Vegas Weekend with Fiance's Sister

Author's notes:

This is my first submission after being a reader for some time. Constructive feedback is welcome.

This is based on a true story from my past experience.

I wrote it in the first person present tense to give it a try.

All characters in the story are over 18 years of age.

Thank you.

***

One: Thursday - The Long Weekend Begins

The sun is almost down and the city is just waking up after the day's ritual hangover recovery. Las Vegas, no place like it. It really only looks beautiful at night, much like the strippers, prostitutes, and club girls who will start to appear after full dark. It's Thursday night, I'm in the City of Lights, and I'm alone and exhausted. I lay down on the king size bed and drift through my thoughts realizing this is the first time in probably six months or more that I've had the luxury of just thinking things through.

This is supposed to be a bonus for all the hard work I've put in over the past six months. I was surprised two weeks ago when my boss suggested I come to the technology conference at all, they usually don't bring interns and I'm sure there was a waiting list for a chance to visit Las Vegas on the company dime. But my boss and I get along great and he somehow got me on the invite list with the condition that I work the company booth at the conference. Unfortunately what he didn't know is that I am broke. Paying for my own college has taken six years so far and I still have a semester to go. All the cash I'm earning is earmarked for getting through the rest of school, paying off my debts, and saving for the next phase of my life with Lisa. So I don't have the extra cash to gamble or get lap dances.

The conference wrapped up earlier today and my boss and colleagues already left. Since it was my first time to Vegas my boss threw in the extra perk of letting me stay at the hotel through Sunday night and take off Friday and Monday from work, albeit unpaid. That would normally be considered a big reward but considering I worked the booth every day since Sunday for twelve hours a day while only getting paid for eight hours I'm guessing he felt guilty. Or maybe he was just in a good mood as I know he frequented the strip clubs all week and I saw him walking toward the elevators with his arm around a young, busty woman who was not his wife a couple of nights ago.

I've had to content myself with my hand the past six months, and I've been so busy I haven't even done that as often as I needed to. This week in particular I've just been too tired and depressed seeing all the other guys having fun with me not having the money to join them, not having Lisa here, and missing her. Going to strip clubs is not really my cup of tea anyways and prostitutes are definitely out with me being engaged. But damn I was horny if I thought about it. My balls actually hurt from being so full. Hell, I'm young and used to either sex or a masturbation session at least once a day. My body just doesn't know what to do with a week hiatus.

At least things are going to change this weekend, although not in the sex department. My future sister-in-law Sara is going to join me Saturday, which upon consideration is pretty strange considering most women wouldn't want their fiance spending the weekend alone with another woman. But I guess Lisa trusts me, which she should as I have no plans to make a move on Sara. I have never cheated on a girlfriend and I don't intend to start now. Especially when it will affect my plan.

Two: Reflections - Meeting Lisa

"The Plan" is my ten year roadmap which started when I was midway through college. I was completely broke, eating only ramen, potatoes, and spaghetti because I couldn't afford meat. I was living with four other guys in a dumpy apartment. And I had mounting credit card debt to pay for books, food, and occasional entertainment. The Plan became my way out of this temporary state of affairs. It originally involved living a spartan existence with a focus on getting through school with good grades, paying down debt where possible, using internships and on-campus jobs to earn money and gain experience, and landing a great job after college. After meeting Lisa it has come to include getting married, having kids, living in a nice house, and all the other trimmings. Okay yes it is a little bit silly and cliche, but I am sick of being poor and crave a sense of stability.

Lisa and I met almost two years ago through one of my best friends, Rob. He and I were working at a tech company in my hometown of Austin, Texas on my third rotation as an intern. I've had to go to work frequently between semesters to pay the bills. I'd known Rob for awhile at that point, Rob and I worked together on and off at that same company and had connected my very first day of work when he invited me to go out for some beers. That same night I met my other best friend Jeff when the three of us hit the Austin bar strip where you could get cheap beer, great music, and hit on hot women.

