Nude in My Girlfriend's Pool

After a day of naked fun in Lindsay and Ron's pool with my friend Debbie (see Nude in My Girlfriend's Pool Pt. 2), I waited until the very large quantity of wine we both had consumed had worn off (at least for me) before driving back to my place. Night had fallen by then and Debbie was still pleasantly drunk, so it didn't take much convincing to get her to leave her clothes at Lindsay and Ron's and take a short naked car ride home with me.

Since Debbie's husband was overseas on business, I thought it better for Debbie to spend the night on my couch instead of driving home. Since Debbie passed out on the couch as soon as we walked in the front door of my house, I didn't find out how she felt about my decision or any of her feelings about what she had done during that day.

Although she was married and in her late 40s, Debbie still had a wonderful figure, with great legs, a full bosom and a dancer's butt. But she was still somewhat of a prude. So, I wondered if she'd ever, in her entire life, gotten totally drunk, taken off all her clothes out doors, masturbated, gone swimming and then spent the night on someone else's couch. I imagine that was a lot for her to take in.

I propped her head up with a pillow, covered her with a lightweight blanket, turned off the lights and went off to bed. The next morning, I woke up at my usual time feeling well-rested and refreshed, without the slightest trace of a hangover. I tiptoed nude past Debbie, who was still asleep on the couch, and into my kitchen where I made a pot of coffee. When it was ready, I poured myself a big mug, went into my home office, and logged into my computer to check my email.

As had happened the last time I'd gone over to Lindsay's house, there was an email from her with a private link to a video. Ron had once again uploaded the security camera footage from his pool area. But before I had a chance to click on the link, I heard Debbie moaning something along the lines of "oh, my aching head." A moment later, she was standing in my office, her nude body wrapped in the blanket I had used to cover.

"Is that coffee?" she asked, her hand pressed agains the side of her head as if to keep her brains from falling out.

"Good morning!" I said, cheerfully.

"Shhhhh! Quiet!" replied Debbie.

Debbie gently took my mug of coffee from my hand. She took a long drink, struggling to keep her blanket around her. Finally, not spilling her coffee won out over modesty. She was standing there in the nude, just like me.

"I'm happy to see you've joined my clothes free club," I said.

Debbie pulled up a chair next to mine, crossed her legs, and drank more of my coffee. "Have you seen my clothes? I did have clothes when I got her yesterday, didn't I?"

Obviously not remembering anything from the day before after the drinking started and not believing a word of what I told her about how she'd gotten totally drunk and nude in my girlfriend's pool, I chose that moment to click on the video link and spare myself the rest of the explanation.

Debbie nearly spit up her coffee when she saw herself nude and masturbating on a lounge chair in broad daylight. I made sure she heard the part where I said, "You do know you're being watched and recorded," and she replied, ""Who cares? I don't know them."

"What am I going to do?" asked Debbie. "What if my husband sees that? Or my children?"

I rested my hand on her bare knee reassuringly. "You have nothing to worry about. Ron and I have a little secret he knows I will reveal to Lindsay if he ever shows that video to anyone except me or Lindsay."

Debbie let out a sigh of relief, uncrossed her legs, and casually started fingering her clit. I noticed that she generally seemed more relaxed. "Gawd, that's such a turn on to watch!" she exclaimed. "I've never done anything like that before. I mean, I was naked. Outside. Drunk. And masturbating when I knew someone could be watching." She drained the rest of the coffee mug and added, "I've taken a giant leap this weekend." And then as a sly smile came over her face she said, "So, what do you have planned for us for today?"

All I could do was smile. It seemed as if Debbie had experienced a sexual awakening - and all because of me! Now, the question was, how far would she go. "We're going back to Lindsay and Ron's to get their mail, check on the place and use the pool. I'll tell you all about it when we get there."

Debbie wrapped the blanket around her and casually headed for the door. I threw on a t-shirt but no undies, grabbed my license and keys and was right behind her. We drove to Ron and Lindsay's, got the mail, and went inside - where Debbie found her shirt, shorts and bikini neatly folded on the kitchen table. "So, that's where I left my clothes," she said.

"Put your shirt and shorts on. You won't need the bikini," I said.

As if in a trance, Debbie put on her clothes. Her nipples were hard and clearly visible through the shirt. Her hand casually dropped between her legs and she stayed rubbing herself again.

