Our Holiday ends

Diane and I are on holiday. Diane has agreed to be in some form of bondage for the whole holiday. The previous posts are here, here, here, here, here and here.

Day 19

We decided on another day at the beach and Diane requested 12 strokes of the cane to reduce the number of days in the chastity belt.

I have delivered 9 of them when there was a knock on the door. I rested the cane on Diane’s bum and told her “Stay still, if the cane falls off then you do not get the rest and you lose the two days in the belt.”

I opened the door and Dave and Debbie were there. I invited them in and said, “I won’t be a moment, went to Diane in the bedroom and quickly laid down the remaining three strokes. I gave her the bikini I wanted her to wear.

I re-joined Dave and Debbie saying “Diane will be with us in a minute.”

Diane joined us soon after and offered to make coffee. As she walked pass us I could see the vivid red lines on her ass. David and Debbie saw them and they looked a little alarmed until Diane said “Don’t worry, I asked for the stripes.”

Debbie produced the bikini we had lent them last night saying “God that was intense. I nearly had an orgasm as we walked just the couple of hundred yards back to our villa.””

Diane smiled “I know. My darling husband has made me swim in it, as well as walk to the beach. The couple who made certainly know how to make life interesting.”

Small talk followed and we agreed to meet up later for a drink and dinner.

The day passed uneventfully and Diane enjoyed her day in the sun. As we prepared to go out I handed Diane the tack bra as well as the blouse and shortish skirt. Before she put them on I inserted the bullet vibrator and locked up her pussy again.

We met Dave and Debbie and when the girls hugged Diane winced a little. This did not escape Dave’s notice. I said “Don’t worry; Diane is in for a fun night with the three of us.”

Debbie raised an eyebrow before Diane said “I’ll tell you about it later.”

The dinner went well with good company. As we walked back to the villas I quietly asked Diane “Shall we invite them to join us tomorrow on our sightseeing trip?”

“Why not, it could be fun.”

I turned to Dave and Debbie and asked “Tomorrow we are going to the bottom of the island. Would you like to join us? The only stipulation is that Debbie is to join Diane in having some sexy fun whilst we are out.”

To the apparent surprise of Dave she said “well, seeing how you two enjoy yourselves, I don’t see why not.”

Day 20

They came round to us at about 10 after I had made sure Diane was appropriately locked up with the magnetic eggs inside her and added the nipple stretchers.

As they entered Debbie said “we talked last night and I hope there is nothing like the slaps we heard yesterday morning.”

“No, nothing like that.” I replied as I handed Debbie the bikini she wore home a couple of nights previously as a set of ben wa balls.

I said “This is the sexy fun. Go to the bathroom, insert the balls, and then put the bikini on.”

She did as she was asked, and came out without having locked the chains together. She turned to Dave asking “Please could you do the locks as I can’t get them right.”

He did as asked making sure that the one that went up her bum was tight.

The drive took about an hour and Debbie stayed relatively still. We walked around a trail that went through the forest to a set of ancient ruins. Debbie was struggling with the sensations as the bikini bottoms stimulated her with the critically located beads. She turned to Dave saying “shit, did you have to do it up so tight?”

With a smile he said “I thought you would enjoy it. If it’s making you horny then that is just perfect.”

At the ruins there were a few people milling around when Diane said “Now have you ever felt so horny with people around?”

“No, never. These balls are maddening and the bottom is hitting just the right place. I’m not sure how much more stimulation I can take.”

“Just go with the flow.” Replied Diane. “Just hold back and when you eventually get to orgasm it is even more intense.”

Debbie nodded. We walked back to the car and after a short drive we parked up and followed a short trail down to a deserted beach. I passed Dave the key for the bikini and said “this is a clothes optional beach, so it is up to you.”

Debbie said “Please let me out as I can’t take much more direct stimulation.”

He laughed saying “Only after we have had a swim.”

She groaned as the rest of us stripped off.

We enjoyed our swim and the effect of the water, the ben wa balls and the bikini had Debbie coming hard with Dave holding her tight. We left the water and Debbie was released from the bikini.

