More Vegas Nights

Thanks for checking me out.

All of my stories are true involving events that took place while I was growing up in Las Vegas also known as Sin City.

Las Vegas being the entertainment destination for a variety of reasons and one of those being sex. During the 70's and 80's and even earlier, Las Vegas was a city without the restrictions of today meaning that to be a cocktail waitress, show girl, cigarette girl, dealer, hostess basically every job in the tourist eye you had to be very sexy in appearance, being hot was part of the job a big part. Every hotel had a secret competition to which place had the best looking women.

All of these women had to live somewhere, usually close by the Vegas Strip where most of the big hotel casinos were located and my neighborhood full of two story apartment buildings had quite a few.

As I became more attracted to the clothing these women would wear, with the cocktail waitresses in black fishnet stockings or fishnet pantyhose and high heels at every casino. Most all of the women including cocktail waitresses, keno runners, front desk workers, restaurant waitresses all wearing black bras semi exposed under their uniform to boost their hotels image and because it was all about the tease to get the tips. Black lingerie and underwear seemed to be the standard attire for Vegas Casino women, which is most likely the reason for my preference of wearing black when I play dress up.

The Strip had areas around the main hotel and casinos that were off limits for prostitution that the hotel didn't supply. The streets leading to the strip was where you would find those women, the women walking the streets picking up horny men for sex. The area around the now Hard Rock Hotel at Paradise and Harmon going down towards Flamingo road and up towards the strip casinos was where I liked to go as a teen for a leg show.

When I got my drivers license I would plan a night of dressing up and watching the hookers walk up and down the street in their best "pick me for sex" outfit's with short skirts and heels picking up horny men. They were nothing like the majority of hookers you see today addicted to drugs, these women flew in from out of town staying at one of the smaller motels just off the strip for a couple days to fuck and suck their way to riches. The majority of these women were showgirl material with great legs and bodies worth the money they charged. For the men that wanted something cheap they could go downtown or by the Showboat on boulder highway for a deal.

I would spend time hunting lingerie to wear, searching laundry rooms of the apartment buildings in the neighborhood tracking down a black bra and panties, hopefully garter belt and stockings but for sure some pantyhose and something to wear over the top like a full slip or nightgown. As I found the items I needed I stashed them in a bag in a nearby buildings laundry room until Friday night came and the girls would be out in force.

As soon as it got dark I would drive around the area down flamingo road taking a right on paradise road as I scouted for the ladies of the night. At harmon I'd make a right and up that road which was a common walkway for hookers walking up to the strip, then after checking that road making a turnaround in one of the apartments parking lots and retrace my drive also looking for a place to park an play.

I would pull into one of the many dark dimly lit apartment parking lots on harmon or one of my favorite places which was across the street from the hard rock casino on paradise but down a ways towards another smaller casino at the corner of Flamingo and Paradise. Having these two casinos fairly close made this sidewalk a busy path for tourists and hookers.

In this parking lot I could park my car real close to the sidewalk or back a row a little further about twenty feet surrounded by other cars. Able to watch people walking down the sidewalk just a few feet away giving me a great field of view of the women was ideal. I was unnoticeable, unless they really looked my way people had no idea I was there.

Once I found my spot to park and play, I would get out of my clothes and put on the fresh outfit of sexy things I recently stole from dryers.

My excitement was undeniable with my cock swelling up as I put the items of clothing on. Rolling up the stocking to the toe to put my feet in one foot then the other like I have watched women do. I squeezed my body into the pantyhose pulling them up my long legs and over my ass caging my hard cock in nylon.

Sitting in the car trying my best to be invisible to the occasional person walking bye, I put on the bra and panty making my look more complete my excitement building up even more. Putting on the black nightgown I shift my body around on the seat to adjust my new outfit and gown with a little adjustment to my dick and balls. Now I'm ready to play.

When I dress up in women's lingerie and stuff it's like the boy in me leaves and the tramp in me comes alive wanting to play the role of a woman as I play with my dick, fantasizing about being one of the women I see in xxx movies and magazines, or one of the many women I've seen walking the streets picking up men to suck them off or fuck them for cash. Since the only parts I have equal to a woman would be my warm wet mouth or my tight asshole, so those are the parts I use and my dick becomes off limits, even though I do have multiple orgasms and can cum when my ass is being fucked. I've cum many times while sucking on a cock depending on how worked up I've made myself prior or if I've sucked a lot of dicks then I can't help but cum even without touching myself.

