Protecting My Inheritance Ch. 04

"All we need to do now," continued Jill, "is to work out how we can help Santa to meet mum's request. I think mum has some ideas so I have invited her for tea this Saturday so we can plan the course of action."

There goes my Saturday football match.

Felicity came round on Saturday afternoon for tea. Over tea Jill told her that if we were to deliver her request in Santa's letter, we may need some help to get her present ready for Christmas.

"I may be able to help you there," said Felicity.

That's a surprise I thought sarcastically

"I have been going to a local shop, Betty's, for my underwear for a number of years. She used to work for my husband and we became friends then. When she set up her shop, I started to use it.

"I was talking to her two weeks ago when we had lunch. She has started a new service which caters more towards the male population who want to explore their feminine side."

"Sounds fun," said Jill.

"It may sound fun but its proving to be very profitable! Demand is surprisingly high. She runs two sessions, a fitting session on Thursday evening and a full make over session on a Sunday afternoon. I think we could take advantage of the services she offers and then Simon will be all set for Christmas!"

"Betty advised me," continued Felicity, "if I was thinking of using her service there is some preparatory work to be done before the fitting and gave me this list."

Felicity handed Jill a small sheet of paper. Jill glanced at it, and browsed its contents. She smiled and looked pleased.

"I think I could manage this," she said. "Yes, let's do it! There's nothing here that we cannot do. You arrange a date with Betty and I'll get Simon ready to go!"

When Felicity had left Jill came back into the room smiling.

"I'm so excited," she said, "I'm so looking forward to find a new you. I think I could be quite attracted to Simone.

Felicity booked the event for the following Thursday evening. That Thursday afternoon Jill came home from work early and took me into the bathroom. She helped me shave all over. I did my arms, legs and chest and Jill did the bits I couldn't reach. I then took a shower to get everything off and stood in the bathroom drying myself down. I dressed in my normal clothes.

Felicity came around just before five pm.

"We are due with Betty around six so I am in good time," said Felicity. "The shop will be closed to normal visitors so we have two hours of Betty to ourself to start on the transformation."

"Enjoy yourself," Jill shouted as she waved us off.

I didn't know quite what to expect. Felicity just smiled all the way on outward drive saying things like "you'll enjoy this" and it won't be so bad.

When we got to the shop we parked opposite and Felicity led the way. She rang the bell by the side of the shop door and a women in her 50s smartly dressed in a well-fitting navy blue, knee length dress let us in. She was wearing a string of pearls seemingly part of the uniform of an underwear fitter. Felicity introduced me to Betty.

"Nice to meet you Simon," said Betty as she turned and led us through the shop door. Felicity took Simon's hand as they both entered the shop behind Betty. Betty closed the door behind them.

"We like these evenings to be very discrete. There is no one in the shop other than we three and I don't want us to be disturbed."

Betty led the way to the back of the shop through a door into a quiet room behind the counter. There were two chairs and Betty indicated Felicity and I should sit down.

"Now can I understand what you are looking for?" said Betty.

"My daughter Jill," said Felicity, "has very kindly agreed that Simon, her husband, can be my Christmas present."

Betty smirked.

"No, not like that Betty! I wrote to Santa asking for a son-in-law doll that I could dress up as my daughter-in-law. I haven't got a real daughter in law and I thought it would be fun to pretend for Christmas."

"Ah, its clearer now," said Betty.

"Santa is going to grant my wish. Simon here is just waiting to see what he has to do to become my daughter-in-law."

Betty clearly had been here before.

"You have come to the right place. Many of our clients have husbands or boy-friends and want to see them dressed up. So you are not alone. Firstly we need to get Simon measured up. Have you any idea whether you want him to wear a skirt or a dress."

"Oh, a dress please and I have it here," said Felicity as she held up my punishment dress.

"Right, Simon, let me get you measured up." Betty seemed totally unfazed by having a man to measure up. Her tone and manner was very reassuring and surprisingly I found myself starting to relax.

"We will have to have his shirt off," Betty said to Felicity.

From the sound of her voice I realised the structure of the evening had been sent. I was here to be measured doll like. The client to whom Betty would make the sale was Felicity and from her initial remark she had made that very clear. I was to stand still and do as I was told.

