Our First Time Sharing in Cabo

NOTE: This story contains wife sharing, swapping, and some male bi-sex. If you don't like that stuff, don't read it. This is the second half of day 2 of the vacation. This is a fantasy and it never happened. It probably couldn't happen. If that also bothers you, then stop now. Otherwise, I hope you enjoy the fantasies of an old guy.

*****

"So, do you want me to ride you again before we go or do you want to ride me?" Cheryl asked.

"Well, I'd like to do both, but if we don't go now, we won't make our paddle boarding tour."

Cheryl agreed and she had quite a few orgasms. She was just thinking of me. I told her there would be plenty of time. Although, I'm not sure why, I did let her in on the secret about my record.

"So, I've had two orgasms today. Five is my record since I hit about fifty or so, and two of those were from masturbating. Marti and I normally don't even have sex every day so I'm not even sure what I can do. I'm sort of surprised at three orgasms yesterday and now already two today.

"Really," she said. "That's pretty good for an old guy. Maybe I'll have to make sure you get six today? It will be my Christmas present to you."

"I'd love for you to help me break the record," I said.

We left for our paddle boarding tour holding hands. We arrived for instruction and paddle board check out still holding hands. We got some funny looks. I hadn't thought about the fact that I was old enough to easily be Cheryl's father, almost her grandfather. We began the paddle boarding session. It was great fun. I stayed a little behind Cheryl so I could watch her lovely muscular body paddle the board and watch her ass tighten up with each stroke. She figured out what I was doing, and she slowed down until I caught up to her. "My turn," she said. "get up there old man so I can check you out."

I obeyed and paddled ahead. We made it to the arch and walked around. We shot some pictures of ourselves and the scenery. We asked some of our fellow paddle boarders to take a few of us. They were pretty innocent, but Cheryl insisted we have a couple taken of us kissing. She held my cock in one of them.

After a while we got back on the paddle boards and went back to the resort. It was dark by the time we got back and we were tired. We sat in the hot tub for a while and kissed and played. We figured that the others would be back already or at least soon so we got out. Sure enough, Marti was back in our room when I got there. She had just arrived back and was in the shower, so I joined her.

We played around in the shower and then got out and dried off to get ready for dinner. We talked about our day and how much fun we had paddle boarding and snorkeling. I told Marti about the playful time with Cheryl and she said the guys would pull down her bathing suit top and kiss her breasts whenever no one was looking and even a couple of times when they weren't sure. They also kissed her just about every time she came up above water. I told her I was ready again to fuck her, but she said I had to wait until after dinner since Chuck, Cheryl and Pete were now expecting us.

It was Christmas Eve dinner, so the resort had a special menu for dinner. We had a little surprise when the older woman I had "met" in a tug-o-war over the exercise mat joined us alongside Pete. The six of us enjoyed our time together.

The new woman was Kathy. She was indeed 65 years old. I nailed that one. She was from southern California and was wearing a tight white dress that went to mid-thigh. She looked incredibly hot. I am not usually turned on by older women, but I had never met a woman of that age who looked that good.

Nothing special happened at dinner. We just talked about our lives and where we lived and jobs. Kathy said she had to go back to her room. I assumed it was to get ready to be with Pete. That's when Marti surprised me in front of the others.

"Don, I have a request for a special Christmas present." She said.

I was all ears. I was hoping it would be the threesome.

"I'd like Pete to spend the night with me tonight, on Christmas Eve."

I knew she had taken a liking to Pete, but this was interesting. I was actually kind of excited about it, but then I would be alone on Christmas Eve. Selfishness kicked in and so I had to think fast. I really wanted to show Marti that I loved her. I didn't want to be selfish. It wasn't that outrageous of a request. I almost asked if I could stay with them for a Christmas threesome, but if that's what she wanted, she would have asked.

Cheryl whispered to me, "If you get lonely, you can come to our room for your Christmas record."

That was encouraging, but I didn't want to barge in on their plans for Christmas Eve. Marti looked at me with eyes that told me she really wanted this. She leaned over to me, "I'll make sure your Christmas is really special."

