Beware of the Babysitter

This is my first attempt at writing something like this. Please let me know if it is liked and worth continuing.

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Wednesday

It had been a pleasant evening. The summer was winding down. My wife, Kate, and I had been at a party at a friend's home. We were returning home. I looked at Kate as we pulled into the driveway. What a remarkable woman. We had been married more than 15 years, but she was as beautiful as the day we met. Changed, as we all do.... a little heavier a little older, but still fit and beautiful. Short brown hair, blue eyes, beautiful breasts, and a lovely figure. What a lucky man I was.

We walked in the house and were greeted by the babysitter, Tiffany. Tiffany has been our babysitter for years now. Our children, John (12 years old) and Emily (15 years old) loved her. Tiffany had babysitted them since her freshman year in high school and has essentially become a member of our family, going on vacations with us and often times just hanging around and visiting. Tiffany was now in college, home for the summer and had volunteered to stay with the kids, even though they were getting a little old for a babysitter. My heart sank when I saw her because I realized any chance of me getting lucky tonight were gone. I had to drive Tiffany home because her car was in the shop. By the time I got back, Kate would be ready for bed and sleep -- any attempt at an amorous coupling would not be enthusiastically welcomed. Oh well, such is life.

Tiffany visited briefly with us in the kitchen. As I watched her talking with Kate, I realized just how much Tiffany had grown. She was no longer a teenager, but was now a grown woman. She had a full figure, which her jeans and white blouse did nothing to hide. Her hair, which was long and black, was pulled back. Her skin was tan from the summer sun. I bet she was driving the boys crazy at school.

On the way to her home, we talked about school, how she was doing in college and speculated on what she might do when she graduated next year. I pulled in her driveway and waited as she searched for her keys in her purse. I turned on the car's inside lights so she could see better. As she was leaning over to look in her purse, I could see down her blouse. I couldn't help but stare, not that there was much I could see, just her white bra. The next thing I know, she looks up at me and says "Mr. G, are you staring down my shirt?"

Maybe it was the couple of drinks I had earlier, or just being caught.... I don't know, but I just stammered. I could not respond. Tiffany sat back, looked at me and said "Well, you've seen mine, show me yours." What... did I hear her correctly. Tiffany must have seen the confused look on my face, because she went on "Mr. G, you saw me....now you show me your penis."

At this point, I attempted by reply: "Tiffany, that wouldn't be right......I apologize for what I did....I didn't mean....."

Tiffany responded "Mr. G, I don't care what you did or didn't mean. You were trying to look at my titties. Now open up those slacks and show me your dick, or, so help me, I will tell Mrs. G what a dirty old man you have become!" Now I was just plain taken aback, no one had talked to me that way before. I have no idea what came over me, but so help me, I started to unzip my pants. I got the zipper down, when Tiffany encouraged me, saying "Well, I'm waiting."

So I pulled it out of my boxers so Tiffany and the whole world could see. Now, at this point, I'm pretty self conscious and Mr. Happy is acting kind of shy, so now I'm thoroughly embarrassed. I can feel my cheeks reddening, when I hear "Mr. G, what a cute little dickie, but it doesn't look very excited to see me. STROKE IT FOR ME." And for whatever reason, I did.

As I'm stroking and becoming hard, I look up at Tiffany and see her sit back. "That's nice," she says, "Keep stroking...make it hard for me." Next thing I know, Tiffany is lighting up a cigarette. I've never known her to smoke and we don't let people smoke in our car. I started to say something, but she just looked and me, said "Shut up...keep stroking." And, I did.

Next Tiffany told me to "close your eyes.....think of my tits.....I want you to cum thinking of my tits." Closing my yes, stroking faster and faster, getting harder and harder, I could feel myself starting to cum as I invisioned Tiffany's breast in the bra and imagined what they looked like outside the bra. "Cum for me," she said "cum in my hand, right here." Cum I did, again and again it felt like. All in the palm of her hand. Then, as I opened my eyes, she looked at me and said "Lick it up."

