The Proposition

Making the Deal

I have been rather successful in life thus far. Shortly after graduating from high school, I had started an internet dating site as a hobby. For some reason that little hobby turned into a very lucrative business. Though I struggled to make ends meet the first year my site was in business, it took off like a rocket after that. Over the next few years, my hobby provided me with a very comfortable living.

About five years ago, a major internet player made me an offer for my dating site. I couldn’t refuse. Their agent told me they could grow my site even more and offered me one hundred million dollars for it. Of course, I accepted their offer on the spot.

With the proceeds of the sale of my dating site, I bought a large house on several acres of land. It was located about two blocks from the local high school. It was also only a few more blocks in the opposite direction to the community college. Part of the allure of that location was that it afforded me the opportunity to watch the young people, especially young women, parading past my home after their high school and college classes.

The first year following the buy-out of my dating site, in addition to my home and its property, I bought many high powered toys. A speed boat, several high performance cars, including a ’63 split window Corvette, and a small plane. I made no attempt at concealing my wealth. Though I was friendly enough, I didn’t care what others thought of me or my lifestyle.

Now, at forty-two years of age, I am quite well off. I haven’t needed to work in years. I spend my time playing with my high-powered toys and tending to the landscaping of my large yard. I can easily afford a grounds keeper, but I enjoy the exercise. The work has the side benefit of keeping me in reasonably good physical condition.

One hot summer afternoon, I had been using my lawn tractor to mow the grass. One of the lovely young women I recognized as a high school student waved at me from the sidewalk in front of my home. When I waved back, she beckoned me over to were she was standing.

As I approached her, I took the opportunity to check her out. She stood about 5 feet 5 inches with a slender build. She may have weighed 120 pounds. She had long shiny blond hair pulled back into a ponytail and a cute round face. She was wearing a dark blue skirt that snugly wrapped around her hips and butt. It came to just below her knees. One of the things I noticed about her was her chest. She had on a white blouse that did little to hide the cleavage of her ample breasts. The two top buttons of her blouse were open and offered a nice view of that cleavage. As I approached she smiled broadly. Her bright blue eyes seemed to sparkle.

I spoke first. “Hi! Can I help you, Miss?”

She tentatively replied, “I don’t know.” She seemed nervous and unsure of herself.

I waited patiently as she hesitated. She bit her lower lip for a few seconds then began to speak. “Actually, I do know. I’m just nervous and don’t know how to tell you what I want. No, what I need. Please be patient with me.”

“It’s alright. Take your time. I’m in no hurry.” I tried to calm her.

She eventually began to speak again. Her nervousness caused her to stuttered as she spoke. “I need your help, and I don’t now how to ask for it. I’ve never had to ask anyone for something like this.”

I held out my hand and said, “Miss, my name is James Hunt. Most people call me Jim. If you’re going to ask for a favor, you should probably know my name.”

The nervous teen took my hand and smiled.

I could feel her hand trembling. I noticed a bead of sweat slide down from her throat and disappear between her breasts. I smiled back at her and offered a suggestion. “Would you like to come inside and have a glass of iced tea or something. That may help you get out what you want to say to me.” I continued, “Besides, it is hot today and I need a break from the sun.”

The young lady tentatively shook my hand. “I’m Jenny Atkins. A glass of tea would be nice, if you don’t mind.”

I left the mower where it was and led Jenny up the driveway to my front door. She seemed to be deep in thought as we made our way up the drive. She never said a word as we walked. I too remained silent. That silence allowed her to work out what she wanted to say without interrupting her thoughts.

Once inside, I pointed her to my couch while I got us each a glass of iced tea. When I returned, Jenny still looked like she was about to loose her composure. Sipping her tea appeared to help her relax just a little.

I broke the ice by asking a few simple questions. “Jenny, how old are you, darling?”

She replied, “I’ll be nineteen in November, Sir.”

“It’s Jim remember? Do you attend the local college?” I asked.

“No Jim, not yet. That is part of my problem.”

“Well, why don’t you tell me all about it. Maybe there is something I can do to help.”

