tagBDSMNaughty Baby Sitter

Naughty Baby Sitter


Just after I turned eighteen my parents decided to go on a short vacation, but I could not go with them because I had just started a job with a local hamburger joint. Although I was eighteen, my parents, still thinking of me as a little kid, asked the girl who lived next door to look in on me occasionally. She was a twenty two year old college student who lived with her parents. She used to baby sit me years before when my folks would go out for the evening. They asked her to make sure I did not get into any mischief, like wild teenage parties.

Her name was Christine. She was a rather full figured Mexican girl. Dark hair, brown eyes, about five feet five inches tall, a rather large set of tits and correspondingly large ass that she used to wiggle around the neighborhood. Although, she was somewhat overweight, she was still an attractive woman.

Her bedroom is on the second story of her parents' house as was mine. My window was directly across the driveway from her's. During the past year I had noticed on occasion she would leave her shades up and lights on as she undressed for the night. I watched in amazement as she unbuttoned her blouse to reveal those big boobs encased in a sexy black bra. By this time I was fumbling for my already rock hard cock. Next her tits were released and I feasted my eyes on them. She would then wiggle out of her skirt and black panties and sometimes bend over with her butt to the window and give me the best view of a womanly ass that I ever had. I suspected that she knew I was watching, but she never let on that she knew she had an audience. One of these little shows was usually good for a weeks worth of masturbatory fantasies. I recall having a hard on a good amount of the time for no reason at all. When Christine gave these performances it was really reason to jack off, sometimes twice or more in one day. One time when her parents were gone she brought her boyfriend home. She brought him to her room and did her show for the both of us, then her boyfriend pulled down the shades and I was left pounding my cock and imagining what they must be doing.

Anyway, on the second day of my folks' absence I was up in my room after coming home from work. I was in my usual horny state that evening, however, I noticed the light in Christine's room was not on. So I grabbed a "girlie" magazine I had and started thumbing through it. In no time at all I was hard and needed some release. I had masturbated earlier that day before I went to work while showering, but I was ready again. I took off my shoes and socks, my shirt and my pants. My underwear bulged in my excitement and I removed these to reveal my turgid cock. I gave it a couple of preliminary strokes as I stood there and felt that familiar tingle go from my buttocks to my heels. I retrieved my magazine and lay down on my bed, took my cock in my hand and started to stroke it. I was enjoying the pictures as well as the feeling in my body. Sometimes I would fondle my balls and pull at my ball sac to give an added tingle. Also, I would run my free hand over my belly and chest as these areas were also sensitized and I would give my nipples a good rubbing as this would increase my self pleasure. Soon I was lost in my reveries and totally oblivious to the world around me.

Suddenly, the door to my room burst open and I looked up to see Christine standing there with a long thin piece of wood in her hand that looked like it came from her dad's work bench.

"What are you doing?" she demanded.

"Christine, I, I...." embarrassed with my cock still hard in my hand I did not know what to say.

"Stand up this minute, Joe!"

"Christine, I can explain."

"Your parents told me to keep an eye on you and make sure you don't get into any mischief and on their second night out what do I find? Stand up now!!" The authority in her voice was unmistakable so I sheepishly complied. As soon as I stood she gave my bottom about five good lashes with her switch. It made me jump and squirm as I stood.

"But Christine, Mom and Dad said that I shouldn't be throwing wild parties and stuff like that."

"I'll be the judge of what you should and should not be doing, and to decide upon your punishment."

"Punishment? Christine how can you say that? Besides, I've seen you take your boyfriend up to your room when your folks are gone," I said somewhat indignantly. Next her switch came down upon my cock which was still hard and standing out in front of me. Once again I jumped at the sudden sharp pain, but my cock remained hard.

"You little twerp, I know you watch me at night and now you're going to pay for that too." She grabbed me by my upper arm and propelled me across the room. I could tell that she had respectable strength for a woman. We got over by my desk and she pulled out my chair. I noticed that a few buttons on her blouse were undone and I caught a good look at her cleavage that revealed she was not wearing a bra. Her large nipples appeared to be hard under her shirt. She sat down and then took my hand and firmly drew me down across her ample thighs. She grabbed my cock and made sure that it was out of the way as I settled in for my anticipated paddling.

