A Midnight Swim

Relaxing by the apartment's pool one Sunday, I relived the previous evenings midnight swim in nothing more than my long baby blue Eva Picone silk gown. The water had felt so good flowing between the silk and my nude body and the walk back to the apartment even better as I had a raging hard on from the clinging sensation of the silk over my drenched body.

I grinned mischievously to myself as I wondered if any of the beautiful women or men at the pool this sunny Sunday had seen my daring swim. Subconsciously I suppose, I cared as I had not come out of the closet fully as the hot to trot transvestite that I transformed into every weekend and I did still like a romp in bed with a woman even though I found sucking cock much more pleasing.

As I dreamed of dressing again that night, my thoughts were pleasantly interrupted by the introduction of one very busty girl who introduced herself as Karen and asked if this lounge chair was taken. I told her no and welcomed her to the sun. She ended up being very friendly and loosened up even more when I shared my jug of screwdrivers with her. Before long, she'd invited me back to her apartment for some more drinks and I eagerly said yes.

It was the normal girl apartment but what caught my eye immediately as I sat down on her couch was the very thick copy of Vogue magazine alone on the coffee table. The cover had a drop dead gorgeous model in a dress that I would have died to slip into. I suppose my gleam in my eye gave me away as I hadn't even touched it when Karen told me it was the annual fashion edition, three times as thick as the normal issue. She told me to feel free to browse through it while she changed, noting it had some killer clothes between its glossy covers.

As I flipped thru the pages, my cock tinged with excitement as I imagined myself donning the wonderful sheer hosiery advertised, all the makeup, the gorgeous dresses. Then the strangest thing happened as Karen reentered the room in nothing more than a baby doll nightie holding a long black wig.

She sat down on the couch and held it to my head and said, "No, wouldn't work for you," with a nervous giddy laugh. "I wore this on Halloween and no one knew who I was all night," she continued.

I was a bit taken aback but the screwdrivers in me caused me to reply, "Yeah, I'm more partial to being a blonde queen."

"Oh really," she giggled. "You certainly don't look like a tranny to me," she followed up with as she put her arm around me and thrust a wet tongue in my un-expecting mouth.

Well, my straight genes kicked in and we ended up in her bed for the rest of the night fucking and doing all the things that go with sex. I even asked if I could fuck her ass but she declined, although hinted it may be doable in the future if we played by the rule of what's good for the goose, is good for the gander.

Monday morning came soon and she was awake with my cock in her mouth and offered me a taste of my own sweet salty cum with a deep throat kiss which I readily swallowed.

"My," she said, "You are the adventurer, aren't you."

I couldn't reply quickly enough before she entered the shower and after she returned from her shower, as I lay in her bed, I watched her get ready for her teller's job at a bank.

She cussed having to wear dresses and complained about pantyhose.

As she was guiding them up her nicely portioned legs and ample rear, she asked, "Have you ever worn pantyhose?"

I honestly replied, "Yes, and I found them quite erotic."

"Hmmm," she answered, "I've got a girlfriend that would like to meet you and make you a girly boy one evening. Would you be game?"

"Sure why not, but not in that hideous wig you had last night." I answered following up with, "I think I still have my own blonde super girl wig."

It was then she turned and said, "Of course you do, you little swimming mermaid, think you can get it restyled by next Friday night. It surely must be still wet after Saturday night's swim."

Embarrassed but not too much, I answered, "Oh you saw?"

"Yes my little sissy, I saw and it's exactly why I seduced you into coming to my apartment yesterday," she said quite honestly.

She went on further to tell me that both her and her girlfriend Marcie loved to turn boys into girls and in fact preferred sissy men over the macho types. Seems they both had been dumped way too many times and vowed to make sissies out of as many men as possible. After seeing me take my swim, they knew I'd be an easy target and could possibly help them in their vengeful quests.

As she let me out on her way to work, she instructed me to show up fully in drag next Friday night and be ready for some fun.