I couldn't resist. I had options not to be alone. I really wanted to give her what she wanted. So, I said yes. As much as I wanted to be with my wife on Christmas eve, the thought of her spending the night with Pete and the stories the next day were even more attractive. I took Pete's room key and went to our room with Marti so that she and Pete could be in our room. Why she didn't go to his room, I'm not sure, but I guess she liked the control. I gathered a few things for the night. Marti thanked me again for her Christmas present and kissed me and gave my cock a squeeze. She again assured me that Christmas would be wonderful and she'd make sure.

I wasn't completely confident, but I did agree to it. I could have backed out, I suppose, but there was also a part of me that didn't want to back out. I liked the idea of my wife pleasing and being pleased by another man for a night.

We all took off for our rooms for the night. I went to my room and Pete had given me an extra key to his room so I could sleep there while he slept with Marti. I headed off to Pete's room and passed Pete coming to my room. Our rooms weren't more than six or so rooms from each other. I told him Merry Christmas. And he said, "oh, yeah. Thanks, Don." I still couldn't decide if I had made the right choice, but Marti would be happy.

Once in Pete's room, I pulled out a beer. I wasn't sure what I was going to do. I was horny as hell thinking about both Cheryl and Marti and even about Kathy now. I hadn't had an orgasm since just after lunch, and I knew I was ready again for at least one more round. I thought about the gym or the bar. The bar would be a better place to find someone. There was always Cheryl and Chuck's room. Fucking Cheryl while she sucked Chuck would be great.

I was sitting there in my underwear contemplating my options, when there was a knock on the door. I opened the door to find Kathy standing there in a casual dress about to her mid-thigh. It wasn't particularly sexy, but given my state of mind, she looked very hot to me. She was carrying an overnight bag. She said she was coming to talk with Pete. I told her Pete was gone already, but she could come in for a little while.

I was confused. I thought Pete would be with Kathy, but he was with Marti. Kathy was alone. I was alone. Hmm. This was very strange, but Kathy did accept my invitation to come in.

Kathy sat down to have a glass of wine with me. I finished my beer while she drank her wine and we talked a lot. We found that we had similar interests in music, dancing, books, exercise and just about everything. She also had a great sense of humor, and those legs. I couldn't get over those legs. Then she kicked off her heels and I couldn't get over her feet. I love feet and hers were perfect. She had nylons on, which I thought was a little strange given that it was evening and she was just in a sun dress.

She was extremely hot. I was lonely and asked if she wanted to dance. She agreed. She was a great dancer, much better than I was. We danced at least three or four dances, but Kathy seemed nervous toward the end. We sat to finish out drinks.

I told Kathy how much I loved her feet and gave her a foot massage. She seemed more uncomfortable than someone getting a foot massage should be. I asked if she was OK and she said she loved the massage. I rubbed her feet over her stockings. I wasn't daring enough to take them off.

Evidently Kathy had enough of my foot rub and thanked me. She got me up and moved my chair close to the bed and sat me back down. I was still finishing my beer when she pulled her dress over her head to reveal incredibly sexy black lingerie with matching garters holding up her stockings. The bra and panties were mostly lace with a floral pattern. They showed a lot of skin. I could see her small nipples through the material. If I was hot before, I was definitely stirring down there now.

Kathy pulled down my pants and pulled out my dick and began massaging it with her hands until it was fully erect. So far she had said nothing. Then she sat me back in the chair and sat in front of me on the bed. She then put my cock between her feet and gave me an incredible foot job. I'd never had a foot job before. I couldn't stop staring at her beautiful feet as they rubbed up and down my cock. I finally was able to unglue my eyes from her feet and allowed my eyes to travel up her stockinged legs with knees flexing to extend her legs so her feet could slide up and down my dick. I continued looking up her legs and into her crotch, barely covered by the lacey panties. The panties did have a solid crotch panel, but I could see through the lace to see that she had a shaved mound.

I was really enjoying this and my cock was definitely feeling like it was going to get messy soon, but Kathy kept on rubbing. I let my eyes travel from her crotch up to her perfectly flat abs. She had great skin, especially for her age. Looking at her from foot to chest, you would never guess this was the body of a sixty-five-year-old. I made my way up to her chest with her small, but perfectly round tits and tiny areolas and nipples. I savored that view for a few moments and then looked directly into Kathy's passionate eyes. She was pumping my cock as fast as she could. Her eyes were on fire. She was focused on her feet rubbing on my cock.

