Cruise

My last year of university, I worked with an older woman (Ginny) who took me under her wing. She was almost 20 years older, married, with two teenaged daughters. We went out for a drink a few times after work, but there was never anything beyond that. My last day there, before moving on to my first real job after graduating, she gave me a card and a kiss on the cheek.

I ran onto her about ten years later, at the food court in the local mall. We hung out for about half an hour. She was still an attractive woman, although carrying a few more pounds and a few more wrinkles. About a week later, at the end of the day, she dropped in where I worked, and asked me out for a drink at the bar where we used to go. We met there, and had a few drinks. I learned that she was putting together plans for a week-long cruise, with two friends, for her 50th birthday. We met there again a couple weeks later, but this time the conversation grew more intimate. She asked me point blank if I wanted to accompany her on the cruise sharing her room. She offered to pay for my ticket, saying she could add me as an additional passenger using the same room for a minimal charge. Her husband would not know, although she told me that they hadn’t had sex in a long time.

I had vacation time, and a week on a cruise ship sounded great. The sex with an older woman would be a bonus. We met a few more times for drinks, and on one of those occasions she invited the other two friends who were going on the cruise with her. After she told them she was bringing me along on the cruise, they insisted on meeting me just to make sure I’d fit in with them for a week on a ship. Both were about her age and also married.

One of them, Kirsten, was a big woman, close to six feet tall, and big boned. The other, Katie, was a very petite woman who didn’t say much and I got the feeling that she didn’t approve of Ginny bringing a guy along. She stayed for one drink and then left. While I was up at the bar ordering another round, Kirsten asked Ginny if she might be able to “borrow†me for a night during the cruise. Ginny told her that was up to me. After I returned, she asked me point blank how I would feel about sleeping with someone larger that I was. I grinned and told her that would be just fine. Both made me promise not to say anything to Katie, who was pretty conservative.

The day came, we boarded the ship, and went to unpack. We all met in one of the lounges for a drink, and then had dinner, before going back to our rooms that evening. Ginny took a shower, and came out wearing just a towel. We began kissing, and my clothes came off, as well as her towel. We got into the bed, kissed some more, and I explored her while we kissed. I could tell she had inserted an oily lubricant as soon as I fingered her. My finger inside her was causing her to moan, until she rolled over on her back and pulled me on top of her. She used her hands on my butt cheeks to establish my rhythm in and out. She made little gasping noises, but was not very vocal. It was a nice ride, and after I finished, she rolled over putting her back to me, with my arms around her.

We chatted for a long time, until she took my hands and put them on her breasts telling me to pinch her nipples. My fingers began squeezing them, and she started squirming against me. I put a couple fingers inside her, moving them around her sperm-soaked vagina, and she started to moan. She rolled over on her back again, and I entered her. This time she was more vocal, and gave out a long groan as her orgasm was passing through her. After I spurted up inside her, she rolled away from me again and we fell asleep.

In the morning we showered separately and met the other two for breakfast. After, we all changed into bathing suits and met at the pool, grabbing some recliners. Ginny asked me to apply oil on her, and then I did the same for both Katie and Kirsten; all three were wearing modest one-piece bathing suits. Ginny and Kirsten had some cellulite on the back of their slightly flabby legs, but Katie was toned and smooth. We had lunch outside, and spent a few hours under an awning over the table, drinking some umbrella drinks. Everyone went to shower and change for dinner. Ginny and I showered together, but she told me she was too sore to have another coupling.

After dinner we went to the lounge and listened to a mediocre band. Once again, Katie left early. Soon after, Kirsten and I walked up to her room. She was wearing heels, and towered over me by at least four or five inches. In the room, she asked me to unzip her dress, and shrugged out of it, wearing just a bra and panties. I started to undress, but she told me to let her do it. Once I was naked, she asked me to remove the rest of her clothes, and then she rolled over onto the bed. Following her, she grabbed both sides of my head and started kissing me.

Our kissing lead to exploring, and then to oral sex. She had trimmed her pubic hair to a very short length, and I moved down and began kissing her there. She was enjoying it, moaning loudly, and put her hands on my head to guide me to the right place. It took a long time until she started panting and moving her hips up and down, quivering, then started a squealing noise that broadcast her orgasm. She pulled me up, kissing me, pushed me onto my back, and then squatted over me, stuffing me inside her. Unfortunately, she was very tight and I lasted only about 30 seconds.