I couldn't believe my luck and all week I shopped for the perfect outfit and also made an appointment with World of Wigs for new wig, make over and to have my nails done. I even asked off work the following week so I could live it up as Desiree the hot to trot transvestite with my new friends.

By Friday, I'd purchased the perfect outfit, a butt hugging skin tight mini skirt from Versace in black spandex with glittering highlights and a gorgeous sheer blouse in baby pink. Its cowl neckline would fall sexily over my silicone tits and my arms would swing with femininity with the flowing sleeves with hot pink pearl buttons. A pair of 5 and half inch spiked black pointy toe heels with hot pink leather soles would make my strut ever so sexy.

Arriving at Joann's business with travel bag in hand, she knew I was going all out again for another special evening. Joann had befriended this queen long ago and treated me like royalty, always giving me the best service and making sure she kept my style in wigs in stock. I chose a gorgeous strawberry blonde wig that fell to the middle of my back and with the front cut so as it fell inwards towards my pert tits. Fluffed and prettied up front, the bangs highlighted my newly arched brows and perfectly done eyes by her makeup artist with the false eyelashes barely touching the bangs with every blink. I felt so much like a woman. Once styled, body waxed, anal douched and make up complete, I went into the back room and changed.

Sliding into the Donna Karan noir French pantyhose made my legs feel like a million bucks and the faint hint of hot pink nail polish on my toes was the icing on the cake. A hot pink waist cincher would give contrast to the baby pink sheer blouse and its feminine touches of lace would speak the language of sex so readily. A matching bra held my D cup silicone tits complete with pert areola and nipple pronounced to the world I was one hot chick ready to be fucked. Donning the sheer silk blouse and buttoning the pearl hot pink buttons framed the curves of my new chest perfectly. Slipping in a Versace mini is any real girls dream and its fit and texture made my ass stand at attention, especially after slipping into the 5 and half inch pumps.

Arranging the strawberry locks so as they fell over my bouncy boobs, I felt 100 percent like a woman. A hot pink leather belt cinched so tight breathe was slow and deliberate, I opened the door and sexily strutted out to show the girls. I could tell they were waiting for me as they were playing Shanna Twain's I feel like a woman song. Oh, and did I ever feel like a woman.

Oh's and ahs filled the room and Mandy told me to sit my sexy ass down so she could transform my fingers into female daggers ready to massage that big cock I was surely bound to meet. An hour or so later and my fingers donned the most beautiful glossy hot pink dragon lady nails, each at least an inch long with a couple probably inch and a half. A few rings of bling I'd brought and Desiree was complete or so I thought as Joann came over and sprayed what she called "Man Juice" all over me. The smell was intoxicating.

She said, "Honey, not that you'll need it but this stuff does wonders for us girls and I expect you will have to fight off the men tonight or at least wear out the knees in those pantyhose. Better take some extra pairs, girly," she laughingly said.

I paid my bill and bid my beauty shop girlfriends goodnight as it was now time to introduce Karen and her friend to Desiree, as the daylight hours were fading to darkness.

I couldn't help to dome light a few truckers on the way home and was pleasantly rewarded with many a honks from my suitors of past experiences as Desiree. I desperately wanted to pull over and have a go at some smelly trucker cock but decided I'd best look my best for Karen.

I pulled into the front of Karen's apartment and strutted up to the door and rang the doorbell.

"So, this is our little sissy man," said one helluva domineering woman I'd not met yet, as she opened the door.

She was impressive to say the least, decked out in solid black leather pants, a skin tight black leather jacket and heels that matched mine less the pink soles. Her black eyes pierced mine as I introduced myself as Desiree, the hot to trot transvestite.

Karen came rushing to the door and went nut shit crazy over how I looked and drug me into her apartment. Making me twirl around like a model, she told Marcie that this was going to be so easy.

"Oh, yeah, Desiree, meet Marcie, the man hater I told you about," Karen said as I extended my hand to Marcie.

"Bitch, get on the floor and kiss my heels, you little sissy cocksucking faggot," I never shake hands with men.

Shocked but still intrigued, I did as told and actually loved sucking her stiletto, although it was over much too soon as she told me to rise and they discussed the evenings plans. I heard them talk about how I would pass easily enough for a straight bar.

