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 görükle escort 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.


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.



I responded immediately.


Thanks for the email.

Well, what can I say, I had a hard day. But yes, I am very glad we are together görükle escort bayan 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.



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 bursa escort 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.



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?’

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