Letters to Penthouse III

by Letters to Penthouse III- Hot, Bothered

  Everyone loved my costume. I was having a great time and was really buzzing after drinking a couple of wine coolers. Then someone said I should do my Dolly Parton imitation, so I got up in front of everyone and sang a chorus or two of “9 to 5,” receiving numerous catcalls for my terrible singing.

  “Well, I could sing better without these,” I retorted, reaching in my bra and pulling out the panty hose I'd stuffed in it. Everyone cracked up as I threw my hose everywhere, reducing my chest to normal size. Then I said, “Have you ever wondered what Dolly looks like without her wig? I've heard she has no hair at all. If so, she'd look like this!” I then pulled off my wig and shocked everyone with my baldness. A sudden silence overcame the room as I stood in all my bald glory. Then I received a standing ovation. I was so surprised at their reactions, as they came up to me for a closer look. I explained, “I've always wanted to be bald, so I took a chance and voilá!”

  My friends were stunned, but very supportive of me and my bald look. I received numerous compliments from both the guys and girls. Everyone buzzed about it the rest of the night. I put my wig back on, and as I collected my hosiery, a guy in a dress came up to me and asked me to dance.

  It was Jeff, a guy from my philosophy class. We'd borrowed notes from each other a time or two, but weren't all that close. This was the first I'd seen of him all night. He was dressed from head to toe as a woman. He wore a red dress, black tights, black flats, a curly red wig, and full makeup. “My goodness, you're adorable!” I exclaimed.

  “So are you,” he replied. “That took a lot of guts, shaving your head. You look sensational.”

  We danced for a while, and spent the rest of the evening together. He walked me home to my apartment, and I invited him in for a nightcap. I removed my Dolly Parton wig and we relaxed on my sofa. “I can't get over how beautiful you are totally bald,” Jeff said. “You have a lovely scalp.”

  “Thank you,” I replied. “I've fantasized for a long time about being bald, and I finally went through with it.”

  “I've fantasized for a long time about dressing as a woman,” Jeff admitted. “I've been curious about what women's clothes feel like. I'm really enjoying this.”

  “You look really cute,” I said. “How do you like wearing a wig?”

  “Actually, I'm quite used to it, because I wear one all the time. You see, I'm bald too!” Jeff then removed his curly red wig, and sure enough, he was just as bald as I was! I never would've guessed that he wore a wig all this time.

  “Oh my God!” I exclaimed. “You are bald! I don't believe this. Did you shave your head?”

  “No, my hair fell out when I was fifteen, and I've worn toupees ever since. I was so thrilled when you took your wig off at the party, because I knew you wouldn't reject me if you found out I was bald. I've never had a real relationship with a woman before, because I was so afraid of rejection.”

  “But why? I think you're very handsome without hair,” I said, and I meant it. He looked very nice, despite his feminine makeup. “You have nothing to be ashamed of.”

  Since then, Jeff and I have become lovers. I helped him lose his virginity a few weeks later, and we are now almost inseparable. I shaved my head twice a week until last month, when I had my hair removed permanently. I have to wear my wigs to work, but otherwise I go wigless at all times, even to school. I even had my driver's license photo taken without a wig on. I love being bald, and I'm not ashamed to show it. Jeff has also lost his inhibitions about his hairlessness, and goes wigless in public most of the time. Sure, people stare and sometimes laugh at us, but we don't care. If they can't realize that we like the way we look, that's tough shit. Being bald isn't as bad as you think. I find it very exhilarating, and I hope some of you feel the same way.—Name and address withheld

  AN ITTY-BITTY PROBLEM

  I have a very slender, sexy figure and am very attractive, but I have a problem. My breasts are virtually the same size they were when I was ten years old, and that is no exaggeration. I'm twenty-seven now and have worn falsies and padded bras since I was thirteen.

  When I first left home at twenty, my social life was fairly good. I lost my cherry to a guy I was really in love with. He split, though. He never told me why, but I know it's because he was turned off by my flat, shapeless chest. I couldn't blame him. After that happened, I tried my best to fool everyone. I stuffed my bras and wore tight, revealing blouses that accentuated my nice, firm, fake 34B tits. I was stupid, because as soon as a guy slipped his hand inside he would realize my tits came off with my bra.

