LETTERS TO PENTHOUSE LIII

Book : Part of: Letters to Penthouse (48 books)

by Penthouse International

Genres: Women's Fiction; Romance Anthologies & Collections

Synopsis

Mrs. Robinson isn't the only cougar in town. There are plenty of yummy mummys and flirty forties just waiting for a stud to make them feel young again.

Penthouse readers know these sexy seductresses are experienced, insatiable and they don't play games...unless they're playing their boy-toys. Now, take an erotic journey to the suburbs where mature MILFs, wanton wives next door, and wicked widows are stalking their young prey. Just because these desperate housewives spend their time in the kitchen doesn't mean they don't need someone to bake their pies too. In these sizzling pages, the mother of all man-eaters is waiting to make a boy into a man.

Release date: January 26, 2016

Publisher: Grand Central Publishing

Print pages: 304

Sample

I’m a very lucky guy. I’m eighteen, good-looking, and I live in a neighborhood where there are a lot of horny married women who seem to go for my ever-ready cock.

A little while ago, for instance, I spent half of an afternoon in bed with a woman who’s the mother of a good friend of mine. Her name is Kate, and she’s a great fuck for a thirty-nine-year-old, always ready and willing to give me what she and I both need.

When I got home afterward, I found Erin, my dad’s live-in girlfriend, doing the laundry. My parents were divorced about two years ago, and soon after that Dad met Erin, who moved in with us six months later. She was in her early forties, and she was always after Dad to marry her, but he always said one marriage had been enough for him.

Erin was wearing what she usually wore while doing housework—a cotton housedress. It was plain and simple, but it was short and tight enough to show me that she was still a pretty sexy piece. I had never really looked at her that way before, since I’d only thought of her as my dad’s woman; but this wasn’t an entirely normal situation. I’d just fucked my friend’s mother, and now I couldn’t help wondering if any my friends would want to fuck Erin. She was certainly good-looking enough, but she didn’t seem very wild or anything.

I was standing about five feet away from her when she bent over to get some dirty clothes from a basket on the floor. Her legs were slightly parted, and I was able to get a good look between them, seeing the milky whiteness of her inner thighs, as well as her pussy, which was not covered by panties.

I couldn’t believe she wasn’t wearing underwear—or that my cock was already hard, despite the fact that I had been fucking most of the afternoon. I instantly decided that if I were one of my friends, I would definitely want to fuck this woman.

That night Erin and my dad were planning to go out to dinner. Dad was already waiting in the car when Erin rushed out of the bedroom, wearing only black underwear, a garter belt, and stockings and carrying her dress. Swiftly she pulled the ironing board out of the closet and proceeded to iron out some wrinkles. I don’t have to tell you that I got hard again, staring at her swaying ass as she worked.

The next day I paid another visit to Kate, my friend’s mom. I took out all my lustful feelings for Erin on her, and she totally loved it. When I got home Erin was doing the laundry again, only this time she was wearing underwear. What she wasn’t wearing was her housedress. She was standing by the dryer in nothing more than a sexy bra and sexy white bikini panties. When she turned around I could just make out her pubic hair through the fabric of the panties.

“Oh!” she said when she saw me. “I didn’t know you were home.” She didn’t seem too upset, however, and she didn’t bother to cover up. I couldn’t be sure at that point if she realized the effect she was having on me or not. When she turned around again, I was very tempted to bend her curvy little body over the dryer and stick my cock right into that great ass. But I managed to control myself.

The following Saturday my dad went off on a hunting weekend, and Erin was planning to go shopping with some other women in the neighborhood. As usual she was running late, and at one point she came running out of the bathroom with a towel wrapped around her and rammed right into me as I walked down the hall. I nearly fell over, and Erin actually did. As she went down, the towel came off, and she landed on her pretty ass with her legs spread wide open, giving me a clear view of her exposed cunt.

“Jesus Christ!” she yelled. I couldn’t look away from her. “Well, don’t just stare at me,” she snapped. “Help me up.” She reached up, and I took her hand and pulled her to her feet. She didn’t bother with the towel now, and I watched her gorgeous ass as she hurried off to her room.

After she left, all I could think about was fucking her. I was so horny my head was pounding. But I was lucky again; Kate’s husband had gone hunting with my dad, and she decided to pay me a visit.

