Our First Time Sharing in Cabo

Day 7 -- December 29

What the fuck? I thought as I woke up. Cheryl had bit my nipple so hard it was red. I noticed a little blood where she had broken the skin.

"Well, you wouldn't wake up." Cheryl said as she looked into my sleepy startled eyes. "You ready to cum in my little pussy?"

Now, I was. I had a good night's sleep. I got up to pee and got a glass of water. Then I put on some coffee and came back to bed.

"Don, can you get me a towel from the bathroom, just a hand towel?"

I got up and got her a hand towel.

"oh, I forgot, can you get me the anal lube out of my overnight bag?"

"You want anal? I thought you wanted it in your pussy."

"Oh, I'm not sure. I just like watching you walk around naked." She laughed. "I love watching you walk away especially."

I turned away from her and gave my ass a little shake.

"Oh, my god. Get over here. I want that."

I lay down and she rolled me to my stomach and started kissing my thighs and my ass cheeks, then her warm wet tongue went around my ass.

"I love your ass, just in case I haven't told you yet." She said. She continued to lick and lick, then I heard a vibrating noise and I could guess what was next. She rubbed the little finger sized vibrator around my asshole. Then she moved it to the area between my ball sac and my ass hole. She put her tongue back into my ass hole. "Oh, fuck," I thought. It felt so good. I got rock hard almost in seconds.

"Mission accomplished," she said as she moved her mouth from my ass and rolled me over. She put her mouth down on my cock and continued massaging my perineum and my ball sac with the vibrator.

"oh, my god. That's about the best thing I've ever felt." I said.

She looked pleased with herself. "It's a little trick my momma taught me," she said.

"What?"

"My mom taught me some things that she said men would like. It's not like she did anything wrong. Lots of women have to start sex from scratch, but my mom thought I should know something if I was going to be sexually active. I wasn't overly promiscuous and my mom didn't want me to be. In fact, she didn't teach me any of that stuff until after I was engaged to Chuck."

What a mom, I thought. I just enjoyed from then on out, except I really thought I was going to cum with her expert cock sucking and the vibrator doing at me.

"I thought you wanted me to cum in your pussy?"

She put down the vibrator and let off of my cock. "I do." Without any hesitation she rolled on her back and pulled me with her. I rammed inside of her. I didn't let up and I fucked her so fast that I thought she'd complain, but she just rode with me.

"Come on, old man, you can do it. Cum in my pussy,"

So, I did. It was like three minutes. I felt great, but awful.

"That was so cool," she said. "Oh, my god. I made you cum so fast." She was excited. So funny how she always went after my pleasure. I wanted to go after hers, but it was fun.

"OK, thank you," I said, "But now it's your turn to cum. Or let's try to make each other cum together."

"OK, Old man," she said. "I'm up for it. How about you? Can you do it again?"

I told her I probably couldn't, but I'd try, and she reminded me that because of all of the activities that have gone on, she hasn't been able to work out like normal so she wanted to make sure we got to the gym. "So, let's make it quick."

I tried so hard to get her to cum fast. I got two pillows under her ass to raiser her butt of the bed. I drilled into her. With her pelvis raised it also made it so I could be on my knees driving into her and it freed my hands to play with her thighs and pussy. I drove into her.

She laughed and said, "Wow, this is great. I get to look at your pecs, get a big dick in me and get my little bud pleasured. I'm definitely going to cum fast. Bet I beat you."

I drove hard into her on that. The good news is that I pretty much controlled the pressure on her pussy and I knew I probably couldn't cum again anyway, so she would win. I would win because she would win. The one thing I really couldn't tell is that this angle gave extra stimulation to her g-spot if I got it right. So, I had no good idea of how much stimulation she was getting from that. I noticed her face flushing a little so I knew it was building. I rubbed her bud more quickly with just a little more pressure. She closed her eyes, "Yes, just like that," she said calmly, but short of breath. "Oh."

Now I knew she was going to cum soon. "Oh," escaped her mouth again. She still had her eyes closed. She then looked up and smiled as best she could. "l love your pecs. Did I tell you?"

I continued ramming her, rubbing her bud and trying to hit her g-spot every time I rammed inside of her. "Oh," escaped her mouth yet again. Now, she had her eyes open, examining me.

