Jamie the Blac Sheep

This is my first attempt at a submission. If you're looking for a quick, upfront bang tale, it might not be for you. I like stories that simmer, then explode. I welcome comments/critiques. Also, if this goes well, it might be an ongoing thread. So the end of this story may only be the beginning.

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Jamie was the black sheep of her family. Her father was a devout pastor, her mother a huge supporting factor in the community, and her sisters were models of virtue, she did things a little was smart, beautiful, outgoing, successful, got along with everyone, and commanded everyone's respect at work. The only reason why she could be considered a black sheep was that she acted like her utterly respectable family only 98% of the time. If they had known about the other 2%, it would have rocked the family's idea of itself to the core. After that analysis, black sheep isn't the right description. Actually, Amy was probably the wolf in sheep's clothing.

*****

Introducing Jamie:

The beginning of the year had been extremely stressful for Jamie and her boyfriend Will. They both worked at the same boutique investment bank. Technically, they weren't supposed to have interoffice relationships, but everyone in the office knew to keep their damn mouths shut about it. The two acted more professional than anyone else, and no one wanted to lose either of their talents. The couple could basically print money and keep investors happy even when the portfolio seemed on the brink of oblivion.

Jamie and Will met at the firm. He was an impressive kid too: all the right schools, played the right sports, smart as a whip, and a handsome guy. They immediately hit it off and within two or three months of working together, their work lunches turned to after work drinks, after work drinks turned to romantic dinners, and romantic dinners turned to long nights in bed.

Jamie truly was a professional. She graduated from an Ivy, did exceedingly well there, and then started at the firm. There was never a grammar error in an email, her work was entered on time, and she looked the part. Looking the part can be difficult for a female in finance. They had to compete with the good-looking, successful guys who frequently took advantage of gorgeous women after work. The trick to Jamie's look was that she looked beautiful but made large efforts to present the power of beauty and not become Type B submissive beauty who was just a hopeful wife.

At 5'7, Jamie was tall but not too tall. She usually kept her dirty blond hair in a ponytail at work. A normal day at the office would see her wearing nice dress slacks that hugged her ass, but would allow a little room as they ran down her long, slender legs. They were enough to reveal that she had an amazing figure, but not enough to cause whispers. On top, she opted for a tight women's button up work shirt. Her full Bs, possibly even tipping toward a C cup gave her more than a full handful up top, but again, nothing to cause whispers if she passed down the hall. In sum, she blended in perfectly and gave no one the impression that she was anything other than a conservative businesswoman.

*****

"Uhh," Jamie thought to herself as she left work at 11:25 pm late that Wednesday afternoon. She was worn out. Physically drained. Mentally exhausted. "Just two more days. In two days' time, I'll be on vacation at the beach." She knew she was having 'light at the end of the tunnel' fatigue—the kind of tired where you know you're so close to something and every moment between now and then seems to take infinitely too long. That tension had been slowly building for weeks. Between the long hours and the stress of working in finance when the whole market at any moment could ruin all their hard work, Jamie felt the need for a release. And the more Jamie began to admit it to herself, she knew she needed a big release.

The vacation had been planned by some of her high school friends. They had all grown up in the same school area (some going to public, others private), the same church (Jamie's father's church), and the same group of church friends. With all that described, Jamie enjoyed the fact that they were her long-time friends who happened to be church-ey. These girls weren't saints. They all knew they had lost their virginity by their freshmen years in college, they went out drinking, and would make mistakes with boys. But overall, they were good girls and didn't have random flings. Of the four girls going to the beach, only one didn't have a serious boyfriend—Claire. These were the types of girls that she could present to her family and receive approval, but she could also explore some of the more unseemly nightlife options without too much of their judgment.

*****

Friday afternoon finally arrived. Jamie had taken a half day so that the group could start off around noon and make the seven hour drive to the beach in time for a fresh seafood dinner and a night on the town. Jamie stopped by Will's office, closed the door behind her, and wrapped around him giving him a long, deep "I'll miss you, and see you in a few days" kiss. Will understood how happy she was to be taking a much needed break, and he wished that it was the two of them that would be headed out for a long, relaxing weekend. He knew that it would just be another weekend where he'd probably put in about fifteen hours of work over the weekend.

