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Helping Jess Pt. 01

By: mski



Jess and I were co-workers. I always thought she was pretty hot, and I thought a few times that she made quite a lot of eye contact with me. She had a great body with long blond hair – that she normally kept in a pony tail and no fat that I could see. She had a mischievous smile, as well as a naughty sense of humour. I thought about making a move on her occasionally, but I was a bit nervous about how it would work out with us working together. I also suspected she was a class above me, and would probably say no. So I kept my distance and tried looking for love elsewhere.

We were put into the same project team, and got to know each other quite well. It was a stressful project, tensions sometimes ran high. Once or twice I felt that Jess made some mistakes, but I defended her. I think she did the same for me, she was complimentary about my skills. There were 6 in the teams, and it meant working some late nights. Often the team would go out to the pub afterwards and we got to know each other really well and liked each others' company. Sometimes the group were invited to each others house for parties. 

We talked some times – and got to know each other quite well, we had some common interests with triathlon and sports. She used to play handball quite seriously, I just liked to work out myself, and occasionally swim, cycle and run. We also said we should race each other. Against most girls I would feel confident of winning, not with Jess.

As long as I managed to forget how attractive I found her, I could talk to her quite well. We found ourselves talking about anything and sharing the problems we had. Eventually the project ended, and we saw a bit less of each other. One day she called me up and asked if we could meet up, to go for lunch, she needed to talk to me about something private. I didn't think anything of it, we had met up for lunch many times, though not just the two of us.

We met up and were in the pub, ordered our food and when it came we took our food and drinks to an alcove with round tables. We soon got talking like old times, however I felt she seemed a bit nervous. After a while I asked her what she had wanted to meet me about. She went quiet, after a while she spoke 'John, this is really awkward and I am really embarrassed to be getting into this conversation.' 

She paused before continuing on, 'can you keep a secret? Let me ask you something, and you can say no, but please don't tell anyone I asked you this.'

I was intrigued now, I had never seen her act this way. 'Jess, no worries, you can rely on me, I promise I will not tell anyone.'

She seemed a bit reassured, and reached out and held my hand. This physical contact was a surprise to me, we hadn't touched before, and it reminded me how beautiful she was.

'Thanks John, I knew I could rely on you. This still may be a bit of a shock to you.'

She took a drink and then started again.

'Let me say it slowly. I have a really close friend who I have promised to look after and to help her wherever I can. I feel I owe her as I have let her down in the past. She has now got a very promising academic career.'

She stopped and took her hand away and took another drink. She then took my hand again and she moved closer to me. I began to notice how beautiful she was and she was wearing a short skirt which showed off her legs that looked perfect in their nylons. 

She looked me in the eyes, 'Thanks John, I am still really embarrassed about this, and I hope you don't get upset about me asking this and you can say no, and I hope you don't hold it against me.'

'Jess, come on, you know we are good friends, I would do anything for you.'

She looked at me in a funny way.

'Thanks for being nice to me John. Well my friend works in an advanced psychology area, normally cognitive, but she also works on how sexual instincts can conflict with cognitive functions. She normally works on animals, but now is moving into a new area, and is doing some basic studies on humans. Oh I am so embarrassed I am talking to you about this.'

I tried to reassure her, looked her in the eye, 'Look Jess, just say it, I promise not to tell anyone, and I promise I'll help however I can.'

She smiled at me and grabbed my hand with both her hands and moved to sit right next to me rubbing her body against mine. After a while, her hand rested on my knee. I was not sure if she was doing it deliberately, but I was having trouble thinking straight, and I certainly wasn't going to stop her.

'You are so nice John, thanks for helping making this easier, it will still be a shock I fear. Anyway, my friend is doing some studies, normally these studies are done on university undergraduates, and she has got some, but she needs more and she cannot find any more. She asked me to help. 'She is looking at the effects on people when they are unable to have sexual pleasure for a period of time.'

'OK, it's a bit unusual, but that doesn't sound too hard. You mean not to have an orgasm for some time?'

She squeezed my hand again.

'Yes, it is to go without an orgasm for 2 weeks and to keep a diary of how it feels, how it affects emotional state, decisions, physical well-being etc. twice a week there would be a detailed interview where she can ask questions. Honesty would be needed, but there is total confidentiality.'

'And you are wondering whether I could help in this?'

She looked at me with pleading eyes, 'well yes if you could it would really mean a lot to me.'

She rubbed my arm and smiled shyly at me. I noticed that her hair was loose, no pony tail and it just added to her attractiveness. I wondered to myself how I had never tried to ask her out. I was being the typical male and wanting to please this gorgeous girl, no matter the consequences.

'Well, it's not as if I have a girlfriend or anything, so yes I think I can help.'

'Oh thank you John, you have made me so happy.' She gave me a hug.

'Though, there is something I should say before we finalize this. This will be a bit embarrassing, so please don't say anything for a while. We know that the average male masturbates once a day, and even if they promise they won't, they will probably masturbate. So there is a requirement to wear a chastity belt. This would be checked by my friend or a male assistant. Is that ok with you?'

Now this was a bit of a shock, I did masturbate every day, and having that taken away would be a bit of a shock. However doing something for Jess would be great, and she was looking sexier and sexier, the longer she held my hand. I have always had some submissive thoughts, but resigned myself to not finding a suitable girl. Regardless, full chastity might be a shock.

This whole situation was really very unusual, but I thought maybe I could use it to my advantage.

'OK, I'll do it Jess, but I'd now like to ask you one thing in return. Now this might seem a bit cheeky, and you can say no if you like, though I hope you don't. And please don't tell anyone I asked you.'

'Thank you John, thank you, thank you. Please ask me.'

'OK, I'll wear the chastity belt and go through the experiment, but at the end can I take you out for dinner?'

She looked at me and beamed at me. 'Yes, I'd love to John, I thought you'd never ask.' She gave me a big kiss me on the lips.

'I'd love to go for dinner with you, and if we weren't in a pub where our colleagues might see us, I'd give you a proper deep kiss now.'

Superb! I thought, and it probably showed with my smile.

'My friend is under a bit of time pressure, and you know I travel late tomorrow night and am only back Friday night. Would you have time tonight to come over. I have been told that it is best to try it for a day first to practice, before trying it for a longer period of time. I can let you out tomorrow evening before I go, and then you have a little break. Then on the weekend we put it on for 2 weeks? Would that be ok?'

'Yes, that is fine. How should we do it – where should I go?'

'Well I suggest you come over to mine, my friend has given me the chastity belt already, and we can try it on.' 

'Another thing John, do you think we could do the date tonight? I don't want to waste time, and I would like to get you into my claws as soon as possible. In fact I like the idea of you taking me out for dinner when you are locked up – I know my honour won't be compromised!' she smiled at this.

'OK Jess, then I'll see you this evening. Is 7pm ok?'

'Yes, 7pm is good – come to mine then. Can you book the restaurant for 8pm. Let's go 50:50 on the bill – you have no choice here, and please make it a very expensive restaurant, I want to see you looking your best in a suit, and I will wear one of my best dresses.'

We agreed and then chatted for a bit longer, moving on to work. 