She noticed that I was looking into her eyes and she began staring into mine, almost challenging me to cum.

"Oh, my god, Kathy. This is so good." I said.

"You like this?" she asked smiling.

"Oh, yes, yes, yes, yes," I said, not knowing how many times I said yes as my cock shot streams of cum while I was still staring into her eyes and not caring about the mess I was making.

She continued stroking my cock until I was finished. I looked down and there was cum all over her feet and ankles, even one shot that almost hit her knee. Without a word, but with a smile at me and with bright hungry eyes, she reached forward as if doing a hamstring stretch, touched her hands to her feet. This time she wasn't just stretching. She wiped as much of the cum from her feet and ankles as she could and she scooped it into her mouth.

"Oh, wow, Kathy, that was so sexy. Your pussy looks like it would be so pretty too."

I sat back to relax and watched her scoop the cum from her nylons and into her mouth. Then she lay back on the bed. I looked at this beautiful woman on the bed. The bed that I was sort of forced into and would be sleeping on, perhaps with her. I got up out of the chair and reached out and removed her panties. She didn't resist. I pushed her legs up toward her head to get her ass rolled up off the bed and proceeded to give her ass a nice licking. I tickled her little hole with my tongue. I circled around the hole, then I would plunge in and wiggle my tongue as best I could. I licked at the strip between her butt hole and her pussy, and then moved directly to her pussy. I licked gently at first, then began speeding up the flicking around her clit, circling and circling. I circled around her clit until she began calling out.

"oh, yes, lick that pussy, yes."

I then began direct pressure as her pussy was dripping with her juices now. I licked into her pussy to get some of her juices. I put my fingers into her opening to get more and I removed my mouth just long enough to wipe some of her juices on her clit. I licked her clit with direct pressure, just like it was an ice cream cone. Her body convulsed and she gasped for air.

"Oh, yes, that's good, very good, lick me like that, just like that."

I continued that technique, loving the way she tasted and trying to fill my mouth with her juices, when she stiffened completely.

"Oh, Oh, Oh," she whimpered. Her body shook three or four times, completely stiffening and then relaxing. While she was still catching her breath, I moved to kiss her mouth and fondle her breasts. I began some serious kissing along her neck and then her breasts. I loved the shape of her small breasts. I kissed and licked around them, then circled in on the nipples and then nibbled them. I then took each one into my mouth. I could get her breasts all the way into my mouth if I opened wide and sucked hard. Then I worked back around them again, then kissed her chest and neck and back to her mouth. She opened her mouth to mine and she tried to hold my tongue with hers. We played tongue tag for quite a while.

I was surprisingly ready again rubbed my cock against the entry to her pussy. I was so hot missing my wife and having this lucky break with this incredible woman who I had so much in common with and who was so elegant. She was so classy. I was going to enjoy this fucking. I inserted my cock into her pussy and she moaned with delight.

"oh, yes, that's nice, so nice," she said.

I began to rock in and out of her gently and tried to make sure she enjoyed every stroke. I was making love to her as I had already developed a strong liking for her. My thrusts met her hips lifting from the bed. As we developed a rhythm, we moved faster and faster.

Kathy looked at the clock and said, "Oh, I'm so sorry. I have to go. I have to go. I'm so sorry. I had a great time." She pushed me off her, put on her dress and grabbed her shoes and overnight bag and ran out the door. I was completely confused. Where could she have to go at this time of night? I noticed her panties on the floor by the foot of the bed and picked them up and smelled them. The reminder of the recent whirlwind of sex flew back through my mind.

My crotch stirred. I was so horny and now knew that I could get at least one more orgasm in. I sat back down to figure out what to do. It was Christmas Eve and I was lonely. I had such great hopes that Kathy would spend the night that being without her reignited my feelings of loneliness and self-pity. I thought about the bar, but I'd be even more disappointed if I struck out, and I was standing there with a softening cock that needed attention.

I thought for a moment. As much as I didn't want to bother Chuck and Cheryl, Cheryl had invited me over. Perhaps Chuck wouldn't mind. Perhaps he'd enjoy a threesome. I'd had four orgasms today, which would normally more than satisfy me. In fact, it would be unusual, but today it wasn't enough, especially given that Kathy left me probably a few minutes from me cumming in her tight pussy.

