Young Tranny Ch. 6 Vegas Sugar Daddy Pt 2. free porn video

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Young Tranny Ch. 6 Vegas Sugar Daddy Pt 2.

This is the second half of the sixth story following "How I Started," and shares my experiences between the ages of 19-29. These are prelude stories to the series of "Playtime Stories" I wrote. I hope you enjoy them and comment publicly or privately - it turns me on for some reason! These stories (especially this one) are mostly true so enjoy! I LOVE COMMENTS!!!!

Saturday, a week later, we met again at the Power Trade and had more mind-blowing sex and about a half-hour after getting there Charles, or “Chas” as he preferred, my tall 40-something masculine, fit, fellow sex maniac, called me a whore and pushed me against a glory hole, forcing me to suck off a big black cock as he fucked my ass. After that he took me into the couch room, put me on all fours, and made me suck off any cummers as he pumped me. He called me his whore and other very dirty names he already knew I loved. I was very intense.
In between three fuck sessions over the course of the night we would go to a sex room, sit, rest, and talk. During these brief times that always seemed to end when someone went next door and started to fuck.

I learned a lot about him and he about me. Chas was a successful law professional who was a divorcee’ and had two girls with a boy in between, all in their teens and generally successful or at least not fucked up. He’d tried to make the marriage and relationship work, but his wife hated Vegas and returned east and then re-married. He saw the k**s during frequent trips east, but had no one else in his life and really didn’t want anyone. He was like me, pan-sexual and could not adhere to conventional sex mores. I had no idea what that meant then, but as he explained it, I felt it might be accurate.
He learned about me too. He quickly determined that I was a young airman stationed in the north end of Vegas. He said he’d also served and that my secret was safe with him. As things wound down around three in the morning, he invited me to a late-night breakfast at America’s diner. We both got so turned on by the looks I got from the other patrons that I followed him to his home for another fuck, this time, I stood as he held me against the archway into his kitchen. When he was done he asked me to feel free to stay since it was now morning and “I know how you blood-sucking sex-vampires are in the sun-light.” I accepted after getting my Rebeca-bag and my street clothes from my car.
I stayed en-femme until mid-day on Sunday. On Saturday night we went to a sex-store & arcade. He bought movies and some really big and expensive toys. He encouraged me to flirt with the other patrons and then took me into the arcade so he could watch suck off and get fucked by some strange cocks. We both got off on his role as pimp. Then after only about five or six strangers, we went to his house and fucked all night.
We put in the movies and played with the toys. We competed to see how much long black latex cock we could take up our asses, we played with massagers, and finally combined vibrators, blowjobs, and lap-dance fucking to round out the night. In the morning I woke to him eating out my ass and then him enjoying my ass with his good-morning hard-on. After he came I was so horny I went to the bathroom, re-did my makeup and went to the great-room with we’d fucked in all night long and put on a masturbation show for him using most of the toys. I won the cock-acceptance challenge too, by the way.

