Our First Time Sharing in Cabo

She told me that she and her husband were swingers and she had come out hoping to find someone to take back to her room. They weren't "experts" but had been with three other couples over the past year. None of the relationships ended up being long term or serious. She and her husband got two beds in their room just in case they found another couple here.

I couldn't believe she was telling me all of this as we'd just met when she held my hand and said, "I've always wanted to have sex with an older guy. You are really hot and I love the fact that you look so fit. It's a turn on for me. I've never been with a guy that's as fit as I am. I love it."

She leaned over and kissed me, placing her hand on my cock as she did so. "So, have you and your wife ever swung?" She asked.

I sort of lied and was telling the truth at the same time. Since Marti was with Pete, I suppose we now were swingers. "Yes," I said, and left it at that.

She said, "good" and held my hand again. She kissed me again. "So, would you like to come back to my room?"

Do I need to think about this? I'm 57 being asked to have sex with a cute 22-year-old while my wife is fucking another guy in my room. I'm no fool. As strange as this day was, I wasn't going to pass this up. My only fear is that having cum twice already, could I make it happen again. I was pretty excited and felt some movement in my pants, so I knew I could get an erection. I decided to take a chance.

Cheryl's room was one building over from ours. They were also on the first floor. Chuck was asleep in the bed farthest from the door. Cheryl led me to the other bed. I was nervous, but excited. I'm not sure if she could tell. We slowly kissed and undressed each other. I spent a lot of time with her tiny, almost non-existent tits. I'd never been with a small breasted woman before and I found it a real turn on. She was so tiny too, so young and so muscular. I kissed and adored her six pack. Maybe that seems weird, but as a fitness buff, it was a real treat. She was still standing next to the bed. I was on my knees kissing her muscular thighs and around her pussy. I kissed all the way down to her feet and asked her to lie back on the bed. I then kissed her feet and licked each toe as well as the soles of her feet. I love the taste of a woman's' feet almost as much as her pussy.

I then worked my way back up to her pussy and began licking and couldn't stop. I caressed her clit with my tongue and then began licking it gently like an ice cream cone. Her hands were on the back of my head.

"oh, Don," she said softly trying not to wake her husband. "oh, wow, oh." At the same time, she was pushing my head into her sweet honey comb. She reached orgasm and her hips bucked on the bed and squeezed my head with her strong thighs. She sighed when it was over. I then crawled on top of her and we cuddled until she was ready to have me inside her. I first rubbed my dick on her clit, then slid it inside her hole. She was very wet and there was no resistance.

"Oh, you're big." She said.

As I had not been with many women, I really didn't know. I had measured myself a few times when using a penis pump or masturbating. My length varies from about 7 ½ and 8 ½ inches depending on how excited I am. Marti can tell when I'm extra big and always mentions it. I knew from reading that I was probably slightly above average, but I didn't really consider myself huge. Perhaps that's from looking at too much porn and those guys with ten to twelve inch cocks.

I continued to move inside her slowly. We stuck with the missionary position. She told me how much she liked it and I agreed that this was fun. She said, "You've never been with another woman before have you?"

I admitted that I hadn't. We were still fucking and it was funny to talk about this while fucking, but I told her what was going on in my room. She laughed. She understood then why I had told her that my wife and I were swingers. She thought it was funny. Then she said, "I'm glad I'm your first. Now, fuck me hard."

I obliged. I fucked her as fast and hard as I could. I almost felt guilty because I was going so hard, but she kept urging me on. "Yes, Yes. Fast. Just like that."

As far as I could tell Chuck was still asleep in the bed next to us. It was difficult to tell because he was facing away. I was pounding Cheryl into the bed when I started cumming. It was an incredible release in this woman I had just met. It was such a new feeling and with a young admirer. I felt a little guilty for releasing before she reached orgasm, but as I had already made her cum by eating her pussy, the guilt subsided. Besides I could still give her an orgasm with my fingers or I could eat her again if she wanted me to.

We lay there together intertwined. We smiled at each other. We connected. That was great. I realized this wasn't just sex. "It wasn't like this with the other guys." She said. "It was just sex with them." It was nice to know that she felt the same way I did.

I told her I felt the same way, only I hadn't experienced another woman before since my wife and I got married. We cuddled and nuzzled. She giggled. I smiled. I squeezed her tight muscular ass. I bit her little nipples. She squeezed my cock and grabbed my ass. I looked at the clock and I had about a half hour left. I didn't want to be late. I also thought that perhaps I'd catch Pete with Marti and get to watch the finale. But, with a half hour left, I figured why not stay and see if I could get in round 2. My 57-year-old cock was starting to stir again, and why not? I was with a 22-year-old woman who wanted me. I rolled her onto her stomach and began giving Cheryl a rim job. I've never done that to Marti, but always wanted to. I feared that she would reject it or think it was gross. Cheryl just moaned with pleasure. I thought about fucking her ass, but that might be too forward for our first meeting, I felt my manhood stirring again, but realized that it my half hour was pretty close to being up.

