Where it happened: On the floor
Langauge: English
Sex: Male
Rating: 10
Category: Straight
My first time was fantastic…and very unexpected.
When I was in high school I made extra money babysitting. It was kind of unusual, a guy, doing babysitting, but the neighbors knew me and trusted me. So many Friday and
Saturday evenings, when my friends were out on dates or going to parties, I took babysitting jobs.
I was terribly shy and naive when I was a teenager, with little confidence with girls. I had a lot of fantasies though, and they had started with Kelly. She lived two houses down the street. Kelly was three years older than me and used to be my babysitter when she was 13 and 14 years old and I was 10 and 11.
My parents were very protective of me and even though my friends didn’t have sitters, my parents insisted. So Kelly would come over frequently. Even though I was fairly young I was sure starting to notice girls, and Kelly was very noticeable. She wasn’t much taller than I was but was really built for her age. She usually wore tight shorts and t-shirts that accented her shapely hips, fully developed breasts, and sexy legs. I thought she was
beautiful and started a long-lasting crush on her.
Needless to say, Kelly became the main object of my fantasies and, in my head, became the focus of many a jerk-off session in the shower or in my bedroom.
By the time I was 15, I was in the babysitting business myself. Kelly was about to graduate from high school and was one of the most popular girls in school. That spring, I
found myself regularly hired to babysit Kelly’s little brother, who was only 10 years old. I went over usually once a week on Friday or Saturday night. I’d order a pizza, horse around with the kid until 10 or 11, then he’d go to bed and I’d watch TV until the parents
or Kelly got home.
One Saturday, the parents were going to a big bash about 50 miles from home and, not knowing when Kelly would get back in, asked me if I could babysit their son and sleep
over at their house that night if it got too late. They’d be back the next morning. I agreed and came on over.
It was the usual routine. Junior and I watched a movie, he got his bath and went to bed about 10:00. Figuring that I’d be sleeping on the couch that night, I changed into my usual bed clothes, boxers and a baggy tank top, and relaxed on the sofa to watch a movie, “Dirty Dancing”. It wasn’t long and I heard the garage door open and in walked Kelly.
I was kind of surprised, not figuring she’d be in from the party she was at until the early morning hours. She said the party was bad, lot a creeps she didn’t know, and had dumped her date and come home.
She came into the TV room, lighted only by the moving running on the TV. Seeing that it was Dirty Dancing, she said she loved the movie and would watch it with me. She ran upstairs and came back down, changed from her jeans and sweatshirt into terry cloth shorts and a cutoff t-shirt that left her bare belly and back exposed. She looked
fantastically sexy.
She sat down on the couch with me and asked it she could share the ottoman I had my feet up on. And there I was, sitting next to my dream girl Kelly, her bare legs nearly
touching mine. I could smell her hair. Glancing out of the corner of my eye I watched her breasts rise and fall with her breathing.
She caught me looking at her and started to ask me questions. She wanted to know if I had a girlfriend and what I liked to do. She talked about babysitting me when I was about her brother’s age. She commented that she’d noticed how grown up I’d gotten in the last
couple of years.
As she said that she reached over with her hand and felt my biceps and shoulder, then reached under the narrow strap of the tank top and felt my chest. She turned on her side
and snuggled up close to me and moved her hand down to my leg and thigh, squeezing the muscles like she was checking me out.
This intimate attention from Kelly was getting me very hot and an erection produced a noticeable bulge in my boxers. I looked over at Kelly and back to the TV, where what’s-
his-name is dancing with that girl, he has no shirt on and she has just a tight leotard. Kelly moved her body in time with the beat of the music.
I realized that I had the green light to touch Kelly the same way she was touching me. Feeling bolder with that thought I put my right hand up on Kelly’s bare thigh and checked out her muscle the same way she’d felt me. Oh boy, it was great. Smooth skin, very firm and very warm.
My touching her must have started her engine too. She started to breath heavier and pulled closer to me. She kissed my neck and pushed her hand up under my shirt, rubbing my chest and playing with my nipples.
I turned toward her face and we kissed, than did a little tongue dance, and kissed some more. As she massaged my chest I pushed my hand across her bare back and up under her
cutoff shirt. Finding no bra in the way, I moved on around to her chest and found those wonderful breasts I’d admired for the past five years.