Betty took off my shirt and measured my chest. The tape measure was cold to the touch and initially I flinched. She completed her measure.

"39 inches," she declared, "I think we might be best to try some examples and see what might be possible."

Betty went to the back of the room and came back with a few garments including a bright yellow bra which she held up to Felicity.

"This is a 40C," said Betty, "let's see how this fits."

She held the bra in front of me and indicated I should put my arms through the straps. She went behind me and fastened the back. I had never worn a bra before. This one felt surprisingly comfortable. I could feel it was there but it didn't pull or pinch. Betty got two pairs of tights and fed them into the cups to give me a bust. As Betty moved away Felicity was there with the dress putting it over my head and encouraging my arms through the sleeves. she helped me into it and turned me around so she could do up the zip.

"As I thought," said Felicity, "this dress is a size 18 and the C cups don't fill it."

"I have a 38DD we could try?" said Betty

"Let's have a go," said Felicity

The dress was removed, the yellow bra stripped off and a feminine engineering instrument placed on my chest. The bra was long line and elasticated with wired breast cups. When it was fitted it felt tight on my chest and I could feel the wire cutting into my skin. The bra cups required two sets of tights to fill and when the dress was put again, my bosom looked a mess. It was uneven, unbalanced and drooping.

Both Betty and Felicity took one look at it and agreed that a C cup was the only option.

"I think you will have to have the dress altered to fit Simon" said betty. "the dress needs to be pulled in a little at the bust so it fits a C cup. You also may want to look at the hips. I generally find men have slimmer hips so if you are not thinking of using buttock enhancers, you may want to make the hips fitting tighter too."

It all sounded very technical.

"Let's have a go at the bottom half!" said Betty.

Felicity removed the dress again.

"Take your trousers off," said Betty, "you can keep your boxers on."

As I took down my trousers Betty went back to her pile of garments and pulled out a white girdle. She held it up with her thumbs and sized it against me.

"Slide this on will you. It's a size 38 waist so should fit you easily."

She held it out in front of her.

"Put your foot into it," said Betty, "now the other one!"

I obliged. With both feet in the girdle Betty pulled it up around my waist. It was a tight fit but comfortable. Whilst it gave control over my shape, I didn't feel squeezed,

"This one fits him easily," said Betty. "It's the sort of girdle you can wear all day without any discomfort. Felicity, how do you want the dress to fit? It looks quite loose and flowing to me. If it was fitted more we would need to go down a size with the girdle so we had uniformity of shape. What do you think?"

"Can we try the smaller size on?" said Felicity.

"If we are going to squeeze him I prefer the girdles with the side zip and eyes. Allows us to get it on and them squeeze. I'll find one that is suitable."

Betty disappeared into her store room at the back and came out with a large girdle in black, Fastened it looked like a long tube with suspenders at one end. Betty undid the side panel and held it out for me to step into.

By this time I was having difficulty controlling my erection. It was challenging my boxers.

"A tight girdle sorts out this problem," said Betty as the took hold of my erection. "Maybe it's what he needs."

I put both feet in the girdle and Betty drew it up until the fastened circle sat just below my crotch She went to one side and stared to fasten the hooks and eyes. The first two were not too bad except my cock was now pressed firmly against the girdle fabric.

"Breathe in!" Betty commanded, "this is where the fun starts!"

I breathed in and Betty continued with the hooks and eyes. When she was halfway up she pulled the zip up to release the pressure on the hooks and eyes. As the zip was edged higher I found I couldn't breath out and I started taking in shallow breathes. Betty finished the top four hooks and eyes and pulled the zip up. I felt as though I were fastened into a tube of steel.

My shape was no longer my own. The girdle felt loose around my bottom but very tight against my stomach and the top line was against my rib cage. The only way I could breathe was not to move my rib cage which meant short shallow breathes.

"See this will give him some shape. But it is very uncomfortable. We don't recommend our girls wear this for more than a couple of hours. If you want him to wear that dress," said Betty pointedly looking at the blue serge dress, "I don't think you will get any value out of the tighter girdle. To see her new shape you would need a closer fitting dress of finer material. So I think we should stay with the looser white girdle."

I was relieved!

