Jack and Jill

By Thomas Denny

Published on May 26, 1999

Transgender

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JACK AND JILL

By

Elmo

Jack and Jill, that's what they use to call us. I was Jack, still am, and Jill was my friend Tim. We were only in the seventh grade at the time and I really didn't understand what everybody meant when they called us that. Back in those days I don't think our friends knew exactly what they meant, either. I knew I wasn't a queer or even a sissy boy. And I certainly didn't think Tim was any different than anyone else. Maybe it was because we were best friends and always did things together. Thirty years later, if they knew anything about me at all, I wonder what they would call us. That goes for Tim, too, we're still best friends.

I don't know how we got to be such good friends. Even when we each had girlfriends we would try to make sure the girls were friends with each other. That way we could still hang out together. We even liked the same type of girls. Of course, back then, that would have been any girl that looked good in a short dress and had good legs. There weren't many girls who wore pantyhose but there sure were a lot who were tights. And when I saw a girl with tights on I would fall in love. I don't know what it was that made me feel that way but they did. I would try to hang out in the gym when the cheerleaders would practice. They wore tights that matched the colors of the uniforms. I'd go crazy when they did cartwheels or jumped and could see their butts down to their toes all covered with the same color. Tim felt the same way I did he just didn't talk about it as much.

I should have known something was different about me, though. I used to go home and think about all the girls wearing their tights I couldn't get them out of my mind. And if I were lucky enough to see them wearing a leotard over their tights, well, I'd usually end up having to masturbate. And that would usually clear my mind for at least for ten or fifteen minutes. Then I'd be right back with my fantasies. I finally got up enough nerve to talk to Tim about my problem but he said he felt the same way.

Seventh grade finally ended and summer came and went. The weather had already turned cool by the time the eighth grade started. Of course the girls all had to wear their tights the first day of school. Only this year pantyhose had just started to become the thing to wear. I had already looked at pantyhose in the catalog and knew that I felt the same way about them as I did about tights. Oh the problems of being an over sexed eighth grade boy. We didn't know if the girls wore any underwear with the pantyhose or not. But there was only one way to find out. I had never seen so many boys laying their heads down on their desks and trying to look up girl's dresses. We did come to the conclusion, at least I did, that all girls wore underwear under the pantyhose. That was one of the very first scientific studies that I had ever participated in.

I was starting to find out that seeing all those girls wearing tights or pantyhose was really having an effect on me. One of my friends, that lived a couple of houses down, would wear tights and a leotard almost all of the time. At first I thought Pam must go to dance classes. But I asked her once and she said she didn't take any dance classes. She just liked to wear tights and leotards. She told me they felt so good and were so comfortable she liked to wear them anytime she could. She said her mom was the same way, but I never got the chance to see her mom much. I don't mean she would be outside constantly, in fact she was somewhat of an insider. However, most of the time when she'd come down to see my sister she would have them on with just a shirt over the leotard. My sister was two years older than I was but she and Pam were friends.

Whenever Pam came over I would make a point of hanging around her. Usually I would get her to play Monopoly with me. Just being that close to someone with tights and leotard on would start getting me excited. I'd usually try to get her in a wrestling match. That way I could touch her tights and leotard without being too obvious, but I think she knew what I was doing. We weren't boyfriend or girlfriend but we did fool around with each other. I didn't ever figure out if I liked her because of what she wore or because she let me touch her. I would always like her to come over if no one else was home. Then we could lay down on the bed and kiss and touch each other. But by the time we were through all I had to show for it was a throbbing erection. I made out with a lot of girls but it just didn't turn me on enough if they weren't wearing tights or pantyhose.

Then one day I had this bright idea to sneak in my sister's room and get a pair of tights out of her drawer. No one was home at the time so I didn't worry about getting caught. I took the tights back to my room and pulled my jeans off and pulled the tights on. They were black tights and they were so soft. When I pulled them up and stood in front of the mirror something inside of me came alive and I was never the same. Those tights felt so good on me and they looked even better. The more I moved around and the tights rubbed against my penis the quicker I got an erection. I lay down on my bed and fantasized of being with girls when we both had on tights. I thought I was going to shoot off any minute, so I sat up in the bed. I didn't think my sister would appreciate me getting her tights all sticky.

As soon as I sat up in the bed and swung my feet around on the floor Tim walked through my bedroom door. He looked at me and I looked at him. Neither of us knew what to say. But it was strangely more exciting for someone to see me in tights. I finally stood up and started to take the tights off. But my erection was sticking out so far I would rather him see me in tights than standing there naked with my penis waving in the breeze. The only thing Tim said was "me too". I didn't understand what he meant at first then it hit me. He liked to wear tights, too. "You mean you like to do this too?" I asked him. He shook his head yes. Slowly I could feel the blood leaving my face and my heart slowed down to a normal rate.

I really wanted to see Tim in a pair of tights so I could reach out and touch him and he could touch me. But I didn't say anything. I didn't know how he felt. I sat back down on the bed and started to ask him what he felt like when he wore tights but I didn't get the chance. I heard my sister come in the front door. I told Tim to shut my bedroom door and pulled my jeans on over the tights. I don't know why I didn't just pull the tights off but I didn't. I pulled my socks on over the tights, they were white but the black tights didn't show through, except for the hole in the bottom of my right foot sock. Tim opened the bedroom door and we both walked out to the living room. As I passed my sister's bedroom I looked in to make sure I had closed the drawer. I had, thank goodness.

