Our First Time Sharing in Cabo Ch. 03

Cheryl got more soap in her hands and began rubbing my cock. She stared into my eyes daring me to get hard.

"I want you again." She said as she continued stroking my cock. She got on her tip toes to kiss me and pushed her tongue past my lips. I didn't resist and I did want to fuck her again before going to bed. I just didn't know if I could. I pinched her nipples. She squealed.

I was getting hard again, and Cheryl leaned her back against the wall and pulled me close to her so she could wrap her legs around me. "Fuck me," she said. "fuck me fast." She picked up one leg and wrapped it around my waist. Then she pushed up with her other leg and I was able to hold her against the wall.

I wasn't quite ready, but she was able to work my cock into her with her hands. I was hard enough at least for penetration. I did as asked. I inserted my cock into her waiting pussy lips and tried not to bash her head against the shower wall, but she kept telling me to go faster. My cock became harder and finally got to a full erection. I tried to be careful because I didn't want to slip. So, I had to slow down at least a little bit. She was really turned on and I thought she'd wake Chuck.

"Oh, yes, again. I know I'm going to cum again, Oh, god, yes, keep fucking me."

After probably ten minutes under the warm water and Cheryl's legs around me, I was rock hard, but couldn't cum. Cheryl on the other hand, went over the top again.

"Oh, my god, you didn't cum and I'm cumming, ah, ah, oh, thank you, oh."

I held her against the shower wall until she could hold herself up again.

"You didn't cum," she said with some disappointment.

"You get used to it when you are old," I said. "But you seemed to enjoy it anyway."

Cheryl smiled, "Yes, I did indeed."

"I've learned that I can give pleasure better as I'm not usually expecting to orgasm. I can get hard about three times as often as I can cum. So, between that and my fingers and my mouth, I can usually give Marti as much or more pleasure than she needs."

"I still want you to cum again before midnight."

We dried off and didn't put on any clothes. I wasn't sure about sleeping arrangements, but after that, I was fine sleeping in the bed next to Cheryl and Chuck. It was getting late.

We walked out of the bathroom and into the bedroom.

Chuck said, "Geez. Can't a guy get any sleep? It's almost midnight. Why don't you just try again, then go to sleep."

I looked at the clock. It was 11:40 and I didn't even know if I could cum at all, let alone in twenty minutes. Cheryl began kissing me and said, "Yeah, why not? That would be a record I could be really proud of. It might never be broken."

It was clear her competitive spirit was coming out. I agreed, but warned her that it might not be possible. I really wanted to do it for her. At that point, I was actually pretty worn out. I was feeding on Cheryl's energy at this point.

Cheryl continued kissing me and began to rub my cock. We got on the bed next to Chuck. I wasn't getting hard at first, but then I felt some stirring as she planted a finger into my ass hole. This might be one of those times when I cum without getting fully erect or I get erect, but don't cum. I wasn't sure which. It was 11:50 now and still I wasn't feeling like I was going to cum.

All of a sudden Cheryl said, "I'm really sorry. I Have to pee really badly. I can't wait any longer. She jumped off the bed and ran to the bathroom. I'll be back as soon as I can. Now, I thought it was futile and I'd just go to sleep.

As I was thinking my cock would go soft, I felt Chuck's hand on my cock. He continued stroking as Cheryl left off, then he went down on me. He began sucking cock like this was not his first time. It was incredible. He focused on the underside of the head of my cock and I knew I could cum now. Would I cum in Chuck's mouth? Is that what he wanted? That would tie my record, which I hadn't done in a few years, cumming in a guy's mouth?

At first those thoughts seemed odd, but I realized that I was really excited and really hard. I never thought I would do such a thing, but a warm mouth was a warm mouth and Chuck was a nice guy and he did give a great blow job. I was pressing on the back of Chuck's head. Chuck was trying hard to get me to cum. I was now rock hard from this new experience. Cumming was a different story. I wasn't even sure I had enough liquid in me. The clock was ticking and Cheryl wasn't out of the bathroom yet. I really thought I was going to cum before midnight now. I was getting close. This was hotter than I would have ever guessed. Cheryl ran out of the bathroom, not surprised to see Chuck sucking my cock.

She got on the bed with her ass in the air and grabbed the anal lube. "Put it in my ass. I want you to cum in my ass," she commanded. "I get the record cum."

I didn't want to pull my dick from Chuck's mouth, but Cheryl's ass was too inviting. Even if I didn't cum by midnight, I was going to ass fuck this little girl. I moved as quickly as I could and I shoved my cock in Cheryl's ass with just the lube that she had inserted there. I did not have time to lube my cock. I couldn't get all the way in at first, but she was so tight, it felt great and my dick didn't soften a bit.

I almost pushed Cheryl onto her face, but within a few strokes I was all the way in and due to Chuck's expert cock sucking, I was ready to cum anyway. The tightness of her little butt squeezed my cock and I couldn't help but have an orgasm. The best I could tell it was a dry orgasm. I know you young guys probably have no idea what that is, but it's when you are pushed over the edge, but no is released. Not that it happens often to me, but at times of multiple orgasm, it's not uncommon either.

She felt my body stiffening behind her and my final thrust was a push and hold. I held myself as deep into her as I could.

"Yes," she screamed. "Yes." She pulled forward, my cock slipping out of her ass, she swung herself around to face me and was on her knees kissing me before I could recover. We made out as my hands rubbed her ass and fingered her backside hole.

"I'm sleeping with the record holder," Cheryl said smiling at Chuck.

"Fine," said Chuck winking at her. "I just want to sleep."

Chuck went back to bed and Cheryl and I tried to be quiet as we were still on our knees covering each other in kisses. I explored her whole body again as if it was the first time touching her. Coaxed her into lying down next to me so I could kiss her from her forehead to her toes. I flipped to her other side and kissed from her toes to her head. All the while I caressed her smooth tight skin. When I finished, I pinched her nipples yet again.

"Make me cum one more time?" she said.

I responded by moving a hand to her pussy while kissing her. I stuck three fingers in her wet pussy. Her juices covered my hand. Cheryl closed her eyes and moaned. I found her g-spot and began rubbing. Once I knew I had it, I placed my other hand on the top of her mound and applied pressure so that her g-spot would be sandwiched between my two hands. I massaged with pressure on the top of her mound, essentially rubbing her g-spot from both sides.

Cheryl's eyes opened wide. "oh, my, Chuck's never done that before, you'll have to teach him. I guess that's one of the benefits of being an old man," she said and went back into her dreamy state with her eyes closed.

Cheryl writhed below my hands. Her hips lifted from the bed. Her hips met the pace of my rubbing on her g-spot. She was doing a hip bridge against my hand. She was fucking my hands. She was fucking them hard.

As she hit her orgasm, she tried to be quiet as to not wake Chuck. She whispered to me as her body was hurriedly thrusting against my hands, "Yes, oh, oh, I'm cumming, oh, oh, oh, so good. Thank you."

She rolled over and lay on top of me. She kissed my forehead over and over. Then she kissed my lips.

"Merry Christmas," I said. Cheryl just smiled and nodded her head and then rested her head on my chest. Within a few minutes she was sound asleep.