That afternoon was very hard to concentrate. I was thinking about the evening, and what I had got myself into. However the thought of going on a date with Jess made me determined to handle what was coming.

I left as soon as I could after 5pm, and drove home quickly. I ironed a good shirt, pulled out my best suit and shaved. I applied some after shave, and tried to look my best.

I thought about the situation I was getting into, a beautiful girl about to put me into chastity. This could be something I would regret, but I knew if I didn't take the chance to get to know Jess better, I would probably regret that more.

I arranged the restaurant reservation – the best one I knew. The car was a real mess, not the best way to impress a girl, so I tidied what I could, and realized I had to leave so as not to be late.

I got there a few minutes early and rang the doorbell. Jess opened the door and invited me in. She was in a dressing gown with wet hair, I guess she had just got out of the shower. She led me into the living room.

'Would you like a drink of anything?'

I asked for a water. She went and brought it back.

'I suggest we put the belt on now and get that out of the way.'

I agreed.

'OK, so please take off your trousers and underpants.'

I did so feeling quite self conscious, we weren't in a relationship yet, and here I was taking off my clothes. To my embarrassment, I was getting aroused and my penis started rising.

'Oh, someone seems happy to see me.'

I was quite embarrassed, I didn't say anything. 

She took the belt and tried to fit the cage on to my penis. I realized it was a curve – I had used one before.

'I'm afraid you need to wait Jess, it won't go on while I am getting hard.'

'OK, how can we get it softer?'

'It takes time. It is hard because you are attractive. You probably need to leave the room. If you like I can put the cage on while you are out.'

'No I like the idea of doing it myself. Then stay here, I'll leave and do what you have to do to get softer.'

She left me standing there. With time I relaxed and my penis softened.

She came back in after about 15 minutes, She was still wearing the dressing gown, but her hair was drier. I hoped that she would wear something more attractive for dinner.

She managed to get the cage on. I had to help talk her through different stages, though when I moved my hands to do some parts she slapped them away. 'No, I want to do this myself, I like the idea that later I can think that I locked you away, and you had no choice.'

Of course that affected me, and my penis tried to grow, but couldn't.

'Oh, I see you like that idea. Being locked up by a girl. You seem quite unable to control your penis John, it's a good thing I am locking it up.'

Eventually she got it all ready, she lined up the lock and told me to look her in the eyes. I did so and she stared back at me and talked.

'Thanks John, I have to say I really like the idea of locking you up, and now I am going to close this lock. You are mine now.'

The lock clicked shut. Probably it was a small sound, but it sounded huge to me. The tested the key, the lock opened and then she shut it again.

Then she stood up and shook her hair. 

'Would you mind if I kiss you now?'

'No, I'd love it.'

She moved close and gave me a deep kiss. It was wonderful, her hands were going everywhere, and she slipped them down my trousers and cupped my balls.

'Are you comfortable dear?' she asked me teasingly.

'Well I love kissing you, but it is a bit frustrating.'

'I have to say John, I love this power, it really turns me on. You now depend on me for any sexual satisfaction. I hope that doesn't make me cruel and that you don't mind.'

'No Jess, actually I quite like it.'

'OK, good, then let me take off this dressing gown, and we can continue.. By the way you have to stroke me all over.'

She shrugged off her dressing gown and I saw she was wearing a blue silk basque with stockings. She was stunning. I couldn't keep my hands off her. Though at the same time it was incredibly frustrating with the chastity belt.

After a while, she pulled back.

'I need to get ready and do my makeup. Let me take these keys with me.' And she left. I turned on the tv.

After about a half hour, she came downstairs, she was wearing a petite black dress, that really showed off her figure, her blond hair loose over her shoulders. She had put some make-up and looked even more stunning.

'What colour lipstick would you like me to wear dear?' she asked, she showed me a red and a pink. I chose the red.

'I thought you'd choose that. Imagine what my red lips would look like around your cock!'

I was a bit shocked at that, she was very forward.

'Oh I forgot, that won't happen, with you all locked up.' She giggled at that.

'Or maybe I should give you a blow job in your chastity belt, I wonder what noises you would make. I hope you don't mind me fucking with your mind,' she said taking hold of my arm.

'No, its fine, it just grabs me inside. I like it.'

She quickly applied her lipstick, and then we were off.

Helping Jess Pt. 02



The First Date


It was a bit strange driving with the chastity belt on. I had worn one before for some days, but a long time ago. We got talking about different stuff. It just clicked – as long as I forgot about the belt, or how good she looked.

She asked me to go via the office, she said she had forgotten something. I did so, she came back soon after with a smile on her face. I asked her what is was, she said it was something the security guard had said.

We got to the restaurant and I parked, before we got out she asked me if I was comfortable, I said I was. She leaned over and kissed me, and put her hand down my trousers, stroking the cage.

"This may be a bit nasty of me, but I love the idea of you all locked up. I am a bit wet. Now walk behind me when you can and look at my body, you can hold and stroke it this evening if you are a good boy."

She walked ahead and I couldn't help but stare at her gorgeous figure, her slim physique and gorgeous legs. 

We went into the restaurant and were soon seated in a quiet alcove with privacy.

We starting talking about some work stuff, and then some sports stuff. We had agreed to leave the car there and I would pick it up the next day. We split a bottle of wine and were having a great time.

"So do you like what you see John, am I attractive for you?"

"Yes, Jess you have a great figure."

"What do you like the most in women's figures – breasts, legs, stomach?"

I was embarrassed and started giving some general answer.

"It's not that simple Jess, it is more the overall look and the personality."

"Oh for Christ's sake John, be a fucking man and say what you think and don't think you'll offend me, otherwise I'll throw away the key to your fucking cage."

I was quite shocked at that, Jess had got a bit angry with this. I quickly recovered.

"OK, stomach – I love it when women have a nice flat stomach, particularly lower stomach, and that they are so flat where men have their balls and dick. They look stunning in their dresses then. I also like nice slim legs. I also love it when women have nice nails, when they have spent time on them."

"That's better, not a pansy answer like before. That wasn't so hard was it dear?", it wasn't really a question and she went on, "What about clothing, what do you like? What makes your head turn, and makes you hard?"

"Well, shiny and tight things generally, satin, leather, pvc, latex, clothes that are tight and show off the girl's figure. There may be some lace in there. Also straps, the clothes seem so flimsy at times, little straps over the should just holding the clothes in place, oh and I love the straps from suspender belts. I also am not hugely into nudity, rather the clothes help decorate the feminine figure."

"OK, interesting, and let me guess you love suspender belts and corsets and nylons as well?"

I nodded, "the more straps on the suspender belt the better and particularly with good quality satin stockings - shiny is the key thing."

"Ok, that's good to know. Sorry about snapping at you a minute ago, I hope you don't mind."

"No, no problem at all, it's ok."

"OK, now I'd like to ask, what about personality – do you like to be in charge and your girlfriend will do everything you tell her – cook, clean, give you a blow job when you want. Do you like to make the decisions?

Or do you like it pretty equal all the time, you work things out between you?