I’d hardly touched her breast when Kelly sat up…whoops, now I’ve done it. But no, she pulled her shirt up and over her head. She reached over and directed me out of my shirt at the same time. The glow of the TV bathed her body in warm light. I could only stare at her breasts, very round and very high on her chest. The dark nipples were raised and I reached over and pinched one, then the other. She returned the nipple massage and we clenched again for some more kissing.
She pulled me down onto the couch, my body nearly on top of hers. She rubbed my shoulders and back, then pushed her hands down under by boxers and massaged my ass
cheeks. Boy was I loving this.
Kelly commented on my hard body and that she wanted to see all of me. She pushed up against my chest and I got up off the couch and stood in front of her. The tent in my
boxers was directly in front of her face and she quickly slid them down, exposing my throbbing pecker.
After exclaiming how good I looked to her, she pealed off her shorts and panties, leaving us both now completely naked. I pulled her close to me, marveling at the feel of her breasts pushing against my chest. She pushed her hips close to me, mashing my hard cock tight against her belly. My hands helped out my pulling her tight ass closer to me.
She asked if I’d very done this before with a girl. Admitting that I was in uncharted waters, she then asked if I would like her to be my first. I told her that I’d been dreaming about her since I was 12 years old and this was like living out my favorite fantasy.
Without any further talk, I let my fantasy scenario play out, moving aggressively to kissing her wonderful body from head to toes with lingering stops at her breasts, belly, and of course her luscious pussy.
In my fantasy I’d eaten her out many times, but the real deal was rather unexpected. I wanted so bad to get my cock in there that I moved on once I’d gotten a good look and
explored that dripping slit to my satisfaction.
I moved back up toward her head, kissing her belly and breasts every inch of the way. I got fully stretched out over her, she spread her legs and I felt my throbbing dick pressing against the hot opening of her cunt. This was the moment I’d dreamed of and without hesitation, I worked my hips, pushing the head of my cock into her hole, first an inch, then two, slowing moving deeper and deeper into her belly with each thrust.
Kelly had her eyes closed and head thrown back. She was panting and moaning as she moved her hips in time with mine and forcefully pulled my ass toward her with each push.
No fantasy ever felt as terrific as feeling my cock buried up to my aching balls in her velvety hot pussy. She was very tight and very wet. Within a minute of my getting into
her I was shooting off like a firecracker. She went too and I realized our noisemaking might wake up little brother. But things calmed down pretty quick and we collapsed on the floor, soaked in my cum, her pussy juice, and our own sweat.
We cuddled naked on the floor for about a half hour, stroking each other’s body and confessing intimate secrets about each other. Kelly said she’d been hot for me even when she was my babysitter and would grab peaks at me to check out my body. I confessed my longstanging affection for her and lust for her body .
The pillow talk, nipple rubbing, and ass grabbing soon got me fired up again. This time Kelly got a change to fully explore my anatomy and gave very close attention to my hard
cock and balls. My cock’s first trip into a girls mouth really got the juices flowing again. Before I came in her mouth she threw her leg over my waist and sat down on me so that I could resume my playtime with her breasts.
She was to beautiful and sexy I still couldn’t believe it. My wildest fantasy had never been like this. Rising up slightly she placed my cock at the dripping entrance to her shaved cunt and I slid right back in. She impaled herself on me and arched her back as she started a slowing up and down motion on the shaft of my cock.
I reached to her pussy and teased the clit area at the top of the slit and that really made her nuts. She reached around behind her ass and massaged my balls hanging down below. This extra stimulation, while hardly needed, quickly brought us to another orgasm, first me, then her.
We laid together for a short time longer, but realized that we were risking discovery which would have ended my babysitting job there and gotten us both in hot water with our parents.
Kelly and I got up, she offered me my boxers, and held them as I stepped into them, giving me naughtly little touches and pinches as she pulled them up. I pulled my tank top over my head and she kissed each nipple and pushed her own breasts tight against me one more time.
I then help her get dressed and teased her with touches and kisses as she’d done me. We nearly tore off our clothes to do it a third time.
Since Kelly was 18 and I was 15, we didn’t become a steady couple. Kelly dated guys her age and I started to make up for lost time with girls my age. But since that night six years ago we still call up each other and get together every so often for another night of Dirty Dancing.
Processing your request, Please wait....