“Okay, I’ll try. You see, my parents were killed in a house fire last spring. I have no other family and very few possessions. I have been staying with some friends since then so I could finish high school. I have earned excellent grades in high school, and I had planned on going to the nearby community college. I had won a scholarship provided by a small company here in town. They were going to pay for everything including my tuition, books, lab fees, dorm fees, and even my meal ticket. Unfortunately, due to the poor economy, that company has fallen on hard times and has informed me that they can no longer afford to fund my scholarship. The new semester starts in a few weeks, and unless I find a new source of funding, I will be unable to go to college.” Jenny paused to take a sip of tea and a deep breath.

I took the opportunity to ask her a couple of questions. “So Jenny, how can I be of assistance to you? Do you want a loan from me to cover your expenses?”

“No Sir, I mean Jim. I had another idea in mind. I don’t think I could ever repay such a large loan. College is so expensive. So, I have a proposition for you. I know you are single and live here alone. If your interested, I would be willing to trade my services for your financial help. I can cook and clean for you and do anything else you may need me to do around here.”

“Humm, that does sound interesting, Jenny. It has been a long long time since this house and I have seen such a lovely young lady like you hanging around.”

Jenny began to smile. “Jim, would you be willing to help me out?”

I replied, “I don’t know, Jenny. You are right. College is terribly expensive. I would require a great deal from you in exchange for your college expenses. I am agreeable to paying for your entire education. However, you will need to provide much more than maid and cook services.”

A look of concern came over Jenny’s face. “What else would you want me to do, Jim?”

“I think we need to discuss this proposition of yours over dinner. Jenny, would you like to have dinner with me here tonight?”

She hesitated briefly. A smile began to spread on her face. Jenny silently nodded her acceptance of my invitation.

“Very well! I need to put the lawn mower away and take a shower before I prepare dinner. You go home and get ready. Be back at about six o’clock, and I’ll grill a couple of steaks for us.

Jenny was punctual. She knocked on my door at a few minutes before six o’clock. I was impressed when I opened the door for her. Jenny was freshly showered, and she smelled delicious. Her hair was no longer in a pony tail but had been brushed out. It fell softly over her shoulders. Her blouse again had the top two buttons open and gave a strong hint of the ample size of her breasts. Her skirt snugly fit over her firm looking butt and swayed as she walked. Her skirt came down to a couple of inches above her knees.

“Jenny, you look delightful and smell delicious. I will enjoy having you as my dinner guest tonight.”

Jenny smiled and said, “Thank you, Jim. Since I am asking a lot, I wanted to look my best for you. I also borrowed my friends Obsession perfume since you invited me here for a dinner date.”

I led her to the dining room table and pulled out her chair as she sat down. I poured us each a glass of wine before excusing myself to bring our steaks in from the grill. I also served a tossed salad and had deep fried some French Fries.

I think Jenny was duly impressed. We chatted for a while about her high school grades. She had even brought a copy of her high school transcripts. Her grades were excellent. She had received almost all As. Next we discussed her goals for college. She had hopes of becoming pediatric nurse.

As we finished our dinner, the conversation turned to a more serious topic. “Jim, if you agree to help me with my college expenses, what would you expect me to do in addition to the normal household chores?”

“First, I’d expect you to maintain good grades. I think you are smart enough to figure out the rest of my requirements, Jenny. I can hire people to do the mundane things such as cooking and cleaning for a lot less than the cost of a college education. I am a single man living alone in this big house. I have all kinds of toys to play with. Unfortunately, I don’t have anyone to join me when I play with them.”

“Is that all?” She asked.

“No, Jenny. I guess I must be blunt. I will expect you to play with me as well.”

“I don’t understand. How would you want me to play with you?”

I sighed. “Jenny, how many boyfriends have you had during high school?”

“Just one during my Senior year. Why?”

“Again, I must be blunt. Are you a virgin?”

Jenny gasped in shock at such a personal question. She lowered her head in embarrassment.

“Raise your head and look at me Jenny. Please answer the question.”

She lifted her head and looked into my eyes. She was blushing. She then quietly answered my question. “Yes I am! I’ve never done anything sexual. Why?”