Wait before you answer, a few more options yet – do you like to mix it up, sometimes she decides, sometimes you decide?

Or last option, do you like her to be in charge, do you find it easier if she makes the decisions and you follow what she wants. Does it even please you to have the decisions taken away from you, and you don't have to think? You just please her."

Oh wow, she was getting pretty serious with these questions, I was clearly in the last category – I am submissive if anything, and love going into sub space, but here I was on a dream date, I was afraid I would say the wrong thing.

"I haven't thought about it, I prefer it to be pretty equal I think."

She looked a bit unhappy with that. I wasn't sure what the issue was, and a silence come over us. From then conversation was difficult, we finished what was left of our food.

"Can you arrange a taxi? You can stay at mine that is probably best, I have a spare room. I can drop you off at your car in the morning."

I wasn't sure what to think at that, I had hoped we could spend the night together, even if I was in the chastity belt. However she had suddenly got all distant. I went and arranged for a taxi and went back to the table. She was still quiet.

"Are you OK?" I asked.

"I am not sure," she said, "I feel you are unable to be honest with me. I don't want to talk about it now. We can talk a bit more when we get home."

This made me nervous, was I going to lose my chance to continue with Jess before I even started? We didn't talk to each other on the way back and I got more and more nervous.

She paid the taxi, I held the door open to let her out, she smiled at that at least. 

We got inside and she quickly took me upstairs showed me the spare room, and showed me the living room. She got me a drink and told me to wait a little. 

I sat down and waited, feeling a bit nervous. 

She came back in quietly in a big towel dressing gown.

"Look Jess, I really hope I haven't said anything to upset you. I would really like to make this work between us. You are a really special person, stunning and clever, a dream."

She smiled at that. "That's nice of you John. I just want you to be honest with yourself and me, and not be scared if things go outside your comfort zone, OK?"

I nodded, and was about to say more, but she put a finger on my lips.

"Shhh John, let me lead the conversation. One question to you – you have worn a chastity belt before haven't you?"

That scared me – that is going straight to some of my submissive tendencies. 

"Yes, I have thought about chastity belts before and wanted to try it out."

"Interesting, and have you let someone else hold the key?"

I had been to dominas before, but I was scared to mention this to Jess in too much detail, what would she think of me.

"I have always liked the idea, and did once ask someone."

"Oh excellent, please tell me more." She seemed really pleased at this.

"Jess, this is a bit embarrassing to talk about, and here we are on our first date, I really don't want to ruin any chance we have."

"John, remember I have locked you up in chastity, so it's not exactly a normal first date. Look you can trust me. I have been curious about trying things like this out for a while, and I'd love to hear more. In fact if you don't tell me, that will ruin your chances with me."

At this point she came over to me

"Can I sit on your knee?" she asked. I nodded and she took off her dressing gown to reveal her gorgeous body in a red silk chemise and red silk French panties. She then straddled me, and faced me and gave me a kiss.

I tried to stroke her, but she pushed my arms back.

"Don't touch me, you can just watch for now, and you have to earn the right to stroke me. But before you tell me more, let me be honest and lead. I think you are submissive and like to be controlled. I would love to have a relationship with you where I control things between us. I would love to be your real-life fantasy. Let's put it another way, you're a cute guy and everything, but if we are going to have a vanilla relationship, I am not sure. I would need to think about that, I'd like something different now where I lead things.

Now hopefully that is direct enough for you to be honest. I feel a bit scared now what you will say, and that I have exposed myself as some pervert.

So, can we revisit the question I asked you in the restaurant, has someone locked you in chastity and what happened?"

"Jess, you are an amazing person, and I would love to be in a relationship with you. I hope you are a pervert, because I am too.

So, yes, I asked a mistress to hold my key for me. I paid money for it. I guess you want to know all the embarassing details now."

Jess gave me the biggest smile she had ever given me.

"Oh yes, after what I said you owe me the embarrassing details, and you have earned the right to stroke me know. In fact I command you to stroke me, and you have to keep stroking me all the time."

I jumped at that chance, she felt like perfection!

"Keep talking dear," she said to me.

"Er, ok, well I went a few times to this mistress. She locked me into the chastity belt and I went away, and she held the key. It is actually very hard. The longest I went was a week and that was really hard."

"Good, so you like being denied?"

"Well, it is hard, I guess I like the suspense and not having control, and the orgasms when they come at the end are a lot stronger. It is also a bit painful at times when I get horny and in the middle of the night."

"OK, what else did you do with this mistress?"

"Oh Jess, do I have to, this next part is going to be really embarrassing."

"Yes, you have to tell me all the embarrassing details – I had to give that speech earlier and expose myself as a dominating pervert. But before you do, take off all your clothes. I am dressed as your fantasy and I feel exposed, we need to correct that – I wear the clothes, and you wear nothing. Actually, just stand up and I will take off your clothes, you cannot do anything."

Her smile was back. And she slowly started peeling off my clothes. First the shoes and socks, then my trousers, then my shirt. Lastly she pulled down my trousers, and had a good look at my penis in my chastity belt. She stroked the cage and made cooing sounds about how cute it looked. Of course I was trying to get hard.

"Is he getting hard?"

"Yes, and he has often been this evening and it doesn't take much when you look so gorgeous."

"Oh you naughty boy, trying to flatter me."

"It's not flattery, its true, it hurts."

"OK, OK, now sit on the floor by the sofa, you can give my feet a massage while you tell me what else you got up to. Did she make you do anything?"

"Er yes, well the big thing is that she made me dress up as a maid, or into all sorts of girls' clothes. She told me if I wasn't girly enough, then she wouldn't let me out of chastity. I was desperate to get out. I would do anything. I had told her of my forced feminization weakness, and she deliberately played on that. the trouble for me is that being forced to wear the clothes made me hornier.

Oh Jess, I don't believe I said all that all that. Please don't think me a weirdo, please don't tell anyone."

She stood up and pulled me up and gave me a deep kiss.

"Don't be silly, I am so happy you opened up and started telling me this. I promise I will use it against you and control you, and hopefully make you happy on the way. Now I'd like to sleep with you, I feel safe knowing you are in your chastity belt, and can't overpower and rape me. I think I also have something I'd like you to wear."

She led me upstairs, into her bedroom. She pulled open some drawers and eventually found what she was looking for.

"I knew I had it. An ex and stupid boyfriend bought this for me and got my size wrong – too big. This is a nice long sexy satin nightdress. It might be a bit tight on you, but that is good – you won't be able to forget your predicament. I also want to tie you up for the night, so you feel completely helpless next to me, so go and have a pee, then we can sort you out."

It a long red satin night dress. It looked really nice, but no doubt would look stupid on me. I went and had a pee, a little nervous about what might happen. I came back and she helped pull the nightdress onto me.

"OK, John, your first rule, these feminine clothes are delicate. If anything gets damaged, I will punish you severely, treat them with respect. It may mean you have to change your behavior and move much more carefully in them.

"Yes Mistress."

"Mistress, I like that. I think we are going to have fun together. Now lie on the bed."

I lay on the bed. She had some handcuffs on chains around the bedposts, which she proceeded to put on me.