Sunday after lunch he found me in his lavish the shower as a guy.
Like the bedroom, the huge bathroom oozed sex. It was huge and I learned later that it originally was a bed room. The shower was rectangular and was the center-piece of the bathroom- he most amazing I’ve ever been in. You could have easily fit three or four showering people in there at once and probably ten people if they stood next to each other. It had a side showers alongside vertical metal hand-holds similar to those in handicapped showers in all four corners, a hose shower on the deep end, and a rain nozzle above the center. The tile was a pale stone that your feet gripped well. On one side was the double door entry, a wide opulent sink, movable vanity mirrors, a bank of lights (turned off), and a huge strong wooden bath-bench or bed with towels in it, along with lubes and condoms. In front was the bide’ commode along with a wash hose. To the rear was the standard commode. To the far end of the room was a whirlpool tub big enough for two or maybe three, if a lap-ride was an option. The walls were black tile except around the mirror and around the base of the tub, which were white. There was dim faux electric candlelight as the basic lighting and bright white spot-lights above and focused on the shower and with the darkened room it caused the glass shower walls to act like mirrors. The floor had a huge cushioned off-white faux-fur rug that served as a bath mat, and heaven only knows what else. It was amazing.
As I bathed, I was sad at the realization that I had to return to real life early next morning. I noticed Chas only after the whoosh of cool air into the shower as he joined me. Chas had apparently been enjoying himself as a voyeur, watching me clean all my private places that were so soiled form all the stranger-danger I’d experienced over the weekend.
Now, with Chas in the shower, I realized that he was a large healthy guy who was taller and more filled out than me. Standing behind me, ogling my shiny pale wet bubble ass, trim hips, and lean torso, his tall frame towered over me. As I turned to face him, he turned me through full circle to face the glass wall of the shower and bent me into position. I gripped the vertical bars and held myself in an “L”. The rain-shower poured down my ass crack. He used some soft soap and caressed my ass to wake my sex for what was about to happen. His thumb went in me, rubbed in a circular motion, pressing over my g-spot several times. My eyes rolled back in ecstasy. He pulled out and then reached around and pawed my nipples. Then he closed the distance and rested his heavy erect cock on my ass crack and pressed his upper thighs against my ass cheeks. I looked in the glass reflection to see him produce and put on a condom he’d apparently brought with him. He took a bottle of lube form a tray at the top of the shower I’d not seen and poured a generous amount into his hand and then put it on and in me. Then he dropped the lube on purpose, as if to emphasize the lust of the moment and gripped each side of my hips and ass and pushed down on me in a manner I was becoming accustomed to. He held me in position as he pushed himself into my sex.
I was sore, but his cock went where he wanted it to go, and, at that point, where I needed it to go. My insides were well-conditioned to get out of the way of Chas’ huge cock. It felt good and I exhaled and moaned as he fucked me deep.
He pumped rhythmically as the endless warm water ran over our bodies. He fucked me deep in the shower for a short eternity and then shut off the water, pulled out, turned me to make me suck on him though the condom, and then pulled me up and then pulled me out of the shower. Without drying me off, he forced me onto my stomach and to the furry bath rug. My arms and legs splayed outward and were useless for resistance. His massive body mounted me, pushed into my sex and he resumed the rhythmic fuck on the bathroom floor. The lust was intense and he was going sooo deep. The floor was firm couldn’t bend or let me escape his deep fuck motion. I took it like a good boi. I began to moan. “Ohhhhh, ahhhhhh…uhhhhh…yes…”
Chas said into my ear in a low tone, “Yessss….take it …. Fuck back into me… take it, fuck me and moan like a bitch…”
I could feel his cock hitting and then passing my g-spot and taking me to orgasm. I moaned exactly as he wanted…”Ohhhhh…yessss…fuuuck meeee….uhhhhhh…”
Chas then took it to a new level, “Call me sugar daddy you little girly whore…call me sugar daddy…and beg me to fuck you…”
Pressed against the fur, the erotic friction quickly mounted inside my boi-cunt as well as along the outside of my cock. I was close to cumming and his words took me past the edge. I began to cum. As I felt the first shot of semen flow out and onto the furry rug I grunted in a femme twink guy/gurl voice, “Yessss Suuugar-daddy…fuck me…use me Suuugar-daddy…ohh! Yessss…I’m your… your whore…ahhh…uhhhh… Suuuhhhagarrrr-da..dah..dadddy!!”
I came, his fuck motion pumping my cock’s semen deep into the rugs furry depths. I turned my head and he saw and felt it happening. Chas pumped me hard several times and came with me, grunting as he pushed hard and up into my body for that first blast, and then sharp and deep for about ten or twelve more cum-shots.

When it was over there was no weird uncomfortable silence or awkwardness. He smiled and said I was hot and told me to clean up “as well as such a dirty boy like you can.”
Again, I was surprised at how much fun he could make a very degrading, nearly insulting thing be. I smiled as I picked myself off and turned on the shower saying, “Now, if I can just not be disturbed by rude needy people…”

