Tomorrow Was My 25th Birthday

This story is a tale of a young boy and his development into a sissy by his Aunt and family, includes incest and some BDSM. If you are offended by tales of BDSM and sex between consenting adults then read no further... otherwise enjoy.

Please leave honest comments or suggestions, it really does encourage those of us who write to continue...

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Tomorrow was my 25th Birthday, it was also to be my wedding day to my Aunt!!

Perhaps I should explain how I got to this point.

My father died when I was young, just 12 years old, and I grew up in a household of women, my Mother Emma, who was 34, and my three sisters Jane 16, Sally 15 and Jessica 13.

Because of the balance between male and female I guess it was always going to be that my formative years and through puberty I would find myself taking the female view in most things.

Added to that was the fact that my Mother together with my Aunt Alice, 12 years her junior, opened a lingerie store after my father's death to help supplement his pensions and allow us to stay in the family home.

So it was that I helped out at the shop on weekends, and as puberty came I got used to handling ladies underwear have a penchant for silky and lacy things.

As I grew up there were many times when Mother said to me during shopping trip "I wish you had been born a girl." Probably because I could of, like the girls, had hand me downs instead of new, we were not poor but had little spare money and I was made to feel a burden on the family funds.

I attended school and left when I was 16, moving n to University. While there I indulged in some crossdressing, who wouldn't with a Mother who owned a Lingerie Shop, and three elder sisters whose clothes I could steal. Once I had finished Uni, aged 20 I returned to work full time in the shop, mainly with my Aunt as Mother had so much to do at home, four children and being a single parent would be a strain on anybody's time.

It was shortly after I returned home that I awoke having had a dream. While I lay trying to get back to sleep, I heard strange little cries coming from Jane's room.

Thinking she was having a dream like me, I tiptoed across the hall to her door which was open about six inches, and peeked in.

What I saw remains with me to this day. Jane, 24 now and very thin and willowy, was tied spread eagled to her bed, her wrists and ankles tied to the four bed posts. Sally, 23 and quite muscled as she played a lot of sport, was naked and sitting astride Jane's face, grinding her pussy into her face, and my Mother was lying between Jane's legs I assumed licking her pussy and that's what was causing the little whimpers of pleasure from Jane.

At nearly 21, I knew about the birds and the bees but was not so conversant with lesbian sex, or incest, those were both alien to me and something I had never considered. Wasn't it wrong. Incest I mean.

I had a very sleepless night worrying about what I had seen and feeling all protective to Jessica, was she involved as well or was she at 21 too young.

I guess when I think back it both excited me and troubled me at the same time but as a youngster these things never seem to last or worry you for very long.

Once I was working in the shop with my Aunt full time she seemed to take me under her wing and I found I could ask her anything without her seeming to judge or be surprised by what I asked, she just put it down to an enquiring mind.

My Aunt was only 10 years my senior and we got on so well, I think she enjoyed my company and I was always a willing worker, happy to sort and put out new stock of frillies as it came in, what boy wouldn't love touching girl's underwear all day.

It was during the quieter spells that we talked about all things, and during one of these chats I raised the question of lesbians without mentioning what I had seen that night at home.

Aunt Alice explained to me that not all women, or men for that matter, liked the opposite sex. She admitted that she was bi sexual and that she enjoyed the company of both men and women, that the sex between her and a partner could be as good regardless of their actual sex. She also admitted to having a love of cross dressers and transgendered people, mainly male to female.

Never having come across either of those I questioned her more and she explained that some men like wearing women's underwear and sometimes dressed fully and this she found exciting sexually, they were usually known as cross dressers as they had no desire to be a woman all the time.

Then she admitted she had had a liaison with a guy that was taking hormones and while still a man, dressed more often as a woman and wanted to become one in time, living their lives as a woman all the time. We discussed in depth what the hormones did to him and what was involved in the transformation to being a woman, I have to admit this got me very excited and I am sure I was blushing a lot.

I eventually admitted to her that I had sometimes taken underwear from my sisters rooms or out of their washing to wear and that it excited me and I wanked in them.

She smiled and said not that I was 21 I should perhaps have some items from the shop to keep as mine, and she would take the cost out of my wages.

I was nervous about this but she promised not to tell a soul about it, not even my Mother or Sisters, it was to be our little secret. That night I went home with two sets of bra and knickers, and a suspender belt and stockings.

I should say that even when 21 I was naturally very slim, and at 5 foot 7 inches not a tall man, and I had grown my hair long and wore it in a pony tail, it fell to just below my shoulders but was fine tied up.

Over the following months I took the odd thing home from the shop to add to my collection but I never had a lot of money as my sister and I were all still living at home and I had to pay rent to help with the bills.

My mother was always worried about my size, saying I needed to fill out a bit that I had a girly figure, I guess that was her way of enforcing what she had said about wishing me to be a girl, and when she decided I need to take supplements that she said were vitamins I did not object and just took them each day when she gave them to me.

For my 18th birthday we had a small party at home, my Sisters, Aunt and Mother were all there together with my best friend Matthew from school, he was the total opposite to me, big and beefy, played rugby and was built like a brick shithouse, we looked like the odd couple standing side by side.

We opened some presents then, my Aunt saying she had left hers in the shop so I would have to collect it tomorrow when I got in. Being my 21st Mother opened some bubbly and we celebrated with some drinks, and it did not take me long to get drunk.

I had forgotten that I was wearing a pair of frilly knickers which I often did during the day, enjoying the feeling of the satin and frilly lace around the legs.

As the evening went on I got drunker and as my speech started to slur Mother said "I think we need to get you to bed."

Matthew said with a wide grin "Don't worry Emma I will carry him up and tuck him in."

He then picked me up like I was a rag doll and took me to my room where he undressed me.

"Well what have we got here," he laughed as he took my trousers down revealing my girly knickers, "Bit of a sissy boi are we."

I didn't respond, I was really out of it, and didn't realise what he meant. I vaguely remember him taking a couple of pictures of me lying on the bed before he pulled the covers over me, and kissed me hard, pushing his tongue into my mouth.

As he broke off he said "See you soon sweetie."

The following morning my Mother awoke me, I was feeling really bad, my first hangover was not good, "Come on, up you get," she said as she pulled back my bedclothes.

"Oh!" she exclaimed when she saw my panties, then laughed at me. "We need to have a talk sissy boi."

I got up, and got ready for work before sheepishly going downstairs. My Mother and Sisters were all in the dining room chatting and laughing, and that stopped as I walked in, then they giggled and stated sniggering to themselves, obviously Mother had said what she had seen.

I blushed bright red and hurried out without breakfast to the shop.

As I got to the shop I was first there and I went in the back office and just sat, wondering what I had done, and now they had found out what was I going to do, I wished Auntie would arrive I had so much to talk to her about.

To be continued...