It all started when I was 18 years old. I used to hang out with my buddy next door and his sister, Sue. One day I snuck into his sister’s room and looked at, and then tried on, Sue's panties, garter belt and stockings. I then kept them on and went home.
I remember one hot summer day, when I was dressed up in her panties, garter belt, stockings, and wearing some high heels I purchased. I heard a car door slam so I grabbed my clothes and ran downstairs to the basement bathroom.
I just barely got the door closed when I heard Jim, who rented the apartment in our basement, coming down the stairs. But before I could lock the door he yanked it open.
Jim was a big 25 year old man who stood at 6 feet 2 inches tall and weighed 185 pounds. I had fantasies about him and would always wonder what he looked like naked. I would masturbate as I thought about him.
Jim looked at me holding my clothes but also still wearing women's under things. He laughed, and then said, ”I am going to tell everyone I can find, what you are doing.” I was mortified.
Jim said, ”But, if you suck my cock I won’t tell, it will be our little secret. I know you want to, so get down on your knees.”
I was so embarrassed and humiliated but also instantly aroused. My dick was hard as a rock and sticking out of the panties I was wearing.
He grabbed my head and forced me to my knees. He remarked about my cock being hard and took that as a sure sign I was his to command.
I did go to my knees as he instructed. He lowered his pants and pulled down his underwear, and out sprang his massive cock.
My goodness, I thought, it was so big. I guessed it was twice as big as my tiny 4 incher. His balls were huge and hanging down.
He told me to hurry, so I opened my mouth and took his soft cock into my mouth. I sucked and soon it was hard as steel. It was the first cock I had sucked. I guessed I was doing a good job because in only a minute he tensed up, grabbed the back of my head and unleashed a torrent of cum. The blast hit the back of my throat and the force made me gag. But he held me firmly to his cock and I was forced to swallow or choke.
He finished then released my head. I backed away; his beautiful cock slipped from my mouth.
That was when his friend Tom came in. “Holy shit, what the fuck is going on here?”
He saw it all.
From that day on, until I left for college, I was their bitch.
Many times Jim made me watch him fuck his girlfriend. When they were finished, I was ordered to clean her messy pussy and his dripping cock of all traces of their love juices. His girlfriend also would dress me in her girly things. Then she would put me over her knees and spank me for being such a sissy girl. But, what they didn’t understand was that I loved it all.
My only regret was his girlfriend never let me fuck her and Jim never fucked me.
Many years later, after I was married to Ann for one year, we were at a gathering. In private, Tom's now wife Pat asked Ann if she ever caught me wearing her things. Ann said she suspected I was a closet cross dresser but hadn’t caught me.
That night Ann confronted me about my past. She said she wanted to know if I still wanted to do all the things Pat told her I had done as a young man.
I confessed that I still had those desires. I told Ann that I had my own girly things stashed away in the garage. I also told her I dressed up and masturbated when she was out with her girlfriends.
Ann told me to get all my sissy things and dress up for her. I was in shock. I couldn’t believe my luck. I remember quickly going to the garage and getting my things.
Ann told me to strip and put on what I had.
I put on my thigh high black stockings, black panties, black bra and black wig and stood before her.
She ordered me to lie across her knees as she sat on the corner of our bed. She then pulled down my panties and gave me a severe spanking. Then she got mad because the spanking hurt her hand. She told me to get her slipper. She proceeded to spank me again until I was crying and begging her to stop.
She then ordered me to stand. My penis was sticking out just begging for release.
She said I could masturbate onto her leg. It only took a minute before I was squirting my pent up cum. I shot six long ropes of my juice all over her legs. She then told me to lick it all up. I hungrily did as she commanded.
She said the spanking was for keeping my desires from her. Ann told me to never lie or keep anything from her again. I was also ordered to never masturbate unless she gave me her approval.
From that day on I was her sissy. She introduced me to a lifestyle of humiliation. She gradually took lovers and had me service their every need. I became her cuckold, bisexual, cock sucking, cum loving, cross dressing sissy. I couldn’t be happier!
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