Debbie Does Vegasbyimhapless©
I wish to sincerely thank my muse for this story, DirtyDebbie!
Don't wet your pants reading the title. I'm not the Debbie who did Dallas, and if you're expecting that the "Does" in the title means that I fuck everyone who I come into contact with there then you will be sadly disappointed. I hope that my little sojourn to Vegas still interests you, however.
Let me tell you a little about myself. I'm thirty one, a buxom lass, 5'1", 130 pounds with DD boobs, and medium length blond hair. Once she became famous several people have told me that I look like Kellie Pickler's buxom sister.
I had to wear a back brace for several years because my little body had a hard time supporting my big tits. I started an exercise program to make my lower back muscles stronger and more flexible. It worked so I have not had to wear a brace in more than five years. I do need a very sturdy jog bra when I run, though, otherwise I'll either put out an eye or redden my stomach (ha, ha).
My first marriage didn't work out so well. My first husband, Boris, seemed like a basically normal guy when we married. He was smart, had a good job, and was nice and good looking. He wasn't a particularly good lover but I thought it would get better. I was disappointed when after two years of marriage sex with him was more like Labor Day than The Fourth of July.
Also Boris was not the most open guy in the world about fantasies or what was expected as far as sexual contact with others was concerned. I tried to engage him on the subjects a few times and was stonewalled.
I became suspicious of some of his activities, however, and found out that he was fucking two different bimbos (I hope that they got more pleasure from him than I did). While I had gotten a couple of "tit massages" from male friends I had never fucked anyone, and considered that off limits. I divorced his ass.
My present husband, Rob, is eight years older than I am. He is much more mature and communicative than Boris was, and he is great in the sack, having excellent oral skills as well as knowing how to properly move his dick in my pussy. He also loves tit-fucking, maybe even more than I do.
Rob, being more mature, is often willing to be at least partially open about fantasies and talk about sex in general. My three years of marriage to him have been wonderful.
Rob was coming up on his 40th birthday. For my 31st he had thrown a big bash, with a male stripper and a wet T-shirt contest, where one of his friend's wives and I were the only participants. I got lots of compliments and tit-feels (several under my wet shirt) that night, as well as a bunch of ass grabs, especially since I pretended to be drunk even though I was only slightly buzzed. Rob saw that I was enjoying the attention and only smiled.
Since Rob had been a great husband for his 40th birthday I told him that he and his three best friends, Justin, Ted, and Upton, should go to Vegas for three days and two nights to celebrate (leaving Friday morning and returning Sunday night). I told him that I'd work some overtime and pay for a private poolside cabana for the second and third days, and gave him all sorts of information such as the best prices and times on flights. If he and his three buddies shared a suite the cost would be reasonable.
Justin, Ted and Upton are all good looking guys. They're all about the same height and weight as Rob (roughly six feet, 180 pounds) but since Rob is young at heart they're all younger than he is. Upton is 35 and married (and the most consistent tit squeezer at my 31st party), Ted is my age, and Justin (the best looking of the group) is 28.
I gave Rob only two pre-requisites for his trip to Vegas with his buddies. First, he could not, under any circumstances, lose more than $500 gambling. As soon as he lost that he was done.
The second was that he could not stick his dick in any pussy or pucker hole. When I told him that he said "That's it?"
"Yeah I said," with a sly smile, "if you stick that thing in a pussy or ass I'll cut your nuts off and feed them to the squirrels."
"You do realize, don't you," he stammered with eyes wider than I had ever seen them, "that there are other sex acts besides pussy and ass fucking?"
"Happy Birthday, darling," was all I said, kissed him with a little tongue and then walked away. He was still just standing there stunned when I yelled over my shoulder as I walked away "don't expect any other presents from me." I giggled to myself.
While I was OK, as his birthday present, with Rob getting some non-intercourse action I also wanted to be in control of it, at least to some extent. I had second and third parts to his present that he didn't know about.
To explain the second part of his present I have to describe one of my friends to you. Rob knows that we are friends but he has no idea what good friends we are since I never saw any reason to tell him.
My friend's name is Kyleigh; she's 19, my height, weighs about ten pounds less, and has brown hair, brown eyes and a 34D chest -- I know because she and I talk about such things. She also has a very tight firm athletic body and perfectly toned muscles especially in her hard thighs and ass. She also has a beautiful girl next door innocent face and a smile that drives guys wild.