Jamie piled into the car with the other three girls and they headed off. Rachel was driving. It was very like her to drive. Socially, she took charge of the girls' activities. She had a fairly mundane job, and Jamie let her organize everything because she was tired of doing that every minute she was at work. Delegate responsibility of thinking of what to do: That was one of Jamie's first feelings of release for the weekend.

When the girls arrived at their hotel, they quickly unpacked in order to enjoy as much of the night as they could. It was a typical beach condo. It was a one bedroom, one and a half bath place. In the living room, there was a fold out couch and a very comfortable looking recliner. As the girls unpacked, Emily started to twirl around some of the bathing suits she had bought for the trip. Emily was a classic flirt. She'd tease men she met, and every blue moon she would let them take her home. She wasn't an angel, but then again she was a lot closer to an angel than a slut. Needless to say, some of the suits Emily brought were on the risqué side. Emily was a voluptuous girl. She was two inches shorter than Jamie, but outweighed her by twenty pounds. It wasn't chubby pounds, it was woman pounds. She had full breasts that had to have been DD and full hips. If she wore some of these things around on the beach it was going to attract attention.

That night the girls enjoyed their dinner and drinks. All the girls had a pretty good buzz, but they also had the fatigue from the work week piled on top of a seven hour drive to the beach. They headed back to their room about one in the morning. Emily and Rachel took the bedroom. After Jamie thought about it for a second, she realized that there really wasn't even a discussion about it. That was mildly annoying, because they were all paying the same amount of money and they would be much more comfortable. After thinking about if for a minute, Jamie gave up the thought. "That makes sense" she told herself. "Of anyone, Emily will probably need the bedroom for a visitor and Rachel put all this together so she probably deserves it."

The slight off-putting fact about this arrangement was that Jamie was now tagged with Claire. Jamie loved Claire and thought of her as one of her best friends, but there was no way she could get around the feeling that she was hopeless. She still lived at home with her parents. She had a job in "fashion," and that was exactly what she wanted, but she was floor rep in a local boutique—a glorified checkout girl who occasionally gave fashion tips to bewildered husbands or fashion-ignorant passers-through. Further, Claire had never really had a real boyfriend. She had hooked up with guys from time to time, but even that was limited. There were a few reasons for that: 1) she was extremely average looking (not bad but far from good, 2) she didn't like putting out (so guys rarely made the effort), and 3) she didn't drink much and when she did it was lightly (so she didn't even have "woops" moments). Guys referred to her as the "Mother Hen" in the presence of women and "a cockblock that would stop Ray fucking Lewis" when amongst the guys.

*****

The next morning Rachel, Claire, and I headed down to the beach around 11:00. Emily had drank more than the rest of us the night before and needed to sleep a little later. As we left she told us she'd be down after she showered and got ready. So we headed out with our towels, wraps, and a small cooler. We had only brought a pitcher of margaritas down to the beach with us, and we knew it wouldn't last for more than a few hours. We planned this on purpose so that at about 2 or 3 o'clock it would force us to come back up to the condo. That way, we would avoid drinking too much and prevent serious sunburns the first day.

The next thing we know it was around noon, and Emily appears on the horizon walking towards us; however, she wasn't alone. Trailing right behind her were four guys. Another thing I immediately noticed was that two guys had large coolers hoisted up on their shoulders. They were all skinny, very pasty, and had crew cuts, but overall they were pretty cute. It was fairly easy to comprehend why these guys decided to follow Emily. Her breasts were overflowing in her top. Not only was there a massive line of cleavage, but base string was so stretched that her tits were coming out the bottom.

I looked at my own suit and considered myself downright Puritanical. But then I did a quick look down, and I could see that I had two things to be proud of. "I have nice tits" I affirmed to myself. After a few more seconds of admiration, I also noticed my nipples were saying hello. Between the immediate effects of the tequila in the two margaritas and the boys, I was getting a little turned on. For a split second I felt a strong stirring in all my right places. I could feel the pressure of the sand pushing up between my legs and the cool breeze blowing across exposed skin...and it made me quiver.

