I needed to get out there and start dating again after my wife died. So I went on a single’s cruise. It really changed my life.
Fbailey story number 241
My wife had been dead for long enough according to my children and friends. So I booked a week on a single’s cruise in the Caribbean for people over fifty. Then when I called back to make it two weeks, the lady talked me into a full four weeks. That way I would get to meet four different sets of women who usually come aboard for a week at a time and I would get upgraded to a suite that would be up much higher in the ship. Okay, why not! So I changed my vacation to include all four weeks.
Everyone was very supportive of me going on that vacation cruise. People started giving me gifts. Some women gave me underwear that they would like to see me in. My daughter gave me a few pair of swimming trunks that she thought would excite the ladies. Friends gave me sun block, sunglasses, and plenty of condoms. Of course everyone also had an opinion on what to say to get a woman in bed with me.
Surprisingly the best ideas were from a lady that I had dated a few times. She simply told me to be myself, to talk to a lot of different ladies, and not to be afraid to ask them back to my room. After all those other women would be there to meet a man and they would expect to be invited to man’s room quickly. They also would expect to have sex with me. After all it was a seven day six night single’s cruise and there would not be a lot of time to wine, dine, and seduce a partner. She also told me to expect the other women to lie to me. After all they would do anything to catch a fine man like me. Then she kissed me and rolled over for the night. She didn’t want me going off so excited that I would cum too quickly with the first woman that I got in bed. I made love to her in the morning too before she took me to the airport to catch my flight.
Getting through the security check at the airport was not all that bad. I arrived a few hours early and found myself waiting for my flight. Another passenger Emma was there with me. I just listened as Emma told me all about a Single’s Cruise that she was going on. I listened and then I told her that I was going on the same cruise but for four weeks. She was going for just the one week. So for the next hour or so all we did was to talk about what we expected on our cruise. Emma confirmed what my companion the night before had said about expecting to have sex with at least a dozen men in the next week. She said that she wouldn’t mind starting with me and then asked me if I wanted to join the mile high club with her on our flight. I told Emma that I would love to join with her. That made her smile.
We checked with the person at the gate and found that I had an empty seat next to mine so Emma changed her seat assignment. When we boarded the plane Emma boldly told the flight attendant that we wanted to join the mile high club and then asked her to let us know when the best time was. She smiled and said that she would let us know.
Sure enough not too long after the seatbelt sign went off the flight attendant gave us the signal to go toward the rear of the plane. She followed us down the aisle and opened the restroom door. She told us to lock it from the inside and to take our time. Emma asked her if she would stick around a minute and take a picture for her scrapbook. The attendant smiled and took the camera from her.
Inside the tiny restroom Emma told me to drop my pants while she got ready. She lifted her skirt up above her waist, lowered her panties to her knees, and completely unbuttoned her blouse. Then she had me stick my cock into her from behind, lifted her bra above her tits, and placed my hands on them. Next she opened up the restroom door and smiled at the attendant. The door stayed open while Emma checked the picture on the small screen and asked the attendant to step back and get one more of us. The attendant was very gracious and took a second picture before handing Emma the camera and closing the door for us. Emma then told me to take all the time I wanted. She was really going to enjoy the trip of a lifetime. I was pretty excited as Emma had expected and all too soon I was thrusting and cumming in her. We danced around so that she could sit on the toilet to pee and clean herself up. I offered to leave but she insisted that I stay with her. While she sat there she sucked my cock clean.
For a high school librarian she was certainly out to sow her wild oats. She had been planning that trip for years. She was throwing caution to the wind. She was going to experience everything that she had never had a chance to experience before. She was proud to become a member of the mile high club.
For the rest of the flight Emma talked about how straight-laced her husband had been and how she had never been able to just cut loose before. Then of course being a schoolteacher and a librarian to boot she had a reputation to uphold. She told me that she was a Mr. Hyde and a Doctor Jeckle just waiting to come out. She also told me that the restroom was just one of her many desires, fantasies, and plans for the trip. Emma made me smile when she asked me if I had ever made love while standing up in a hammock. No I hadn’t and neither had she but that wouldn’t stop her from trying it if she were asked.