Once again she benefited from the horniness that Erin had aroused in me. She was as eager as I was, and we didn’t bother with foreplay. I laid her down on the living room floor, pulled up her skirt, slid her panties off, spread her legs, and drove right in. She moaned and urged me on, her long legs wrapping around me as I thrust away.

After we both came, we rested for a while, but soon Kate’s long dark hair was draped over my belly as her mouth engulfed my resurgent cock. That sweet mouth had almost made me forget about my lust for Erin, when suddenly I heard a voice crying, “Jimmy! What the hell?”

It was Erin. She stood in the doorway staring at us. “Kate!” she said then. “What the hell do you think you’re doing?”

An embarrassed Kate tried to explain somehow, but Erin told her to just get the hell out, and they would talk about it later. Kate was gone in a minute, leaving me with a still hard and aching cock.

Erin glared at me then. “You horny little fucker!” she said. “I saw the way you’ve been looking at me! I knew you were some kind of pervert. Now I find you’re having sex with my friend, and a married woman at that! What do you have to say for yourself?”

I was embarrassed, too, but I was also frustrated and angry. “All right, so what?” I said finally. “Yes, I have been looking at you. You’re a hot lady. And yes, I do fuck married women. I love mature, sexy women, and they like me. And you’ve been teasing me all this time, showing me your body, so no wonder I’m hot for you. What are you going to do about it?”

Erin just stood there looking at me for what seemed like a long time. Then, to my utter surprise and delight, she slowly reached up and began to unbutton her dress. I watched intently, my cock throbbing, as she opened and removed the dress, and then her bra, and finally pushed her panties down.

She stood nude, looking down at me for another moment. Then she smiled and came to stand over me, lowering herself slowly as she straddled my body, until I could feel her now-wet pussy rubbing over my cock. Her fingers guided it to her opening, and she gradually sank down on me, her mouth hanging open as she began to pant heavily. She sank down until I was completely inside her, and I reached up to squeeze and fondle her tits as she began to ride me. She moved faster and faster, and soon we were both moaning.

Erin reached a climax pretty quickly, her body shaking and spasming. She rolled off me then, and I quickly mounted her and fucked furiously into her until I spewed my come deep inside her twitching cunt.

“Oh God, yes!” She sighed then, and a moment later she went down on me as Kate had done, taking me in her mouth and cleaning all the juices off my cock—including Kate’s.

For the rest of the weekend Erin and I fucked in many positions, and she even let me get into her round little ass. It was awesome, fucking that perfect ass for the first time, and I came and came.

I still fuck around with the ladies in the neighborhood, but Erin is by far the best. She and Kate are the only ones who know about each other, and my next goal is to get those two ladies in bed with me for a threesome. That would be the ultimate turn-on.

—Name and address withheld     

Cougar is a term I hear a lot these days. Sex with older women has become popular in our culture, but I didn’t just jump on the bandwagon. I have been attracted to older women since long before the word MILF was ever invented.

I owe my fondness for vintage pussy to my friend Adam’s mom. Her name was June, and she was a forty-two-year-old divorced woman with fiery-red hair, sexy brown eyes, huge tits, and a big round ass. She was the epitome of what is now called a cougar, and she short-circuited my interest in young, inexperienced girls forever.

We moved around a lot when I was younger, so I learned to make friends quickly. I was glad I made friends with Adam. Not only was his mom sexy, but she was cool, too. She let us drink beer in her basement when we practiced playing our guitars, and I remember wishing my mom was that cool.

I really didn’t think about her in a sexual way at first. Then one late Friday night, as Adam and I were jamming, June came jiggling down the stairs, carrying an empty laundry basket. “I hope I’m not interrupting you guys,” she said. I just shook my head, and she made eye contact with me as she walked by, smiling at me brightly. Adam was busy tuning up, and my eyes followed his mom as she moved to the washing machine and started to empty it, putting the clothes in the basket.

She was wearing a black silk robe that barely covered her ample ass. After she had collected the wet clothing from the washer, she looked back at me, as though to make sure I was watching. Then she turned and bent down to load the dryer. Her robe rode up over her bottom, and I literally choked when I saw that she had no panties on. Two round, firm, beautiful butt cheeks jutted out at me, with a tuft of red hair just visible between her thighs.

I turned quickly to see if Adam had noticed me looking at his mom’s naked ass, but he was still fussing with his guitar. June closed the dryer door and passed me again on her way to the stairs. Going up the steps, her gorgeous ass wiggled back and forth, and before she moved out of sight, she turned and smiled at me again.

