The making of a sissy

by Jamie Villa

13 Sep 2018 8224 readers Score 7.1 (65 votes) PDF Mobi ePub Txt


I had two older sister. I remember being dressed like a girl and having makeup and lipstick put on me when I was a boy by my sisters and their friends during their slumber parties. They lavished attention on me and treated me like their doll. I loved it and wanted to be with them always. 

We weren't rich but my parents helped support our grandparents and helped other relatives. So we didn't have a lot of discretionary money. Consequently i had to wear my sisters' hand me downs. I'd wear their shirts and pants anywhere as they weren't too girly. But sometimes my mother would make me wear a dress inside our home if my other clothing needed laundering. My father and older brother would tease me that I made a pretty girl. That's how I learned about getting teased and what wasn't acceptable. I felt I had to object to wearing a dress even though I really didn't mind. My sisters clothing changed to nylon and satin becoming more feminine. I continued to wear their hand me downs inside, included their pj's and even a cute baby doll. Until my father asked why I was wearing a baby doll and said I was too old to wear my sisters clothes anymore.

Several years later when I found a pair of white nylon panties in the laundry. I tried them on and had an erection. I started wearing them in bed and had wet dreams. I was hooked and wore them beneath my clothes and to sleep. I loved the way it felt wearing just panties beneath the sheets. Then one morning my father had to wake my brother and I early (we shared a room) and just yanked my covers down telling me to get up. I quickly pulled my covers back up and he walked out of our room. I hoped he hadn't noticed I was wearing panties. He never said anything and I believe it he did catch sight of the panties I was wearing he probably just assumed they were my normal tidy whities.

My older brother moved away and I had my bedroom to myself. I became bolder, walking to the bathroom in the middle of the night just in panties. I added pantyhose to my sleeping attire. I started going outside in panties and pantyhose. The cool night air felt invigorating on my almost naked body. First just to our doorstep and yard. Later I'd walk down the street hiding in doorways and shadows when a car drove by. One time my sister was away so I borrowed her sheer purple baby doll and panty with matching bedroom slippers. I wore them to bed and it was so exciting I couldn't sleep. I snuck out the front and hid in our doorway. I walked past several houses to the corner then hurried back. It was exhilarating. I walked to the corner again then crossed the street and walked down the next block then turned back. I heard a car and saw headlights. There was nowhere to hide so I ducked behind a parked car. My heart was pounding as the car passed and appeared to slow down. I prayed it wasn't a police car and that they hadn't seen me. The car kept going and I hurried back home.

I wore panties under my pants whenever I could. If I was home alone I'd try on nylons, garter belts, girdles, high heels and make up. I'd always get hard and wet. I tasted my own precum and liked it. I wondered how cum tasted. I was young and limber so I tried to suck my cock while lying on my back with my legs and hips over head. I managed to lick and kiss the tip of my cock and shot my cum into my mouth. But without the sexual tension anymore my desire to try my own cum disappeared. I ran to the bathroom to spit it out. I couldn't understand why I had the desire to taste and swallow my cum whenever I played and edged, yet once I orgasmed it turned me off. Then one time I was in my locked room trying to suck my cock, edging and eating my precum and dripping cum when I went too far and started shooting a load into my mouth. When I finished I sat up and realized I couldn't go to the bathroom because my parents were home. I swallowed my mouthful of cum even though I had no desire. After I did I felt some satisfaction at finally eating my own cum and rather liked the aftertaste. But even though I knew I wanted to and knew I liked it, I still had that reluctance to eat my cum after an orgasm.

by Jamie Villa

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