Dear Forced Womanhood,
Besides getting away from the stress of their jobs and relaxing, many people use vacations like costume parties and pretend to be someone they aren’t. The meek office worker can be a self-assured CEO of a prosperous company to everyone he meets on his vacation, since most friendships do not continue afterwards, and no one is the wiser. It was on a vacation in the Bahamas that I met Willard, who was pretending to be what he wasn’t, and our relationship continues to this day.
Willard and I checked into the resort hotel at the same time and happened to get adjoining rooms, though we had not met until then. I was taken by his delicate, almost girlish face and slender, small-boned body, and I could see that he was also taken with me, as I am a gorgeous, statuesque, big-busted blonde with a sizeable fortune. Ignoring the advances of the other single, more virile men, I concentrated on Willard and soon had him under my spell. Sunning by the pool, I told him he would make a gorgeous woman, and his dark hair and shorter height would contrast nicely with me. Heads would turn appreciatively when we “girls” walked into a room. He blushed but was intrigued. I had him come to my room that night so I could prove it to him.
I painstakingly did his make-up, put one of my dark wigs on him, and then dressed him in padded bra, panties, garter belt, nylons and 5″ stiletto pumps. He was enthralled, and said it helped him forget who he was and the pressures of his investment business. I’ve always loved binding and dominating men, so I said he would be even more relaxed under the control of someone else, and proceeded to tie him from shoulders to ankles with white sash cords and ball-gagged him. He stayed tied the whole night, with only his gag occasionally removed so he could lick my cunt repeatedly. After a prolonged blow-job, I mounted him before he could cum and then brought us both to a climax. From that night on Willard was my TV sex slave.
Under my urging we moved to a private beach house, where Willard remained in bondage and women’s clothing (from bikinis to dresses) until his vacation was up. Asked to stay, he sheepishly confessed he was only an office worker with a large firm and had saved all year for this vacation. Instead of being angry I was elated and proposed that he quit and be my TV maid and cook. He accepted, and upon returning to my Chicago estate I showed him your magazine and ordered she-male clothing and feminizing creams and pills from your Transvestite and Transformation catalogs. Willard did his housework in wrist and ankle cuffs and chains, a ball or penis gag, and scanty French maid uniform. Afterwards I would bind him with ropes or leather straps in various erotic she-male outfits. He also wore a corset constantly, nipping in his waist and giving his hips and butt a feminine roundness, besides 3″-6″ stiletto heels that firmed his legs and trimmed his ankles. He didn’t object when I kept him tied up at night so that he couldn’t remove the corset or high heels.
His new feminized body was proceeding nicely, taut tits filling an “A” cup bra, when Willard began complaining that his cock was shrinking. I silenced his complaints by binding and gagging him in the cellar/dungeon in only bra, cut-out panties, stay-up nylons and 6″ stiletto sling backs. I suspended him and swung him by his cock and balls and long hair while lashing him with various whips. I walked on his body and stepped on his prick and balls, saying a woman only needed a man’s tongue or fingers on her clit, then screwed his ass with plastic and rubber dildos. Three weeks later Willard gave up and resigned himself to becoming a true she-male. I locked his dwindling penis in an FL4 chastity, increased his usage of pills and creams, and gave him longer hours of female behavior lessons.
Finally Willard’s small cock was locked permanently in an FL2 chastity, ending his sex life, and his tits had large implants. “She” is now Nora, a she-male sex slave beauty who easily passes as a real woman. Bound, I take her places with me, and my girlfriends love dominating her, saying she eats pussy better than a man or real woman. My few male lovers also say that about her blow-jobs. Though I enjoy watching and participating in her abuses by men and women, I prefer our quiet evenings at home, where only I am in charge–and so does Nora.
This letter was originally published in Forced Womanhood 67