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Cuckold from Day One - Part 4

Emily


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Hello,

Please read Part 1 here

Emily

A couple of months into Jerry's six months of chastity punishment, we left on a three-week cruise around Europe that we had planned long before. This would be my first trip out of the country and was an opportunity for me to show off a little. It seemed like I had been strapping my boobs down my whole life to try and minimize and hide them to keep people from getting a peek at them or my cleavage. I decided that I was going to let my hair down while in Europe and dress much more revealingly than I ever had at home. I had also set a goal to get laid a few times on the cruise.

Jerry was in charge of packing for both of us. I would tell him what I wanted, and he would find it and pack for me. I had Jerry go to Costco to get some condoms and he came back with a Trojan Pleasure Pack with 40 condoms, which he packed in his case. I took him shopping with me to pick out a few revealing bikinis. We also bought several scandalous evening dresses and other outfits that showed off my boobs and body more than covered them up. I had never worn anything like these before. While I did have him pack a couple of bras for the trip, mostly for during travel, I didn't include any other underwear. When Jerry specifically asked if he should put some panties in the luggage, I told him that I didn't plan on wearing any panties during our trip. I also told him not to pack any underwear, as I didn't want him wearing any if I wasn't.

I could see Jerry getting nervous as we approached the TSA security station. I told him not to worry as the metal cage would probably not even register. (I giggled a little inside at telling him this.) I went through first and waited by the female TSA agent as he went through. I saw the shock on his face when the machine buzzed loudly, and the agent told him to stand still so she could scan him. I whispered to her that it was a chastity device that set off the alarm. She looked at me quizzically when I said this and waived her metal detector at his crotch, which immediately went off. She explained that a further investigation was required and led us into a small room where we were joined by a male agent. When Jerry dropped his pants, they were both a little surprised that there was no underwear, just a shiny metal cage enveloping his cock. The male agent said there was no terrorist threat here and left, the female agent stayed. She asked me why I hadn't used a plastic device that would go through security. I just smiled at her and said, "Well, where would the fun be in doing that?" We both had a laugh at that.

After a closer inspection of the device, she sent us on our way saying that she should get something like this for her boyfriend. Jerry was embarrassed to show his chastity cage in public, but I was proud of him and wanted to show him off. I knew this was only the first time on this trip he would be subjected to this. We encountered many metal detectors during the trip, at airports, cruise terminals, the cruise ship, etc. Every time the device would set it off and he would get further inspection. I basked in the praise I got from both male and female inspectors. I was burning up with horniness from showing him off and as soon as we arrived, I had Jerry eat my pussy for about an hour.

We had splurged on a luxury suite on the ship. The benefits of booking the suite was that we had access to a private pool and spa area and a private dining area that were only available to other suite passengers. We didn't need to mingle with the regular passengers unless we ventured out into the public areas of the ship. We were also assigned a butler to make sure we always had whatever we wanted. I was happy to see that our butler was a tall, young, bald, handsome man from Jamaica. He had a wonderful accent, and I was attracted to him immediately. He introduced himself as Donovan and said he was there to personally wait on us and make our vacation perfect. He opened our luggage and started organizing and hanging up our clothes.

It only took him a few seconds to put Jerry's clothes away, as there were only four outfits and no underwear. I even had Jerry strip, so he could put his travel clothes in the ship laundry. Donovan didn't say anything at seeing Jerry's cage but glanced at me with a wry smile. As he hung up my dresses, all of which had dramatic slits up the sides or plunging necklines down to my waist, he kept glancing back at me. He held up the skimpy bikinis and whistled before putting them in the drawer. He finally found my two bras and asked where the rest of my underwear was. When I informed him that I hadn't brought any for either of us, he whistled again and smiled broadly at me with a mouthful of gleaming white teeth.

