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Sheila

Sheila

Lives in United States · Born on October 6, 1953
ABOUT ME
A lifelong transvestite I started by wearing my mother’s clothes, abusing my genitals, sticking objects up my ass and masturbating.

When I was in junior high school I started stealing clothes (bras, panties, girdle and slips) and keeping them hidden for future use. About the same time I started giving myself enemas – another lifelong favorite.

My first homosexual encounter was at 14. I told one of my friends I liked to dress in girl’s clothes and he wanted to see me. I didn’t really understand the danger so I was giddy with anticipation. I laid out panties, a 36C bra, a yellow cotton sundress and a pair of my mother’s shoes.

He wanted to watch me take an .... I asked him to put the tube in me and release the solution. I was naked with a rock hard erection. He watched as I expelled the fluid and got dressed in my girl clothes. He had an obvious erection and I was fascinated with my effect on him.

My offer to suck his cock was eagerly accepted and he came in my mouth so fast I almost lost his load. For several months until my family moved, he used my mouth and finally my pussy. I let him crawl up under my skirts a couple of times, but I was much more pleased to assume the female role and serve him.

After I got my own place and started working, a cycle emerged. I would buy clothes, shave my body and cruise for a willing partner. My face didn’t pass, so I made no effort to wear makeup. Short affairs with men were followed by remorse. I’d throw away my girl clothes and swear never to dress up again.

Within ninety days the cycle would begin again. Shaving my legs followed a nice warm bath and an .... I bought or stole panties, a bra and a girdle with garters. I wore hose and bought high heels. I liked skirts and blouses, but occasionally I wore a dress. I had success with men two or three times a year and each affair would last a couple of weeks. I enjoyed being spanked and humiliated, but these activities triggered remorse that usually stopped the cycle.

I married in the hope that would put all this behind me, but it didn’t. I asked my wife to allow me to dress as a woman and she did. I reveled in the role of lesbian lover, kept my body shaved and wore woman’s underwear under my male clothes. I had no outside affairs and this routine lasted for several years.

Children and disdain on my wife’s part led her to insist that I stop all my transsexual activity. I honored her demands, but it only served to drive me underground. When I traveled out of town I had a special extra suitcase. When the wife was out of town with the kids, I spent the time dressed and looking for sex. During this time I managed relationships with two women and six men. BDSM dominated this phase of my development. I was branded once and I often forced to pierce my own nipples. I insisted on being bound and spanked and I took great pleasure sucking cocks in public places and being seen in public as a male in female clothes.

I was very fortunate not to be discovered, exposed and ruined during these crazy encounters. It was truly insane.

After the last ... left home, things changed again. As one of her birthday presents a couple of years ago, I gave my wife a CB3000 cock restraint. Dread and anticipation flooded me as she opened it. My wait was short. She slapped me hard, called me a wimp and told me to get on my knees. She walked around describing in great detail my future as her maid and cuckold. At her command I stripped and she installed the restraint. My initial abstinence would be sixty days. I was assigned chores, but there was no mention of female clothing.

My wife offered me several presents to celebrate my 60-days of restraint. She removed the CB2000 and said I could masturbate or I could have the presents. I begged her to tell me what was in the boxes, but to no avail. In the end, I took the presents hoping to masturbate later. Before I was allowed to open the presents my wife told me to masturbate and eat my own cum. She then put the restraint in place and said it would be for ninety days.

My gifts were worth every humiliation. It was a maid outfit but so much more. A corset, mastectomy pads, mesh hose, sandals with 6’ heels. It was heavenly.

Slowly my life of service evolved. Today I only service my wife’s pussy with my mouth. She found out about my ... fetish and insists I take one daily. After one such cleaning she handed me a tampon and told me to wear it. She assigned the first week of every month is my "period". I wear a tampon and Kotex (with belt) every day and change them out four times a day.

She took me to the mall and had my ears pierced. She had a beautiful, colorful tattoo of a butterfly put on my right shoulder. My only underwear is panties and camisoles. Over time my pants became woman's slacks and my shirts became blouses. At her discretion camisoles often give way to braziers that are obvious under my sheer blouses. My footwear regularly has small heels and open toes that show off my painted toes

I can no longer work a normal job so she arranged for me to work in a beauty Solon. My hair has grown out and electrolysis had solved all my problems with body hair. My hormone regiment has made little difference so far, but I'm sure it will

It had taken years, but I am now the subservient spouse my wife apparently always wanted. So far she has concealed my condition from our family and close friends by allowing me some latitude in my dress around them.

Her close girl friends know and play a role in my humiliation. Dressed as a French maid, I routinely answer the door to find a handsome man standing there.

My role in my wife's lovemaking is simple and very rewarding. I serve her and her lover meals or drinks. I undress the men and get their cocks ready. Occasionally I rim their ass or give him a blow job. After she is fucked, I'm always allowed to clean my wife's cunt. Every couple of weeks she restrains me, goes out and brings me back a nice warm cream pie.

My wife travels some and that affords me a few flings with a dominant man during the year. I also sneak in a "quickie" with one of them when I'm supposed to be at work, but I'm paranoid about her catching me and ruining my perfect life so my extra curricular activities are very limited.
Basic Info
Rating:
1 Ratings
Gender:
Age:
October 6, 1953
Location:
Last Login:
October 22, 2011
Member Since:
September 13, 2010
Membership:
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