Kyleigh is a gymnastics teacher, not hard to believe given her toned hard body. Actually her big tits may have been the only thing that kept her from getting a gymnastics scholarship to college because they sure don't help in any gymnastics event.
Rob has an eight year old daughter, Madison, from a previous marriage who takes gymnastic classes from Kyleigh. Fortunately Rob and his ex-wife don't hate each other and Rob and I get to take care of Madison about ten days a month, and we never miss one of her many gymnastics exhibitions and meets.
I go to exhibitions and meets to support Samantha and Kyleigh. Rob goes to support Samantha and ogle Kyleigh, as do all of the dads there except a pair of gay-guy parents. Rob is so funny -- he wears sunglasses even though 90% of the activities are indoors. He says that the mercury lights in the gyms hurt his eyes. I just smile and laugh to myself.
The reason why Kyleigh and I are such good friends is that our parents' houses are right next to each other, and at one time I babysat for Kyleigh. Her parents are religious freaks who apparently would have been happy for her to remain a virgin forever. When she got to be a teenager the only way that she could get to go out was if I went with her. There were a couple of times that situations arose where her parents thought that I exercised extremely good judgment and would only let her go to anything resembling a social gathering where boys would be around if I was there.
Her parents were so wrong, ha, ha. I wanted Kyleigh to enjoy life and she is a very sensuous, fun-loving, sexy creature. Therefore I got her birth control pills when she was eighteen and saw to it that she could get some quality time with three different boyfriends she has had over the last two years.
Kyleigh is like my little sister and we talk about everything, including sex. She is not oblivious to the fact that all the fathers of her students ogle her -- she loves the attention.
Despite the fact that Kyleigh is 19 she isn't really emancipated. Her job as a gymnastics teacher, while she goes to the local Community College, doesn't pay her enough to really be economically independent. Plus despite what religious freaks and jerks I consider her parents to be she doesn't want to thumb her nose at them so -- at least for now -- she acts as a demure sexless daughter waiting for marriage before giving up her virginity.
Now to the second and third parts of my present to Rob.
One thing that Kyleigh has always wanted to do is to try stripping. The conservative clothes that her parents always made her wear as a teen left her with a desire for exhibitionism. She is between boyfriends and since her last one was very virile she is really missing having her sexual needs tended to; "I'm climbing the walls I need to be laid so badly," she told me just before I told her what I had in mind for the Vegas trip. It took her only about five seconds to agree to be a stripper for Rob's 40th in Vegas -- "If you can swing it with my parents," was her only concern.
"I can't guarantee that there won't be sexual contact by Rob's three friends -- or Rob for that matter," I said, smiling which after her statement about climbing the walls was sure to get her more excited.
Her smile was wider than mine. "I'm hoping so," she giggled, "and if you're OK with Rob and I getting it on, so am I -- he's cute."
"Yes he is," I laughed. "I don't care what you do with Rob's friends but with Rob no fucking, pussy or ass, got it," I said trying to act stern.
"Got it," Kyleigh beamed, giving me a big hug. "How's it going to work?"
"I'll tell your parents -- and Rob -- that I'm going to Phoenix for business. I already have found a perfect connection flight through Phoenix to Vegas, cheaper than any direct flight. I'll tell your parents that I need an assistant at a convention to help me with brochures, visual aids, etc., and ask if you can come along. I'll tell them it will be good pay and I will chaperone you," I told Kyleigh laying out the first part of my plan.
"That'll work," she replied gleefully clapping her hands together, "especially since even if they come with us to the airport they'll see us board a flight to Phoenix."
I continued to relate my plan/present. "I rented a private poolside cabana for Rob and his friends. The day after they get there, when all four are inside, you'll show up with a mask on pretending to be a waitress. I'll be waiting outside. You do your thing and afterward let the guys feel you up, and maybe give them blow jobs IF you and they are so inclined."
"IF?" she giggled.
"What happens after that is up to you, although I should tell you that while Justin and Ted are single Upton is married and I know his wife," I continued.
Kyleigh's Smile turned into an evil grin of anticipation. "Do I reveal who I am to Rob? I don't think that the others know me."
