from Jean

Dear Helga,

Thanks for replying again. I am very happy to share this with you and your readers. I will try to reply to some of your questions.

My sister is very cruel to my sissy husband due to the fact when I first met Anthony she didn't like him and they never got along. It's funny because everyone else my parents, my brother and my younger sister all love him. She is sort of the ugly duckling in the family (Pardon my expression). I feel it has a lot to do with jealousy concerning my marriage and previous relationships I have had were really good and hers never seem to work out. When she accidentally found out about his position in our relationship there really wasn't much I could do because Denise can be a very vengeful person and wouldn't hesitate to reveal our secret to others.

She really enjoys humiliating and punishing him much more severely then I could ever do. I have seen her gag him and administer severe spankings and strapping's to his behind, Insert butt plugs and screw his butt with a strap on. She is another person when in his presence. I sometimes believe she has a deep seated hatred for men in a weird way due to her many failed relationships. When she visits several times a month as we live in the same town she really doesn't let up on him. She knows everything we do and takes full advantage of it. While I know if I am doing anything to my sissy no matter what I sense he also enjoys it. But with her I know he hates it and dreads when she comes by to visit.

As far as his punishments go I use a lot of normal everyday items such as paddles, spoons, straps and even large wooden paint stirrers. Sometimes he assumes a bent over position over a chair or sofa, face down on the bed or floor etc. CBT is done by hand, the strap or sometimes a wooden paint stirrer. His punishments are always moderate to severe in pain level depending on who is punishing him or the infraction that resulted in Annette being punished. I have also tied his penis and scrotum with rope. When I want to make it disappear I press his balls into his sack and press his tiny penis inward and then wrap an ACE bandage around his private area, through his crack and around his waist. When I slip a panty or a panty girdle over the bandage its hard to tell there was once a set of balls and a penis hanging there.

Sometimes he is restrained to the bed post or tied into a knee chest position for punishments or enemas. I often use his old weight lifting bench as a restraining board for him to be tied to. I can lay him on his back and tie his chest down to the board and then pull his legs up and tie them to the post by his head that would normally hold the weightlifting bar and weights. This exposes his ass, balls and penis and allows me unimpeded access to that area without him being able to move. I usually tie him with rope or old stockings. His balls hang very low and are easy to tie. They seem to have stretched out over the years.

As far as clothing goes I previously told you what Annette wears in the home and out in public under his clothes at work and when I want to humiliate him in public. As far as my sister and I go we only have our regular clothes such as jeans, sweatshirts, blouses skirts etc. Many times I punish him in my underwear. The normal type clothes for a woman my age. Often our play gets messy so I try to wear casual clothes or my underwear. Denise mostly wears jeans, stretch pants etc. I have a lot of fine clothes for work and pleasure but usually try to remove them when he is being used by me. I just never got into leather outfits or what I call get ups for our lifestyle.

Restraints for him include his chastity belt, Kali Teeth Bracelet, some leather cuffs and Velcro restraints and rope. We do have several enema bags up to 2 quarts, a double Bardex Nozzle, several douche nozzles and several butt plugs and inflatable butt plugs and dildoes to use on his girly vagina. I do have a penis gag and an inflatable ball gag that is interchangeable with the mask part of the gag. Many times he is gagged with a soiled panty and his jaw is wrapped closed with an ACE bandage to prevent him from pushing it out of his mouth. We buy his underwear in Target, Sears, and Kmart etc. His shopping trips usually are embarrassing for him.

I don't have a punishment room etc. He is disciplined in his bedroom, his bathroom or anywhere in the house. Many times it's in the basement. He isn't allowed in my bathroom or bedroom except when he is cleaning them. His mattress in his bedroom as you can imagine is quite soiled and there is a very distinct urine and sexual odor in that room. When company comes over I shut that door and make sure I spray outside his door to mask any telltale odor. Annette isn't diapered on a regular basis but at times he still has accidents. Sometimes when he is sleeping, being punished or just doesn't have my permission to go. He needs my permission to go to the bathroom under my supervision due to his masturbation habit. He is also not allowed any privacy at all when he is using his bathroom. This is for his own good and also to humiliate him. I generally don't allow him to use public bathrooms so if I know we will be out for an extended period of time I usually diaper him.

