Gift From The Babysitter - Cover

Gift From The Babysitter

by Nemesis

Copyright© 2005 by Nemesis

Erotica Sex Story: A young boy loses his virginity to his teen-aged babysitter.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Consensual   Heterosexual   First   .

I lost my virginity when I was 10 years old. It was taken by my 15 year old babysitter late one night while my parents were out to an early dinner and a late play. Peggy was my favorite babysitter for a number of reasons: She was beautiful, smart, funny, and always dealt with me like I was her age, not just some little kid. She was a cheerleader at our High School and sometimes wore her uniform over when she sat for me. Most nights, once she had me in bed, she would stay and talk until I began getting drowsy.

We would talk about school, sports - particularly Little League, which I loved, her boyfriends, and occasionally girls. In many ways, she was like a big sister to me. This evening was no different. I was in my pajamas and under the covers and she was sitting on the edge of my bed. We had been talking about the baseball game I had played in that weekend and I had mentioned that a girl I liked had been watching.

"So, were you showing off for her?" she asked with a teasing tone to her voice.

"No!" I loudly denied it.

"Not even a little? I bet she was there just to watch you."

"Maybe a little, but not much." I finally admitted.

"Have you kissed her yet?" We had talked a little bit about sex - enough for me to know that it was embarrassing. I knew a little bit about how things went though, mostly vague notions and locker room myths.

"Maybe." I was blushing and was glad that the only light was coming from the hallway.

"I knew it!" she laughed. She leaned over and made loud puckering noises at me.

"Cut it out!" I reached up to tickle her. Peggy was always very ticklish and I could occasionally bully her this way. She giggled and twitched and began to tickle me back, starting a free-for-all tickle fight. That ended rather abruptly when I missed my grab at her arm and instead got a handful of her right breast. I froze and so did she. That image is still absolutely clear in my mind. She had her right leg up on the bed and her cheerleader's skirt was bunched up around her waist, so that her panties were showing clearly. She was looking at my hand and so was I. I knew that I should let go, but I had never felt anything quite like that.

I don't know how long we sat like that. Her breast was warm in my hand underneath her fuzzy sweater. It was firm, but soft - a combination I had never even imagined. My curiosity finally got the better of me and I began to rub, exploring this new territory.

"Um. Mike." she said as she reached up and pulled my hand away, "You probably shouldn't do that."

"I'm sorry. Did I hurt you?" by now my eyes had wandered down to her thighs.

"No, but boys shouldn't just grab girls like that."

"OK. But I'll bet Rob's done it before." Rob was her boyfriend - something of a nerd and definitely not the sort of person you'd expect a cheerleader to be dating.

"That's none of your business!" she said primly as she smoothed her skirt down. I was beginning to feel some tingling in my groin. A very unfamiliar sensation at my young age, but I liked it. This was exciting!

"He has, hasn't he?" I continued to taunt her. "I bet you've done all sorts of things."

'Wouldn't you just like to know? Just be careful or I'll grab YOU somewhere!"

"Come on. Tell me! I won't tell anyone!"

"No, you little snoop! Now stop asking or you'll be in so much trouble!"

"He's French kissed you hasn't he?"

"That's it!" she began tickling me again, and before I could even stop laughing long enough to tickle her back, she grabbed the sheet, and me, between my legs. I froze. I had been kicked in the nuts before, but I'd never had anyone just grab them. Especially not a pretty girl! "I told you." she grinned at me. "Now, are you going to keep pestering me?"

"Uh... I think you should let go." I was starting to get an erection. Her hand was slowly massaging my dick and my balls and the feelings were building to a level I'd never thought about.

"Not until you agree to stop bothering me... Oh my." She interrupted herself as she felt the rapid swelling in my prick. She kept rubbing, slowly, but firmly.

"Peggy, please let go." I was getting VERY embarrassed.

"Why? Doesn't it feel good? Besides, I thought you wanted to know what Rob had done."

"Unnnnnh." I moaned as her hand began tracing the outline of my erection through the sheet and my pajama bottoms.

"Let's just see what this looks like." she paused only long enough to pull the sheet back. My dick was straining at the buttons on my pajama bottoms. "Oh, you're big for your age!" she said as she wrapped her hand around it and continued to stroke. I was probably about 4" long and maybe 3/4" across at that age and not a wisp of hair.

"Peggy..." was all I could manage.

"I think I need to get a much closer look at THIS!" she began unsnapping my pajamas and in a few seconds had them down around my knees. My mind was caught up in the pleasure waving up from my groin. The thought that I was naked was nowhere to be found. Her hand again found it's way to my erection and began its slow stroking motion.

I moaned again. She looked at my face and said "Mike, I think I know what you'd like." she bent down and licked the head of my penis. I jumped as though I had been shocked, which I suppose I had been. My eyes snapped open and I watched as she pursed her lips at the tip of my dick and slowly pushed it into her mouth. I had never heard of a blowjob, but I knew what I liked! There was nothing on earth that could possibly compare to this. All I could feel was a tingly sensation in my balls as her right hand gently cupped them and a warm wet roughness as her tongue explored the length of my dick.

She began pumping her head up and down, sliding her lips over the head, and then plunging them back down to the root. In seconds, I was pumping my hips into her, actually fucking her face. I have no idea how long that went on, but it couldn't have been very long when I felt every muscle in my body begin contracting and relaxing. She pushed me all the way into her mouth and began swallowing, causing me to reach a fresh peak of pleasure. What felt like an hour or so later, the spasms stopped and she pulled herself slowly off my wilting dick.

She sat back, licked her lips and said "Now, what did you think of that?"

"Jesus Peggy." I finally managed to gasp, "That was great!"

"Well, I'm glad you liked it!" she giggled. "Would you like to see some more?" Without waiting for an answer, she took my hand and placed it on her breast. What a night! I began to rub, and stroke, and she leaned into my hand. A few moments later, she took my hand and placed it under her skirt, so that my fingertips were brushing the crotch of her panties. In all honesty, this felt a lot less interesting. But I was quite distracted when she grabbed the hem of her sweater and pulled it over her head and off. My eyes must have been the size of saucers as she reached behind her and unsnapped her bra and took it off.

 
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