Tomorrow Was My 25th Birthday

This is the continuing 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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My Aunt arrived and straight away she said "What has happened sweetie, you look so scared and sad, bit hung over are we."

"I don't remember much about last night, not sure how I got to bed but Mother woke me this morning and found me wearing those nice white frilly knickers, the ones I had last week, and now she has told my Sisters and they are all sniggering and laughing at me." I blurted out.

"Oh dear, Matthew put you to bed darling, he was so kind."

I started to cry, "Then he has seen my knickers too, he must have undressed me"

My Aunt came over to me and gave me a big hug, I snuggled into her, she felt like my saviour, and looking back I guess I had a bit of a crush on her.

"Darling I have watched you over the past few years, how you have developed, how you have grown up, your desire to wear knickers all the time and I dare say bras as well when you have had the opportunity, and now you are 21 perhaps we should chat about what you want from life moving forward."

I looked at her. "What do you mean Auntie?"

"Do you remember when we chatted about lesbians and cross dressers and transgendered."

"Yes Auntie."

"Well in my opinion I believe that you should think about living as a woman, you know the 'vitamin' tablets you have been taking the last couple of years for your Mother, they are actually hormones, female hormones."

I looked at her stunned, "Why would she do that Auntie."

"Well she always wanted a forth little girl, and you are so slim and not really a man, more of a little sissy."

"Now take your clothes off I have your present for you."

I got undressed trying to take in what she had just said to me, Mother had been in on this all the time and I never guessed.

"Now stand in front of the mirror."

I stood there looking at myself.

"Have you not felt your little breasts being tender and sensitive and growing a bit, I am sure you have at least A cups now, your hips look softer and more female, you bottom is more of a bubble butt now."

I looked at myself and had never noticed the changes to my body, but she was right and my nipples had been so sensitive recently I had stopped wearing bras.

"Now open that box, it is your birthday present." She pointed to a beautifully wrapped box on the side.

I took the box and opened it.

"This is your first full girls outfit, I want you put it all on see how it feels."

I looked in the box and slowly took things out, studying them and putting them on the side. There was a satin aa cup bra with matching knickers, a suspender belt also to match and taupe seamed stockings, a cream satin blouse buttoned down the front with frills, a mini skirt which looked very short, and some black paten high heels with an ankle strap, the heels looked to be at least four inches. There was also a short bobbed wig, and a make up kit.

The door bell on the shop went and my Aunt got up and said "Put everything on expect the wig and the make up, I will show you how to do that later," and walked out to see the customer.

I had mixed emotions, did I want this, my Aunt seemed to want me to, and what would my family say if I started dressing as a girl. I thought my Mother would probably like it but I knew how cruel my sisters could be.

I sat on the stool and looked at what Auntie had got me, I picked up the panties, feeling the soft satin feel that I enjoyed close to my body and slipped them on. I then followed with the bra, lifting what little titties I had and making sure they filled the cups, just.

I then picked up a stocking, slid my hand and arm down them like I had seen my Mother do, put one over my toes and pulled them up my leg, luckily I had never been very hairy, possibly because of the hormones but I didn't think about that, I just luxuriated in the soft silken feel of sliding them up my legs.

I also noticed that my cock was trying to get out of my panties.

I put the second stocking on the fitted the suspender belt around my tiny waist, passing the actual suspenders under my knickers and attaching them to the stockings.

I then stood up, admiring my new lingerie in the mirror and rubbed my legs feeling the silkiness of my stocking rubbing together as I took a couple of steps.

I then put on the blouse, loving the satin as it caressed my skin and did it up, then undid the top button so as to show what little cleavage I had.

I then stepped into the mini skirt, it was PVC and had a zip on the front that fastened from the top down to the hem. It was tight but I got the zip done up, it was as I suspected very short, only just covering my stocking tops, I would have to be very careful when bending over not to show my knickers.

I looked in the mirror again and really enjoyed what I saw except for the bulge in the front of my skirt, and when I turned to the side my little bubble butt filled the skirt nicely at the back.

Just then I heard the bell go and my Auntie reappeared from the shop.

"Well well, what do we have here, a most presentable young lady." She smiled at me and kissed me on the cheek.

"Now let us see what we can do about your hair, and if we cant that's what the wig is for."

She turned me around and undid the band on my ponytail, letting it loose, "My you have a good amount of hair here." She said as she started to brush it, "I think this will do admirably."

She brushed it and set it with some product she had, finally spraying some hair spray on it.

She then ordered me to sit and went to work on my face. Again I was lucky that I only had to shave perhaps twice a week I had so little facial hair and I had shaved that morning trying to wake myself up with my hangover.

She worked on me, applying foundation them some blusher then told me to shut my eyes but not too tight and she applied what I assumed was eye liner and eye shadow. Finally she was done and told me to purse my lips, to which she applied a lip liner then a nice deep shade of red lipstick.

She stood back and looked at me. "There I think that's you done, not bad if I say so myself."

She spun the stool round and faced me towards the mirror. I gasped, surely that was not me looking back from the mirror. I certainly looked like a girl.

I saw my Auntie smiling over my shoulder, "See you can be a girl if you want."

She knelt down and said "Now stand up and put these on."

I stood and she helped me put the heels on, doing the ankle straps up for me. Then she let me steady myself on her shoulder as I took my first tentative steps in them.

The bell went again and she said "You stay here darling and we will continue our conversation when the customers have gone."

It was a couple of hours before the shop had emptied and she returned to the backroom. In that time I was getting used to the heels, just walking around the stockroom enjoying the feelings of the satin and stockings and the skirt on my legs, my only disappointment was this thing that kept making a tent in my skirt.

"So how do you feel." She said looking me over, and spotting my bulge. "I can see your excited by being a woman."

I blushed bright red, almost the colour of my lipstick.

She went to the fridge and got some ice out then went down on her knees in front of me, lifted my skirt, pulled my knickers aside and held my cock in her hand full of ice. I soon shriveled despite being held so intimately by my Aunt.

Once I had shrivelled she took me and tucked me down between my legs, then pulled my knickers up hard to keep me there. "That should do it for now, until we find another solution."

With that she smoothed my skirt down and looked me in the eye and said "I think its decision time don't you?"

"But Auntie what will Mother and my Sisters say?"

"Well you need to know more about your family, things have changed a lot while you have been away. In the absence of a patriarch I have taken the role of head of the family, and quite often I stay over at the house."

"Your sisters and your Mother all submit to me and do as I tell them to so if you decide you want to take the path of becoming a woman to the outside world they will be happy for you, because I will be happy about that."

"However you should know that if you chose that path it will not be all excitement and frilly clothes, there will be thing that you will have to do to please us all and contribute to the family, but we can cross those bridges as we come to them."

She pulled a couple of sheets from her desk, "You will need to sign this as you are now of age, it gives me certain rights over you, but you need not concern yourself about that, all will become clear in time."

"Now you need to decide if you wish to go ahead and become a male to female transgender or remain as a cross dresser, the choice is yours, all you need to do is sign on the second page."

I looked at her and she smiled at me, "You have till the end of the day." Just then the bell went in the shop and she said "Well go serve you're not here to just prance around." She slapped my butt encouraging me to go into the shop.

I tottered into the shop and started serving, my mind a total whir, as I thought about what my Auntie had said about the family and if I wanted to remain like this, dressed as a woman.

To be continued...