"What!" I said. "Well," Tiffany impatiently continued, "I can't go in my home with your cum all over my had .... Clean my hand .... LICK IT UP!" She grabbed the back of my head and pulled it to her hand. I could see my cum, pooled in her hand, starting to run over. And I licked it. Tentatively at first. I had never tasted myself like this before. A few times I had tasted myself with Kate, either on her lips our while licking her after we had made lover. But here, it tasted strong, pungent. Tiffany encouraged me telling me "that's it...lick it up for me." And I did, with more gusto, licking her palms and fingers, until it was gone.

"Good boy, my little cum licker," she said when I was done. She gave me a peck on the cheek and then she was gone, walking up her drive to her front door. Leaving me, with my shrinking penis hanging out of my pants, my own cum on my lips, alone in the car.

Thursday

The next day, I found my self sitting at my desk, wondering just what I had done. I could not believe what had happened; I had pulled my dick and masturbated into the hand of our long time babysitter and friend... then licked her hand clean. Where was this going to lead. What would my wife, Kate, say if she found out. God, how as I going to face Tiffany again.

Well, that question was promptly answered when my phone rang and my secretary announced that Tiffany was here to see me. I almost spit out the coffee I was drinking when I heard that. Before I could stand up, Tiffany walked in my office, cheerfully greeting me "Hi Mr. G," then in an undertone "How's my little cum licker today?"

I had to put a stop to this. "Look Tiffany," I started, "I don't know what came over me last night." I went on "I'm sorry for what happened, but ...." She stopped me before I could get the next thought out.

"Mr. G, I don't have long, I just wanted to show you these and make a proposal." She then handed me a stack of printouts of pictures. The first showed me stoking my dick. The second showed me, eyes shut, stoking myself above a hand. I could recognize Tiffany's ring on the hand. The next show me cumming into the hand. The last showed my face, licking my cum from the hand.

"Cell phones are amazing things Mr. G. Mine takes pictures. These came out particularly well, considering the lighting and how fast your hand was going," she continued. "So, here is my proposal, my little cum licker: I want a slave – you – for a week. At the end of the week, we go back to just like things were." I

Tiffany went on: "You can agree, or I can show these revealing pictures to Ms. G and maybe a few others. The choice is yours."

I was floored. What could I do. Tiffany concluded: "I have to go, my friend is waiting for me downstairs. I'll give you some time to think it over. If you agree to my proposal, meet me for lunch at Antonio's, 12:00 p.m. tomorrow. You can keep the pictures to help you decide...I can always print more. Have a nice day .... Cum licker." With that she turned around and went off, leaving me dumbfounded, pictures in my hand, and, surprisingly, an erection.

Friday

I slept little Thursday night. What a mess I was in now. Once or twice I thought about telling Kate what had happened. But I quickly disregarded that idea. Maybe I could get though this without her finding out. Tiffany said it was only for a week. Then things could go back to where they were. I eventually made up my mind to give Tiffany the benefit of a doubt. I didn't help that I seemed to have a perpetual hard on since she visited me on Thursday. So, Friday at 12:00 I was at Antonio's. Tiffany walked in about 10 minutes later. She was impeccably and professionally dressed, back skirt, professional blouse, jacket, tasteful, but definitely high, heels.

"Good, you made your decision." She said, then in a hushed tone, "slave." I then got us a table and we sat. The next thing I know I felt her foot, in her shoe, pressing against my crotch. She asked "What kind of underwear are you wearing?" In a near whisper, hopefully so no one would overhear, I told her "boxers."

"Oh, that will never do. Go to the bathroom, take them off and bring them to me." Tiffany said.

"Tiffany, plea...." I began

"NOW!" she said, loud enough to get the attention of some of our fellow diners.

I immediately got up. Struggling to walk in such a way that would not make my erection obvious, I made my way to the restroom. In the stall, I took off shoes, my pants, and pulled down my underwear. I felt humiliated, socked feet on the tile, naked from the waste down, praying that no one came in and looked under the stall. I managed to get dressed again, without incident, when the problem became what to day with my underwear. I tried putting them in my pocket, but the bulge they made was tremendous. I resolved myself to balling them up as tightly as possible in my right hand and carrying them through the restaurant to Tiffany. I handed them to Tiffany as I passed her chair and took my seat opposite of her. Much to my embarrassment, Tiffany then shook out my underwear for all to see, then placed them in her purse to the surprised eyes of the on lookers.