Emily got up to us, unfurled her towel, and sat down. She introduced us to the guys: Ryan, Matt, Andy, and Will. They all turned out to be Coast Guard guys who all had a weekend's leave. "Hey, Will is Jamie's boyfriend's name," Claire exclaimed. Emily and Rachel shot her a cold glance. They didn't want to scare away the cute guys who obviously seemed nice enough at first meeting. I didn't care, I was kinda glad that that was out in the open. The comment did attract Will's attention. He laughed and told us that with a name that great he must be some guy.

Then Will did something unexpected. He took off his shirt, as would be expected. Then, the next article to go were his tearaway basketball warm up pants—the kinds with the snaps on the side. Underneath, he was rocking a Euro-style brief bathing suit. It wasn't a full speedo, but they were tight, very short, and neon orange. "Lifeguard On Duty Ladies!" he yelled. All of us immediately both laughed and began to wonder what we had gotten ourselves into.

Immediately, Claire went back to her book as the guys unpacked their stuff. I noticed Emily and Rachel begin assessing the guys. Even though they both had boyfriends, I knew they weren't going to pass up the chance to check out the items on display. As I was passing judgment on them in my mind, I found my eyes going back to Will. More specifically, I went back to checking out the package. It takes a pretty confident guy to rock something like the banana boat. To be honest, I thought he was pulling it off pretty well.

A few minutes later, Ryan asked Emily if she wanted to be his partner in a game of cornhole. She quickly jumped at the chance. Will approached me and asked if I would be his partner. "I have no idea how to play," was all I could reply.

"It's easy. There's two boards ten yards apart. You take a bean bag and try to throw it on the board. Also on the board is a hole, and if you make it in the hole you get extra points."

"Easy enough. Sure, I'm in," I said. Right after I said it I gave him both my hands to help me up. He pulled me up so hard that I launched into him. We did a chest bump, and I rolled down chest-to-chest. For me, it was like it was slow motion. I waited a fraction of second to break away from our contact, then I took a step back. If I was only a little turned on before, I was moving right along to getting positively riled up.

I was a little disappointed when I found out partners played opposite one another. Will was pretty far away. The largest consolation was that he had to look at me the whole time. And look he did. Even though I was standing next to Emily, Will didn't take his eyes off me. There were a lot of distractions too. Emily bounced up and down whenever she came close to the board flailing her tits around. I took a serious approach and found my groove. Will and I won 21-3. We destroyed them. Will came up and gave be a big hug. I could feel his thinly covered manhood right against my bare belly and it felt wonderful.

At that point, the girls realized that our small store of margs was done. I was a little annoyed at the thought of going back up. I was having a good time! Then the boys came to the rescue. Will opened the cooler he had brought with him and inside was everything a local bar would have: tequila, rum, beer, mixers, you name it. Claire and Rachel decided to pack it up and head back as scheduled. Matt and Andy followed them. Emily and I decided to accept a drink and another game.

Will poured me a drink, and after the first sip I knew it was strong. I mean strong strong. Even though I could tell he'd done everything you can do to try to cover up the taste of tequila, the fact that I tasted it was saying a lot. I immediately chugged it, spiked the cup, and yelled, "I'm on fucking vacation, let's get it on!" Emily shot me a surprised glance and then downed her drink. The ball was officially rolling.

*****

About two hours (and four strong drinks) later it was around 5 o'clock and we were drunk! And the best thing for me was that it wasn't sloppy drunk, we all seemed to be in the zone without getting stupid. Don't let me fool you, our inhibitions were obviously coming down. The first evidence of that came from Emily. No surprise from that tease. She was now standing next to Ryan and tossing the bags. Then, for the first time of the day, she threw one right in the hole. Everyone clapped for her. She was jumping up and down and shaking her tits like a stripper. In the middle of her celebration Ryan gave her a football style ass slap with a big "Atta girl!" No one batted an eye.

After the ass slap, Emily really put some effort into the shake and directed it right at Ryan. I didn't think her top could hold, and it didn't. Her left boob flew out and said hello to the sunshine and all of us. I was amazed at how firm and how little her boob sagged. Her perfect, nickel-sized pink nipple was a foot away from Ryan and he seemed in awe. She slowly and unabashedly slipped it back in as the game continued.

