Helping Jess

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.