My Sissy Son

My Sissy Son

I came across your site just recently. The site is so well done and so informative. I am divorced female, now 45, and my sissy son has just turned 22. I try to keep in shape, I am 5’11” 135 38C-24-36. My son is 6’1″ and so very handsome. I never thought I would be writing something like this, but would appreciate your input. I have so many questions and you seem to have so many answers.

My first reaction was that I never thought it was so common and it seems so widespread. My story begins about a year ago. I had dressed very sexy and was going to an all day party with girlfriends. When I got there, the hostess had taken ill and we all decided to reschedule. What happened next was something out of the twilight zone. When I arrived home I walked upstairs to my bedroom and heard moaning. I watched from the door.

There was my son, Mr. Macho, dressed in my things, tall heels and all, playing with himself in front of my full length mirror. My mind went blank as I tried to process the scene. He was wearing a bra, panties a girdle, my white satin garterbelt, stockings, a half slip and a full slip and my 5″ white pumps with gold heels. He had taken the time to put on makeup, earrings and a necklace and even an anklet. I am Bi and I was looking forward to partying with my girlfriends – we have fun! I am not sure how long I stayed at the door and watched, probably a lot longer than I remember now.

When I finally found the courage to walk in, my son was speechless. That was a first. Then I got “Oh mom I am so sorry”. I sat on my bed, trying to be calm and cool and told him to walk and model for me. He had one of my wigs on and really looked quite sexy. He was way past embarrassed, more like a deer in the headlights. After the ice was broken I started to enjoy his situation. For once mom was in control.

I told him to stand there and not move and went to get my digital camera. I had him pose and lift his slip(s). He begged me not to take pictures but I told him that these would be much better than baby pictures later. Then I told him to go and stand in front of my full length mirror and show me what he was doing before i walked in on him. He was so shy. I walked up behind him and cupped his little breasts and fondled him and told him to show me. Finally I let my hands wander down his slip and began to caress him. He came almost immediately. I coould feel hium pumping into my panties and tight girdle and remember calling him a bitch as he shot load after load into my clothes.

After he calmed down he wanted to just undress but I said no. I told him that if he wanted to feel like a woman he sould experience what is like to stay in wet cum soaked panties. We sat on my bed and talked. He confessed to so much and was really honest with me. That impressed me. He had been sneaking around for years watching me dressing and undressing and then going to jerk off. I told him that if he was man enough to ask – he could watch but he had to ask and be buck ass naked when he came to my door.

I was shocked at how long he had been dressing in secret, always in my things. I asked him if he had spied on my that morning and he admitted he had. I described everything I was wearing underneath my clothes. He was hard again very quickly with all the conversation but still confined in my panties and girdle and all his wet cum.

I told him I had noticed him trying to look up my skirt when we were on the coouch watching TV. He admitted he had. I told him to lay on the floor and I stood over him, my legs apart and asked him if that was what he wanted to see?

I made him put on jeans and a sweat shirt and told him we were going shopping. No sock, just his loafers. He was terrified. In the car we talked about what we would buy and that I didn’t want him wearing my things anymore. I am not sure which of us was more embarrassed but I made him pick out the styles he wanted. I told most of the clerks what had happened and they really were great. First Penny’s then Sears. We had the basic black and white, then pink, pastels and red. All with garterbelts, panties, bras, slips, some girdles, Skirts and Blouses, some dresses and his little black dress, three pairs of tall heels, white, black and red, and a few wigs of his own. After awhile we were like to little girls on their first shopping spree.

I have two guest bedrooms, one with a walkin closet. We spent hours cutting tags and hanging and folding his new clothes. When we got home I told him to loose the jeans and sweat top. That is when I noticed he had painted his toes. I told him to hold up my slips and I unzipped my girdle and slid it down his legs. It was soaked as were my panties. I hadn’t seen his cock for years but he is HUGE, long and very thick. It was funny at first to see it so hard and framed in my garterbelt. Not very ladylike but still erotic. I told him that he was going to wash all my clothes later and then fold them and put them back where he had found them. He was way past horny and his cock looked so sexy poking out under my slips.

I told him to decide what he wanted to wear for dinner and suggested that we should both take a shower and dress as if we were going out. I told him that if he jerked off I would spank him until he couldn’t sit. I said that he he wanted to be dressed as a woman he would act like one, not like a whore.

I decided to wear my little black dress with a black garterbelt and long sheer stockings a my 5″ black pumps. Amazingly, without see me , he did the same but he wore his new black lace bra and black lace panties. nails and makeup. We had steak and lobster and champagne. For the first time we were talking, sharing and he confessed to so much more

This all happened on a Thursday. That weekend I was due to go out of town and took him with me. I had been to a salon in Ft. Lauderdale a few times before. I called ahead and asked my girl at the salon if she would wax both me and my son. She owns the salon and said no problem. That Saturday was quite a day. I stood in and watched as he lost all his body hair. In spite of his pain, his cock was so hard and twitching. It didn’t bother her and we laughed that such pain could get such a response. He looks so good smooth.

When she finished waxing him she winked at me and ent down on his magnificent cock. I wasn’t mentally prepared for that. It didn’t take long and my son was shooting rope after rope of sperm into her mouth. When he finished she bend over him and kissed him and gave him everything she had saved in her mouth. That was one of the most expensive waxings with the tip and all. What I found so fascinating is that he took it all and swallowed. He left to get his nails done and I was next. She did the same to me after I was waxed clean, but just the two of us. I climaxed over and over again as she stayed with me. I am sure my eyes were so glazed over as I went out to have my nails done.

She had referred me to a place in Ft. Lauderdale that specialized in crossdressing. We found silicone breast form – he is now a D cum. As they say “Oh what a difference”! They had bras in black and white where the breast forms slip inside. It is wild, they come with realistic nipples and look so sexy under a dress or blouse.

Anyway, that is our story. I am so glad that I did not freak out. It has been a wonderful journey. You site really helped me to understand that this is not a one off. I can only imagine how strong the urge to “dress” is. I would really like to know is there are other mothers who have dealt with this, or other sons who wished their mothers had? He is a very sexy woman now, no one knows and we have fun! Please get back to me as time and schedules permit.


[Donna – I love this picture into your life, and my houseboys will love it too. Thank you very very, A.]