My best friend Trevor and I were next door neighbors and grew up together. I remember it was the first day of eighth grade, we got ourselves into a little trouble with his sister, Trudy, but we ended up learning something great.
We got off the bus and as usual went to his house. We found a pile of boxes and stuff in the garage and knew his mom had a clearing out binge and had stuff ready to go to the Salvation Army. Past experience told us we could expect to find some toys and other stuff in there that we were not ready to get rid of so Trevor and I started going through the boxes. We found a box of Trudy's old clothes. Trudy must have been 15 then but these clothes must have been a few years old. Right in the top of the box were some small panties, training bras and other slightly larger bras. We started pulling them out, holding them up to our bodies and making fun of Trudy wearing them. I dared Trevor to try putting on some of her clothes. He hardly ever backed down from a dare so I was sure he would do it. His parents wouldn't be home for hours and Trudy wouldn't get home for another hour after us. Trevor thought about it for less than a minute and agreed, but only if I did it too so I couldn't tell others. I was never as daring as Trevor and was always ashamed of it but this seemed harmless so I agreed.
Trevor was stripping right away. He was never really shy about getting naked in front of me or anyone else at his house. Whenever I slept over, almost every week, he would always walk naked from his room to the bathroom and sometimes all through the house. He never cared if his parents or Trudy saw him. My mom would smack my bare behind if I showed up naked in front of anyone. It was Trevor's and my secret that I would often run around his house naked with him as we were growing up and take baths and showers together and stuff. Trudy would go naked too when we were younger but she stopped when she started getting boobs so we hadn't seen her naked for several years. I was getting a little shy about it around this time myself because I started to grow hair at my penis a few months before. Trevor was always trying to look because he was still bald there. I was a little proud that I had hair but was still embarrassed because even when we had boners, Trevor's was at least an inch longer than mine. His must have been at least 5 1/2 long and mine was still a skinny little 4 1/2 inches and my small bush of hair made it look even smaller. I also felt like a freak because my balls not only hung way down but one hung down way more than the other and was bigger than the other. It was another few months when we had more sex ed that we learned this was normal but then it sort of freaked me out. Trevor just looked normal to me even though he thought he was a freak because he didn't grow any hair till after he was 14. So Trevor gets totally naked, then I, and we are putting on Trudy's panties and bras and making fun of her and stuff. We were holding our penises between our legs so we would look more like a girl and stuffing old socks in the bras. Then Trevor asks me if I would help him put on some of his sister's makeup. Now I think it was really weird but then we were just having fun. We were always doing weird stuff.
We left our clothes in the garage, got a coke out of the fridge (it was the last so we shared) and went up to Trudy's room. His sister never let us in her room so this was part of the fun. We really didn't know what we were doing since boys don't do makeup so as hard as we tried he looked like a drunk hooker run over by a train. Trevor kept trying to get me to put some makeup on but I didn't want to. I was almost ready to give in when we heard Trudy come in the front door and she came up the stairs right away. We lost track of time and were stuck. We never even had time to escape her room so we snuck under her bed. For a girl she was sure messy. Trevor always kept his room neat but Trudy had dirty clothes, old food, messy junk and three inches of dust bunnies. It was really gross.
There really wasn't much room for hiding. It was a single bed and with all the junk we had to lay on our sides, Trevor behind me. He had his arms around my chest and when his sister walked in he started squeezing the cups on the bra and socks I was wearing. I thought he was trying awful hard to make me laugh when we had to be quiet. It was even harder to keep quiet when we could see Trudy start to undress. She turned on a CD and we only saw her feet but we could see her top fall on the floor and then her jeans. This was getting exciting and I could tell Trevor was getting excited too. I could feel him breathing harder and with just the thin material of his sister's panties between us I could feel him getting a boner in the crack of my butt. I was getting one too and I couldn't help holding and rubbing it. Trevor kept teasing me more by pushing and rubbing his boner against my butt. I tried to elbow him but there wasn't room to really move around. We saw Trudy's bra drop on the floor and Trevor let out a little laugh. I was glad Trudy had a CD going. She got her phone and was talking and walking around for five minutes in nothing but her panties and all we could see was her feet.