“Well, if we do this, I would like for you to move in here with me. I will pay all of your college and associated expenses. I will also give you a nice allowance on top of your expenses. However, I will expect you to do more than the housework. So there is no misunderstanding, I will be as plain as I can be. I will expect you to share my bed. You will do any intimate thing I ask of you. I am not a nut case, and I will not intentionally hurt you. I just expect to get a decent return on my investment. You, will effectively be my personal prostitute. At this time, you may simply refuse and walk out the door with no strings attached.” I paused briefly to give her a chance to think about my proposition. “So, what do you think of my offer, Jenny?”

“I don’t know, Jim. Can I have a little time to think about it?” Jenny asked.

“Of course you may. I need to go to my office up stairs for a little while. I’ll be there for about an hour. If you are still here when I come down, I will assume you have accepted my offer. If your gone, neither of us will have lost much.”

With that, I stood, kissed her on the forehead, and left Jenny at the table. She appeared to be deep in thought.

Jenny Accepts the Deal

When I returned from my office, I found Jenny wiping off the dining-room table. She had already loaded the dishes into the dish washer and cleaned the kitchen counters. When she heard me enter the dinning room, Jenny turned and smiled broadly. She had opened two more blouse buttons. “Jim, I am still very nervous and a little scared, but I accept your generous offer. It seems to me that most women give up their bodies for a lot less than a good education. I think this will be a good bargain for both of us. I hope you will be pleased with me.”

I stepped up to her and pulled her into my embrace. “Jenny, I am certain I will appreciate all of your efforts.” I gently kissed her lips. She was trembling as she tentatively returned the kiss.

I asked, “Are you ready to move in tonight?”

With only a slight hesitation, Jenny replied. “Yes. If you will drive me to my friend’s home, I’ll get my things.”

Jenny Moves In

It didn’t take Jenny long to gather her meager personal belongings at her friend’s home. She only had a few toiletries, some make-up, and a hand full of clothes.

When I saw her granny style nightgown and underwear I held them up and said to her. “These will never do! We will go shopping for a few things before we head home.”

Her friends wished her well as we left. They were happy Jenny’s hard work in high school would be paying off for her. They were excited she would be going to college after all.

Luckily, it was a Saturday evening and the local mall was open a little later than it would have been during the week. I took Jenny straight to the upscale Belk’s department store.

Jenny was like a kid in a candy store. We picked out several dresses and blouse/pants combinations for her. The dresses were all rather short. Her legs would be exposed from several inches above her knees. The dresses and blouses would all provide a nice view of her cleavage.

At first, Jenny was a bit nervous over the exposure of her legs and breasts that her new clothes would give. “Jim, everyone can see my boobs in these tops.”

I smiled and responded to her. “Exactly! I will enjoy seeing your beauty on display for me. We will also get you some more conservative outfits before your college classes start.”

After a while, she relaxed and simply smiled when I appreciatively looked at her chest as she tried on her new clothes. We then went to the lingerie department. There we picked out several pairs of panties and bras. Most of her panties were French cut while a few were thongs. Her bras were all C-cup push-up or shelf style. My mouth was watering over the anticipation of seeing Jenny wearing her new lingerie.

We then picked out a couple of nightgowns for her. One was a long, silky, deep blue, full length gown. I thought it brought out the blue of her eyes. She also picked out a similar gown in white. Both gowns tended to cling nicely to her figure.

Lastly, we bought Jenny a pale blue baby doll nightie. It was thin enough that it would hide very little of her lovely young body.

Jenny blushed again when I held it up for her approval.

“Jenny, you will look fantastic in this.” I told the blushing girl.

“If you think so, Jim. I’ve never worn anything like that, but if you want me to, I’ll wear it for you.”

Before we headed for the check-out lanes, we stopped by the cosmetics department. I picked up her own bottle of Obsession. Several hundred dollars later, Jenny and I were heading toward my car. We were both loaded down with bags of clothing and accessories. She was hanging on my arm as we made our way across the parking lot.

Once in my car, Jenny scooted close and kissed my cheek. “Jim, I will do my very best to make the cost of my education a good bargain for you.”

I turned toward her and gently kissed Jenny’s willing lips. “I am sure you will, Jenny.” I then drove home with Jenny sitting very close to my side. Upon arrival, we carried her bags in and sat them on the dinning room table.

