Letters to Penthouse XXXIII

by Penthouse International

  One evening after she’d been there about six months, Carrie stayed late after the store closed to do some inventory. At one point she went back to Rex’s office at the rear of the store to ask him a question, and accidentally caught him masturbating. She was very embarrassed, and Rex was even more so. He got very upset, and finally broke into tears as he told Carrie how frustrated he was. He told her how much he envied me for having her, and that he wished he could be so lucky. As he said this, the fantasies she and I had discussed came back to her, and she felt a charge of electricity race through her body.

  Carrie put her arms around Rex and told him not to worry, as it was natural to masturbate, and that if he needed help, maybe she could relieve him. Rex was surprised to hear her say this, but was soon begging her to do so.

  Surprising herself with her own boldness, Carrie took his hand and led him over to the small couch at one side of his office. She told him to undress, and when he’d done so she took his penis in her hand and slowly began to work it up and down. Rex begged her not to make him come too quickly, so she gripped him tightly and waited till his urge to climax had passed. Then she began to stroke him again. In no time at all he was close again, and this time he couldn’t stop. She felt his cock start to twitch as he shot five or six spurts of semen all over his stomach.

  To her amazement, after he shot he still had a hard-on, and he asked her to stroke him some more, which she did. But this time he took forever to climax, and her wrist started getting tired. Rex then suggested maybe she could kiss it or lick it. After a pause, Carrie slowly lowered her head and kissed the tip of his cock. She then licked it a little and massaged his balls, until after a minute he again sprayed all over himself, and this time he stayed soft.

  Carrie left shortly afterward, and when she got home she told me everything. It turned us both on like crazy, and we had the best sex we’d had in years. I told her I couldn’t wait till she relieved Rex again. She said she didn’t know if he would want that again, but I knew damn well he would.

  The next day, at my suggestion, she went to work wearing a short black dress with black stockings and no panties. It wasn’t long before Rex asked her to come back to his office.

  This time, as she stroked him, she let him put his fingers in her pussy, and he fingered it expertly. Then he put his hand behind her head and urged her gently down to his cock. Knowing what he wanted, she opened her mouth and took him inside. Her head bobbed up and down as she sucked him, and in less than a minute he gave a loud cry and shot his come into her mouth. Carrie swallowed most of it.

  Once again he was still as hard as ever after his first come. Carrie stroked him slowly again, looking into his pleading eyes, and asked him what he wanted. He then told her what she already knew—he wanted to fuck her.

  So, much to Rex’s surprise and delight, Carrie had him lie down on the couch and climbed on top of him, straddling his hips. She took hold of his erection and guided it to the opening of her pussy, and then, for the first time since we’d been married, she took another man’s cock inside her body. She then rode him like a cowgirl for several minutes before he gasped and shot his sperm into her receptive cunt.

  When he finished she climbed off him, with his sperm dripping from her pussy, and came home, where the two of us fucked like animals.

  After that Carrie serviced Rex once or twice a week until two months ago, when he died of a heart attack. The upside of it all—aside from our improved sex life—was that Rex left us his entire estate in his will, for which we are forever grateful.

  —Name and address withheld

  First She Told Him All About Her Tryst, Then She Demonstrated

  I wanted to write to you because I have always fantasized about sharing my wife with other men. Trish and I have been married for 22 years, and for as long as we have been together I have been turned on by her describing her experiences with other men before we were married. I was fairly experienced myself, but she was significantly more so.

  When I eventually told her about my fantasy of sharing her with others, she was extremely excited by the idea. She had always been turned on by the thought of being desired by other men, and whenever I told her that I had spotted some guy checking out her sexy body and her beautiful 36C tits she would get very excited and fuck me wildly. Now when I told her I dreamed about her meeting up with one of her old boyfriends and fucking his brains out, she practically salivated and told me that if that was what I wanted, she would do her best to make my fantasy come true.

  Shortly after that Trish went on a business trip to Chicago, where she used to live, and while there she made arrangements to meet an old lover, Jay, for dinner at her hotel. When she got home she told me in great detail all about what had happened that evening.