  I have really big, thick nipples that stick out a good half-inch all the time. I began to feel it was such a shame to keep them covered up all the time, so I decided to go honest. First I went to a 34A padded bra and looser tops, so friends wouldn't notice too much of a drastic change. Then I went to a lacy little training bra, always wearing a loose blouse or jacket over it. It was easy to see guys check me out, then lose interest when they saw how flat I was. At first it was almost enough to make me go back to my rubber 34Bs. I came up with a strategy. I would call attention elsewhere.

  I started wearing very short skirts (I've got perfect, long, slender legs and sexy feet) and skintight slacks with four-inch heels, garter belts, and sheer stockings. The first impact was always effective, but the guys still lost interest when they saw how flat I was. Finally a friend of mine, Kristina, a nurse, suggested I pierce my nipples and decorate them with gold rings.

  I wasn't long after that that I was going to work braless and wearing tight, silk blouses. My nipples were hard and stuck straight out all day. The feel of the cloth sliding over them nearly gave-me orgasms several times! Although it was very obvious to everyone that I didn't have any tits, the rings were outlined under the blouse whenever I leaned back, and I noticed lots of lingering stares from both men and women.

  I go braless most of the time now. As much as I wish I had tits, I find that a lot of guys accept my flatness because they're turned on by the sexy nipple rings. Kristina, whose tits are quite small and saggy, is so impressed with my attitude change and the transformation of my social life, she's thinking of piercing hers too.

  So, to all you flat-chested women out there (and I know there are lots), forget the idea of implants and decorate what you have—D.S., Quebec

  DESSERT IS SERVED

  About two years ago, on the day we moved, my wife and I worked hard, diligently packing, labeling and cleaning up.

  About seven that evening, after the movers had left, we were gathering up the remaining items in the house. We had bought a new mattress for the new apartment, so the old one was lying on the floor in the back room. I commented to my wife, Janet, that the mattress had a lot of good memories and that maybe we should give it one last fling. We were both hungry and tired, she informed me, and we still had a lot of work to do. With that, I started cleaning out the fridge. I found a full bottle of wine and handed it to Janet, telling her to finish it up as I defrosted the freezer.

  About forty-five minutes later, I finished cleaning the fridge and freezer. I wandered into the back room and found that Janet had finished the bottle of wine and was pretty drunk. She smiled and said she had changed her mind. She wanted to put the old mattress to good use one last time.

  I told her to stand in the middle of the mattress and went to get the stuff I had removed from the fridge: cherry pie filling, chocolate topping, caramel topping, a can of whipped cream, and a bottle of cooking oil.

  The first thing I did to Janet when I got back was pull out her waistband and dump the entire can of cherry pie filling down her pants. She started screaming wildly as the thick, sticky stuff slid down her thighs. I laughed and told her to relax and enjoy. She began squirming as the cool filling slowly soaked her crotch.

  I abruptly spun her around and poured cooking oil down the back of her pants. It was delightful watching the oil soak through the tight jeans covering her shapely ass. I began fondling her tits and squishing the cherries around as I massaged her moun
d through her jeans and panties. As I removed my own clothes, I told Janet to prepare herself for the kinkiest fuck of her life.

  Her tits were my next target. By now I had a rock-hard erection and was anxious to complete my dessert. I quickly unbuttoned the top three buttons of the old pink blouse she was wearing and poured chocolate sauce over her front. The sticky brown syrup quickly ran down the valley between her shapely mounds. After a few sloppy, sweet kisses, I quickly dumped the caramel topping, then pointed the nozzle of the whipped cream can down her front and emptied its contents into her blouse.