"Cum for me baby," she said softly. "Cum in my little pussy."

"are you ready to cum too?" I asked.

"Ye-es," she said. "Ye...es, ye...es, I...am...rea...dy...to...CUM." Her body shook and my cum released as her pussy shook my cock and her muscles tightened on me.

"Are...you...cum...ming?" she asked as I was in the middle of my release. She had to know I was.

She laughed. "That...was...great." She was still trying to catch her breath. I licked the cum from her pussy then held the hand towel so she could catch whatever she wanted.

"Bring me some," she said.

I scooped some of my cum with my hand and brought it to her. She slurped it up.

"HMMM. My pre-workout shake. I should suck your cock to get more."

I told her she had done enough for me for now.

She lay there for no longer than five minutes, when she popped up and said, "We need to get to the gym."

I watched her tight ass as she wiggled into her gym shorts and put on her sports bra. I thought about how lucky I was to have a friend like her.

Not strangely, no one else was at the gym that morning, not even Kathy. I mean, there were other people, but no one from our group. I enjoyed the time watching Cheryl without distraction. I did get my workout in, but with us there alone, I saw how disciplined she was and of course how lovely she was. She inspired me and I worked out really hard as well. We didn't do all the same exercises this time and we didn't follow each other around the gym, but being there with her alone was nice.

"Hey, sexy old man," she had come up to me from behind. "You have a pretty nice ass."

I told her I had been thinking about the same thing and how much I enjoyed being there with her alone. I also thanked her for requesting to spend the night with me.

"Hey," that was what I was going to say," she said. We laughed and hugged each other. We went back to our workout and back to the room to shower. I needed my post workout meal, so I ate her pussy before taking the shower. I suppose I've mentioned how much I like a sweaty woman. I love eating sweaty pussy too. We showered, put our some shorts and shirts and headed over to breakfast.

We were also the first ones to breakfast. It gave us some additional alone time. I figured with some of the pairings last night that it could be an odd breakfast. Pete and Jennifer joined us next. They both looked pretty pleased. I thought for a moment that with Jennifer's appetite that Pete might not have been able to satisfy her, but I figured it was none of my business, especially as they both looked happy.

"Oh, my god," Jennifer said. "Pete is so funny. We had so much fun."

We talked in generalities, but I gathered that they talked had some sex and then it sounded as if they watched a comedy of some sort that I'd never heard of then got a good night sleep and perhaps had sex this morning before coming to breakfast.

Cheryl related more of our evening than I thought appropriate as she talked with Jennifer, but what the heck, it wasn't as if we didn't know a lot about each other's sexual preferences at this point.

Brian and Jackie and Joe and Sarah came in next. With them being the only non-swapping couples that night, I figured they'd be in a little earlier than the others. Come to find out, not a lot of details, but Jackie had definitely saved some for Brian and Joe. Evidently, they went back to their own rooms, but when they realized that they were the only two couples not swapping, Sarah texted Jackie with a simple text, "Swap?" So, after fucking their own husbands, they switched rooms for the night.

Jack and Kathy were next. They didn't say much. That fit their personalities. But by their demeanors, we could tell that they enjoyed their evening together as well. I also gathered that because Kathy didn't come work out, Jack and she had probably done more than sleep in.

Chuck and Marti were last. I had saved a seat next to me for Marti, and as it worked out the only seat available was next to Marti's and Cheryl couldn't easily switch seats without breaking up the couples. Marti looked tired and simply told me, "Chuck didn't lie. He kept me up all night. He can keep it hard like no one's business. He's as good as those college guys." She wasn't complaining, but she was tired. She said she did get about two or maybe three hours of sleep. The only other piece of information was "I think he fucked me about five or six times. I can't really remember, and then between times he ate my pussy like three times. I'm so happy and so sore at the same time."

We finished breakfast and no one talked about having more sex, except for Cheryl. She whispered to me, "It sound like everyone else is worn out. I'm up for more." She just stared into my eyes. This little one was back to being a fireball. I told her that she might have to find someone else as I was probably done for now and from what Marti had told me her husband was probably worn out as well. We all agreed that we should probably go back to our rooms with our own partners for now. Pete and Kathy would go back to their own rooms to get ready for the day.

