Helping Jess Pt. 04

I got into the house. Jess looked into my eyes and saw I was out of it. "I guess that was quite hard for you John, maybe too much too quickly."

I nodded. My head was screwed, I didn't really know where I was. She gave me a kiss on the lips.

"OK sleepy head. Let's get to bed. Up the stairs with you, and brush your teeth!"

She watched me walk up, then cat-whistled me. "That's a nice piece of ass there. I bet you go like a bunny don't you luv?"

I got embarrassed at that, how could I react? She saw my confusion and laughed. I wandered into the bathroom and brushed my teeth.

Shortly she came up – back in her red silk chemise and red silk panties. As before they hugged her body tight, showing off her great figure and making her as gorgeous as ever. I groaned when I saw her. All I wanted to do was to hold her and make love to her, not as if I had any chance of that.

"You OK John?" she seemed really concerned using my real name.

"Please Jess, you looking fucking gorgeous, really something else, but I think you know this, please can I just hold you and stroke you?"

"Oh John, you are sweet, but now I want you to stand in front of the sink and look at yourself in the mirror. For now I am just going to look at this piece of meat and feel your pretty silky butt that I have been missing."

Her hands started feeling me and stroking me, the feeling of being stroked through the satin was great. I started to touch her hands and arms and stroke her back.

"Keep your hands off me you dirty pervert. Keep brushing your teeth. You are my little sex object to use as I want. Stand there nice and passive like a good girl and make me happy."

Her hands were going all over the place, and sometimes reaching between my legs. I was getting so horny again, but unable to do anything. Eventually she stopped. "Now keep your legs straight, touch your toes and close your eyes." I did as I was told, obviously it made my butt easy for her to touch. I closed my eyes.

She started stroking me again and lifting up my nightdress to look at my arse.

"Oh you are a pretty bitch Belle. In the future I am going to give you a good pegging in this hole. The idea makes me hot. I also want you to be as pretty a sissy as possible OK? You have to learn to apply make-up, and then we'll buy you pretty jewelry and anything else you can think of – nice frilly clothes, and you'll have to talk like a girl, and sign like a girl.

Tomorrow I want you to make a list of what things you can do to be more girly for me. I will be your man, your job is to make me want you. List 10 things that I would find attractive as a horny man, and I will choose what you have to do. These things could be beauty items like putting a ribbon on the top of your stockings or on Daphne. The other side is actions – maybe you do a dance for me, or you give me a lecture on how best to put on a suspender belt.

Now open your eyes, and let's go to bed. You need to give me multiple orgasms before we go to sleep. You won't get any of course – hehe. You can go to sleep in my arms so close but so far."

We got into bed and she demanded I please her passionately, kissing her all over, using my fingers to please her, and then my tongue – at which point she grabbed my hair and pulled my head into her pussy. Eventually after her third orgasm, we finished.

"Thanks Belle, that was nice. Now put your arms up to the headrest." I did so and she cuffed me, both arms. After that she chained my ankles. "That's better don't you think?"

I smiled, "well, this is like heaven for me mistress, I love being under your control. Though it is a tough heaven, being denied all the time, and you being next to me."

"Well it is my heaven too Belle, having a pretty sissy service me. Now I want to have a look at Daphne, she can spend the night out."

She was lying next to me, she pulled the covers off me and took a key off the bedside table, and lifted up my nightdress. I heard the lock unclick, and soon she was taking off the cage. Daphne sprang to attention.

"Oh she is sweet jumping up like that, she's a very good girl isn't she Belle?"

She took a cloth and cleaned Daphne, then without any warning she put Daphne into her mouth. She started giving me a blow job – 3 strokes, 4 strokes, 5 strokes I was in heaven and so close to cumming."

I started thrusting and then she stopped, lifted her head away from Daphne and made sure I had no friction anywhere to finish it off. I writhed in my chains, so desperate, but I couldn't do anything.

"I'm sorry Belle, but that makes me happy to think of you all horny and desperate while we go to sleep. And in future, don't thrust, I will punish you for that in the future, most un-ladylike."

She put my panties back and pulled the night dress down – it tented to her amusement, and pulled the cover over us.

"Now stop moving and trying to get the friction you need to finish yourself off. You are not getting off."

