Snow in Philly

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A crossdresser's first time.
1k words
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This following story is true.

Snow in Philadelphia had closed the airport so I would be delayed at least another day in Minneapolis. I had intended to spend only a single day in meetings and catch the late afternoon flight home, but the Mother Nature had other plans. I booked my hotel for another night and grabbed a cab for the ten minute ride to the Mall of America. I might as well do some shopping.

Straight to Macy's lingerie department where I found a pretty white satin and lace corsellette, an exquisite stretch lace French cut panty, and two pair of silk seamed stockings, one tan the other black fishnet. Three hundred dollars later I was out in the mall and found a fabulous pair of black strappy heels on sale, and after a quick stop in the CVS for some makeup, I stopped in a sports bar upstairs for a bite to eat and a cocktail.

An hour later I arrived back in my suite and tossed the bags on the bed. The tub in the spacious bathroom had a built-in Jacuzzi.I started a bath and looked forward to a good soak in the soothing jets of hot water. I went back into the bedroom while the water ran and called home to check in, but got through only to the answering machine.

I undressed and slipped into the wonderful fluffy robe provided by the hotel. I retrieved my ever present emergency stash from my travel kit and sat at the desk and ground one of the tight buds into a fine ground mound of manageable pinches. I stoked a pinch into the pipe and took a deep pull. After another, I virtually floated into the bathroom and tested the water. I dropped the robe and gently settled into the, just this side of scalding, water.

Flipping on the jets I immediately wished for a glass of good red wine. Without turning off the Jacuzzi I padded wetly into the sitting room and almost settled for a pedestrian white wine from the mini-bar. Instead I called room-service and ordered a fairly nice merlot and asked for delivery in a little over an hour.

I went back into the bath for almost half an hour. Before unstopping the water I sat on the edge of the tub and shaved my legs. The light over the bathroom counter was perfect for applying makeup and I carefully applied layers of shadow, liner, lip gloss, and mascara. I decided to get dressed before putting on my wig and nails and my cock was rock hard begging for relief.

On the bed I separated all the bags and found the white stretch lace panties. I slipped them on and the oozing precum from my yearning cock had formed a wet spot on my new panties. I smoked another pinch of herb and returned to the bedroom. I slowly pulled the corsellette up over my legs and ass and it fit tightly around my torso. I slipped my arms through the straps and straightened the garters.

There is nothing quite like the feeling of brand new silk stockings on newly shaven legs. I shuddered in pleasure as I rolled the stockings and nearly came as I attached the garters. The shoes fit perfectly and when I went back into the bathroom and saw my appearance in the mirror I could not help pull out my desperate cock. Within minutes I came on the tile counter in thick spurts of cum. I was resisting the temptation to lick it up when I was startled by the knock on the door.

I clipped on my earrings and quickly put on my wig. I threw on the robe and calmly walked over and opened the door. A nice looking guy probably in his thirties brought the wine service in, he offered to open it, and he smiled at me sweetly as I signed the bill and he quietly left the room.

A few minutes later I heard another knock at my door. I peered through the peep hole and saw that he had come back. I opened the door and after he nervously looked up and down the hall he pushed politely on the door and I let him into the room.

Wordlessly he stood in front of me and stared into my eyes. I knew what he wanted and I threw off the robe and slowly got on my knees. He smiled down at me and unzipped his pants. I reached into his fly and found his semi-erect manhood, it was nicely thick and smooth with a big head. I moved in closer.

His cock was at my lips and without hesitation I kissed it. Then I licked the thick head and grabbed the smooth thick shaft. I slowly worked my lips over the head and took him slowly into my mouth. He was groaning as I steadily stroked his shaft as I took him deeper. After only a few more minutes like that he grabbed my head with both hands and gently, yet forcibly fed his cock to my mouth. His first shot of hot cum hit the back of my throat and then he unleashed a torrent of his musky goo in my mouth. I was surpized at how hot it was. I swallowed most of it and he abruptly pulled his cock from my mouth. Barely saying thank you, he zipped up his pants and nearly ran from the room.

For most of my life I had fantasized about sucking a cock while dressed. I had finally done it and it was perfect. Impersonal, yet extremely erotic. I was completely different person now, but in a good way. Yes, in the end I am a cocksucker. I was amazed at the texture and smell of another man's cock. I was thrilled that I had aroused a man and he wantonly filled my mouth with his cum. And best of all the snow hadn't let up in Philly.

I would be with him again, but that story is for another time.

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6 Comments
AnonymousAnonymousover 2 years ago

Too short of a story.

jackbirdjackbirdover 4 years ago
sexy

nice short story. I love dressing and sucking a nice cock and love swallowing a good load. My last hotel encounter was about a year ago. I was chatting with a guy on line for about a year before we finely met. I greeted him at the door wearing a red very short mini dress, crotch-less black pantyhose, a peek-a-boo bra black and red striper 6 in heels. I had full make-up on bright red lips. He grabbed me kissed me hard then pushed on my shoulders. I undid his pants as he took his shirt off I pulled his shoes and socks off then his pants and boxers then started sucking his uncut cock. Once he was hard he pulled me to the bed I got on my hands and knees near the edge of the bed he went down licking my hole then he rubbed his cock up and down then started entering me. It was a mix of pain and pleasure and I was moaning like a bitch in heat. He pounded me for around 20 mins till he unloaded deep in my.

worththewaitworththewaitabout 12 years ago
Green with envy

I'd love to give some guy (better yet, guyS) a bj in a hotel room. Tell me more!

AnonymousAnonymousabout 12 years ago
Hot hotel time

WOW ! I would love to have that happen to me some day here in San Francisco,I check into a hotel and dress in a sexy baby doll set then get fucked by a hunky big dicked stud DAMN !!!!!

AnonymousAnonymousabout 17 years ago
my fantasy

many times in hotel rooms i've worn panties and other flimsies and longed for a knock on the door.

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