WHEN IT COMES TO SEX, THEY KNOW IT ALL.
AND THEY’LL SHARE IT ALL… WITH YOU!

The demanding boss. The untamed hairdresser. The shameless nudist. The pouty professor. The wild widow. What do they have in common? They’re all mature women who get sexier with every passing year and know just how to pleasure their partners, the younger the better. So be ready to be hunted and devoured. These cougars are on the prowl. And you’re in for the hottest game in town.

OTHER BOOKS IN THE SERIES:

Erotica from Penthouse

More Erotica from Penthouse

Erotica from Penthouse III

Letters to Penthouse I

Letters to Penthouse II

Letters to Penthouse III

Letters to Penthouse IV

Letters to Penthouse V

Letters to Penthouse VI

Letters to Penthouse VII

Letters to Penthouse VIII

Letters to Penthouse IX

Letters to Penthouse X

Letters to Penthouse XI

Letters to Penthouse XII

Letters to Penthouse XIII

Letters to Penthouse XIV

Letters to Penthouse XV

Letters to Penthouse XVI

Letters to Penthouse XVII

Letters to Penthouse XVIII

Letters to Penthouse XIX

Letters to Penthouse XX

Letters to Penthouse XXI

Letters to Penthouse XXII

Letters to Penthouse XXIII

Letters to Penthouse XXIV

Letters to Penthouse XXV

Letters to Penthouse XXVI

Letters to Penthouse XXVII

Letters to Penthouse XXVIII

Letters to Penthouse XXIX

Letters to Penthouse XXX

Letters to Penthouse XXXI

Letters to Penthouse XXXII

Letters to Penthouse XXXIII

Letters to Penthouse XXXIV

Letters to Penthouse XXXV

Letters to Penthouse XXXVI

Penthouse Uncensored I

Penthouse Uncensored II

Penthouse Uncensored III

Penthouse Uncensored IV

Penthouse Uncensored V

Penthouse Variations

26 Nights: A Sexual Adventure

Penthouse: Naughty by Nature

Penthouse: Between the Sheets

Penthouse Erotic Video Guide

Copyright

Copyright © 2010 by General Media Communications, Inc.

All rights reserved. Except as permitted under the U.S. Copyright Act of 1976, no part of this publication may be reproduced, distributed, or transmitted in any form or by any means, or stored in a database or retrieval system, without the prior written permission of the publisher.

PENTHOUSE®, the One Key Logo and the Three Key Logo are registered trademarks of General Media Communications, Inc. and used by permission.

Grand Central Publishing

Hachette Book Group

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New York, NY 10017

Visit our website at www.HachetteBookGroup.com.

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Grand Central Publishing is a division of Hachette Book Group, Inc.

The Grand Central Publishing name and logo is a trademark of Hachette Book Group, Inc.

First eBook Edition: May 2010

ISBN: 978-0-446-57192-0

Contents

Copyright

Introduction to Letters to Penthouse XXXVII

Sexy Cougar Pounces on the New Guy in Town

Her Domme Girlfriend Unlocks Her Sub Side With a New Riding Crop

Sex After Forty—It Just Gets Better With Age

Woman Shows Young Job Interviewer She’s Highly Qualified When It Comes to Sex

Spirited Woman Delights in Adding to Young Admirer’s Sexual Education

Grad Student Is Happy to Be Dominated by a Sexy Older Woman

Finding True Love in the Arms of Another Woman—or Two

Lust at Sea—Two Married Couples Switch Mates Aboard a Yacht

When My Boss Told Me to Remove My Clothes I Didn’t Act Fast Enough—Big Mistake!

Promising Pianist Makes Sweet Music With Elegant Teacher

Wonderful Memories of a Time Spent Satisfying a Pair of Demanding Beauties

“Pleasuring a Woman With Someone Watching Is Altogether Exciting,” Says Nude Beach Fan

From Businessman to Lipstick Girl

“Young, Dumb, and Full of Come,” He Learns Sensual Techniques From a Worldly-Wise Lady

Sultry Woman Comes to the Rescue of Her Studly Neighbor

He Watches His Wife Get It On With Her Hunky Horse Trainer

“For Me, Nothing Beats Bagging a Virile Young Stud,” Says Sassy Woman

Newly Unemployed Man Is Cheered Up Nicely by Former Beauty Queen

American Woman Enjoys Hot Fling With Dashing International Businessman

The Torrid Keyhole Recollections of a Devoted Voyeur

Her Hand, the Belt, the Paddle, the Crop: Each Leave Their Print on His Flaming Ass

