Mistress has ordered a report to you about our just completed Caribbean cruise. It was a reward for five years of devoted service, and we had been fantasizing about it for a long time. She had me take along an assortment of leather cock straps, nipple clips, wrist and ankle shackles, and other toys for her to use.

The first morning on board, Mistress Diane had me wear a leather cock-and-ball strap that gave me a plump lump between my legs. My snow-white swim trunks clung to it; just thinking about how I looked gave me a hard-on that added to its size. She handed me a black T-shirt. Above the pocket was neatly stitched one word, “Trainee.” “You’ll wear this,” she ordered, “and if anyone is inquisitive, you will say, ’You’ll have to ask my Mistress,’ and nothing else.”

On deck, two or three couples were playing around the pool. We enjoyed ourselves in the water for a time, and then Mistress Diane ordered me to work suntan lotion into her back. Then I was told to take a chair away from her, but to stay watchful if she needed anything. Fifteen minutes later her finger beckoned, and I rushed to her side. “Massage my back again, then get in the pool so your trunks will be wet. Put on your T-shirt and return to your chair. Lay face-up so others can see your properly restrained sex organ.”

My cock struggled mightily against the wet trunks as I slipped on the shirt and again took up my wait. Mistress beckoned and made me fetch her a drink, again ordering me to get wet and return to my chair across the deck from her. Minutes later, an attractive dark-haired woman seated herself in the chair to my right; my cock pulsed and quivered. I was sure that she saw it as she made small talk. Finally, she said, “My curiosity is piqued by your shirt. Does it have a special meaning?” I looked across and saw that Mistress’s eyes were fixed on me. “You’ll have to ask my Mistress,” I replied and pointed in her direction. Mistress waved in return.

My new friend smiled and whispered in my ear, “If this is what I hope it is, I want to be your trainer.” She and Mistress chatted for about a half-hour, and when she returned I was advised that her name for the rest of the cruise was to be Mistress Mary, and I was to leave immediately to get the toys from our cabin and to appear on the main deck, cabin 102, at exactly noon. As I headed for the stairway, I caught a glimpse of my mistress and Mistress Mary together, laughing.

Twelve o’clock found me tapping on the cabin door. The lock turned and the door opened just a crack. I hesitated, but then stepped inside. The curtain inside the cabin door was pulled so that I could not see past it. Mistress Mary’s voice told me to lock the door, strip and blindfold myself, then to push the toys into the cabin. The toe of a black leather boot sensuously crept forward under the curtain. A black scarf was draped over it. I knelt and kissed the boot as I removed the scarf and shut off my sight with it.

Naked and blindfolded, I knelt and waited. “Oh, you have on a delightful cock strap,” she said. “Is it as tight as you can make it?” I confessed that it was adjustable and could be tightened. Fingers dug into my nipples as she commanded, “Then tighten it!”

I tugged at the leather straps, securing them at the last snap. I was by now reeling in erotic delight, my cock throbbing, my balls aching. In the next instant I was over the edge and knew I could not stop my orgasm. “Oh, Mistress,” I moaned as the hot juice ejaculated in spurt after spurt after spurt.

Mistress Mary was furious that I had failed to control myself, and now tit clips dug into my tender nipples and a dildo pushed its way into my unlubricated rectum. My hands were secured behind my back and my ankles attached by a rope to my wrists. “Slave, before this week is over you will regret that you shot that load of come. Your Mistress explained that you had limited mastery over your sex organ, and that you and it needed training. I left my husband in the cabin while I went to the pool. He’s now in your cabin entertaining your Mistress. You are completely mine all of this afternoon.”

A whip flicked at the nipple clips until they gave up their hold. My balls were coated with heat-producing liniment. My ass was fucked with the bumpy dildo until I thought I would collapse. I did not come; Mistress Mary warned me of unspeakable discipline if I erred. She released me and ordered that I return to my Mistress, but she would see me at dinner.

At the restaurant I met Mary’s husband. A tall, good-looking man who always kept his eyes on the floor when Mary was near, he looked like he might make a great slave. He was now introduced as “slave Joe.” Later, Joe and I spent the night bound to the foot of the bed while our Mistresses frolicked together. They engaged in sixty-nine cunt-lapping and made a bet on who would orgasm first. Mary won by making Diane climb over the peak. Mary claimed her prize, turning me over her knee for a sound spanking.

My Mistress won only once the entire week. I’m still not sure if it was a concocted tournament so I would be on the receiving end of Mary’s paddle.

The cruise ended Sunday, but not before Diane and Mary arranged for a monthly meeting at a motel halfway between our homes (we live 1,000 miles apart). Diane has already told me that I’m to begin searching for employment in the same city where Mary and Joe live. She’s also told me that she has arranged for me to spend a week being trained by Mary. I’m to be taken from the motel naked and bound on the floor of their car.

Take a cruise and see the world? I was taken on a cruise and saw stars nightly. It was delightful, and I’m enthusiastically looking forward to our monthly trysts. Mistress Diane says it’ll be a cruise every year from now on. And by the next one I know I’ll be a better trained slave.