  Janet was giggling and squirming. It was time to get my hands busy. I eagerly dug in, grabbing and groping with both hands and my tongue. I nibbled her neck, kneaded her ass cheeks, and rubbed her tits. I quickly removed her jeans and blouse to fully observe the delicious mess I had created. God, she looked good enough to eat. I laid her on the mattress and attacked her with my tongue, lustily licking her caramel-and-cream-covered tits. My taste turned to cherries as I moved down her body and began nibbling around her hot cunt. I feasted on her clit for a full fifteen minutes. I could not wait any longer. I drove my cock into her cunt and began thrusting in and out. Janet squirmed on the mattress, her glistening tits bouncing as I exploded into her cunt and collapsed on her.

  Janet and I have laughed about that night many times since. She still has the stained bra and panties. I'm looking forward to our next refrigerator cleaning.—F.L., Atlanta, Georgia

  Anal Sex

  POOLSIDE THREESOME

  My husband Jim and I moved into this neighborhood about ten months ago after he was transferred to the main plant near here. His new position pays very well, so I have no need to work. I spend my days puttering around the yard and pool. By the way, my name is Audrey. I'm thirty-six, ten years younger than my husband, and we've been married twelve years.

  We soon got to know our neighbors on the left side of our property. Their kids, a son and daughter, were both away in college. Early in July I finally met their son, Val. It was July 21, a day that I will never forget. Val was with his friend Raul, a young black man who lives in the Virgin Islands. They were cutting grass next door while I was puttering around the pool. I had glanced over there more than a few times. The boys were wearing cutoffs that revealed their bulging muscles. I was probably gawking too often. Val's parents were at work and the two guys were horsing around, mainly just playing grab-ass.

  I was wearing my string bikini and had just settled on a chaise to get some sun. Val came up to the fence and asked if he and Raul could take a dip in the pool. I said, “Sure, and bring over a few beers.” In less than a minute the boys were on my patio with a full cooler. We all popped a top and jumped into the pool. We finished off our beers and they started ducking each other. They soon grabbed me and under I went. I felt a hand on my ass as I went under. I thought it was accidental until they ducked me again. This time I felt a hand on my ass and one on my tit. I didn't say anything about it to the two guys, but they had my juices flowing.

  I got out of the pool and had another beer. The boys soon followed. We sat around drinking. Val asked if I ever swam in the nude. I said, “Once in a while at night, when it's dark.”

  Val said, “How about now?” He and Raul pulled off their cutoffs. Before I could say anything, they had me standing up and out of my bikini. I glanced at their cocks. Both were hard and big. This all happened in about fifteen seconds.

  They picked me up, and into the pool I went. When I came up, Val was behind me, holding me by my tits. Raul was in front with his hand on my pussy. I started to say, “Knock it off,” but Raul covered my lips with his and Frenched me. I was turned on since it had been a month since I had had any loving. They kept playing with my body. Val said, let's get out of the pool. Raul got out and lifted me up on the edge and gently pushed me back. My legs were still in the pool. Val got between them and started eating my pussy. I was so hot I couldn't hold back, and I flooded his mouth with my first orgasm. Raul straddled my chest and offered his cock to my mouth. His cock was at least nine inches long and the head was the size of a plum. I had a hard time getting it in my mouth. I licked all around the head and soon had him moaning. My cunt was on fire, and I shot off again.

  I soon had Raul fucking my mouth. I was getting more and more cock down my throat. My husband never shoots his load in my mouth, so when Raul said, “Here it comes,” I thought he would pull out; but he didn't. He shot his load down my throat. He shot so much I had a hard time swallowing it all.

  Val said, “I want to fuck you, Audrey,” and carried me over to the chaise. I sat down on it with my legs over the sides. My cunt was wide open. Val got between my legs and told me to put his cock inside me. He was almost as big as Raul. I put the head at my opening and humped my cunt, taking most of it. He fucked like there was no tomorrow. He lasted about two minutes before he said, “Here it comes.” I felt his cock pump as his come flowed in me.

  Then it was Raul's turn. Val stepped aside and his friend took his place. He put the head at my cunt hole and pushed. It felt like a tree trunk was being pushed in me. My cunt felt like it was spread as wide as possible. I said, “No, Raul, it won't go.” He just flexed his hips and grabbed my ass. Once the head was in, the rest of his cock followed. I could feel every inch as it slid into me. His cock was so big that the top of it rubbed my clit. I started to come—in fact, I don't think I ever stopped coming. His cock was way up in my belly when he shot his load. He kept fucking until he got soft.

