Where it happened: My parent's bedroom
I am the oldest child in my family. I have a younger sister and brother my sister is now nine and my brother is 20. At the time my sister was a baby and my brother was twelve. Well enough of the background detail let me get to the story. My parents went out of town for the weekend to our summer house in Vermont. Instead of trusting me with a one year old baby and my younger brother my parents asked a girl(She was a senior in high school) who lived down the street with us to stay over for the weekend. Our parents were good friends and my parents were rich and I’m sure they were going to pay her well so she said yes. (I would rather not give her name) My parenst left friday afternoon and were due back sunday. Well Friday night me, my brother, and our babysitter played monopoly (my sister had already been put to bed) We were all three in our pajamas the babysitter was laying on her stomach with her shirt hanging down. She wasn’t wearing a bra and i could see her tits hanging down. i tried not to look because at first i was embarassed but i kept staring. Finally she saw me staring and she sat upright so i couldn’t see anymore. I was completely embarrassed but she was pretty cool about it. Well any way we played monopoly until late into the night and finally my brother got sleepy. I didn’t want to go to sleep because although I was 14 i was real shy around girls and i had never had a girlfriend or even talked with a girl but while we were playing monopoly me and the babysitter(I’ll call her Sue) had a great time joking around despite the one breast incident. So we all went of tho bed in great moods. I had just recently started experimenting with masturbation and i decided that I would go to my room and msturbate. Well it took me about five minutes to take care of business(i was extremely horny from the previous incident). Well i got out of my room to go clean up in the bathroom and i heard the bath tub in my parents bathroom running. Our house has a balcony upstairs that wraps around the whole house and I decided,still horny from seeing my first set of tits, to go peep at her through the window. The only problem was that the door to the balcony was in my parents room. Well anyway I went out on the balcony and watched her through the window. It was the first time I had ever seen a naked girl. I watched as she lifted each leg and scrubbed each one. I watched he rub her tits down with soap. She had a vary nice body. She then got out of the tub and pranced around naked in front of the full sized mirror. she stood sideways and checked out her ass and breast profile. Then she kissed the mirror like it was a guy. I couldn’t believe my eyes. I just stood there in amazement as she toweled of and put on her pajama top with no panties! As she left the bathroom and went to get into bed i realized that i had a problem. I was stuck out on the balcony! If i went in she would no something was up. I decided to wait on the balcony until she was asleep. After waiting what seemed like forever but was really more like 30 minutes i decided it was safe. I slowly eased the balcony door open and squeeze in the room. I looked at “Sue” in the bed from what i could tell she was asleep. She didn’t make any movements as i walked toward the bed to go out the door. As i aproached the bed i noticed that her legs and waist were out form under the covers. My heart began to pound at the thought of seeing her up close. I decided that i would just lift her pajamas up enough to where i could see he special place and then if anything happend i could make it easily out the door. I neared the bed and slowly reached down to pull upt he pajama top to reveal her sweet spot. As soon as it was uncovered and in the night air Sue kind of wiggled causing me to make a break for the door. At the doorway i looked back and noticed she was still sleeping soundly and the sight of her pussy made me incredibly horny. Again i decided i would just go and touch it and if it woke he i would run for the door. I approached her and slowly put my hand on the hairy part of her pussy and moved down ever so slowly. As I did this her legs spread ever so slightly and i heard her take a heavy breathe, but her eyes were still closed. With her legs spread i got a good look at the insided of her pussy and not knowing what i was doing decided to stick my finger in the slit. As i did this Sue began to really breathe hard and i became very dizzy and out of breathe from being so nervous. I finally decided to give her pussy a kiss(i had heard my friends talk about this). I bent my head down and laid a big kiss on her slit, tongue and all. When i did this she mumbled something, rolled over, and pulled her pajama top down. I will never forget the sweet taste in my mouth. But fearing that i had waken her i ran for the door once agian stopping, looking back, and seeing that she was still apparently asleep felt relieved and decided not to push my luck with getting caught so i went to my room. Needless to say i needed to masturbate agian and after this i felt very guilty for what i had done. I had trouble sleeping that night. The next day we jsut stayed around the house. Sue didn’t say anything about the night before but she was acting differently. She was making fun of me, joking with me, and wrestling with me. I didn’t realize it back then but she was flirting with me. Night rolled around and my brother was spending the night with the neighbors. Sue and I watched T.V. until late that night. Finally Sue said it was bed time and she turned of the t.v. She went to get the cookies she had made and some milk. As we sat down stairs eating she asked if i had a girlfriend and i said no. She said i was very cute and asked if i had ever been with a girl. I said no. She asked how would I know what to do when i finally was with a girl. I told her i didn’t know. I was really uncomfortable with the line of questioning. She asked if i would like her to show me how to treat a girl. I didn’t know what to say so i just laughed and said yeah right. She unbuttoned her shirt and said she was serious. I stood there amazed not knowing what to do. she told me to come over there and take her shirt off, and then take her bra off. I did. Then she told me to feel her tits and then suck on them especially the nipples. She would say “harder” or “softer” or use “your tongue more” to help me along. Then she told me to pull of he shorts and rub her panties for a while. I did and i noticed that they were getting wet. She said “that is what is supposed to happen you’re doing good”. Then she told me to take her panties off. I was in a state of pure amazement throughout the whole session and i did everything she told me. She was laying on the couch completely naked. She told me where to rub on her pussy and as i did this she closed her eyes and put her head back. Her hand came over the top of mine and rubbed her for me. Her hips thrusted towards me with each stroke. She started shaking and moaning. I didn’t know what was happening so i took my hand away she grabbed it and pushed herself onto it and said don’t stop. After this she asked me to take my pants off. I was embarassed because i had already nutted on myself and I didn’t know how big my dick was compared to the highschool guys. so i didn’t do it. She asked what i was waiting on and then unbuttoned my pants and pulled otu my penis. She too it in her hand and started stroking it up and down but she was very rough and i said “Ouch” she realized that i didn’t like it and sd she took my hand, laid on her back on the couch and put he legs up in the air. She pulled me on top of her and said “put it in me”. I was scared at this point even though i didn’t know much about sex from experience i did have sex ed and i knew i needed a condom. catching my breath I said “don’t i need something” . She responded soomething that i didn’t fully understand about her cycles and that now she wouldn’t get pregnant. I was still afraid but i had never wanted anything so bad in my liffe so I grabbed my dick and put it near her pussy but i could find how to get in. She smiled at this and then grabbed my penis and guided it into her. I will never forget this feeling, it felt as though my body was completely surrounded by warmth. I began to pump in and out and after five pumps i exploded inside her. I apologized for not lasting very long but she said she thought it was sweet. We laid together for about an hour and then we both went to bed. I was so excited about my new found knowledge. The next Sue acted like she had the day before and when my parents came how and Sue left i never talked to her that much again. I found out later that Sue had broken up with her boyfriend the week before that weekend and she must have been feeling real depressed. Now that i look back on it i feel bad for how i took advantage and about the fact that i lost my virginity to someone i didn’t really have anything going with. A WORD OF ADVICE TO ALL YOU VIRGINS READING THIS: SAVE YOURSELF FOR SOMEONE SPECIAL BECAUSE ONCE YOU HAVE LOST YOUR VIRGINITY YOU CAN NEVER GET IT BACK!