I wanted to do a lot of photography. We had another boat tour on tap for the afternoon. Some of us wanted to hang out by the pool and on the beach to play volley ball. So, we set the day, our final full day, in Cabo roughly like this for now, but with some ability to play it by ear if necessary.

First, some relaxing private time this morning and people could do what they wanted.

We'd all meet for lunch together again, if we could, but no real obligation, just let others know and so we all swapped cell numbers for today and future reference with those we hadn't shared with yet.

After lunch we'd all hit the glass bottom boat tour. I'd make sure I got time to photograph something besides bedroom activities, which caused people to wonder what I'd shot so far.

We'd be back before dark, so we'd probably get on a bus and go to a beach farther away that we hadn't seen yet.

Dinner would be at a local nicer, but still non-touristy, if possible, place.

Dancing had been fun, but we were trying to think of something else to do after dinner. No one popped up with an idea that everyone liked so we decided to wait until later. Of course, someone had to say something like "If we can't think of anything else, we can always go back to Chuck and Cheryl's for another gangbang."

We all laughed at that, although a few of the women smiled at each other. Looking around, I think that everyone had the same feeling that I did. We certainly hadn't exhausted all combinations. On the other hand, we might need a day to recalibrate after so much that was new for all of us.

Back in our room, Marti said that she was exhausted and wanted to nap. I said I understood and that I think I'd play some volleyball with Brian, Jack and Joe.

Arcella came in to clean the room and didn't even knock or call out "housekeeping" this time. I wanted to stay, but I had already mentally committed to playing volleyball and Marti was going to nap, so the bed wasn't available. Arcella just smiled at me and didn't make any moves or say anything as if she were coming on to me, so I figured I'd just go.

Since Jackie, Sarah and Jennifer all played, I'd make seven, but we could work it out so that we could play 3s and one person could sit out a game or we could play doubles and rotate in teams.

They volleyball court was open and so we took it over. There were other courts so we didn't worry about anyone cutting in. Bill came over and asked if he could play. Turned out that he played in high school and was pretty good. He didn't get an offer from the college he attended and the colleges who were interested in him either didn't offer enough scholarship money to make it worthwhile or they were schools that didn't have his major. He sat near Jackie, surprise, surprise. Greg sat down to watch the rest of us play. He didn't play. We started with doubles and Sarah and Jack were playing Jennifer and Brian. Joe, Jackie and Bill sat together talking. Greg sat with me and I told him that Marti was sleeping because she had been up all night. He told me again that he was sorry about being a jerk to me. I told him that all was forgiven. I told him to just be careful because not all husbands are as understanding as I am. He got it. I also explained to him why I sucked his cock.

"I'm not gay or submissive," I said. "A lot of guys probably don't get that. I don't think I would have gotten it a week ago even. I've never sucked a cock before earlier this week."

"Really," he said. "Because that was really great. I didn't want to say it in front of my friends. And that's probably one of the reasons I was kind of a jerk. I was showing off. I just got nervous and didn't want my friends to think I'm gay or something."

"Yeah, well, I won't go through all the details, but I'm not really all that attracted to men, but I found that it didn't turn me off like I thought it would and it's just a cock. Well, I tried it and it was OK. I'm not passionate about it, but in the moment, I saw your cock and how big it is and I just thought, if I don't try it, I might never see a cock that nice again, so I did it."

"I get it," he said. "I know I acted all tough or whatever, but it actually turned me on that you did it. I don't think I'm truly bi either, but I actually think I'd try sucking a cock if it was the right guy and I knew people wouldn't make fun of me. Even if it was just once. I think I'd even try anal sex."

I was shocked. "Are you serious?" I asked.

He looked afraid, "Why? Is that bad?"

"No. it's just that I had anal sex this week. It was sort of unexpected, but I liked it more than I thought I would. I get why women like it, especially if there is someone playing with my dick while I'm fucked in the ass."

It was his turn to look at my funny.

"I meant to fuck a guy in the ass, not be fucked in the ass." He thought for another moment. "Well, I guess you're right. I mean your wife loved it even with my huge cock hurting her."