"Good, so John, now we understand each other. I am very happy you are here, tied up, in a pretty nightdress, in chastity and telling me all your perverted secrets. I promise to make this great for both of us OK. Now I want to hear it all, what else did you do with this mistress?"

"Ah ok, thanks Jess, well a lot actually but feminization and chastity were the main 2 – they are headfucks – she made me beg to be feminized, and also I often had to suck her dildos and dance for her. If I didn't do it well enough, she didn't let me out. She once had a friend round and she made me explain to her friend that I loved to dress up as a sissy. She made me beg her friend to wear a strap-on that I could suck. Mistress observed my technique and gave me a report afterwards and a mark out of 10. I was caned very hard for every mark under 10, and the following week I had to repeat it, and then they both caned me for each mark under 10.

It was very embarrassing. Jess, this must seem really weird, do you really want to hear all this – also it must be ugly seeing a guy dressing up as a girl."

"John, I have heard of this before – men getting dressed up in women's clothes, and you're right I can't say I am very attracted to men in girl's clothes it does look a bit ridiculous. However I love this idea of control and pushing a guy to do things that are embarrassing or humiliating. We now both know you like it and I want to use it for the power. Am I right in saying that once you are dressed as a maid, the control gets extreme – he will be afraid of getting found out and do anything. So if I asked you to lick me to orgasm, or clean my house or serve me and my girlfriends, or cook for me, you will do anything I ask?"

"Oh blimey Jess yes I guess you can ask me almost anything, but I would be worried about others knowing about it, I really don't want it getting back to work or my family or friends. Also, one thing I am not gay, sometimes that gets misunderstood."

"OK, that's understandable. Now shut up, and keep still, I am going to get my vibrator and have a massive orgasm, while you will just lie there in your pretty nightdress and watch frustrated."

I kept my mouth shut, and saw her sexy body jump across the room, open a cupboard and pull out her vibrator. Soon she was back in bed gyrating, leaning on me, and screaming as she had a big orgasm."

Eventually she relaxed and lay on top of me. 

"Please Jess, this is hard, can't we take this belt off and I can make love to you properly?"

"Oh you poor little sissy bitch John. It must be so hard seeing me enjoy myself like this, and please know that my orgasm was even stronger for knowing that you won't get off tonight. I am tempted to let you out John, but I knew this would happen. I left the key in the office deliberately to stop temptation."

"Are you serious? Oh you cruel bitch, I can't take this."

"John, you are stupid, I am your mistress, you can't address me like that."

"I'm sorry, but I am so horny, and you are gorgeous."

"Haha yes, get used to it, I'd love to do this a lot to you and you know you won't want to walk away. But you know what, you can tell your drinking buddies that we fuck like bunnies. Just you and I will know the truth – hehe. Now, I will punish you for calling me a cruel bitch, but that can wait till the morning.

We should get some sleep, we'll be tired tomorrow. But before we do, here is a little present for you."

She put her hands onto her wet pussy and got some of her juice and smeared it into my nostrils. She also gently stroked my balls.

"Hehe now you can think of me at night, sweet dreams."

She held on to me and before long was asleep. It wasn't so easy for me. Eventually I dozed off.



Helping Jess Pt. 03



Sometime in the morning I woke up with Jess on top of me giving me a good morning kiss. 

'Wakey wakey sleepy head!' she said with a huge smile.

I grinned back, it was a nice way to be woken and she looked as gorgeous as ever in her red silk chemise. I started to get aroused but my penis was always going to lose the fight against the chastity belt. I grimaced.

'Oh, I'm so sorry, I hope I am not causing you too much discomfort,' she said with a big smile clearly delighted to be doing exactly that. Her hand slid down my body to stroke my balls.

'I'd like to spend longer to get you nice and horny and have you lick me out, but we are short of time, so let's just get up, have breakfast and go. One thing, keep your night dress on. I'll say when it can come off, and I will control what you wear from now on.'

'Yes Jess,' I said, this could be very different from my normal lazy mornings.

'No-one we know will hear about this will they? You won't tell anyone will you?'

'Relax John; your secret is safe with me. Well maybe I will tell some girlfriends, but certainly no-one you know, and no-one from around here.'

I was a bit nervous about this, but I didn't feel I could argue much, being in chastity and a nightdress. I recognized that sub space feeling coming to me, where it is simpler not to think and just go with it, fortunately with a beautiful girl leading the way. Once she uncuffed me, I grabbed her and pulled her to me, and gave her a deep kiss on the mouth.

'You naughty girl John, but I like it,' and she returned the kiss passionately. 

We had breakfast, she gave me some muesli and milk, and sat on my knee, her slim body next to mine. She forbade me to feed myself 'no you are my helpless little sissy princess'. It was great, though I was reminded of my chastity belt all the time. No doubt this was why she did it. 

When finished, she told me to stay where I was, and she went upstairs. She came back down with my clothes, though there was a difference - no underwear, or rather no male underwear. 

'So sissy John, your fantasies start here. From now on you are to wear female lingerie at all times including at work, and I will pull you into the bathroom occasionally for a quick snog and a quick feel. I will check and feel all your lingerie, just like a teenage boy. In fact I might annoy you by pulling at your bra straps, no doubt you did that to the girls when you were young.'

I started to deny this, but she put her finger to my lips and told me to be quiet.

She held out a white bra for me, a pair of cotton panties, and a white suspender belt and black silk stockings.

'Now take off your nightie and step into your bra. I hope they are not too small, well, they probably are, but that's all we can manage at this time. Be very careful not to damage anything like a clumsy man or I will cane you.'

I managed to put most on, she helped with the bra, and I got the panties on. I put on the suspender belt and the first stocking and attached the straps to it. The second stocking wasn't going on properly and I got impatient and pulled it up too quickly, it laddered.

There was a pause and I got a bit nervous after her warning. 'You clumsy bitch, you haven't even started for 5 minutes and already you have damaged the clothes I have given you. Well you need to be punished don't you?'

I couldn't think of any good answer, so just kept quiet.

'Girls have accidents occasionally, but this is too early, and you showed a shocking impatience. You need to learn to be patient and feminine. Did you do it deliberately?'

'No, no mistress, I am sorry, I really didn't mean too.'

I saw she had pulled out a cane from the side of the bureau. 

'OK John, you need to learn properly. Given it is your first time and the clothes were small, I'll give you only four now, but these will be hard and will hurt. After each one, count and thank your mistress for correcting your clumsiness and you'd better mean it! Now stand up, then touch your toes and keep your legs straight.'

I did so, though being well aware of how much a target I was for her cane - clearly exactly as she wanted.

The cane streaked through the air and hurt like hell. 'Ow! One. Thank you mistress, for correcting my clumsiness.'

The second was worse if anything and I struggled not to cry. I am sure she was hitting as hard as she could.

'Please Jess, I can't take it, it is too hard, please can I take the rest later, or do something else. Please - I am sorry to have damaged your clothes.'

'You disappoint me John, while I have heard the first time is the worst, I expected you to handle it. I suppose you aren't much of a man. OK, I will find another punishment. From now on you know what is coming if you misbehave. In the future, your lingerie will fit you better and if there is any damage, I will give you more strokes. I am sure you'll do better going forward. Stay there I will get some cream to help you.'

