Helping Jess Pt. 03

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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.

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  • COMMENTS
2 Comments
ChastityBoyChastityBoyalmost 8 years ago
Lovely Story

Hope this continues many more chapters. Love to be in his shoes being controlled by this beautiful Mistress.

mrwidehorizonsmrwidehorizonsover 8 years ago
Great series!

Totally loving where this is going. Can hardly wait to meet the friend behind all this. Very original premise and wl written. 5 stars!

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