Good....Lord.
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NSFW WARNING
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When I hit puberty I found that I had an attraction to crossdressing. I had my sessions, just feeling silk stockings and panties. But it wasn't enough. Eventually I had sessions wearing them. Wearing bras, stuffed with socks, wearing them under my clothes. I wasn't going to steal them, so I bought my own pairs. It was always "running errands" when they went down the aisle at the stores. Occasionally I would buy pairs of men's underwear or pants to play the alibi. I would shave my legs and tell my mother I was taking up swimming at school.
Initially, I was ashamed of my penis. I thought "I'm a woman inside, not a man." Then I realized the whole reason I felt the need to do this was to get off. So everytime I'd step inside a pair, I always found myself getting hard. The breaking point was one day, while wearing panties, stockings, and a skirt, hard inside, visible bulge in the skirt, I felt hard, confined inside. I bent down and up and felt rubbing inside. The rubbing felt good. I kept bending up and down until I finally felt some sort of material leaving my groin area. The release felt amazing, like nothing else. My penis felt sticky. I pulled everything off and found white liquid on the panties. My beautiful pink, silky panties soiled by this liquid. It smelled strange, and I found myself tasting it. It was sweet. I lapped it all off and swallowed it down.
It wasn't enough though. Eventually I started buying dresses. Expensive, elgant ones. I had difficulty tying the corsets myself, but I could get it done. I found myself always getting hard and uncomfortable until the release. I took it a step farther when I used a maid's uniform and started cleaning the house. I would use older cleaning utensils to feminize myself in a more traditional fashion, wearing high heels and doing my own makeup. Then I decided I would try it out in public. At first I began wearing underclothes to gain comfortability. Then I started to adopt full feminine attire, even chastising myself with a device to prevent myself from getting "an erection" as they say and not only feeling uncomfortable but perhaps compromising myself.
Where was the fun in that? There was no danger unless there was the chance I could be noticed and humiliated. So I began to train myself, occasionally I would purposely work myself off just so people would notice the bulge and stain.
I had gone to college enrolled as a female named Jessica. I brought my shameful men's clothing only if I was going to see family or friends outside of college. I had lived covering this for years. I lived off campus in an apartment, and there would be nobody who would know but anyone who wanted to do research. There was no reason to ever do any research because I passed off so well. There were both guys and girls who were always looking at me. Guys would ask me out, try to get to know me. So would girls. There was one in particular who I had made friends with, Kristin. I knew she "liked" me but I never paid attention to it. There was a moment after studying where she took me aside and kissed. I held the kiss, only because she was so fucking beautiful and I wasn't letting this go. The issue arose when I realized she started to undo my dress at the back. That's enough, Kristin... but she only began undoing faster, while groping my butt. What would happen if she undid the dress and blouse and found the boobs were fake? Or worse, what would happen if she felt the groin area up and found.... oh God....
As she undid the dress, she held onto me tight. I realized there was really nowhere I could go now. suddenly the panties got tight. No... not the time...
Suddenly she undid the bra and she felt my fake breasts. The suction broke and they fell off. I immediately covered my eyes in shame. She would find me out. She would tell everyone. I would be so fucking screwed.
"Jessica?" She asked.
"Yes?" I mumbled.
"you don't have to be ashamed. My sister growing up didn't develop hers until she was about 19. She didn't wear fake ones, and often had to deal with being called flat by a lot of friends and peers. But you don't have to be ashamed of it."
"Sigh... okay..." Oh my god. I was saved. I was fine. I was safe. She didn't find out. I was off the hook and there was nothing stopping this. Now I just had to get out of this situation and...
She said in a very seductive tone while smiling, "Now, where were we?"
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