Jenny tentatively asked, “Jim, where would you like me to put my things?” Her shaky voice indicated she was as nervous as she had been when she first asked for my financial help.

I took her into my arms and hugged her firmly. I kissed her gently then said, “Jenny, there are four bedrooms and two full baths upstairs. One of the bedrooms is my office, another will be converted into a study in which you can do your school work. The master bedroom with an attached bath is mine and is the largest room up there. It has a large walk-on closet. The forth one can be yours if you want it. I suggest you put your things where you will want to be spending most of your nights.” I intentionally left the choice of rooms up to her.

Jenny gathered several of her bags and headed up the stairs. I watched her backside as she climbed the steps. I especially like the way her butt swayed with each step she took. It made her skirt sway back and forth as it followed her hips.

After she made her final trip with the bags, she seemed to take longer to return. I figured she was just putting her things away.

Jenny Honors Her End of the Bargain

My mouth fell agape. Jenny floated down the stairs in her white gown. It was held up by two thin straps over her shoulders and softly clung to her shapely body from her chest to her hips. The lower half seemed to hug her legs and float behind her as she walked. Her aroused nipples protruded against the silky material of the gown. Jenny was a vision of beauty and innocence. She came forward and stood just a few feet in front of me.

Neither of us said a word for a few moments. I merely stared and took in her beauty. She smiled nervously.

I finally regained my composure and asked her, “Jenny, I have never seen such a beautiful young woman. Where did you put….”

“Jim, you have a wonderful walk-in closet in the master bedroom. I hope I haven’t taken too much room in it. You have already been so kind to me. I just had to put my things in the master bedroom. I want to start honoring our bargain right away. That is why I wore this white gown.”

“Take all the room you need. Now come here.”

Jenny stepped up to me. I wrapped my arms around her waist and pulled her body snugly against mine. She placed her arms around my shoulders. As I hugged the trembling teen, I could smell her new perfume. She again smelled delicious. I kissed her neck and said, “Humm, Jenny you smell good enough to eat.”

As I kissed her neck, I let my hands slip down her back until I held a firm ass cheek in each hand. I squeezed both at the same time.

She moaned and pressed her body closer.

“Jenny, would you like a glass of wine before we retire?”

“No Jim. To be as blunt with you as you have been with me, I intend to start honoring my end of the bargain tonight. Since it will be my first time I know it will hurt, but that is part of it. I don’t want anything to dull my senses when you take my virginity. I want to remember every moment of our first night together. Can we go to bed now?”

“Yes darling, and I promise to be as gentle as I can with you.”

We then slowly walked up the stairs arm in arm. She stopped at the door to the master bedroom. I looked at her somewhat confused.

“Jim, I know we are not married. This is not a honeymoon, but it will still be my first time doing anything like this. That’s why I’m wearing my white gown. Would you please carry me to your bed?”

I smiled and scooped her up into my arms. With her arms around my neck we kissed tenderly. She was smiling broadly as I easily carried her to my king sized bed. It would soon become our bed. I gently laid Jenny down on her back and stood up. As I kicked off my shoes, I said to the young beauty in my bed, “Jenny, you are so beautiful. I hope I can make your stay here as pleasurable for you as I believe it will be for me.”

She smiled up at me.

I looked down upon Jenny as I began to undress. Her eyes followed my hands as I unbuttoned and removed my shirt and tossed it to a nearby chair. Her eyes opened a little wider as I released my belt, unhooked my waist button, and lowered my zipper. As my pants fell to the floor, Jenny’s eyes focused on the bulge in my boxers.

I stepped out of my pants and lowered my boxers. My erect cock stood proudly at attention. At seven inches in length and a bit on the thick side in girth, my manhood is only a bit larger the average. It must have impressed Jenny. She gasped and her eyes widened when she got her first look at my hard cock. I could see the look of fear in her eyes.

In a shaky voice, Jenny reacted to the sight of my ridged member. “My God, Jim! It’s so big!”

I smiled down at her and replied, “It’s not much bigger than the average guy. Don’t worry. It will fit inside you, and I think it will give you as much pleasure as you will me.”

I then laid on the bed next to Jenny and began caressing her lips with tender kisses. Jenny’s lips parted and our tongues fought a mock battle as our ardor rose higher and higher.