I lay there aching, what had I got myself into? This whole thing didn't seem such a wonderful idea now, it hurt!

She came back and slowly massaged the cream into the welts, muttering as she went along, 'you poor little bitch, your mistress is so nasty, I hope that you learn your lesson now and can be more careful.'

Eventually she finished, the cream didn't seem to be helping that much, it hurt like hell still.

I realized that I didn't have socks.

'Jess, please can I have some socks, I really don't want to go into the office where people can see the stockings.'

'This time yes, OK, however in the future you will have to learn to handle it with longer trousers and nylons. I will enjoy watching you worrying that someone will see you.

She smiled and gave me some socks.

We got in the car and she dropped me off at my car.

'Jess, please tell me where in the office is the key for the chastity belt.'

'It is in the top drawer of my desk. John, you can wear male clothes tomorrow and Saturday morning until I come to your place, though wash what you are wearing now and have it ironed. 

We can go lingerie shopping at the weekend. That will be something for you to look forward to. If you piss me off or I feel mischievous I will tell the assistant that the lingerie is for you. I know some of them quite well; some of them would find it very amusing. They will surely guess anyway as they know I am a size 8, and I guess you are size 14 or 16.

And John, thank you for taking me out on the date last night, it was one of the best nights of my life. I am so happy we have got together.'

She gave me a kiss immediately, and then put her finger on my lips indicating I should be quiet. She continued the kiss and started running her hands under my clothes and feeling the bra, panties, suspender belt and chastity belt.

'I like that, I can see why boys do it so often.' I blushed - which made her laugh.

We left, she drove me to the restaurant car park where my car was, and then she went on - she was travelling to another office in another town. 

After she got out, I drove on to the office feeling very self-conscious in the chastity belt and the lingerie, and the caning was really hurting.

When I got to the office, I got a text message from Jess 'Order the sexiest chemise you can find in size 14 for yourself, and some sexy lingerie you would like to see on me - size 8. Yours should be a proper sissy colour - white, cream, yellow or pink. Mine should be black or red and make you break the chastity belt! Get it delivered to my address. We'll talk more about what else we'll buy you. I suggest you be careful that the lines of the lingerie don't show through your clothes. That would be embarrassing wouldn't it? Maybe I should tell Amanda, what do you think?

Oh, and the cream was deep heat - it makes me wet thinking of you in your clothes and suffering. I love you!'

How could I respond to that? Well I couldn't. I was thinking that she had gone too far, in trips to the bathroom I could get some of the cream off and I applied some soothing cream, but still it stang like hell. 

I tried to do some work, but I still felt the after-effects of the caning, and her comments about lingerie showing through my clothes made me paranoid.

Eventually I got into work a bit and distracted myself. I kept away from others fearful that the lingerie might be visible through the clothes. At lunch time I realized the chastity belt was on, I was still horny and realized I needed to get it off. I wondered over to Jess's desk, it was on the other side of the floor. In our company, everyone sat in an open office and there are always people around, so I realized I wouldn't be able to spend too long at her desk without raising suspicions, and I would be seen.

I wondered over to her desk and tried the top drawer - it was locked. Oh my God! I walked away a bit spaced out and not knowing where I was going, I was trapped in the chastity belt until she came back. I can handle times in the chastity belt when I am ready for it, this time I was not ready for it.

I wondered around in a horny daze wondering what I had got into. I sent her an email telling her that her top drawer was locked. Then I went to a local coffee shop and drank a coffee, constantly thinking and felling the chastity belt and that I was so helpless.

Eventually I finished work and got home. I cooked myself something to eat, and logged on to my computer. I saw an email from Jess. 

John,

Thank you for taking me out last night, I really liked it and I am so glad we have got together. I hope the caning was not too much for you, but you have to admit you were a clumsy bitch.

I really hope you are as happy as me that we have found each other.

Love

Jess

I responded immediately.

Jess,

Thanks for the email. 

Well, what can I say, I had a hard day. But yes, I am very glad we are together and I really look forward to it! 

Don't worry about the caning. I now know I have to be careful  more would have been tough. I look forward to obeying you more. Please can we talk about limits at some time.

Another topic, I went to your desk today and tried the top drawer, it was locked! Is there a way of getting that key? I am not ready yet to be stuck in chastity like this until Saturday.

Love

John

I settled down in front of the TV to watch a little comedy, before long the phone rang, it was Jess. We said our hellos. 

'Hello my little sissy. How is the lingerie, do you feel sexy wearing it, you do still have it on don't you, and I can tell if you lie? And are you getting used to the chastity device. I have had several orgasms thinking about how helpless you are.'

'Err, the lingerie is fine - it is still on me, it's a bit small. But Jess, please tell me how can I get out of this belt. I need a few days out before the weekend.'

'Oh are you horny, how will you manage 2 weeks? And you know I will wear the sexiest clothes around you. Also I won't stop touching you. hehe'

'I can try and prepare myself, Jess please tell me where the damned key is. I really need out.'

She paused at this.

'John, you forget who is in charge in this relationship. You can't talk to me like that. Now it is early days, so I will give you some leeway, but in the future, I will punish you for non lady-like language like that. For now any kindness I had has gone. You will stay in that belt until the weekend and you give your choices to me OK?'

'Jess, please I can't handle this.'

A chill came over her voice, I realized immediately I had pushed things a bit far.

'John, I get exactly where we are my dear little bitch. There you are horny as hell, unable to stroke your little pecker, but you have made a bad mistake and challenged my authority. Now you have a simple little choice that a simple sissy like yourself can understand. 

You will stay chaste until the weekend and maybe longer and your Goddess will decide when you get out. 

Alternatively you can tell me it's over and I will tell you where the key is, and you can get it tomorrow. If you leave I won't tell anyone, but I think we both know we both want to continue.

If you wish to stay with me, then I need to know that you accept I am in charge, and you need to apologize and I wish to hear how you worship me and how you regret that insolent tone you used to address me. Have a think and make up your mind, and call me back within 5 minutes. If you apologize, some groveling would be appropriate.'

She hung up. I looked at the phone.

Talk about focusing the mind! After 10 seconds, I knew that no matter how horny I was I would regret blowing any chance with Jess. I called her back straight away.

'Mistress, I am really sorry I had a strop like that. You are in charge and I regret talking out of turn like that. I am finding it very hard and I am very horny, but yes you make the decisions, and thank you for taking the decisions so I don't have to worry about them. I apologize for talking out of turn.'

'That's better sissy. Now I don't feel any guilt about telling you that you are stuck in chastity until the weekend. I planned the drawer to be locked this way. Though I meant to leave a key with someone at the office, but I got distracted. What I will do now first thing tomorrow is go and buy a vibrator and have a laugh and an orgasm at your predicament, and probably several huge orgasms sitting on the ladies toilet.'

That was like a kick in the balls. 

'When are you getting back? When can I get out of this belt, and when does your friend want to put it back on me?'