"Yes you do, though not for a while. But there is one other thing I'm going to ask -- and I hope that you'll agree."
"Hey, if you're going to pay my way to Vegas and get me all sexed up I can't imagine that I won't agree to it," Kyleigh responded.
"Before I reveal to Rob that I'm there I want you to ask him to fuck you. I put fucking other women off-limits and I want to test him. If he declines to fuck you he won't ever fuck anyone else because you're his ideal," I said.
"Really? Kyleigh said. "What if he says 'yes' though?"
"Then you leave because you don't want to see what happens next," I said, no longer smiling.
I really didn't like this ulterior motive part of my plan; however Rob and I were talking about having children. I really wanted kids but only if I could really trust him. I had no reason not to but having been burned the first time around I had to be sure.
Kyleigh's parents went along without hesitation, Rob and his buddies took off as planned, and Kyleigh and I flew out early morning on Saturday so that we would get to the pool cabana early afternoon. I had talked with Rob by cell phone and knew that he and his buddies would be gambling or going to a show until the wee hours of Saturday morning and there was no way that would make it to the pool before 1:30 or 2:00 p.m.
I had the perfect outfit for Kyleigh. It included a conservative pool cover-up with a series of almost sheer outfits underneath with pasties and a thong as the last items that would be removed. She and I were both so excited we couldn't wait.
We saw Rob and his buddies dragging their asses down to the pool about quarter to two. Rob actually looked better than the other three, and Justin was in the worst shape. They put their towels in the cabana then each took a quick dip in the pool, which seemed to revive them somewhat. Then they each ordered a drink and went into the cabana.
I intercepted the bikini-clad poolside waitress when she was bringing the drinks, tipped her $20 and told her that I had a surprise for my husband. She smiled and handed the drink tray to Kyleigh, who had put her mask on.
Kyleigh played her part perfectly; I know because I was able to see everything through a slit in the side of the cabana. I knew that it would be unlikely that I'd be seen since unless I was a poor judge of men the guys would be paying rapt attention to the entertainment. In my position I also had a job -- to play the music for Kyleigh's act and what followed.
As Kyleigh walked into the tent she said "Hi gents, who gets what drinks?"
"Where's the bikini waitress?" Upton asked.
"She had too many clothes on, so I took her place," Kyleigh smilingly replied. The guys looked confused by that comment but after Kyleigh said "Now I know that the Birthday Boy gets the vodka tonic," handing that to Rob, "but who gets these others?" the other three guys dutifully said who got what.
After handing out the drinks Kyleigh tossed the tray on the ground, closed the front flaps of the cabana, gave Rob a smooch on the lips, and said "Brought to you by Debbie for her darling husband's birthday."
That was my key to start the music. I stayed away from the slit I was peering through until I was sure that Kyleigh had started her act. After her cover-up was thrown to the ground I didn't have to worry any longer about any of the guys looking my way.
I was in awe at how good Kyleigh was. She not only could win any amateur stripping contest in the world but she was better than many professionals. All four guys were sitting there with their mouths wide open, their eyes almost popping out of their heads, and bulges in their swimsuits, as articles of clothing were flying left and right. Kyleigh was using her gymnastics skills to do back somersaults, the splits, and other maneuvers that I don't know the names of.
The highlight was when she pulled her thong down to her ankles exposing her perfectly shaped, shaved, pussy and then did a hand stand, slowly bent over backwards and ended up with her feet on Rob's thighs with her pussy glistening. She lifted her head and said to Rob "Would you mind removing my thong, I'm having trouble with it."
The four guys let out a collective groan.
After Rob enthusiastically did as he was told Kyleigh pulled herself up, sat on Rob's lap, smiled and said "Could you remove my pasties without using your hands?"
Rob was in heaven as he took his time gumming Kyleigh's tits pretending that he was trying to take her pasties off as his buddies howled. She giggled as she rubbed his shoulders. When it was clear that he was delaying she started massaging his cock through his swimsuit saying "What's taking so long, Robbie-baby. We can't move to the next step until you get my pasties off."
After expressing a startled look Rob pulled both pasties off with his teeth faster than you could blink. Kyleigh giggled some more then knelt on the cabana floor and tugged at his swim trunks. He was only too glad to lift his butt off his lounge chair to help.