Tiffany had a salad. I had a pasta dish, which I hardly touched. Tiffany had me open my pants. With her shoe, she fished my dick you of my pants. Fortunately, due to the table cloth, no one could see. But it made eating difficult. Eventually, she told me to rub it. Turning bright red, I did. She watched me, eating her salad as I played with myself, trying not to let anyone know. In a conversational voice, she asked if I was leaking. I told her I was. She told me to show her. I brought my hand to the table, and keeping it low, showed her the precum on my fingers. "Lick it off for me," she said. And, God help me, I did. In an upscale restaurant, penis out under the table, I licked precum from my fingers. And my hard on raged and Tiffany had me do this two more times.

After I paid the check, Tiffany said – "Let's go." I started to put my penis back in my pants when Tiffany asked, "What are you doing? Did I till you to do that." Flustered, I explained that I couldn't stand up like this. "Ask nicely," she said. "Please, please let me zip up my pants." I asked.

"Please...Mistress" she instructed.

"Please, Mistress, Please let me zip up my pants" With a nod, she gave me permission and I promptly stowed my erection and followed her out the door.

I thought we would say good bye and I could return to work, but that was not to be, yet. Follow me she said, and she took off at a brisk walk across the street to a shopping center. I followed, getting a bit nervous as she moved toward the door of "Victoria's Secret." Thankfully, my hard on had subsided as I followed her into the store. She finally turned and looked at me. I thought you could buy some more underwear. Then, before I knew what was happening, she had me standing in front of a display of panties. A saleswoman approached us and asked if we needed any help. Much to my continued embarrassment, Tiffany told her "no thank you, I think we can manage," as she held a pair of pink, silk, panties up to my waist. "These will do nicely. Go buy them and meet me outside," Tiffany instructed. She then turned and walked out the door.

At the register, I struggled to maintain my composure as I handed to the panties to the same saleswoman who had offered to help us. It was clear that she knew the panties were for me, and after she rung up the panties and placed them in the cute little "Victoria Secret" bag, told me that she "hoped I enjoyed my purchase." I must have turned seven shades of red as my embarrassment grew.

Outside, I met Tiffany. I tried to hand her the bag, but she refused saying "It's your purchase, your panties, you carry." She walked with me back to my office building. I was attempting to come up with some excuse for the "Victoria Secret" bag to tell my coworkers, when she stopped me outside the First Floor Men's' Room. Go in there and put your panties on. I went in and fortunately found the handicapped stall vacant. Grateful for the extra room, not to mention that it was the last stall in the room, I again took off my shoes and pants, humiliated again as I stood in the bathroom stall, socked feet, this time pulling up my panties over my again erect penis.

Once outside the restroom, Tiffany escorted me down the hall to an unpopulated corner of the building. "Show me" was all she said. I unzipped my fly and spread it so she could see the pink panties covering my erection. "You will wear panties the rest of the week. Have a good rest of the day – Cum Licker." She gave me a peck on the cheek, spun around and disappeared down the hall and out the front door.

The rest of the day was interesting to say the least. I never knew underwear could be so erotic and frustrating. Throughout the day I was left with a perpetual erection that rubbed against the silk undergarment every time I moved. I eventually determined that I was not going to be able to get any more work done and decided to take off a little early. The problem then became the panties. I could not take them home. If Kate found them, I would be in real trouble. I decided leave them at the office. I went to the bathroom, took them off, locked them in my desk and headed home.

When I got home, no one was home. I changed into some shorts and a polo shirt and went out to do some work in the garage. I was cleaning some tools when I heard Kate's car drive up and park in the driveway. I didn't turn around, but I heard them all walk towards the house and go inside. However, a chill went down my spine when I heard Tiffany's voice behind me say "Hello cum licker, lets take a quick peak at those panties."

I turned around to face Tiffany. She had changed cloths, now wearing gym type shorts and a tee-shirt. She had a stern look on her face as I explained "I'm not wearing them."

"I'm not wearing them, Mistress." scolded Tiffany.

"I'm not wearing them, Mistress," I replied.

"Where are they?" Tiffany questioned. I explained that I had locked them in my desk, promising to put them on first thing when I went back to work.

"I take my time to help you pick your cute little panties out, I instruct you to wear them, you DAMN WILL WEAR THEM, SLAVE!" Tiffany said, her voice rising.