'Well, I planned to take it off at the weekend, though now I'm not sure, maybe we should just keep it on you until she comes on Sunday, and she can just verify it is locked on. You'll have to be extra nice to me. Let me think about it. I can get back Friday night late, and can go to yours. 

By the way, I owe you a punishment for your clumsiness with your pretty stockings. I want you to write lines for me. I will email you later how many and what exactly. OK?'

'Err yes mistress.'

We slowly said our goodbyes. I started thinking again about what I was getting into, though this time feeling a lot more positive about it, though still very horny. 

Later that evening I got an email from Jess.

Hello Sissy!

We need to give you a girl's name, sissy is too impersonal, think of a few girly names that I can call you and I will choose. Also, I want to call your penis a girl's name, that should be a suitable emasculation for you.

Ok, so you are to write 50 lines for me. There is to be NO mistakes, it must be clean and tidy handwriting, easily readable and it has to be on pink paper, and you are to draw flowers and birds on the paper at the end. I will hang it on my bedroom wall - hehe'

The line is 'I am the prissy chaste sissy of Mistress Jess. I love dressing in pretty frilly maid's uniforms and sexy lingerie for her amusement. I love staying chaste, horny and frustrated knowing that this turns Mistress Jess on, while she has multiple orgasms.'

On Friday night, I will come to your house. Wash the lingerie you wore today and wear it, and no other clothes. Don't drink anything before I get there, and buy some girly alcohol, no beer or hard liquor for you! Also, make sure your place is clean and tidy.

Don't forget on your lines, put lots of pretty flowers and birds and you must also put some bunnies, princesses and mermaids on there too, at least one of each on every page, normally more. The pictures should be coloured - several different colours.

No mistakes at all, if you make a mistake, you cannot submit that paper, and will have to start again - that includes the pictures, and the writing must be small.

In the morning, write and tell me the girly names you have thought of.

Love 

Goddess

I groaned. This would be hard. 

I had a think where I could get pink paper. I only had one day to do the lines, so it would be a squeeze. I finished the TV program, then went online and found some very cute satin chemises and ordered them to Jess's address.

Then I gave the place a quick vacuum and cleaned what I could. I would need the next evening for doing the lines. I went to bed early.

I woke early the next morning my penis straining against the belt. I got up and washed the lingerie she had given me. I normally hang my clothes outside, but felt afraid the neighbours would ask questions if they saw lingerie there. I had to find an alternative arrangement inside.

I checked when the stationary shop opened. I saw it opened early, so after giving my place another check and clean, I went down to the stationary shop and bought a pack of pink paper, and some different coloured pens.

I got into the office early and then emailed Jess the girly names for myself and my penis. It wasn't so simple, my choices were Jenny, Daphne, Alice, Phoebe, Belle, and Aurora. I then managed to do slightly over 20 lines before anybody came in. Eventually I had to abandon them for fear of some nosy person, I wasn't sure if I would get a chance to continue before the evening. I also panicked slightly about someone finding the lines, how would I explain that? In the end I locked them into my drawer.

The day went slowly. About half way through Jess called me and told me that she had had many orgasms with her new vibrator, and she was having trouble keeping quiet when in the ladies toilet. She also asked me what colour I prefer yellow, pink or white. I told her pink and white. She told me to go and buy some small locks, locks that she would use to lock my bra and other things onto me.

The idea of a bra being locked onto me scared me, but I said nothing.

She told me I should probably buy darker shirts in the future, 'after all dear, it would be so embarrassing if others could see your bra and pantie lines through your clothes. You also have to worry about people putting their hand on your back, what a surprise they would get! Hehe.'

After she had screwed with my mind, she let me go. I took a short lunch break knowing I could leave earlier. I had lines to finish!

I went home buying the small locks on the way, and continued the lines, and managed to get to over 45 lines before hunger set in. I cooked myself something light, and then finished the lines. It was boring and tedious work, but I kept concentrating. At the end I started drawing on the flowers, birds, bunnies, princesses and mermaids. The drawing was really hard and probably not very good - I have always been bad at drawing, so I had to be very careful. I coloured them in at the end.

Eventually I finished and realized it was quite late. I pulled all the curtains closed, and gave the place a once-over to make sure it was as clean as I could do. I took off my clothes and put on the lingerie she had given me. I felt a bit ridiculous. 

I sat down and watched some TV. A bit after 10, I heard a car park outside and I heard her come in the back door. I got up to greet her. She gave me a kiss, then stepped back to have a good look at me.

'You look really pretty Belle, and how is Phoebe doing?'

It was clear I was to be known as Belle from now on and my penis was going to be Phoebe. Her complimenting me as being pretty embarrassed me and that got me hard which hurt and she in turn thought it was hilarious, 'Oh you pervert, you get hard when you are told you are pretty and called a girl's name, you really get off on humiliation don't you Belle.'

'Yes, Mistress,' I could only agree.

'Well Belle, I want to make you even prettier, so take off the lingerie you have on. I have some presents for you.'

I took off the lingerie and she gave me a cream lacy bra to put on. She also gave me a satin basque which had clips to the silk suspenders she gave me to put on. She also gave me a pair of cream satin French knickers.

'Oh you are sexy Belle, I can't wait to buy a strapon and I'll fuck you all night. You'd like that wouldn't you?'




Helping Jess Pt. 03



I couldn't disagree, 'Yes mistress, I would like that.'

'Well we need to go soon, please go and get 2 pairs of socks and show me the coats you have.'

I went and brought some socks which she bundled up and put into the bra. 'Ah, that's better, a bit of cleavage,' she said while running her fingers along the outside of my bra and over the basque. 'I wasn't sure, but I like the fact you have 2 straps on each shoulder, these flimsy straps are so feminine and pretty. Also, they are like a delicate prison, remember that if they get damaged I will whip you harder than this morning.'

I gulped at that. I then showed her my coats; she chose the long raincoat that buttoned up. She told me to put it on and a pair of shoes, give her the house and car keys and she would lock up, and I should wait by the car, and she would be driving.

The street was quiet thankfully as she took a while before coming out and locking up. I was paranoid that a neighbor might see me and my exposed legs in satin stockings.

When she came out, she didn't open the car door, rather came round to my side and gave me a deep kiss. She ran her hands under my coat and felt all my lingerie. I felt totally helpless and very submissive. I was also very turned on. 

Eventually she opened the door and let me in to the passenger seat, but she didn't get into the driver's seat yet, she got in the back. 'Put your hands behind the seat,' she ordered.

I did as I was told and she handcuffed my hands behind the seat. I realized how powerless I was.

She then climbed into the front seat and gave me another kiss.

'This will be an exciting journey won't it Belle, you can't do anything now.' She undid the top button of my coat.

Oh my god, I realized what a predicament I was in, she could unbutton the coat and expose me to the world. I was horrified.

'Please Jess this is scaring me.'

'Belle, you are so pretty I want to admire you and have my way with you, and we have to share your beauty with the world, don't we?'

'Yes mistress, but please can it be done in a controlled way?'

She undid another button, and pulled the lapels apart so my 'cleavage' was beginning to show.