When his trunks came off his stiff dick popped up almost hitting Kyleigh in the face. Another giggle from Kyleigh, then she said "Nice" as she grabbed his balls with one hand and with the other guided his shaft into her open mouth. His buddies started gathering around him but she playfully said "Back off, you'll all get your turn."
Rob sat with his head back with this big grin on his face as he fondled Kyleigh's tits while she practiced her art. With the guys gathered a respectable distance around I could see Kyleigh licking and sucking like a vacuum as she massaged one ball with each hand. Rob didn't last long before he gave a warning groan, "Oh shit, I'm gonna cum, oh shit I'm cummmmmin..."
I didn't know that Kyleigh swallowed, but she took his entire load and then licked her lips.
As promised she went to work on the other three. She gave Justin as nice a BJ as she had given Rob while he kneaded her tits. She had a different surprise for Upton and Ted.
I was somewhat surprised when I saw Upton naked. He has a really big cock, probably eight inches and almost beer-can thick. I could tell by the look on her face that she wasn't sure she could handle that big piece of meat in her mouth. She had the perfect solution.
She sat Upton on one lounge chair and had him grease up her feet and his cock with sunscreen, unfortunately the only lubricant in the cabana. Then she wrapped the cute little toes of both of her feet around his tube steak and started stroking. As she was stroking away she had Ted straddle the lounge chair she was on and started Hoovering his cock with gusto.
I marveled at Kyleigh's ability to multitask, and based on their reactions so did Rob and Justin. With her toes wrapped around Upton's dong she slowly stroked it. Every once in a while she would stroke the bottom of it with the ball of one of her feet while toe massaging his nuts. She seemed to be trying to time Ted's and Upton's eruptions because when Ted started a groan that indicated "I'm about to cum," she started moving her feet frantically along Upton's cock, using her toes and the balls of her feet. Ted was soon unloading in Kyleigh's mouth and just like for Rob and Justin she swallowed every drop. Just as Ted appeared to be ejaculating his last cum grenade Upton let out a loud whimper and sprayed his goo all over Kyleigh's feet and lower legs.
Once Ted moved away and slumped into a chair, and Upton had shot his last wad, Kyleigh demonstrated her incredible flexibility by bringing her feet and lower legs to her face and slurping all of Upton's cum off of them with her tongue and lips.
All four guys clapped, and Rob and Justin got hard again just watching.
After she cleaned herself off Kyleigh initiated my "test." She slid over to Rob, started massaging his balls and kissing the side of his face and said "How about a fuck, birthday boy?"
Rob mumbled something unintelligible as she planted a kiss on his mouth. When she let him up for air she continued "I've got a snug, warm, wet pussy just waiting for your meat."
Rob actually gently pushed her away and said, "Sorry, I'd like nothing better but fucking is off limits. I couldn't do it to my wife."
Kyleigh then removed her mask and there was an obvious look of realization on Rob's face of who she was. "Come on Rob, those sunglasses you wear for gymnastics meets don't fool me; when Samantha isn't performing you're ogling me. You know that you want me. One birthday fuck; I won't tell Debbie."
Rob took a deep breath, stood up holding his arms in front of him and said "Kyleigh you'd be an ideal fuck, but I'm just not going to do it to Debbie."
I was so pleased I slinked through the cabana flaps and said "Great choice Rob; not only do you get to keep your nuts but Kyleigh and I have a special surprise for you later."
Rob was startled when he saw me, and the other three guys started covering up their crotches. Then Rob got a big smile on his face and grabbed me and hugged me. "You little bitch," he laughed. "I don't know whether to kiss you or spank you."
"Maybe both," I laughed.
Then I turned to Rob's three perplexed friends. "Hey, dipshits," I cackled, "why are you covering up? I just saw all of you get your knobs polished by Kyleigh. You haven't got anything you're covering up that I haven't already seen."
Mechanically they all dropped the towel or swimsuit covering their parts, which had deflated. Nothing like your buddy's wife crashing the party to shrink one's cock.
Then Upton said "Hey, how come we're naked and you still have your clothes on?"
"What's fair is fair," I said as I dropped my robe, revealing my naked body. Watching the action had gotten my long nipples hard and they were sticking straight out from my big tits. All four dongs saluted the arrival of my big tits and tiny pussy with protruding clit, and that tit-maniac Upton whistled.