  The two of them enjoyed their dinner, which was accompanied by a couple of bottles of wine. Afterward they went to the hotel bar for a nightcap. By that point Trish had definitely decided to act on my fantasy and tell me all about it afterward.

  At the end of the evening Jay walked her to the elevator, and as they were saying good-bye Trish leaned over and kissed him passionately. Their tongues met, and they kissed for what seemed to her like several minutes. When the elevator doors opened she pulled him on with her.

  As soon as the door closed behind them, Jay pinned Trish against the wall and kissed her deeply and hard, his hands exploring her tits and lovely ass. Their crotches were rubbing against each other and she could feel his enormous hard-on. By the time they reached her floor they knew there was no going back.

  Once in her room Jay came up behind her and wrapped his arms around her as he started to kiss her neck. He moved one hand up under her blouse to caress her large nipples, which quickly became erect at his touch. His other hand moved down her still-flat stomach, under her skirt and panties and into her reddish-brown bush. His fingers began to rub the sides of Trish’s clit and push her cunt lips together. She was soaking wet by this time, and moaning with each caress and probe of his finger.

  Trish now reached behind to feel Jay’s cock through his slacks. It was longer than mine by about an inch, and she had forgotten how extremely thick it was. With a moan she turned to face him. They quickly pulled their shirts off, and Trish removed her bra as well. For a moment they stood there facing each other, taking in the sight of each other half-naked. Then they embraced madly, her breasts pressing tightly against his body.

  Trish began to kiss Jay’s chest, while at the same time she undid his pants and pulled them down. Then she knelt in front of that huge cock and did what she loves to do most—suck cock. Taking him deep in her mouth she gave him a thorough blowjob, stroking his balls with one hand and rubbing his butt with the other.

  Jay’s hands held on to her head until he was dangerously close to coming. Then he pulled her to her feet and proceeded to take her pants off as fast as he could. Now, with both of them naked, he wrapped his arms around Trish’s body and picked her up, holding her by her ass as she curled her legs around him. She felt his cock press against her stomach as they kissed wildly. Holding her that way, he carried her over to the bed and laid her down across it. He followed her down, kissing her hard nipples, teasing one with his hand as he sucked on the other, while she lowered her head to slide her tongue into his ear.

  After spending ample time attending to Trish’s beautiful tits, Jay headed south and began to devour her pussy. Trish gasped and moaned loudly with pleasure as Jay expertly licked her cunt. She pressed herself harder against his face as he began to suck at her clit. His fingers pulled her wet lips apart, one of them sliding inside her, while his other hand played with her tits. Trish was writhing and twisting with pleasure, and finally she screamed and arched her back as she shook and bucked her way through her first orgasm of the night.

  When her climax subsided Trish tugged at Jay’s head, pulling him up to her so she could lick her juices from his soaking face. This turned Jay on even more, and as for Trish, she couldn’t wait to have his cock inside h
er wet and eager pussy.

  He entered her slowly at first, his hands holding her legs apart. His wide cock stretched her pussy as it had not been stretched for almost 25 years. As he started to move in and out, Trish came for the second time, rolling her head back and forth and begging him to fuck her through her gasps and moans. This caused Jay to fuck her shaking, bucking body faster and harder. He pushed her legs back until her ankles were next to her head, driving his cock as deep as it could go.

  Trish grabbed Jay’s ass and dug her fingers into the hard muscular flesh as she came helplessly for a third time. Jay still did not stop, but continued to fuck her hard and fast for what seemed like hours. At one point he straightened up and pulled her legs back up so that he could take her toes into his mouth and suck on them as he continued his piston-like motion.

  Finally Jay’s breath became harsh and he began to pump still faster, and Trish knew he was building to an explosion. She braced her legs on the bed and pumped back to meet each of his thrusts. Then Jay arched his back, closed his eyes, and let out a howl as his cock erupted, spewing his come into her pulsing pussy. His intense climax set Trish off on her fourth orgasm, and she screamed with ecstasy, her eyes rolling back in her head, her body convulsing uncontrollably as Jay continued to shoot more come, which now flowed out of her pussy, down her thighs, and over the crack of her ass.

