Letters to Penthouse XV

by Penthouse International

  At last she slowed down, still squirming around my flaccid cock, unwilling to let it slip out until the last second. I was drained, and she was exhausted. It was the best sex we had had in years. When we recovered, Grete released me from my corset and we slept through the rest of the storm, until we awoke to a bright and cheerful morning.

  We had both slept in our clothes. My bra was still on, but the grapefruit had rolled out during the night. I was oddly reluctant to remove my blouse and skirt, but after our recent orgy they were certainly in no condition to wear.

  I kissed my wife and thanked her for her wonderful surprise of the night before. I was wondering if she would be offended if I told her I would like to continue exploring my feminine side for a while. But she beat me to the punch.

  “You enjoyed my little surprise a lot, didn't you?” she asked.

  I admitted that I did, and she began to caress my chest, tweaking and stroking my nipples.

  “Enough to go shopping again today—for you?”

  I agreed rather eagerly, and Grete laughed, saying, “I hope I haven't created a monster!”

  I had never really enjoyed shopping before, but with Grete's help I happily browsed through the racks and bins at several second-hand stores in the town, after which she helped me pick out some bras and panties at a nice anonymous mall. I was scandalized by the price of pantyhose, but we bought a few pairs anyway. I was tempted by the wigs and makeup and all the other goodies, but Grete convinced me to wait and see how much I liked dressing up before we spent too much money. So far we were out less than it would have cost to spend a day at your typical tourist trap, and I had a nice beginning wardrobe.

  I could hardly wait to try on my new clothes when we got home, and Grete helped me with great amusement. I had watched her get dressed for many years, but somehow I had never learned all the little tricks of the trade, such as how to match colors, or whether to put on the panties or pantyhose first. She showed me how to adjust a bra strap, demonstrated the correct placement of my skirt waist and chortled as I fumbled with the reversed buttons on my blouse.

  When I was done I felt great, but I wondered what to do next. Grete suggested a walk on the beach, and I agreed. But when I opened the door, I was hit with stage fright. What would I do if someone saw me like this?

  Grete laughed and pointed out that we were out here in the middle of nowhere. Who was going to see us?

  So we strolled the beach, and I found I enjoyed walking in a flowing skirt, feeling it wrap around my ankles and sway in the breeze. We walked hand in hand along the sand until we came to a spot where the land jutted out into the sea, forming part of our secluded cove. We climbed carefully through the scrub woods to see what was on the other side, but there was nothing but more beach, so we turned back.

  I was still new to wearing a skirt, so when it caught on a branch, it was down around my ankles before I knew what was happening to me. I immediately tripped over it, and found myself in an undignified position, hanging over a branch with my panty-clad tush high in the air. The next thing I felt was Grete's hand groping at my ass.

  “Hey, sweetie, you want to try it hanging from a tree?” she giggled.

  With her hands slipping between my legs, I rather thought I did!

  I was glad I had taken Grete's advice and not worn pantyhose, because her hands were soon all over my rapidly growing prick. I hated to interrupt this, but my position was growing uncomfortable. I wriggled off the branch and lowered myself to the ground, and Grete quickly raised my skirt and took my rod in her mouth.

  In no time she had sucked it to life, and she was soon bobbing eagerly up and down over my rod. She tugged at my panties and began to play with my balls, gently cupping first one and then the other. I clasped my hands beneath my wife's head and watched her enthusiastically sucking me off.

  Once again the feel of my bra enhanced my response, each pull of the straps or shifting of the grapefruit bringing new delights to complement the sensation of Grete's skilled lips. Her long hair fell sensuously over my thighs, brushing them teasingly as her head rose and fell on my member.

  I wanted this pleasure to last, so when I felt myself getting ready to unload, I pulled away and wiggled into a new position, licking at Grete's slit to return her favor. She was really hot; my slightest touch made her growl and moan. I abandoned subtlety and headed straight for her clit, sucking and licking for all I was worth. Within seconds she exploded in orgasm under my probing tongue.

  Since there wasn't really room to lay her out, I rose and puller her up, pushing her skirt down to the ground. I lifted her up and lowered her on my prick, fucking her standing up in the woods. The crotch of her panties got in the way, so she simply ripped them away to allow me to plunge my pecker in her without any obstruction.

