Letters to Penthouse XXI

by The Editors of Penthouse Magazine

  IF ONLY SHE’D DONE THE LAUNDRY, HE’D HAVE NEVER TRIED OUT HER CLOTHING

  If I had done that laundry, this adventure that changed our lives never would have happened. This letter is the story of how things worked out.

  My husband and I are both bicycle enthusiasts. Earlier this spring, one Saturday morning as the weather was just starting to get a little warmer, Chuck decided he wanted to go for an early ride. I was trying to sleep in that morning and heard him mumbling and rummaging for something to wear. But he didn’t say anything, and he seemed finally to find what he was looking for, so I just went back to sleep.

  Chuck: Even before we were married, Jennifer liked to wear my clothes. She was always “borrowing” one of my sweaters, or a shirt, or maybe a jacket. Sometimes even a pair of shorts or jeans would get “borrowed.” One time she even helped herself to a pair of my boxer shorts—and wore them in bed.

  I only complained once. It was a year or so after we were married, and one day I realized that every stitch she had on was mine. Now it’s true that we are kind of close to the same size. I’m five-eleven and have a medium build. Jennifer is only an inch shorter, and is athletically built. But still.

  “How would you like it,” I said in exasperation, “if I wore your clothes?”

  She shrugged and answered without a pause, “Anything you can fit into, you’re welcome to wear.” I didn’t have a comeback for that, so I kept still.

  Life went along more or less normally until one chilly morning last spring. Jennifer hadn’t gotten around to doing the laundry, and I didn’t have any clean biking tights. It was still too cold for shorts, so I ransacked the drawers and closets for something to keep me warm. I found a pair of her black leggings.

  I wonder if they’ll fit, I thought, as I pulled them on. Not bad, I decided, as I admired my flat stomach and hard, round backside in the mirror. They felt great, and they really hugged my legs. So I grabbed my helmet, zipped my jacket and headed for my bike.

  Jennifer: A couple of hours later, I got up and took a leisurely shower. Then I put on one of my last pairs of clean panties and one of my husband’s T-shirts. The T-shirt was loose on me, and hung like a micro-miniskirt. It was just long enough to cover my panties—most of the time.

  I just love to wear Chuck’s clothes. We are pretty much the same size, but his shirts and sweaters are just a little bit roomier than my girl’s clothes. Besides, there’s just a hint of male musk in the fabric of his things that’s always been a turn-on for me.

  I was in the kitchen making coffee when he got back. I asked him, “How was your ride?”

  “Great,” he said, as he poured himself a glass of juice. “You really should have come along.”

  I put my arms behind my neck and stretched. The T-shirt pulled up, giving him a good look at my animal-print bikini bottoms. It was also obvious from the way my boobs were moving under the shirt that I hadn’t bothered with a bra. I could tell from the bulge in his tights that I was having the desired effect.

  “You look so good in tights,” I said, patting his bottom.

  Except, I discovered, they weren’t his tights. They were my leggings!

  “Wait a minute,” I said. “What are you doing in my clothes?”

  It wasn’t that he looked bad wearing my tights. In fact, his muscular legs and firm butt looked pretty damn good. It was just so unexpected.

  He immediately became defensive. “Hey,” he said, “if you’d done the laundry, I’d have had my own tights. Since you didn’t, I borrowed your leggings to keep warm. Like you’re always borrowing my things. In fact, that’s my T-shirt you’re wearing right now!”

  I took my coffee and headed for the bedroom, shaking my head. I found some jeans and put them on. Suddenly I had an idea. It was a wonderful, wicked idea, and the more I thought it over, the better I liked it.

  I picked up my mug and strolled back in the kitchen.

  Chuck: I had finished my juice and was trying to decide what to have for breakfast when Jennifer came back in the kitchen, carrying her empty coffee mug. She headed for the coffee pot.

  As she refilled her mug, she said, “You know, I think you might be right.” She blew on the coffee. “I have been selfish about sharing my things. There’s nothing wrong with you wanting to wear my tights. As a matter of fact, you look fucking awesome!”

  She paused to let me think it over.