I had an instant erection. My cock actually hurt, as though it were being stretched beyond its limit. Adam asked me something, but I couldn’t focus on what he was talking about. I finally told him I needed to take a piss, and I bolted up the stairs and into the house.

I looked around everywhere for Adam’s mom, hoping to get another flash show, but she was nowhere to be found. Disappointed, I decided to really take a piss before returning to the basement. I found the bathroom and took out my cock, trying to piss through the biggest hard-on I’d ever had in my life. And then suddenly the bathroom door opened and June dashed in, closing and locking the door behind her.

“We don’t have much time,” she said as she pushed me down to my knees. She then put one foot up on the toilet and spread her legs, her red bush and her gaping crotch right in front of my eyes. Her pussy was already soaking wet. She grabbed the back of my head and rubbed her sopping gash up and down on my face, hardly giving me a chance to open my mouth and stick out my tongue. When I was finally able to put my tongue up her twat, she moaned and began oscillating her hips, rubbing her clit in a circular motion on the tip of my tongue. I think maybe she figured I had never eaten a pussy before, so she decided to do all the work. I just had to keep my tongue stiff.

“Are you a little kinky, baby?” she asked, but with my mouth buried in her crotch I couldn’t answer. “Let’s get a little kinky,” she said, and she turned around and stuck her ass right in my face, spreading it open with both hands and showing me her little crinkled anus. She ran her fingertip over it, causing it to gape a little. I didn’t understand what she wanted at first, until she reached back, grabbed my hair, and smashed my face into her ass. I stuck out my tongue as far as I could, rimming her asshole as she humped my face, making little moaning sounds.

“I want you to make my pussy come,” she said then, turning around again. This time as she fucked my tongue, I picked up the rhythm of her gyrations. When she would rotate one way, I would go the opposite way, and I made sure to include her clit in my tongue stroking. This really turned her on; she grabbed the back of my head and began grinding her pussy as hard as she could into my face. Just as I thought I was going to suffocate, her ass began to vibrate and she gasped loudly as she came, gushing even more pussy juice onto my face.

“Oh, that was good, you sexy thing!” she panted, and I remember feeling flattered by her gratitude. “Now it’s your turn to fuck my face,” June said. She laid me down on the bathroom rug, and with a few forceful tugs she removed my pants and underwear. My hard dick was vibrating like a knife thrown into a wooden door. She grabbed a jar of petroleum jelly from a counter, popped off the lid, and scooped some up with her index finger. She had me raise myself up a little, and then with one slow push she sank her finger all the way up my ass.

It felt a little uncomfortable at first, but when she put her mouth over my cock I forgot all about that. Her mouth was just as hot and wet as her pussy. She then gave me a blowjob such as I have seldom experienced before or since. She would swallow my cock with one movement, letting it slide all the way to the back of her throat. Then, at the moment of deepest penetration, she would lick at my balls with her tongue while simultaneously tickling my prostate, before sliding her lips back up, dragging her tongue along the underside of my dick. The feeling was so intense that I could last only a few minutes before I grunted and shot what was probably the biggest load of my life straight into her mouth. She gagged a little at first, but she soon caught up with the flow and swallowed down every last drop.

After sucking my cock dry, June helped me get myself together. She smacked my ass as she pulled up my underwear. “Thank you for playing with me,” she said. “I haven’t had my pussy eaten in the longest time.” Then she said, “Listen, Adam is going to stay with his dad on Friday. Why don’t you come over and spend the night with me?” All I could do was nod my head in a fever of delight.

For the rest of that week I avoided Adam. I couldn’t help wondering if he knew what I had done with his mom, although I didn’t think so. Still, I felt a little awkward about it. But I couldn’t wait to do it again. All I could think about was June’s naked ass winking at me. When I was with other people, I was continually trying to hide my erection, and when I was alone, I must have set a record for jacking off.

June had told me that Adam’s dad would be picking him up around five o’clock, so I figured it would be safe to get there about six. I told my folks that I would be staying over at Adam’s—which wasn’t really a lie—and finally it was time to go.

When I got there I took the steps two at a time and pounded on the front door. It seemed like hours before it opened, but when it did, it was well worth the wait. June was wearing a blue silk robe, which hung open in front, her big freckled tits hanging out for the entire neighborhood to see. She smiled and opened it all the way, giving me a quick flash of her body. She was wearing black thigh-high stockings and a black garter belt that framed her exposed red bush.