As we exited the plane our flight attendant handed us each a plastic set of the airline ‘mile high wings’ as a momento. They even had MHC on them. Emma proudly pinned her wings to her blouse right over her left breast. That got a big smile out the man at the exit. We had no luggage to bother with because it was already tagged to go to our ship. We went to the man holding up a sign with the ship’s name on it and found that two of the other passengers were standing with him already. So the three ladies and I got in the shuttle bus and were whisked away. As we rode along the bus driver told us about our ship, the number of things to do, and then he finished off by telling us that there were approximately nine women to every man on the passenger list. Wow! Emma held my arm tighter.
I could not believe that there would be nine women for every man and that they all expected to have sex on board the ship before it docked in a week. I just hoped that the other men would do their part.
Just as we could see the ship Emma told the other two women that she would be happy to share me if they wanted to join us in a threesome. One of the women frowned but the other one smiled ear to ear.
As we checked in with the Purser he looked at our tickets, our identification, and then he pointed us toward our cabins. Emma and the other two women were sent down three decks while I was sent up three decks.
Emma held hands with the woman that smiled about a threesome and together they accompanied me to my cabin. It was quite easy to find and it was very spacious. I had a sitting room with a separate bedroom, along with a very nice size bathroom too. My luggage was already in my room. A bath towel had been folded into a seal and placed on my bed. There was even a mint on my pillow.
Not one to waist time Emma asked me if I was up a threesome right then. Marge, the other woman, said that she needed to get cleaned up first. Emma suggested that we should all see if we could fit in the shower together. Surprisingly Marge went along with the idea. Okay!
So Emma started to get undressed. Marge was a little shy at first but then decided that she should get undressed too. I was the first one done and I folded my clothes and placed them neatly on the couch. Emma was quite a woman. She had signs of age of course but she also looked like a woman that took very good care of her body too. Obviously she died her hair a dark brown because her pussy had a nice reddish color to it. She had a slight belly and very nice breasts. Marge was about the same build but much softer. Her belly was rounder and flabby so was her ass but her breasts were smaller and they sagged too. They both seemed to like my body and my hard cock. Emma handed me her camera and asked me to take a picture of her with Marge. I smiled as Emma hugged Marge to her and both women were nude with one of their breasts smashed into the other woman’s breast. Then Emma set the camera on a stand and the three of us got in the same picture. I was in the middle with my arms around both women and holding onto a tit.
The shower was fun especially when Emma told me to wash out both of their pussies real well for oral sex. I sure enjoyed shoving my fingers up into two pussies like that. Of course I thought that I would be the one performing oral sex on them but apparently Emma had something different in mind. Emma very cleverly made it seem as if it were my idea when she asked me if I wanted to see the two of them make out together. By then I had enough experience with Emma to just go along with her idea and tell her that I would love to watch the two of them make out. Then I even encouraged her to stick her tongue as far into Marge’s pussy as she could get it. I encouraged Marge to do the same to Emma too. It was better than any X-rated movie that I had ever seen. Oh they weren’t the prettiest or sexiest women that I had seen like that but they were real and I was right there with them. When Emma was on top I would slip my cock into her pussy while Marge watched from just inches away and then into Marge when she was on top. I didn’t really care who I cum in but Emma did, so I filled Marge’s pussy so that Emma could lick it out. Of course I took a few pictures of the girls together for Emma’s scrapbook.
When the girls were done we got cleaned up again and got dressed. Then I escorted the two ladies down to their cabins. They were not too far away from one another. Marge went into her cabin and I went in with Emma while she changed her clothes. I smiled as she got undressed again and asked me if I wanted anymore sex before we went up to look for food. I had actually had enough sex for a while so I just watched Emma get dressed. She did not put on a bra or any panties she just slipped on a short dress and off we went.