The only thing wrong with wearing tights under my jeans was that it made it extra tight in the crotch and it was exciting me as the fabric of the tights rubbed against my penis. Tim and I walked outside and talk for a minute. However, I was still too nervous to say much because I didn't want my sister to hear anything. Finally I told him I would see him tomorrow and he left. I went back in the house and sat down on the couch and watched television. I didn't move around too much, I was afraid I might orgasm in my pants. I stayed like that the rest of the night. Finally it was time for bed. I just hoped my sister wouldn't miss the tights. I turned the lights off in my bedroom and took my clothes off except for the tights and crawled in bed. I couldn't get my mind off Tim seeing me like he did. I finally turned over and as soon as I did I came all over the inside of the tights and on the bed. That was one of the most intense orgasms I had. My crotch was so wet I just lay there and went to sleep. It had dried by the time I woke up but the tights were stuck to my skin and I was afraid I would tear them when I pulled them off. It hurt but they didn't tear. Now all I had to do was figure out how to get the sperm out of them.

It was Saturday and I knew I had the whole weekend to clean my sister's tights, so I hid them under the mattress and got up. I wanted to talk to Tim and called him. He was already up and told me he would be over in about an hour. My mom and dad were going someone's house and wouldn't be back till late. And my sister usually went out for the day on Saturday so maybe Tim and I could share our feelings without anyone hearing us. Finally everyone left. Tim wasn't over yet so I decided to wash the tights. All I did was run cold water over them and use some hand soap. It seemed to clean them right up. They didn't even get real wet so I just hung them over the shower curtain rod to dry.

Tim came over and this time knocked on the front door before he walked in. He had one of those grins on his face and I figured and hoped that he had worn a pair of tights. He didn't keep me in suspense for long. After he made sure no one else was home he sat down and took his shoes and socks off and showed me the red tights he had on. I got that feeling down in my groin when I saw the red tights sticking out from under his jeans. "Well," I told him, "you saw me in mine so let me see you in yours." "Aren't you going to wear yours?" He asked with a little disappointment in his voice. I told him I would in a minute. I didn't want to tell him that I had ejaculated in them last night and had to wash them. I didn't want to sound too weird.

He went to my bedroom and pulled his jeans off and shirt, too. All he had on was a tee shirt. He walked back out in the living room. His face was all red when he looked at me, but I didn't notice at first, I was looking at his tights. Then he pulled his tee shirt up and I saw that he was wearing a red leotard over the tights. Before I knew it I was standing next to him trying to get a better look. He looked just like Pam did when she came over. Except that I could see Tim was getting an erection just standing there. I reached out and touched his legs like I would if it were Pam standing there. I realized what I had done and pulled my hand back and looked at him. He said that was okay as long as I put my tights on and he could touch me.

I couldn't stand it any longer. Off to the bathroom I went and dropped my pants and put on the wet tights. Maybe they would dry better if I had them on. I walked back to where Tim was still standing. He stood back a little and put his hand on my butt. It felt like a charge off electricity went up my spine and ended up in my penis. He asked me how they had gotten wet and I had to tell him the truth. I found out it happens to him all the time so I didn't feel so bad. "Does your sister have any leotards?" I didn't know so we went to look. The only thing I could find was a green long sleeve leotard. It didn't match put I put it on. It was tight to say the least. But tight in the right place. It pulled on my crotch just right.

We sat around the living room for awhile looking at each other and talking about what the girls would say if they saw us dressed like we were. After awhile we went to my bedroom and listened to some records. He lay down on his stomach and I couldn't help but see how his butt looked in the leotard. I couldn't help myself, I put my hand on his butt and moved it slowly around. I was scared and excited at the same time. Tim didn't do anything for a few minutes. Then finally he rolled over, quickly, before I could move my hand. Now I had my hand over his crotch. To say that he liked it would be an understatement. I could feel his penis start growing under my hand. I had never felt anyone's penis before. It felt good.

I didn't know what to do next. I moved my fingers around the outline of his penis under the tights. Before long he was breathing hard and pushing his crotch back against my hand. Suddenly my fingers were wet. I could feel his penis pulsating and then I knew he had shot off. I was scared to move my hand until he quit moving. I could feel his sperm coming through the material. I had never felt that before. I pulled my hand away and looked at my fingers. I could see his shiny sperm all over my finger tips. "Taste it," he said. Why not. I put one fingertip up to my lips and tasted. No taste, just sticky.

While I was doing that he had sat up and moved next to me and put his hand on my crotch and started rubbing gently. I didn't know what I was supposed to do so I just lay back on the bed and enjoyed the feeling. I could feel the sperm moving up my penis almost immediately. I didn't know if I should tell him that I was going to cum or just let him be surprised. I don't think he was going to be too surprised because he started rubbing my crotch faster and faster. The feeling of the fabric of the tights and the tightness of the leotard on my penis was too much to handle. I could feel my sperm shooting out and covering the inside of my tights and leotard. I didn't think that feeling was ever going to stop but finally it did. My lips were still sticky from tasting his sperm and I wondered if he was going to do the same.

I relaxed and lay back down in the bed. Next thing I knew he had his head buried in my crotch and I felt licking and sucking all my juices out through the material of my outfit. The combination of his licking and sucking started to tickle so much I had to tell him to stop. We both just lay on the bed for awhile. Neither of us knowing what to say or think about what had just happened. I guess that did explain why they called us Jack and Jill. However, if anyone ever found out what really went on that day they would probably call us worse names.

Tim and I stayed dressed in our tights and leotards the rest of the day. We did have a few more sessions later, but we always stayed in our outfits. I guess neither of us was ready for anything more grownup, yet.

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