Summer Holiday

"Would you like to come on holiday with me?" I was asked one day at work by Susannah. Susannah is a colleague of mine who I have always been friends with but nothing more. She is tall, slim and looks a lot younger than her actual age. She has large surgically enhanced breasts which she often displays with low cut tops. She always dresses to emphasise her figure and wears quite severe and some would consider dominatrix style clothing. She will wear short skirts and high heeled shoes or boots. She also has long black hair and generally wears thick rimmed glasses. She comes across as a little scary but I have always found this quite appealing.

"What do you have in mind?" I asked in reply. She told me she'd found an all-inclusive resort in Spain she'd like to visit. She judged that we were good friends and from recent conversations she guessed I was at a loose end with regards to holidays. We were alone when she spoke to me and came closer to me, invading my personal space and her hand reached down to squeeze me through my trousers. As she squeezed my manhood she said in hushed tones, "and I think you'll enjoy what I can offer."

We agreed to go and Susannah made all the arrangements. She suggested I come over to hers the night before we left and I stay with her as we had an early start. When I arrived she made me unpack my suitcase and went through my clothes discarding nearly everything. When she'd finished, she led me upstairs and pointed to the stuff she wanted me to bring. One comprised a pile of BDSM gear including whips, floggers, restraints, dildo gag and the like. Another comprised a series of women's dressing up outfits including Alice in Wonderland, French Maid and Schoolgirl. "You will be carrying this stuff in your suitcase because if you're stopped you will have to explain it to the authorities." I look a little horrified and she went on to say," these are all your outfits for the week," pointing to the sissy style clothing. She then lead me over to show me what she was packing and it comprised a series of dominatrix/fetish style clothing of latex and leather outfits but some seriously sexy footwear. I was extremely horrified and excited at the same time.

When it came to bedtime, Susannah asked me to join her in her bed. She told me to remove all my clothes as she slept naked and wanted me to do the same so that we could get to know each other better. She had an admiring smile as I removed my pants and I guessed I was going to have some fun with her. After I climbed into bed, she came closer and her hand moved down to my now erect penis. She started to wank me and told me to enjoy the experience. I soon climaxed into some tissues she had to hand. As I relaxed, I could feel her fumbling around and touching my penis again. Soon I felt something cold touching it and then an audible snap. "What are you doing?" I asked. She removed the covers enough to let me see that my penis had been enclosed in a chastity device preventing me from getting an erection. Worse still, it had shiny metal padlock securing it in place. "You're mine now," she whispered, "and you'll do as you're told for the rest of the week." The fear of her words and actions excited me and I knew very little about what was to come.

The following day we travelled to the airport and I endured a humiliating scene when we travelled through security. The padlock securing the chastity device set off the metal detectors and eventually I had to go inside a room where I had to show a guard the offending item. As I walked away, I could hear sniggers from the guard and his colleagues, the humiliation had begun. Afterwards, Susannah told me she'd deliberately used a metal padlock as opposed to a plastic one as she knew this would happen. She also said that this would be a mild embarrassment compared to what was to come.

The remainder of the journey was uneventful. Customs officials in Spain looked totally disinterested in our arrival and so I had no embarrassing incident explaining the contents of my suitcase to anyone. The resort looked like any other and as we checked in and were shown to our room, nothing looked different. The room had a large bed and I was looking forward to sharing it with Susannah. She saw me staring at it and then giggled. "You won't be sleeping in there with me," she stated. At this point, she moved to the base of the bed and pulled a sheet off an item I hadn't seen. She revealed a cage and indicated that this is where I'd be sleeping.

When dinnertime came, Susannah made me wear the Alice in Wonderland outfit and dressed me up as a woman complete with wig and underwear. I enjoyed the feeling of the satin knickers and couldn't resist pressing the fabric against my bottom. Susannah wore a lace body stocking which emphasised her breasts and slim figure. She made me help her dress and then I had to lick her shoes clean before we went downstairs. She got a lot of attention, especially from men. A few came up to chat and they were quite open about what they'd like to do later. After dinner, there was an erotic dancing show and when that finished we went for a tour of the resort. There was a smaller function room which served as a dungeon. Various items of BDSM equipment were in this room surrounded by chairs so that people could watch play sessions taking place.