We fell asleep, and she woke me up just as daylight was starting to show through the curtains on the window. I was ready in a matter of seconds, and she climbed on top of me again, lowering herself down until I was buried inside her. This time I didn’t get to the end until she had squealed twice. My dinner clothes were on the floor, so I put them back on and went back to my room. Even though I had a key, I knocked on the door. Ginny opened it for me, just wearing a nightgown.

We showered together, but she was still somewhat sore, so there was no sex. Like the day before, we all met for breakfast and then at the pool. I was the official sun screen applier, and did my duty. I gave Kirsten some extra rubs between her thighs, after checking to see that the other two were turned away from us. She reached down and moved her bathing suit aside so I could put a finger up inside her. I could feel the remnants of my ejaculations and she had to pull me out when her breathing started getting heavier. We ate lunch, had some drinks in the afternoon under an umbrella, dinner after changing in our rooms, and then we moved on to the lounge to watch people sing Karaoke. With Ginny whispering in my ear, I learned that I would be going to Katie’s room later, but Kirsten was not to know. After Karaoke we walked to our rooms, and then Katie called our room to say the coast we clear. Ginny told me that Katie had never strayed, and she was surprised that I was going to her room.

As soon as I entered her room, Katie told me that there would be no intercourse. We spent an hour or so on her bed, with our clothes on, making out. Although I tried, she rebuffed my efforts to touch her in more intimate places. Around midnight she kicked me out and I went back to Ginny’s room. Upon questioning, I told Ginny that all we did was kiss, and she nodded her head, saying that was more than she expected would happen. Ginny was still experiencing some soreness down there, but she gave me a nice blowjob before we fell asleep.

Same daily routine, and I had sex with Ginny that night. The next day was the same, but Katie, who had kept her legs together the previous times I oiled her up, had moved them slightly apart and I was able to put lotion between her thighs. I kept my fingers a couple of inches away from the bottom of her swimming suit, but could see a couple of pubic hair strands peeking out.

I spent the night with Kirsten, having sex twice, the second time in the shower in the morning. She started out by soaping me thoroughly, then she inserted a very soapy finger up inside my bottom before turning around and bending over. I took her from behind while she was panting and pressed up against the wall of the shower.

There was only one night left in the cruise, and after we were all in our rooms the next evening, Katie called, asking if I wanted to visit her again, and I walked to her room. I was wearing shorts and a tee shirt, and she had also changed out of dinner clothes, dressed in a knee length nightgown. We started kissing after moving to the bed, but I started playing with her boobs outside of the gown, and then pulled the low neck down and began sucking her nipples. She put a leg over mine, and I moved a hand down to her bottom, squeezing and rubbing. I then moved it down her thigh and brought it back up under the gown, reaching a very thick patch of pubic hair. One finger went inside her, she opened her legs, and then a second was inserted. By this time, she was moaning, and her chin was pointed straight up.

Suddenly, she pulled away from me and lifted her gown up over her head. I pushed my shorts down, she lifted her legs straight up into the air as I moved between them, and I punched into her. It was a fast and furious fuck, and both of us were panting for air once it ended. She made me promise not to tell Ginny (or Kirsten) and sent me back to Ginny’s room after a lot more kissing.

Ginny was still awake when I knocked, and after some kissing, told me she was still tender. She yanked my shorts down and took my limpness into her mouth. That only lasted a couple seconds, until she tasted Katie’s fluids. She took her mouth away and said, “Oh my God! She did it!†She made me go wash up and then finished what she started. I offered to reciprocate, but she said it would hurt too much. Telling her that Katie did not want her (or Kirsten) to know, she smiled and said she would keep the secret.

The next day the cruise was over and we all went home. There is a twist to this though; Katie had asked me where I worked, and showed up there a week later. She met me after work for a drink at the bar, and I found out that she was the daytime manager at a motel. For the next few years, we met frequently at the motel during lunchtime, and enjoyed each other. I never saw Kirsten again. Ginny and I met occasionally at the bar, but never had any physical encounters. Although she asked a couple times, I denied having ever met Kirsten or Katie again.