that and it will make for some easy access to that sweet pussy of yours, huh?" she surprisingly said in front of everyone in ear shot.

Embarrassed a bit, I merely smiled sheepishly and winked.

Next stop was the World of Wigs and Transformation Parlor, where I was treated like a lady in waiting. Complete wax job, nails, makeup, and a beautiful long strawberry blonde wig that fell down my back and folded ever so sexily around my face.

Packages in hand along with all the remaining necessaries to transform my shapeless male body into a gorgeous hot to trot transvestite, the girls showed me to the dressing room where I proceeded to become the woman within me.

Rebecca led me to the adjacent toilet and told me to bend over for a bit and expect to feel a rush of cold in my soon to be man-pussy. Doing as I was told I was filled in a hurry and then released in even more of a hurry all the nastiness that might turn off a future suitor. Next she instructed me to lie down on the table in the dressing room and she would tuck and tape me.

Cock and balls securely hidden and chest flesh taped to create the illusion of clevage, I stood and arranged the any-which-way bra so that no straps would show in the back and securely encased my D cup silicone tits with protruding areola and nipple in its silken cups. Next on was a mini waist cincher in red silk, along with the lace garter belt. Sitting now, I guided up the most luxurious black stockings over my freshly waxed legs. God, did they feel ever so good. Stepping into the gold spiked 6 inch heels, my ass felt twice as big and bounced as I strutted around a bit. I felt like such a whore, yet transformed into a sexy goddess when I stepped into that dream of a dress.

Just as I envisioned in the dressing room, it's cowl neckline fell ever so sexily upon my prominent and pert tits and after Rebecca placed the crowning glory of that beautiful blonde wig on me, my smooth silky back felt its length and softness. All I could dream of at that point was having some man's hands on the back of my head forcing me to drain his cock of cum.

A few sprits of Georgiou perfume and I was strutting myself into the parlor happily accepting all the wolf whistles and I gladly forked over the fees plus a handsome tip to Rebecca.

With a parting twirl, I bid farewell to my transformation artists and headed home to showcase my newfound femininity to Suzie.

Upon opening the door, I was surprised to see Suzie already in character and she looked butch as any man could hope. Decked out in a deep purple zoot suit, complete with squared shoulders and a dapper fedora to match, she looked like a perfect pimp.

I wasted not a moment in seducing my newfound "man" and coyly got cozy against her and slyly reached for her crotch and much to my disappointment found nothing dangling.

"I know what you are searching for, you little slut." replied Suzie.

"Well then, we will have to stop at the adult book store on the way over and get you equipped." I answered.

"Not before you put on your gift." remarked Suzie as she handed me a small box.

I trembled with anticipation as I opened the box and lo and behold were the prettiest gold custom made earrings. In small gold letters, the dangly jewels spelled out "JOHNS" on one and "SLUT" on the other.

I was grinning from ear to ear as I placed them on and loved how they felt so heavy and made me feel like property. I gave my big ol' John a big hug and kiss.

"Well, I had to have a name, didn't I and tonight you are my little slut, Desiree." Suzie, I mean John, informed me.

"Sure did and I love them and you for thinking of me, I'm yours to command, Johnny." I replied.

With that we parted the house and I fell into my submissive role following Suzie, now John's lead.

As we pulled into Erotica's Adult book store parking lot, Johnny told me I'd better behave and we were only here to get a strap on dildo for her, not to find some cock for me to suck.

I shook and strutted my stuff like any seasoned whore all the way to the door. Johnny was flabbergasted at how at ease I was surrounded by mostly horny old men and all the porn paraphernalia.

It didn't take me long to locate the dildo section and I found what I was looking for and that was Kong's life like massive cock replica. In life like skin, complete with harness and squishy balls. It even had crotch hair. It felt so real even Johnny was intrigued.

"A little large isn't it Desiree? Are you sure your tight ass can handle such a big head?" queried Johnny.

"It's that well defined head I love and yes I'll take it all or scream trying!" I replied smiling deviously.

As we paid for it, Johnny asked the clerk if she could use the restroom to finish out her costume, to which he replied it was out of order but we could use any booth we'd like.

I just grinned and led my man to the adult video booths. Picking out one big enough for two, I undressed my man's trousers and affixed Kong's massive cock to my pimp for the evening. It was so real and so delicious looking, I couldn't help but to back Johnny against the wall and start sucking it as if I expected to be rewarded with a mouthful of sticky man juice.

Suzie just smiled and called me her little cock sucking queen, then out of nowhere, let out a scream and almost pushed me down onto the sticky floor.

She turned around to find a big hard ebony cock sticking thru a glory hole and just started laughing her ass off.

"Well, whore, you know what to do." she said, guiding my head to the awaiting mystery cock.

I must tell you it was a welcome surprise and I went to work feverishly bobbing my blonde head back and forth on that swelling piece of black cock. I got so involved I didn't even notice the cold invasion to my man-pussy until I felt Kong's enormous head press against my anal canal.

Just as any seasoned slut, I backed up against my back door man with each incoming thrust and I must tell you I was working up a bit of a sweat getting both openings fucked and fucked but good.

It wasn't long before I felt the head of this magnificent cock in my mouth swell and pulse and I put a lip lock on it so I would hopefully not get any cum on my dress and I didn't have to wait long. Suzie had sensed what was about to happen and backed out of my now wide open man pussy and came around to watch her sissy hubby become a cum bucket. Gush after gush of sweet sticky hot cum came rushing in my mouth and down my throat so fast I had to rise to swallow and that's when one last shot of man juice hit my beautiful red dress about waist line high.

"Oh, oh!" Suzie exclaimed, "Now everyone will know you couldn't wait for the party." she continued.

"Clean me off, now slut!" she ordered.