I was close to crying, but I made sure I didn't. She snuggled up close to me, and kept stroking me for a while. Whenever Daphne started getting soft, she would give a small stroke to make her hard again and then giggle.

Eventually she turned over and soon I could hear a regular and rhythmic breathing as she fell asleep. I was tired myself and before long fell asleep.

I woke up around 6am, she was lying next to me watching me. "Hello my pretty sex toy." She threw the covers off.

"I want to keep looking at my pretty little slut." She started stroking me. Pheobe started rising.

"Oh hello Pheobe – nice of you to join us!

I was a bit tough on you last night Belle, so I am going to be nice to you. I will let you cum, though I was tempted to keep you horny and Pheobe free when you go shopping – no doubt you would get many erections in the lingerie stores when you see the pretty lingerie and the assistants notice that kind of thing." She kept talking and starting stroking Phoebe. I was getting very horny again. She was deliberately drawing it out. I wasn't sure whether to believe she was really going to let me cum or if it was going to be another cruel joke. She was also using a pair of satin panties to stroke Phoebe, she knew that the feeling added to my excitement.

She kept going and I was getting closer and closer now, "Do you want to touch me Belle?"

"Yes please mistress, can I touch and kiss you?"

"Yes, though I will leave one leg chained, and not completely free. I want you to get used to the fact that every time you cum from now on, I control things, and you will be tied and get your pleasure on my terms, or not at all."

She proceeded to uncuff both hands and one leg, but left the other leg chained. She continued stroking me and ordered me to touch her. "Behave like a fucking man for god's sake, if you want to touch me, then touch me – everywhere. Kiss my nipples and try and make me wet. Stop being an indecisive sissy."

I was all over her then, I ripped off her top, and I couldn't get enough of her gorgeous breasts and body and kissed her neck all over, and started getting her wet as well. She kept stroking Phoebe and eventually I couldn't hold on.

"I'm cumming, aaghh yes."

She pushed me back onto the bed and kept stroking until I was finished, then she stopped, and just held me.

"That was great thanks."

She unlocked my ankle chains and left the room. I surprised myself by going back to sleep.

Some time later, I was woken up by Jess with a cup of tea. "Wake up sleepy head – you have had another 2 hours sleep, but now we have some shopping to do."

I sat up and took my tea. She was dressed in a t-shirt and a tight pair of jeans. I realized I was still dressed in the night dress, and felt embarrassed. I tried to cover myself with the duvet.

She found this amusing, and stopped me. "You must never hide your beauty from me my pretty. You are my little toy to do with as I please. Think of yourself as an object which has to be shown to me and to be pretty for me."

"But please Jess I look ridiculous."

"Look Belle, I find it cute that you are sharing your perverse dreams with me and trust me. Remember that I get off on your embarrassment, and that with this I can control you more and more. We both know that you're not a girl, but you like dressing in girls' clothes, and I intend to push you further than you have gone so far.

I'll tell you now, that I want to show you off to some of my girlfriends, and I want it that they don't realize you are a man at first. I am sure they will find it hilarious when they see how far I push you. Don't worry they aren't from around here."

I was shocked but excited at this, I think it showed. She pushed my chin up and closed my mouth. "Don't worry you will get used to being exposed. It will often be very embarrassing for you.

Now, I have put out the clothes you will wear this morning, and we need to go out and do the shopping. I want to buy you lots and lots of pretty things. Plenty of lingerie as you can't wear male underclothes any more, and we need to consider other things too like dresses."

This scared me. "Jess, can we not go local – I really don't want to go anywhere close. Also, please can we make sure nothing is public."

She nodded and we agreed to go to a town a one-hour drive away. She agreed that no outer female clothing would be obviously associated with me.

"Jess, this friend of yours, is she coming tomorrow and what is her name."

She went quiet at this, "Yes, I had forgotten about that. Her name is Claire. Please do me a favour John – I'll use you real name around her – but please talk very little around her. She'll be difficult for you to handle otherwise."

I didn't get it.

"Why, does she do?"

"Nothing, she is very nice, but she is an alpha female, with a capital A, and she is always right. She can misunderstand things sometimes and she has a big temper. Given she will have your key, I suggest you be nice to her."

