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My friend Keith’s mom has a book club — a quartet of attractive, forty-something women who drink Chardonnay and cackle loudly about filthy books.

They’re over at his house every few weeks. They’ve read everything from the Kama Sutra to a dominatrix memoir to romance novels. Keith finds it uncomfortable. I think it’s hilarious.

We both recently started college. I’m 19, but I haven’t lived a particularly sheltered life. I lost my virginity to my middle-school girlfriend and have gotten lots of action since then. But one thing I had never done — even though MILF porn really turned me on — was sleep with a much older woman.

So you can understand why thinking of four hot moms talking about sex as they got buzzed on wine was a bit distracting. Since Keith’s mom Jill is one of these MILFs, I hadn’t confessed this to him, but I fantasized about the scene a lot. What if I just walked in there naked, offered up my services, and watched what happened?

Well, the other day I was hanging out at Keith’s place when the book club convened. We were listening in from the kitchen as they discussed a sex-filled romance novel. During this eavesdropping, Keith got a phone call. His girlfriend’s car had broken down, and she needed help.

I offered to go with him, but Keith said no. By the furtive way he responded, I figured his girlfriend saying “My car broke down” was code for “Let’s have sex,” so I let it go. He told me to finish our takeout dinner and leave whenever.

I happened to be feeling pretty good about the results of a lot of gym work in recent months, which helped me walk with decent confidence into the living room where the book club was meeting. The women were sprawled all over the couches — tattooed Carol-Ann, curvy Lisette, foul-mouthed Olive, and mind-numbingly hot Jill. One Chardonnay bottle was empty, and another would be soon. When I appeared, they all stopped talking and stared at me.

I casually took a seat on the sofa near Jill, even though it was hard not to feel awkward with them staring at me. “So what are you discussing today?” I asked.

“Oh, you know,” Olive said, winking at me. “Threesomes, foursomes, gang bangs.” The other ladies collapsed into giggles.

“Oh, yeah?” I asked, playing it cool. “Any of you have experience with those things, or is this all hypothetical?”

Carol-Ann traced a finger up Lisette’s thigh. “Actually,” she said, “we were all in the same sorority. So yes, we got freaky a few times.”

This was excellent news. Apparently they’d all slept with each other in college.

“Please, Carol-Ann,” Jill teased. “Don’t traumatize the boy.”

I gave her my best smile and subtly flexed my biceps.

“I’m not a boy anymore, Jill,” I said. Then, in a move so bold I could hardly believe myself, I looked her up and down and licked my lips.

“Jill, I think that young man is offering you something,” Olive said, draining her wine glass and pouring another. The others stared raptly as Jill flushed under my gaze.

“Not just her,” I said, deciding to go all in. “I have no practical experience with group sex, but I’d love to learn.” I winked.

There was a moment of appalled — or intrigued? — silence, and then Olive burst out laughing. “Well, shit,” she said. “I’m in. It’s been a while since I had some nice, young cock.”

“Me, too,” Lisette said, leaning over to squeeze my bicep appreciatively.

Carol-Ann got up and straddled my lap, then started kissing my neck.

Jill had her hands over her face, but she was watching through her fingers. I rocked my dick against Carol-Ann, who moaned, and Jill blushed again before throwing her hands down.

“Not a word of this to Keith,” she stressed, understandably, and moments later she was cuddling and making out with Lisette on the couch next to me.

I got to kiss all of them in the living room. They also all kissed and groped each other. Apparently, sorority girls never forget how to get down, because within a few minutes, Olive was fingering Lisette on the couch while Jill kissed her. I felt like I was in heaven.

Eventually, we took things to the bedroom. Jill was divorced, so there was no husband to worry about — just a king-size bed and a nightstand full of toys. Jill brought out three different vibrators, then pulled restraints out from beneath the mattress. They were black with padded cuffs that attached to both wrists and feet.

To my surprise, the cuffs were apparently intended for me. The ladies escorted me onto the bed, then stripped off all my clothes and tied me up. I asked them to skip the blindfold, because there was no way I was going to miss seeing my MILF fantasy come to life.

Then they all got naked. Their bodies were so sexy. I’d never been with a woman who had cellulite and a tummy and all those supposedly “bad” markers of age. These ladies looked womanly, and something about all those curves made me want to fuck them blind. It was like seeing classical fertility goddesses come to life.