Sitting in the car patiently waiting watching for a sexy tourist or hooker to walk my way teasing my cock with my fingers rubbing the nylons encasing my hard young dick. When a hooker comes walking bye I start rubbing on my cock as I try to stroke it thru the clothes and with my eyes glued to this hot looking woman for sale. Fantasies fill my head as I wait and watch for the night's street walkers to pass bye.

Then walking into view comes a long legged brunette with her blouse unbuttoned all the way down just tied in a knot showing her tone stomach muscles. Her tits weren't that big but perfectly bulging up from her bra as she strutted slowly down the street heading my way.

Struggling to get a grip on my throbbing cock through the nylon pantyhose as I watch her, my fingers touching pulling at my hardon as she walks slowly down the sidewalk. Soon with anticipation I was getting a real good look at her long legs, she looked to be over 6'foot tall with these high stiletto heels on just made her stand out.

I was fixated on her, my eyes devouring every inch of her while wrestling to get a hold of my dick that was pulsing and throbbing trapped by the pantyhose I had on. With the panties pulled part way down I still couldn't get a grip on my impatient dick when I accidentally touched off the car horn for a quick beep and instantly our eyes made contact.

Even though I tried to play it off as an accident, I couldn't take it back. She was looking right at me a little confused because I had been sitting there in the car not just pulling in to the parking lot to get her attention like most of her clients would do.

I was frozen, afraid to move thinking she would just continue on her way down the sidewalk but she had locked her eyes on me able to see something wasn't quite right. A teen boy sitting in a car in the dark and looking to be wearing something not normal for a boy clothes in the 70s.

I watched her as she looked around then started to walk my way. I lost focus on the situation my eyes glued themselves to her body, gently swaying side to side as she stretched her long legs with every step like stilts.

Bending down looking right at me through the window of the car she could see I was wearing women's clothes. With my clothes thrown into the back seat and me sitting there wearing these clothes with an obvious hardon and a few drops of sweat on my face. The car windows partially down to get a draft of air.

Smiling at me with these beautiful tits bulging over her bra

"I'm getting in" she says as she walked around to the passenger side of the car, opening the door, letting herself in.

Her legs so long and with her heels on her knees were close to the dash and her skirt hiked up on the seat exposing the side of her tight ass. The smell of her perfume filled the air as I sat frozen in the seat.

"What are you looking for?" she said in a soft calming sexy voice while she looked me up and down with a little smile on her face showcasing the pinkish lipgloss she was wearing.

"How much do you have to spend honey?"

With a shaky nervous voice I told her that I had no money which is why I was parked there in that parking lot hoping to get myself off while I watched the women walking down the street and jacking off in the ladies clothes.

"Where did you get those clothes, are they your mothers?"

She asked while smiling at me as she looked me over seeing the bulge under the nightgown.

I was trying to hide my cock holding my hand over it but uncontrollably I squeezed at it unknowingly drooling from my mouth as I stared at her tits only inches away.

Precum wetting through the pantyhose and onto the nightgown made it impossible to hide, but I tried.

"I will make you a deal... I will sit here and talk with you while you look at me and jack yourself off... for a ride down the street to where I'm staying. Deal?"

"I'm tired of walking in these heels." she says as she held her hand out to shake on the deal.

"Deal?"

My heart pounding and my mind spinning hearing her offer as I can't help but rub on my dick with her sitting there in the passenger seat.

Yes, deal I said and put my hand up to shake her hand and seal the deal.

My hand must have been a little wet with my precum because after our handshake she put her hand up to my face ordering me to lick my wetness from her fingers, putting two of them to my lips. I barely opened my mouth and she quickly rubbed her two fingers on my lips.

My cock was screaming to be let out from its confines, wanting to stretch out from within the tight pantyhose that had been trapping it for hours.

She reached down between her long legs with her right hand giving me a perfect view of her amazing looking tits, bulging against the fabric of her designer bra looking like a pair of grapefruits they wanted to be released from their restraints.

I was watching her, my eyes glued to her beauty while tugging at my cock trying to get it free enough from its confinement so I could stroke the hell out of it.

She lifted the lever to her seat sliding it all the way back allowing her legs to stretch out, giving her more room and raising her short skirt up above her ass.

She saw the difficulty I was having with the pantyhose I had on.

"Hard time" she said as she laughed while watching me tussle with my outfit.

"Don't be so nervous... take off those panties... it will make it easier!"

I pulled the panties down off my left foot which was easy to do without having heels on by lifting my stocking covered foot up and out.