  She grasped a nearby branch and pulled at it as she slid up and down on my rod, her legs wrapped around my waist. She was as wet as I had ever felt her. My boobs bounced in time with her as we fucked each other, my prick a rod of steel plunging into her depths. When I came, it was stupendous, juices spurting in great jets, filling her with my cream.

  I held her as long as I could, then lowered her slowly until her feet were on the ground. We stood there supporting and caressing each other for long minutes. Then with a laugh I picked up her skirt and handed it to her, and she handed me mine.

  It's fall now, and we are back at school. I miss the seclusion and freedom of that cabin, where I could dress up anytime I liked with no one around to see me, but being back in civilization has its advantages. Grete is teaching me about makeup and deportment, and I did buy a nice wig recently.

  As a computer jock, I naturally turned to the Web, where I have found all sorts of information about crossdressing. It turns out that there's a group right here in my town. Who knows, one of these days I might just call them up!—Name and address withheld

  THEY DO IT ON A WAR MONUMENT, AND THEN SAY TANKS FOR THE MEMORIES

  I met Carla ten days ago, but already she has changed my life. I thought I liked fucking, but I didn't know what I was missing until I met this hot vixen. She is in her early twenties, and has a body any man would leave his girlfriend or wife for. She is tall, and has naturally wavy blond hair that's just long enough so that it reaches the tops of her big dark nipples. The great thing about Carla is that she isn't skinny, like so many girls you see nowadays who starve themselves into skeletons. With her strong shoulders and thighs, I guess you could say she is athletically built. To all you women out there who think you have to be scrawny as a supermodel to get a man, let me say that a real man likes to fuck a soft, warm body, not a bag of bones. Carla isn't fat at all, but she has flesh on her bones, and classic curves in all the places a woman was meant to have them.

  I could go on describing the way Carla looks, but I'd rather just get to the good part. The thing I found out about her right away is that she likes to fuck in unusual places. I don't mean like the bathroom or on the top of the stove or on the steps leading down to the basement of the house she shares with her two roommates. Actually, we have fucked in all those places, and of course the sex was always intense, because Carla is so fucking wild. But the unusual places I'm talking about are public places. Carla likes to have her pussy pounded out in the open, where there's always a chance people will see her. Since we've been together we've done it on the hood of my car in the parking lot of a local supermarket, on a couch in a dark corner of a cafe, and once on the back seat of a bus as it cruised through the Lincoln Tunnel.

  I'd never been with an exhibitionist before Carla, and I admit I was shy at first. It felt weird knowing that people— maybe even someone I knew—might see me sticking my dick into this torrid fox. I also worried that we might get caught by someone who could make life difficult for us. I remember the first time we fucked outside. It was in a park which happened to be right next to a police station. I asked Carla what we would do if a cop came by. Her answer was, “Just stick that big cock back in your pants and run like hell.�
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  That first time is etched pretty deeply in my memory. Now, you might not think fucking in a park is all that unusual. But this park happened to have an old army tank in one corner, which was bolted to a big slab of cement as a monument to all the guys in our town who fought in World War Two. Over the years, the tank had become a favorite hangout and place to party. So early one morning, when Carla suggested we roll a couple of joints and head for the tank, I didn't think anything of it. But as soon as the weed started to kick in, I looked up to see that she was slowly lifting her T-shirt over her head. The pot was good, but I knew I wasn't hallucinating. Those were really Carla's big tits and saucer-sized nipples that were staring me in the face. There was a bit of an early morning chill in the air, and her nipples were taut as little brown marbles. Of course just looking at them I popped a woody a foot long.

  “What are you doing?” I asked Carla.

  “What does it look like?” she said. “I'm getting ready for you to fuck me.” With that, she climbed on top of the tank, stood on the hatch (which the city had years before welded shut), and kicked off her shoes. Wiggling her ass, she unbuttoned her jeans and slinked out of them. I whooped aloud as she gave me a private strip-tease, then remembered that the police station was only fifty yards away, and quieted down. I couldn't believe what was happening, and to be honest I wasn't sure I was going to be able to go through with it. But Carla was already completely naked and standing on top of the tank. She had one finger inside her pussy, and another planted lightly on the bud of her clitoris. Her head was tossed back and her legs spread apart as she fingered herself in the morning air.