'Belle, that second button was because you complained. Keep complaining if you want me to undo more buttons. If you continue to piss me off, I might just undo all the buttons and leave you here while I go and have a drink in a pub.

'I'm sorry mistress, I'm sorry I just want to please you.'

She did up a button. 'Good girl, you are learning. We will talk about what I want to talk about. Now I hope that you will be an interesting and cheerful companion for me, otherwise I will expose you to the world.

Now Belle, the situation is the following, we have a bit less than 20 minutes to my place where we are going to spend the night. You have 6 buttons on your coat, 1 is already undone. I have set my phone to go off every three minutes, and every time it goes off, I am going to undo a button on your coat. If all are undone, I will open it up. Now you need to keep talking to me and make me happy.'

She started the car and pulled out, she started the timer.

Oh shit, I thought, this is hell. I had to be careful not to complain as that would simply speed up the process.

'Mistress, Belle doesn't want to display herself to the world, Belle is scared and would prefer to keep her beauty to Mistress.'

'Hehe, nice comment Belle, keep thinking and you might find a way to stop such a thing happening.'

I started thinking hard, but couldn't get anywhere. The timer went off, she reached over and undid the next button, 4 left.

'You look beautiful as ever Mistress.'

She laughed at that, 'flattery is a good attempt, though it won't stop this process.'

I groaned. I looked at her, her toned legs in her business skirt and an evil smile, knowing the power she had over me.

'Well for the record Mistress, it is true, you are stunning, and I say that knowing it doesn't help me in this situation.'

She smiled at that, and ran her free hand over the basque and reached down and stroked the cage and my balls.

'Mistress, can you give me a hint what I need to do, please?'

'There are lots of things you can do Belle, but you need to think what would make me happy, what do I like? A general comment I quite like the idea of you being a bit of an airhead - at work you are very serious and professional, but if you have to babble about all the pretty things that get into your head, that would amuse me. Though for now I am looking for something specific.'

My brain was whirling, but the embarrassment and fear was killing my thought process. Generally I control my mouth to make sure I don't say anything stupid, she wanted me to let go.

The timer went off again, I was beginning to hate that sound. She reached over - in the middle of driving - and undid another button. 3 left. The last one was very low so hardly counted.

'You like control Mistress, you like seeing me in chastity and being submissive. You like making me do things'

'Yes dear that's right, keep thinking. 

I was wondering, shall we take the long route, it is such a pleasant evening to have a drive isn't it?'

It was cold and beginning to rain, so 'pleasant' certainly wasn't the adjective I would have used, but I wasn't in position to argue. I didn't know what I could say. 

The timer went off. She reached over and undid another button, 2 buttons left. She was at a traffic light, so leaned over with both hands and opened up the coat to reveal my basque. The top of the suspender belt was visible.

'Oh you are gorgeous Belle, you are going to have to give me multiple orgasms later, I already feel quite wet.'

She gave me a quick kiss with a bit of tongue before the light changed.

It was so embarrassing and humiliated I was getting very hard which caused me pain. She noticed.

'Oh my, you get off on this don't you? The embarrassment and fear and being dressed up as a girl, Phoebe is getting very hard down there isn't she?'

It was actually painful in the chastity belt I was so erect, I could only nod in agreement.

'Well keep thinking dear, because there are only 2 buttons left. I have to say this is one of the nicest drives I have had in a long long time. It is very amusing; I wish I had done this before.'

I didn't know what to do or say.

'Please mistress, please don't do this to me.'

'Belle, this is disappointing. I am going to take that as a complaint so I will undo another button, and I will reset the timer.'

She leant over and undid the button. She was still driving, but she managed to undo the button with one hand. I was in shock.

'I was thinking that maybe I could go and get some take away Chinese. Would you like some take away dear? Don't worry, I would go in and get the food, you can stay here.'

I just wanted to get back and stop this torture.

'No thanks Mistress.' I said knowing that if I said more, I would probably annoy her and get the remaining button undone.

'Mistress, I can't think straight I am all flustered with this situation, please can you help me?'

'You really can't work it out Belle?'

'No mistress, please I'll do whatever you want.'

'Ah you silly bitch, what do you think I want? Think about me, not you.'

The timer went off, I squirmed, scared. She laughed.

''Oh this is a brilliant game.' She leant over and undid the last button, and reset the timer.

'After the next timer, I will open up your coat wide for the world to see, and I am going to turn on the light in the car. I think I'll go right here, and we can drive along the main street, I am sure some of the young girls who typically smoke outside the local pub would find you very interesting. Maybe I should ask them to suggest what I should do to you.'

I had no idea if she was serious, but I was terrified.

'Keep thinking Belle, even flustered you know what I like. Tell me what I like.'

Fear was doing my head in now. I tried to keep talking.

'You like controlling, you like teasing, and you like scaring, screwing people's minds.'

'Yes and what is your situation, what is making you act differently with me?'

'The chastity and female clothes I guess, you like controlling my orgasms and making me wear female clothes and being scared of being found out.'

'Yes, keep going.'

The timer went off. 'Oh brilliant, this will be fun, look a group of girls up ahead, they will love you, I'll drive slowly.' She reached over and pushed and pulled the coat aside, then she turned on the light so people could look into the car. Everything was visible. 

Again the humiliation was making any concentration impossible. Jess was driving slower.

'Oh you want me to stay locked up. Please mistress, please keep me locked up until your friend comes. Please don't let me out.'

'I don't believe you Belle, you're just saying it so I will cover you up.'

How much crueler could she get? The car was barely crawling now; she was clearly increasing the window of opportunity for the girls to see me...

One of the girls started looking at the car and pointing at me.

'Please Mistress, please please keep me locked up until your friend comes, please cover me up, I'll wear any girly clothes you like and stay chaste and help you have massive orgasms. Please mistress I beg you.'

'Do you really mean that Belle?'

'Yes, yes Mistress, please please please keep me locked I really mean it, please don't let me out. Please cover me up. Please dress me up as you like as your doll, please keep me horny and desperate and I promise I'll help you have the best orgasms ever. Please mistress.'

She turned the light off and sped up. The girl who had seen me was still looking, but it seems her friends were too slow to see me. 

I think my heart rate had trebled and I still felt it. She pulled the coat together again to cover me.

After a few minutes she pulled into a quiet street and turned off the car. She stroked me.

'Belle, you have made me very very wet, and very happy. I love the way you are always thinking about my pleasure.'

She sat on me and gave me a big kiss, and ran her hands over me, stroking me and giving me a big feel.

'No doubt before this journey you never thought you could handle being exposed like that did you?'

'No mistress, you scared the shit out of me.'

'You have a filthy mouth for a girl Belle, no more swearing from now ok? Though I have to say it amuses me at the same time.'

I nodded.

'Now can I trust you? I am going to ask you something very hard.'

'Yes mistress.'

'Good, I am not going to drive on any more busy streets, but I would like to uncuff you, take off your coat and put it on the back seat, and then recuff your hands behind your back, not behind the seat. Do you agree to this? I promise not to go on any busy streets, and to avoid people, and to go straight home, however having you in your bra, basque, panties and suspenders would turn me on with the control I have. Do you trust me and is this OK?'