With that they informed me we'd be going to Harlow's and that I was to find a sucker that would fall for me and entice him into one of the private rooms they would choose for me. All I was to do was to get him so horny that he'd end up with my cock in his mouth.

Once we got downtown, they saw a few hookers on the corner and decided I should be tested for my ability to attract a man and let me out on 14th street and told me to find a cock to suck, that they'd be across the street watching.

Obediently, I did as told and strutted myself out into the night as I'd done so many times before in my life. It wasn't long before a car pulled up and my eyes gleamed with excitement as I saw laid out on his leg a horse of a cock. At least 12 inches long, white and thick as a pony beer bottle, I told him I was free for a blowjob and he told me to get in.

I wasted not a moment in wrapping my lips around that monster head and sucked as much in my mouth as I could. My pink lipstick hardly even leaving a mark behind it's well pronounced head. I worked feverously and jacked him simultaneously with my hot pink dragon lady nailed hands. It wasn't long before I was rewarded a huge sticky mess of man juice and I swallowed every drop so as not to mess up my pretty face. I kissed it clean and oozed yummy sounds as I relished such a cock. God was it fine.

He thanked me and told me to tell Karen and Marcie I did just fine.

I could see the girls were just laughing as they made me stand on the corner a bit longer waiting for them to pick me up. I heard everything from slut, to whore, to faggot from the college kids that cruised by. Little did they know that if they stopped they would be in for a cock polishing job that would blow their mind.

Karen and Marcie finally picked me up and asked me how I liked that bottle of a cock. I told them I liked it just fine and was ready for some more. Karen said if I did well tonight that maybe he'd be back at the apartment and ready for some back door action.

"Oh god, he'd split me wide open," I replied.

The girls just smiled and we headed to Harlow's.

Once inside they left me to my tricks of the trade and with a fresh coat of hot pink lip gloss it wasn't long before a very nice young man was offering me a drink as he placed his hand on my thigh dangling ever so sexily from the high bar stool. I told him to be careful where he placed that hand that he might find something that bites. He just smiled.

We got cozy after a few dances where he couldn't keep his hands off my tush and I must admit I was in heaven. The scent of a man, the feel of his bearded skin against my cheek as we slow danced. I couldn't help myself when the dance was over and laid a very sensual kiss on him which he responded to with a very active tongue dance in my willing mouth. With that, I asked him if we should visit the private rooms. I could tell by his cock raging in his trousers that the answer would be yes.

As we entered the mirrored room, I wasted not a moment in unleashing that throbbing piece of man flesh I so eagerly needed and painted it wet with hot pink lip gloss and sucked it completely down my throat. He wasn't overly big, average I'd say, a good tuck candidate for the girls if I could coax him into treating me as I was treating him. Just as his head swelled, I grabbed it's based and squeezed off the flow and told him I needed a good back door fucking and promptly turned, lowered my skirt and hose and he guided his cock into my clean ass. In time, I had a good fuck going on and I abruptly stopped, rose and turned to him and told him I needed some attention before he got his rocks off and unleashed my own raging cock right in his face.

He was somewhat shocked but so horny that I don't believe he could have said no if he wanted to and just bathed my cock with his juices from those manly lips. It took me less than a minute to release a mouthful of sweet sticky cum down his throat which I eagerly went after with a deep throat kiss.

"Ummm good, wasn't it honey," I said.

With that no more uttered in barged Karen and Marcie and Marcie was holding a camcorder replaying this man's sordid act with their tranny cock bait.

He merely whimpered submission to their ever command and joined us back at Karen's house where Mr. Coke Bottle cock was awaiting. Karen took our new tranny to the fold into her room to get her all dolled up while I prepared to get split wide open by this massive piece of meat.

Marcie just rattled off her commands to me and told me what a good luck cock sucking tramp I was and that I'd be capturing more men for her every weekend.

I just cried in joyful pain as my ass was being filled to the brink of breakage and said, "Yes Mistress."