"She's going to take the key? I have never met her before, does she have to take it? Can't we use plastic locks or you keep the key?"

"Yes she is taking it – it was part of the conditions, and she is bringing her own lock. I have told her we are together and she won't let me keep the key or let you have any way out. It's ok though – as long as you don't annoy her, you'll be fine. Now let's get moving, we have some shopping to do."

She clearly didn't want to talk about it anymore. I was a bit nervous about this 'Claire' who I had never met before holding my key for 2 weeks, what if she had an accident or something? I followed Jess down the stairs.

In the living room, there was laid out for me some cream silk stockings, a cream satin basque with 4 straps to the suspenders, then some white French knickers. Phoebe started to get hard seeing these clothes. Jess noticed this.

"Good, I am glad you like them, now put them on carefully. Remember any damage and you will be punished."

I was careful and managed to put it all on without any damage.

She had also brought a pair of my jeans and a blue t-shirt. I put them on, then realized I had no socks.

"Jess, please can I have some socks?"

"No, and start getting used to not having socks, it will be hard at first, but you'll manage. Now in one of the shops a friend of mine works and is expecting to meet my pretty sissy. When you meet her, ask her to help select the prettiest, girliest, sissiest lingerie for you."

This scared me, and pushed me into my sub space.

She let me take a pastry for breakfast and soon we were off. She drove. It took a bit over an hour, and when we arrived, Jess pulled me into several lingerie shops.

She delighted in holding bras, panties and chemises and nightdresses up to me, and asking me if I thought I could wear a thong. I died of embarrassment and fear, hoping no-one would see us. I asked her not to do it, and she told me to stop complaining or she would ask an assistant for advice.

She was enjoying my embarrassment, and strung it out with lots of comments like "I don't know John, this colour doesn't suit your complexion," and "John, this one will go so well with the pink corset and dress I am going to buy you."

Of course, we didn't buy everything at once, she was drawing it out, some panties here, stockings there, nightdress elsewhere. Everything was satin or silk with touches of lace.

"It's a pity we can't get inner silk linings too Belle, that would rub against you all day and you'd be a horny mess."

We went into one shop, and a sales assistant came up and asked if we would need any help. Then she recognized Jess, "hi Jess, how are you doing?"

"Hi Sue, good thank, it has been a long time, I hope things are going well for you."

It was clear they knew each other well. Sue looked at me.

"So you are Jess's latest. This is a bit different for her. I hope you know what you are getting into. I understand you like dressing up in woman's clothes?"

Jess continued, "Yes, this is John, he is a closet sissy. His little fetish is now known to me, and he is not allowed to wear male underwear any more, but pretty lingerie. Please call her Belle"

She then lifted up my jeans to show my cream stockings. Sue laughed at that. I went crimson.

"He is also wearing a basque and French knickers, would you like to see them?"

How could she? I was beetroot red with embarrassment.

"Yes, that would be amusing, but would you like me to Belle?"

I had only just met Sue, and now I was going to have to ask her to see me in lingerie. Jess had a stern look on her face, one look at her made it clear that I had to do exactly that.

"Yes, please could I show you the lingerie I am wearing?"

Sue responded, "That's nice. It is quiet now, but it's probably best if we don't use the changing rooms – other customers might not appreciate it. So let's use the office, but before we do, are you looking to buy anything Jess? If yes, I suggest when you are finished we go to the office for John's display."

"Oh yes, we want to buy several things Sue. Now Belle, did you have something to ask Sue?"

I remembered Jess's words from earlier, I was supposed to ask Sue for help. "Sue, please could you help select clothes for me. I like satin and silk, maybe with a little lace. It should be pretty and sexy, and girly."

Sue smiled at that and agreed to help. The 2 girls held lingerie up against me and argued about whether it would look good on me, whether it would suit my other clothes – that we were going to buy later. They had fun discussing whether thongs would look good on me – and they agreed that I must get silky frilly clothes, and sissy lighter colours, nothing dark.

When finished, Sue took a nightdress, suspender belt and stockings and took the labels off. She gave these to me, and then took the clothes.

"I'll take these clothes into the office. Take the labels with your other clothes and pay for them at the cashier."

