I swear I wasn’t trying to look, but I was starting to think Sheila Hannan was doing it on purpose. Every time I walked by my kitchen window, I’d see her out by her pool, dressed in a skimpy bikini that I had never seen someone her age wear before. The skin on her stomach was loose and wrinkled, and the bathing suit top did little to lift her saggy breasts.
Today was no different. It was a hot July afternoon, and when I was finished cleaning up after lunch, I looked out the window to see her throwing a towel onto one of the chairs by her pool. Suddenly, as she was adjusting her bikini top, the thin material came loose, causing a nip slip.
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My eyes widened. I briefly looked away, my cheeks burning red, but for some reason, I couldn’t avert my gaze for long.
What was wrong with me? This woman was a grandmother! She was the nice old lady who would occasionally bring me cookies and leftovers. It felt wrong or something to be looking at her like this, let alone to be getting turned on by it.
“Is she looking at me?” I mumbled to myself, unable to tell where Sheila was staring, thanks to her sunglasses.
To answer my question, she gave a little wave, and then motioned for me to come over.
“Donovan!” she said chirpily, as I went out the kitchen door into my backyard. “Did you want to come have a dip? It’s the perfect day for it.”
I walked closer to her. She pulled her sunglasses off and put them on the chair next to her towel.
“I don’t think so, but thanks,” I said politely.
I watched as Sheila shrugged and headed into the pool. I could have just turned back to my house, but I didn’t. I couldn’t take my eyes off of her in that red bikini. The skin on her ass was no longer taut and tight like it might have been forty years ago. It now hung a little bit like a deflated balloon. I stared as she lowered her body into the water.
“Come on!” she said, pushing her hands so they skimmed the surface. “Get in!”
“Um, I’ll have to go get trunks.”
“Nonsense,” she scoffed.
Within seconds, I found myself stripping down to my black boxer briefs and getting into the pool with Sheila. I couldn’t believe this was happening, but even more, I couldn’t believe I was enjoying it.
She moved through the water so that she was closer to me. Her wiry gray hair was pulled off her face by a headband.
“I see you looking at me, you know,” she said quietly, our faces an inch apart. “I. . . well, I like it.”
I swallowed. “I like it too.”
Then her lips were on mine. I was only twenty-seven years old, and here I was, kissing an actual grandmother. If I was supposed to have been embarrassed, I wasn’t. When I brought my hand up to her face, it felt different than kissing someone my own age. Everything about Sheila was less taut and soft. Her skin felt like creased paper.
I reached back to untie her bikini top, letting her breasts go free. I squeezed them in my hands. They felt empty and hollow. But they were strangely sexy to me, and when I ran my thumbs across her nipples, Sheila let out a soft moan. She was so responsive to me. I loved it.
“No one can see us back here, right?” I asked suddenly, looking around to make sure we were secluded.
She smiled. “Not a soul. Don’t worry. No one’s going to see you fucking the old lady next door.” We both let out a small laugh.
I felt encouraged now, moving my hand down the front of her until I reached her bikini bottoms. Sheila wrapped her arms around my neck, letting her body softly press against me in the clear blue water, while I pulled the bottoms off of her. She kicked her legs, releasing them from around her feet. She was completely nude now.
“I’m so glad you came over today,” she whispered into my ear, making my heart race even more. “Go ahead and touch me, Donovan. I know you want to.”
I reached between her legs to run my fingers across her clit. I had never messed around in a pool before, let alone messed around with someone Sheila’s age. It was exciting, and I loved the sounds Sheila made as I played with her pussy. She leaned against me, her body shuddering as she closed her eyes. We swayed in the water, her naked breasts pressed up against my taut chest, as my fingers moved faster and faster.
“Oh my god,” she groaned, her voice sounding more high-pitched than usual. “Donovan!”
Just like that, she was cumming, and it made my cock rock hard. I loved how she sounded, her moans coming out croaky and panicked from her throat.
She leaned against me for a minute after she came, her chest heaving against mine. When she pulled away, she lifted her chin up to kiss me as her hand slid down to the waistband of my boxer briefs.
As I kicked them off, she touched my cock for the first time, making me twitch.
“So big,” she said, looking into my eyes. Hers were wrinkled at the corners, years of squinting and smiling caught up to her. Somehow, though, I still found them to be beautiful eyes.
“You made me so hard to fast,” I said, our lips pressing together again. Our tongues slipped against each other’s, as she reached down to stroke my cock.
“Come over here to the edge,” she said, heading to the side of the pool.
I watched as the sun cut through the water, making her body appear glowing and rippled. When she was at the edge, her back to me, she looked over her shoulder.
“You know, in all my years, I never had pool sex before.”
I pressed up against her, squeezing her ass. “Mmm, me neither. Maybe we should try it out.”
And with that, I began to press my cock into her. It was strange here in the water, with no resistance, no tension, but it felt incredible all the same. I went slowly, as Sheila arched her back towards me, sticking her ass out like she was trying to meet my cock.
“You feel incredible,” she said breathlessly, letting her head drop back.
I smiled, even though she couldn’t see. “You do.”
With my hands holding onto her waist, I started to fuck her. It was so easy in the water, like we were just floating along. Her pussy was easy to fuck, with a grip on my cock that surprised me. We stayed like that for a few minutes, slowly and easily fucking.
“I want to look at you,” I said into her ear, leaning in to kiss her cheek.
So we changed positions, with Sheila’s arms and legs wrapped around me as I helped lower her onto my cock. It was easy to hold her in the pool, and I was able to put my hands under her ass to lift her up and down.
“Ooh,” Sheila whimpered, biting her lip as her eyes looked pleadingly into mine. “That feels. . .” she trailed off, and another moment later, she was cumming for the second time. I loved the way her pussy clenched against my cock.
“Goddamn,” I said, as a shiver ran down my spine. “I should have been doing this the whole summer.”
Sheila laughed. “I couldn’t agree more.”
We remained like that for a few minutes, with her slowly riding my cock as the cool water gently splashed against us, but then I couldn’t control it anymore.
I grabbed her waist, holding her so that my cock was buried completely inside her pussy, as my cock twitched inside her. I came hard, my whole body tensing up and shaking, my eyes locking onto Sheila’s. She looked turned on by the sight of me cumming. My orgasm felt like it would never stop as I flooded her pussy with hot cum.
When I finally lifted her up off my cock, Sheila let out a big sigh, running her hands through the water. We smiled at each other.
“It took you long enough to notice me,” she said teasingly. “I’ve been flashing my tits at you for weeks now.”
My jaw dropped. “I knew it was intentional! I didn’t want to assume anything, but I kind of figured.”
I reached out to pull her in next to me, kissing her mouth.
“How about we go upstairs and rinse off all this chlorine together?” Sheila said, giving me a playful look. “You’re not busy, are you?”
We quickly gathered up our clothes that had been left in the pool, pulling our bodies out into the warm summer sun.
“I always shower after a swim,” I said, following her into the house, watching her ass as she went.