I have often over the years thought about taking him into a hair salon to have his hair and nails done, a pedicure or maybe even a body waxing but I just never came across a place that I thought would go along with it. Many times while getting my hair done etc I would in general ask if they get any male customers with strange request etc to sort of feel them out on the matter. But mostly got replies like a few come in for hair coloring maybe a nail polishing but that's it. So I really never pursued it. He was however fitted for a chastity belt in a store in Upper Montclair NJ called Dressing for Pleasure which catered to the D&S crowd. You should have seen his face as the store owner named Constance had him stand on a stool to be fitted for the belt in front of me and also a young girl on her sales staff. Several times she swatted his behind and told him to stand still.

When I took him to be fitted he had his male clothes on with a full length girdle on with breast forms inserted in the cups. It was quite amusing when he stripped down to his girdle and stood on the stool. Constance walked over to him and instructed him to spread his legs open and the she unsnapped the snap crotch and rolled the girdle bottom up to his waist. While she was measuring him she wore disposable gloves and warned him he would pay dearly if he dribbled or came while she was fitting him. When the belt came in several months later the procedure was repeated again to ensure a proper fit. In her many years of business she stated to me she has seen everything and was into the D&S scene over 40 years. She asked if I would like to attend some parties that cater to an S&M crowd and have them use my husband as a sissymaid to be used by other woman and also men. Helga I had to decline as we just weren't into this like that and wasn't comfortable around other strangers. She understood my concerns. Most of our toy's and equipment we bought in that store when we needed something. I have heard they moved to another location in the same town but under new ownership. We haven't been there in many years.

I truly believe my husband punishes himself for not being born a female. He has often told me how unhappy and uncomfortable he is living life as a male. He probably would have made a good candidate for a sex change when he was younger. But back then these things were practically unheard of and wasn't very common like it is today. I can't stress in all other ways he is a perfect husband and a good provider. He is very happy in his position in the relationship. I, over many years have come to the conclusion that what I do to him is out of my love and respect for him. I realize he needs to be treated this way and it fulfills his needs mentally and physically. As time went by I found it easier and easier to do what I do to him and after all these years it just comes to me naturally now. Having no children, and he having no close relatives everything I own has been left to my siblings.

The house has been left in our will to my sister Denise. If I should predecease my husband my sister will live in the house and my husband will then become her property and responsibility till he or she dies. He wouldn't be able to live this way on his own. We both realize this. He certainly isn't happy being left under my sister's control but I must ensure he is taken care of in his special way after my death. The three of us have had several discussions about this and we agreed to this with a verbal contract. My sister will abide by my wishes in exchange for my house. My financial assets are split between all my siblings evenly. After we all shook hands on it., our agreement was made. My sister looked at him and said "Hey sissy you better hope you or I die before my sister does because you will wish you were dead under my control. I looked at my poor husband and he actually had tears in his eyes and was actually shaking somewhat. I then kind of felt sorry for him and patted his head and said "Don't worry Annette it will all workout OK, you will get used to it if it comes to that"

I really sometimes feel unsure of how to explain this all to you after all these years of doing it and never sharing any of this with anyone but my sister. Now all your readers will know about my sissy Annette's life. But in a very strange way I am excited by it also. I can't promise you any pictures at this time since we are still discussing it. We are very private about this in a lot of ways. Who knows maybe someday you will see a picture attached of Sissy Annette.

Sincerely, Hugs & Kisses.

Thank you Jean for your very enlightening letter and for taking your time to compose it. I understand how relieving it can be to be frank in discussing your private life and I appreciate your willingness to let it all out. I am also delighted that our site proved illuminating.

I must say your sister seems quite formidable and I can see why your sissy lives in fear of her. I also hope that at some point we can see Annette in all her feminine glory.


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Letter 5