Story Details

Jenny - Babysitters Wet dream

Wolfsbane20 on Reluctance Stories

This is a story of fiction. I neither condone nor encourage behaviors expressed in these writings.



Here’s my first problem. I am 29 years old and I have always known I liked young girls. But not too young, old enough to be developed but young enough to not be legal and therefore seen as taboo. I have suppressed these feelings as much as I can but sometimes feelings leak out, and when the leak starts its not long until the dam bursts, and when that happens you have a whole lotta problems.



My second problem caused my leak, and subsequently my dam bursting. This problem was Jenny.

Jenny moved in next door to me. I live with my wife and we have 2 young boys. It’s a nice neighborhood, the neighbors are friendly and there are things like book clubs and church fetes regularly. There was a reason I chose this neighborhood though. There were no young girls in it. They had all grown up and moved away from home or they were newborn and totally not my type.



My wife has no idea how I feel about pubescent teenagers. So when I told her I chose this area because of how good it would be for the boys to grow up in, she believed me.

One morning the neighbors who lived on our right were just gone, they had packed up their things in the night and just left. This was very strange for such a nice neighborhood but we thought nothing of it. A month later the house had a SOLD sign on the lawn. We all thought it would be great to have some new neighbors and just carried on with our normal business.



The moving truck arrived a week later, I watched in anticipation as the furniture was unloaded and taken into the house, they appeared to be a young couple, and maybe setting up home in a new neighborhood so they could start a family. All very nice and lovely.



What I didn’t count on is that they had a daughter. Her name is Jenny. She’s 15 years old and she made my heart skip a beat when I first saw her. She is about 5,4 with blonde hair and blue eyes. She has the cutest butt ever, all round and small and she has a wiggle that makes me think she already knows men look at her. Her breasts are just forming, they aren’t huge but sufficient. She wears a training bra and the cutest little outfits that show off her developing womanly curves. I can see that she dresses to impress, and she impressed upon me I can tell you.



I didn’t see much of Jenny over the next couple of weeks while they were setting up their house, but we made friends with her parents who were very nice people. My wife and I had them over for drinks in the evening and we all chatted about the normal things that parents talk about. Boring stuff in other words. Work, shopping, books...yada yada yada. Eventually the topic of children came up, and we told them about our sons and they talked about Jenny. It turns out that I was right in thinking they were a young couple, far too young to have a child of 15. It turns out that she was adopted because her biological mother had left her at 9 years old with her sister and her then boyfriend. They had become the lovely neighbors next door to us.



They told me and my wife that they had not had a night out in 6 years as they had to make sure that Jenny was looked after and not getting into any kind of trouble. My wife did the polite thing and offered to look after Jenny one night so they could go out and have a date night. I obviously thought this was a fantastic idea. I hid my enthusiasm very well. I could tell that this offer struck a chord with her adopted parents.



Over the next month I kept catching tantalizing glimpses of Jenny, she was delectable and I often locked myself in the bathroom and imagined cumming inside of her young sexy body. I had to bite down on my lip to stop myself from crying out in ecstasy as I imagined cumming over her tits and watching her look up at me with a smile on her face and a sexy giggle.



Eventually the offer of babysitting came back to us. They told us that it was their 3 year wedding anniversary next Saturday night and they wanted to go out for a meal and then to a hotel. I knew that my wife would be out of town that weekend with the kids because it was her Mums birthday. (Her Mum didn’t like me, she thought I was a pervert. If only she knew) Knowing she was out of town didn’t stop me from agreeing that I would go into their house and keep an eye on Jenny for them, so that she didn’t get into any trouble. I felt my cock filling with blood at the concept of being around Jenny all night, so close that I could smell her. Taste her.



