Mom's Grateful Sissy.

Mom wanted a daughter and she got me instead.

I saw little of my Dad who was in the military. I met him when I was five years old and then again at seven. Then when I was ten he came home "to stay" which ended up being a very traumatic three months. The entire time he berated me referring to me as a "filthy little sissy faggot" constantly threatening to cut off my waist length curly blond hair and make me into a man, with beatings of course. He was worse to my Mom which I now realize was why they didn't see much of each other. Mom kicked him out and the divorce was final by the time I finished fifth grade.

Then things went back to what passed for normal between Mom and me. She was always affectionate with me, almost hyper affectionate and I have to admit I was spoiled. I saw my classmates deprived of all the wonderful things I got to have and do and I knew I was spoiled so I tried to be the nicest person I could be to Mom and also not demand too much. She could afford pretty much anything I asked for but I tried not to ask for the ridiculous. I wanted a fancy sports car but didn't want to push my luck so I asked for a nice bicycle. Mom shelled out $1500 for one. I wanted a 20 foot TV for video games but I asked for and got a 72 inch one and the game console and games I wanted. I wanted a $700 pair of Nikes but asked for and got a $150 pair.

Mom wanted a daughter and asked for one when she got pregnant with me but she got me. So since she has always been generous with me I never complained whenever she wanted to dress me up like a girl. It didn't happen much at first. Halloween of course and then three or four times a year she and I would drive to another part of the state where she would take me to a salon for a mother/daughter make-over and she would buy me clothes and we'd stay overnight in a motel and she would just have me spend a couple of days as her daughter pigtails, pink nails and all.

But once her divorce was finalized it became more frequent. Three or four times a year turned into three or four times a month, almost every weekend. Then came my 12th birthday. The weekend before I turned 12 she sat down with me and made me an offer I could not refuse. She offered to give me absolutely anything at all any time I wanted and I could do anything I wanted if only I would let her transform me into the daughter she always wanted, permanently. I would have to agree to go along with her informing my middle school that I'm transgender. I'd have to come out to my friends as transgender.

This might seem like an awful lot to ask of a typical 12 year old boy. Except I wasn't typical. I don't know if she ever knew but I always enjoyed being feminized by Mom. While I never thought of myself as an actual girl, I certainly enjoyed the idea of living as a sissy. It might seem like splitting hairs but I was fond of my genitals the way they were, especially since discovering masturbation shortly before turning 12. So I agreed as long as I got some input on fashion and I could veto any style that I felt went too far.

What Mom didn't know was that of my three only friends in the world, one boy and two girls, the boy had come out to me the year before as gay and confessed to having a crush on me which while I didn't immediately reciprocate I was very flattered and we remained close friends. And my two female friends had already told me they assumed I was trans by my appearance and mannerisms. One of them had already told me she thought I was cute as a girl and even expressed an interest in casually experimenting sexually with me. The other one just wanted to remain friends but hadn't completely excluded the possibility of one day being more.

So when I officially came out to my friend's as trans they just shrugged their shoulders as though I had just announced that water is wet and the sky is blue.

So Mom threw me a big birthday party, my three friends and several relatives who I also came out to. My one uncle, wasn't too happy but everyone else was very nice about it. That morning before the party she took me to a salon to get a really glitzy make-over. I looked ready for a pageant. My gay friend slipped me some tongue the moment he saw me. I was wearing a pink chiffon dress and patent leather pumps.

I think my Mom's Dad really wanted a granddaughter too because he was nicer to me at the party then ever before and he had always been rather nice as it was.

So from then on, throughout school I was Tiffany. I used the girl's rest room and took gym class with the girls (did I mention I'm actually bi so yes that was hot!).

Mom got my room made over and all very girly pink and from my 12th birthday onwards I never work any male clothing at all. The only non girly thing I did in high school was baseball. I wasn't allowed on the girl's softball team and I was a pretty fair hitter and outfielder for a sissy. Did I throw like a girl? Yes, most definitely. I three like a champion softball pitcher. I had the second best record for outs (ironic). I also bat 269 which was the second best on the team. At first the league said I couldn't play because I was a girl but then my coach told them that I was actually transgender and still had my boy parts so they made an exception for me. I was the only "girl" allowed in the boy's locker room though they put a curtain up in the corner where my locker was and I was offered the coach's private shower. I secretly wanted to strut in pink lace lingerie and be grabbed and held down and gang banged by the whole team. I settled for a threesome with my friend and another player who had come out as bi. We got together after games for celebratory sex. I'd suck them both at the same time while they made out or they'd both fuck my ass while we triple kissed.

2 months ago

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