Fun with the Boss

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Woman shows off in restaurant and has sex in alley.
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As agreed, I wore a sheer blouse, jacket, and short skirt with fishnet hose and garter belt, but no bra or underwear, not even a G-string. Sleeping with the boss isn't as bad as I'd thought. It turns out he's a kinky bastard. And of course, my unwarranted promotions sure help things along. Tonight he's taking me to dinner at my favorite, swanky -- and very expensive -- spot. In exchange, I've agreed to unbutton one button of my blouse before each course.

The valet parks his convertible Jaguar as we head into the restaurant. The hostess bitch checks me out. She's a smokin' hot little thing in her early twenties. An aspiring actor no doubt. We make eye contact. She smiles and I ask her for a booth. In the dim light I can't tell if her eyes are deep blue or gray. I'd like to find that out later.

She leads us to a booth. My boss and I both appreciate her slim figure as she navigates the dining room floor. We're seated. She looks back at us as she heads back to the front. I flash her a coy smile and look down at my plate.

I flirted a bit with our server. He's adorable and clearly likes my size 2 figure in this outfit. Not surprisingly we have very attentive service. We start with an expensive bottle of bubbly. I liked it. Don't remember where it was from. Don't really care. On an empty stomach it goes straight to my head.

The appetizer course comes. I undo one button at my neck. Not too exciting yet.

Next comes a light salad. I undo a second button at the neck. I'd like to speed things up, but can't because then I'd be practically nude by dessert. Hmm, maybe not such a bad idea. My boss answers e-mails on his Blackberry between courses. I track the hostess as she covers the room seating more customers.

By the pasta course the wine is beginning to kick in and I not only unbutton the third button but also open up the blouse a bit, providing a nice view of the tops of my breasts and ample cleavage. Still a PG-13 view, but damn hot if I do say so myself. We have some kind of red wine next. Expensive and high in alcohol, I like it.

Most of the other diners are too engrossed in their meals and conversation to notice me. But the server and busboys clearly appreciate the view. This excites me. Emboldened by the wine and adrenaline I reach down, pull up my skirt, and lightly finger my clit. The tablecloth hides my hand as I spread my legs further apart to gain better access and to arouse my partner. As we agreed, my boss can't touch me in the restaurant. So he watches but doesn't yet touch.

Before the main course I undo another button and further re-arrange my blouse. The wine is really getting to me now. And I feel a rush from showing off. I love to drive guys crazy with my body. My 38D breasts and thin waist. My legs toned from hours on the treadmill. My long, silky blonde hair.

Now my entire cleavage is exposed. The inside portion of both my ample breasts is fully visible. Not an unusual look for fashion model photo shoots, but pretty unusual for a restaurant, even in West Hollywood. I'm really enjoying this. So I decide to go for it and visit the restroom.

A number of the other customers definitely notice as I proudly walk across the room with the girls on -- almost -- full display. I'm tempted to go into the men's room to put on a show for whatever lucky guys were in there. But that would be a little too obvious (and would almost certainly get me thrown out). Instead, I go into the ladies room and go into a stall. I decide to finish the job I started at the table and spread my legs and begin masturbating, thinking of the men who have been viewing my wonderful body. Nice.

Next I fantasize about seducing the hot hostess. Pulling her close and kissing her deeply. Felling her resist at first as our bodies touch and my hands explores her small, pert breast, her taught thigh. Then feeling her muscles loosen as she melts into my arms. Just then, a noise startles me out of my trance.

Whether accidentally or unconsciously, I left the stall door unlocked. An attractive redhead opens the stall door and sees me, legs spread wide, blouse open, one hand rubbing my clit, and the other squeezing my breast.

"Oh, sorry," she says.

"No problem. Join me if you'd like."

She smiles and closes the door, but not after letting her gaze linger on my body for a few seconds. Embarrassed and turned on at the same time, I quickly put myself together while she is in the other stall and head back out into the dining room.

Before dessert I undo one final button and rearrange my blouse again. It is a little more difficult to show skin without freeing the girls completely. Maybe I should have brought some of that tape used by the beauty pageant contestants. Oh well. It's not that hard to keep things under control.

We finish the meal and the last of the wine and head out. Back at the valet station the night air feels good against my chest, which is still very exposed. The valet captain looks bored. So I absentmindedly brush one side of my blouse aside, revealing one of my full ripe breasts. His eyes nearly pop out of his head with surprise. He tries to not to stare but continues to steal glances back at my chest. Seeing this, my boss realizes I'm ready for something a little more daring. He seems pleased, finally focusing his full attention on me.

We drive a few blocks to a light industrial area that is busy during the day but mostly dead at night, especially this late. My boss parks the car, gets a coat out of the trunk, and walks to my side of the car, handing it to me.

