Our First Time Sharing in Cabo

Day 3, December 25th, Christmas Day.

I woke up and looked at the clock. I had forgotten where I was, but I remembered quickly. It was 5:30 a.m. and Cheryl was sucking on my cock. That cute little girl was insatiable. As my eyes cleared, I saw her smiling up at me. I slid Cheryl around so that her pussy was in my face.

I began to eat her pussy. I slid my legs off of the bed and Cheryl stopped sucking my cock for a moment as I stood up holding her with my arms wrapped around her torso. Cheryl got it and wrapped her legs around my head. I was standing eating Cheryl's pussy and she was upside down sucking my dick. I'd always wanted to do this, but Marti didn't really like the idea because she said she was too heavy for me and was afraid I'd drop her, but Cheryl was so light. It was easy. She began sucking me even faster. She took my cock all the way into her throat and then out again.

I took her lead and began licking her faster as well. I kept licking her pussy, still standing.

She tried to moan, but kept sucking my cock. It was an odd sensation when she began bucking her hips against my face as her thighs grasped my ears. My head felt as if it would burst as she tightened her grip. Then she went limp and I had to hold all of her body weight. Fortunately, she was light. I let her hang a few moments. Then I set her gently back on the bed, and Cheryl looked up smiling at me.

"Another new thing," she said. "You are full of surprises."

I lay down next to her on my stomach. Cheryl was on her back. We were enjoying looking into each other's eyes when I felt the bed move. I didn't look up, but I figured it had to be Chuck. Then I felt pressure on my asshole.

"Are you OK?" I heard Chuck say. I didn't look up. I had assumed it was Cheryl playing with my ass. The next thing I knew Chuck's cock was pressing into my ass. I couldn't believe it at first. We hadn't talked about this. I've never been attracted to men, but as I've gotten older, I had realized even before the trip that the idea of trying sex with a man wasn't out of the question. I have some gay friends and they've talked with me about some of their experiences, so I knew this could be pleasurable.

Still, I thought about stopping him, but then realized that I liked it. I let him penetrate me all the way. I even began pushing back against his cock. I pushed hard against him so he could get as deep into my ass as he wanted. Realizing this, Chuck kept slow and deep strokes. I felt his pelvis press against my ass on each stroke. I was glad that Chuck didn't have a huge cock.

As we got going, Chuck sped up and came faster than I had anticipated, but I felt the warm cum in my ass and dripping out. I lay on the bed contemplating this new feeling. I actually had enjoyed it.

Marti had done a little ass play with me before, but it was with a small vibrator and she mostly rubbed it around my ass hole and not in it.

"Are you OK?" Chuck said again. I assured him that I was and that it actually felt pretty good. I also realized that I had a hard on from being fucked in the ass. "Thanks," he said. I've always wanted to try it with a guy, but the other guys we swung with weren't into it."

I asked him why he thought I would be. He said that after the things he'd seen so far, he assumed I was on the daring side. I guess I was. I told him I wanted to return the favor though. He said he would love the opportunity. He went to the bathroom to wash off his cock.

"We also need to double fuck your wife soon," I said calling out to him.

"Yeah, we do." Agreed Chuck calling back from the bathroom.

I looked at Cheryl smiling at me while she was rubbing her clit. She mouthed, "Now."

I felt Cheryl's pussy and it was still incredibly wet. I rolled on my back and lubed up my cock with the anal lube. Cheryl got the idea. "Sit your ass on my cock," I said. She straddled me and then worked her way onto my cock with her ass hole. I was just getting all the way in when Chuck returned from the bathroom with a nice clean cock.

"Just in time," Cheryl said to him laughing.

"Oh, shit," said Chuck, "I'm not ready yet."

Chuck got on the bed and stuck his cock in Cheryl's mouth. She was rocking her little ass on my cock as best she could while trying to get her husband hard enough to go in her pussy. I told her she could take it slow and wait for Chuck to get hard. It took close to ten minutes or so, but being twenty-five, Chuck got it up again.

As Chuck moved to mount her pussy, Cheryl said, "Oh, Don, your cock feels so good in my ass, just keep it moving around like that." I didn't really need the encouragement. Cheryl's ass felt great wrapped around my cock.

Chuck inserted his cock into Cheryl and began slowly, but gained speed pretty quickly. I tried to meet his pace now completely skewering Cheryl like a shish kabob. She didn't mind at all.

