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A Gift From The Babysitter
by Tail Spinner (tailspinner80@yahoo.com)

***

A story sent to me of a young lad losing his virginity 
to his babysitter. (F-teen/b-pre-teen, ped, 1st)

***

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.

I tried to reach back to those inviting mounds, but she 
firmly took my hand and put it back between her legs. 
"Rub there, please Mike." I did as she asked and she 
leaned herself towards my head, pulling me so that my 
face was pressed into her breasts. "Mmmmm. Suck, Mike." 
That was all the invitation I needed! I took her nipple 
into my mouth and began to suck and lick. It was 
heaven. While my hand was exploring the double layer of 
nylon covering her crotch, my mouth was trying to take 
her entire tit into it.

Sometime during this time she must have unzipped her 
skirt because she pulled my hand away from her groin 
and slipped her pleated skirt over her hips and down 
her legs. Seconds later her panties and underpants 
followed it onto the floor. What an image! A gorgeous 
15-year-old girl was sitting in my bed completely 
naked! Her breasts were full and firm, and her pubic 
hair was a reddish triangle between her legs. I wasted 
no time at all putting my hand back between her legs.

My fingers were tracing the soft hair and the firmness 
of her outer lips. I had stopped sucking her nipple so 
that I could see this marvelous new terrain that my 
fingers had found. She leaned back on her elbows and 
spread her legs, giving me much better access to her 
crotch. I traced a finger down from the top of her slit 
as far as I could reach. 

I remember being surprised that she didn’t really have 
anything down there, but I continued exploring. I was 
using both hands now, spreading her lips so that I 
could get a decent look. When I finally found her 
vagina, it was somewhat by accident. I was using my 
fingertips to push from the top of her outer lips down 
to the crack of her ass when it slipped into her. Once 
I found it, I began to really explore, trying to push 
my finger all the way in. She was very tight - I found 
out later that she and Rob had ‘done it’ twice and that 
he had been her first time.

After a few attempts to get my finger inside that warm 
wet hole she said, "Mike, I want you to push it in and 
out - like this." and she took my hand and began 
thrusting it into her. My finger was slipping in 
further with each push, which was fine with me. This 
was getting interesting! She was moaning and starting 
to push her hips into my hand. 

"MMMmmmmm. That’s great Mike. Here, give me your other 
hand." she took it and put it just above the finger 
that was furiously pumping in and out of her now 
sopping wet tunnel. "Rub there...Oh yeah, yeah...." She 
started bucking her hips and crying out loud! I had NO 
idea what was happening, but I sure wasn’t going to 
stop what I was doing! Her body was writhing on my bed, 
causing the springs to squeak loudly. My wrist was 
starting to get tired by the time she finally reached 
down and pulled my hands away.

"Oh God Mike, that was wonderful. Now, I’m going to 
give you a real treat. Come here..." I didn’t fully 
understand what she wanted, so I slid my feet out from 
under the tangled covers and moved up so that I could 
lie down next to her. "No, here. Lay on top of me.... 
Like this..." she guided me so that I was lying on 
fully on top of her and between her legs. 

It’s really kind of funny to think about today, since 
my pajama top was still on and my bottoms were totally 
entangled around my ankles. She reached down to my hips 
and took the top up and off, allowing me to feel those 
wonderful breasts pushing up at my chest.

She gave me a hug and said, "I want you to fuck me." 
She raised her knees up to about the level of my rib 
cage and began rubbing her crotch against mine. It felt 
heavenly. The coarse hair was almost tickling my dick, 
which was beginning to reawaken. "I...I...don’t know 
how, Peggy."

"It’s OK Mike, I’ll show you how..." and she reached 
down between us and took my semi-erect penis in her 
hand and began rubbing the stiffening head up and down 
her very wet slit. I remember very clearly the 
sensation as she placed the head of my dick at the 
entrance to her body. It was hot, and soft and 
slippery. She took her hand from between my legs and 
wrapped her arms around my waist and said, 
"Push...Oohhhhhhh" as I slipped into her. It was so 
tight that it actually hurt the head of my dick! As I 
slid into her body it felt like it was being split in 
two. 

In no time at all, I was buried to the hilt. I don’t 
have a very coherent memory of the next few minutes, 
but I do remember that she didn’t have to say anything 
about going in and out. I figured that out on my own. I 
remember humping her wildly while she guided my frantic 
thrusts with her heels on my ass. She had a firm grip 
on my back with her hands and was moaning a lot. Then I 
climaxed again. 

My body began pushing as hard and as fast as it could, 
then I stopped, with my dick shoved as far into her as 
I could manage while she was twisting under me, rubbing 
her crotch against me. I could feel the contractions in 
my balls and my dick as a few squirts of something 
pumped out of me and deep into her body. She laughed 
and kissed me as my orgasm slowed.

As my dick was softening inside her, she relaxed the 
grip her legs had on me and was rubbing her hands up 
and down my back. "That was really nice, Mike. Really 
good for a beginner." I had absolutely nothing to say. 
My mind had stopped working when I entered her body. "I 
liked having you cum in me." she said in a dreamy 
voice. And then both of us stopped - there was a flash 
of headlights in the driveway!

My parents were home! "Get off!" she said as she 
frantically rolled out from under me. We could hear the 
car in the garage now. She threw her sweater on and her 
skirt and panties. Her bra and underpants she stuffed 
under my bed with the five tons of other garbage I had 
there and ran out to the living room. Meanwhile, I was 
trying to pull my pajama bottoms up and get the arms 
right on the top. Finally, I managed it, just in time 
to hear the back door open and my folks walk in.

I lay down and feigned sleep as best as I was able. I 
heard quiet murmurs of conversation, and then my father 
going back out with Peggy to take her home, which ended 
my night. But what a night! I don’t know where Peggy is 
today as her family moved to California when her father 
was transferred about six months after that. But I’ll 
never forget her, or her gift to me.

END

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The author does not condone child abuse, this story is
meant as an erotic fantasy not real life. Anyone acting
out such scenarios in "real life" can look forward to
many unproductive years getting it up the butt by a 
fellow convict in their local prison system.
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