Letters to Penthouse XIII

by Penthouse International

  In August my mother went away on vacation for three weeks, and since I was alone I had the chance to dress up almost every day. One Friday morning, I decided to dress like a sissy slut The outfit for the day was a black satin blouse, a red leather skirt, black satin French-cut panties, a black satin push-up bra, a black garter belt with silk stockings and a red pair of patent-leather pumps. After putting them on I felt really horny and started reading a skin magazine. I turned on my Discman and listened to some tunes while I rubbed my cock through my satin panties.

  I was lost in my own little world, when I suddenly had a feeling that someone had come into the house. In a panic, I ripped off the headphones and started for my bedroom. I only got about five feet when Annabel came through the door of the living room.

  I almost died. She stared at me for a minute, but the look of shock on her face quickly turned to a shrewd smile. She started to explain that she had dropped by to see if I needed anything, and when no one answered the door, she came on in. I had forgotten to lock the door when I brought the garbage out that morning. My heart was pounding in my ears, my mouth was as dry as a desert, and I could only stutter and stammer. When I finally had my brain working again, I started pleading with her to keep my secret. Annabel walked toward me and, to my surprise, rubbed my cock through my leather skirt. Then she said maybe we could do some special things that we could both keep secret. I was too astonished to reply, so I just nodded my head.

  Annabel was wearing a blue jumpsuit with a white belt, and her nipples were straining against the fabric. Now, standing in front of me, she unzipped the top of the jumpsuit. She had on a baby-blue satin bra that just barely contained her beautiful tanned tits. I was so horny that my panties were drenched with pre-come. I reached up and grabbed hold of her silky mounds. Annabel let out a little gasp, then asked me if I would like to help her undress and give her an all-over massage while still in my sexy outfit. I was ready to blow my load. I reached out and helped her take the jumpsuit off, pulling it down slowly. I was so close to that sweet pussy that I had been dreaming about for so long, and when she stepped out of the jumpsuit I could see that her flowery satin panties were soaked through.

  I begged her to let me eat her sweet pussy, and was delighted when she said I could lick the outside of her panties. As I slowly leaned in she grabbed the back of my head and pushed my face into her crotch. Then she started moaning and telling me to nibble her clit through her panties. I complied with her request, and soon felt her sticky wet juice oozing through the panties and running all over my face. After a quick orgasm, she sank down onto the floor with me. She told me she had always known I was hot for her, and had loved to make me horny. But seeing me in my sexy female outfit had made her curious and also excited her. She told me that her husband was not very active with her sexually, and that she would keep my secret, because now we could enjoy each other. Then she asked me if I wanted to fuck her.

  I stood up and grabbed her by the hand and pulled her close. I could feel her firm tits through my satin blouse. I began to kiss and nuzzle her neck, and she melted in my arms. I decided to take her there on the living room floor. I unhooked her bra and let it fall to the floor, leaving her panties on. I started to unbutton my own blouse, but Annabel stopped me, saying that it was a turn-on for her to be fucked by a sissy bitch. I pulled up my leather skirt and pulled off my satin panties, and my cock sprang to attention. I couldn’t wait a moment longer. I slid her panties to the side and slid my cock into her dripping snatch.

  I was on top of the world. I fucked her for a few minutes, then told her I wanted to fuck her sweet ass. She said that would be great, and bent over the arm of the sofa. I made a quick trip to the bathroom for some Vaseline, which I generously applied to my cock. Then I knelt behind her and pulled her panties down far enough to slide my cock up her ass. As I worked it in I caught a glimpse of my reflection in the television screen. I was so turned on I was ready to unload my come. My fantasy of being caught in my sexy clothes had come true, as had my dream of fucking Annabel. She was now bucking like a bronco and moaning loud enough for the neighbors to hear, and I couldn’t hold back any longer. I shot a load of hot sticky come deep into her ass.

  After I pulled my cock out of her she rolled over and said that we were gong to have a lot of fun together in the future. And she was right. We now fuck on a regular basis, and Annabel has bought new additions to my wardrobe for our sex sessions. Her favorite outfit for me to fuck her in is a blue leather dress, matching blue lace panties and bra, a blue garter belt with sheer stockings, blue patent stilettos, and a shoulder-length blonde wig. We are both very happy with our relationship, and we continue to keep each other’s secret.—G.B., Topeka, Kansas

  THEY WERE STRANGERS ON A TRAIN, BUT THEY FOUND A WAY TO ENLIVEN THE TRIP

  I live in the suburbs, and it takes me over an hour to get to work every day on the train. To pass the time, I often find myself fantasizing about the various women I happen to see. I like to imagine what they look like without their clothes, and to fantasize about the kinky things they like to do at night—with me, of course. And on a crowded train, when a woman squeezes by and accidentally presses up against me, I often get a hard-on despite myself. Although my imaginings are only in my mind, they make my daily commute bearable, even enjoyable.

  A couple of weeks ago I was in the office late trying to make a deadline, and did not get out until almost midnight. The trains were all pretty empty by that hour. At the last stop before the train headed out of the city, a stunningly beautiful woman got on. She had dark hair that was clipped high on the back of her head; she had little makeup on, and although she wore a long overcoat that reached to her ankles, I could tell that she had a fine figure—at least I began to imagine that to be the case. As the train picked up speed she found a seat facing me, a few rows away. She pulled out a newspaper and a pen and started doing the crossword puzzle.

  As the train clicked along, my mind wandered. I started thinking about different situations I might find myself in with her. She would follow me off the train and trail me as I walked home. At my front door, I would look around and see her at the corner naked.

  My eyes glazed over as I enjoyed these thoughts, but I must have been looking at her, because when I came back to reality I saw that she was staring straight at me. My dick was so hard at that point I didn’t think I could stand up.

  I was embarrassed and quickly looked away. I didn’t want her to think that I was a pervert or anything. I didn’t want her to freak out, even though the only other person in our car was an older man snoring at the far end. But when I looked back at her, she was still gazing at me with a faint smile on her face.

  I met her gaze. My heart started pounding as my mind scrambled to get a grip. I had no idea what to do next. I was good at imagining many things, but I had never thought something like this would happen in reality.

  She could probably tell that I was stunned, and she took it upon herself to initiate the action. She lifted one leg onto the arm of the seat, then slid one hand under her coat, and I saw her arm moving as she looked up at the ceiling. She was obviously pleasuring herself for me to see. I was mesmerized. She then stood up and walked toward me. She tossed her bag carelessly onto one of the seats, then sat down on another one just across the aisle from mine. “Workin’ hard?” she asked.

  “Uh, yeah,” I replied.

  She reached over across the aisle and loosened my tie. Then she slumped back and looked up at the ceiling, letting out a loud sigh. “Boy, am I beat,” she said.

  Then she undid the buttons of her coat, opened it up and lifted up her skirt. She eased over to the window seat and looked at me as she reached under her panties and started playing with herself.

  By this time, I had gathered some of my senses, and I quickly moved across the aisle and sat down next to her. She swung around in her seat, lifted her legs and placed her feet in my lap. Then she started caressing my rock-hard cock with her toes. I undid my pants and took my
manhood out. I could tell that she was pleased with what she saw. She eased her body up a little and shimmied out of her underwear to show me her moist cunt.

  I tried to get on top of her, but the seat was a little too small for me to maneuver comfortably. My pants got in the way, and I banged my elbow on the back of the seat in front of us. But the woman obviously knew what she was doing. Without a word, she got me to lie back across the seats, and then proceeded to straddle me. Her cunt was slick and juicy, but tight. I hunched up in order to enter her all the way, and she began to pump me. She jounced up and down as though the train was going over some large rocks. I looked at the window and saw the occasional light as the train went through a long tunnel. My view was blocked as she leaned down to kiss me. I placed my hands on her hips, reaching under her blouse and then up toward her tits. I caressed her breasts, then quickly undid her blouse and her bra so that I could feel those glorious mounds. They were neither too big nor too small. Of all the women I had ever fantasized about, she was by far the best-looking. And here I was actually fucking her on a train!

  As she broke the kiss and straightened up I started to suck on her puffy nipples. She wrapped her arms around my head as she continued to move up and down, faster and faster. I was on the verge of coming when I heard the train operator’s voice: “Basking Ridge next stop. Basking Ridge.” We were now out of the tunnel and the train was slowing down. I could hear the man snoring, and I began to panic. But the woman seemed not to notice; she continued to pump, caught up in her own pleasure. There I was, reaching the moment of climax and scared shitless.

  I started sweating, wondering what to do as we pulled into the station. As the train came to a stop, I could see the shock on the faces of the people on the platform as we passed by. Then I heard the train doors open, and I opened my eyes just in time to see the woman grabbing her things and rushing out of the train. I looked down and saw that there was a wet stain on my pants, rapidly getting darker and bigger. The man at the other end was still deep in sleep. And I was still in my original seat.

  I had to acknowledge that it must have been a dream, although it seemed so real, even afterwards. For a couple of days I stayed late at work again, even though it wasn’t necessary, hoping to see her once more, but I never did. I still find myself looking for her on the train, and sometimes I think I’ve spotted her, but it always turns out to be someone else. I still fantasize about the women I see during my journeys, but somehow it’s not the same …—Name and address withheld

  HIS PRESENT FROM HIS GIRLFRIEND WAS HIS GIRLFRIEND’S SEXY FRIEND

  I always thought that stories about girls arranging three-ways for their boyfriends were made-up fantasies that never actually happened out here in the real world. A lot of guys probably want to believe those stories are fake, so they won’t think they’re missing out in their own sex lives. But ever since my girlfriend Dawn made that fantasy come true for me, I am definitely a believer.

  I should mention up front that Dawn and I do not make much money between us. She is a nursing assistant and I unload trucks down at a department store in town. We moved in together a couple of months ago. Her parents had kicked her out of their house for dating me. I didn’t meet their high-potential-son-in-law standards, I guess. Fuck them.

  Anyway, Dawn had complained for a couple of weeks before my birthday that she had no idea what to get me. I have to admit that I was not much help. I am a pretty simple guy, with simple tastes. Put me in front of a TV showing a WWF match and hand me a six-pack, and I’m happy.

