tagFirst TimeHalloween Party Sleepover

Halloween Party Sleepover


This is a true story of my first time. I thought some of you would like to hear it.

In high school I went to live with my dad in a different state. I had not seen him for years and he was remarried. My stepmom picked my up from the airport and I noticed she was somewhat dark skinned with a voluptuous body. She had very large beautiful breasts and wasn't afraid to wear really tight shirts.

When we made it to the house I said hello to my dad and we caught up a little. Around four pm the door opened and my stepsister walked in. We were introduced and said hello to each other. She was darker skinned than her mother, her real dad was black. At the time I didn't think of her in any sexual sort of way. Nothing happened for a year. I settled into school, playing sports and making friends.

However, during that first year I started to notice my stepsister more. At night she would wear skimpy nightgowns that barely covered the bottom of her tight ass and had her beautiful tits on display. The top of her nightgowns were either so tight you could see a perfect outline of her tits or they were so loose you had a complete view when she bent over or sat down. After a while I found myself sneaking peeks, especially when she would walk away and I could see her panties.

At the time that all of this happened the VCR was relatively new and we had one. One weekend the parents were away I snuck into their room and found a porno. I took it downstairs and popped into the VCR. For the first time I saw a naked woman suck and fuck a man and it made me crazy with lust. I pulled out my cock and masturbated. It took about 5 seconds. I was going to put the tape back but decided to masturbate a few more times first. (Ahhh youth). So I went about the rest of the day but kept the porno in my room. THe parents wouldn't be back for another day so I thought I'd have a repeat later that night.

Around 10pm I decided to watch the tape again but knew my stepsister was upstairs. I decided to run a cable from the vcr to the tv in my room. It worked and I had some privacy. Soon after I had it up and running she came downstairs. I turned the tv off and listened. I heard her say, "geez, thats funny." She saw the light on the vcr was on and ejected the tape. She didn't know that it was playing in my room.

The next weekend was Halloween and my stepsister was having a party and sleepover. The party went well and most of her friends went home. Two of them stayed. They all slept downstairs in the tv room and watched tv till they fell asleep. My room was also downstairs so I could hear them. Things quieted down and the girls needed more blankets as there were three of them and they had one blanket. I gave them mine and told them two would have to use this one - leaving me with no blanket.

I woke up in the middle of the night and went to look for a blanket as I was cold, but eventually just crawled under the big blanket that my stepsister and her friend were sharing. I was on one side with stepsis in the middle and her friend on the other side. As I was falling asleep I could feel stepsis pushing her ass toward my crotch - as though she was trying to spoon. She was asleep but when she felt me behind her she woke up. My dick was hard and it pressed up against her ass. I was embarrased and turned over to my back so I wasn't poking her. A few minutes later I felt her hand moving across my thigh and onto my cock. It was the first time for both of us.

I decided to put my hand on her ass and it was everything I'd imagined. Firm and shapely. Her nightgown that night wasn't skimpy at all. In fact it was a large fleece that zippered in the front and was knee length of longer. I decided to slide my hand under her gown and feel her thighs and panties. She didn't hesitate until I tried to put my hand in her panties. We were both breathing hard and I had never felt so excited in my life - before or since. I played with her ass and thighs, flat stomach and belly button. I turned toward her to spoon.

By this time her friend was awake and asked what we were doing. Stepsis told her we were having fun. She replied that her parents said she shouldn't do this sort of thing that she would get in trouble. Stepsis told her that she should try it, it felt really good. Her friend wouldn't budge but she decided she liked to watch us explore. Her friend had the biggest tits I had ever seen on a girl with such a small waist and perfect ass. Her mom was pretty big and looking back now I bet she only had a year or two before she would start to get big herself.

I didn't mind if she watched, neither did my stepsis. We didn't do much more that night. When we woke up everyone ate and the girls went home.

My stepmom gave the girls a ride home and me and stepsis were alone in the house. I was asleep and unaware of all this (I made it back to my bedroom before anyone woke up). As I slept I felt something and woke up. My stepsis crawled into bed with me and was rubbing my cock. She kissed me for the first time and I thought I would explode then and there.

I realized we could get in trouble and told her we might get caught. She said her mom was taking the other girls home and that we had 30 minutes alone. Before I could ask if she wanted to try it she laid on her back and pulled her fleece nightgown up to her waist - no panties. I saw my first pussy. I climbed on top of her and tried to enter her pussy with my rock hard cock. It was so tight I stopped because I just couldn't imagine it going in. She told me to try again and put her hands on her pussy as I moved forward. This time the entrance of her pussy was soaking wet. She had pulled her lips apart and guided the tip of my cock into her. It felt so good we both shuddered. I tried to push further but it wouldn't go in. I pushed harder and harder and finally her hymen broke and I went all the way in.

I didn't know what a hymen was but at that point didn't care. She told me to stop and had a pained look on her face. I asked if she was ok and she told me to put it back in. As I did I unzipped her nightgown and sucked on her tits. In less than a minute I came deep inside her. She asked why I finished already and I told her I had no control over it.

We kissed and hurried up and got dressed. When she left the room I noticed there was blood on my sheets.

Later that night we did it again. She told me not to come so fast so I went slow. She closed her eyes and moaned. After a while she told me to go faster. I had to stop a few times so I wouldn't come. She told me that she masturbated often and wanted to have an orgasm. I decided I would try to eat pussy for the first time and apparently I was a quick learner. She had an orgasm and i could feel her tighten up and raise her hips. I had to grab hold of them or she would have bucked my mouth off her pussy. After her orgasm I decided to play around a little down there as I was I had never done it before. She started to orgasm again and I was amazed. I knew I was completely spent when I masturbated and it snd it was exciting to know she could do this twice. It turns out she could do it as many times as I could make her as long as I was down there. After 10 minutes I wanted to come. I asked her if I waited long enough and she said yes - fuck me now. I did and it was awesome.

In the next few months we fucked almost everyday, usually twice a day. We would sneak in a quickie before school in the laundry room and then sneak in a longer session at night while watching TV. We almost got caught a few times.

Anyway, if this story is received well I have many more that are even more interesting - including getting caught and dealing with that. A few erotic encounters right under our parents noses - my stepmom teasing me in her nightgown after she found out about us - etc.. etc. etc..

Hope you like it.

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