We had a mid-day bite watching the end of a war movie and then we resumed watching a tranny movie we hadn’t gotten through the night before. It starred Vanity and she was a totally hot slut in the movie. We got horny, but instead, Chas knelt, opened my legs, and sucked me hard. Then he stood, turned and bottomed using me as his anal fuck-toy. I fucked him deep and hard, like he’d done to me and came in him without leaving the couch. That was the first time we skipped the condom.
He came just after I pumped him full form below, but just before I softened up. He caught his cum, licked it up, and held both side of my head as he passionately, like a lover, kissed me. Something I rarely did. In fact I mused as his tongue left my mouth coated in his cum, that the last time I’d kissed passionately and shared just-shot cum had been with the officer girl who was now out of the area getting gang-banged (about six months before she got kicked out).
Chas ended the kiss and smiled as he pulled away, now kneeling between my legs, my slimy cock against his neck, looking up at me. He blinked and said, “I better be careful, I might fall in lust with you…you whore.” Once again, he made a possibly awkward situation comfortable with demeaning tongue-in-cheek humor…I was starting to love that.
As he got up to get hot wet towels to clean everything up I smiled and realized he was different. He didn’t take things too seriously and added fun to the F in Fucking. He was and still is a true hedonist and smart ass.
Over an early diner of sautéed shrimp, my things packed and me ready to depart, Chas asked me to consider moving in with him. He said he wouldn’t feel bad if I still did things with others and that it would be fun to share others here at his house.
“I’m a true Sugar-daddy with cuckhold tendencies and a frequent desire to switch and dominate a whore like you.” He showed me his daughter’s old room, the original master bedroom before the remodel he’d done to make his fuck-chamber. The room was huge and had its own door and bathroom.
Chas leaned against the door-jamb to the bedroom and said, “I really mean it. I want this to happen. Maybe it lasts a few weeks, maybe much longer. I have been going to Power Trade looking for someone like you for years – sexual person with no relationship expectations. Now that I have found you tell me what you need. You know I’m comfortable, so you tell me what you need. You say it’s too far from base, I loan you a car. You need your space, I say, I am gone about a week a month back east and a few days during the week in L.A. You say you need privacy, I say fine, but don’t shut me out. You don’t want a gay relationship, I don’t either. I know you well enough and I know what you are dealing with and I know this is an amazing opportunity…for both of us. I can trust you. We know enough about each other ti be discreet and develop that trust.” He sold his offer vigorously. He wanted this to happen.
The following Friday I moved in and by Sunday my ass was really, really sore and the bathroom rug was pretty soiled.

Charles, or Chas, became my sugar daddy. To his neighbors I was his live-in roommate and house sitter. He was gone often, so this was accepted. He had me keep a low profile and look like a guy coming and going from his home during the day. Since his neighbors were wealthy retirees I could easily dress and make it out the long driveway and onto the main road without being noticed as a gurl.
When the doors were closed, we did it all. We slept together, apart, with others. We rudely awoke one another and put each other to sleep with massages. We had women and couples join us. I willingly traded myself as concubine or cuckhold for an amazing home to live in. In return he provided that home, board, and he showered me with gifts and every gurly I needed or wanted. My wardrobe filled and my look matured.
With a few exceptions, this became as much his home as mine for about three incredible years. When his ex-wife and c***dren came to Vegas to visit Chas took care of me with rooms on the strip and money as long as I promised to share my stranger-sex stories.
Over the next four years we had our ups and downs. If I was gay I would have romantically loved him, but as it was, I did love him, but not in a soul-mate manner. He was a sexual lover in the purest form and so was I.

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My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the...

3 years ago
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My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.In August 2007 I was 24...

1 year ago
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Dream Tranny

Dreams can be strange, sexy things. Your wife may be a stunning knock-out, way the fuck out of your league, but I bet she ain’t your dream girl. No, your perfect fantasy angel has the big tits and pretty face you love so much, but she’s also got something extra: a big ol’ dick between her legs. Sorry, wifey, but tonight may be a good evening to spend with DreamTranny.DreamTranny.com is a site with history. They’ve been around since 2000, making them one of the older shemale porn operations on...

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1 year ago
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Vegas

Vegas By The Professor "Have you ever seen anything like it?" The man who asked that over my shoulder was the last person I would have expected to say that. Lt. Matt Henshaw, Las Vegas Metropolitan Police Department, had probably seen more strange things than most people could ever imagine. I didn't answer him, because if I said yes, I'd be compromising classified material, but in fact, this wasn't the first time I'd seen anything like it - or rather pictures of it during...

4 years ago
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Part 1 Country Western FUN in Vegas Angel had a

We were at home 1 night watching TV when the phone rang. I answered it to hear an old friend of Angels ask to speak to her. He was a Country Western star & band leader that Angel had met years before we met the 1st time when he was performing at a bar she was a cocktail waitress at then. He took a liking to her then & during a break he asked her to dance & after the show to a late dinner. Dinner then led to his room & more fun that night. Then he asked her to join his troupe...

1 year ago
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Two Japanese girls in Vegas

I did deserve the holiday so I made sure I was a long way from home to enjoy it. I booked a hotel in Las Vegas to play some poker and perhaps get the money back. It was a hard time finding a hotel with vacant rooms. There was some kind of event going on and almost every room was booked well in advance.I didn't care. When I finally arrived at the hotel I only wanted to get to my room, take a hot bath and get to bed. The 10 hour flight had almost killed me. So when I got to my room and opened it...