  I could feel cunt juice and come running out my hole, so I jumped into the pool to wash off. When I came out, the boys handed me a beer. In between sips the boys would kiss and play with my tits and pussy. Raul was fingering me and Val was sucking on my nipples. They sure knew how to turn a girl on. I had a hand on both their cocks. Raul said, “Let me lay down and you sit on my cock.”

  I said, “Okay, but let me put it in myself. I'm still a little tender.” I straddled his cock and put the head at my hole. The head went in easier this time. God, his cock was big. I took in about half on my first try. His cock filled my love canal. I fucked up and down and soon had him in up to his balls. He started fucking me nice and slow. His cock was rubbing my clit, and he soon had me coming.

  Val said, “Pull her down to your chest.” Raul did. Val then got behind me and started fingering my asshole, rubbing my juices into it. After he had me nice and wet he stood up. He put his cock at my asshole and eased it in. Thank God I had been fucked in the ass a couple times in my life before that day. It hurt at first but soon I was into it, fucking back at his cock. They were both fucking my holes. It was a first—what a sensation! They soon had me coming and coming.

  We fucked for a good fifteen minutes before Val said, “I'm coming,” and Raul said, “Me too.” Both their cocks swelled up and I could feel their spunk shooting into me.

  It felt so good I almost passed out. They kept fucking until their cocks got soft and slipped out of my holes. Juices ran out of my cunt and ass and down Raul's balls.

  I was limp as a rag. We just lay down and caught our breath. We finally got up and jumped in the pool. I told the boys it was getting late and reminded them that my husband would be home soon.

  As they left, they asked if we could use the pool again. I said, “Sure, anytime.”

  Well, since then, I've been sucked and fucked twice a week all summer long. I'm sure going to miss those boys when school starts up again.—A.B., Orlando, Florida

  MAKING LOVE IN A CHEVY VAN

  I am not an American, but I have lived here since a young age. I've been married to a good-looking woman for eleven years, and had never made love to anyone else until just recently.

  Two Sundays ago I was in my car dealership, answering calls on a few ads I had placed in the paper. It was raining and it was a very slow day. There was no one there but me. The phone rang around one, and this sexy voice asked me about the van I had listed in the paper. I told her all about the van, and she was very interested. My dic
k started to jump when she said in a lusty voice that she'd be over in a flash.

  I went back to reading my latest copy of Forum and forgot about the time. When I finally looked up from the magazine, I saw this very good-looking woman standing in front of my desk. She saw the book in my hand and with a smile said it was she who had called about the van.

  I gave her the key to the van she wanted to test-drive, and after twenty minutes she pulled back into the lot and came into the office. She wanted to look around the inside of the van and, since it was still raining, she asked if she could drive it into the shop.

  I opened the door and she pulled in. Inside the van she asked me the few questions she had and told me she'd really like to buy it. When I told her the price, though, she said she was live hundred dollars short. Before I could say, “It's okay. You can have the van for the cash you have,” she started rubbing my hardening dick. In a flash she pulled my zipper down, freeing my aching cock. When her eyes opened wide, I knew she was pleased with the size of my dick.

  She slowly put her mouth around my pole and started to suck me off, taking half of my dick down her throat, rubbing my balls with her hands. The fact that a woman other than my wife was sucking my dick got me harder than usual. I moved her to the floor of the van and we got into a 69 position with her on top. As I was eating that young pussy, I thought of something I wanted to do that I had never done with my wife: I wanted to fuck this woman up the ass.

  I put my finger in her asshole while I ate her pussy, and she moaned like I had never heard before. By now she had all nine inches of my pole in her mouth and working it like there was no tomorrow. I was certainly ready to come, but I pulled out of her mouth and told her I wanted to fuck her doggie-style.

  I went behind her and entered her wet pussy, slowly shoving my dick into her, pumping her pussy faster and faster. She came in no time.