I kept thinking of our rotten luck. Here was a real live girl that was practically naked, we would even be able to see naked big boobs, bigger than any girl in our class and she was sometimes just inches from us and we could see nothing. It would have been great to just crawl out, surprise her and just get a good look before she chased us out. We would get in trouble but it would be worth it. We never saw a older naked girl before. But how could we run out dressed in her old panties and bras and Trevor with makeup on? We would be in huge trouble, probably get grounded for life and who knows what would happen if Trudy told anyone at school. Our lives would be over.
Trudy stopped talking on the phone and I hoped she would get some clothes on and leave her room so we could sneak out. Trevor was constantly rubbing his boner in my butt and was reaching down trying to grab my boner just to make me try to to laugh. I seriously thought of trying to just get the bra and panties off and run out naked. That would have been better than getting caught in girls underwear but I couldn't unhook the bra without Trevor's help and I couldn't think of how to tell him without risk of his sister hearing us. We could see her sit at her table with all her makeup. We could also see her light blue thong panties. We could see her almost totally bare behind but still nothing in the front. I could barely see her face in the mirror. I was sure we would be caught when she saw her stuff was used but I think she was so messy she never noticed. My heart stopped when I saw her look at the coke on the table. Normally I don't think she would have noticed, there were still some empty and half full glasses of stuff in her room, but the glass Trevor and I had still had ice in it and had water on the outside of the glass. I watched her pick it up, look at it carefully and put it down again. Trudy wasn't the smartest person. I could tell she wondered if there wasn't something wrong about the glass still being cold but wasn't sure. For about three minutes she she picked it up and looked at it the same way three times. I was beginning to wonder if she would actually figure it out. It was getting too much. Trevor and I both had a hard time not laughing our guts out. She finally looked at the glass one more time without even picking it up and yelled out, 'TREVOOOOR!' and ran to the door and out the hall. I guess she realized she was still topless because she came back a few seconds later swearing like mad. I was scared but Trevor couldn't help breaking out and laughing out loud. I tried to tell him to shut up but she heard us and she got on the floor and saw us under the bed. She was really mad and we quickly crawled out the other side of the bed. The bad thing was this was the side away from the door. We were pretty much trapped. We both stood in the corner as far as we could get from her. She stood on the other side of her bed, first angry, then she had a look of sort of shock and then she started laughing.
We couldn't do much except stand there and be laughed at. I was so embarrassed and scared my parents would find out or worse other kids at school. I could see her big boobs shaking at she laughed but somehow it didn't seem so great anymore. Trudy finally stopped laughing enough to ask us what we were doing. Trevor didn't seem as bothered by the whole thing as me and very calmly told her the whole truth about what we did that afternoon. When he got done telling our story she sat on her bed and told us to stand in front of her. I didn't move at first and neither did Trevor. I wasn't real sure of her mood and wasn't sure if she would try to spank us, slap us, or something else. She ordered us a second time to stand in front of her and promised not to tell anyone if we did what she said. We didn't have much choice so we stood in front of her. She got a little smile on her face and she looked at each one of us and then down at her boobs and asked us if we liked what we saw. Trevor was the first to say he did and commented on how big the were compared to the girls in our class. I just agreed with what he said. Trudy then told us that if we had really wanted to see them all we ever had to do was ask. We just said OK. She asked us if we liked dressing up in girls panties and bras. I spoke first and said that we just did it for fun this one time. She asked if I wanted to get out of them and I couldn't say yes fast enough.
I was expecting her to let us go and we could go down in the garage and get our clothes but she told us to get her underwear off right there. I wasn't expecting that but it was better than standing there in girls underwear. Trevor and I turned around and she unhooked the bras. It was then I noticed that Trevor had a boner and was sticking out the panties almost half way. I looked at my own but mine was just sticking straight out, tenting the panties in a sharp little point. A few blond hairs were showing above the panties though and I remembered why I was so shy about nudity. I was about to change my mind and try to bolt for the door when I saw Trevor push his off. I think I hesitated a few seconds more and even before I had a chance Trudy pulled mine off. I covered myself as Trudy ask us to turn around. We did and Trudy looked at us a few seconds and then started to feel Trevor's boner. He just took a step closer and let her feel. She saw us naked many times but she never felt us there before, at least not me. Maybe they played around when they were younger because she told Trevor that it was sure getting bigger and felt harder than it used to. I just got harder watching. She did that a couple minutes and then said it was my turn. By this time I was curious about what it would feel like. Trevor and I played with each others boners when we took baths and showers sometimes when we were younger. Our boners would only get like two inches big then so there wasn't much we could do. We did it a few times the year before too.