  Besides, I knew Dawn couldn’t afford to waste her money, and I didn’t want her to feel like she had to spend anything on me. I told her that I would be happy if she just made me my favorite dinner on my big day. But what Dawn cooked up turned out to be a damned sight tastier than steak and hash browns.

  Dawn knew I liked the looks of one of her coworkers, a pretty blonde named Alicia. I had first seen Alicia at Dawn’s company picnic. Those two girls had one thing in common: they each had an absolutely amazing ass.

  I should mention that my favorite part of the female anatomy is the butt. There is nothing sexier to me than a girl with a really great ass who likes to show it off. That is what had attracted me to Dawn. She has a closet full of tight miniskirts and short-shorts, because she knows exactly how great she looks in them.

  Dawn never has been the jealous type. She even kind of gets off on me telling her about other girls I fucked before we got together. I have never met another woman with that kind of healthy attitude about men. She really is one in a million, for sure.

  Perfect example: When Dawn noticed me staring at Alicia’s ass that day at the picnic, she said, “I’ll bet you would just love to stick your big dick up her tight butt, wouldn’t you?” Then she reached between my legs to stroke my cock through my pants. The two of us were sitting off at a table by ourselves, where nobody could see what she was doing to me.

  “I’ll bet Alicia has a really pretty little brown asshole hiding in those tight shorts of hers,” Dawn added, squeezing my prick through my jeans. “The kind that needs a whole lot of lubing up before a big dick like yours can get inside it.”

  She kept up that line of talk, whispering in her husky voice and rubbing my dick. We ended up getting so turned on from fantasizing about Alicia that we snuck off behind a tree. Dawn got on her knees in the grass and sucked my cock. I think she must have known that was I was thinking about Alicia’s ass when I came in her mouth. Well, I couldn’t really help myself, now could I?

  Still, I thought it would be pushing things to ask Dawn to introduce me to her hot co-worker. Like I said at the beginning of this letter, I did not think that any girlfriend alive would willingly share her man. Dawn was cool when it came to talking about past lovers, or just fantasizing. But I thought she might get pissed off if she thought I still might want to nail another girl now that we were living together.

  Besides, she was managing to keep me plenty happy all by herself. Dawn teased me in bed sometimes about my preference for anal sex. She would stick her bare butt in my face and say, “Come on and use your tongue on me, baby. Show me what you can do. Stick your tongue right up my ass.” She was never satisfied unless I licked her for a good, long time before fucking that sweet little notch between her cheeks. I didn’t have anything to bitch about when it came to my girl’s performance in the sack.

  The night after the picnic, Dawn surprised me by saying, “I’ve got a kinky idea. Act like I am Alicia tonight. Here, I’ll even turn out the lights, to help you pretend.”

  She turned out the lights and got in bed with me. I was already naked. She wriggled out of her nightgown under the covers, then reached for my cock. “You’ve got such a nice, big dick,” she whispered. “What would your girlfriend Dawn think if she knew that we were in bed together like this?”

  I couldn’t help laughing. “This is too weird,” I said.

  Dawn gave my cock a little push. “Either play along, or you don’t get any tonight.”

  “Okay … Alicia.”

  Dawn went back to stroking my cock. She said, “Dawn told me that you really like my butt. She said you wanted to fuck me in the ass. Is that true?”

  I reached around her body and squeezed her bare cheeks. “It sure is, Alicia,” I said, playing along. “I would love to spread your cheeks open and fuck you that way. Have you ever had a stiff cock up your ass before?”

  “Never! But I guess if you were gentle with me, I might let you try to put it in me that way. Just once.”

  I rolled her onto her stomach. I have to admit that I was getting excited by our little role-playing game. Not being able to see Dawn’s face made it easier for me to pretend it was Alicia lying naked on the bed in the darkness.

  “Here, let’s see if you like this,” I said. I held her cheeks apart and licked up and down her smooth crack. When I wormed my tongue inside the rim of her asshole, she said, “Mmmmm, that’s wonderful. Keep doing that.”

  I licked and kissed h
er asshole some more. “I think you’re ready now,” I said. I reached for the bottle of baby oil we keep on the nightstand. I squirted some down her crack, and started working it into her puckered anus with my fingers. I used some more to grease up my dick.

  I pressed my erection against Dawn’s little asshole. “Are you ready, Alicia?”

  “Yes, yes,” Dawn said, lifting her butt. “Put it in me. I really want it.”

  I slipped my prick up her ass with one thrust. She was so hot inside, and I was so turned on, that I came in less than a minute. All I could think about was Alicia’s face as I shot off my load in Dawn’s hot, slippery ass.

  That night must have been when Dawn made up her mind what she would be getting me for my birthday. When I got home from work on the big day and walked into the bedroom to change out of my sweaty work clothes, Dawn and Alicia were there in bed together. The sheet was pulled up over their bodies, but I knew they were naked. They had great big smiles on their beautiful faces.

  I didn’t come in my pants, but I sure as shit came close. Until you actually have seen a sight like that in person, you have no idea how goddamned hot it is. My dick was throbbing.