"Wow, this is so hot," she said.

"Your ass is so tight," I said.

Because Chuck had already cum once this morning, he was taking longer than I thought he would. I, on the other hand, was still a bit worn out from the previous night, and I wanted to save something for my wife since she promised me a great Christmas Day. I actually decided to try not to cum. Something that wasn't easy given Cheryl's tight sphincter. I decided that I would at least try to hold out and just go easy on Cheryl's ass until Chuck was finished.

"Oh, god, this feels so good getting double fucked," said Cheryl. "You guys are my heroes."

"I get to be Superman," I said.

"I get to be Wolverine," said Chuck, "But I promise not to scratch you."

"just fuck me," Cheryl called out. "Oh, god, that's good, so good. I'm going to cum soon."

Chuck pumped faster when Cheryl said that. I also could tell that he was fingering her clit now.

"Oh, shit, that's good. So good. So good. So goooooood." Cheryl cried out as she hit her orgasm.

Chuck slowed to a stop. Evidently, even a twenty-five-year-old couldn't cum again that soon. I lay there with both of their weight on top of me.

"Um-hum, excuse me," I said.

Chuck apologized and pulled out of Cheryl. Cheryl was still reeling from the double fucking she just received.

"Thank you, guys, so much," she said as she kissed her husband and then got off of me. Then she turned and kissed me.

I got off the bed and put on my clothes.

"Where are you going?" Cheryl asked.

"I'm going to leave you to alone to have some cuddle time or whatever before breakfast. I'm also going to see if I can surprise Marti and Pete. Merry Christmas, you two."

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I went to go see how Marti was doing. Marti was an early riser and I did let Pete spend the night. It was now a little after 7 a.m. and I knew Marti was at least awake. I told Cheryl that I would meet her in the gym in about an hour and "Merry Christmas." She thanked me for my gift.

I headed over to my room. I hoped Pete would be gone, but I wasn't optimistic. I knew he was likely there, but that would be hot too. I entered the room and the first thing I noticed is that there were three bodies in the bed. That was a shock. I saw that Marti was on the far side of the bed facing away from the door. Pete was in the middle spooning Marti. The body closest to me was spooning Pete. It took me a minute, but I realized that it was Kathy. I figured what the heck. It's my room. They all seemed asleep, but with my wife on the other side of the bed and facing away from me, I couldn't tell. I felt a bit deceived and wanted to get mine, so I went over to see if Marti was awake. She wasn't or didn't appear to be, so I place the head of my cock against her lips. She was definitely still asleep, but I continued rubbing my cock against her lips until she woke up. She looked up through half open eyes and without hesitating, but still groggy, took my cock into her mouth. She was getting me good and hard. I didn't want to cum from a blow job though. I wanted to fuck.

I decided the easiest thing to do was to slide in behind Kathy. She seemed to enjoy my company the night before so perhaps she wouldn't mind if I finished what I started. She stirred and looked over her shoulder and smiled at me. She rolled back over to hug Pete's back. I rubbed my hard cock against Kathy's ass. She wiggled her ass a little bit encouraging me. I kissed along the back of her neck and reached around to massage her nipples. We went at this for a while.

I felt her pussy to make sure it was good and wet. My hand slid against her juicy wetness. I slid my cock into Kathy's pussy and began moving slowly trying not to wake Pete. Kathy began moving her ass in rhythm to mine. It was fun to try to be stealth fucking.

I felt really good fucking this elegant woman in front of my wife. I felt like it served her right for deceiving me. There was a large mirror on the wall across from the foot of the bed, and I saw Marti looking back at me. She was still awake and had been watching me fuck Kathy. She even gave me a thumbs up. I could also tell that she was fingering herself. I got a little bolder and moved a little faster inside of Kathy.

I noticed Marti's body flinching and knew that she had gotten herself off. Marti got up to go pee. She slapped my ass as she walked by. Kathy turned her head to smile at me again. I was getting close to cumming by now and I heard the toilet flush and Marti walking back out. I looked in the mirror and saw Marti stop behind me. I watched in the mirror as she pulled out a dildo. She rubbed it around my asshole and I moved my right hand down Kathy's body along her flat stomach and slowly along her mound. I teased around her mound and top of her vaginal lips before touching her clit. I wasn't going to be able to cum after last night. I had a good hard on, but I could tell that cumming just wasn't going to happen. Kathy began writhing with my dick in her and me massaing her clit.