Thinking about my friends I reflect that they aren't of the highest moral standards. Rob has a serious highschool-sweetheart girlfriend that he intends to marry, but that doesn't stop him from picking up women, including prostitutes, wherever we go. He is also a hard drinker and occasional drug user although that never seems to affect his prowess at work where he is considered a technical genius. Jeff doesn't have a girlfriend, mainly because he is noncommittal and an acknowledged selfish lover, and will stick his dick into anything that will accept it. He is in marketing and on the fast track to management.

Sad to say, but both are completely self-focused and the reality I suspect is that I shouldn't count on them for help if I really need it. I can't really judge though as I am no angel. In the past I've joined them numerous times on visits to the Laredo boys town across the border and I've had my share of one night stands and experimentation. But I tell myself that at least I was single when I did this, I've grown up, and I'm empathetic to the feelings of others.

It helps that they are attractive too and I have to admit that most of the women I've met over the past several years have been because of these guys. They are aggressive and boisterous while I am naturally quiet. They tend to initiate the interactions with groups of women and I was always happy to participate and leave with my share. Rob isn't particularly tall but he has a boyish face and charm with dark brown hair and sharp wit. Jeff is a big guy who works out constantly, has some interesting tattoos, an all-American face, wavy blond hair, and is an avid conversationalist. It's funny that Jeff has the larger body but Rob is hiding the torpedo.

Awhile back we had gone camping and during some drunken revelry had stripped naked in front of the fire. Rob had gone first and after he pulled down his shorts Jeff and I let out a snort at the monster that was revealed. Even soft it was at least six inches, he said it was nine and a half inches hard. He reminded me of a satyr and we all laughed at the comparison. I went next and revealed my assets which I am not shy about. I'm 6'4" and am happy to have a proportional body including a solid eight inchesl. Jeff was reluctant at this point and tried to beg off, but we insisted and when he pulled his shorts down we couldn't suppress our laughs. For all his body size his dick was barely visible and must have been on the short size even erect. I dubbed him Turtle and we laughed. Although Jeff went along with it I realized later it probably hurt his feelings and we never talked about it again.

Thinking back to the day I met Lisa. Rob was working on a different team than I was and his old officemate had gone back to school a week before. He showed up at my desk bragging about his new officemate who was a total hottie. I had to check it out and was introduced to Lisa. The moment we met a spark ignited for me. First Lisa is just my type. She is on the taller side at 5'8" with long toned legs and a slim build weighing about 110 pounds with modest, perky breasts that fit her well. She has smooth olive skin, black hair, and black piercing eyes on a heart shaped face with slightly upturned nose and full lips.

We ended up chatting for awhile and for once I had no problem carrying on a long conversation, it just seemed to flow naturally. Rob must have felt awkward after a while and he excused himself. I went ahead and asked her out for that Friday night.

Rob was jealous and bugged me all week about "stealing" her from him.

Three: Thursday Evening - Making Calls

The ringing of my cellphone jolts me back to the present. I anticipate the call is from Lisa and am a little nervous that she will give me a hard time. She has a habit of putting a downer on any of my plans that don't include her, usually by picking a fight or being controlling just before the event is about to start.

"Hello?" I say with a little caution.

"Hi! It's Sara. Are you ready for me?" A cheery voice says. "I've been packed since yesterday and I'm so excited!"

With some relief I say, "Hi Sara. I'm definitely ready for some fun and relaxation, it's been a tough week, in fact it's been a tough several months."

"For me too. I can really use this."

"Do you think we'll go to any clubs or nice dinner restaurants? I have a few nicer clothes but not much." I'm not much into clubbing or fancy restaurants but I have to consider Sara's interests as well as my own.

"We are going to be in Vegas, so of course we should go to some clubs. Maybe even some strip clubs." She says playfully. I wonder if she is kidding?

"And after I win big I'll treat you to a nice dinner. So yes to both. And I hope you didn't forget to bring a swimsuit, we need somewhere to sleep off our hangovers and the pool is the best place to do it. You'd better be able to keep up with me. I need you up all night!" Sara teases.

"At least you have a positive attitude." I say. "Thanks for joining me by the way. I'd be stuck here by myself otherwise, probably watching reruns and drinking beer, pretty depressing."