When Donovan told us there was an introductory afternoon tea for the suite passengers to get to know each other, I asked him what I should wear to that. He went through my dresses again and finally brought out my red dress that fell to my ankles with only straps holding the front and back together. I went in the other room and put it on. As I walked back out, he nodded to me in appreciation. My boobs were swaying back and forth as I walked and a quick glance at the side slit made it apparent that I wasn't wearing anything else. He told me I would be the hit of the party as he started to adjust the straps so it would fit me better. As he adjusted the straps in front, his hands brushed against my saggy boobs causing my nipples to harden. He smiled, gave me a quick peck on the lips and said, "That's better. Go get ‘em." We were the best dressed couple at the tea. It looked like some couples had not even changed clothes after flying for many hours to get there. As Donavan had predicted, I was the hit of the party and everyone wanted to talk to us. I caught all of them staring at my tits at one point. It was exhilarating and I had never felt so sexy in my life. We met the other 15 couples that were allowed in the suite dining room and pool area. The women all promised they would dress more appropriately for dinner that night. I explained that it was my first time in Europe, and I planned on dressing more revealingly that I was used to because I felt free there. One of the couples we met were Ed and Kiko. I recognized him as the billionaire founder of a well-known tech company. He was about 40, tall, handsome and muscular. Kiko was in her late 20s and from Japanese descent. She was very pretty and petite with beautiful long black hair. I remember reading in the society magazines that he had married her after divorcing his first wife. Kiko had worked as the public relations manager of his company but quit her job after the wedding. They were both very friendly and invited us to sit with them. Ed sat by me and Kiko sat by Jerry. We soon found out that our suites were on the same floor, just opposite sides of the ship, only a few feet away. At the end of the tea we walked together back to our cabins. Ed with me, holding my hand, and Kiko with Jerry, her arm looped in his. We arranged to meet at dinner then went to our separate cabins. I was as horny as I'd ever been in my life.

The first thing I did was call Donovan to our suite. I told him how exciting it had been to be the center of attention and to have both men and women staring at my tits, then I asked him to help me out of the dress. He first dropped to his knees and helped me take of the high heels that were killing me. Then he stood and pulled the dress over my head, leaving me completely naked. As he took the dress to hang it up, I just stood there naked. Jerry had also removed his clothes and had retreated to a chair he pulled into the corner. Donovan returned and came up behind me. I first felt his hands rubbing me on the back and ass. Then as his hands moved around to massage and fondle my breasts, I felt his hard cock poke me in the back. He had taken his clothes off too.

I stood there in the middle of the room while Donovan ran his huge hands over my body and kissed my neck. I turned to him and realized just how big of a man he was. I only came up to his shoulders, which were broad and powerful. I ran my hands over his muscled chest and hard nipples. My hands went to his cock, which was hard as a rock, and nice and long. His skin was smooth, hairless and a rich chocolate brown. I felt his hands on my shoulders pushing me to my knees. He was taking control of the situation and I gave in to his desires. I slowly licked his cock up and down the shaft and popped the mushroom head into my mouth. I moved back and forth pushing him deeper each time until he was all the way in and down my throat. He was moaning loudly and starting to thrust his hips back and forth, fucking my throat. I pulled off him and told Jerry to bring one of the condoms over and put it on Donovan. While he was struggling to get it on, I stood back up and started kissing Donovan passionately.

When Jerry finally had the condom in place, he returned to his chair. Donovan picked me up completely, even though I am not a petite woman, had me wrap my legs around his waist, lined me up and impaled me on his cock in one, quick motion. I had not had sex in about a week, which is a long time for me, and the insertion resulted in an orgasm right away. He smiled as I convulsed around his cock, then started lifting me up and down on his cock. I had never been fucked like this before. My arms and legs were wrapped around him, my boobs were smashed against his chest, and we kissed as he fucked me hard and deep. When his arms started to get tired, he pushed me up against the wall to help hold me up and thrust into me hard and fast. Soon I heard him moan and felt him pulse inside me as he filled the condom with cum. He finally pulled out and lowered me to the floor. I wobbled on my legs after several orgasms from his fucking. I called Jerry over and had him remove the used condom and clean Donovan's cock with a warm wash rag. Donovan and I laid on the bed and kissed while he recovered. When he was hard again, Jerry put a new condom on his cock, and I got on top of him and took control this time as I rode him to orgasm. After Jerry had once again removed the condom and cleaned him up, Donovan got dressed and said he had to get back to work. I asked him to return later and help me dress for the evening meal.

I picked out a black corset that emphasized my waist and pushed my tits up, and blue leggings that hugged and showed off my legs and ass. When Donovan showed up, he gave one of his whistles at my outfit and smiled broadly. I asked him to pick out a dress to go with this outfit. He looked at me closely, reviewed my dresses and finally told me that I should go just like that. I objected that it looked like I was in my underwear, but he said that an outfit like this is common in the nightclubs on the ship and that I would be accepted at dinner and would be a big hit. He said there was only one issue, that the corset needed to be tighter. He came up behind me, loosened the knots Jerry had tied and pulled the laces much tighter. As he did, I felt my waist pulled in and my saggy tits pushed up. It started to get a little hard to breath. I gave Jerry a look of disgust that he had done such a poor job of putting my corset on.