"I think I have what I need," said Betty as she helped me out of the girdle. "Let's go and put in the order. Simon you can get dressed!"

My fitting was over.

The next stage came the following Sunday. Felicity rang around ten am and said there had been a change of plan. Jade was already busy at Betty's with another client but would be able to drop over to our house this afternoon.

"It will be good if she does so," said Felicity to Jill, "with our event being on Boxing Day, the day after Christmas, Jade can't do the make up for us. So I suggested if she took us through what is required together we should be able to do it."

Jill agreed and so it was arranged.

Felicity arrived just before two pm. I was sat on a chair in the kitchen with a large mirror propped up on the worktop to one side. Jade arrived around two.

She started on my make up talking to Jill and Felicity as she did it.

"I can't join you on Boxing Day morning, said Jade. "I am sure you know what you are doing with make up but just a few tips on how a male face is different. The first step is to remove unwanted face hair so I'm going to clip the eyebrows. Then we need to get a smooth face. This isn't good enough. We need a face that is newly and closely shaved."

I was despatched to the bathroom to shave and returned to find them grouped together around a chair. I sat down on the chair.

She chatted to them as she set about my face. "Firstly get his cheeks and face very smooth particularly the top lip before you start. Then apply moisturiser liberally all over. More than you would ever use. A man's skin is usually dryer than a women's from years of neglect.

"Then use the foundation generously. Unlike your face there are whiskers trying to push through. You need to give them a barrier and a cover if this is going to last 3-4 hours.

"Generally over emphasise the make up. Too much will make him look like a drag queen so don't overdo it. He needs to be seen to be wearing the make up. You are creating features not emphasising them. Eyes should be lined in black all round. A man's eyes must be highlighted. I apply the mascara lightly and then put in a flash of white on the eyebrow. Its like a photo flash going off; it catches the eye.

"Use rouge to soften the cheek bones. Don't overdo it. The cheeks should be blushing. Use lip liner to paint a line on the lip outside the lip itself. A man's lips are not as pronounced and you need to make them look bigger. Use the lip liner to give the impression the lips extend into the face.

"Use a lipstick colour that is striking but not garish. This is a rich red. Hands and finger nails can be a problem. A man's hands are bigger and courser. If you paint the nails they highlight a feature that contrasts with the femininity you are trying to achieve. I recommend using fingerless gloves. White gloves can hide the size of the hand and by making them fingerless we can show off the fingers. I won't do the nails now but here is a jar of matching nail varnish to the lipstick. Betty will be able to fit you out with the fingerless gloves. It's a trick we have created together.

"I can lend you this wig. This is a short bob wig sitting just above the shoulders. The hair colour matches the colour of his eyebrows. Finally, I am adding a pair of clip on dangling ear rings to complete the picture."

"How's that?" said Jade as Jill held up the mirror. I knew I was underneath the picture somewhere but my face was very different. Perhaps it was the long hair surrounding my face and finishing just above my shoulders or the red lipstick. A female face was looking at me from the mirror.

The girls seemed pleased. I was ready to be Felicity's Christmas present!

The day after Christmas started very normally. Jill was busy in the kitchen making lunch and cooking the cakes for afternoon tea. I made myself scarce but was told to be available this afternoon.

I reported back to the kitchen at one pm. Jill took me upstairs into the bathroom ran me a bath and left me to shave my legs and arms. She came back 20 mins layer to check the outcome and shave those bits, like my back that I couldn't get to. She had taken to trimming my pubic area and in particular shaving my balls. Whilst I wasn't sure it was a good idea, I did enjoy her soft fingers soaping and shaving my balls. When she was finished I had quite a hard on.

"I think you need to get rid of this," she said as she ran her finger playfully along the shaft. "Can you do it yourself or do you need some help."

I looked her in the eye. "Remember rule three," I said, "no masturbation!"

She laughed. "Dry yourself and get into the bedroom."