It was about 10 p.m., I walked over to Cheryl and Chuck's room still not sure I should, but she offered and I was lonely. Even if they'd let me watch them or sleep with them would be great. Even if I could sleep in the spare bed, that would at least be someone to be with.

I knocked on their door and Cheryl came to the door dressed in only a thin transparent robe with nothing underneath.

"I was hoping you'd come." She said. "Chuck's asleep. We had some great sex, then he decided he was tired."

I thought she'd invite me in, but she came outside with a blanket. There was a small common area between the buildings that was poorly lit and perhaps with this being Christmas Eve, there was little foot traffic. She began kissing me and fondling me. A few people did walk by, but they didn't pay attention to people kissing on Christmas Eve. Cheryl led me to a dark part of the common area, but at least twenty feet from her room.

Cheryl undid my pants and slid them down to my ankles and then bent down to help me step out of them. She then slid down my boxer briefs and pulled them off as well. Then she stood back up and continued kissing me.

We kissed like that for a while, just standing in the middle an open area. I still had my shirt on, but even though it wasn't well lit, I was sure that anyone passing by could tell that Cheryl was essentially nude and I didn't have any pants on. Cheryl broke the kissing off, and got on her knees and began sucking my cock and massaging my ball sac. She was rotating her hand around my cock and slurping at the head. She was licking almost painfully hard on the underside of the head of my cock and it was at full mast again.

"You've got pussy on this cock, you naughty boy. Where did that come from?"

As she sucked my cock, I told her the essentials of what happened with Kathy.

She stopped long enough to say, "You are a naughty boy, and I'm a jealous girl and she was stupid to leave you like that. I'm going to fix you right up."

I thought she was going to finish me off as she began sucking my entire cock into her throatMarti didn't suck cock like this and it was crazy good.

When she had me hard, Cheryl turned away from me and put her hands on the ground.

Turning her head to face me, she said, "What are you waiting for? Fuck me. I'm not going to leave like Kathy did. You need to get off."

I thought she was crazy, but it was Christmas Eve and I was going to fuck a beautiful young woman in public. It was worth the risk. I lifted the back of her sheer robe and reached for her clit with my right hand as I used my other hand to get my cock in her pussy. She helped with one hand.

Cheryl told me to hurry because even though she wanted to be daring, she didn't want to be caught. So, I both rubbed her pussy faster and harder than I normally would, trying not to be too harsh. I also was ramming my dick as fast and deep into her pussy as I could.

Cheryl moved my hand from her clit and took over stimulating herself. She said, "Squeeze my ass...hard."

I did as requested. I squeezed her ass with both hands as I continued to plough into her. She worked frantically on her pussy. I loved the feel of her small tight muscular ass. I both massaged it and held it for harder pushing.

"yes, just like that, pound me with your big cock." She squeaked as she said it with every thrust into her.

"Pinch...my...nip...ples...oh...god...oh," she said. I continued in and out of her pussy and leaned forward to pinch her nipples.

"yes...just...like...that...like...that...like that...yes...oh...oh...oh god...oh god...I'm go...ing to...cum...oh."

She didn't lie. My pounding of her pussy, my pinching her nipples and her hand on her clit finished her off. Hearing her sent me over the edge too and I had to let go of her nipples as my body straightened up involuntarily. I continued pumping until I was sure that every drop of cum was in her, as little as that was for my fourth old guy orgasm of the day.

We heard clapping. Chuck had woken up and was standing in their doorway. He was very impressed. "Bravo," he said. Then he shuffled us inside. "Are you crazy?" he asked, mostly to Cheryl. She just smiled a happy smile. We walked back into their room, my cum dripping on the walkway from between Cheryl's legs.

We all talked for a while. Chuck marveled again at how crazy his wife was. I agreed, but said I enjoyed it. Then after about a half hour of friendly talk Chuck went back to bed.

Cheryl and I got in the shower. We soaped to clean each other but mostly we were there to cuddle privately with the warm water. She asked me if I could fuck her again and I was surprised to notice that I might be able to, mostly just due to the excitement of her small young body and the wild sex we've had. I also love that soapy slippery feel of a woman's skin in the shower. I told her I might be able to, but couldn't promise at that point. I let her know that I hardly had any cum in me in that last orgasm.