  They both collapsed in exhaustion, panting like animals. When Jay pulled out of her his thick cock was dripping and shiny purple. Her pussy was drenched, her pubic hair matted and full of come. They were both coated in sweat, and the smell of sex was thick in the room. After a while Jay got up to shower, but Trish could only lie there, still experiencing the occasional residual tremor from her earth-shattering orgasms.

  When Trish got home a few days later, she described everything that had happened, and then proceeded to replicate that evening by demonstrating it all with me, every kiss, every touch, every last wild orgasm. We fucked five times over the next 12 hours. I could not get enough of her.

  Now Trish has begun looking up some of her other previous lovers, trying to find out where they live now, with an eye to visiting them in the future. I keep telling her that she doesn’t have to limit herself to old lovers; new guys are okay, too. But now she’s become fixated on guys from her past. Well, thank God she had plenty of them!

  —J.N., Eugene, Oregon

  Even in the Morning, a Bar Can Be a Great Place to Find a Friend

  I work third shift, midnight to eight, and normally stop by a local tavern after work for a beer or two. Two weeks ago, after my first beer the bartender came over and handed me another—“courtesy of the lady at the other end,” he said. I looked and saw a woman I had never seen in there before, alone. In her 20s, I’d say, kind of plain, her reddish-blonde hair pinned at the top of her head in a “teacher” kind of way.

  I drank my beer, then got up to go thank her and to buy her one. I’m a 32-year-old married father of three, but there were maybe six people there and they didn’t care about anything but their own drinks.

  She introduced herself as Margot. She said her husband worked days and she was bored. We sat talking and drinking. As we talked, I noticed what she was wearing: a black floral print blouse, black skirt cut midthigh, tan stockings. (I knew it was stockings because I could see the lace tops peeking out when she crossed and uncrossed her legs.)

  While we talked, she put her hand on my upper leg several times to laugh or emphasize a point. I took a chance and placed a hand on her nylon-covered thigh. She smiled slyly and kept talking. I caressed her thigh, which felt good to the touch.

  When Margot had to go to the bathroom, as she hopped down from her stool she parted her legs, showing me her white panties. She whispered to me to save her seat, then covertly squeezed my crotch.

  When she came back and got on her stool, she parted her legs again, and I saw she had removed her panties. I saw her slightly hairy light-red bush. Now my hand traveled up her thigh again and under her skirt to her bare and wet pussy. While we talked, I slipped a finger in, trying not to draw attention.

  I fingered her pussy right there at the bar for at least 15 minutes before she asked if we could go somewhere for a bite to eat. She winked at me. I said, “Sure,” and we left in my car.

  When she got into the front seat, her hands went immediately to my crotch, undoing my zipper and taking my cock out to stroke. My hand went under her skirt and into her pussy again.

  We drove to a wooded area outside town that’s deserted. We started making out and masturbating each other. I got her blouse open and pulled her nice-size tits out over her bra so I could suck and lick the nipples. She moaned like crazy while I sucked her tits and fingered her pussy.

  I grabbed the back of her head and pulled it to my cock. She knew what I wanted and sucked me off like a pro. I came in her mouth in maybe a minute, and she swallowed every drop.

  I opened my door and pulled her to the edge of the seat, then got between her legs and started to eat her. She tasted musky, but it really excited me. She was yelling and hollering, and by now I was hard again, so I pushed her back on the seat and got on top of her. She put one leg up over the seat, and the other dropped to the floor. I rubbed my cock over her wet pussy and slid inside her.

  Her mouth opened, but no sound came out. I started to fuck her. She moaned and said to do it harder. I slammed into her, and the car rocked. She screamed and moaned, and I sucked her tits and fucked her as hard as I could, keeping at it until she came. I wanted to go a little longer, but I knew my time was coming. I asked if I could come inside her, and she said yes, so I shot my come in her.

  I lay on top of her till my cock softened and slid out. Her face was red, and she was sweating and gasping for breath. There were tears on her cheeks from the exertion. I stood looking down at her, and something came over me. I got hard again!

  Margot started to move, and I helped her up. As I did, she turned to grab a few wipes to clean herself up a little. But when I saw her round ass, I couldn’t resist. I grabbed her hips, and when she stayed bent over, I rubbed my cock through her pussy for lubrication, then put my cock to her ass and started working it in.

  Margot tensed and between clenched teeth said to go slow as she never was ass-fucked before. Her ass was way tighter than her cunt. With her gasping and wincing, I slowly got in her, then started to fuck her ass. She screamed and yelled as I banged her ass. I was so turned on that my climax built fast despite it being my third in less than an hour.

  I banged her for almost ten minutes before shooting in her ass. She collapsed. I gave her 20 minutes to recover. Then we returned to the bar to get her car. She didn’t stop thanking me for the hot sex. She said she had needed it for so long.

  Earlier this week I was having my usual beer with some of the other steady patrons at the bar when in walked Margot. She came right over to me, and we started talking. I noticed one or two of my drinking buddies checking her out. We bought her a few drinks, and an hour later four of us were out in the same secluded spot where I took Margot the week before.

  Each of us fucked her silly while the others waited their turn. She said please no anal business, which was too much for her. So we all fucked her pussy twice, and then took her, exhausted, back to the bar. She said she’d see me again next Monday. I almost can’t wait.

  —T.F., Milwaukee, Wisconsin

  Holidays Are a Time to Restore Old Ties, and Make New Ones

  When I got home from college this past holiday season, I was pleased to find my mom’s friend Lois, who’d recently been through a bad divorce, visiting for the holidays. I know Mom gets lonely. (She’s lived alone since my father died some years ago.) Besides, with Lois there, I wouldn’t feel so bad spending time with my old high-school buddies.

  Lois and I have always gotten on well. I have to admit that when I was a teen I used to fantasize about her. Okay, I admit I’m still turned on by her. She’s five-eight, with shoulder-length auburn hair and green eyes. In s
pite of the ugliness of the divorce stuff, she seemed pretty cheerful when she greeted me with a big hug and a peck on the cheek.

  Knowing that my mom couldn’t see, I took a big chance during that hug and squeezed Lois’s round ass. She jerked back, and for a second I was worried.

  But she was sporting a devilish grin when she said, “My, have you grown!”

  I smiled back and said, “Thanks. I’ve grown even more since I just saw you.”

  Now while I’ve fantasized a lot about Lois, nothing’s ever happened, not even much flirting. This was the first chance I took with her. She smiled, but the flirting ended abruptly when my mom got her hug.

  Nothing happened that night, and nothing much the next day other than some more flirting. That night we all went out to eat. Mom looked nice, but Lois looked awesome. She wore a long white dress with a nice long slit in the side. Her legs were bare, and her hair and makeup were flawless.

  We had a nice meal, then went to a dance club that caters to a more mature crowd. Mom and Lois teased me, noting there weren’t too many girls my age there so I’d have to settle for “old bags of bones” like them. I kidded back, saying they’re only as old as they feel. Lois said she didn’t feel that old, but my mom said she did.

  When I went to the bathroom and came back, both Mom and Lois were on the dance floor with two older men. It was good to see Mom having some fun. As I watched Lois, however, I saw her glance my way and smile several times, with the slit in her dress showing off plenty of smooth, creamy thigh and the dress clinging tightly to her butt.

  When the song ended, the women returned to our table to catch their breath. After a few minutes I felt something brush my leg. I looked down to see Lois with one shoe off rubbing my leg with her foot. She smiled, and I smiled back.

  Just then a slow song began, and Lois asked me to dance. I asked about her previous dance partner, and she said half-jokingly that he was too old for her. Then we were on the dance floor, on the far side from our table so my mom couldn’t see us while she chatted with the guy she was dancing with. Lois held me close, and no doubt felt my cock hardening against her. She made comments about my being all grown up and how I must have lots of girlfriends.