2 years ago
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Stag Night Tranny Gang Bang

I really still don’t know why, to this day, i said i would go with Ross to the Stag night. It was probably one of my more stupid decisions in life!! I’d met Ross a couple of times before, mostly at the S Club in Merton. Ross was about twenty three, really good looking, and loved the whole cross dressing scene but didn’t dress himself and described himself as an ardent ‘admirer’. He’d approached me at the bar one night and we’d got talking. Although I was much much older than him it only seemed...

2 years ago
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Stag Night Tranny Gang Bang

I really still don't know why, to this day, i said i would go with Ross to the Stag night. It was probably one of my more stupid decisions in life!!I'd met Ross a couple of times before, mostly at the S Club in Merton. Ross was about twenty three, really good looking, and loved the whole cross dressing scene but didn't dress himself and described himself as an ardent 'admirer'. He'd approached me at the bar one night and we'd got talking. Although I was much much older than him it only seemed...

3 years ago
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Couple Finds Another Plus Tranny

While I was in the military, there were many opportunities to see some of the wild and crazy sites and people of the world. One time in Japan a bunch of us in a mixed group (men and women) went to a show that featured transsexuals. These were men who now dressed and acted like women. All of the men/women featured had breast implants to additionally make you believe they were real. The show was very exciting with each of the trannies on stage showing us they were as good looking without their...

1 year ago
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What Happens in Vegas Part 1

The Explanation The computer mouse danced over multiple LCD monitors as Brian listened with lax enthusiasm to the various voices talking through the speakers. CNBC played on a large television near the window, the volume only barely discernible. Two German Shepherds were strewn along the two couches near the window, lying lazily as if waiting for Brian to finally find a tennis ball to throw. The various Directors from Finance, Sales and Operations recited their monthly reports: sales, profits,...

Wife Lovers
1 year ago
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The Italian Sugar Daddy

I had been on the hunt for the perfect sugar daddy since my birthday back in January. I’ve dated a couple of men but no one I found intriguing enough to want to keep going with. I wanted what I had at one time, a daddy who was everything to me. A lover, a best friend, someone confident in me and himself. But with the changing of times and of course ageing twelve years, I was having a hard time finding ‘the one.’ I was ready to give up when I started getting messages from a man who was local to...

1 year ago
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First Time with Tranny

So this is the story about how I got my first experience being a bottom, and why it was with a tranny.I was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...

4 years ago
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Im a Meat Packing Girl Tranny

I didn't go looking for a tranny, shemale, dickgirl, or whatever derogatory term a homophobic world has labeled women that happen to be packing a penis. In fact, while I had messed around a little with the man worm, back in college and with a drunken buddy a few times, I considered myself 100% a hetero male, in love with the female form and a total horn dog for a beautiful woman. I must admit, I've jerked off more than a few times to shemale porn on my computer at home, wondering what it would...

1 year ago
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My Tranny Schoolgirl Fantasy

As I sat on my couch, i was thinking, "Being alone doesn't have good perks. Maybe if I wanted to dream something naughty, it might be cool." So, I closed my eyes, and I dreamed of a very naughty tranny schoolgirl who would do what i like. All of a sudden, I heard a sexy female voice say to me, "Hey Brian, you bad boy, you big stud." I woke up, and there was this hot tranny girl who was dressed as a naughty tranny schoolgirl. She had nice lovely pigtails, a very sexy tied tight white top, in...

3 years ago
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My first time as a bottom and with a tranny

So this is the story about how i got my first experience being a bottom, and why it was with a trannyI was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...

3 years ago
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Nate and his tranny neighbour Part 3

Nate and his transsexual neighbour part three, as always hope you freaks enjoy and let me know what you think ; ) Nate woke up thinking about his last two encounters with his hot big-dicked neighbour. Having never had much experience with woman to having the hottest sex he could hope for was a dream come true. However as he slowly stroked his hard morning wood he realised he had yet to fuck Jez, her gorgeous tight ass in lycra was a vision to behold. Wanting nothing more to feel her pretty...

1 year ago
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Fun with a latina tranny

So I'm a big fan of a big tranny cock in my ass. Just throwing that out there early on here.So this past summer I decided that with my school being off I should get some tranny cock as fast as I could. I went on a site and set up a new account, hoping for the same luck I had a few months ago with a hot black tranny named Jade and her friend. I quickly found a very nice 20 something tranny names Maria who said I would do. We went through a few chat sessions, with our cams on and I convinced...