Kathy hadn't had her orgasm yet and I think she realized I wasn't going to cum, so she slid my cock out of her pussy and rolled on her back and whispered, "Eat me." I started to move into position, when Marti beat me to it. I sat up and watched my gorgeous wife gently licking around Kathy's clit, circling around and around. I moved in behind my wife and inserted my cock into her pussy from behind while she ate Kathy. She didn't stop, but her ass pushed against me accepting my hardness. Still knowing I wasn't going to cum, I moved slowly in and out of my wife's hot pussy and reached around her hip to rub her clit. Oh my god. Merry Christmas. Kathy began moaning, but tried to be quiet as Pete still slept beside us. I could see the look of pleasure in her face as she stared into Marti's eyes. She smiled with a Cheshire gain smile. Then in an instant her smile turned to what was clearly ecstacy as her whole body tensed. Her head flipped backwards and her eyes shut. Still trying to be quiet, her orgasm overcame her.

Marti stopped licking, and I could tell she also was struggling to contain her pleasure. She was breathing heavily and I rammed my cock as deep into her as I could and held it there while I furiously rubbed her clit. Her breathing increased.

Kathy watched now, having opened her eyes and was smiling that wide smile again. Marti's head was still in Kathy's pussy.

I could tell Marti was going to cum soon. I still held my cock deep inside her. Marti had her head buried in the sheets now in front of Kathy's pussy. I think she was trying to muffle her moans in the bedclothes.

Kathy slid herself back toward the top of the bed, then got on her hands and knees and crawled toward Marti. She lifted Marti's head off the bed and began kissing her passionately. That set Marti off and within a few secons, she hips bucked back against me. I continued to rub around her clit slowly as her hips continued bucking.

Kathy's tongue tangling kisses kept Marti from being load in her orgasm. They broke the kiss long enough for Marti to giggle, then began their frenching again. Marti's hand gently moved my hand from her pussy and I started to slide my dick out of her wet opening when I heard an "uh-uh" from Marti. So, I held myself in there. To keep myself hard I began moving around a bit.

I had been so hard so long and so turned on that I realized that I probably could come, so I began moving faster while the ladies continued to kiss. The sight of my wife's round ass cheeks engulfing my cock and her little butthole staring me in the face made me even harder and I decided that if she liked ass play now, I'd join the game.

As I began pumping the ladies seemed to kiss even more passionately. I rubbed my finger around Marti's ass bud while I moved as quickly as I could in and out of her pussy. She squeezed her pussy muscles around my cock and I could even feel her hip bones putting pressure on me. I continued to put pressure around her little ass bud and while a few days ago, she would have told me to stop, today she enjoyed it, lost in her passion.

With one more stroke, I came into her pussy. I tried hard not to grunt too loud. Pete still slept. I pushed forward hard and held my cock deep in my wife. Her face pushed Kathy's face back and Kathy broke the kiss stifiling a laugh.

Kathy returned to kissing Marti as I finished my orgasm and returned to normal. I slid my cock out of my wife's pussy, but the girls continued their make out session as if nothing had happened.

I got off the bed to watch this erotic session. The first time I had seen my wife with a woman. Kathy broke the kiss and lay back on the bed. Marti crawled up on top of her and resumed their messy wet kissing. Marti's full curvy body in contrast to Kathy's slender almost body builder body was beautiful. Both were sexy in their own way.

Kathy seemed fascinated my Marti's big tits, which she must have seen the night before, but still she began massaging them. Spreading her fingers and putting her hands around Marti's full breasts. Marti began pinching Kathy's nipples, breaking their kissing.

The two women were now admiring each other's bodies. Marti partially sat up, straddling Kathy's slender waist, my cum dripping from her pussy onto Kathy's rock hard abs.

Marti looked questioningly into Kathy's eyes and I saw Kathy nod her head, "yes." I wasn't sure what it meant, until my wife slid her pussy up and sat on Kathy's face. There wasn't much left, but Kathy ate the remaining cum from Marti's pussy and then began licking her. Marti began to moan again. I couldn't believe it was happening so fast, but clearly my wife was going to have another orgasm. Kathy was squeezing Marti's ass cheeks as she licked Marti's pussy.