"You will have to be punished. Go get in the car, while I go tell Mrs. G, that you are coming with me on an errand and taking me home."

I sat in the car while Tiffany told my wife God knows what. She got in the car and instructed me to drive the nearest grocery store. When we got there, Tiffany demanded $50, which I gave her. Then, without another word she disappeared into the store. She returned fifteen minutes later with a large bag, no change, and instructed me to drive to my office.

Once in my office she asked about the cleaning people. I told her we have a cleaning crew of two ladies. Since it was Friday, I explained that they would not come through the offices until Sunday. "Good," she said. "Pull down your pants!" she ordered as she turned and locked my office door. I stood, shorts around my ankles, boxers still covering my groin. "Those disgusting underwear too!" Tiffany firmly instructed through clenched teeth. I pulled them down. "Go sit on the desk," Tiffany continued.

I waddled over to the desk, trying not to trip as shorts and underwear were still around my ankle. What a sight I must have made. I finally made it to the desk, moved some papers and got onto the desk, sitting, facing Tiffany. Tiffany approached, pulled a chair in front of me and sat down. She pulled my shoes, shorts and underwear all the way off and spread my legs. She then opened her bag. She took out a large bowl and large bottle of water. She poured the water in the bowl and sat it on the floor between my legs. Next, she took out a big pair of scissors. She said "Be very still," and she reached up, moved my terrified penis to the side and began trimming my pubic hair. Once she had cut it short, she reached into the bag and pulled out shaving cream and a package of disposable razors.

Tiffany lathered me up and proceeded to shave my pubic area and penis. I grew hard as she touched me to shave me. The shaving cream felt good as she applied it and methodically removed it with a razor. When she was done, she handed me a bottle of lotion and told me to put it on, but not get carried away. I put the lotion on my now hairless pubic area, cock and balls. Tiffany watched as I resisted the urge to play with my now hairless member.

She then told me to clean up the mess, instructing me to put all the hair clippings, used razors, shaving cream and underwear in my office waste basket --- a "surprise" for the cleaning ladies as she put it. I straightened up my desk. I was still wearing nothing but my polo shirt, bald penis poking out, when Tiffany told me to stop. She ordered me to turn around and face the desk. She told me to take my shirt off. Now, naked, I bent over and rested my hands on the desk as she continued her instructions.

"Spread you legs!" she almost shouted as she kicked my ankles out, forcing me to spread my legs until I was truly uncomfortable.

"Time for your spanking" she said. "Keep your eyes straight ahead."

Now, I had not been spanked since I was a child. I had no idea what it would be like to be spanked, but when Tiffany said she was going to spank me I thought there would be a few little swats and it would be over. Boy was I wrong.

Tiffany hit me with a ruler, so hard I could feel it up my spine. I struggled not to yell as she hit me again. Then she hit me again and again. First she concentrated on the left cheek, until I could hardly stand it. Then she paused.

"Wow, look how red your left cheek is and how pale your right cheek looks." She observed. It was true. My left cheek not only stung, but felt hot, while the right cheek felt cool.

"Lets see if we can fix that," she said, as she took the ruler and started in on the right cheek. After a while of spanking the right cheek, she started back on the left check. Then alternated between them. Tears began to flow from my eyes.

When she was done, she stepped back to admire her work. "Keep looking straight ahead," she ordered as she touched my ass. I could feel that there were welts as she ran her fingernails over them.

"You should see your ass, slave." She said. Then she got close behind me. "But someone liked it," she said. "Look at your cock." I looked down and realized that I had a massive erection. I felt Mistress Tiffany (I had begun thinking of her as Mistress now, without any prodding) lean against my back. Then I felt her sex up against my ass. I could feel her soft pubic hair. Her flesh, her wetness She began rubbing herself on my ass.

"Stroke your cock for me, slave" she whispered in my ear as she ground herself against me. I could feel her wetness coat my ass and it good. "Look at your naked cock as you stroke it – watch it." She continued to whisper hotly in my ear.

Next, she put her panties over my head, with the crotch over my nose and mouth. "Smell me. Smell the pussy that you can't see, that I'm rubbing against your red ass," She said and I inhaled. I could smell her, the crotch of her panties were moist and musty and my cock throbbed. I felt her reach her hand down to play with herself as she rubbed against my ass...fucking herself against my ass.