  It was about eight o'clock and there were a few people in the park, joggers and mothers with strollers, but the paths were shielded from us by a row of bushes. But I was already so focused on the hairy bush in front of me—Carla's—that I didn't care who might come by. “Take off your clothes!” Carla told me, “It's getting cold up here. Or should I say it's getting warm?”

  As I dropped my jeans and pulled off my shirt, I heard Carla let out a squeal. I looked up to see that she'd worked her way over to the gun barrel that extended about ten feet from the tank, and was straddling it in all her naked glory. “Oooh, yes, yes …” she whimpered as she worked her bare cunt lips against the cold green metal shaft. There was nothing to do but to climb onto the tank to join her, because in truth it was pretty hot watching her fuck that long green rod. She wrapped both hands around it and rocked back and forth, jerking her body with quick movements and driving herself wild. I could see steam rising up from the tank barrel where her warm cunt juices had bathed it. She slid back and forth quickly, little grunts of, “Uuh! Uuh!” pouring out of her mouth as she moved to and fro, and now from side to side, on the barrel.

  The tank metal was cold, but it felt surprisingly great against my ass as I made my way down the barrel to join her. Carla was still masturbating against the tank, with her back to me. The barrel of the cannon looked like an enormous dick between her legs, and I know that if it were possible she would have taken every inch of it inside her. As she bopped back and forth, I pushed gently at her back, and she bent forward until her head was practically touching the barrel. She gasped as I moved a hand down her back, then let out a cry of delight as I pressed against her anus with a fingertip. She backed up, little by little, until my entire finger was buried in her ass. Moving harder than ever against the tank barrel, with my finger jammed up her chute, she started to growl passionately. “Yes … yes!” she exclaimed. “I'm … to … I'm coming! Coming!”

  Carla's cries of orgasm echoed through the park. I expected the police to come running over at any minute, but somehow I didn't care about that any more than Carla did. I moved forward on the barrel, wrapped my hands around her waist and pulled her on top of me. It was a delicate balancing act, but her cunt was so wet she sank down easily on my stiff seven inches. I pushed hard into her, thrusting inside her warm pussy. If you had told me fifteen minutes earlier that I would soon be stark naked and fucking my girlfriend on the barrel of a tank gun in the middle of a public park, I would've said you were crazy. But now I was doing it, and I'd never felt better. Carla's cunt was tight, and as she clamped her legs around my thighs, her pussy lips squeezed even tighter around my prick.

  Then she did something really incredible, and probably dangerous too. She leaned forward, making sure not to let my dick slide out of her. “Hold on tight!” she said, and stretched her arms out in front of her, grabbing hold of the barrel. “Stay inside me. Your cock feels so fucking hard!” she sighed, as she stretched her legs out behind her. By now I was holding on for dear life, but it was a hell of a ride. It took a couple of seconds for us to get our balance, but there we were, fucking doggie-style on the barrel of a tank gun. With only a few inches of metal to hold onto, we were totally wrapped up in each other, trying to keep from falling. But the fit was amazingly tight, and in less than two minutes I felt my balls about to erupt.

  “Hold on to the tank,” I warned Carla. “I'm about to come!” She clutched the barrel with both arms, and I clutched her. My whole body shook as though in a hurricane as the seed pumped out of my nuts and into Carla's moist pouch.

  It took a little acrobatic work on our part to get down from the tank without tumbling to the cement below us, but we managed. With both of us still naked, Carla was ready for another round. She started to pull me by the dick toward a bush, but suddenly we saw a cop making his rounds, and decided to get out of there before he spotted us—although for all we knew, he'd been watching us on the tank the whole time!—F.D., Clifton, New Jersey

  HE HAS A THING FOR TINY TITS, AND HIS WIFE FILLS THE BILL, IF NOT THE BRA

  My wife and I enjoy reading the stories in your magazine each month and trying to re-create them ourselves. My wife, Karen, absolutely lives to fuck, and is not against trying anything, including other women. She is nothing short of gorgeous, though very much on the skinny side, and has enjoyed other women since she was in college.

  I happen to be one of those guys (and there are more of us than you'd think) who prefer women with extremely small tits, the tinier the better. Fortunately for me, Karen has nothing more than a pair of unusually long nipples on her gorgeously flat chest. Even when they're soft her nipples stick out a half-inch, and they actually bend over when she wears a tight top. Unfortunately, she never goes without a well-padded bra outside the house, so I'm the only one who can enjoy the sight of her unusually long nipples. She knows I love her flatness, so at home she always wears sexy little tops without a bra, or just goes topless for me. Needless to say, this leads to a lot of fucking.

  A few months ago I was in a nearby town on business and noticed a promotional sign at a strip bar that said, “Tiny Tops Night Wednesday.” I asked the waitress about it, and she told me that it was an amateur night for small-breasted women, who could get up and strip as long as they were an A-cup or less. There were some really good cash prizes for the best ones.

  I told Karen about this when I got home, and almost begged her to go there with me on Wednesday, and maybe join in. She agreed to go, but she said she wasn't about to show everyone her “flat washboard chest.” But knowing that in spite of her self-consciousness about her chest, she had a real exhibitionist streak and loved showing off, I figured that once I got her there I could probably talk her into joining in.

  When I got home from work Wednesday night, Karen was already dressed to go out, and she looked incredible. She wore red high-heeled shoes, a pair of white jeans that were so tight in the crotch you could practically make out the shape of her cunt lips, and a thin, stretchy white top that clung to every curve of her padded bra. She struck a pose and said, “You like?”

  “Absolutely gorgeous!” I said. “But why not leave the falsies at home? Please?”

  “Aw, sweetie, you know I don't like going out without tits,” Karen said. “How about if I take my bra off once we get there?” Reluctantly I agreed, and after a few drinks, we left.

&n
bsp; At the bar, as we had more drinks, I couldn't help but notice all the tiny tits and flat chests that surrounded us. Even our waitress, who was topless, had really small tits. They weren't as nice as Karen's, but she was very cute, and Karen seemed to find her sexy.

  After a while I reminded Karen that she'd said she would take her bra off when we got there, so after a little hesitation she went to the washroom to take care of it. She was gone for quite a while, which gave me a chance to really enjoy all the wonderful tiny tits that were on display. When she finally came back my eyes went right to the thin top that was now stretched across her flat chest, with her long, hard, dark nipples almost sticking right through the material. “I didn't realize this top was so thin!” she whispered. “You can see my nipples right through it!” I just smiled and nodded. Then I asked her what had taken her so long in the washroom.

  Karen blushed. “Well, uh, you know our waitress? Well, she came in and we kind of hit it off. She mentioned how there were so many cute, suckable little tits out there, and how she'd like to get a sexy pair of lips on her little nipples. I said I knew how she felt, and before I knew it we were in a stall sampling each other's nipples.”

  Needless to say, the idea of Karen and the cute waitress sucking on each others' little tits gave me an incredible hard-on in no time at all. “Oh yeah!” I said enthusiastically. “What were her nipples like? Did you like them?”

  “Mmmm! They were very sexy,” she whispered. “And so nice and thick, just like mine.” Just then the waitress passed by, pausing long enough to run her fingertips along Karen's shoulder and down across her tiny right nipple. Karen looked up and they smiled at each other.

  The manager now announced that there was going to be a wet T-shirt contest. I begged Karen to enter it, and she finally agreed, but stipulated that the T-shirt had to stay on. Those women who wanted to enter were told to go into the changing room, where they would be outfitted with T-shirts with the name of the bar on them. Karen went, and when she came out I smiled at her as she went up on the stage with about seven other women, including our waitress—whose name, Karen had told me, was June. As the audience cheered, the manager soaked each contestant's T-shirt down with a hose until they were dripping wet, which really emphasized their tiny tits. The breast sizes ranged from nothing at all (including Karen and a couple of others) to very small (including the cute waitress).