Sitter's College Fund

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College freshman gets a ride home which leads to a tip.
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This story is mostly true, though some events have been dramatisized for effect, and the names have been changed.

I grew up in Southern California in the early 80's. I guess I had a pretty typical High School experience, even though I had very little dating opportunities. I guess High School boys just did not stimulate my interest. Therefore, when I graduated at the age of 18, I had kissed a few guys and a few of them had caressed my breasts, over the shirt, but that was about it. I suppose that I could have had the opportunity to do more. Being in my late teens along with the years of horseback riding left me with a pretty athletic body. I was 5'5" and weighed about 115 pounds. I had long dark brown hair, hazel eyes, and my measurements were 34c, 25,34. Perhaps my 3.9 GPA had me labeled as a nerd or something. Oh well, their lose.

The sequence of events that lead to my first erotic encounter started on a Wednesday night when I got a call from the Smiths. They wanted me to watch their 4 year old child the next Friday afternoon. It appeared that he had some sort of Job recognition dinner to go to, not that I really cared about the reason for them wanting hire me again, I was just trying to get some spending money for college in the fall. "I will be there at 5:30", I told Mrs. Smith.

On Friday morning I got dressed in typical Southern California summer wear, a halter top, shorts and sandals. Then I caught the bus for my day job at the mall. The day was the same as always, guys would wonder around the food court, some lingering longer then appropriate to watch my work behind the counter, before coming over to place a order. What can I say, it was a job. When my shift ended at 5:00, I only had a half hour to walk the 5 blocks to the Smith's house. I got there just as they were set to leave. Mrs. Smith, Laura, was in a very nice, low cut black dress which showed off her exquisite body. I hoped that I would look that good in my late 20's. Mr. Smith, Bill, was in a suit and tie, though you could tell that it covered well maintained muscular physique. They told me that they would probably not be back till midnight. Since I knew their routine I told them not to worry about it and wished them a good night.

The evening went fine, their child was actually fun to be around. However, I was a bit tired when they showed up at 12:30. Bill was doing fine while Laura had obviously had a bit too much to drink. With a smile I wished her a good night and accepted Bill's offer to drive me home. During the 15 minute drive we engaged in the typical small talk. I turned out that the company president retired and one of the VP's move up which allowed Mr. Smith to become the newest VP.

My house had a long secluded driveway sheltered from both the road and the house. When we arrived threw the car in park and turned off the engine.

"I want to thank you again for being the best sitter we have ever found," Bill said as he handed me a crisp $100 bill.

"Wow, Mr. Smith. Seven and a half hours at $10 an hour is $75."

"Consider it a raise. I got one tonight so you should too", he replied.

"Why thank you. Let me know anytime you want my help", I reached for the door handle.

"Before you go, could I get a good night kiss?"

I was a bit shocked at the request but even more shocked at my reply. " I guess that would be ok"

Bill leaned over to me and pressed his lips against mine. As his lips parted I felt my lips also part. Then his tongue slide into my mouth, my tongue went to work caressing the invading flesh.

As he broke off the kiss his lips moved to my neck and then to my ear, his kisses sending sparks through my body. It was then that I noticed that his had had wandered onto my breast. I was about to break the contact when I heard him whisper in my ear. "I have another $200 contribution for your college fund if I can spend some time with you."

This did shock me. "I am not going to have sex with you for $200." I told him. "I may be old fashioned but I am saving myself for the right person."

"That is not what I meant. I mean, I find you extremely beautiful and I have had my fantasies, but I would not want you to do anything that made you uncomfortable. I'll tell you what, here is the $200 and you can leave whenever you want, though I would like you to stay, at least for a little bit."

So, here I am, in the front seat of a married man's car with $200 and for some reason my mouth said "ok" before my brain could protest. I mean, it's not like i'm prostituting myself because we would ot be having sex. We would only do what I would do on a typical date, well, maybe a little more. As I put my now $300 into my shorts pocket I felt Bill's arm move around my back and pull me closer to him. Again, we kissed, but this time when his hand caressed my breast, he pulled down the halter top. It was the second time that a guy had touched my bare breast, but unlike the first time, I did not take Bill's hand away. It felt wonderful having Bill caress my firm tits. I could not help but moan as Bill started kissing my neck, then slid down to kiss my breast. As he sucked my erect nipple into his mouth, he started to unbutton my shorts. That woke me out of my trance.