"Yes, very depressing. Probably watching porn instead of reruns though. And no problem at all, even though I'm sure I was your last choice. I've never been to Vegas, have always wanted to go, had no better options, and who better to spend the long weekend with then a hot guy." She lets out a little snort. "But seriously, you and I have always gotten along and I don't think it will be a problem to share a room."

"I don't know why Lisa wouldn't come. I know she has to work tomorrow and Monday but you'd think she could at least take off one day. We haven't seen each other for six months."

Originally I had thought I'd see Lisa at least a couple times over the six months apart. We'd even talked about it, but she's always had some reason why she couldn't come. And whenever I've suggested visiting her she reminds me that plane tickets are expensive and that I need to save money. Very practical I guess.

"Don't worry about Lisa. Trust me she'll be fine. I want you to focus on you and me having a good time."

Yeah, I definitely don't want to be thinking about Lisa all weekend. "What time does your flight get in again? Are you sure you don't want me to meet you at the airport?"

"My flight gets in at 2:20pm and don't worry about it, I'll take a cab. It's too bad I have to work tomorrow, otherwise I'd be there. We'll just have to make it up when I get there Saturday. You'd better be ready to party all night!"

"Okay, I can't wait!" I exclaim. I really am excited and really ready to have some fun. "Oh yeah. I wasn't able to change hotel rooms. So don't be surprised when you see the king bed. I'm not trying anything, really. The room has a pullout couch and I'll sleep there."

"Sounds dangerous." She says in a teasing voice. "What would my sister say?"

I think about Lisa. Putting myself in her place, with her boyfriend spending the weekend with another woman in a room with just one bed, what would I think?

"Ummm. You don't think Lisa is upset do you?" I ask Sara.

"No. Why should she be? Sorry about the last comment, I was just kidding. She's not staying home this weekend, believe me. So why should she care if you have some fun too. Besides, " She pauses for a moment like she was looking for the right words, "Let's just say I know she's been having a lot of fun this summer while you've been working your ass off. You deserve this and she doesn't have a right to say shit about it."

I'm a little surprised to hear Sara use profanity as I don't recall ever hearing her use it before. She is also right. I don't know why she hesitated telling me that Lisa is going out. I know she is hanging out with friends so it's no surprise, what do I expect.

We wrap up our conversation with plans to meet at the hotel room, get dinner, and hit the strip. I agree to take a nap and drink some espresso to make sure I can "last all night" for her.

After the phone call the room is again quiet. Should I go out? Should I stay up and wait for Lisa to call? Call her? I should probably just go to bed early and catch up on much needed sleep.

Somehow Sara's tone when talking about Lisa troubles me. I know she is spending a lot of time with our mutual friends, including Rob and Jeff. But I trust her, right? She is trusting me.

Regarding this weekend I had almost decided to just go home with the others today instead of taking my boss up on his offer. But I really need a break from the 90 hour work weeks I've been putting in. I had called my friends but no one could take off or wanted to come with me, even with the free hotel room. I had almost accepted the idea of spending this long weekend alone when Lisa was the one who mentioned that her sister Sara, who was also interning in southern California, was complaining that she was bored and needed a break. So I had called her. She had agreed. And now we were going to meet Saturday for a couple nights of fun.

The thought of Sara in the same room is enticing. I can't deny that she is a beautiful, sexy woman. Lisa had introduced me to her sisters about a year ago when we started getting serious. Sara is 22 and a year younger than Lisa. She is only about 5'3" and more curvy than Lisa with long luxurious black hair, round bum, and larger, fuller breasts. She has a similar face and skin tone to Lisa, being olive skinned with a heart shaped face. Her eyes and full mouth are more expressive than Lisa's which matches Sara's personality better . She is more bubbly and outgoing than Lisa. But each of them is both physically and mentally attractive in their own ways.