Cheryl wanted me inside her, even though I told her I had to leave in five minutes. I knew there was no way that I could cum again. She insisted that I slide myself in her again, even if just for her to feel my cock one more time before going to bed. So, I obliged her. I positioned myself behind her so that I could better observe her tight ass. It wasn't big at all, but it was very well shaped for a little skinny girl. I pushed in with her on all fours.

"oh, he's getting bigger," she said.

I did feel as big as I'd ever felt. Perhaps it was her tight pussy with her muscles squeezing my cock, but I felt huge inside her. I reached around to rub her clit. She was now almost screaming even within the five minutes..

"Oh, I love your cock, yes, fuck me. Fuck me."

Chuck began to move and I saw him roll over. If he was asleep before, he wasn't any longer. He had rolled completely over and was watching me fuck his little wife. It just made it all hotter as I continued to pound Cheryl and rub her clit and I could tell she was about to orgasm, so I couldn't stop. Unfortunately, I wasn't able to cum, but she went over the top.

"Yes, oh, yes, fuck me like that, Yeeeeeessssss." She called out as she hit her peak.

I looked over and Chuck was awake. Chuck smiled as our eyes met. I hadn't even been introduced, but there I was completely naked with my cock inside his wife doggy style. Wow. This was only day one of my vacation?

When Cheryl and I had recovered. Chuck said hello and introduced himself. "It seems like you and Cheryl have met." We all laughed. I introduced myself. Cheryl told Chuck she was going to enjoy this vacation and looked at me and said, "Right?" Wow, again. I hadn't had time to think about this being more than a onetime thing, but if Cheryl was offering...I realized I'd need to check with my wife. I really didn't even have permission to do this. I mean, maybe it was implied by her telling me to have fun while she was with Pete. And there was that. She was fucking Pete or at least finishing off. I looked at the clock and realized I was a few minutes late. I got my clothes on and excused myself and Chuck and Cheryl laughed. "Fuck and run, eh" Chuck said.

"Yeah, sorry," I said, looking at both Chuck and Cheryl. "It really was great, Cheryl. I'm sorry I have to run."

She understood and gave me a big hug and a big kiss with lots of tongue before she let me put my clothes on. We exchanged cell numbers and I left with her naked on the bed we had fucked on and staring at me as I left. Chuck was still under the covers in his bed.

I got back to my room and to my dismay, Marti was alone. Pete had already left. Damn it, I thought. Marti was in bed by herself with the covers on, but not asleep. She had that guilty look on her face and her body language was also submissive. She sat up and let the covers drop, exposing her tits to me. "I don't want to talk about it yet," she said. "Fuck me?"

I glad that I hadn't cum with Cheryl on that last fuck. I still wasn't sure I could cum, but I knew I could get an erection. I was sure going to fuck my wife. Thinking of her fucking Pete got me horny again immediately. There was my freshly fucked wife waiting for me. If I wasn't sure before what I would think about sharing her, I knew now. She was sexier to me now than ever before.

We made love for about 45 minutes. We began with lots of kissing and being reacquainted. Then we sixty-nined. Then I fucked her in the missionary position so we could look into each other's eyes. It was clearly a time to reconnect and we both knew it. We both brought each other to orgasm and collapsed on the bed.

"You ate someone's pussy tonight, didn't you?" she asked.

"Yes. I did." I said. "I know I didn't really have permission, but you said to have fun and you were with Pete, so I did. I'm sorry."

She told me she didn't blame me. She asked if I had also got laid and I said yes. I told her about Cheryl and how we met at the bar and that she and Chuck were swingers.

Marti told me that it was exciting meeting with Pete and she pulled down his pants and began sucking on his cock as soon as I left the room, she really wanted him. Of course, I saw that part, but didn't tell her.

Then she said that he ate her pussy and that he played with her asshole (which she never allowed me to do) and then they went to lots of kissing after that. They kissed for a long time, then she blew Pete again to get him hard, but at the last minute, she just couldn't have sex with him and that she felt guilty. She just couldn't let him in her pussy. Boy, did I feel like a jerk at that moment, but how could I know? She seemed so excited about it. How could I know she wouldn't fuck Pete?

She said Pete was very kind and understanding. They talked for a few minutes and continued cuddling and Pete began rubbing her clit, and Pete asked about her ass. He told her he had seen us through the window and loved her beautiful ass. Fucking her ass wouldn't be like fucking her pussy. She told me that she was hot from the kissing and breast play and the fingering of her asshole and the rubbing on her clit that she agreed. Pete had brought some lube just for that purpose and he eased her into it. We'd never had anal before, another thing that Marti had thought was gross before. She said fortunately he was not as big as I am so she wasn't too worried about pain, but it did seem strange at first, but she ended up loving it so we had to try it.

Yep, Twist my arm.

She continued that Pete rubbed her pussy and made her cum while he fucked her ass and came in her ass. Then he cleaned her ass hole up with his tongue, which she loved as well. They cuddled for a while longer and he kissed her breasts and rubbed her clit. She had changed her mind and wanted Pete to fuck her, but Pete couldn't get it up again.

"He's not like my superman," she said as she held my cock and rubbed it gently, knowing I had three orgasms in the past five hours. We went to sleep spooning each other.