I went to work that week with a spring in my step. Maybe I should tell you what I do for a living. I work with elderly people in a care home. I feed them, bathe them and administer their medication. I’m not sure when exactly the idea came into my head, but it made me so excited I nearly cum in my pants there. What if I was to steal some strong sleeping pills from work and slip them to Jenny in her glass of milk before bed? This thought excited me so much I went and had a wank in the toilets again. Bashing myself so hard and fast that I thought I was going to explode. And man did I. I cum so hard that it shot out of my hard cock and splashed against the door of the stall I was in. I knew I just had to do it.



Soon the babysitting gig came around. I went over and was introduced to Jenny informally and she smiled at me politely and then went up to her bedroom. Her parents handed her over to me and then they left to go to the restaurant. I was so nervous my legs were shaking. I kept myself busy by sitting and watching the game and having a few beers to gain the courage. Then it got to 9:30 and Jenny finally surfaced.



“Hey kid, dya like football?” I said to her as she came and sat down on the chair opposite me.

“Nah not really. I just wanted to come down and ask if I could have a glass of milk” She smiled at me and my heart quickened, and because my heart quickened my cock got hard faster, I crossed my legs so she couldn’t see and nodded in approval of her glass of milk idea.

“I’ve just got to go brush my teeth. Would you pour it out for me and leave it on the side?” She asked getting up and starting towards the bathroom.

“Sure I will kid”



She wrinkled her nose at me and told me not to call her kid, she’s a woman now. This got my cock harder and harder until it was almost too hard to keep it in my trousers. It hurt like a bitch.



She went to the bathroom and I could finally get up and go make her a glass of milk. I rearranged myself so my cock was down my trouser leg and not so painful or noticeable. First of all I took 2 of the sleeping pills out that I had stolen. I crushed them with a spoon and then poured the powder into her glass and then poured milk on top of it. I mixed it with the spoon after so she couldn’t see that I had put anything into it. Then giving the glass one final longing look I went back into the living room and sat down with my beer and continued watching the football.

I waited in anticipation for 10 minutes before she resurfaced again. She ignored me and went straight to the kitchen to get her glass of milk. I watched in the TV’s reflection as she picked it up and took a deep swig of it. My cock pumped harder. She walked into the lounge and gave me a big milky smile that made my heart thump again. She said goodnight and then went upstairs.



10 minutes later I got up from my chair and slowly noiselessly made my way upstairs to her bedroom. She still slept with a light on so I could see her sleeping body outlined under her thin sheets. Her glass of milk hadn’t even been finished, but she had drunk about 3 quarters of it. I walked into her room silently and stood beside the bed looking into her beautiful sleeping face. She breathed deeply, proving that she was sound asleep. But to make sure I called her name softly, then a little bit louder until finally I was shaking her roughly and shouting her name at the top of my voice. Nothing. Good.



I pulled her covers down first off all, teasing myself with the anticipation, unveiling her body slowly. She wore a tiny vest top, covering her lovely breasts, and riding up over her flat smooth stomach, showing her belly button. She also wore a pair of small pink shorts that made her look so sexy I could have ripped them off right there and then.



I reached out and lifted her vest top up slightly, still cautious so as not to wake the drugged sleeping sex goddess. Her nipple popped out from under her top, all pink and hard. Her breast was smooth and bigger than I remembered. Maybe they had grown. I took a handful of each of them and caressed them. Making her grunt softly in her drugged sleep. I finally slid my hand slowly down her flat sexy stomach to her little shorts. I gripped the waist band and slid them down her slender legs until her full young pussy was released. It was a magnificent sight. She was amazing. I could barely contain myself. I slipped my trousers down and took my raging hard on into hand. I pumped it slowly at first, taking in the entirety of her sleeping body and getting quicker until I felt my balls contracting and filling my cock with cum. I released it and thick streams of cum flew out onto her stomach, covering her in my hot sticky man juice. And still she slept on.



I stood there breathing heavily. I knew tonight was going to be fun.



I looked at her flat stomach moving with her breathing, covered in my hot cum. I was so turned on I didn’t even go soft. I just stayed rock hard throughout.



