This is a print version of story POP GOES THE CHERRY by littleoralvee from



I recently read a delightful account of a young gurl loosing her virginity to a f****y friend. Got me thinking about loosing my own virginity.

First, you should know, my mother made me a sissy. She took great delight in dressing me as a little girl, thinking back I can not remember when she did not. We lived in the country and most of the time growing up I played outside with my dolls in dresses. The only time I wore little boy’s clothing was when f****y visited or I went to school.

Everyone in town knew I was a very sissy acting little boy. I was bullied a lot by other boys, shunned by the girls, pitted by the teachers and talked about by the others in the little city where we lived.

Summertime was the best time as I could be totally Vanessa. Mother would be at the dinner, waitressing and I would be home alone. I was fifteen, home one rainy summer morning playing in my mother’s make up. Earlier I had slipped into one of her full length open bottom girdles and a pair of tan seemed nylons. I attached the six garters with great care making sure the dark seems were straight as arrows; as mother had taught me. My toes and nails painted bright red as they had been since school let out for the summer. Cleopatra would have been proud of my eye makeup. I had just finished painting my lips candy apple red, when I heard a man clear his throat in the bedroom door.
Startled I turn and saw my uncle Bob standing blocking the door. He was my mother’s older b*****r and had stopped by to say hello. He had been by the dinner and mother had told him to stop by and check on me on his way out of town. So engulfed in applying my makeup and the rain tapping on the roof, I had not heard him drive up or enter the house.

He broke the awkward monument telling me to stand up and turn around so he could see what a pretty gurl I was. I did as told to scared not to comply with his demand. By the time I made a complete turn around my had got hard and making a small bulge just above the bottom opening of the girdle. I was so aroused having been caught by a man dressed a Vanessa.

Uncle Bob crossed the room his eyes on my bulge and his hands fumbling with his pant’s zipper. He told me we both seemed to have the same problem. With one hand he pulled my cock out the bottom of my girdle and from his pants his rock hard cock. The touch of a man’s hand on my little cock made it shoot gobs of cum on the floor. I tried to pull away but his hand on the back of head and firm grip on my cock made it impossible. Embarrassed and humiliated I started to softly sob.

He asked me if I had ever ejaculated before and I told him yes, but never so quickly. Then he asked me if his s****r had ever given me a hand job. I confessed that at about twelve when I started getting erections mother had shown me how to masturbate.

He moved me to the bed and made me sit down, taking his hands off me long enough to remove his pants and underwear. Sitting next me his dick semi-hard he told how when my mother was about my age he had broke her cherry and that he was going to take my virginity on this rainy summer morning. That said he gave me some instructions to due. As I got up comply he gave me a very hard smack on my ass which left his hand print and he laded back on the bed.

I when to the closet and put on a pair of red open toed red five inch pumps. Then to the bathroom for baby oil and a towel as instructed. Returning to the bedroom, my heels clicking on the wood floors, I could not believe excited and scared I was at the same time. I had just learned that my mother was a slut and the man that took her virginity was about to take mine. I was washed over with the thought that I hoped her b*****r found me as pleasing as he had his s****r, my mother.

Once back in the bedroom, I got down on my knees and began sucking my uncle’s cock. It was rock hard and soon he stood up tell me to do the same. The towel was place on the bed and I was told to lay on top of it. As he lubed his cock with baby oil he told me I need to work on my cock sucking. He pulled my virgin ass to the edge of the bed, placed my legs on his shoulders as he lubed my asshole with baby oil.

I felt the head of his cock press against my hole but it did not penetrate me. More baby oil applied and again his mushroom hood was at my hole. Uncle Bob pressed harder and then with one swift thrust of his hips he buried his shaft to his balls. I took my breath way and flashes of white lights danced in my eyes. I screamed and screamed again for him to get his cock out of me, but he did not remove it leaving it buried to his balls in me.

In a few minutes the pain subsided and he asked me how it felt not to be a virgin any more. Before I could answer he started fucking me like a steam engine. Slow long strokes as his piston started moving in my cylinder until it was moving fasted than a speeding bullet. Soon I felt his warm cum fill my bowels and the weight of his body lift from my body. I ask him was I good but he never answered.

I laid there on the bed as he washed his cock off in the bathroom returning to the room throwing me a wet wash rag tell me to clean myself. He told me he would stop by every week as he had lots to teach me and I had lots to learn. I laid there on the bed and cried. Realizing I was not a normal boy nor would I every be nothing but a sissy slut.

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