" You don't like wearing heels?" she asked

I love wearing heels and seeing women in heels was a real turn on I told her, but that I didn't have any to wear and only got to wear them if and when I was at someone's house or able to wear my moms if no one was home.

She was turned to the side with her back to the door, her legs semi spread in front of me. She then asked how I got the clothes I was wearing so I openly told her with embarrassment and shame about having to take items from dryers just to masterbate in, but she strangely understood.

Then bending her leg, lifting it up and putting it with her stiletto heel across my lap, her leg covered in designer thigh high stockings causing me to let go of my dick preventing me from even rubbing it.

The feeling of her leg on my lap brushing up against my cock has me spinning and ready to orgasm.

Now I have a clear view of her pussy just hidden underneath a pair of sheer panties able to see a small patch of hair right above her honey hole. Smiling at me she was enjoying the tease game she was playing with me. As she talked about her shoes, she was moving her foot around on my lap rubbing her heel against my cock making me gasp my cock ready to burst. She knew exactly what to do she was a pro, lifting her foot off my lap putting it to my side giving me a full view of her lightly covered pussy.

I lifted the nightgown trying to find the top of the pantyhose with my hand, my hard young cock straining against the nylon exposing the large wet spot surrounding the tip of it from my precum excitement.

"Here let me help!" she said as she positioned herself in the seat reaching down with her left hand, touching my cock sending electric shock like sensations all through my body as her finger nails tickled my skin thru the nylon material. With two fingers she pinched and pulled the nylon pantyhose up and away from my dick, using the right hand she poked a fingernail right through the material ripping a hole.

As soon as she released the pantyhose from her fingers they snapped right back into position but this time my cock stood straight up rock hard with a drop of my teen precum balancing on the tip of my mushroom headed shaft. I watched as she took a finger capturing the glistening drop of juice from my dick and putting it right to her lips licking it with her tongue before putting her whole finger in her mouth to taste me, I almost exploded my load but able to hold off.

The mental games playing in my head doing my best not to cum while having multiple mental orgasms was something I had trained myself to do. Extending that moment of orgasm made the fun last longer for me since my transformation was not as often as I'd like, I learned to extend the pleasure as long as possible knowing that once I came the fun was over.

I was on cloud nine living a dream sitting in my car wearing women's lingerie with a stunning almost naked totally hot sex worker talking with me while I played with myself.

Her comments about my dressing up and how much she liked seeing me dressed up in women's lingerie type clothing and how perfect my hard cock looked was giving me motivation.

She was shifting around in her seat teasing me flashing herself at me knowing what she was doing to me as I worked my cock with my hand in slow calm strokes.

With precum lubing my cock as my hand pulled and squeezed at it turning the mushroom head a light purple.

I asked her if I could see her pussy and she told me that's what men with money pay for and that I should save up my money but that she would show me her tits if that would help.

Already having multiple orgasms from just her teasing sexy looks and barely able to hold back much longer I watched as she reached up cupping her breast and with a snap she had unhooked a front clasp pulling her bra open exposing her perfectly shaped grapefruit sized breast with hard pink nipples the size of a number two pencil erasers poking out high and proud.

That's it, suddenly streams of cum shot like silly string from the head of my dick. Spurt...spurt...spurt three rapid ropes of cum shot up onto the nightgown as I held the base of my cock pointing it away from the dash and steering wheel making sure not to get any cum on the car.

White sticky cum covered the front of me even getting some on my face, just having the most powerful explosion to date. My body going limp but my young cock still standing tall as the last of cum oozing slowly from within running down the shaft.

My head tilted back in a daze from pure extasy still holding my cock in hand suddenly feeling a warm wetness engulfing my cock only to look down to see her sucking the last remaining cum from my dick.

The site of her with most of my dick in her mouth, her beautiful pink lips surrounded my shaft and the pulsating feeling from her tongue swirling under the rim of my mushroom head caused another orgasm somehow finding another burst of cum to shoot into her mouth.

When she was done with my cock in her mouth she stopped lifted her head smiling at me.

"That's the best part..... honey you taste real good... I'm impressed!"

"Now you can drop me off!" she said smiling at me while she put her bra back on.

We talked as I changed back into my clothes to drive her to where she was staying, during that conversation she told me that if I saved up at least $50 that she would be happy to do this again and that she would be back in town every other weekend, writing down her beeper number on a piece of paper telling me that she expects to hear from me two weeks from now Saturday morning 10am.

To be continued...