  “Most of my things are kind of unisex,” she went on, “and we’re close enough to the same size that they should fit you.”

  It was my turn to shake my head. I said, “What are you telling me?”

  “Just that I think it’s fine if you want to, you know, wear my clothes.”

  She melted in my arms and hugged me. “I do draw the line at sharing underwear, though,” she purred. “We’ll have to go shopping for panties for you as soon as you take a shower.”

  “I don’t want to wear panties!” I protested. “Yours or my own.”

  “Don’t be such a tight-ass,” she said. “You men have such a hang-up about your fucking underwear. How can you be so uptight about something so boring I will never understand. Besides, it is underwear, after all. Nobody needs to know whether you’re wearing nylon or cotton or whatever.”

  Jennifer: He looked at me like I was losing my mind. “If it’s no big deal,” he said, “then why do we need to go shopping for lingerie?”

  I rolled my eyes and thought frantically for some kind of a comeback. Finally I said, in feigned exasperation, “If we’re going to share clothes, it has to be from the skin out.”

  That didn’t even make sense to me, but Chuck seemed to buy it. We untangled, and he headed for the shower. I wondered if I really was going to sucker him into buying (me) some women’s daywear.

  I took him to my favorite department store and led him to the lingerie department. Men always seem nervous when they pass by racks of bras and panties, and my husband is no exception. Are they afraid people will think they’re perverts if they like pretty things? I’ll have to ask him sometime.

  Chuck: None of this makes any sense, I was thinking as I headed for the shower. All I wanted to do was stay warm on my bicycle ride. I’m not sure how it happened, but the day was certainly taking a strange turn.

  Anyway, we went to the mall and wandered into a large department store. Jennifer knew exactly where to go, and led the way to the lingerie department. Like most men, I’ve always been a little embarrassed when I’m surrounded with racks of nylon. It was a bit easier having my wife with me.

  “I’d say you look like a size six,” she said. “You see how the sizes are shown on the tag?” She was preparing to leave me on my own (after I finished shopping, I was supposed to meet her in the food court), but after she took a few steps, she turned back to me and said, “Don’t get all one kind. Shop for some variety.” Then she was gone.

  The variety part was easy. Panties come in half a dozen styles. There are bikinis, hipsters, high-cuts and briefs. Some have lace trim at the top and some have panels. Some have floral prints. Others come in a rainbow of colors. There are panties in nylon, satin, cotton and some fabric that’s a combination of cotton and nylon.

  By the time I’d picked out six pairs, I was turned on from handling the sensuous fabrics, and thinking how I would look in various styles, and how they would feel snuggling my butt and cradling my dick and balls.

  Jennifer: When I abandoned Chuck to his acute embarrassment among the bras and panties, it was all I could do to keep from laughing out loud.

  I was feeling kind of randy, so I went to another department store in the mall and bought myself a black garter belt and some nylon stockings. On the way to the food court, I saw a lovely black bra and decided to add that to my wardrobe. Usually I’m a 36C, but this time I got a 38, just in case Chuck needed something else to “share.”

  I thought he would be in the food court waiting for me, but I had time to finish a latte before he showed up. He noticed my packages.

  “What
’d you get?” he asked.

  “I’ll show you later,” I said. “Now I want you to pick one of the pretties you bought and go put it on.”

  “Do I really have to do that here?” he said. “I mean, really, can’t it wait until we get home?”

  “I was just guessing your size,” I explained. “You need to see if they fit.”

  He slunk off to the men’s room, and I reflected that it might have been a mistake for me to insist he try the panties on. If they didn’t fit, he would want to exchange them for a size that wouldn’t fit me. I could fix that, though, by just offering to take them back for him—and keeping them instead.

  Chuck: I could see that Jennifer had a point about trying the things on, so I took my shopping bag and headed for the men’s room. Hidden in the last stall, I hung my pants on the door and slipped a pair of black nylon high-cut panties up my legs. They fit perfectly, and felt incredibly sexy on my erect cock. I squeezed my bottom through the slippery fabric the way I do Jennifer’s, and my dick got even bigger. As I rubbed it through the nylon, a drop of precome soaked through the material.