We found a very nice seafood buffet and got in line. Emma looked around the room and asked me if I liked anyone in particular. I saw lots of good-looking women. That wasn’t what Emma had in mind. She was asking me to pick out a woman that I wanted to have sex with next and then she would help me get her. Okay!
So then I looked around the room for a woman that was way too good for me. I set my sights on what could have been a fashion model or a movie star. She was very elegant looking and quite beautiful. So I pointed her out to Emma. Even she was impressed with my choice. We ate dinner and then she split off to seduce my choice.
Meanwhile I too went shopping for another woman to take to bed. I decided to start out around the pool area since they would be exposing most of their body to my gaze and I could check out the merchandise beforehand. I was not alone either there were several other men looking over the prospects too. A couple of the women really stood out and I do mean their tits were huge. One was just pretty with what could only be described as the smallest bikini that I had ever seen on a woman before. I figured that I had absolutely nothing to loose so I just walked up to the first women and asked her if she would like to get better acquainted in my stateroom. I was glad when she shot me down so that I could walk over the other woman that had really excited me and asked her the same question. She accepted my offer. When I looked over at the first woman she just looked away in disgust.
As I escorted the lady of my choice up to my stateroom Trish asked me why I hadn’t asked her first. I whole heartily apologized and simply said that the other woman had just been on the way to the one that I really wanted and that I foolishly asked her on my way to Trish. I told her that I shouldn’t have asked her and that I was glad that she hadn’t accepted my offer. She liked my answer and then she said that she too was glad that the other lady had turned me down. I really couldn’t believe how easy picking women up was. It was like shooting fish in a barrel.
Trish liked my cabin and said that it was a lot better than the one that she shared with a friend. Then she asked me if I really wanted to talk or just get to the sex part right away. What! Apparently that was not her first cruise. I asked her if we could at least get undressed and get in bed before we talked. Trish smiled and asked me if I just wanted to see her naked. Yes! Honesty was the best policy, because she said okay and reached behind herself to untie her tiny top and remove it. Then she untied the bow on her hip and let her bottom drop to the floor. Trish then told me that she felt most comfortable in a 40-DDD bra and that her breasts were completely natural. I really enjoyed playing with her big breasts and her puffy pussy while Trish told me all about her ex-husband, her boring job, and about her six grandchildren. When I had heard enough about her past I asked Trish if she was into a threesome with another woman. She smiled and said that she had done that a few times in the past. So I called down to Emma’s cabin and invited her up for a threesome.
Emma must have ran because not a minute later there was a knock on the door and I opened it up to find Emma standing there in her bikini. She really looked good and I knew that I could fall in love with her. The best part was that she lived in the same city that I lived in.
I introduced the two ladies to one another, helped Emma out of her bikini, and then I got between Trish’s legs. She opened her legs up wide for me, reached down between her legs, and then she opened up her pussy lips for me too so that I could slip my tongue right in. Emma got in there too next to me so I offered her a taste. Then together Emma and I went after those enormous tits. Trish seemed to really enjoy all of the attention. Emma and I also used our fingers to stimulate Trish’s clit to give her an orgasm. Since Emma had rushed right up I took a few pictures for her scrapbook on my camera. I got her eating Trish’s pussy, them in a sixty-nine together, and then with Trish eating Emma out. I fucked Trish hard and steady until we both cum together. It had been a very long day. We all fell asleep in my bed and then awoke early in the morning to start in again. Trish sure could suck cock and apparently she was very good at eating pussy too according to Emma.
So my very first day included sex with Emma on the airplane, a threesome with her and Marge in the afternoon, and another threesome with her and Trish after dinner.
Then the second day started out with another threesome with her and Trish. Well to be fair it really wasn’t a threesome because the two women hardly needed me at all. I played with my camera, watched the fun, and then I fucked Trish when I couldn’t stand it another second. The two women went right back to what they were doing while I watched.
After a late breakfast Emma introduced me to Sylvia the sophisticated woman that I had picked out the evening before. Emma told me that Sylvia was not into threesomes and certainly not with another woman. However she was perfectly willing to let me fuck her while I got to know her. It seems that she liked the way I looked. It didn’t hurt any that Emma had lied to her about me owing a big company back home.
