Well it started out like allot of pantyhose wearers first times. It was when I was young I first tried on my mom's pantyhose. I went into the bathroom and found a pair of my mom's pantyhose in the trash can. They were some tan colored pair of hose. I took my pajama's bottoms off and slipped the hose on over my underwear. They felt so good going on. I went into the living room and sat on the couch and was watching some cartoons rubbing my legs loving how the nylon felt on my legs. After a bit I went into the bathroom and took them off before my mom was going to get up. After that I was hooked on wearing hose.
Did a lot of on an off of wearing my mom's pantyhose. My cross dressing started a few later after that as I was caught by my cousin in her mom's pantyhose and one of my cousin's outfits which was jean skirt pink top with her mom's dark brown pantyhose and dark brown 2 1/2 strappy sandal. She freaked at first but think she kind of liked seeing me dressed up in her clothes. She didn't tell on me or anything she just had me wear some different pantyhose and panties she took from her mom's room as I was going out to lunch with her and her mom and dad. After the lunch we went back to her room for the remainder of the after noon and just played dress up. She ended putting make up on me and dressed me like a cow girl. I thought and so did she that I looked like a cute girl. I felt like one. Anyway we ended the night watching tv in our pantyhose and a night shirt that she had given me. Then we both turned in for the evening I in one room and her in her room. I was so excited to be wearing pantyhose and a night shirt to bed I ended up j/o in them and then had a deep hard sleep. The next morning I woke up and took the pantyhose and night shirt off and put them in my cousin's room and changed back into my underwear and shorts and went back to bed. Fyi the pantyhose I was wearing was another of her mom's pair of hose which were black as was my night shirt my cousin let me sleep in. Well my cousin opened up the door and she came in with the black and dark brown pantyhose and her night shirt and said here take these home with you and you can wear them when you sleep at night. I said are you sure. She said yeah here put them in your bag. I did as her parents were getting up and my mom was coming up to get me and take me back home.
Well that started the itch to my cross dressing. But what did it was when I was about to turn 16yrs old. I got to go stay with my cousin again who was 20 yrs. old now as she was five yrs. younger at the time of her dressing me up. Didn't get to see much of her at the time due to her going to a catholic school where they wear uniforms and such. Well anyways I ended up spending the weekend with them as we were having a family reunion. As I got to her house all I could think of was my pantyhose experience there at their house. I seen my cousin and she had grown as they all do when they get older. She hugged me and asked how I was doing I said good. I really wanted to ask her if she remembered the pantyhose experience but, I didn't want to as I wasn't sure she would remember. FYI my mom didn't find out about my cross dressing or me wearing pantyhose yet.
Anyway after a while when we were done visiting and eating and everyone was either heading to the hotel to sleep or bunking down at the house we all arrived at which there were some sleeping in the basement where their den was and there were some in the room I first stayed at in my pantyhose. I ended up ironically staying with my cousin in her room. As we both went into her bedroom she said you can sleep here where she had another mattress on the floor. As I went into the bathroom and changed into my basketball trunks and tank top and went back into her room. she was sitting on the bed in her tan pantyhose white trunks and a white foot ball jersey which was small so it fit her just right. She said do you still wear pantyhose. I said yes off and on when ever I can from my mom's drawer. She said do you still wear women's clothing I said yes thanks to you I really like wearing women's clothing. She giggled. Well would you like to wear again I said sure. She said here. And gave me some legs black pantyhose. I changed out of my trunks and underwear and put the pantyhose on. She told me that I got better at putting my pantyhose on I said thanks. She said go ahead and pick something out from my closet. I went in and found a dark blue new york Yankees baseball jersey in there I fit it just right as I wasn't that big for a boy as to playing a lot of sports. And put on some of her jean shorts. She was surprised I fit into them. As was I. She said do you still wear make up I said yes and she said lets pretty ourselves up so we were putting on make up together which I was kind of nervous still as my mom was here and so were allot of other relatives and if they came in it would be over for me. After we were done she helped me with some of the finishing touches attention to detail as women seem to do when applying make up. We sat on her bed and ended up talking don't know why we both dressed up in pantyhose just to talk but felt nice, as it was like girl talk.
She told me that she met a guy that she went out with shortly who like to wear pantyhose and that he was bisexual but was more attracted to men when he wore pantyhose. My cousin asked me if I was like that. I said I thinks so as I was feeling more attracted to boys when I would wear pantyhose and get dressed up. She said really that's crazy as that is what he said. I know I don't know why I feel like that but I do. She asked if I ever thought of sucking dick when i was dressed up. I said a few times wondered what it would be like. But didn't know how. She said wait here and she went into the kitchen and came back with 2 banana's. She said here I will show u how. She said here hold it and kiss and lick it with your tong. I started to do it but was kind of giggling as I was cause it felt weird doing this in front of my cousin. She said I know its weird but try to get into it. So I got a little more serious about it and started licking it and kissing it. Then she said now put your mouth over it and start to suck on it as if it were a popsicle but don't use your teeth as that hurts. I knew what she was talking about as a girl I went out with for a short while gave me head and it hurt as she would sometimes use her teeth unintentionally. She said try and use your lips more as u go up and down on it and use your tong when you come up as that makes them feel good. She goes I know as I hear them moan when I do that. She told me to close my eyes and just pretend and I will probably get into it. Well before long she was right. As we were both giving head to our imaginary partners on their banana shafts I started to notice my cousin was starting to play with her self as she had her shorts off. I got turned on by that so I took off my shorts and started to do the same.
Before with both knew it we both came almost about at the same time. Both laying on her bed with cum on our pantyhose. She looked at me. Said never done that before cumming while giving head to a banana. I said me neither I wonder if he enjoyed it. She laughed and said here lets get cleaned up and ready for bed as we have to be up early in the morning. After we cleaned up. She asked if I wanted to wear some pantyhose to bed I said yeah. So she gave me another pair of hose as they were a dark navy pair of pantyhose and a white night shirt to sleep in as she put on her tan pantyhose and a white night shirt as well. And we both climbed into our beds mine on the floor of course. After a bit when I knew she was asleep I started to caress my legs again and thinking of our little banana head giving experience and started to glide my fingers across my hosed cock and imagined being with another man. Caressing my legs and making love to me and me pleasuring him. Next thing I knew I cam which felt so good. I looked up for a second and there was my cousin looking down at me. She smiled and said well was it good for you. I smiled and embarrassed but said yes it was. She smiled again and said good night. And I said good night to her to. And had a good night sleep