Losing their virginity?

We continue from last week where Liz was tormented for a day. In addition I have tried to incorporate this week’s Wicked Wednesday prompt.

Diane had already got up when I woke with my wrists and ankles cuffed and chained together. I noticed that the keys to the locks were on her bedside table. I retrieved them and managed to free myself from the cuffs.

I got up, let Liz out of her cage and then tried the keys on my device and found that it opened. I was relieved to be rid of it.

I found Diane in the Kitchen preparing breakfast and she had a big grin on her face when she saw that I had released myself. Liz soon joined us. I made Diane sit at the table and cuffed her wrists together. Liz looked a little surprised until Diane said “we have this rule that if the person restrained is able to escape, then the roles are reversed. So Charles is in charge for the rest of the day.”

I smiled at Liz saying “Don’t worry, today will go as Diane and I had already planned. Now what did you think of yesterday?”

She looked relieved when she answered “I was so worked up much of the time, that I was praying that you would let me cum. I suppose the day was really one of frustration. That corset last night really hit all the right spots to make me so horny.”

Diane said “That is exactly what we hoped. Yesterday was all about frustration and sensual fun. Today will be rather different.”


I replied “Yes, Today we had planned that you will find out your tolerance to pain. Diane will help you process the pain and I hope allow you to derive pleasure from it. ”

I continued. “Diane, it is time for you to get the first torment ready.”

She went to the play room whilst I still talked to Liz. “Before we go any further one question that you did not answer on the questionnaire needs to be resolved. Have you ever had a woman go down on you or the other way round? If not, what are your thoughts on it?”

“To answer your first questions, no. As for the second, I am not sure about it. I have read that a woman is usually better at give oral attention than most men, and whilst I would like to find out some time, I am not sure about it today.”

“OK, I understand. Diane has the same view as you. I won’t force you do anything you don’t want to do. If you feel like trying it let me know as Diane will have no choice. If you do want to try it, you will not be punished if you cum, but if you make Diane cum, she will.”

Diane returned saying “Everything is ready master.”

We all proceeded to the play room where Diane cleared the playroom ready for the first torture.

“Now Blindfold Liz, cuff her hands behind her back, so she can wait a few minutes.”

“I ran a rope from two hooks that were in the ceiling, had Diane straddle it. I then clipped a pulley to another hook an proceeded run a string from her nipple piercings over the pulley connected to about a half pound of weights. I had her get onto tip toes, set the string length to the right length and then set them on top of a stool. I then tightened the main rope so that it was just touching her pussy lips. I picked up the weights before I removed the stool and let them touch the floor.

I made the same arrangement for Liz using Clover clamps as her nipples were not pierced with only 6oz of weights. I removed the blindfold and said “Now this is an interesting dilemma for you. When your calf muscles ache, you want to relieve them thus torturing your nipples and pussy.”

I watched them carefully as they squirmed and avoided the tortures if they relieved the aches from their calf muscles. Liz was the first to drop down and although she did not make a noise her grimace showed how she was suffering.

I left them there for half an hour with both riding the rope. I let Liz down first, leaving the clamps on, before I released Diane except for her cuffs.

I went over to Liz and with a gesture Diane understood what she had to do. I said “Liz, when I release the clamp it will be painful, but Diane will help releive it for you. I took off the first clamp. Liz winced and Diane set to work suckling Liz’s nipple until I was happy that she was ready for the other to be removed. Diane repeated the exercise and afterwards Liz’s nipples were like bullets. She said, “That is making me so horny.” She pulled Diane in close and started to kiss her all over her neck before pleading, “please go down on me.”

Diane looked at me, I nodded before she said “are you really sure?”

“Yes, I am sooo aroused, I want to cum and I want you go down on me.”

Diane dropped to her knees and started to suck and tease Liz to even greater heights of arousal. I released Diane’s cuffs and quickly she reached up and started to massage Liz’s breasts. I guided them both to the bench where Liz laid back and soon panted and groaned with her arousal.

Liz did not hold back and soon came hard with Diane sucking up all the moisture that escaped from Liz’s pussy. Liz twitched a little as Diane cuddled her to let her recover.

When she had recovered, Liz said “Wow, that was one of my best ever orgasms. I think I should thank Diane appropriately.”

They switched positions on the table and soon Liz was working her lips and mouth on Diane’s body. I watched Diane struggle to hold back, but Liz continued her work eagerly. Eventually Diane could not hold back any longer and came hard.

Once Diane had recovered Liz said “I suppose now I should recognise I have lost my girl on girl virginity!”

I laughed “well that applies to both of you. Diane, were you given permission to come?”

“No master.”

“Punishment for you later, and as I know from my experience before I met you, Liz can wield a cane very effectively. I think I will let Liz do the honours.”

Diane added “I know, I saw her cane you once.”

Wicked Wednesday

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7 Responses to Losing their virginity?

  1. I like how you used the prompt here 🙂

    Rebel xox

  2. you slipped the prompt in their seamlessly!

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