Marti's head was back. She was running her fingers through Kathy's hair when all of a sudden she grasped Kathy's head because it was all she had to hold onto. She rubbed her pussy hard into Kathy's face, but Kathy didn't flinch. She licked until Marti came down from yet another orgasm.

After only a few seconds of recovery, Marti slid back down Kathy's body and began to lick my cum off of Kathy's chest and abs. The whole time she massaged Kathy's tits and then her abs, appreciating the muscular build.

When she was finished, she looked up at me with a smile. Kathy smiled at me too.

I was still standing and watching, enjoying watching my wife with another woman, their two beautiful bodies on full view.

The girls finally got up with a final light kiss on the lips and a hug, quietly moving to grab their gym clothes so that Pete still wouldn't wake up. He sure was a sound sleeper or really good at faking it. I didn't bother to try to test him. I figured if he was faking it, oh well.

Marti, Kathy and I had our gym clothes on and snuck out the door.

Marti told me her version of the night before. She obviously hadn't known that I had spent time with Kathy. She told me how Pete and she had gotten started with some nice music, light kissing. She made him get up and dance with her, even though he wasn't really a dancer. They got in the shower and she got him hard. He fucked her in the shower. They got out and Pete seemed distracted as if something was wrong, but she wanted to get fucked again so she and Pete began cuddling again. They had to cuddle for close to an hour before Pete got hard again, not that it was punishment. Pete kissed her pussy again. That's when the door opened and Kathy came into the room. Marti said that Pete was just about to put his dick in her ass when Kathy walked in. Marti said that she felt like she had no choice, so she just let Kathy stay. She had Pete all worked up, but Pete said he had promised a Christmas Eve fuck to Kathy. He fucked Kathy, but couldn't get it up again after that. Marti was a little disappointed, but she and Kathy had a round of girl on girl while Pete watched. He still couldn't really get hard again even though both women took turns sucking his cock for a while. Marti said that she enjoyed sleeping next to Pete and she liked Kathy well enough that Kathy just stayed with them.

That's when Kathy spilled the beans about her plans. She was supposed to get Pete then go to our room and talk with Marti to see if Pete's plan was OK with Marti. I held her up and so she was way late. That was the first time Marti had heard about my encounter with Kathy. She was surprised, but happy for me. We all went to the gym and decided that it was Pete's fault for planning such an evening so we would just let him wake by himself.

I told the ladies about my experience after Kathy left and hitting five orgasms in one day and that I might not be up for so much sex today, it at all. We joked about the pressure that could put on Pete and Chuck. Marti said, "Or we might just have to find other guys if you three can't keep up." Oh, God, my wife was really turning me on. I could hardly believe it as she seemed serious. In fact, looking into her eyes, she was very serious. Her sex button had been pushed and apparently there was no easy way to turn it off.

We went to the gym and did our workouts. Marti pulled me aside briefly and said, "We have to talk."

"Yes. We do," I answered.

"You don't hate me do you?" she asked.

"No. Why would I?" I asked in return.

"I slept with another man on Christmas eve," she said. "I was sort of selfish."

"You know what I think about Christmas eve, right?" I asked rhetorically. "It's just another night. It was my gift to you. You were right before. This is a fantasy of mine. It's coming true. I wanted you to open up sexually and love the idea of you fucking another man. I just want to talk to make sure we are still a couple. It's clear you like Pete and have fun with him, but do you love him?"

"No way. No. I don't love him. It's just that this sex with someone else thing was so much fun and sleeping with him just is so different. I'm not sure what exactly I feel for Pete. It's a strong like, for sure, but it's not love. We can talk more later, but you're still my man. I'm just experiencing things and especially sex like I've never even thought I could, so I'm a bit overwhelmed."

"That's good to hear. It's sort of what I was hoping. We can take some alone time later and talk more, but I still want you too. Cheryl and Kathy are fun, but they aren't you."

I gave Marti a hug and gave her a kiss. She pushed her tongue through my lips to find mine. I tried to pin her tongue down with mine and she escaped. Her hands moved from my neck to my lower back and then she squeezed my ass.

"Hey, guys. We're here to workout. It you want to do that, go back to your room."

It was Cheryl giving us a bad time. She stood with her hands on her hips with her head tiled to one side. Her face gave away the fact that she was being silly. Her smirk then turned to a laugh as we looked at her.

I let Marti head off to her recumbent bike and I went to a treadmill to warm up.