As I stared at her she grabbed me by the crotch and pulled me into the house. “I’m so glad you’re here,” she told me. “Adam’s dad came early, and I’ve been trying to amuse myself all this time.” Then she brought her mouth close to my ear. “Do you want to see how I amuse myself?” she whispered.

When I nodded, she seated herself on the couch and spread her legs wide, then slowly began stroking her box, her fingers moving up and down. I could see the moisture on those fingers and in her pussy hair. I thought I was going to come just watching her.

“Come here on my lap,” June said then, patting her thigh. At first I thought she wanted me to sit on her lap, but when I tried, she smacked my ass hard. “No, silly. Like this,” she said, and she pulled me down so that I was lying facedown across her legs, with my ass sticking up in the air. “That’s a great little tight ass,” she said as she pulled down my pants. When it was bare, she spanked me a few times, then rimmed my asshole with the tip of her finger, giggling with delight all the time, like a kid with a new toy.

“So what would you like to do?” she asked me then. I didn’t really know what to say, so I just shrugged my shoulders. “Its okay, baby,” she said, still squeezing my ass. “Adam’s dad and I had a really kinky sex life, so I like just about everything.”

My inexperienced mind was going about a hundred miles an hour, trying to come up with something special. Then something clicked, and I knew what I wanted to do more than anything.

“Can I fuck you up the butt?” I asked timidly.

“Wow! How did you know that was my favorite?” June said with a laugh.

She had me get up and then stood up herself, directing me to lie on the couch on my back. As I did so, she let her robe fall to the floor, then mounted my face, bending down over me in a 69 position. Once again I struggled for air as she rubbed her extremely wet gash all over my face, while gobbling my cock down her throat. The pleasure was so intense I was afraid I would blow my load prematurely. She must have sensed this, because she released my cock and sat upright, spreading her ass with both hands. As before, I stuck my tongue out as far as I could and let her do all the work. She positioned her asshole over the tip of my tongue and sank down on it, taking it deep into her rectum. Then she began riding my face up and down, fucking her asshole with my stiff tongue.

“Are you ready to fuck my ass now?” she moaned finally. All I could do was grunt; God knows I had been ready for some time. “Okay,” she said, getting up. “But first I want to show you my favorite toy.” And taking me by the hand, she led me over to the dry bar at one side of the living room.

The bar was well stocked, and four stools sat in front of it. She pulled out one of the stools and straddled it. “Adam’s dad made this for me,” she said as she reached underneath the seat and pulled out an electrical cord. “Plug me in, baby.”

I was confused at first, but when I plugged the cord into a nearby outlet, the bar stool began to vibrate. June moaned loudly and began humping the stool. She leaned forward and moved back a little, sticking her ass out. Then she grabbed my balls and pulled me to her, aiming my cock toward her asshole.

I spit in my hand and rubbed it on the head of my cock, then slowly inserted myself into her backdoor. Her ass was incredibly tight and even hotter than her pussy. She grunted as I gradually sank in up to my balls. “That’s it, baby. Fuck my ass,” she groaned as I stroked in and out. She began grinding her pussy into the vibrating seat and her ass around my cock.

I was crazy with lust. I grabbed her waist and began fucking her ass as hard as I could, my body slapping against her big, vibrating butt cheeks. When she yelled out that she was going to come, I knew I couldn’t hold back any longer. As she began groaning in orgasm, I let go and fired a huge load up her willing ass. The sensation was beyond belief. My hot come spewed into her, then forced itself back out around my dick, running down her ass.

As I pulled out, the rest of my sperm came leaking out of her. She sat up, letting it puddle onto the stool. Then she rubbed her pussy into it, giving out a little squeal. “Wow, that’s a lot of come,” she panted. “I hope you’re not done. I want to do this all night.”

All that night, and every time we got a chance for the next year, June and I fucked and sucked like crazy. Then my dad got transferred again, and we had to move. I never saw June again, but I never forgot what she taught me: older, more experienced women are the best lovers. I am in my late thirties now and am currently dating a fifty-two-year-old sexpot. Hurray for cougars!

—L.J., Zanesville, Ohio     

If you ever get the opportunity to do an older lady, take my advice and jump on it! It totally changed my life.

