There were still a dozen or so of the old gang left hanging around. Most of us had graduated college. Quite a few had moved away for jobs. Many were married. Some had children. There was even a divorce or two. We were all in our mid to late 20’s. We would occasionally get together usually at Denise’s house. Actually, it was her parents’ house. Denise still lived there, since it was really a mansion. Dad had inherited money and was a high-power lawyer. Mom sold real estate when she felt like it. Denise had her own wing, so privacy was not a concern.

Dad and Mom were on a two-week vacation in Hawaii celebrating their 30th anniversary. Denise planned a pool party. Denise wasn’t concerned about any of us trashing any of her folks’ things. We all knew her folks, respected them and even liked them. We would clean up after ourselves. It was a beautiful pool, and we were all looking forward to it.

There were 13 of us this night, seven girls and six boys. No one was really attached to another. There was plenty of food and drinks. Once it was dark, Jack (yes, Jack the jock) had the idea we should go skinny dipping in the pool. Jack cajoled everyone into doing it. I think I was the last one. I have a modest package, even more modest when flaccid. You guessed it, Jack had a monster cock. Once I was undressed, Jack pointed and started to giggle. The girls looked but politely turned away acting like there was nothing to be bothered about. The rest of the guys tried to remain calm but giggled a bit.

I had my fill. “Now wait a minute. Yes, I admit I have a modest package.” Yes, that got everyone’s attention. “However, there are advantages. We’re all adults here. Well, at least most of us.” I looked at my “friend” Jack. “Let’s remember that size of the penis doesn’t equate to female sexual satisfaction. I shouldn’t speak for the fairer Sex, but I’ve read that most women don’t climax from vaginal intercourse. Tongues and fingers (and even toys) do the trick quite nicely. Since we are adults, we might at some point want to try some sexual experimentation. For example, Anal Sex. If you are an Anal virgin, would you like a monster cock to be the first to invade your delicate bottom?” I said as I pointed to Jack’s package “or would you prefer a more modest package. Actually, do you even want a monster cock to invade your lady parts? If any of you would like me to help in your sexual exploration, just let me know.” Hardly were the words out of my mouth when Ashley raised her hand.

“Ashley, do you have a question? Just speak up.”

“I don’t have a question; I want Anal Sex.”

“Well then, I’m your man. Just let me know when and where.”

“Here and now” she stated.

“Well, uh. I guess Denise can let us borrow a bedroom.”

“No, I mean right here, right now.”

“Ashley, are you drunk, have you been drinking?”

“No, I’m stone-cold sober. I don’t drink.”

“Well, uh” I stammered.

Too late, Jack (what a surprise) started the chant “do it, do it, do it.” I guess I should be happy they weren’t yelling “fuck her in the Ass, fuck her in the Ass” I guess even Jack knew this required a bit of sensitivity.

I was cornered. “OK… We’ll give it a try.” I was a bit worried I couldn’t get an erection. “But there are rules. First of all, Ashley is in charge. If at any point she wants to stop, it all stops immediately. No one, and I mean no one, says anything. She gives me directions about anything she wants done, like slower, stop for a moment. Second, no photos. Everyone, stack your cell phones over here.” I did a quick count, and I was one short. “Oh wait, I forgot mine.” I quickly remedied the situation. “Third, Ashley and I are going to have to focus on Ashley’s pleasure. So, no distractions. No talking, no chanting. Nothing. Denise, please dim the lights, so Ashley and I can try to forget you are here.”

“Denise, I need a condom and lube, lots of lube.” I barely had the words out of my mouth before Denise lifted a cushion storage chest and brought a roll of condoms and a container of lube. Hmm, it seems this wouldn’t be the first time someone had Sex in the pool area.

“I need a bunch of cushions here for us to lay on.” Surprisingly, the girls had gotten into this and arranged cushions in about the size of a king-size bed. I guess you don’t get a chance to view live Porn, even amateur, every day.

“Ashley, the best chance for you to have a pleasurable experience is not to jump immediately into Anal but to begin with foreplay, lots of foreplay. OK?” Ashley smiled and nodded. “Are you sure you want to still do this?”

“Oh, hell yeah!” She was ready.

Ashley and I moved to the cushions. Everyone else moved back into the shadows. We started to kiss. I ran my hand through her hair. Ashley is a great kisser. As they say, “our tongues danced.” I moved to her neck and kissed her. I could tell that was doing nothing for her, so I moved to her left breast, kissing and licking. I took her nipple between my lips and sucked.

This Ashley liked. “Bite me gently, baby.” Oh yeah, she liked this. I kept it up and then moved to her right breast, tweaking her left nipple with my thumb and index finger. Ashley had her hands in my hair and started to push me down. Smart guy that I was, I knew what she wanted. I kissed down her tummy, moved to her inner thighs, and licked some more. I slowly moved up to her lady parts. I kissed and licked her outer lips before moving to her clit. She was really pushing my head into her now. She was very wet. I slipped two fingers into her Pussy and started rubbing her G spot. It didn’t take long. Ashley was a squirter and didn’t disappoint.

I whispered in her ear: “Ashley, do you still want to lose your Anal virginity.”

“Oh, fuck yeah. Do me, Baby.”

“Get on your hands and knees.” I reached for a condom, but Denise beat me to it. She tore the wrapper off, pinched the tip, and put it in her mouth. She bent over, grabbed my dick, and slipped the condom out of her mouth onto my erection. She then dripped lube on it and used her hand to spread it around. She took more lube and gently filled Ashley’s anus. Denise then went back into the shadows.

Ashley reached around to put the tip of my cock at her anus. “You’ve gotten bigger since you got hard.”

“Yes, I have. Do you still want to continue?”

“More than ever. Just go slow to start.”

I pushed in just a little.

“Wait a moment right there. Let me get used to it.”

I’m good at following directions and didn’t move forward until Ashley gave the OK. I slowly moved my cock into her anus until I was all in. “Wait a moment, Baby. I want to remember this. OK, now fuck my Ass slowly at first.”

I moved in and then out. Ashley put her right hand on her clit and started to rub. “OK, Tony, fuck me now.”

I started to fuck her. I bent over and pinched her nipples. “Faster Baby.” Ashley soon started to cum again, squirting even more.

I couldn’t hold back any longer, and I started to cum. When I was done, I bent over and kissed her shoulders. I slowly pulled out and let Ashley lay on her side. I kissed her lips and stroked her shoulders. “Thank you, Ashley. That was wonderful.” Denise handed each of us a bottle of cold water. What a perfect host.

“Oh, Baby. That was great. I can strike two things off my bucket list — Anal Sex and Sex in public. What do you want to try next?”

I was shocked by her question but started to give it some thought. I didn’t think this would be the last time we would be together.

Ashley slowly got up and put a robe on. Everyone seemed to have forgotten about skinny dipping and got dressed. The party was breaking up. Nothing was going to top our display. Denise returned to us after everyone else had left. We were both a little worn out, but we were reviving.

Denise said, “Don’t you two go anywhere. The three of us can spend the night. Maybe, Ashley can strike something else off her list.”