October 2nd, 1999
Our Babysitter Zoe
I remember the summer I was 14 like it was yesterday. It was a memorable summer.
Typically when my parents went out, I made a point of being out till 11pm or later, while my younger siblings stayed home with the babysitter. I'll never forget when Zoe showed up at our house. I got the door and just stood there like an idiot, not saying anything, too busy drooling.
That night I stayed out until 10pm. I figured by then the younger ones would be asleep and I'd get time alone with Zoe. Although I was so intimidated by her. She was an older woman. Just the fact a girl like her had said hello when she walked into my home, was enough to make my knees weak. After all she was 16 and a senior. I spent the entire evening sitting in the park, visualising her. First as she was at the door. I saw her in her spaghetti strap camisole, and short button up skirt, and her 4" platforms. Those long tanned legs. Then I was imagining her long straight black hair, draped over her bare shoulders. I thought I even saw her nipples get erect through the camisole.
When I got in, she was watching TV, so I sat down with her to watch the show. I started to glance at her, and I realised that she was sitting in a position that showed more leg. I tried to focus on the TV show but my mind was under her camisole. I wanted to see those perky C cups with erect nipples again.
I just didn't know what to say to her, and then the news came on. At that point she told me it was time for bed, that I should get ready for bed and she'd come and tuck me in.
At that point I figured I'd blown it, so I did as I was told. I went to the bathroom to brush my teeth and do my typical bedtime routine. I stripped and put on some boxer shorts. Then I got into bed, and left just the night table light on. Within a few minutes I heard her footsteps. She walked in and sat on the bed.
She bent forward to give me a goodnight kiss, and I could see right down her camisole. That's when I noticed they were definitely erect. Then she took me by surprise. I'd expected a pretend peck on the cheek like from relatives, but no, she kissed me on the mouth, in fact I was feeling her tongue.
I was a virgin but I wasn't new to French kissing, so I responded to her kiss. I was feeling so blissful. I put my arm around the small of her back at first, and then I decided to get adventurous. I slowly went down to her butt. She had such a cute ass, and I'd been dying to see it naked for a few hours.
She didn't seem to mind and we kissed for a few minutes. Then she sat back up, pulled the bed covers all the way down. She went to close the door, then she came back and pulled down my boxers. My dick was rock hard. I felt so embarrassed to be there naked, while she wasn't naked yet.
Then Zoe got between my legs, kneeled, and kissed my cock. This was like an all-time 14 years old boy's dream. I looked at her kissing my cock, her long hair at times tickling my balls. She looked at me for a brief instant before taking most of the length of my cock in her throat. She had this most mischievous look in her eyes. My breathing started getting louder and I just closed my eyes to enjoy the ride. Her mouth was so warm and I could feel her tongue licking. I just felt like grabbing her by the hair and making her head bob back and forth, but I didn't know if she'd appreciate and I didn't want to compromise this awesome sensation she was giving me. The softness of her mouth and tongue, the warmth of her breath, those popping sounds she made a few times and even the slurping sounds were all contributing to my incredible arousal.
Before I knew it, I felt like I was going to explode. I wasn't sure if I was support to squirt in her mouth, but the sensation took me by surprise and I had no chance to ask. Zoe swallowed everything to the last drop. I felt relieved.
I told her it was awesome and then with my sweetest voice, I asked her if I could touch her chest. She gave me a sultry smile and I slowly pulled up her camisole, enough to see both of her brownish-pink nipple. I felt an erection coming back. I touched each nipple gently with the tip of my finger, caressing in circular motion. I could see Zoe squirm. I then licked her left nipple. She smelled so good and her skin was sweet and salty at the same time. I could suckle at this girl's tit all night.
That's when we heard a car pull in. I went to the window and confirmed it was my parents. Zoe quickly straightened out her clothes before giving me a quick kiss. As she was leaving she told me it wasn't over between us.
I didn't care, my knees were still woozy over the sensation. I looked out the window and saw her going to the car. She looked up and blew me a kiss, before disappearing into my father's BMW.
I heard my mom coming up the stairs, so I got into bed, lay on my side and covered myself with sheets. Told her I was doing some reading, so she kissed me goodnight. I just hoped that my mom couldn't read "Just got first blow job" on my forehead.*****
Two weeks later, my parents went out again, and invited Zoe to baby-sit. I wondered if Zoe and I would get physical again. I wanted her so badly. I had had dreams of losing my virginity to her every night, since the blow job.
I was at my window when Zoe arrived. She was wearing a long flowing skirt and a sleeveless button up front white lace top that showed off her cleavage nicely. I stayed in my room to read, while she readied the little ones for bed, and once they were tucked in she asked me if I wanted to watch some TV with her downstairs.
After placing the baby monitor between my 2 sibling's rooms we went down to the Den in the basement. Zoe sat on the lazy boy and I sat on the couch. She put on Dawson's creek, closed all the lights, and told me to come over, and sit at her feet.
She lifted her skirt, and as it flew up I realised she was wearing no underwear. Was this an invitation? Before I could think, I noticed that I was under the skirt, and she had opened her legs. I could smell her faint scent calling.
I heard Zoe ask me "Have you ever given a girl head".
In a very small voice I answered "No, Zoe, but I'm sure with your guidance I can make you cum".
She told me to use my imagination. I flapped back up the skirt thus exposing her pubic area in clear site. I noticed she had moved back in the lazy boy and had put her legs up in the air, inviting me to explore.