The following morning we lounged by the pool, well when I say lounged, Susannah stripped naked and lay down to sun herself and darken her already brown skin whilst I was forced to sit in humiliation in the maids outfit she'd brought for me. I sizzled in the back satin, petticoats, stocking and nylon wig I was forced to wear. I was there to serve Susannah, rubbing in suntan lotion and fetching drinks from the bar as required. When I failed to please, she would slap my face. I wasn't alone as there were plenty of other subs serving their Dommes, men and women like myself were forced to serve their masters or mistresses like me. Some were being treated far worse as they were forced to act as human stools or were being humiliated in more severe ways.

Frequently men and women would come over to chat. Often they would also be naked and I must say that I was roused by seeing beautiful naked people standing over us while they casually chatted with Susannah and exchanged interests and fantasies. In the afternoon, Susannah disappeared off with two of the men and reappeared an hour later looking very flushed. Her pussy was red and swollen where she must have been penetrated by them.

That evening she asked me to stay with the fun she had planned. Two men and another woman came to our room. I was dressed as a maid and had to serve in this role. Soon the foursome got down to sex while I had to watch from the shadows. My cock wanted to harden but was frustratingly restrained by the plastic chastity cage. The women began by sucking the men's cocks. After they came one moved towards me and asked me to open my mouth. She then snowballed the cum she was savouring from her mouth into mine. When they were done, Susannah beckoned me over and pointed at her cum filled pussy. "Eat," was the only word she beckoned. I knelt down and put my tongue inside her pussy. It was full of the combined wad of her own juices mixed with the two men's thick semen. I hungrily licked her out and swallowed the liquid. I was really enjoying it, probably too much when she pushed me away. The other woman had a bottom full of cum and she made me rim her bumhole while she cream pied the juices out of her.

The rest of the week was a blur. I was allowed to remove the chastity device to wash, but only under the watchful eye of Susannah who would lock it back into place as soon as possible. I became extremely frustrated over the week as nudity was common and there were some very beautiful women staying in the resort who tantalised me after Susannah had spoken to them. One evening we used the BDSM facilities and I was tied to a whipping bench dressed as a bad schoolgirl and given a severe caning on my bottom, thighs and shoulders which just made me want to seek release further. On another occasion Susannah took a woman to bed with her and they savoured each other whilst I lay frustratingly in the cage at the bottom of the bed unable to sleep due to the noise being made by the two girls. However it is the last night which was most memorable.

On the morning of the last full day, Susannah asked me to find three or four men who were willing to fuck her. This seemed like a normal request but then she said she wanted to be blindfolded and tied to the bed and she didn't want to know their identities. The request seemed a little harder but achievable. I spent the day avoiding Susannah and speaking to men asking them if they wanted to play. By lunchtime I had my volunteers, including a couple spares in case of any no-shows. That evening, I prepared Susannah. I helped her undress and tied her to the bed. Before I put on the blindfold I asked her is this is what she wanted and she said yes. When she was ready, I went to the room door and let three men in. They each took it in turn to slip their tool inside her waiting pussy and fuck her until they released their cum. No one was allowed to speak except Susannah who was loving the whole experience. Finally, the last man finished and they all left. I removed Susannah's blindfold and untied her. Her pussy was swollen red and cum was leaking out of her. I suspected I'd be asked to clean her again but instead she skipped over to her handbag and dangled a key in front of me. "Now it's time for your fun," she said with a twinkle in her eye.

She made me remove my girly panties and removed the chastity device. I immediately developed an erection and when I touched my hardening cock I immediately came. Despite my embarrassment, Susannah told me to remove my girlie clothing and join her on the bed. She touched my cock and made it hard again before whispering in my ear, "now it's your turn," and pointed to her pussy. I've always loved sloppy seconds and so there was no hesitation in me positioning myself over her and sliding my member in. I struggled to keep inside the slick walls of her cum soaked quim but I didn't have to wait long before I came again adding my own juices to the ones already inside her. She burst into tears then and I held her whilst she cried and soon we both fell asleep and lay in each other's arms until morning.

The following day the holiday was over and we flew home. Susannah asked me into her flat but I declined and went home relishing a bit of my own company. When I got back my phone bleeped. I looked at it and found a number of photos attached of me in the various costumes I'd worn over the past week. Under the photos was a message. If you don't want these to be made public, you'll join me next year too.