Letters to Penthouse XXXXII

by Penthouse International

  —Mr. G.Y., Bangor, Maine

  Who’s the Sexy Lady Trussed Up in Elianna’s Basement? It’s Her Husband!

  I received the shock of my life last year. I had been away for the week on business and planned on extending my trip through the weekend to visit a friend. Unfortunately, she came down with the flu, so I had to cut my trip short and decided to fly home on Friday. On my way to the airport, I tried to call my husband, Sam, to tell him about the change in plans, but I wasn’t able to catch him at home to ask for a pickup. Instead of leaving a message on the machine, I decided I’d take a cab.

  I arrived home in the early evening and found the house totally dark. I let myself in the front door and took my suitcase to the bedroom. Sam was nowhere to be found. I hadn’t actually expected him to be there, since it was the weekend and he knew I wasn’t due home until Sunday. Deciding to catch up on the laundry, I unpacked my luggage, gathered up my unmentionables and headed down to the basement. When I got there and flicked on the lights, I jumped and gasped in surprise.

  There in front of me was a womanly figure securely tied to a support column in the middle of the room. She wore a long-sleeved, knee-length black dress, black hosiery and black high heels. She was connected to the pole at her ankles, knees, waist and torso, held fast by lengths of white rope that stood out sharply against her all-black attire. She had a gag in her mouth and was blindfolded. My initial thought was that some creep had abducted a woman and broken into our house. I approached her to unfasten her bonds and find out what had happened. But when I got closer, I realized it was Sam!

  Sweat was running down his forehead, which streaked his mascara and makeup. I pulled the gag from his mouth and blurted out, “What the hell is going on?”

  Sam’s face was beet red as he began to stutter an incoherent explanation. As he stammered, I looked around the room and saw his open army trunk, which was stuffed with dresses, undergarments, high heels and wigs. I had not only been married to a cross-dresser for the past ten years, but one who liked being in bondage, too.

  I turned my attention back to Sam. His wrists were shackled behind his back with handcuffs, which had a string attached to them. The string ran down into a half-gallon milk jug and was connected to the key for the cuffs, which was embedded in a block of ice. Apparently, while I was away on business, he’d taken to entertaining himself by playing self-bondage games. I checked the status of the melting ice and figured he would be incapacitated for at least another hour.

  I needed a little time to process all of this information, so without a word I headed back upstairs. While I came to terms with these revelations, the ice would have a chance to melt. I made myself a drink and considered all that I’d seen. Sam did transform into a lovely woman. After all, he’s only five-foot-seven and slim, and his facial features are rather feminine. Despite this kinky bombshell, I’d always considered Sam a good, gentle person who worked hard and had always been respectful of me. Wanting to learn more, I pulled out my laptop and researched cross-dressing on the Internet. I decided that while his fetish was a little unusual, maybe I could make it work to my advantage.

  I headed downstairs and released my husband, telling him to take a shower and meet me in the kitchen. He appeared a short while later, looking contrite as he took a seat at the table. I’m sure he was expecting me to scream and yell. However, I totally surprised him when I told him to get dressed in the clothing I had laid out in the guest bedroom.

  I followed close behind, wanting to observe his reaction. He gasped when he saw that I’d laid out a selection of clothing from his stash: a white bra, panties and slip, as well as beige stockings, a floral-print dress and white pumps. He stammered and stuttered again as he tried to utter his thanks. I cut him short, telling him that I was in charge and that he needed to follow my orders. He quickly and quietly dressed, and I could see from the bulge in his panties that he was getting incredibly excited—and I hadn’t even revealed my entire plan yet!

  Once Sam was dressed, I sat him down, placed one of his brunette wigs on his head and applied his makeup. I told him he needed to perfect his cosmetology skills, but otherwise he had a pretty good handle on dressing en femme. I actually admired his taste in clothes!