  Can’t take these back now, I thought as I removed the tag. On the way back to the food court, I dropped my old cotton briefs in the trash. Jennifer was right. Men’s underwear is boring.

  Jennifer: Chuck came back to the table all smiles. “You were right,” he said. “They fit perfectly. And you have no idea how sexy nylon feels.”

  “Actually, darling, I do,” I corrected him, arching an eyebrow. If he noticed, he didn’t give any sign of it.

  I was ready to go home, but all of a sudden Chuck wanted to shop more! So that morning we went to two more department stores and ended up at Victoria’s Secret. By the time we got home, I think he had more panties than I did! This day was getting very strange.

  Chuck: After we had made the rounds of the lingerie departments at two more stores plus Victoria’s (and now my) Secret, the charge card was feeling the pinch. But I felt so sexy in my new panties, it was all worth it!

  When we got home, Jennifer said, “Okay, let’s see what you got. Start with what you have on.” I took my pants off, and she had me turn all the way around. “Good choice,” she aid, nodding approvingly. “We’ll come back to those. Now model the rest for me.”

  First I put on a white nylon hipster. “Not terribly inspired,” she said, “but an improvement on what you usually wear.”

  Next was a white ribbed satin highcut. “Better,” she said. “You might be getting the hang of it.”

  I put on a red nylon bikini. “Yes!” she said, as she patted my bottom.

  Eventually we got through the colors to the cotton-and-Supplex animal print from Victoria’s Secret and a floral-print panty with lace around the top. “My, you did get daring,” Jennifer purred.

  Jennifer: At that point I said, “Now it’s time for what I bought us.” I opened my shopping bag and brought out the black garter belt with the lace trim, the stockings, and the black lace bra. Chuck looked doubtful when I handed him the garter belt.

  “I thought we could share these things,” I said. “Try this on with the black panties you started with.”

  “How does this work?” he said.

  “There are two ways you can wear a garter belt. You can put it on over your panties like this.” I showed him. “That’s how mothers teach their daughters to dress. Or you can put on the garter, then the panties.”

  “What’s the difference?” he said.

  “For one thing,” I said, “there’s less to slide down when you have to pee. That means you have less to rearrange afterward.” I smiled a wicked smile. “The other reason is that men seem to like to be able to get your pants off and leave the stockings and belt on when, you know—” I blushed.

  He put on the belt and rolled the black stockings with lace tops up his legs. I had to help him with the snaps on one side, but he was able to do the other himself. He put the black panties back on and turned slowly while I admired the effect. Then I rubbed his cock, which was straining against the slippery fabric, and gave his balls a friendly little squeeze.

  “I had to guess about the size of this, too,” I said, handing him the lace bra.

  I’m not sure how he learned to do it, but he put on the bra like he had been wearing one for years. He stood in front of the mirror and turned from one side to the other. I knew what was missing. I pulled a wad of tissue from the box next to the bed.

  “A trick girls learn in eighth grade,” I said, as I stuffed the cups of the bra. That looked better.

  I wondered, How far would this go? When would Chuck say, “Enough”? I decided to push things a little further. I went to my closet and picked out a blouse and a denim skirt.

  Chuck: She said, “Try the blouse on first.” For the first time, I was confused. Men’s shirts button left over right; women’s are the opposite. The blouse turned out to be too small anyway, so I opted for a shirt of my own. Then I stepped into the skirt, pulled it around my waist and zipped the back. It fit perfectly.

  “You look pretty good,” Jennifer said. “A tan skirt would go better with the black nylons, and you’ll want a blue shirt, I think.”

  I changed and saw that she was right. For the next hour, we tried on everything in her closet. My favorite was a black velvet party dress. I have to say that when it comes to clothes, women have all the fun.

  Jennifer: The last thing I zipped my husband into was my black velvet party dress. I stood behind him and watched his reflection in the mirror. With a little makeup and a different hairstyle he would be a beautiful woman. The idea filled me with the strangest feelings. It was as though I had found a whole person in Chuck, a female alter ego.