My first experience was with my best friend’s mom, Noreen. I still have difficulty believing it actually came to be, but I am so glad I went with my instincts and nailed that hot piece of ass! She is amazing. Yes, is. I still stick it to her when I’m back in town on break.

Josh, her son, has been my best friend since first grade. We did everything together—went to the same schools, went out for the same sports, were on the same teams, right up until college. Then he went east and I went west, but we’ve always stayed in touch.

My first time with Noreen happened totally by accident. It was the night before Josh was to leave for college. A bunch of us took him out to a club for a surprise party and he got wasted. I was tipsy, but once I saw how far gone he was, I stopped drinking so I could look out for him. He gets his beer balls on when he drinks and sometimes gets a little out of hand. Luckily, this wasn’t the case that particular night—he was just sloshed. So I wanted to get him home.

Our friend Rick drove us to Josh’s house and helped me get him to the door. I fished his keys out of his pocket, but as I was about to put the key in the top lock, his mother opened the door. Noreen was waiting up, the way moms do when they’re concerned for their kids. I apologized for Josh’s appearance, and she just grabbed his other arm and helped pull him in. I was happy for the help, since he was like deadweight!

Noreen said it wasn’t my fault, that she was expecting this. Once we got Josh in his bed, she said I was welcome to crash at their place if I wanted. That was an invitation I was happy to accept, because I was wiped from partying and babysitting Josh. I thanked her and went to the bathroom. When I came out, she was turning down the bed in the guest room. She looked really sexy.

I had never, ever looked at Noreen in any other way than as Josh’s mom, but seeing her bent over the bed in her nightgown like that had my dick rising to the occasion. Not wanting her to see me this way, not to mention a little bit shocked myself as to where the hell those feelings came from, I told her I was going to the kitchen to get a drink and asked if I could get her anything.

She politely said no and continued to fluff the pillows. She wished me good night and said she would see me in the morning.

Josh’s father had left them a few years before. He was a real scumbag, running around with skanks behind Noreen’s back. Josh caught him one time and punched him in the face. His dad came clean, and after that he packed his shit and left. To this day Josh hasn’t seen his dad again, and as far as he’s concerned, he’s dead.

But I knew that Noreen had seen him around town with one bimbo or another. I once heard my mom talking to her on the phone. She gradually got over it, but in the beginning it was really hard for her. I remember my mom a lot of times talking with her on the phone late into the night, trying to make her feel better.

As I got my drink, I kept replaying what I’d just seen and my totally unexpected reaction. I mean, I’d known this woman all my life, and never once had I seen her in a sexual way, not even when you’d think I would have—as I entered the wonderful world of puberty! After all, I reminded myself, Noreen is a very pretty woman with a very fine body. Maybe not like the models I saw in Penthouse Letters, but a really fine-looking woman.

With that thought I went into the living room and put on the TV. I just wanted to hang out and rethink the night’s events and images. Especially the image of Noreen’s fine round ass bent over the bed in which I was going to sleep! With that image in my mind, my cock began to grow. Since I assumed she was in bed, having already said good night, I figured what the hell—I would let my thoughts and hands run amok. I pulled my pants and briefs down and began slowly stroking my shaft while imagining what it would be like to have Noreen riding my dick.

I was really getting into it! I imagined her gorgeous tits right in front of my mouth as she bounced and ground on my cock—which was pulsing in my hand! It felt so damn good!

I stretched my legs out in front of me to get more comfortable. This was one of the best jerk-off sessions I could remember, and I wanted it to last. Again I slid my hand slowly up and down my shaft, thinking of Noreen. I pictured her bouncing slowly up and down on my lap, then taking a real pounding from my raging cock, moaning and groaning and digging her nails into my arms while I helped steady her as she rode me into sexual bliss.

I was just about there when I heard a gasp. I kept my eyes closed and prayed that the gasp was in my mind. I opened my eyes slowly, and lo and behold, there stood Josh’s mother! Looking like a deer caught in headlights, staring at me on her couch with my pants down, dick in hand.

Oh shit! What the fuck was I supposed to do now? There was my best friend’s mother watching me with my cock out, stroking myself like a horny monkey! I was mortified. I kept trying to think of something to do and kept coming up empty. It seemed like hours before either of us said or did anything. It was like everything just stopped.

Suddenly Noreen went in the kitchen. I shot up quickly and pulled my pants up, then paced. Maybe I should go up to bed and sneak out first thing in t. . .