  Sam was looking at me hopefully, so I took his hand and told him we were going to the movies. He was hesitant, but I reminded him who was in charge, and he readily complied. This Friday night movie date became a weekly occurrence. And as Sam grew more comfortable going out in feminine attire, we began stopping at a café afterward to sip lattes and chat like girlfriends. He was so feminine in his appearance and mannerisms that no one realized he was actually a man. Sam and I eventually began going out more than once a week, having dinner at local restaurants and going out for cocktails after work—like real girlfriends!

  And what would a girlie friendship be without shopping? I thrilled Sam when I first suggested we hit the mall together. It was as if I’d tapped into a secret fantasy of his, so off we went to the lingerie section of a major department store, where we picked up a variety of sexy bedroom outfits to round out his wardrobe. Shopping was like foreplay. It turned both of us on to be out in public, fondling underthings that we would soon be ripping off of each other in our mad haste to fuck. After our initial lingerie splurge, we added a new dress to his wardrobe every week and often complemented the purchase with new shoes. Before long, Sam had a pretty wardrobe.

  In addition to the super-hot sex that we were having after our dates, a new order was developing at home. Sam had taken on all of the household chores, like washing clothes, cleaning and cooking. With my encouragement, he readily assumed these duties, all of which he performed while dressed in a nice frock and high heels. Sam looked like a 1950s housewife as he pranced through the day. He loved it, and so did I, since it reduced my stress and gave me more time to focus on my career.

  Sam is a professor at the local university, and when the spring semester ended, I decided to kick things up a notch. On the first day of his summer break, I informed him that I’d put all of his male clothes in storage. He opened his closet to see it filled with feminine attire, and a huge smile spread across his face. I encouraged him to let his fingernails grow and insisted he give himself weekly manicures. Summer also gave me additional opportunities to explore his love of bondage.

  Our backyard is surrounded by a privacy fence and sheltered by a ring of trees. So on the first sunny day, I ordered Sam to strip off his dress, and as he stood in his bra, panties, garter belt and stockings, I strung him up between the two poles that held up our clothesline. I left him there all afternoon as I sat by the pool and worked on my crossword puzzle. I occasionally snuck glances at him all trussed up in the sunlight, and I have to admit that I was so turned on that I had to worm my hand into my bikini bottom to finger my tingling clit. Tying him up had made my pussy incredibly wet, and seeing him standing there so helplessly made me ache. I kept my eyes locked on him as I flicked my swollen button. Sam simply stood there with a desperate look in his eyes and a huge bulge in his undies as he watched me pleasure myself. The sight of my feminized plaything waiting for me to use him as I saw fit was a potent aphrodisiac, and I came hard as I formed even more wicked plans for our future play scenes.

  When Sam stripped off his lingerie that evening, he gasped at the sight of the tan lines that the summer sun had left behind. They were so sexy, and I couldn’t help tracing them with my tongue that night as we licked and sucked each other to fabulous orgasms, like the lusty girlfriends we’d become.

  I’m glad I discovered Sam’s cross-dressing, but I wish he hadn’t kept it a secret for all of those years! Life would have been a lot more satisfying and less stressful had “Samantha” been in our lives from the beginning. Looks like we’ll have to make up for lost time!

  —Ms. E.M., Portland, Oregon

  Rooftop Seduction in a Passion Pit Al Fresco

  I met her in a record store. She was the type of girl you’d expect to find in a record store in Gre
enwich Village—big black shoes, long hair tinted a hue not found in nature, ripped blue jeans, a Queensryche T-shirt and rings on her fingers, in her earlobes, and through her nose. Not the type of girl I usually fall for, but on this particular day Cupid must have been feeling unusually mischievous, because I felt his arrow go straight through my heart.

  Her nameplate read CHANDRA, an appropriate moniker. It was an exotic name for an exotic girl, and had a touch of East Indian mysticism. Her complexion was white as chalk, and her eyes were like two black holes in space, openings to vortexes where men like me slowly spiraled to the far reaches of infinity.

  Her large dark eyes regarded me as I gave her my purchases to ring up. Her nose crinkled in amusement as she looked them over: Liza Minnelli and the soundtrack from The Little Mermaid. I’m sure these were a little tame for her tastes. But she took my money and rang up the sale and bagged my CDs and handed them to me with the receipt, all very proper and correct, except that in the space of thirty seconds I had fallen irretrievably in love.