I was mentally exhausted and I guessed I could handle that after what had happened before 'yes Mistress.'

She climbed round the back undid the cuffs, she told me to take off the coat, and then redid the cuffs. Before starting the car she sat on my knee again and gave me a good look.

'You are so pretty Belle, it really turns me on to see you like this, so helpless and so under my control. I'd like you to keep thinking how you can please me more - by telling me your fantasies and what embarrasses you. We'll also work hard on making you even prettier. I have some ideas, but I want you to suggest what I should do to you.' 

She stroked my arms and gave me a hug, then moved over to the driving seat.

'I can't wait until I buy a strapon and take you properly Belle. Would you like that?'

'Yes mistress.'

'When I take you with the strapon, I want you to fake an orgasm just like a girl. After all you want to make me happy don't you? I am sure you had several girlfriends who faked for you, and made you think you were a great lover.

By now I was properly in sub space, just going with it. I didn't respond.

Eventually we got to her house. She opened the car door for me and put the coat over my shoulders. 

I walked up the path somewhat nervous about what else could happen, and well aware of my stockinged legs. I also realized I was deep in sub space with a gorgeous girl controlling me - one of my favourite places. Life was good, even if it scared the hell out of me.



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.




Helping Jess Pt. 04



We finished the meal and headed back. In the evening we went out for a meal and then to the cinema afterwards. When we got home, we made love like a normal couple. We fell asleep in each other's arms.

The next morning was nice waking up and making slow love. We went out for lunch and eventually made it back mid afternoon. 

Jess was clearly nervous that Claire was coming, again reminding me not to say too much. She wouldn't talk any more about why, or who this Claire was. 

 Eventually at four o clock, the doorbell rang, Jess answered and soon walked into the living room with Claire.

Claire was gorgeous, absolutely stunning, about 5 foot 8 or 170 cm by my guess. She had long black hair, which had a hint of the Asian exotic about her. Her face was perfect, and she had a slim perfect body. She was only wearing too-large jeans and a t-shirt, but she had the kind of body that could not be hidden, it was clear that she was stunning even if you put her in very baggy clothes. She was wearing some elegant shiny boots with stiletto heels and I was thinking what it would be like to kiss and suck on them.

Eventually I realized she was holding out her had for a handshake and had greeted me though I hadn't heard what she had said. 

"Hi I'm John, good to meet you."

She gave a small smile at that. 

"I see you like my heels, most boys do, maybe one day you can polish them if you behave."

Jess looked a bit annoyed. I could see I needed to be careful, I had heard of girls getting jealous and Claire was something special.

"Thanks for helping here. I don't have much time, so can we get down to business. Can we get it locked up first. I am not going to touch you, but I do need to see that you are locked up, so please pull down your trousers and let's get it on."

This directness was a surprise, but I remembered Jess's request not to say much, I simply undid my trousers, pulled down my boxer shorts and revealed my penis, which was getting hard. I could have died, why did it have to get hard now? Well because I knew it was was in a room with 2 stunners, and particularly Claire.

I think Claire found it a bit amusing, but Jess certainly wasn't happy. She could see I found Claire attractive, I could see why she might be annoyed.

"Erm, I'm sorry about this, could you give me a few minutes and I will put it on on my own."

I could tell Jess was not pleased but she tried to keep it out of her voice. "I suggest you go into the kitchen John, there is ice in the freezer."

Claire added, "Be quick please, I need to get to my next appointment."

I rushed into the kitchen. I found the ice and applied it to my penis. Eventually it cooled enough to get smaller and get the cage on. 

I went back into the room. Jess and Claire were talking about something, it sounded a bit like an argument. They quietened as I came in. It was strange with Jess being nervous before and now the atmosphere was tense, I had no idea why.

I pulled down my boxers and jeans and showed the cage.

"That's better," said Claire holding onto the cage. "Now, let's find that lock."

She pulled it out of her bag. It was a bit big, but I didn't want to talk into the awkward silence in the room, particularly after Jess warning me to be quiet. 

Claire got the lock ready, then asked "Are you ready?" she looked into my eyes. I had to look back. She was so good looking, possibly the best looking girl I had seen and now locking me up for 2 weeks. She smiled as the lock clicked. I felt quite powerless and helpless.

"Good, now that is over, let's handle the questions. This time it is quick, there will be more questions in the visits over the next 2 weeks. I will visit every 3 or 4 days."

She pulled out a piece of paper.

"Just 2 questions, though it might be more depending on your answer. The first question is how often do you have an orgasm. What is the average?"

I was a little embarrassed being asked such a question from such a beauty, and also having my girlfriend in the room, but I had been through some of this before with Jess. 

"Well on average it is once a day I guess."

"I guess? Don't you remember?" her curt tone surprised me.

"Yes, I do, on average once a day."

"And what is the longest you have gone without orgasm since you were eighteen?"

Well that was a week. I had already told Jess this, so I had to stay consistent.

"Well I guess it was a week."

Claire got annoyed at my tone here. "Jess, looks like you have a real clever one here?" sarcasm dripping from her tongue, "Do you think he can "guess" if he is a boy or a girl?" she turned and looked at me, "it's very simple dear, these aren't hard questions, now let's try again, what is the longest you have been without an orgasm?"

"It was a week, 7 days."

"Yes a week is 7 days, congratulations Einstein."

She was being quite a bitch, she was intimidating with her beauty, her power over me with the key and her tongue. I said nothing, I was getting nervous.

"Well there are some follow-up questions – why so long? Your average is like most male worms is just a day."

She had just called me a male worm, I was a bit shocked with this turn of events.

"Well I have had one of these attached to me before and someone else held the key."

"Someone else held the key? Who was this person to you? A girlfriend or a mistress?"

"It was a mistress." So few questions and she had found out one of my deepest secrets. She looked surprised, and then I realized she was thinking, probably thinking of what other fetishes I had.

"Well that's enough for now." I was surprised she didn't ask more questions, but then I realized she would have plenty of time later.

She turned and looked at Jess, "So Jess, it looks like your new boyfriend visits mistresses - I guess he couldn't get girlfriends before. He also seems a bit weak minded. I need to get going, Is Wednesday evening at 7.30pm ok for the next visit? Probably just 20 minutes."

Jess nodded agreement. Only later I realized I wasn't asked, it was just assumed I would be there. The comment about girlfriends was a shock as well.

Claire put her coat back on. I suddenly realized there hadn't been any confidentiality agreement or anything.

"Claire, err, is this under a confidentiality agreement or something? I mean this whole situation is embarrassing for me."

She faced me and completely ignored my questions, "On Wednesday I trust that you will have a bit more steel and memory and not be such a weak minded girly boy. People who guess piss me off, they waste my time, so don't guess. By the way, call me Miss Coombes, not Claire, we don't know each other on first name terms yet."

I nodded in shock to this beautiful woman who had the key to my cock.

She left. 

Jess saw her out and came back, "You idiot. I warned you to keep quiet. You've annoyed her now. You'd better leave. We can meet at lunch tomorrow."

It was a dismissal. I went out to my car and drove home, wondering what the hell I had got into.