I told her I had texted Tom, a guy I knew from Club Jack, a place where I worked when I was in college. Club Jack was a "no touching" club where worked in the nude as a "hostess" and chatted with men while they jacked off. It was a good way to make money without doing very much and at the time, I desperately needed the money to pay for college.

Tom and two other guys, Bill and Mike, were on their way over. I told Ron they'd be coming over and he didn't mind because he knew all three of them from Club Jack. The only one who didn't know about Club Jack was Lindsay. And that was the secret Ron and I shared.

Just then, the doorbell rang. I told Debbie, "Follow my lead."

We greeted Tom, Bill, and Mike at the door. All three were men in their mid-fifties, all generally in good shape, and all married. "This is Debbie," I said, introducing Debbie to the guys. Tom took Debbie's hand and kissed it. Bill and Mike simply shook her hand politely.

"Let's all go sit by the pool," I said. I handed Debbie a bunch of towels, grabbed a couple of lukewarm bottles of water from the pantry, and followed everyone out to the pool. We all sat around on towels and chit chatted for a few minutes - Debbie and me on one lounge chair and the three guys in individual lounge chairs. After a bit of listening to the men complain about how hot it was getting, I took my bottle of water and poured it on my shirt and shorts. The material became almost see-through and now my nipples and hairless pussy were visible for all to see. Debbie followed my lead. The guys' faces lit up as the warm water from the bottle revealed her huge aureolas and the landing strip between her legs. Before you could say "perky nipples," Tom, Bill and Mike had removed all of their clothing and were sitting on towels on their chairs fully nude, stroking their cocks.

I could see that Debbie was still in a bit of a trance as she watched three mature men masturbating in front of her. While the guys continued to stroke, I pulled my top off over my head, letting my breasts fall free, and slipped off my shorts. I sat back down next to Debbie, opening and closing my legs to give the guys a better view. They stroked faster.

Debbie had a wide-eyed look on her face and she couldn't take her eyes off their cocks. I bent down in front of Debbie to pull off her shorts, giving the guys a clear view of her naked pussy and a nice look at mine from behind. Then, I sat down behind her on the lounger, gently removing her shirt by pulling it up off her now-raised arms and over her head. I began to massage her neck and shoulders, never losing eye contact with the guys, who were really getting more and more aroused by this.

So was I. And so was Debbie.

Debbie was now making little circles on her clit with one hand and playing with her nipples with the other, alternately rubbing each breast with her thumb, increasing in speed as more time passed. I sat down next to Debbie and did exactly the same thing. The guys had big smiles on their faces.

A short while later, Debbie moaned with pleasure. Tom, Bill and Mike shot their loads onto their towels. Debbie and I stood up. I took her by the hand, and we both jumped into the pool. A moment later, the guys joined us. We all swam around in the nude for a few minutes before I let the guys know that it was time for them to dry off, get dressed, and go home.

Back in the house, Debbie and I wore only towels as I walked Tom, Bill and Mike to the door. They thanked us for a fun time. Alone a few moments later on the patio and still nude, Debbie and I sipped chilled wine from the fridge. Debbie said she this was a "freeing" experience for her and that she really enjoyed herself. That sounded like an understatement to me.

I opened an envelope and handed Debbie six $100 bills, which was half of the money Tom had given me on his way out the door.

"What's this?" she asked. "Your share of our tip," I replied.

"Tip?" Debbie was genuinely surprised. "Six hundred bucks for sitting around in the nude for an hour and watching three guys jack off?"

"Well," I chuckled, "We did masturbate for them." Debbie said, "True." She tool a long sip of wine. "But I enjoyed it, too!"

We clinked our glasses and finished the wine that remained in them. I poured us both another glass and said, "Oh, I almost forgot. Bill said Tom told him he'd tip $500 next time if you would let him cum on your breasts."

Debbie almost spit up her wine. "Seriously?"

I nodded. Debbie took in a deep breath and let it out slowly. "Well, let me think about it," she said. Then, she pointed to a security camera. "I guess we gave Ron a good show."

"Nope," I said, smiling slyly. "I turned off the cameras when we got here."

We clinked glasses again and drank some more. Debbie looked at her now empty glass. I refilled it for her. "You're trying to get me drunk again."

I just smiled, put down my wine glass, waded into the water and swam nude in my girlfriend's pool.