  I walked out of the store without saying anything more than “Thank you.” Numb, I wandered to the subway and went home, stripping off my clothes while jerking my painfully rigid erection, conjuring up the beatific vision of Chandra’s face. I came powerfully, and then dreamt of her.

  A few days later the memory of her was fading, and I’m sure it would’ve vanished altogether if I hadn’t been on that subway car that Chandra happened to step onto. She sat down across the way from me, her nose buried in a paperback edition of Siddhartha. A sense of panic overwhelmed me. I was being given a second chance by the love gods; I couldn’t sit here and blow it. I had to say something. Anything! So I timidly asked her if she happened to work at a certain record store.

  She looked up and pierced me with her black eyes. “Yes, I do.”

  “You sold me some CDs the other day,” I continued. “Your name is Chandra, right?”

  She smiled a bit nervously. “How did you know that?”

  “It was on your nametag. I thought it befitting that such a striking woman should have such a beautiful name.”

  Now she smiled in earnest, but was obviously shy, for a lull struck. I had to press on.

  “How are you enjoying that book?” We then started talking about Herman Hesse and Steppenwolf and philosophy. She was a part-time student of Eastern religions at a city university and was working nights and weekends at the record store. The fact that we were a completely mismatched couple didn’t seem to bother either one of us. And when I handed her my business card before I left the train she took it eagerly.

  I fantasized about her for a week and was disappointed that I hadn’t heard from her. As I was about to give up hope she called and asked me to accompany her to a concert. I said yes quickly, not thinking about what type of concert it was to be. But I didn’t care, just so long as I could be with her.

  So Chandra and I went to a triple bill of “thrash metal” at CBGB. She was having a great time listening to the music; I was happy to watch her. We went to a few more East Village nightspots before we found ourselves sharing a joint hidden in the shadows of a small street called Shinbone Alley.

  It was a hot summer night, and I was perspiring like mad. But that didn’t stop Chandra from nuzzling my chest, taking small bites as she opened my shirt. Her hands were fumbling with my fly, and before I could focus on what was happening she had my hard-on out in the open air.

  “Nice big cock,” she mumbled before lowering her mouth onto it. I banged the back of my head against the wall as she slurped up and down, skillfully sucking me, her fingers squeezing my balls. A thin shaft of moonlight illuminated her beautiful face bobbing up and down on my dick, and before I knew it I shot a heavy stream of come down her gulping throat.

  “Mmm,” she said, licking her lips clean. “That was good. I want some more. I want to get naked and fuck you.” I was more than agreeable to this, but since I live in New Jersey and Chandra—well, I wasn’t sure where Chandra lived, logistics were a problem. I wasn’t going to fuck her in this alley.

  She grabbed me by the hand and bade me to follow her. I did, through streets that zigged and zagged until we came to a four-story building somewhere in the Lower East Side. When she started climbing up the fire escape, I started to question what we were doing.

  “Sssh!” she hissed. “I know someone who lives here, but I don’t want to wake them up. Wait’ll you see the roof!” So I dutifully and quietly climbed behind her, enjoying the way her ass looked in her torn jeans.

  The roof was ordinary in most ways—a flat stretch of asphalt, with TV antennas, vents, and clotheslines. What was unusual was a large sofa sitting off to the side, covered by a canopy.

  “It’s the gazebo,” Chandra said, laughing. Apparently her friends in the building liked to spend pleasant evenings outdoors, making love; this was their makeshift passion pit al fresco.

  Chandra took me by the hand and led me to the sofa, which was covered with a satin sheet. “Classy touch,” I said, before she kissed me hard right on the mouth, her questing tongue practically wiggling down my throat. “Shut up and take off your clothes,” she said.

  We spent the next thirty seconds or so disrobing, hungrily eyeing each other’s burgeoning nakedness. She was exquisite. Her breasts shimmered in the moonlight, her pubic bush was a dark red, her thighs were thin and pale, the faint blue veins visible beneath her translucent skin. I took her in my arms and we flopped onto the sofa, rubbing our bodies against each other as if it were some ancient rite.