Debbie was fascinated by the nipple stretchers Diane was wearing and we talked a lot about the gentle torments that Diane was being put through whilst on holiday.

The two of them were fascinated by the whole subject, as they had never really done anything more than a little mild bondage in the bedroom.

Day 21

The last full day of our holiday was a beach day. Before Dave and Debbie joined us she asked me “How many days have I got still?”

I replied “the count is now seventeen.”

“I think I can take 24 strokes.”

“Are you sure?”


Diane bent over, held her ankles tight and I delivered the requested 24 strokes. When I had finished Diane had watery eyes and a nice reddened bum.

We were soon joined by Dave and Debbie. They had washed Diane’s bikini and returned it. I smiled as it was handed over and said “Diane, I think you better wear that one today.”

She didn’t react as she went to the bedroom and changed into it. I had her turn around, unlocked the lock at the back and pulled up three links so that there was extra pressure on her clit. She wisely said nothing.

The day at the beach was fun and relaxing.

That night Dave and Debbie invited us to join them for dinner at a local taverna. I had Diane wear the tack bra again and Debbie commented “I see you are wearing a bra tonight. I thought you didn’t normally wear one.”

Diane smiled as she replied “well I don’t like to, but part of the agreement for the holiday fun was that he chose my clothing. I had no choice in the clothes he brought and he added a few toys to keep life interesting. Other than my bikini tops, this is the only bra he brought. It is not a normal bra as it is a bit tortuous, but fun.”

Debbie raised an eyebrow before asking “What do you mean?”

“I’ll show you later back at the villa.”

After the meal we returned to our villa and with my permission, Diane took off her bra and handed it to Debbie. Debbie examined it and said “that looks nasty.”

“It’s not that bad. It is actually quite stimulating. You’re just a little smaller than me, so see what it feels like for yourself.”

Debbie did as asked and once it was on, she said “I am surprised, I can feel the pins but they are not painful.”

“No, if they are in a properly fitted bra, the sensations are even more intense and they don’t break the skin.”

There was little more to say, and it was late when we finally got to bed.

Day 22

As our flight was not until the early afternoon, we had plenty of time to pack and get to the airport.

About hour before we were due to leave I asked Diane “You have 14 days in the belt when you get home. How many days off that would you like to earn before we leave.”

“All of them.” She quickly replied.

“That’s 84 strokes. You have never had that many with this little cane. I don’t think you can manage it.”

“I can and will.” She replied defiantly.

“Usual rules apply.”

“Of course. And why not up the ante, if I don’t manage them all then it is 4 weeks in the belt.”

“You’re on.”

She bent over as I retrieved the cane and I started to lay down the strokes. After 30 strokes had landed she was struggling to hold her position. I continued up to 50 strokes when I said. “OK, a few moments break and you can stand up without penalty. She did and felt the fire on her bum. She stretched for a minute and then bent over again pleading, “Please make them quick.”

I then quickly laid down the remaining strokes and as the last one landed she started to cry with the intensity of the pain. I held her tight and let her recover from her ordeal.

As Dave and Debbie had not got a hire car, the previous night we had offered them a lift to the airport which they gladly accepted.

They arrived and once all the cases were in the boot, Diane gingerly sat in the front. Debbie noticed this asking “what’s happened?”

Diane replied “I have earned my way out of two weeks in my chastity belt.”


“84 strokes of the cane you saw the other day.”

“What?” She exclaimed.

Diane explained all, and the two of them listened carefully.

At the airport we went through security without any problems to Diane’s relief.

After we had disembarked from the plane waiting for our luggage Dave asked “Debbie and I have talked a bit, can we meet up some time and talk more about your lifestyle.”

I told Diane about this in the car as we drove home. She remarked “Not another couple we need to train?”

“I thought we had started already.” I replied.

Wicked Wednesday

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2 Responses to Our Holiday ends

  1. Such a pity the lovely holiday is over!

    Thanks for sharing your experiences.

    Rebel xox

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