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.