Wildly Satisfying Ménage à Trois for Mature Couple and Their New Friend

“Older Women Are the Best,” Says Man Who Knows of What He Speaks

She Discovers the Joy of Sex With a Younger Man

Grad Student Learns About Life and Loving From Vivacious Divorcée

Savoring the Special Beauty and Charms of a Mature Woman

Handsome Hotel Bellman Gives Beautiful Guest Extra-Special Service

Gentleman Presents Himself for a “Bad Boy” Discipline Session

Classy Woman Dazzles Younger Man With Her Fiery Spirit

Kinky May/December Couple Enjoy Fulfilling Man’s Spanking Fantasy

Rainy-Day Excitement for a Young Lifeguard and an Adventuresome Woman

Mature for His Age and Eager to Enjoy an Older Woman Adept at Making Love

Living the Good Life With an Enchanting Woman of Means—and Devilish Schemes

Bold Librarian Schools Curious Freshman

Anal Sex After Hours in the Boss’s Office Proves Fitting End to Workweek

How a Clever Lady Turned a Shy Guy Into a Bold Stud

Grad Student Gets Wild Welcome Home From His Favorite College Professor

Navy Man Anchors Wild On-Shore Party of Kinky Rich Women

A Hot Day Brings Him in Close Contact With the Prettiest Bare Feet in the City

A Capricious Lioness Delights in Teasing an Adoring Lamb

Woman Takes Lust-Quenching Sips From Her Very Own Fountain of Youth

Pretty Painter Strokes More Than a Canvas

Lovemaking 101: Worldly-Wise Widow Teaches Young Man the Basics

Sophisticated Couple Takes Budding Playboy to School

Real Man Proves Vibes Aren’t Just for Pussies

New Neighbors Tempt Them to Join the Lifestyle

What’s a Few Years Between Good Friends?

No Generation Gap Here—Only Great Sex Among Friends

Stylish Guy Curls Up With Sexy Hairdresser Nearly Twice His Age

Move Over, Miss Jones! Middle-Aged Widow Has the Vixen in Her

Female Lawyer Briefs Appealing New Client on How to Court Her

Fiftyish Baker Is Most Proud of Her Stud Muffin

Lusty Librarian Gives College Kid a Lesson He Can’t Learn From a Book

His Whole Life Is Dedicated to Serving Women

“A Cock in My Butt Still Thrills Me So,” Says Globe-Trotting Female Executive

Surprising Pleasure for Blushing Fellow Coaxed into Panties by Mature Temptress

Bartender/Actor and Waitress/Actress Party the Night Away With Rich Older Couple

Mature Woman Shows Eager Young Fellow Just What She Means by Total Submission

Welcome to Life On Top!

Introduction to Letters to Penthouse XXXVII

For years, men have worked through their midlife crises with pretty pieces of arm candy, and many still do indulge in such sweet treats. But these days women are just as likely to go on the hunt for handsome young things of their own, ones who can give them exactly what they need as their libidos kick up and their inhibitions drop.

This racy collection of letters to Penthouse recounts the adventures of sexy, older women who know what they want and those who love them for it. Whether it’s a sultry librarian, a naughty neighbor, or a demanding boss, these kinky cougars are on the prowl and looking for action. These ladies are as confident in the boardroom as they are in the bedroom, and they have a lifetime of experience that they’re not shy about sharing. Turn the page and read on. You may learn a thing or two yourself!

Barbara Pizio

Sexy Cougar Pounces on the
New Guy in Town

Recently, I moved out of Seattle to a much smaller town in the Midwest. I had just gotten out of a relationship and was looking forward to being single for a while, until I realized that almost every girl in town was coupled up. There weren’t as many places to meet people as there were in Seattle, and I was starting to question the wisdom of moving so far from home when I met a woman who changed my life. Lily was a good ten years older than me, and not someone I would have usually checked out. It’s not that she’s not hot, but she’s not drop-dead model gorgeous and doesn’t go out of her way to dress flamboyantly. Her sexiness is expressed in the breathy way she talks and by her talent in the sack.

We met at a movie theater, both of us opting for the arty, indie flick versus the blockbuster seemingly everyone else had chosen. When I walked in and noticed how many empty seats there were, I was dismayed. I know some moviegoers love to have the theater to themselves, but I feed off other people’s reactions. That’s part of the thrill, so when I spotted this woman with short brown hair eating popcorn all by herself, I asked if I could sit down next to her. “I’ll share,” I said, shaking my box of Rai-sinets at her.

“Sure, sit down. I’m Lily,” she said, giving me a friendly but not flirtatious smile. We sat and enjoyed the film, munching on our combined salty and sweet treats. I actually didn’t think of her as a potential romantic match at first because I wasn’t getting that vibe from her—she later told me she’s really into movies and doesn’t like to be distracted. But we exchanged numbers afterward and began hanging out, and I found Lily to be very easy to talk to. So easy that we wound up closing out a local bar one night; I had thought two hours had passed when apparently it had been five.

She took me by surprise by making the first move of sorts by inviting me to her place, planting the idea that she might be interested in more than talking. “It’s not too far, and I have a bottle of wine we could share.” I was still fairly clueless, but as we walked, I started to notice how her ass twitched beneath her clingy skirt and wondered whether she was wearing any panties. Usually, I know right away if I want to fuck a girl, but this attraction was more of a slow build. Yet once it started, I couldn’t get rid of it, and my cock was soon rock-hard.

