Watching My Babysitter

Category: Male-Female (MF)
Submitted by: jacob Age: 50 Gender: Male

I'm 50 now, with grown kids from my second marriage. Life is great, but I still think a lot about my first sexual experience: I was nine and my friend's big sister, Bobbie (Roberta) was babysitting me. Bobbie was about 17, short, a little plump and very well developed. In fact, Bobbie was absolutely stacked. Every guy in our neighborhood talked about her breasts; even a little kid like me who knew absolutely nothing about sex, but she never allowed anyone that I know to touch her. I think she was very self concious about her breasts and didn't want to ruin her reputation which was important in those days.

Anyway, that night we were sitting on the couch together and I was getting sleepy. She pulled me towards her and put her arm around my shoulders. My cheek was resting against her left breast and I could feel it full and warm under her cotton nighty. I had lain like this many times with my mother and aunts, but with Bobbie it was a very different feeling. I had gotten erections before, mostly from looking at magazines or having wet dreams, but that was the first time it had happened from contact with a girl. It was great!

While she stroked my head, her other hand was resting on her lap. Nothing happened at first and I guess I fell asleep for a few minutes. I was awaken by Bobbie rubbing herself. The nighty was hiked up past her waist and I could clearly see her fingers rubbing the outside of her pussy. Then, she inserted her middle finger inside her cunt and stopped for a moment. I didn't move, in fact I held my breath as she started to squirm a little bit. She was being careful not to wake me, so her hips only quivered a little bit as she arched her back a little and then relaxed. She repeated the movement over and over again, and pushed my face into her erect nipple unconciously which made it hard for me to see her hand. That's when things got more interesting.

I was breathing harder then and Bobbie was getting more vigorous with her movements. Even though I couldn't see her fingering herself, I could hear the wet sound of her movements. I had no idea what was going on, but I didn't want to miss it so I pulled away so I could see. She looked at me, stopped what she was doing, put her legs together and pushed her nighty down over her knees. But things had gone too far for me to just lie still and forget it, so I put my hand right between her legs onto her pussy without hesitation.

Honestly, I didn't know anything about sex, but I'd seen my dad rub my mom's back and I figured it was the same thing. Really. I started rubbing her pussy and her nighty felt hot and moist to my touch. That is a sensation I'll never forget. Bobbie started to pull my hand away, but I was determined to continue, so we struggled for a few seconds. I got a few good rubs in and that was all it took to change her mind.

Then, she guided my fingers to the right spot and with both her hands on mine, she started rubbing herself fast and hard. I remember my cock getting so hard, it ached as she humped and moaned. In a few moments she started saying "Fuck me. Fuck me with your hand, fucker. I'm wet and horny! Fuck me hard" And then she arched her back really high and pressed my hand so that the flannel nighty and my fingers entered her pussy about and inch. I felt the wetness right through the flannel and she yelled,"Fuck, fuck, fuck...." about ten times as she climaxed. For a nine-year-old kid it was like a week in Disneyland comrpessed into a wet minute.

After she caught her breath, she realized what had happened and pushed me away. She apologized for swearing, insisting that she had heard those words while eavesdropping on a phone call between her mother and her uncle, which was probably true. I was pretty upset that she wanted me to go to bed and I got teary eyed.

Then, she started hugging and comforting me. That's when she felt my hard little cock against her leg. At first she pulled away, but I clung onto her. Then she turned me so I was facing her, my legs straddling her body. Her nighty had slid up past her pussy and my cock was only an inch away from her pussy hair. I was unable to breathe because of my excitement.

She cupped the cheeks of my ass with her hands and pulled me towards her, forcing my cock against her wet pussy. At once she started humping me, her huge tits pressing against my face. I was dizzy and started gasping for air as she whispered into my ear for me to fuck her. I didn't didn't know how to fuck her, so I just hung on for the ride. I remember my cock entered her a couple of times, but mostly she just rubbed against me, using all her strength to maximized the friction of my cock against her clit.

I was feeling sensations I had never felt before. My balls started tingling so intensly that I could hardly stand it, but she was so much stronger than I, that my efforts to slow things down were usesless. Then she stiffened her back again and with one powerful hug she came. My cock was pointing straight up and pushed hard against her clit. I felt her contractions as she froze her body, completely supporting me above her. In that moment, as she coaxed the last few contractions from her wet pussy, I felt hot cum travel up my cock and squirt out. My cock was pumping cum out onto the top of her pussy hair and stomach. It was the most intense feeling I'd ever experienced and I often think of it now when I jack off or make love to my wife.

In the next five years, Bobbie led me through many more experiences, but she never let me stick my cock into her again. I'm sure she was afraid of getting pregnant. She may have even been a virgin until she was married at 22. It doesn't matter. I was just a kid being treated to a life-changing set of experiences. She taught me how to touch her in dozens of ways that made her cum, cum again and cum a third time. She stole magazines from her father that showed a man licking a woman's pussy and begged me to do it, which I did reluctantly at first and then frequently. Over those five years, Bobbie and I made each other cum almost every day after school before our parents came home from work. That's well over 1200 times.

After Bobbie got married, she moved away and my family moved to another town. I never stopped thinking about her. Then one day, I was at a local mall with some friends and I saw her shopping with her husband and little girl. I caught her eye and she smiled at me, but motioned for me not to approach her. I followed her for a while and when she left her husband to go into the bathrooms; I followed her.

She was almost at the end of the long hall ready to enter the restroom when I called to her. She told me to wait for her. In a few minutes, she came out and motioned for me to come into the girls' bathroom with her. There was no one else in there. She pulled me into a stall, unbuttoned my pants, pulled them down to my knees and started sucking me. I wasn't even hard yet, but she got me stiff in a moment. In a short time, I came in her mouth, unloading a huge amount of cum. I remember some of it ran down her chin.

Then someone came in and we were silent. The woman entered a stall and I pulled up my pants and got buttoned up. We slipped out unnoticed. In the hallway I asked for Bobbie's phone number, but she told me we would never see each other again. I told her I loved her and she fought back the tears. The she admitted to me that she loved me too and often thought about me when her husband clumsily fucked her or she masturbated. She hugged me and ran away. I did not follow her and I've never seen her since. That was 32 years ago.

Bobbie, if you read this I want you to know that you were sweetest woman I've ever known. I hope you're happy and healthy.

[lb][i]This story was originally submitted to Solo Touch and not published because it violates the rules.[/i][rb]