"Strip off your blouse and skirt," he barks at me. "And put on the coat."

I happily comply, giving him quite a show in the process. I leave my clothes in the car and put on the coat as I step out of the car. We walk to a corner. I clutch the coat and look around.

"Hand me the coat," my boss says in his commanding voice.

Exhilarated (and still very horny) but nervous, I do it. I'm left standing essentially naked. The first time I've been completely naked in public. I like it. I strut down the street about ten paces and them come back. I repeat this several times, growing bolder and walking farther each time. The final time I see car headlights in the distance.

I wait for them to come closer. I'm excited by the prospect of someone seeing me completely nude. But my boss gets nervous, covers me with the coat, and hustles me back to the car, muttering something about cops. We head off again.

In the car, I realized I looked like a streetwalker. Fuck-me shoes. Sluttish hose with a garter belt. And nothing but a faux fur coat on top. Like I said, my boss is kinky. I decided I could definitely go with the streetwalker fantasy. Let's say he'd just picked me up and we were looking for a spot for some luvin'.

"How about that alley, sugar," I purred in an admittedly-cheesy fake accent. "Take care of me and I'll do you right."

He smiled and pulled down the alley. We both got out of the car. I unbuttoned my coat and walked up to him.

"What do you want sugar, a blow job? Half and half?"

"Yeah, half and half."

"Sure thing, sugar. That'll be a hundred." I reached down and began stroking his cock through his trousers. It was already nice and firm. A bit of pre-cum stained his trousers.

He smiled a little. I guessed right as to his fantasy. He seemed to like me running with it. He pulled out his wallet and handed me three fifty-dollar bills.

"Ooh. Thanks. I really LIKE you." I began to unbuckle his belt as I gave him a long, deep kiss and pushed him up against the wall.

I dropped to my knees and unzipped his trousers, letting them drop. I decided to tease him a bit before pulling down his briefs. The outline of his hard cock was clearly visible through the thin fabric. I used the tip of my tongue to tease the head. He moaned with pleasure. I loved the salty taste of his pre-cum. I continued flitting my tongue down his shaft and back again.

Finally, I slid my fingers under his waistband and pulled the briefs out and over his cock. I slowly pulled them down, freeing his cock to swing forward. He grabbed the back of my head and pulled me onto it.

"Suck it whore," my boss said. "Take in every inch."

He was really getting into this. And he was doing most of the work. I let him fuck my mouth and concentrated on not gagging. I gently fondled his balls with one hand and kept the other up on his hip in case I needed to push him away. He continued to moan with satisfaction. At this point, I had no idea if we had an audience or not.

I wondered if he'd forget to fuck me and just cum down my throat. But after several minutes, he pulled out of my mouth, pulled me onto my feet, spun me around, and pulled the coat from my shoulders. I now I could see that we did have a small audience. He pushed me against the wall and spread my legs. He thrust his cock into me.

"Filthy slut," he said breathlessly. "I bought you. You're mine. Now I'm going to cum deep in you." I was so turned on by our audience that I was oblivious to his roughness. I was almost disappointed when he ejaculated inside me after just over a dozen thrusts.

Once he came he quickly pulled up his pants and prepared to go. But I didn't want it to end. I picked up the coat but didn't put it on. Our audience was further down the alley and not clearly visible in the dark. I wondered if any of them were cute. I walked in that direction as my boss' cum dripped down my leg.

My boss started the car. "Let's go," he yelled. I briefly toyed with the idea of staying here and playing out my role as a streetwalker. Seeing how many tricks I could turn that evening. Seeing how much I could make selling my body. But that was just a fantasy. I wouldn't last out here alone. I swung the coat over my shoulder and proudly walked back to my boss' car. Hopefully at least a few more guys, or girls, would see me before we got back to my place.

My boss seemed a bit distant on the drive back. Hello. Hot, naked girl sitting next to you! Maybe he was a bit embarrassed that he'd shared his little fantasy with me. Did he really visit hookers? Or was it just a fantasy? Anyhow, so long as the promotions kept coming and he continued to pay for my condo what did I care? So long as he was happy. Because I certainly was.

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  • COMMENTS
3 Comments
karen90karen90almost 13 years ago
hot except for all the sexist language

Besides that it's wonderful

AnonymousAnonymousover 15 years ago
When you fuck people at work and it is related

to work you are a whore/prostitute. Being a streetwalker simply means you cant find people easily to fuck with. Your boss fucks with you and you get paid. Just a whore. When he has enough of you and lets you go. You will need money and streetwalking is already something you feel tempted to do, so it will be an easy transition for you.

AnonymousAnonymousover 15 years ago
Yikes

I think you already are a paid whore, street walking isn't far off, enjoy slut.

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