“Lily,” I said while in the parking lot. She turned toward me, and all of a sudden, she looked prettier than she ever had. Most of her makeup had come off during the course of the night, with just a hint of shadow remaining on her eyes. Her lips were a natural, luscious pink, and I desperately wanted to feel them pressed to mine. “I need to kiss you,” I said truthfully, and pulled her close. I mashed my lips against hers, and she immediately moved closer to me and parted her lips so I could slip my tongue inside her mouth.

I was surprised when her hands moved down to squeeze my ass. She had seemed almost asexual the other times we’d hung out, not mentioning a boyfriend or even any exes, and dressing cutely but not in anything extremely sexy. Maybe she was just waiting for the right man to unleash that side of her, because she was practically ready to undo my pants right there in the street!

“God, Lily, I had no idea what a tiger you are!” In truth, she was a real cougar, a hot older woman, and I was more than happy to let her have her way with me.

We raced to her place and didn’t even bother with the wine. She led me to her bedroom, then pushed me down, pinning my wrists to the sheets. Lily actually growled as I squirmed beneath her, my cock almost unbearably hard. “You’re all mine,” she said, grinning.

“I am. Do whatever you want to me,” I said, feeling completely comfortable letting her take control. Her nails were short but painted a dark red, and she dug them into my skin. They didn’t hurt, but sent shivers throughout my body. Lily was surprisingly strong, and even though I outweighed her, I liked the idea of choosing to submit to her, and from the way she was acting, I had the impression she’d played the domme role before.

She quickly took off all her clothes, then climbed on top of me and shoved both her breasts in my face. They were larger than I’d expected them to be, once again showing that looks can be deceiving. “Suck my tits,” she demanded. I hadn’t expected Lily to use such language, but it turned me on. I opened my mouth, letting her breasts enter and trying to keep both nipples in my mouth at once. It was a challenge, but I rose to it, literally, my cock stiffening as she straddled my chest. I savored the heat and wetness of her pussy grinding against me as my tongue lashed at her nipples. “Harder,” she hissed, and I clamped my lips down around them. I could only breathe through my nose, but I liked it, and I kept lapping at her nipples until she cried out, her screams ringing in my ears.

Had I made Lily come just from licking and biting her nipples? And if they were that sensitive, how would her pussy react to my oral caresses? I was about to find out, because Lily eased her nipples away, dragging them against my chest as she moved down my body. She took hold of my cock, wrapping her soft fingers around it. By then, our age difference no longer mattered; she clearly knew things about sex that I didn’t, and I was eager to learn everything.

She rubbed my cockhead against her sex, teasing me by letting only the very tip enter her, then sliding it out. Just when I was sure we were going to start fucking, she moved away and climbed over me so she was straddling my face. Her cunt was wet and juicy, and I eagerly welcomed her, grabbing hold of her hips and pulling her tight. At that moment, pleasing Lily was my only concern, and I trusted that she’d take care of me later. I’d gone down on plenty of women, and I’m pretty sure they enjoyed it, but none behaved as lustily as Lily did.

She grabbed my hair, slammed her pussy onto my face, and rubbed her cunt against me as if I were a toy. Her fingers were all over my head, gripping my hair, digging into the back of my neck and fondling my ears as she sought out the best position. “Right there!” she ordered when my tongue tapped against a certain spot inside her. I did my best to replicate it, and she must have liked it because she moaned and her pussy got juicier.

Soon her liquid was streaming down my throat, some coating my chin, and she was shaking. Lily climbed off me, and then proceeded to lick her cream off my face. “You take orders well,” she said, turning to stare at my cock. She held it in her hand, as if displaying it for me. “What should we do about this?” she asked, squeezing it so the head bulged between her fingers.

“Aaahh,” I said, loving the way her touch felt. I had no idea what to expect, but then she crawled forward, straddling me the reverse way from before, so her wet, pink cunt was visible, and gave me the slowest, hottest blowjob I’d ever gotten. She took her time, easing off when I seemed on the verge of climax and using her free hand to fondle my balls and stroke my inner thighs. “Oh, God,” I called out, overwhelmed by the heat from her mouth and the sight of her pussy. She swallowed me all the way, moving swiftly, as if it weren’t a problem in the least to take eight hard inches deep into her throat. Lily stayed there for a few seconds, with her lips wrapped around the base of my cock while the head reached toward the bend in her throat.

I didn’t want to come because I was trying to prolong my pleasure. But when I reached forward to stroke her wetness, I couldn’t help it. I exploded right down her throat, and Lily didn’t even gag. She just shifted so only half my cock was in her throat, and then she proceeded to milk me of all my come, swallowing every last drop. I was exhausted when we were done—and impressed.

“I didn’t even know you liked me!” I said to her later that night as we finally indulged in the bottle of wine.

“I like to surprise people,” she said. We clinked glasses, and she gave me a wink. I was hard again already, only an hour later, and couldn’t wait to fuck her for real. Lily certainly surprised me and has made me feel more than welcome in my new hometown. I look forward to many more lessons in her bedroom—and beyond.

—Mr. S.L., via email   art