Sylvia really was quite sophisticated. She talked about going to Broadway plays, going to the Opera, and meeting celebrities. She ate in fine restaurants, went to Europe often, and had money that her dead husband had left her. In fact she was only on that ship to let loose, get fucked, and blow off steam where her friends wouldn’t see her. She also made it perfectly clear that she wasn’t about to whore herself out to every man onboard either. I felt both honored and insulted at the same time. Fucking Sylvia was sort of like what I would expect from fucking a corpse. She just laid there silently and let me fuck her without any emotion or even an orgasm. After I cum she told me that she had never in her life had an orgasm and that she didn’t know what all the fuss was about. She was a cold fish. After she used the toilet and took a shower she walked out to find me holding my camera and clicking away. That really pissed her off but she couldn’t very well walk out of my stateroom naked. So I took shot after shot of her as she tried to cover herself and get dressed at the same time. Just as Sylvia was about to leave she threatened to sick her lawyers on me to get the pictures back. I told her that if she did they would be all over the Internet. That stopped her dead in her tracks. Then I told her that if she wanted to keep them off the Internet that she was to come back to my cabin that evening at seven o’clock. She agreed.
That day Emma and I arranged a ‘cumming out party’ for Sylvia. We invited Marge and Trish to be in my room when Sylvia arrived and for six men to show up afterwards for a gangbang. That stuck up bitch would orgasm one way or another. To ease my tension I made love to Emma after lunch and then we took a short nap together.
Sylvia knocked on my door at precisely seven o’clock and I let her in. The other three women were sitting on my couch. Everyone was dressed and Sylvia was to get undressed first. She tried to squirm her way out of it but she eventually gave in and started to undress to cheers from the three women. Then one at a time the three women undressed too. Trish’s big knockers sure drew attention.
My three women did everything to Sylvia that they had done to one another and then some. They never gave her clit or pussy a break much less her breasts. Each woman covered Sylvia’s mouth with her pussy too until they were somewhat happy with the results. At nine o’clock she still had not experienced an orgasm however the six other men arrived. Sylvia got scared but the other women held her down as the fist man fucked her. They held her less for the second man and by the third man they had let go of Sylvia. I wished that I had gotten to fuck her while she was squirming because she went back to the cold fish method. Emma told Sylvia to get on top and fuck the forth man. She needed instruction and practice but she did it. She rode the fifth and sixth man figuring that she was done but I hadn’t had a turn yet. So Sylvia climbed on my cock and put her tits in my face. As she fucked up and down on my pole I bit and chewed on her nipples making them super sensitive. Just as she made me cum she had her very first orgasm. She thrashed about like it was the best experience of her lifetime and I truly think that it might have been. She howled too and then she slumped off to the side.
Of course that triggered six more erections so the men started right back in on her. Sylvia responded to their needs that time and actually moved under them. She didn’t have an orgasm every time but she did have two more with them. I gave her an orgasm and then we started all over again. That night lasted forever and all seven of us fucked Sylvia at least three times each with the help of the other three women getting us hard for her. They sucked our cocks hard for her.
In the morning I saw Emma and Sylvia in the shower having fun. The men were all gone and Marge and Trish were still asleep. I joined the ladies in the shower and then on the sitting room floor. Sylvia had an orgasm with Emma and another one from me. She also gave Emma an orgasm too. We invited her to join us for breakfast but Sylvia said that she had to get out on deck and find herself some more men to fuck. She said that if things got slow that she would be back. I had to smile at my sophisticated slut. I had some very nice pictures of her standing nude with seven men and with three other women. She told me to do whatever I wanted to do with the pictures of her.
As the week progressed I fell in love with Emma. I talked her into staying on for the rest of my stay and in my cabin. She insisted that I still get the full benefits of my cruise, so for the next three weeks Emma continued to help me fuck as many women as I could.
The very last day aboard the ship before we pulled into port Emma and I were married by the Captain.