Fortunately the shop was quiet and there was no-one else at the till. The cashier was a young petite cute girl with black hair in a pony tail, and she was wearing black silk blouse. She had very clean and tidy make-up and a lovely smile. Normally I might have tried to talk to girls like this, but in my current predicament, I just wanted to get out.

The cashier started scanning the clothes, and then did a double take when looking at me, then at Jess and then back at me. I think she was suspicious with the sizes.

"Have you got the correct sizes sir?"

"Yes thank you," I said, just wanting her to hurry up.

She was taking more time though. Jess was beginning to smile. I saw from her name badge that her name was Samantha.

"Pretty clothes, I am sure the lady will love these". She was going slower and slower. She got to the labels. "These are nice, are you paying for these too?"

"Yes, I am," a short sharp answer from me now, I just wanted to get out as quickly as possible.

"Where are they then?"

"They are being worn out, so we just show the labels here," at this point Jess snorted, she was loving this. I could see Samantha smiling too, this was turning into an embarrassing nightmare. Samantha turned to Jess, "Are these for you madam? You don't look like a size 14."

"No, I am a size 8," responded Jess.

"Ah then who is wearing these clothes then?" asked Samantha with a smile.

"This sissy is, she loves dressing up in female clothes, don't you Belle?"

"Yes mistress," was all I could say. After all that had happened recently, I didn't think I could get more embarrassed, but I was wrong. Now Jess was clearly enjoying exposing my sissy side to this cute girl who was over 10 years younger than me.

Samantha no longer was talking to me, but to Jess, "I have heard about such sissies and we have suspected about some of the men coming in, but this is the first time I have known. Could I see her dressed up some time?"

"Most definitely, Belle would love to show off her outfits for you, wouldn't you Belle?"

I could only nod.

Jess leant over and whispered into my ear, "ask her to go into the office now and see you dressed up. If you fail to get her in, I will punish you hard later – even if it isn't your fault. Beg her if you have to."

I looked at Samantha and gulped. "If you have time, please could you come into the office, I am going to show myself in some of these clothes to Sue and mistress."

Samantha smiled but then looked around. "I'd like to, but I am not supposed to leave the till."

I remembered Jess's threat. "Please come." I said. I couldn't believe I was almost begging this girl to come to my humiliation.

"OK, give me a second." Samantha ran across the store and spoke to an elderly lady hanging up some clothes. I guess to ask her to cover for her.

We made our way to the office. Sue was initially surprised to see Samantha, then Jess explained I had asked her to come as well. Sue found this amusing.

I proceeded to put on the clothes Sue had selected for me. I had to walk up and down and model them. I had to walk this way and that, and they commented on my poor walk and how they could improve me. Jess told me to keep smiling, and to spank my butt suggestively for the girls.

The girls found this hilarious. Of course Phoebe was getting hard. Jess joyfully explained that the humiliation was turning me on, they laughed at that too.

Eventually we finished, Sue turned to Samantha, "Sam, didn't you say a friend of yours worked at a beauty parlour? Do you think she would like a challenge?"

"Yes, she does, you mean to work on Belle? We have talked about this before theoreticlly and she loved the idea."

Jess jumped on this, "really? That would be excellent, Belle needs quite a lot of work, and I wasn't sure how to do this properly. So far I have thought of perming and dyeing her hair, applying false nails – the toe nails would be permanent, waxing and other hair removal. There is probably more – maybe with eyebrows and eyelashes."

I was shocked at this, and I think it showed. The girls all loved this.

"She can do all of those, and I think she has a room at the back for privacy as well. Give me your number and I'll talk to her and call you in a few days and we can arrange a time."

"Brilliant. That's great isn't it Belle? Give us a few weeks and you'll be a stunner – maybe we can then enter you into a sissy beauty competition, you'd love that wouldn't you?"

I was terrified at the thought, but nodded, and Sue and Samantha looked delighted and asked to be kept involved.

Jess and I left, she took us for lunch at a local restaurant. She gave me a bag with some clothes in it.

"OK John, in a second go and change into these clothes. Until tomorrow afternoon when Claire comes, you are to wear male clothes everywhere and be a man. I want to be your girl and we'll be a typical couple together."

I took the bag and changed into my boxer shorts and a pair of socks and took off all the lingerie. I gave it back to her.