I let my mind drift over thoughts of what sharing a room with Sara will be like. I've only seen her a handful of times in jeans and shirts. Seeing her deliciously curvy body in a swimsuit or nightshirt will be interesting. I feel my pants starting to get a little tight just picturing it. For all her personality Sara has always struck me as a little naive about men. From talking to Lisa it didn't sound like she had dated much. Oh well, I'm in a committed relationship with the girl's sister, so I know these are only fantasies.

I am just thinking I should go get some kind of dinner when the phone rings again.

"Hi Aaron." Lisa's curt voice comes from the other end. "I said I'd call you before you went on your 'vacation' with 'my sister'." The emphasis is on vacation and sister which tells me she is not entirely okay with our weekend.

"And are you sure it's a good idea to take off both Friday and Monday from work?" She continues. "You don't get paid for that. And your spending money on someone besides me."

"Look, I've been busting my butt and working a lot of overtime. I'm spending money but only on myself. Your sister is paying her own way. I need a break. I wanted you to join me if you recall, hell I've wanted to see you for months but you're the one who can't seem to find time. And I told you I couldn't find anyone else to go with me. Remember you're the one who brought her up." I feel myself getting defensive which I hate.

"Well you didn't have to sound so eager about it. I know she's had the hots for you since she met you. She's probably fingering herself right now thinking about you."

"Lisa, come on." I blurt. I can't believe her tone.

She cuts me off. "You don't need to check in with me. In fact I don't want you to. I'll be out with friends anyways. Let's just talk again when you get back to your place on Monday."

More things are said, many of them not nice. I hate that she always gets me angry right before things like this. The comment about Sara having the hots for me is enticing. But I'm sure that was just said to provoke me so I don't give it any validity. It is really unfair that she has been going out, partying, and spending money for months while I work to earn money for our future and now she is giving me a hard time.

Even so the thought of Sara rubbing herself is on my mind. What if she is? I feel my dick thicken and reach down to stroke it wondering what Sara's breasts would feel like, what her pussy would taste like.

But then the thought of Lisa's other comments come to mind and the mood passes. I go downstairs and find a place for a cheap, quick meal then to the gym for a bit and finally I lay down early exhausted.

I am so tired I enter that deep meditative state somewhere between sleep and wakefulness where I can play back memories in full, vivid high definition in my mind.

Four: Reflections - First Date with Lisa

Thinking back to that first date it hadn't taken long for me to find out Lisa had a wild side. We went to a Mexican place and got buzzed on margaritas before going to a local amusement park and driving go carts around the track. Lisa drove so recklessly she ended up almost flipping her cart but instead wrecked it into a set of barrels, then ran over to my car laughing while I looked on with concern. She bent into my car and kissed me hard, sliding her tongue into my mouth passionately. As my tongue danced in her mouth she bit it playfully.

When we got to the car she said, "Let's go back to your place since I have three roommates. I don't have any condoms though." I had never been with someone so blunt, or so ice and fire. Seeing her at work I would never have guessed she would say that as she was just so professional, smart, quiet, and reserved. Where had this side come from?

At that time I was living with Jeff and his pseudo-girlfriend Kim. I knew Jeff was out of town but Kim was still around so I just hoped Kim was asleep already.

On the drive to my house she leaned toward me so that I could see down her shirt to her firm breasts. I put my hand on her thigh feeling the smooth skin, I doubted she had to shave much since her hair was so fine and there was very little of it on her arms. She put her hand on mine and slid it up under her skirt so that my pinky was pressed against her hot slit.

"I'm so turned on Aaron." she purred. I was instantly hard as a steel rod. She reached over and placed her hand on my bulge and smiled. "Now that's what I'm talking about. I love tall guys." I was glad she was impressed. From looking at some porn sites I know I'm not enormous or anything, just proportional to my height but better than average.

I could feel the heat coming from her pussy and began to stroke my fingers up and down the outside of her panties. Driving buzzed with a sexy woman rubbing your dick and promising to fuck your brains out is not the easiest thing to do. So I was very happy to pull into Jeff's place. We made out in the car for a few minutes and then made our way up to the house. There was no sign of Kim which was good. Lisa went into the guest bathroom to clean up and I went to the second bathroom, but then I couldn't find any damn condoms. Jeff must have used them all. Shit!