"Do you know why I'm doing this , Joe?"

"No, Christine, not really. I'm not being bad and it feels so good."

"It feels good does it. Well I'll show you. You have been naughty. Not only playing with yourself like this, but watching me undress. You must be punished and I'm going to warm up this little ass of yours." As soon as she finished saying this I felt her hand come down on my ass very hard. My whole body twitched. "I love to see the male ass in such a subservient position," she said. She then continued, slap after slap as hard as the first. My bottom was twitching and my legs were squirming as I endured the blows. Although I was in pain my cock was as hard as ever and my twitching and squirming were causing it to rub on her blue jeans. Soon I was begging for mercy with each slap, but she persisted. Slap! Slap! Slap!

"Oh, Christine, please..." I pleaded as tears started to form in my eyes.

"Alright, Joe, do you promise to be good from now on?"

"Yes, Christine."

"Do you agree that if you act up in the future you should be punished again?"

"Yes, Christine, anything you say," said I with much resignation and in a total state of submission.

She delivered one final slap and then pulled me back off her lap so that I was kneeling beside her. She saw my tears and reached out and embraced me bringing my face into her cleavage and I put my arms around her as she comforted me. The smell of her perfume and the soft, exposed flesh of her breasts were intoxicating. On impulse I kissed the exposed flesh of her cleavage. Her breathing deepened and she clutched my face to her chest and sighed. "My you have big tits, Christine."

"Yes I do," she replied as she unbuttoned her blouse the rest of the way. I was inspecting her magnificent breasts when she said, "Now, Joe, kiss and lick my tits very gently." I complied and her heavy breathing and sighs had me really turned on. She directed me from one breast to the other and finally pushed me away and stood up and removed the rest of her clothing revealing her full figure for me to inspect for the first time at close range. She took me by the hand and led me to my bed. "Now I'm going to show you how to give real pleasure to a woman, Joe." Christine and I lay down and began kissing. Soon I was back at her tits. After a while she directed me to start kissing her down her belly, which I did. This caused increased moans from Christine. "Lower, Joe, lower," she whispered. Soon I was down by her bush and began to move my fingers in and out of her. She was very wet and her hips bucked in response to my ministrations. She told me to kiss her pussy. I was reluctant because I thought it would smell and taste nasty.

Finally, I gave in and began licking her lips. It was salty and tangy, but fresh and pleasant all the same. I continued licking her pussy lips and clit. After about half an hour she told me to roll over. I did so and she took my cock in her mouth. I had never experienced this before. My previous experience had been with girls getting me off with their hands. This was much better. After a few minutes of this she stopped and then climbed on top of me and slid my cock into her. We smiled at each other and she began to move rhythmically. Once in a while she would lean forward and rub her tits on my chest. Soon I exploded in orgasm and I was on cloud nine for a few moments. When I recovered I opened my eyes and say Christine smiling down at me. I was still hard and she contracted her pussy around it. This action on my tender cock sent shock waves through my entire body.

Afterwards, she told me she got the idea of giving me a spanking from a book of her dad's she had found. She had been fantasizing about it and decided to try it with me. She also told me not to really worry about masturbation. She actually thought it was "cute' to see a boy masturbating and I should continue with it. Christine also told me that she enjoyed giving me the shows and to look forward to a couple of new treats.

"If you're naughty again I'll have to take you over my knee again, Joe," she smiled.

"OK, Christine," I smiled back at her. She gave me a long, deep kiss and then went home for the evening. As it turned out, she was required to discipline and then "comfort" me a couple of more times during my parents' absence and then occasionally through the next year until she graduated and moved away.


Report Story

byhohound© 3 comments/ 128735 views/ 8 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartSJohn804, irishsexstorylover and 6 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (3 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (3)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: