Letters to Penthouse XXXIII

by Penthouse International

  Before I knew it, we were kissing. Instinctively, my hands slid down her body to cup her butt. Our kiss grew passionate until the DJ announced last call and the lights came back up.

  Trying to act calm, we headed back to our table, where my half-drunk mom astonished me by saying she was going home with her new friend, she planned to spend the night, and she hoped I wouldn’t be upset. She asked me to drive Lois home, said she’d see us in the morning, and with that simply left!

  On the ride home, Lois and I hardly spoke. I was trying to sort out my emotions concerning my mom, but that was soon forgotten when I realized Lois had scooted next to me on the seat and was caressing my thigh, very near my crotch. Drunkenly, she leaned into me and licked my neck and ear while she squeezed my cock. She lowered my zipper, took out my cock, and stroked it a minute or two before dipping her head and taking it in her mouth!

  I couldn’t believe it. Here I was driving down the road getting a fantastic blowjob from my mom’s old friend. In no time at all I shot my load. She swallowed it all. After I came, she cleaned me off, then put my cock back in my pants.

  Ten minutes later we were home. Lois walked into the house all prim and proper and without a word went to her room. I felt let down. I thought we’d be at it hot and heavy as soon as we were in the door. But ten minutes later she hadn’t returned, so I went to bed.

  I had undressed and was debating whether I should go to her when I heard a knock on my door. Lois came into my room wearing a white nightgown that was cut midthigh and tied in front. She asked if I was lonely. She came in and knelt on my bed while I stood watching. She untied her nightgown and dropped it on the bed. Off came her bra, and her tits hung down. Although they sagged a bit, they were still very nice. Ten years ago, I remembered, they were awesome.

  I went to her, and we kissed passionately. This is it, I thought, I’m finally going to get a chance to fuck Lois!

  She lifted her hips to help me remove her white panties. I ran my fingers through her red bush, and she purred like a cat. I sucked her nipples and fingered her pussy. She moaned and spread her legs. I had to taste her, so I kissed my way down to her bush. She tasted musky and distinctive, but good.

  I ate her out for about five minutes, then climbed up her body, cock in hand, and lined the head up to penetrate her. I figured I wouldn’t need a condom and just slid into her. She gasped and moaned. Her cunt felt warm and smooth, and although it was loose, it still felt good. I ran my hands over her body while I fucked her steadily, and she just kept moaning. I held her legs up and banged away. When she came, her pussy got even warmer and very wet.

  I kept fucking Lois awhile longer. Then I just let go and shot my load in her pussy. When I withdrew, I realized there was a big wet spot on the bed from my jism trickling out of her pussy mixed with her wetness. We kissed some more. Then she worked her tongue down my body and cleaned every juicy drop from my cock—and sucked me hard again!

  This time I fucked Lois doggie-style so I could play with her beautiful ass. I fucked her a lot longer this time, and as I felt my third climax of the night building, I stuck my right thumb in her ass. She screamed in pleasure, and I withdrew my cock from her pussy. Since it was already lubed, I began to work it into her anus.

  As she screamed and bit my pillow, I slowly buried my cock in her ass. Once I established a steady rhythm fucking her well-preserved ass, I leaned forward to rub her pussy, which made her just crazy with excitement. I couldn’t tell if she came, but I did, in her ass. Then we collapsed and fell asleep in each other’s arms.

  In the morning when I woke up, my cock was rubbing Lois’s ass as we lay on our sides. I got hard again and entered her spoon-style before switching to missionary for a long, deep fuck.

  When we finally went down to breakfast, there was my mom with breakfast ready, a smile on her face. She said she knew what we had done and hoped it was good for both of us. She didn’t mind at all.

  For the rest of my vacation Lois slept in my bed, and we fucked as much as possible, at least three times a day, every way we could think of. I hated going back to school. But Lois has visited me several weekends since, and we fuck like rabbits. She’s also talking about visiting Mom for spring and summer breaks!

  —H.D., Murfreesboro, Tennessee

  Are There Any Rules About a Guy Hitting on His Sister’s Girlfriend?

  I’m a red-blooded 23-year-old male. Recently I went to visit my sister Beth, who’s three years older than me, in Austin. Beth is bisexual and lives with a really sexy petite blonde girl named Louise. I was supposed to stay two weeks but wound up staying a month!

  Louise, in a word, is hot. Short dirty-blonde hair, blue-green eyes, a shapely body. She’s maybe five-feet-two, not even a hundred pounds.

  Beth and Louise went to work as usual—Beth to her two part-time jobs, Louise to her swing shift as a waitress. While Beth was there we caught up on old times, and the rest of the time I spent with Louise. We hit it off, flirting a lot.

  One day I asked if she was bi also. She said that if you consider only ever having one guy as bi, then yes, she was. She talked openly, saying she’d played with girls as far back as she remembered, and liked it better since most guys are jerks. We were drinking as we talked, which loosened her up even more.

  She said she and my sister had been intimate many times since sharing the apartment, but lately things had been pretty dry, mostly because of Beth working so much. She wondered if she was still attractive.

  I perked up and said, “Oh, my god, yes! You’re very hot and sexy.” When she thanked me, I said I meant it. “In fact,” I went on, “I’d love to show you.”

  Louise was sitting on the back of the couch wearing a short white skirt and a pink blouse with spaghetti straps. She obviously wasn’t wearing a bra, since I could see her nipples harden beneath it. She smiled a cute little smile and parted her legs, revealing white cotton panties underneath. I could just make out the outline of her lips and the curvature of the bottom of her ass.

  She put a finger to her mouth and lightly bit the tip, looked at me, and asked if I would really be interested in a girl knowing she was bi.

  “Absolutely,” I shot back. “Bi chicks are the hottest!”

  She giggled, then wiggled out of her little skirt and parted her legs as she sat on the arm of the couch, leaning toward me to show off her cleavage.

  “God, you’re so hot,” I said. Again she giggled.

  She stood up and pulled her panties up over her hips, drawing the crotch deep between her lips, exposing a little hair on either side. I watched intently! Then she pulled her pert breasts out of her top and held one with one hand while reaching into her panties with the other to play with her pussy.

  “Well, if you really like it,” she teased, “why don’t you show me?”

  Quick as a flash I had my cock out. I stroked it to full hardness while she turned around and got over the couch in a modified doggie position, with her cute little ass toward me. She pulled her panty crotch aside, showing me her bare ass and pussy, then went on with the tease by looking over her shoulder at me, smiling at me, and saying, “Come and get it.”

  I walked over and got behind her on the couch, but she stopped me before I could do anything else. “Show me how good your talents are,” she said.

  I knew what she meant from her wiggling her ass at me, so I got behind her and started to eat her pussy and ass from behind. She was moaning in no time. After a while she stopped me and turned around facing me, then parted her legs again. I got back between them to eat her some more. And she tasted very good, too! I played with her tits this time.

  After a while I got her up and spun her around and began to feed her my cock from behind, doggie-style. She was extremely tight, but I got in her and we started fucking away. I admired her little ass and slapped it several times while we did it.

  After a time she wanted to change positions. She got on the couch on her back, with one leg up over the back and the other on the floor. I mount
ed her and sucked her tits. We kissed like mad, and in a few minutes I shot my load.

  I didn’t stop to think that since Louise has mostly been with girls she probably wasn’t on the pill, so I could have gotten her pregnant. It was too late to worry about that! I collapsed on top of her and rested there until awhile later when she slid from under me, got between my legs on the floor, and took my cock in her mouth. She cleaned me off, then gave me a pretty fair bonus suckjob. She looked so cute with my cock in her mouth!

  After sucking me awhile and getting me hard again, she got up and straddled my hips facing me, then lowered herself on my cock and rode me cowgirl-style. She was very vocal now. I sucked her tits, and we kissed. She became more confident as she rode me, and eventually we came almost simultaneously.

  After that we cleaned up before Beth got home. I don’t think she suspected. The next day when Louise came home from work we had several hours till Beth came home, so we did it again—and after that every chance we got.

  I would have been happy to stay longer, but Louise broke it off. She said she felt bad about cheating on Beth. She said that while their relationship might have run its course anyway, she didn’t like herself for being involved with someone who could do that to his own sister. I guess she had a point.

  —G.R., Portland, Oregon

  When His Boss Asked for “A Favor,” He Had an Idea What She Wanted

  In college I had a job in a fast-food joint to help pay the bills. We had a bunch of college guys working there. We all got along well.

  Our manager was a woman named Margaret, who I swear could have been anywhere between 25 and 45. Sometimes she seemed like a high-school girl, and at other times she seemed stuffier than my mother. Some people said she had a boyfriend, but no one knew for sure. She got on well enough with all of us guys, but she always kept a certain distance.

  Margaret was small—I’d say five-four, and not much over a hundred pounds. She had long brown hair with the most adorable face. As unflattering as our uniforms were, she managed to make those tight black stretch pants the women wore look hot—they showed off her shapely legs.

  One night in my second week there, we had a slow period and the guys were standing around talking. Margaret’s name came up, and a comment was made about me being “her new stud.” The guys told me we were “her stable of studs,” and she’d fucked every guy there. They said she even took on three of them at once after closing.

  I didn’t know what to believe, but they assured me it was true. They went on to say that she doesn’t shave her pussy, so her bush is thick, and she doesn’t like condoms so she lets them fuck her bareback, and she likes threesomes and oral and anal sex and on and on. Somebody even said she had seduced a couple of girls who worked there, adding that if you can’t or won’t perform for her, she finds a way to fire you.

  I was still in disbelief but at the same time definitely excited by all of this.

  I continued doing my job as normal, and every time Margaret was friendly with me, my cock got hard as I thought about what my coworkers told me. I wondered when, and how, I would find out whether the stories were true.

  My third week there, I found out. Margaret was off that night but came in anyway to pick something up from the office. She was wearing a modest white top, a short but not too short plaid skirt, and sandals. It could have been just plain casual attire, or it could have been a calculated seductive look—you know, where she’s so sexy that she doesn’t have to flaunt it.

  She said hi to everyone, and when she came out of the office she stopped and talked to me, asking me how the job was going and such. It was only a minute or two, but she seemed really professional and put me at ease.

  Just as she was about to leave, she turned back to me and said, “I don’t usually do this, Alex, but I have a favor to ask.” She said she had cartons that had to be moved in her garage. She would pay my regular hourly wage—or time and a half for overtime—but I should feel free to say no.

  I figured it was my chance to find out about the stories, and maybe get lucky. With my cock stiffening, I said yes, then spent the rest of my shift trying to conceal a hard-on that wouldn’t die. All the other guys on duty razzed me about “getting the call.” I thought we would never get to closing time. But eventually we did.

  I went straight over to Margaret’s place. She had changed into shorts and a T-shirt, and again the look was so casual that it could have been just what she wore around the house. The shorts weren’t all that short or all that tight, but you just couldn’t help not stare at the beautifully firm, muscled legs sticking out of them. Likewise, the T-shirt wasn’t special, or especially tight, but you were riveted by the beautifully proportioned torso—fine medium-size tits (nipples popping through the cotton fabric), and a perfectly flat gut—that wasn’t at all hidden by the casually draped T-shirt.

  Let’s put it this way: She could hardly have looked more seductive if that was the look she was going for. My cock was voting 100 percent for seduction, but I didn’t know, it could have been pure wishful “thinking” on its part. You know how single-minded cocks are.

  At least the job was real. She had a whole bunch of cartons she was shipping to various relatives, which had to be brought up from the basement and separated according to the different addresses. She said she had UPS coming for them the next day and would be thrilled to be finally rid of all this stuff she was shipping off to family members.

  While we worked, she disappeared into the kitchen for a while, then returned with a tray and offered me a glass, which turned out to contain a nice stiff screwdriver. She also gave me a hand towel to wipe off some of the sweat.

