Becoming a Sissyboy

Story by Candy on 1 Mar 2010

Readers: 11689 Score: 4.0 (31 votes) PDF

One day I came across a pair of my mom's sheer pantyhose in her clothes after she had done our laundry. As I was ready to take them to her room, I touched them and realized they felt so smooth and tingly. I wondered: 'do women wear them because they like how they feel?' With nobody around on this Saturday morning, I decided to find out. Quickly, I got naked on my bed and rolled up the hose like I had seen done in a movie. Slipping them on all the way up to my slim waist, I was entranced.

My young cock got aroused instantly and got rock-hard, straining against the sheer material. I rubbed my cock inside the hose, getting hotter and hotter. I let my hands roam all over my hose covered legs, thighs, crotch and behind. It was nothing less than very exciting and stimulating. In a short time, I was cumming hard, staining the hose with my cum, and I moaned in ecstasy. I hadn't had an orgasm to date that felt so good. This was the start of something that would be with me for life. I washed the cum out and set the hose to dry in my shower.

That night, my best friend Corey was over for a sleepover. I wrestled with telling him about what I had discovered. How would I tell him, what would he think? It felt so good, I had to tell my friend about my discovery, I just had to. Late into the night, Corey and I were getting ready to go to sleep. I mustered up the courage - a lump in my throat, I told Corey that I had a secret, something he had to promise not to tell - anyone. Corey promised, and I spent the next few minutes telling him about my new-found, pantyhose pleasure.

Corey was stunned, I was afraid that I might have freaked him out. I had hoped that Corey would understand. Corey surprised me an awful lot by saying that he also had wondered how they felt but had never tried them himself. Now I felt much better and safe, he wouldn't tell a soul, in fact if I played this right he would be my lifetime accomplice. He asked me if there was some way he could try some on. I said it wouldn't be a problem. I snuck down to the laundry room and took another pair of my mom's hose from the just washed pile and made it back to my room.

Corey and I stripped naked, Corey watched as I put mine on and I helped Corey put his on. Both of us were wearing pantyhose now and loved the feel and excitement. Corey and I talked about how good it felt to wear them and our curiosity lead to touching each others legs in hose. We couldn't hide the erect reaction our young cocks had to this stimulation, both were hard and neither of us tried to hide it as we continued to feel all over each others legs with excited hands. Corey was more daring to my delight. We both stood up to look at each other in the mirror and were turned on by what we saw. Our legs, thighs and bums nicely packaged in sheer nylon and our bulging cocks tenting the front.

Corey got behind me and rubbed his hose covered cock against my behind. I told Corey how good it felt and Corey moved his hips around and guided his hosed cock to my ass slit moving it up and down as if he were trying to get in. We both moaned in pleasure as we played together. Corey was grinding his cock in hose on me, his best buddy's behind and we both loved it. Corey's hands reached around and started to rub my cock in hose, as if wanking me. It was pure heaven for both of us. Corey then whispered to me that he thought that we were both sissy boys -- and that sissy's do gay things.

I turned to face Corey and we hugged...young cocks rubbing together. We gently kissed each other, with no experience, we pecked and pecked our lips as we humped each other face to face and held each other by our waists. I said to Corey that I wanted more. Corey said he did too. With that, I slipped to his knees and started kissing Corey's cock in hose. Corey groaned, his hands on my head, holding it close as my mouth tried to cover Corey's hosed cock. Licking and sucking, I worked on Corey's cock out of pure lust. Feelings we never knew we had, had come to the surface with both of us in hose. Corey pulled his hose down and his young cock sprang out, hitting me in the cheek. I then licked his cock-head, sending Corey into ecstasy.

We were both discovering and enjoying hot sissy boy sex as I sucked on my buddy's cock. Corey started thrusting his hips, his cock coming in and out of my hungry mouth. I sucked and licked it and Corey lost control of himself. He didn't last long as the pleasure was too much. He came and filled my mouth. I tried, and took in as much as I could and finally swallowed his thick creamy sweet cum.

Corey laughed and said I was a cocksucker -- a sissy cocksucker. With a wry smile, I went to the edge of his bed, sat down facing Corey and said it was his turn to 'join the club'. Corey walked over, sank to his knees and began kissing my pantied cock -- figuring he owed his friend. Corey realized that sucking on a cock was as big turn on as being sucked. He was already hard again after a minute of going down on me. In short order, Corey had freed my hosed cock and was trying to suck it down. I came coating Corey's throat with my boy juice and the two of became officially sissy buddies.

That night we slept together in one bed in our pantyhose kissing and hugging each other till we fell asleep in each others arms. In the morning he woke me up and we kissed and hugged again and played with each others bodies in hose till we came. We showered together and putting on the hose beneath our street clothes went down for breakfast. This was the start of our first sissy weekend together, in the coming months we became bolder and did more to feel the full pleasure of being sissy buddies and an even longer sissy relationship we two buddies would keep till we got out of college together.

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