I passed my hand tentatively over the humid muff, through the hair a few times till I thought I found her clit. Then with target in mind, I licked the tip of her clit. Zoe told me to go faster. I did. I licked in every possible direction, at her clit, while she moaned softly. Soon my tongue was aching but I didn't want to let Zoe down. So I went looking for her hole. The entrance was dripping with wetness, so it made the entry of my finger quick. I found a few spots that had Zoe squealing, and tensing up her leg muscles.
I could feel the walls of her vagina tensing up and vibrating around my finger, so I knew she was enjoying it, and angled myself so to lick her at the same time. I went with long laps from her clit to her hole, all while still fingering her.
At one point she pulled away my hand. I thought she wanted me to stop, so I pulled my head away. She grabbed me by the hair and put me right back. I started to lick her again. Now I started to feel her clit quiver and really got into it. My mouth and her clit being one. At some points I had my hands underneath her ass, sometimes caressing her soft firm buns, sometimes squeezing them. At some other point my hands went up to her chest and felt her hard nipples through her blouse.
She then pulled away and said, "listen."
My parents were home. I headed for the bathroom as she straightened out her clothes and went to greet my folks.
I couldn't believe it was midnight already. I'd been giving her head for nearly 2 hours. But to feel her squirm and squeal like that in my arms was well worth it. I wish my parents had stayed out longer that night.*******
It was nearly the end of the summer by the time I saw Zoe again. I'd almost given up. It was one of those scalding hot summer days, I was just wearing bathing trunks. Zoe wore a short sundress that left very little to the imagination. I followed her into the kitchen to tell her I'd be back to watch TV with her later, when she bent in front of me, and I got to see her ass in plain view for the first time.
She wore pink frilly thongs which made her ass look totally bare at first glance. What a nice ass it was too, tanned, perfectly round and toned, and just the right size, I figured 38" hips. The sundress itself was great, it showed off her cleavage, her tiny waist and the roundness of her ass.
I got an immediate hard on, and all I could mutter was "See you for Dawson's Creek".
I went to hang out with my friends, but all I could see was her naked butt. I wanted to brag to my buddies that I'd got a blow job from the babysitter, but somehow it just didn't feel right. Besides if I told the guys they'd all want to come back to my place, and ruin it for me.
I got home just as the show began. I closed the light and sat next to her on the couch. I decided to rub my face in her chest to see how she'd react. It was liked she was purring, so I started to unbutton her dress and free those breasts I never fully got a chance to explore.
I kissed each breast, all around them, and every single inch around her chest. Then as a baby lying on her lap I sucked on her nipple, while playing with the other breast with my hand. She was one hot mama. I was just sizzling.
It dawned on her that I'd never seen her naked and finished unbuttoning her dress. Then I pulled down her thongs. I pushed her on the couch and proceeded to kiss her and lick her everywhere. Once she was turned on enough, I kneeled in front of her face and rubbed my dick against it. Each time it would pass near her mouth she'd kiss it.
Then with my dick, I rubbed each of her breasts, and then moved down her stomach. I went around her belly twice, and slowly moved it towards her clit. There wasn't enough moisture, so I rubbed it near her cunt, then back to her clit. Then back and forth between her cunt and her clit, until she was quite wet, then slowly I started to put my dick in her cunt.
My mind raced, this was the moment I'd been waiting for. A moment I'd never forget. Our bodies danced in rhythm and slowly I slid into her. That tight warmth, similar yet different then the sensation of a blow job. I kept pulling in and out slowly. But she wanted it otherwise. She rolled over on top of me, and rode me like there was no tomorrow. Till the sweat was dripping down her chest. When I noticed that she was slowing down, I put my hands on her hips and helped her bounce back and forth on me. I ever managed to counter the movement with mine.
The more I bounced her up and down, the more she started to moan loudly. I was hoping that my little brothers and sisters couldn't hear, but that made it the more exciting. That we had a chance of getting caught, fucking our brains out on my parents couch.
After a while she just lay on top of me, so I rolled back on top of her, and then squatted. It was an interesting angle which seemed to work for her too, as she squirmed and moan, and I could rub her clit at the same time with my hands.
I'd masturbated 5 or 6 times that day thinking about Zoe so I kept going for some time, long enough to give Zoe the opportunity to come over and over for a while there. I'd seen all sorts of positions in magazines, and here was a girl willing to just keep going. For a while I tried every position with her on the bottom.
I had her lie on her stomach, with a pillow right under her pelvic area. I knelt behind her, and had her bend her knees. That was a great angle. I could view her cute ass as I rammed my cock inside of her.
Then for a little while I lay on top of her while she was lying on her stomach, until it slipped out for the 10th time, and I felt she was losing her orgasms. She got back on her back and I tried the missionary position for a bit but got the feeling I was crushing her more then anything else.
The best was the one I came in. Zoe was quite flexible. She had her legs folded back so that her feet were on either side of her head. I held them down as I banged her in that position. I was so close to coming that I banged her real hard, and the harder I rammed it in the louder she moaned. Until finally the sensation got the better of me, and I came. I'd never come in a woman before, each time I squirted I felt her cunt tightening around my tool, which would made me squirt some more, until it was over. I even grunted. I'm not sure if Zoe or I were more startled.
We just lay there for a few minutes to catch our breath, and then slowly untangled from each other. I put my shorts back on and she got dressed, and cuddled together to watch TV.
My parents woke us up when they came home at 3:30, my dad telling me how sweet it was that I kept the sitter company. Zoe smiled and said I was wonderful company, and winked at me.
After that every time she'd baby-sit the kids, we'd have wild sex in some part of the house. It was our secret. It only stopped when she went to college and moved out of town. I always wondered what became of Zoe.
Finished: October 24, 1999
Lovecraft Productions (c) 1999