A Gift From The Babysitter

2559 words | 18 |4.54

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.

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  • Reply Blackbear7 ID:16kc8zyda2o0

    We grew up in the early 70s when kids were left home alone. Did as parents said. Once home, if daytime, outside we went. Night time, we were sound asleep. No babysitters.

  • Reply Jason ID:n4o27wzra

    Great story. Charlene my babysitter used to kiss me, tickle my feet and rub them. I rubbed her feet and she moaned with pleasure. I tickled her feet and she laughed hysterically and when we kissed she giggled joyfully.

  • Reply Garo Lopez ID:1cx59s7xs2mj

    Awesome what an understanding young lady!! I wish the girls ( older girls )!adult women around me when I was a teen were all lovely Peggy in this story . She would have had my total admiration.

    • Jason ID:5fu3cxftmh

      Great story. Can you do one of him playing with Peggys feet

  • Reply Bloody ID:1jybr2qj

    Wow i love dat story

  • Reply Danny ID:3057hz2fii

    It’s too bad she didn’t have time to teach you the proper way to eat a cream pie

  • Reply binkey ID:abtk75qj

    Very nicely written made the story sweet not sordid.

  • Reply l ID:bo2qeo18k


  • Reply Nikhil ID:el3ioou8m

    I really need this gift from you when I was 10 years old. My cock 3 inches super hard at that time.at the age of 10 my cock not release semen cum.so that time if you mate me and give me a beautiful fuck so I enjoy at list a huge massive dry orgasam inside your vagina.

  • Reply excited ananymous ID:pvku2bbm3

    Nice, very cute story!! But as a babysitter, I would have had that friendly boy experiment by a few steps. First night, babysitter only masturbates him, and makes him discover the pleasure of having an orgasm (And at his age, most chances are it would be dry orgasm! Which could be repeated quire easily. Those ”squirts of something” would obviously come up at age 12 or 13…) A week later she lets him grope and fondle her breasts. And rewards him with a hand session if he does it properly. Some time later she lets him undress her down there and discover her feminine assets. Each babysitting night would also bring up a discussion about his masturbation attempts. And only much time later would she indulge in oral on him. Again, much time later, let him penetrate her. Then she teaches him positions. And each and every night she has him swear he won’t tell anybody about their bed activities ”We keep it as our big secret!”, otherwise she wouldn’d be able to come back.

    • curiousman ID:1m5ux7g20b

      im curious, have you had any experiences? would love to know more

    • WonderingMan ID:7ylren8b0k

      You have definitely done this, maby mutible time bc you seem to have perfected the craft.

    • Author Pen Dragon ID:1fr6k6ud4

      10 is a little precocious, but not unheard of. Chances are he’s not getting molested by his babysitter. People fantasize about what’s unlikely to happen, not what’s most likely.

  • Reply Anonymous ID:n3ejxs5d0

    I would lick her pussy and cum in her

  • Reply 7 inch sceptre ID:2qm7cj6i9

    Sounds like a wild fuck with a red head with fire down below….

  • Reply John [email protected] ID:vuf1mnql

    I John nickname Woody in Lompoc my first sexual relationship wAs with my baby sitter she caught me masterbating said it’s ok I fucked her doggy style and anal she was a very large lady I’m still Loving large ladies any race.big Asses

  • Reply Carol ID:81rd7cezrc

    This made me wet, I soooooo want to fuck so hard

    • Cody ID:by20i6ic

      You have a kik Carol??