  When she made a comment about how easily I was moving the cartons, and how all those big muscles of mine apparently weren’t just for show, I thought at first she was flirting, and she could have been. But I honestly still couldn’t tell for sure. It could all just have been friendly conversation. The fact is, I was working out seriously back then and was pretty muscular.

  Margaret was working hard, too, and was sweating a lot. But even sweaty she looked cool and collected—and unbelievably sexy!

  The job took less than half an hour, but Margaret paid me for a full hour, saying she couldn’t pay me any less, and besides, she said, “It would have taken anyone in less good shape at least twice as long.”

  You tell me: flirting or not?

  Then she asked if I’d like to come in for a refill of my drink. I stammered yes and followed her. She had me wait on a couch in her den. On the walls were some incredibly sexy photos of her in athletic and other poses. Surely I was being prepared for seduction, no?

  When she brought the drinks in, I couldn’t help but notice that she’d changed from her T-shirt to a halter top. Her tanned flesh was so fine and unblemished, I lost the power of speech.

  “I hope you don’t mind,” she said. “My T-shirt was drenched. Feel free to take your shirt off if you like.”

  I did, and she whistled. “I’m sorry,” she said, chuckling. “I didn’t mean to embarrass you. But you know, that’s quite a body you’ve got there.”

  The way she’d sprawled out on the couch, leaning back with her eyes closed, with her shorts riding up so far, I saw pubic hairs sticking out of her black panties. Aha! Finally I knew. I moved close beside her and slid my hand up in her shorts.

  She jumped a foot and shouted, “What the fuck, Alex?” I jumped up, afraid she might slap me. I’d have run out of the house, but my muscles wouldn’t move.

  The way she’d slumped over, I thought she was going to cry. After what felt like an hour, she said, “Sorry, Alex, it’s not your fault. You obviously have been listening to the jerkoffs at the restaurant. I didn’t think they’d gotten to you yet. That’s the only reason I had the courage to ask you to help.”

  She looked up. I saw she was crying. “Christ,” she said, “I try to be a good boss. Treat the kids fairly, be a friend. And this is what I get. I don’t dress and act like a nun, so I’m a slut.”<
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  I fished a handkerchief out of my jeans and handed it to her. She wiped around her eyes. All I could think of was of what beautiful eyes they were! Plus there was this look in them.

  “You’re sweet,” she said, giving my hankie back. It felt like she was giving me a Nobel Prize. “Thanks,” she said. “I make a point of keeping my private life private. So the assholes make it up.”

  “I … I … I—” I said. Not out loud, I hoped.

  “Just for the record,” she said, “I’ve never so much as touched an employee.”

  I sat down beside her again, and gently put my arm around her shoulder. She leaned her head on my shoulder. We just sat there like that for … well, I have no idea how long. Finally she lifted her head just enough to peck me on the cheek. It was the erotic high point of my life to date.

  “Hey, it’s not as if I don’t notice hot guys,” she said. Very tentatively, she ran her hand over my chest. “Jesus, Alex, I notice. Trust me. At your job interview, I thought, ‘If this kid’s for real, he’s the sweetest guy I’ve ever met, and that body!’ ”

  I don’t think she even realized that her hand was now kneading my chest muscles, hard.

  “You know,” she said, “I almost didn’t hire you, I was so worried how attracted to you I was. Then I realized how unfair that would be.”

  Her whole body was pressed tightly against mine now. I still couldn’t talk, but now I could move—a little. I leaned over and kissed her on the lips. I almost died when I felt her kissing me back, and opening her lips!

  I ran my hands over her smooth, creamy torso. When I felt her wandering hand on my crotch, I had that same feeling as before: Was this a signal or not? I decided it was safe this time and went to undo her halter top. God, her tits were beautiful. Not big, but just so beautiful. I had to lick them. As my lips made contact, I realized she had opened my jeans and stuck her hand inside my briefs. She was giving my erection a workover.