Summer Holiday

This episode is in a few parts and recalls what we did on our late summer holiday in September. You can read about the preparations in last week’s post.

In the privacy of our room, after checking in to our hotel for the night, Diane was ready to go for dinner when she asked “Please can I have a different blouse for tonight?”

My reply was quick and simple “No.”

She pouted a little before I continued “You offered to be in some form of bondage for the whole holiday, you also agreed to me deciding what you will wear. Any more of this and I will make this blouse even more revealing by removing another button.”

“I’m sorry for asking.” She replied.

Day 1

We were up at around 5.00am and got ready to catch our 9 o’clock flight to Rhodes. Diane was required to wear the same clothes as the previous evening. Just before we left our room I told her to stand still, raise the front of her skirt. I unlocked the small padlocks on her pussy and replaced them with plastic security tags.

She was a little dismayed that she was still ‘locked up’ but wisely said nothing.

As we went through security at the airport Diane was pulled over and the wand that the female member of the security staff used was passed over her. It detected her nipple rings and piercings around her pussy. She was asked why her groin and breasts were setting the detector off. She quietly replied “I have a piercing in each nipple, two on each of my pussy lips and one on my clit.”

The woman smiled before calling over her supervisor and after a little conferring Diane was allowed to proceed with the comment “I suggest you don’t wear them on your way back.”

I patiently waited for her as this happened and we made our way to the plane. The flight was uneventful and we were soon settled in at our villa. After my shower I laid out the light, discreet full length dress with spaghetti straps that Diane was to wear for our meal. Before she put it on I asked “you have a choice, either your pussy stays locked up or your nipples have some fun. Which is it to be?”

She immediately replied “Nipple fun please.”

I picked up a short chain and two padlocks and attached it so that her nipples were gently pulled together with an equal length at each end hanging down.

As she started to put her dress on she squeaked a little as she felt the tug on her nipples as she reached around to get it just right. I was also pleased as her slightly engorged nipples poked at the front of it.

Her only comment was “this will be an interesting experience, as I am already getting turned on. I hope that you will be ready for me later.”

I laughed “aww, and as you are in bondage our new rules about orgasms apply.”

She sighed.

Dinner was uneventful, and at the bar afterwards it was clear that a few of the men were fascinated by the top half of Diane’s dress. When we got up to leave, I said “Don’t smooth down your dress; let them gawp at your sexy legs.

She blushed slightly before we walked out of the bar back to the villa.

Back in the villa, she soon removed her dress and waited patiently while I undressed and got ready for bed. I locked up her pussy again before I released her nipples from their mild restraints.

As I cuddled up to her she said “I am rally horny and please may I have an orgasm.”

“I thought about this for a moment and said “If you are that horny, let’s add some jeopardy into making this holiday even more fun. I had already decided that over the three weeks you will have 21 orgasms. If we suspend the ‘no orgasm without permission whilst in bondage’ rule whilst on holiday, you get one day in the chastity belt for every orgasm over the 21.”

She paused for a moment and then replied, “You’re on.”

We shifted into a 69 position and I was soon being pleasured by her talented mouth, whilst I set to work on her still locked up pussy and clit. By the time I had been brought to completion, Diane had three orgasms.

Day 2

We had previously worked out a rough plan for the three week summer holiday. Today was to be a day at the beach so both of us could get some colour before we went to see some of the less visited sights around the island.

After using the bathroom she was happy to find that I had laid out one of her more tightly fitting bikinis. I said, “Before you put on the bikini, I am going to make sure we are going have some more fun today.”

I had stand in front of me. I unlocked the padlock connecting her pussy lips, slipped in a couple of small eggs and relocked her lips together.

She put on the bikini bottom before saying “These eggs are moving about a little differently.”

“Yes, they are new ones Kathy has found. Instead of having weights inside, there is a magnet in each and they are designed to repel each other. So every movement will shift them in completely different ways.”

“Without meaning to be critical of you, that sounds really nasty for me.”

As I suspected, the bikini was tight enough around the crotch to show an outline of the padlock, as well as showing large expanse of her delightfully rounded bum. She then put on the top and the very thin cheesecloth shirt that only just covered her ass.

The sunbathing and swimming in the warm sea waters was most enjoyable and Diane was certainly red around the face at times, not from the sun, but from the teasing she got from the eggs that I had inserted earlier.

Diane wore these small eggs until we went to bed and was a horny mess, so I took pity on her, cuffed her wrists together before releasing her pussy from its bondage and removed the eggs. She begged me to do something to satisfy her, so I slowly entered her and in seconds she started to cum hard. I took my time giving her another three orgasms before I came hard inside her.

Day 3

Today we planned on visiting the Old Town in Rhodes, so I selected her tube style dress that showed off all her curves and figure to perfection. What she was not so happy about was the underwear I had selected. It was a waist chain that locked on, with two smaller chains that were attached to a small triangle of material that had nubs that would stimulate her clit. At the apex of the triangle that went through her crotch, between her ass cheeks there is another chain that I locked on to the waist belt.

The old town was crowded, and the walking around made the special thong created the desired effect. In one of the small back streets Diane leaned back against the wall of a house and pulled me in for a deep kiss before saying “I wish you could get inside me now and make me come hard.”

When we got back to the hotel Diane begged me to take there and then. I resisted the temptation. We showered together with her still wearing the thong. I deliberately patted the material that had her shivering with excitement. I did not, however, let her come.

After dinner I had her stand at the end of the bed, placed cuffs around her ankles, and secured them to the bed legs with her feet wide apart. I added wrist cuffs, had her bend over and tightly secured them to the head board. I then removed the chain from her crotch to waist, slipped in a vibrator with an additional clit stimulator before reattaching the chain to the waist. I turned the vibrator on.

I sat in the chair watching her as a series of powerful orgasms swept through her until she was a panting mess. After an hour I took pity on her. I removed her underwear, locked up her pussy again and then released her from the rest of her restraints. We laid down together. I no time, she fell asleep in my arms with the smile of a well satisfied woman.

More holiday fun next week.

Wicked Wednesday

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6 Responses to Summer Holiday

  1. Summer holidays are the best time for fun 🙂

    Rebel xox

  2. This was so hot. I love your stories. xx

  3. i have to say, every time i stop by it is just as sexy and intense as the last time!

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