  “We should have been sisters,” I said wistfully.

  “But then we would have missed out on all that great sex,” he said.

  “Oh, there would’ve been great sex,” I said. “Just not with each other.”

  I was getting horny as I caressed his breasts and rubbed my hips against his kind-of-feminine butt.

  “It could still happen, if you don’t mind doing it with another girl,” he said.

  I thought about what happened with my roommate my freshman year in college, then said, “I did think about it, sometimes.” Then I quickly lied, “I never had the guts to do it, though.”

  “You could do it with me in girl’s clothes,” he said.

  It didn’t take me a minute to decide. “We’ve done enough other kinky things today,” I said. “Make love to me any way you want except with your dick.” I was dripping between my legs. I don’t think I’ve ever seen Chuck’s dick get so big. It was peeking out of the top of his panties, oozing precome. He put my tan skirt back on and padded out of the bedroom. While he was gone, I closed the curtains and lit some candles.

  Chuck: I told Jennifer I’d be right back and went to the kitchen to retrieve a bottle of Asti from the refrigerator. When I got back, she was getting into the little black party dress I’d just taken off. This was going to be good, I knew.

  We sat together on the bed, and I poured us both some cold Asti. “Here’s to love and a communal wardrobe,” I said. We touched rims and drank.

  “When I teased you about wearing my clothes this morning,” she said, “I never dreamed you would do it.”

  I said, “Until I tried on panties for the first time, I didn’t know how sexy they would make me feel.”

  “This has been quite a day for firsts,” she said. She took a sip of her wine. “I still can’t believe how good you look in my things.”

  I set my glass on the nightstand and put my arms around her. She hugged me back, and our boobs flattened against each other. I brushed her hair away from her neck and kissed her there. Then I took her hand and put it on my breast. In the lace bra, my nipples were hard and sensitive.

  While she was feeling me through my silk blouse, I slid my hand along her leg. After another long kiss, I unzipped her dress and slid it off her shoulders. She undid the buttons on my blouse.
It was strange to see the cups of my bra emerge as the blouse came open. I fondled her tits through the smooth white nylon of her bra. The nipples became erect under my fingers, and she closed her eyes. One strap slipped off her shoulder, and I pulled the other down. Without unhooking the bra, I pulled down the cup, exposing her large, firm melon with its hard brown nipple.

  I took my time kissing her from her neck to her nipples. She squirmed under me in anticipation. Then I took a sip of Asti and sucked her hard berry into my mouth. The cold wine made her gasp, and her nipple grew even larger in my mouth. She lifted her hips for me to take her dress off. Then I stood beside the bed and unzipped my skirt. I let it fall to the floor and stood there wearing only a bra, panties and nylons.

  Jennifer licked her lips, and I climbed back on the bed. She was still wearing her panties and bra, and I wanted to leave them on just a while longer. Don’t women always complain that men are in too much of a hurry when it comes to sex? Well, I was determined that Jennifer was going to beg me for it.

  I got a bottle of lotion from the nightstand and shook some in the palm of my hand. Starting with her feet, I gently massaged each toe, then worked my way all the way up her tights. When I got to her crotch, the nylon of her underpants was wet and she was moaning in anticipation.

  “Roll over,” I said. “I want to do your back now.”

  She rolled over. I put one knee on each side of her hips and gently rubbed my aching balls on her round bottom. I knew that she could feel my stiff dick through her nylon panties, because she was pressing her ass hard up against my crotch. I pushed back and thought about giving up this game and sticking my throbbing cock in her cunt as far as it would go! But she had said that she wanted me to love her like a woman, and I was determined to be a lesbian for her. So I unhooked her bra and finished rubbing lotion on her back.

  When I finished, she rolled on her back and hissed, “I want you!” She was out of her panties in a second and spread her legs for me. “Eat my pussy!” She pulled my face against her crotch. I parted the lips with my tongue and licked the blood-gorged and sensitive clitoris standing at rigid attention. That was all it took to trigger her explosive first orgasm. For a full minute, her snatch kept clutching and she held my face tight against her as she gushed in my mouth.