I looked in the mirror and liked what I saw. I could actually see my waist and my tits were pushed up mostly above the corset, just sitting on top and jiggling with every move I made. Donovan looked me over, put my high heels on, then noticed that one nipple was showing. He put his big finger on my nipple and pushed it down under the edge of the corset. When he touched my nipple, a bolt of electricity went straight from there to my pussy. I pulled him in for a passionate kiss and told him, loud enough for Jerry to hear, that I needed him to come by later and help me out of my outfit. He agreed enthusiastically.

I was a big hit at dinner. Ed and Kiko stopped by to walk with us to the dining room. They were both initially shocked at my outfit but insisted that I looked great and should not put anything else on. With my jiggling tits on full display I got a lot of attention from everyone in the dining room and I caught everyone staring at them during dinner. I had Jerry check occasionally to make sure my nipple was not showing, but it never popped out again.

We sat with Ed and Kiko again at dinner. Kiko and I went to the restroom together and while we were alone, she confessed that Ed was totally infatuated with me. She told me they were experienced swingers and often had other women or couples join them for sex. She also told me Ed had fucked her unusually hard that afternoon after seeing me at the tea. I told her that I thought Ed was very handsome and that she was the most beautiful woman on the ship. She shyly lowered her eyes, but I took her face in my hands and kissed her hard with my tongue exploring her mouth. She was wearing a dress with a neckline that plunged all the way to her belly button and I slipped my hand inside her dress and squeezed her small, firm breast and pinched her nipple so that it hardened under my grip. I felt her gasp a little as I kissed her. As we left, I told her that I would consider their offer, but that Jerry would not be much use, other than to lick pussy or suck cock, because he was in a chastity device. She smiled and said she had heard of that but never seen it in person and was looking forward to checking it out. After they walked with us back to our cabins, they invited us in for some after dinner drinks. I told them that I would love that at another time, but that I needed to get back to our cabin and get some sleep. With that I gave a little wink to Kiko, knowing that she was about to get fucked hard again.

Donovan was waiting for us naked in our cabin. He immediately dropped to his knees, removed my heels and slipped my leggings off, but left the corset on. He pulled on the tops of my tits until they popped completely out the top of the corset so that he could fondle them as he fucked me. Jerry was on the ball and slipped a condom on that big black cock as Donovan pulled me outside onto the veranda. He bent me over the railing, slapped my ass playfully, reached under and massaged my hanging tits, then slid balls-deep into me in one smooth thrust. I let out a little scream, then settled in as he began fucking me hard. No one could see onto our veranda, but if Ed and Kiko were out on theirs, they surely would be able to hear us moan and scream in ecstasy. I later found out they were out there, heard us and Kiko received a royal fucking in response. Donovan fucked me twice that night after dinner. I think he liked the corset. I began to realize that at this rate, the 40 condoms would not last even half of the cruise.

Donovan came early the next morning to fuck me before breakfast and again after we had visited the pool. Each time Jerry was dutiful in providing condom service before and after each encounter. At the pool I wore one of my skimpiest bikinis. It barely covered my nipples on the top with tiny triangles for each breast. On the bottom, the back was a thong and in the front was another triangle that covered only my pussy lips. My body was essentially on display. I started wondering what the point was of wearing anything at all.

We asked Donovan about the nightclubs on the ship he had referred to and he explained that one of the bars, late at night, was open for dancing and drinking and the dress code allowed for some risqué outfits. I pulled out perhaps my most revealing outfit and asked if I could wear it to the nightclub. At first blush, it looked just like some scraps of material. The top was made up of a long strip of thin material that went from one hip, over the left breast, around my neck, crossed at the neck and down to the other hip, holding the right breast. This left my entire back uncovered as well as a large triangle uncovered in the front from my chest to my belly button. Because the material was tight on me it helped slow the bouncing of my boobs up and down but facilitated their swaying back and forth. There was a matching strip of thin material, almost see-through, that went through my legs and partially covered my front and ass. Down my legs were two small strips on each leg, like a genie outfit, that met at my ankles but left the legs mostly uncovered. It only took a quick glance to realize I had nothing else on, other than these flimsy strips of material.

Donovan approved of the outfit and let us know that he had covered for a fellow employee at the nightclub the night before and that the attendees included a group of college-aged men. I had the goal of meeting some of these young men. We also let Ed and Kiko know we were going dancing at the club and they said they might come by to see us.

We had experienced an eventful beginning to our cruise, and things were just getting started. In the next part of the story we will talk about the other adventures we had on the ship with our fellow suite passengers and with Ed and Kiko in particular.

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