Jill crawled over me first. Seeing my friend’s mom like this — naked, with her breasts swinging over me and her mouth red from kissing another woman — was beyond hot. My dick was incredibly hard, and it stood straight up off my belly. Jill grabbed it and started pumping, rubbing her crotch on my thigh. I was shocked at how wet she was — she was practically dripping as her pussy ground into me, smearing her moisture over my skin. I lifted my leg as much as the restraints allowed, trying to rub against her.

Olive placed a hand around my throat and held me down. “No moving,” she said. “We’re going to use you.”

“Fuck yes,” I said. I’d imagined doing them all one by one, leaving them happy and satisfied, but instead it looked like they were going to do me one by one. And yup, I was down for this.

While Jill rode my thigh and Olive gently choked me, Carol-Ann bent over the bed and sucked my dick. She took it deep, bobbing up and down and following the motion with her hand.

Older women were incredible, I decided. I was never going to fuck a young woman again.

Jill was grinding hard, and I was torn between focusing entirely on Carol-Ann’s mouth and fixating on Jill’s pussy and what it would take for her to come. The final member of the party, Lisette, reached out and squeezed Jill’s nipples while she rode me, and it wasn’t a gentle pinch — she was punishing those tight little buds. Jill gasped and started spasming on my leg, and as she came, her liquid slid down my thigh.

“Let’s get a condom on you,” Olive said. She pulled one out of the nightstand drawer and rolled it on expertly. Then she grabbed one of the vibrators, switched it on, and held it against my balls.

I made some sort of garbled noise as the vibrations shook through me. I’d never even considered this as an option, but it was amazing. The four women stood around the bed, looking down at me as I jerked in my restraints, and it felt like I was in some kind of pagan ritual.

But there were three vibrators, and it didn’t take long for Olive to thrust one inside Lisette. I watched as she pumped the pink cylinder in and out, then pressed it against Lisette’s clit. The curvy woman orgasmed with a shriek.

Jill had been watching, but as her friend came, she slipped her hand between her thighs and started rubbing. Then she straddled me and gripped my cock, guiding it to her pussy. She slid down, and her cunt was tight and perfect. Her thick thighs rested on either side of my hips, and when I thrusted up into her, her beautiful breasts jiggled.

I couldn’t believe this was the woman who had driven me to band practice and made me sandwiches during high school. Now, she was an uninhibited freak. She rode me with her head tossed back, and then Carol-Ann held a vibrator to her clit, and Jill came with a long moan.

“My turn,” Carol-Ann said. She had tattoos all over her arms and shoulders, her pussy was bare, and a tiny heart was tattooed on her lower belly. She nudged Jill aside, then sat on my dick. If anything, she was even wetter than Jill, and significantly rougher. She raked her nails down my chest and fitted her hands around my throat. As she rode me, Lisette and Olive got into a super-hot 69 position on the bed beside us, tongues pressing against pussies.

This was now officially the best day of my life. My only concern was making sure I didn’t come too fast. The mix of bondage and sexy MILFs was about to make me explode. Thankfully, Carol-Ann came quickly, and then it was Lisette’s turn.

She was so voluptuous it almost hurt to look at her. Breasts, waist, hips, thighs — all of it appealed to me. I wished I was free so I could grip her hips and thrust up into her, but instead, she straddled me in a reverse-cowgirl position. Jill stood at the end of the bed and kissed her while she bounced up and down on my dick. All I could focus on was the slap of flesh as she used me. My dick slid in and out of her beautiful pussy, and I watched every blissful second of it. I strained against my restraints, but I was fully tied.

It occurred to me that I was just a convenient cock and that they’d been waiting for an opportunity to give in to their old college lesbian feelings. It wasn’t a tragic thought. If they wanted to use me as a fuck-stick, I was more than willing.

Soon enough, Olive took over for Lisette. I was glad this was the final woman, because I wasn’t going to last, and I desperately wanted to service them all. As I fucked Olive, Jill crawled up my body and sat on my face, and there was no doubt that the best ride of my life was almost over. The taste of my best friend’s mom’s pussy was even better for how illicit it was. I came with a shout, nearly hurting my wrists and ankles as I struggled with the bindings.

Then they let me go.

Just kidding. These women were freaks. And we all knew Keith wouldn’t be home anytime soon.