Jenny was smiling as I slipped the thin straps of her gown off her shoulders. As I pulled the straps down, she pulled her arms out of them. I then pulled her gown down until her breasts were fully exposed.

“You have a beautiful set of tits, Jenny.”

Jenny smiled broadly. She began breathing heavily as I kissed all over her face and ears, around her neck and throat, and both shoulders. My hands gently caressed her breasts. I slowly kissed my way down her chest until I reached the upper slopes of her tits. I kissed and licked all over her breasts while avoiding her nipples.

Jenny had continued breathing heavily. As I sucked her right nipple into my mouth Jenny gasped then breathlessly moaned. “Oh Jim.” She brought her hands up and pressed on the back of my head. My lips were pressed tightly to her breast and its nipple. She moaned again as I licked and sucked her hardening nipple. I soon switched breasts and sucked on her left nipple until it was as hard as the right side.

“Oh Jim, I am so ready to give myself to you. I have never felt as aroused as I do right now.” She cooed.

Jenny lifted her back as I pushed her gown further down until it was bunched around her waist. I kissed my way down her smooth soft belly. She giggled when I delved my tongue into her belly-button.

She took in a sudden and deep breath. “That tickles.”

She gasped again when I began gently stroking her virginal pubic hair like it was a beloved pet. She seemed to have forgotten to put on her panties. Though she was trembling nervously, Jenny slowly spread her legs to give me greater access to her moist intimate lips.

“Oh God Jim, you have me shaking with excitement. Please be gentle with me down there.”

“I will Baby. Just try to relax as much as possible.”

She spread her legs as much as she could when I slid further down and lay my body between them. My face was merely a couple of inches from her virgin pussy.

She looked and smelled delicious. I was anxious to taste her treasures. I pushed her legs up until her knees were near her chest. Even though her nether lips were snugly closed, her feminine aroma beckoned me take a taste of her treats.

Jenny seemed to freeze when I gave her one long pussy-lip parting lick from just above her tight little asshole to her clit. She gasped when I flicked her clit with my tongue. She cried out, “Oh my God, Jim!”

I continued licking all over her virgin femininity. I sucked her clit into my mouth and repeatedly flicked it with the tip of my tongue. Jenny exploded in orgasm. Her hips bucked almost violently.

Without lowering her knees, she grabbed the back of my head and pressed my face firmly into her awakening pussy. She cried out and rocked her hips to encourage my oral attentions. “Oh yes, Jim. Oh God, right there!”

I sucked and licked her clit as Jenny bucked her way through another orgasm.

Jenny’s breathing slowly calmed and she lowered her knees. “Oh my God, Jim. That was so fantastic. I’ve never felt anything even close to that.”

As she continued to calm and her breathing returned to near normal, I crawled out from between her legs and laid next to her. As I resumed gently stroking her pussy with my fingers, I told her. “Jenny, there’s nothing so erotic as the taste and aroma of a teen’s fresh virgin pussy.

Jenny hugged me tightly and cooed, “Oh Jim. Thank you. I’m glad you like me.” She was practically flooded with her personal lubricant as I carefully fingered her tight hole. Jenny was soon rocking her pelvis and cooing into my ear.

“Jim, are you going to take me now?” Her nervousness was edging back.

“Yes, Baby. Are you ready?”

She replied apprehensively, “I think so.”

“It’ll be alright. I promise to be as gentle as I can, but it will probably hurt when I take your cherry.”

“I know. Let’s just get it over with, please.” Jenny was resolute in her decision to give me her body in exchange for a college education.

Jenny spread her legs as I rolled onto her body. It surprised her when instead of pushing my cock into her right away, I kissed my way down her body again. She was soon gasping for breath as I again ate her juicy virginal pussy.

She seemed to be nearing another orgasm when I crawled up her body and placed my cock into her opening. I pushed the head of my cock into her and felt her lips spread to accept my cock.

She gasped. “Umph! It’s so big. Are you sure it will fit in me?”

“Yes Baby, it will fit. Try to relax.”

I pushed again and felt my cock’s head bump into her resistance. Her hymen, which had guarded her inner treasures for nineteen years, had but a few more seconds to survive.