"Right," I said. "You know what else. I think it might make me a better anal lover with women because now I know what if feels like. In fact, while you were fucking my wife's ass, I was sort of hoping you'd fuck me in the ass so I could know exactly what if feels like. That may seem odd. Like I said, a week ago, I wouldn't even have considered it. I guess I would say that I appreciate men, but I LOVE women. That doesn't mean that I can't have sex with a man."

Greg thought about what I said. "Would you have sex with me?" he asked.

"Are you asking hypothetically, or are you asking me to have sex with you.?" I asked in response.

He looked as if he wasn't sure. "I guess I'm asking you to have sex with me. You let me have wild sex with your wife. I can trust you. You seem like a nice guy. If I'm going to try sex with a guy, I can't think of anyone else. I'd do it with Bill, but I'm still not sure if I can trust any of the guys my age, and I'm not ready to admit that I want sex with a guy yet. I'm guessing some of them have had bi sex, but the guys I like or would trust haven't mentioned it. So, yeah, Don, will you have sex with me?"

"Here's a question for you, Greg. I just thought I've watched my wife do a lot of stuff this week, even girl on girl. She has not seen me with a guy. She really likes you and your huge cock. Would you be willing to have sex with me in front of her?"

"Wow. That sounds kinky, but I think I might. Can I think about it?"

I told him it wasn't a problem and if he changed his mind entirely that was fine too. It was my turn to play some volleyball. I chose Jackie as my partner so she wouldn't make too much of a scene for herself making eyes at Bill here on the beach in front of her husband. I realized that Brian now allowed her to have sex with Bill, but I didn't think he or she really wanted to cause a public scene. Brian and Jennifer won, so they stayed on. Jack and Sarah came off.

Brian was a lot taller than I was so Jennifer and Brian had the advantage. We could always just choose to serve Jennifer, but that seemed unfriendly. After all, this wasn't the Olympics. Jackie was a good hitter and my setting was good. Just due to my height, I'm not a great beach hitter. At 5' 9" and 57 years old, I have an OK vertical for my size and age, probably around 24 inches when I last measured it, it's still not great. I've played for 45 years now, so I mostly rely on control and experience. It was close and the game was taking forever. Thank you for rally scoring to make things a little faster. I still remember the old days when games would really take forever with side outs. It was 20-19, with Brian serving and our team losing, when Brian served me and at the same time I realized that Greg was missing from his towel. The serve hit me in the hip.

Brian called out, "hey, sorry. I thought you were ready. I'll replay."

I was ready to give up the game, but Jackie was hearing nothing of it. Her competitive side came out against her husband.

"Replay," she said. All I could think about was Marti and Greg. I'm sure that's where he went. My head just wasn't in the game.

Brian served his wife this time. Jackie gave me a perfect pass, but I set it a couple of feet off the net. She was a bit under it and had to hit a roll shot. Unfortunately, it went straight to Brian. Jennifer gave him yet another perfect set, and I went to block, but he tooled me and the ball came down on our side.

I began to walk off when Brian called, "Hey, we're off. Max of two wins, right? Besides, that's all I can take."

"Nope. Next four." I called back. "Bill and Sarah against Jack and Joe."

Glad I thought of it. As Bill passed me to get on the court, he winked at me. Now, I knew where Greg was. I walked the short distance to the pool area, through it and to my room. I opened the door and heard, "Oh, god, yes, fuck me" and then saw Greg just about jump off my wife.

"Sorry, man. I couldn't resist."

I told him it's OK. I just wanted to check to make sure he wasn't raping my wife because she was tired and wanted to sleep.

"It's fine." She said. She wasn't that convincing. "yes, I need my sleep, but one fuck isn't going to hurt. I'll go back to sleep as soon as he's gone. Come here, baby, fuck momma with that big cock."

She pulled Greg back to her. Greg continued his fucking.

Within a few strokes she was moaning again. "Yes, fuck me with that big cock. It's so big, so good. Cum in my pussy you huge boy." Two things were clear to me. One was that she was enjoying that big cock stuffing her, but she also wanted to sleep. I know when my wife is really tired.

Greg continued to pound her into the mattress and force his huge cock into her pussy. Her pussy seemed to swallow his cock with each thrust. "oh, god, so good, so good, so good," Marti kept repeating. She wanted to enjoy this fucking, but she was just too tired to do more.

"Ah, fuck," shouted Greg as he came. He spasmed and then relaxed inside my wife.