As I sat on the bed she used her mouth and fingers expertly to make me hard. I was standing up and throbbing. Her mouth licked and sucked my cock head whilst one hand wanked my shaft and the other tickled and played with my smooth balls. She looked up into my face with her big blue eyes. The eyes looked at me appealing to let go and fill her mouth with my semen. Her tongue was licking my tip in a circular motion. The blood was running into my cock and it was so engorged I thought I was going to burst! I was desperate to come and took over the action. I put two hands on Jill's head holding it in position and then began to fuck her mouth. Her hand wanking my shaft fell to one side but she continued to tickle my balls

I grunted as I passed the point of no return. I paused as the semen rushed up my cock from my balls and ejected into Jill's mouth. Her head jerked backwards against my hand as the first rope of semen hit the back of her mouth and as ropes two and three followed the overflow from a very full mouth trickled down her chin. I released my hands and she let my semen covered cock fall from her mouth . She showed me my semen in her mouth, swirled it round her tongue and swallowed it in one gulp.

"Yum yum," she said, "be soft now but I want you hard tonight!"

I got dressed in a tee shirt and boxers. Felicity was joining us for lunch at two pm and Jill had promised to show her what I looked like when I had first worn the dress. I put on the white knee length socks and Jill put the dress over my head. She helped me into it and did up the zip at the back. The dress had been altered so fitted me better than the first time.

Jill took a photograph of me on her phone. I wasn't sure about this but Jill said it will set the benchmark for when Felicity later made me up.

"Mum has said you can borrow these for lunch," said Jill passing me a pair of white two inch heels.

Felicity arrived and we had lunch together. I was coached in wearing a dress and behaving daintily.

After lunch Felicity took me upstairs into her old bedroom. She helped me out of the dress and I took off the tee shirt. I sat down and Felicity helped me put on the tan coloured nylons. I stripped off the boxers. I saw her eyes view my cock as it slipped out of my boxers. Felicity helped me into the white girdle. It was longline so fitted me almost up to the rib cage. Felicity fastened the eight suspenders to the nylons and pulled up the girdle so that the nylons were held taut. During the time my cock had behaved itself and I made myself comfortable with the cock vertical and pressed against my tummy by the firm girdle.

Felicity held the bra in outstretched arms and I slipped my hands through the armholes. Felicity went round the back, pulled the bra up my arms and did it up at the back. I felt the bra bind to my hairless skin. Felicity delved into the bag and came up with two false breasts which she fitted into the bra covers. Finally I put on the white silky slip.

Felicity called Jill up to join us

Jill joined us put a towel around my neck and around my shoulders. She started on the make up. With moisturiser foundation and lots of lip stick and mascara she was at it for nearly an hour. When the wig and earrings were fixed I was ready.

"I have this perfume for you to complete the occasion," said Jill and she showed me how to spray it behind my ears and on my neck.

"Yes, you smell delicious," said Jill not letting Simone know that this was the perfume used by Karen.

Felicity helped me into the dress. She had bought a belt which she fastened round my waist and I slipped into the white shoes. I was ready. Jill snapped the photograph for posterity.

"I just need to pop home for something," said Felicity with a wink at Jill. "I'll be back at four."

"We will be ready," said Jill.

The door bell rang at four. Jill sent me to open the door. I was wearing the dress. I opened the door to see two people standing there. When I saw two people outside I was worried that my secret was going to be shared more widely. It took a few seconds to realise one of them was Betty.

"I hope you don't mind, said Felicity, "but I have invited my friend Betty for tea."

When I had got over my initial shock, I realised Betty had seen me like this before so I wasn't being "outed". I breathed a sigh of relief and led them into the lounge. I admit I felt a little flustered; the shock of seeing two people on the doorstep was taking some time to subside. Jill was waiting in the lounge. After the greeting and peeking on the cheeks I was sent into the kitchen to make the tea.

I could hear the three girls talking. I call them girls because they were chattering and giggling like three young girls. They were clearly enjoying the event. I slowly got the tea ready. My thoughts were mixed. Doing this will get rid of the punishment dress. But there was a nagging doubt that if they were enjoying it so much, they would want to do it again. I didn't want dressing up to become the norm. One special occasion, fine but not ever again. I took my time as I decided how I was going to play this.

I went back into the lounge with the four tea cups. The three girls went quiet as I entered the room. I knew they had been talking about me. I felt their eyes on me more so when I turned my back on them to return to the kitchen. I picked up the tray carrying the tea and cakes and returned to the lounge.