I gave her a few shallow strokes bumping into her hymen each time. It seemed to be one of the tougher kind. I told Jenny it was time. “Honey, hold on. The pain may be sharp but it will not last too long.”

“I know. Go ahead. Please take me.”

I firmly kissed her lips and hugged her tightly. With a very firm shove, I fully entered Jenny’s virgin pussy. She cried out loudly in pain and gasped for breath. Her hymen had been ripped open but not without causing her considerable pain.

I held her tightly with my cock still fully imbedded in her devirginated pussy. My cock’s head was pressed firmly against her cervix. I could feel the warmth of her virgin blood coating my cock. Tears were flowing from her closed eyes. I whispered in her ear, “I’m sorry I hurt you so badly, Jenny.”

“I know, Jim. It had to be done eventually. Please lay still for a bit so I can get used to you being inside me.”

I, of course, did as she requested and lay still with my cock buried in her tight teen pussy. We lay quietly for several minutes while Jenny got used to my manhood filling her.

She kissed me and said, “I think you can move a little now. Easy please.”

Slowly, I began giving Jenny gentle strokes in and out of her tender pussy. Though she was still hurting, she soon started to enjoy her first fucking. She was soon rocking her pelvis and groaning with pleasure.

The tightness of Jenny’s freshly devirginated pussy and the extended time since I had enjoyed any female companionship made me ready to cum much too soon. “Baby, I’m about to cum.” I warned Jenny.

“It’s okay, Jim. You can cum in me. I’ve been on the pill since I was sixteen. Mom didn’t want any surprises while I was in high school. I’m feeling much better now. Her smile was back as well.

I increased the speed and depth of my thrusts into her tight hole. I was soon driving into her teen cunt with exuberance.

Jenny appeared to be having a good time too. She was thrusting her hips up to meet my thrusts. “Oh yes, Jim. Fuck me! Give me your cock. Let me feel your cum inside me!”

Much too soon I buried my cock in her pussy and pumped my cum into Jenny’s tight hot hole. Her cervix was bathed in its first load of cum.

At about the same time, she began thrusting her pelvis up to accept my cock deep into her core. She cried out, “Oh Jim, yes! I can feel your cum flooding into me. God, it feels so good. It’s so warm.”

About that time, we both collapsed with my cock still buried in her cunt. We lay like that until I softened and slipped out of her. I slid off her and we cuddled until we fell asleep in each others arms.

In the morning, we observed the results of the previous night’s activities. The part of her new silky white gown that had remained under her ass had a large blood stain. Jenny had bled quite a lot after losing her cherry.

“Oh Jenny, I’m afraid we’ve ruined your new gown. We’ll get you another one this afternoon.”

“No! I want to keep this one. The stain will remind me of our first night together. But what about your sheets? They’re not much better.”

“That’s okay. I have plenty of sheets and they make more every day. Now, we’re a mess. How about a shower?”

“Jim, maybe we can make things a little messier before we get in the shower. I’d really like to feel you inside me again. This time, take me like you mean it.”

I smiled broadly as I rolled onto Jenny’s body and again shoved my hard cock deep into her pussy. I was more than happy to slide my morning hard-on into her still tender hole.

Jenny’s pussy was still tender and she groaned as I fully entered her. She immediately began thrusting up to meet my cock. As she had requested, I repeatedly slammed my cock into her tight hot cunt until I was about to cum. She grunted and groaned as her orgasm overtook her body. At about the same time, I fed her cervix its second load of cum.

We cuddled a while and dozed off again. We slept in until nearly 10:00 AM.

When we awoke again, as she rolled out of bed. Jenny asked, “After our shower, what would you like for breakfast?” She then got a pained look on her face. “Oh! Uumm, Jim, I will be happy to honor our bargain. You can have me any time you like, but if it is okay, can we do something else. I am so sore, I’m not sure I can even walk.”

She smiled but I knew she was serious. As hard as I had pushed to break her hymen, and then the pounding I had just given her pussy earlier this morning, I knew she had to be sore. “Of course we can. There are lots of things we can do until you get over your soreness.”

I took her into my arms and held her naked body tightly to my own. I kissed her and said, “Your education is going to be one of the best investments I’ve ever made.

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