I looked down at her pussy lips and knew that I had to get my cock in there now. If I didn’t then I would go insane with passion and lust.



I pushed her onto her back, her drugged form still sleeping deeply. I opened her legs wide and positioned myself between them. My cock sticking straight towards her hot young pussy. Begging to be let in.



I inched closer, watching her face all the while, making sure she was deep under before I did what I was going to do. I inched closer to her until I felt my thick hard cock pressed against the opening to her pussy. I pushed and let out a sigh of lust as I felt my head pop inside of her. I slowly pushed deeper until I reached some resistance.



I was expecting this and pulled back slightly and then forced my way through as quick as I could. She cried out in pain in her sleep which made me freeze for a second, my rock hard cock still inside of her. But luckily the pills were still working and she settled back into sleep.



Soon it became easier, her pussy lubricated from her own cum which made me even harder thinking that I was turning this 13 year old on. I pumped in and out of her quicker and quicker, burying my thick hard shaft deep inside of her, my balls were slapping against her ass, and in her sleep she cried out in orgasmic pleasure until finally I felt her shuddering underneath me. I gave myself a congratulatory pat on the back as I realized I had just given her her first orgasm. Her titties were bouncing with my thrusting, and I watched them hungrily, forcing my cock deeper and deeper until my full 7 inches were inside this little teen. I felt my balls contracting and I realized I was going to cum....I pushed into her a couple more times and then forced myself as deep inside of her as I could possibly go.



I released my cum into her tight little pussy, filling her up with my man seed.



I stayed there for about 20 minutes, slowly losing my erection. I loved the feel of her velvety pussy clutching my cock like it never wanted to give it up. Eventually I pulled out and my cum came pouring out with it, it run down her pussy and made a pool on the bed beneath her. This turned me on again and my cock got hard one more time. I moved around to the side of the bed and took myself into hand and started fisting my cock again. I stared at her sleeping face and noticed her mouth was slightly open. This got me wondering if she had ever given a blow job. I figured if she was going to lose her virginity tonight she might as well lose her mouth virginity too.



I knelt onto the bed beside her and pushed my cock towards her mouth. I pushed it to her lips and felt the fantastic sensation as she licked the end of it in an unconscious reaction. I pushed it into her mouth, it slowly opened up as I forced my hard cock into it, until I could feel her sensuous tongue against my rock hard cock. I pushed it deeper until I heard her gag in her sleep, I pushed it deep again and she gagged another time. I loved the sound so I carried on pushing it as deep as I could, listening to this 13 year old sex toy gagging on my rock hard cock. It turned me on so much knowing that she wouldn’t know that she had done all these amazing things.



I felt my balls boiling again not long after this, watching my cock from the outside making her throat bulge and look deformed was so sexy I just couldn’t hold my cum in any longer. I burst again inside of her mouth, making her gag another time. Feeling my cock pump liquid sex into her mouth. I loved the feeling and watching her choking in her sleep, she swallowed as an automatic reaction to the overload of liquid in her mouth and I almost cum again just watching.



I eventually knew that my fun was over and I had to clean her up before she woke up. I cleaned her pussy with some tissue paper from the bathroom and mopped the cum up off of her chest. There was little I could do about the cum left in her mouth but hoped she’d assume it was morning breath or something when she woke up.

I looked at her one more time after I had cleaned her up and knew that I would have these images in my head forever more. I would always remember this night.



Little did I know that I would have a more physical memory of tonight than I imagined.



A few months later I saw her coming out of her house in her school uniform, which still never failed to give me wood. And I noticed something. Her stomach was swollen. I stared at her in lust as I realized what must have happened that night. Over the months I watched her stomach growing and growing until she looked like she was pregnant with quintuplets. On the 15th March this year she gave birth. Not only 2 1 baby, but to twins. She named them Cody and Coral. And she called them her little miracles. If only she knew.

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