I took my hands away and stepped closer. She started to rub her fingers on my boner and made some comment about my having hair and she played with my balls in her other hand. She commented how big they were and asked if I made cum yet. I never saw any so all I could say was that I didn't think so. She said she was surprised because she knew Trevor made cum. Trevor said he didn't but Trudy told him she saw his cum stains in his underwear in the laundry, probably from wet dreams. He replied, 'Is that was that is?' I never saw that happen to him and I remember I wanted to check his underwear when we got up the next time I slept over. The whole time Trudy is still rubbing my boner and balls. It felt so good, like nothing I ever felt before. She asked me if I wanted to see if I could make some cum. I just said I never had any wet dreams. I was kind of jealous and a part of me wanted to go home but I like her rubbing my penis. She told me she knew a way to make it come out.
I knew what jacking off was. Trevor and I tried it a couple times when we were in seventh grade but we got tired and bored before anything happened so we thought it was just stories that kids made up. As dumb as Trudy was I wondered if she really knew or was as gullable as we were for trying. I really didn't care, I was just happy letting her play with my boner and if she wanted to try I wouldn't argue. I told her so and Trevor said he wanted to try too. She told Trevor and me to lay on her bed and she got on with her legs between each of ours. She held a boner in each hand and started to rub up and down. I watched between my boner, Trevor's and Trudy's boobs bouncing up and down. It was great.
It wasn't long before the head of my penis started getting real sensitive and I felt waves of intense pleasure going out all over my body. I couldn't help thrusting my hips up and down with the rhythm of Trudy's fingers. I saw Trevor doing the same. For a second we looked at each other and I thought it should feel weird but it didn't when Trevor grabbed my hand in his and we locked fingers together. I felt like we were sharing each others feelings. It was just a minute more when I felt us both start going over the edge with our first orgasms. We both shot several small but powerful squirts of cum at the same time. They weren't long ropes of cum but the first drops shot onto our chests the rest not past our belly buttons and then just out our penises. I was a little upset that I didn't see it happen since I had my eyes closed the whole time and I didn't expect it.
All three of us took a few minutes looking at and feeling our cum. It was the first time any of us saw it wet, the first time for me at all. Trudy eventually got us tissues and wiped it off. I saw it but it was Trevor who spoke up about a big wet spot in Trudy's panties. I thought she peed but she just said something about getting juicy watching us cum. I think my eyes almost came out when she slipped her panties off. I expected to see a big bush of hair but it was small and thin. I never asked but now I think she must have trimmed it pretty short.
She got the makeup off Trevor's face which looked worse than before. By the time she was done we both had boners again and Trudy let us lay down, this time with her almost bald pussy sitting right on our legs, and she made us cum again. I knew what to expect this time so I watched it happen and I thought it was the coolest thing watching the cum spurt out. Our thighs were covered with the 'juice' from Trudy. We examined the stuff a few minutes and Trudy made us go get a shower.
We ran naked back down to the garage to get the clothes we left laying hours before. We were just pulling our shirts on when the garage door opened and Trevor's mom drives in. I'm not sure what she would have thought if she found just our clothes or us naked and dressing if she came in a few minutes before.
This was our first time but not our last. I was usually too scared to get caught by my mom at home and she was usually home when I was so Trevor and I usually jacked off together after school or when I slept at his house. Sometimes his sister would do it with us and she even let us finger her a few times but she got her driver license soon after that and we didn't see her much. One day Trevor's mom caught us with our hands on each others penises rubbing up and down on the deck after skinny dipping in their pool. We didn't hear her drive up. She didn't yell or anything but said we should do that in his room with the door closed. If she had brought company it would have been embarrassing for them. That was it. Trevor had the coolest parents in the world in my opinion.