3 years ago
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Amy The Tranny Chapter 1

I met Amy at an adult theatre in town.She was dressed to nines in a mini skirt, tight halter top, and pumps leading up a pair of fishnet clad legs. I invited her into a private boothand once inside, went over her price for someadult fun. She told me I couldn't fuck her as shewas on her period but I knew something was up and asked her flat out if she was a tranny. She looked at me wearily and slowly nodded her head. I assured her I was into tranny sex and she relaxed and asked if I was into just...

4 years ago
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Tranny Delight

I had been feeling particularly horny one day and waiting for Joe to come home I got to thinking about having sex with a black woman and then watching as Joe took her and then thought even more that perhaps a black tranny might be a bit more fun. So when Joe came home I easily talked him into going down to the alternative nightclub we had visited once before and off we went. Upon entering the club I saw that it was as crowded as usual and Joe and I took up a small table and settled with our...

3 years ago
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The Perils of Pauline Tranny at the Truck Stop

Paul sat behind the wheel of his Mustang, the windscreen opaque with heavy rain. It had been raining hard for the last hour and he was hoping it would have stopped before he reached the truck stop. He looked through the windshield as the wipers lazily swept back and forth across the glass. The sodium vapour lamps bathed the parking lot in an orange hue. The blacktop was slick with rain and puddles had formed in the numerous potholes. The lot was quiet; as it usually was at 8:30pm on a Tuesday...

4 years ago
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Vegas Ch 03

This is my first attempt at writing, having been inspired by a small band of authors whose work I immensely admire, and I have attempted to occasionally incorporate a flavour of their imagination in this story in tribute to them. I know that having completed the novel, I have learnt so much more than I knew at the outset. Two areas of feedback are welcomed: 1. Comments of encouragement that will inspire me to write more… and constructive criticism that will help me improve. 2. Voting that...

2 years ago
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Fear and Lusting in Las Vegas

Fear And Lusting In Las Vegas By Cooper There is nothing more depraved than beer drunk Southern Baptists on a tear in Las Vegas. Nothing. Spending most of the year wearing pants that are three sizes too small in the crotch area, married to frigid women with bee-hive hairdos on their heads-- and in their skirts-- pounding Bibles and burning crosses, these hypocrisy-drenched Jesus freaks come to Vegas once a year, hit the Casinos and make Jim Morrison look like Jim Baker. Let...

1 year ago
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Loving Las Vegas

‘CindySpice, you are an amazing woman.’ Hello Las Vegas! That was my motto for three beautiful nights and two and a half days. They say that what happens in Vegas stays in Vegas, how true that is. At least it is for me. I had never been to Las Vegas before though I’d had the opportunity to go once before but just didn’t think it smart at the time. Looking back I’m grateful that I didn’t go when I had the chance because I don’t think I would have done all that I did this time, probably not even...

1 year ago
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VEGAS GETAWAY CHAPTER 1

VEGAS GETAWAYA STORY OF drunkEN SEX & DIRTY SECRETSFICTION BYAMANDA WRIGHTERCHAPTER 1My head was pounding as I tried to fall back asleep. It was no use, of course. I yawned involuntarily and stretched my legs, trying to remember how to open my eyes. I was hung over...seriously hung over. As my eyelids fluttered, I flinched at the brightness in the room. It was probably mid-afternoon by now. I had been up drinking until at least four in the morning. But hey...that's what you're supposed to...

2 years ago
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What happens in Vegas stays in Vegas

WHAT HAPPENS IN VEGAS, STAYS IN VEGASI’d never been in Vegas before, but the other day my sugar daddy called me and asked me to go meet him there. Seems he had some kind of a conference and that would give him an excuse to stay a few extra days and he wanted me to be there with him. I said sure, why not; I’d never been there and I liked spending time with him, plus I was going to stay in a fancy hotel suite (he had to book two rooms for appearances) and he was surely going to buy me lots of...

3 years ago
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What Happens in Vegas

Dorothy Clark looked around herself as she stepped into the Sagebrush Hotel in Las Vegas, Nevada. The sound of slot machines and other gambling activities seemed magical and new to the small town housewife. She looked in every direction and was constantly awed by the glitz and glamour of her surroundings. Though the Sagebrush was a newer and smaller casino, they had spared no expense in making the place seem magical. "Come on Dor," called the voice of her friend, Terri Stevens. "Good lord,...

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