  I was so excited I simply sank my cock into her cunt without much fanfare. She was tight and wet, and I couldn’t help but cry out at the perfect fit. She wrapped her legs around my torso and gripped my back tightly with her fingers as I slammed in and out of her. A soft breeze blew by, making the canopy snap, the air cooling our hot, sweaty bodies.

  I built to an explosive climax and then held off, letting myself come back to earth before starting up again. Chandra took this opportunity to flip me over onto my back and ride me, smashing her hips against me. She was close to coming, and wanted to do so as fast as possible. When she went rigid on top of me, her hands balled into fists, which she beat against my thighs. She struggled mightily to remain silent, but couldn’t help emitting a barely audible hiss of ecstasy, like a volcano about to erupt. We relaxed in each other’s arms as the first orange and yellow streaks of the sunrise broke across the rooftops of the city. It was the first time I had ever made love outdoors, and I was hooked.

  I had another chance to fuck Chandra outdoors when she invited me to go sailing with her. I couldn’t have been more surprised, as it turned out her father owned a boat in the Hamptons. I had seen her only at night, and what with her milky-white complexion, I had some vague suspicions of closet vampirism, but apparently she liked to sail and wanted me to come with her. I was more than glad to.

  We took the long ride on the Long Island Railroad and went to the marina. Chandra knew what she was doing, so I sat back and watched as she prepared the vessel to go to sea. She wore a black one-piece bathing suit, the flimsy material allowing the pointy and erect nipples of her nascent young breasts to be clearly visible. My suit was not adequately disguising my arousal, and after we went out a few miles Chandra sat in my lap and ground her ass against my bulging member.

  What exquisite rapture! The sun wasn’t too hot, and several puffy white clouds provided intermittent shade, so Chandra and I felt comfortable stretching out on the deck, kissing and fondling. After many happy minutes of this she stood up and slipped out of her suit. Then she lay down and softly requested that I eat her cunt good.

  Her pussy lips were fat and puckered, and I dove into them as if they were a sea of champagne. I licked and lapped and fingered and tongued her until she writhed her way through more than one orgasm. I then rose above her, my erection imitating a sundial, and presented it to her. She wearily took it in her mouth and let me fuck her orally, the sensations of an exquisite blowjob magnified by
the warmth of the sun on my back and the sounds of the ocean in my ears. It didn’t take me long to erupt, and I filled her red-hot mouth to overflowing, the remainder trickling down to her chin. She smiled sweetly at me. We were both exhausted, but I had enough strength left in me to slowly kiss every square inch of her body, starting at her toes and finishing at her earlobes. It was a long, hypnotic process, and I felt as if I was being transported to another world, a special place that only Chandra and I occupied.

  When I finished nibbling her ears I slid my revived hard-on into her and fucked her slowly and gently, words of endearment murmured as softly as the waves lapping against the side of the boat. We came together and drifted off to sleep in each other’s arms, awakening with slight sunburns.

  Chandra and I are thinking of new ways to enjoy the great outdoors, and are looking forward to going hiking in Vermont next month. Whether it’s the city, country, or on the water, we have a great time fucking without a roof over our heads.

  —Mr. C.R., Trenton, New Jersey

  Professor Finds Fountain of Youth in Amsterdam

  I had always wanted to visit Holland, and I finally got the chance when I was offered a teaching position there. I’m a professor of cinema studies and somewhat of an expert on the Western. The chairman of the film department at a university in Amsterdam knew of my work and wondered if I might like to spend a semester teaching Dutch students all about John Ford, Howard Hawks, and Sergio Leone. I jumped at the chance.

  As I walked around the city, soaking up the atmosphere, I had a premonition that I would have an exciting affair. After seeing all the tulip gardens pictured in the travel books, the licentiousness of the red-light district provided quite a contrast. Curious, I popped into a live sex show. The acts exhibited nearly caused my skull to explode. They made similar shows in Times Square seem like grade-school Christmas pageants. Amsterdam was a carnal delight.