I did as any obedient sissy slut would do for her pimp and knelt again and polished her knob brilliantly clean of my ass juices. All the while, in my mind, I couldn't help to replay her previous words, "Now everyone will know you couldn't wait for the party".

"Here cunt, freshen your lipstick and powder your cock sucking face, you cum dump and let's get out of here." ordered Suzie as she zipped her massive manhood up in her pants.

"What did you mean by the comment wait for the party", I asked as I powdered my face.

"You will find out soon enough my little cock sucking slut, don't forget the lip gloss honey. I want those puffy feminine lips of yours to spell cock pleaser." she answered.

Fresh as a daisy and Suzie zipped up with Kong's cock just bouncing in her trousers; I held onto her hand and strutted my way back into the lighted room filled with porn, rubber cocks, clothing and jewelry.

It was past the clothing section when I noticed a large gold belt with COCK SUCKER spelled out in gold letters and my devilish mind worked its magic and I asked my pimp if I could try it on.

Of course Johnny grinningly said yes and I clasped it around my cinched waist and noticed it covered the cum stain perfectly.

"Oh can I have it Johnny, can I?" I cooed, batting my luscious long black eyelashes as any wanting girl would do.

"Sure, you earned it you good little cock sucker you", replied my woman in disguise.

We gladly paid for the needless advertisement and sexily strutted our stuff back to the car and drove onto Carries for the party.

I couldn't help but to play with Johnny's cock all the way there including going down on it while we passed several truckers.

"You love being seen as a slutty cock sucker, don't you sissy?" laughed Suzie.

"Of course, always have! You should pull over and I'll treat one of them to a nice blowjob." I earnestly replied.

"We haven't the time and don't worry, I have a feeling you will have plenty of cock to suck at the party." answered my pimp, as confident as any seasoned pimp.

It wasn't long before we were making our way up Carries front entrance and several black gents were evidently greeting guests and parking cars.

As we pulled in, Johnny got out and handed the keys to a very handsome black man and I could see she was whispering something in his ear and before I could exit the car, he was in and pulling down his pants.

Suzie had made her way to my side of the car and informed me I was his tip and that I should make quick work of making him cum.

I needed no more instructions and took his cola bottle thick piece of limp manhood between my fuchsia painted lips and went to town. It was so thick I could barely get my mouth around its girth but I at least managed the head and I worked my tongue delicately in that sweet spot men love and before long my chauffeur was rock hard.

It took quite a while to get him to the point of him losing his load and I knew exactly when it was coming for I felt a strong hand on the back of my golden locks and force my face down until it was buried in his public hairs. With a good five inches of cock down my throat with the rest between my tongue and lips, my mouth was filled with shot after shot of hot sweet tasty cum and I swallowed and sucked to perfection until he was literally bone dry.

By the time the tears cleared from my eyes, I could see the black gents hands on his lap but I still felt pressure on my head.

"Finished slut? Taking cock that deep makes your eyes tear doesn't it sweet sissy cock hound? Good thing your mascara is waterproof huh?" I heard.

I could merely nod yes and I was allowed to rise and that's when I saw Carrie just grinning at me.

"I see you love cock as much as dressing up, don't you Desiree?" she said.

As she opened the door for me, I straightened myself up and searched for fresh lipstick in my purse.

As I was applying a new fresh coat of hot pink lipstick and gloss, Carrie said "Better get a good coat on honey for tonight is your night."

I couldn't help to admire her outfit. A pair of skin tight black leather biker shorts with her fine ass presented to the world sans leather over the bubble butt I had longed for so many times. A completely sheer tank top in black see thru chiffon showed off her more than ample tits. And those heels, God they must have been seven inches tall.

"Here sissy, Johnny told me you'd be needing this." and she placed a hot pink leather collar around my neck complete with bull ring and leash.

"Now follow me slut", she commanded.

As we entered her home, I could only see men, only big black ebony men and my man Johnny was in front of them all seemingly holding an auction.

Carrie took me center stage in her large living room and before I knew it, I was being shackled with an ankle bar and my neck leash was locked to a narrow cushioned table. When all was in place, I was teetering on my heels and all I could do to keep from falling over was to place my hands on the table. I must have looked like a fountain of a blonde bombshell. Ass high in the air and mouth cock high, I had no doubt what was next.

"Gentlemen, you have all been invited her for two reasons. One I personally know each and every one of you to be the most well hung black men in Buckhead and two, my best girlfriend here has a sissy husband that loves to suck cocks and has been begging her to fuck him." announced Carrie.

"Suzie and I both decided if it's men our sissy Desiree desires, then it's men we will give her but first you have to pay Johnny, who is in fact Suzie, Desiree's spouse." she went on to say.

It was then I heard the auction pick up speed and it wasn't long before I heard winners being announced and soon I had completely naked men streaming in front and back of me and I went to town on cock sucking and bucking back against so many men, it didn't take long before I was full of cum, front and back.

I must say I enjoyed every single minute of it including the cock by cock commentary from Suzie and Carrie. Both where quite impressed with my deep throat skills. I lost count of the cocks that had cum all over my face, down my throat, and in my ass. It was definitely a gang bang of a lifetime and I could do nothing more than collapse in blissful pain by the time the last cock spewed all over my sissy face.

As I drifted off into a cum filled haze, I could hear Suzie laughing and saying, "Now the little slut might be careful about what she asks for in the future. I can't wait until my dear sweet tranny husband hears our demands after seeing this escapade on TrannyTube."

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by Anonymous

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by Anonymous03/19/18

Hmm please

Long to be pimped out so lucky.
Sissy missy. NZ

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by Anonymous06/30/17

Love being a sissyboy

Love this ,and being pimped out too
My boyfriend he is going to pimp me as well one night to his friends
sissy emma

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