" />

Book Club Cougars

Storyline

My friend Keith’s mom has a book club — a quartet of attractive, forty-something women who drink Chardonnay and cackle loudly about filthy books.

They’re over at his house every few weeks. They’ve read everything from the Kama Sutra to a dominatrix memoir to romance novels. Keith finds it uncomfortable. I think it’s hilarious.

We both recently started college. I’m 19, but I haven’t lived a particularly sheltered life. I lost my virginity to my middle-school girlfriend and have gotten lots of action since then. But one thing I had never done — even though MILF porn really turned me on — was sleep with a much older woman.

So you can understand why thinking of four hot moms talking about sex as they got buzzed on wine was a bit distracting. Since Keith’s mom Jill is one of these MILFs, I hadn’t confessed this to him, but I fantasized about the scene a lot. What if I just walked in there naked, offered up my services, and watched what happened?

Well, the other day I was hanging out at Keith’s place when the book club convened. We were listening in from the kitchen as they discussed a sex-filled romance novel. During this eavesdropping, Keith got a phone call. His girlfriend’s car had broken down, and she needed help.

I offered to go with him, but Keith said no. By the furtive way he responded, I figured his girlfriend saying “My car broke down” was code for “Let’s have sex,” so I let it go. He told me to finish our takeout dinner and leave whenever.

I happened to be feeling pretty good about the results of a lot of gym work in recent months, which helped me walk with decent confidence into the living room where the book club was meeting. The women were sprawled all over the couches — tattooed Carol-Ann, curvy Lisette, foul-mouthed Olive, and mind-numbingly hot Jill. One Chardonnay bottle was empty, and another would be soon. When I appeared, they all stopped talking and stared at me.

I casually took a seat on the sofa near Jill, even though it was hard not to feel awkward with them staring at me. “So what are you discussing today?” I asked.

“Oh, you know,” Olive said, winking at me. “Threesomes, foursomes, gang bangs.” The other ladies collapsed into giggles.

“Oh, yeah?” I asked, playing it cool. “Any of you have experience with those things, or is this all hypothetical?”

Carol-Ann traced a finger up Lisette’s thigh. “Actually,” she said, “we were all in the same sorority. So yes, we got freaky a few times.”

This was excellent news. Apparently they’d all slept with each other in college.

“Please, Carol-Ann,” Jill teased. “Don’t traumatize the boy.”

I gave her my best smile and subtly flexed my biceps.

“I’m not a boy anymore, Jill,” I said. Then, in a move so bold I could hardly believe myself, I looked her up and down and licked my lips.

“Jill, I think that young man is offering you something,” Olive said, draining her wine glass and pouring another. The others stared raptly as Jill flushed under my gaze.

“Not just her,” I said, deciding to go all in. “I have no practical experience with group sex, but I’d love to learn.” I winked.

There was a moment of appalled — or intrigued? — silence, and then Olive burst out laughing. “Well, shit,” she said. “I’m in. It’s been a while since I had some nice, young cock.”

“Me, too,” Lisette said, leaning over to squeeze my bicep appreciatively.

Carol-Ann got up and straddled my lap, then started kissing my neck.

Jill had her hands over her face, but she was watching through her fingers. I rocked my dick against Carol-Ann, who moaned, and Jill blushed again before throwing her hands down.

“Not a word of this to Keith,” she stressed, understandably, and moments later she was cuddling and making out with Lisette on the couch next to me.

I got to kiss all of them in the living room. They also all kissed and groped each other. Apparently, sorority girls never forget how to get down, because within a few minutes, Olive was fingering Lisette on the couch while Jill kissed her. I felt like I was in heaven.

Eventually, we took things to the bedroom. Jill was divorced, so there was no husband to worry about — just a king-size bed and a nightstand full of toys. Jill brought out three different vibrators, then pulled restraints out from beneath the mattress. They were black with padded cuffs that attached to both wrists and feet.

To my surprise, the cuffs were apparently intended for me. The ladies escorted me onto the bed, then stripped off all my clothes and tied me up. I asked them to skip the blindfold, because there was no way I was going to miss seeing my MILF fantasy come to life.

Then they all got naked. Their bodies were so sexy. I’d never been with a woman who had cellulite and a tummy and all those supposedly “bad” markers of age. These ladies looked womanly, and something about all those curves made me want to fuck them blind. It was like seeing classical fertility goddesses come to life.