A few shots later, my team was pretty close to winning the game. My head was cloudy in a good way from the alcohol and my body was tingly from the whole day. I stood, and with as much concentration as I could muster let a throw fly. In the hole. Ringer. For the win. Tying it at three matches a piece. I threw my hands up in celebration and gave my best Emily impression of the titty shake. Then I did something pretty brash. I stuck my ass out for Will, and waited. He didn't give me the slap I wanted, so I heckled him, "Come on, Emily got the ass slap!" Will hesitated and then gave me a small one. I barely felt it.

Ryan booed. "You can do better than that," I heard from the other side.

Will gave me one a little harder...still pathetic and to more boos.

I wanted him to feel me! And more importantly I wanted to feel him! Utterly emboldened by the alcohol, I took the back of my bottoms, hiked them up, and gave myself a huge wedgie. It wasn't difficult; the material of my bottoms was pretty thin. It went right up by ass crack, exposing both my cheeks.

"I know you can do better than that! I want to see a handprint on my ass!" I yelled.

Will looked really surprised, then reared back and walloped me. "Ahhhh!!" I gave out a hugely sexual cry, and finished it with, "cause you know I'm a bad girl!"

The sting going through my body was like jumpstart. I felt everything, and everything felt amazing. The sand in my toes, my bottoms buried in my ass (and my pussy), the panels on my top gently rubbing against my nipples. All of this was happening while I was still doing my stripper titty shake. The whole experience was one huge synergy of sensuality.

While I was turned around to show Will, Ryan, and Emily the red handprint on my ass, I looked down at my front that they couldn't see. What I saw were my rock hard nipples. I thought that alone was a little scandalous. THEN, I looked even farther down. In my quick scramble to give myself a wedgie, I had really tugged on my bottoms. So much so that a lot of the material buried itself in my pussy lips. I quickly noticed that my left pussy lip was exposed, and what little the thin material continued to cover provided a perfect outline for the shape of the rest of my pussy. It was the most obvious cameltoe imaginable.

With that realization another zap went through my body. "Ah! This is so slutty!" I realized. If I turn around now, then a guy I met only a few hours ago will practically and partially see me naked. And I have a boyfriend at home!

For some reason, my mind went back to a few days ago to the office where I was tired and frustrated with work. All the pent up stress and fatigue melted away. More than that, I was really wet now. Shivers were going up my spine. My clit (that I could now see poking at my bottoms) was throbbing. I realized that in the span of last twenty seconds I had relieved more stress and was more sexually turned on than ever before in my life. This quasi orgasmic feeling was only heightened by the anticipation of what my own mind would decide to do next. "Why does it only have to last twenty seconds?" I thought.

"Uh, you slut," was going through my mind when I turned around. I hadn't changed a thing. Nipples: really showing. Bikini Bottoms: now a thong. Ass: free to see. Pussy: one lip out and counting. The whole group's attention was right on me. Without batting an eye I soaked it in. In my whole sheltered life in private schools and at an Ivy, I had never just hung my body out like this before.

Ryan's eyes feasted on me. I could trace his eyeline to all the things I noticed. First, he ogled my nipples. Next, he noticed my pussy half hanging out. After that, his mouth was whole open in shock!

And he wasn't the only one doing the looking. Will was still wearing his tight little bathing suit. All day I had just been able to pick out the bulge of his cock. After my little show the individual bits were much more recognizable. I could clearly see the shafting running down to the head.

Another zap. Immediately, it monopolized my mind. "God, look at that cock. I want that pounding inside me right now," I thought. "No, you can't do something that slutty," I had to say to myself.

*****

Attention turned back to Game 7, the Championship. That is to say most of the attention. Will still stared at me when he could turn. Ryan kept obvious and continuous eye contact on me. Emily, I feared, had abandoned me in the quest to tease the boys. I realized that she had probably meant to show them her boob, but that was it. That's where she drew the line. She kept rearranging her suit trying to give me "subtle" hints that you could see half my pussy. I didn't care. That same pussy was absolutely leaking with arousal.