"No, I am not ready for that," I told him.

"Well, perhaps you would be ok with this?" he asked as he lead my hand onto his hard cock hidden beneath his pants. Again, I had a few other dates try to get me to fondle them to no avail, but this time I felt my fingers wrap around his cock and instinctively rub the length of it's 8" shaft. Bill leaned back in his seat as I did this. I got the bright idea so switch my position and turned to face him. As I leaned forward I pressed my right tit into his face. His hands squeezed my breasts as he sucked fist one, then the other into his mouth. One hand then moved down to my thin waist then down to my thigh. As he tried to slide his hand up to caress my pussy I again told him "not that".

His reply was to again suggest an alternative. Bill unbuttoned his pants and slide my hand onto his bare penis. I had never actually touched a cock before and it was a thrill to feel the hardness, heat and texture of his large cock. I could not see how putting something that large into me could be pleasurable. It actually scared me. My hand continued to caress his cock as one of his hands retuned to my breast while his other hand slid onto my back. After a few minutes of caressing him I heard his breathing start to change and felt the arm on my back start to push me downward. I realized what he wanted and started to protest, but then decided that I guess I could give him that. I adjusted my position so that I was kneeling on the passenger seat. Then I allowed him to press me downward. As my face was pressed towards his cock I opened my mouth. I was not sure what to expect as this was the first blow job I had ever attempted. As his cock slide into my mouth I decided that the best thing to do was to make my tongue and lips put as much contact onto his cock as possible. Then I started bobbing my head up and down on his hard cock. This brought even more moans from Bill. Occasionally, Bill would press my head downward, sliding his cock deep into my mouth, causing me to gag. Once, he actually pushed my head down while I was swallowing some built up saliva. This resulted in his cock sliding into my throat and somehow my lips touched his pubic hair. This surprised us both and he held me down there for a few moments. I started to run out of breath. Gasping, I pulled away from his cock.

"Don't do that again," I warned him.

"I promise I won't," he replied as he urged my head back down.

I decided that I would suck him for a few more minutes then have to call it a night. If he wanted I could rub his cock until he came. However, as I put him back into my mouth one of his hands retuned to my breast and the other went back to my head. I was about to protest again when I noticed that he was not trying to get me to go deeper, but was actually holding me still. Then he started to moan and I felt him go ridged. Suddenly, spurts of hot, salty cum started filling my mouth. While his cock was not in my throat, it was at the back of my mouth. The first spurt shot out so hard that I had no choice but to swallow. However, the rest of his cum quickly filled my mouth. Not knowing what to do and not wanting to hold it in my mouth I quickly swallowed the rest of it. It was kind of disgusting, but not as bad as I had feared it would be.

As I got up and pulled up my halter top I said good night and got out of his car. As I walk to my home I wonder if I will ever sit for the Smith's again.

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AnonymousAnonymous7 months ago

Too late for a sequel?

So authentic it’s easy to believe it actually happened. I’m sure Mr Smith gave you

another ride home so what happened then?

NaughtyMirokuNaughtyMirokuover 11 years ago
Not good enough

I know that people hate on the people who give good advice to help out the author but they take it as a person hating on the story. So for starters you really need to check your work and make sure that your spelling is better and some people like short stories but in this case you left it wide open for a sequel so this story should have been longer. So in the next chapter if there is one write a longer story and give it more detail a little something to spice things up a bit.

AnonymousAnonymousover 11 years ago
Doubting the 3.9!

You said you had a 3.9 GPA, yet I found several spelling errors! I guess that's where the 'mostly' true comes in huh?

AnonymousAnonymousover 11 years ago
Irony

After saying 3.9 GPA you spell loss wrong? Classy.

thebuffalothebuffaloover 11 years ago

That was a darned well written tale. Heck of a job! Enjoyed it thoroughly.

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