Jill crawled over me first. Seeing my friend’s mom like this — naked, with her breasts swinging over me and her mouth red from kissing another woman — was beyond hot. My dick was incredibly hard, and it stood straight up off my belly. Jill grabbed it and started pumping, rubbing her crotch on my thigh. I was shocked at how wet she was — she was practically dripping as her pussy ground into me, smearing her moisture over my skin. I lifted my leg as much as the restraints allowed, trying to rub against her.

Olive placed a hand around my throat and held me down. “No moving,” she said. “We’re going to use you.”

“Fuck yes,” I said. I’d imagined doing them all one by one, leaving them happy and satisfied, but instead it looked like they were going to do me one by one. And yup, I was down for this.

While Jill rode my thigh and Olive gently choked me, Carol-Ann bent over the bed and sucked my dick. She took it deep, bobbing up and down and following the motion with her hand.

Older women were incredible, I decided. I was never going to fuck a young woman again.

Jill was grinding hard, and I was torn between focusing entirely on Carol-Ann’s mouth and fixating on Jill’s pussy and what it would take for her to come. The final member of the party, Lisette, reached out and squeezed Jill’s nipples while she rode me, and it wasn’t a gentle pinch — she was punishing those tight little buds. Jill gasped and started spasming on my leg, and as she came, her liquid slid down my thigh.

“Let’s get a condom on you,” Olive said. She pulled one out of the nightstand drawer and rolled it on expertly. Then she grabbed one of the vibrators, switched it on, and held it against my balls.

I made some sort of garbled noise as the vibrations shook through me. I’d never even considered this as an option, but it was amazing. The four women stood around the bed, looking down at me as I jerked in my restraints, and it felt like I was in some kind of pagan ritual.

But there were three vibrators, and it didn’t take long for Olive to thrust one inside Lisette. I watched as she pumped the pink cylinder in and out, then pressed it against Lisette’s clit. The curvy woman orgasmed with a shriek.

Jill had been watching, but as her friend came, she slipped her hand between her thighs and started rubbing. Then she straddled me and gripped my cock, guiding it to her pussy. She slid down, and her cunt was tight and perfect. Her thick thighs rested on either side of my hips, and when I thrusted up into her, her beautiful breasts jiggled.

I couldn’t believe this was the woman who had driven me to band practice and made me sandwiches during high school. Now, she was an uninhibited freak. She rode me with her head tossed back, and then Carol-Ann held a vibrator to her clit, and Jill came with a long moan.

“My turn,” Carol-Ann said. She had tattoos all over her arms and shoulders, her pussy was bare, and a tiny heart was tattooed on her lower belly. She nudged Jill aside, then sat on my dick. If anything, she was even wetter than Jill, and significantly rougher. She raked her nails down my chest and fitted her hands around my throat. As she rode me, Lisette and Olive got into a super-hot 69 position on the bed beside us, tongues pressing against pussies.

This was now officially the best day of my life. My only concern was making sure I didn’t come too fast. The mix of bondage and sexy MILFs was about to make me explode. Thankfully, Carol-Ann came quickly, and then it was Lisette’s turn.

She was so voluptuous it almost hurt to look at her. Breasts, waist, hips, thighs — all of it appealed to me. I wished I was free so I could grip her hips and thrust up into her, but instead, she straddled me in a reverse-cowgirl position. Jill stood at the end of the bed and kissed her while she bounced up and down on my dick. All I could focus on was the slap of flesh as she used me. My dick slid in and out of her beautiful pussy, and I watched every blissful second of it. I strained against my restraints, but I was fully tied.

It occurred to me that I was just a convenient cock and that they’d been waiting for an opportunity to give in to their old college lesbian feelings. It wasn’t a tragic thought. If they wanted to use me as a fuck-stick, I was more than willing.

Soon enough, Olive took over for Lisette. I was glad this was the final woman, because I wasn’t going to last, and I desperately wanted to service them all. As I fucked Olive, Jill crawled up my body and sat on my face, and there was no doubt that the best ride of my life was almost over. The taste of my best friend’s mom’s pussy was even better for how illicit it was. I came with a shout, nearly hurting my wrists and ankles as I struggled with the bindings.

Then they let me go.

Just kidding. These women were freaks. And we all knew Keith wouldn’t be home anytime soon.

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