Letters to Penthouse XXVII

by Penthouse International

  As he did I started to come. I never thought I could climax without touching myself, but now I did. Even after I came I wanted him to go on forever, but finally he came also, filling my ass with more come than I had thought possible.

  After he had finished he pulled out and came around to let me clean him off with my mouth, which I happily did. At that point he told the crowd that the show was over, saying that anyone who thought they hadn’t got their money’s worth should come forward.

  No one did.

  —Name and address withheld

  SHE THOUGHT AMY WAS A GREAT GIRL,

  TILL SHE SAW HER STANDING UP TO PEE

  When I decided to return to college to finish my degree I found an apartment not far from the campus, in an old brick building with hardwood floors, high ceilings, and old-fashioned bathtubs. Being a female, I was a little worried about the neighborhood. But it seemed that a lot of students lived around there, and the people I met assured me that it was not as tacky as it looked. In fact the general opinion was that I had been lucky to find a vacancy.

  As I was moving my clothes and boxes from my car into my second-floor one-bedroom, I passed a young woman going down the stairs with a basket of laundry.

  “Where are the washers and dryers?” I asked.

  “Come on, I’ll show you.” I followed her to a room on the first floor that had four washers and two commercial-size dryers. I had some laundry to do myself, and I told her I would be back in a few minutes. When I returned with my dirty clothes we introduced ourselves. Her name was Amy, and she worked as an intern in an architectural office located downtown.

  “I’m Sally,” I told her. “I’m taking classes at the college this summer, and I’ll be full-time in the fall.”

  As I sorted out my clothes in preparation for loading them into the machines, Amy sat on the table and swung her long tan legs indolently. The rest of her was a golden bronze too, and she had short blonde hair and bright blue eyes. I’ll bet she drives guys right out of their fucking little minds, I thought.

  “I go up on the roof to tan,” she said, as if she had been reading my thoughts. “It’s a free show for the college boys in the apartment next door.” We laughed. I’ll just bet it is, I thought.

  “In fact, I was going to catch some rays this afternoon. We can get you a lounge and you could join me.”

  “Sure,” I said. “Why not?”

  After finishing our laundry we drove to a Kmart, where I bought a cheap plastic chaise longue, and we lugged it up the three flights to the roof. Then we each went to our room to change, agreeing to meet back there in a few minutes.

  When Amy came up to the roof she was wearing a yellow floral print bikini that I’d seen advertised in a Victoria’s Secret catalog. She was carrying a bottle of water with a teabag in it, which she perched on the parapet wall. Then she spread a beach towel on her chaise and fished in her bag for some sunscreen.

  “Want me to rub some on your back?” she offered.

  “Thanks.” I rolled onto my stomach and she massaged the lotion into my back and legs.

  “Do me?” she said when she was finished. She unhooked her bra and laid it beside the chaise. When I had finished oiling her, she rolled onto her back without bothering to put her top back on. Her large firm breasts were almost as tan as the rest of her. She squeezed some sunscreen into her hand and slowly rubbed it on her chest, massaging each mound and pinching her nipples.

  “One of the boys next door plays with his thing sometimes when I do this,” she said, smiling. “He thinks I don’t know, but I’ve seen him.”

  “You are an awful tease,” I said. Then I unhooked my bra and reached for the sunscreen. We both laughed at once.

  Over the next two months we became good friends. Amy introduced me to her hairdresser and gave me some tips about the neighborhood. I gave her a tour of the campus, and she showed me her office. We rode our bikes together on weekends. We cruised bars and frequented bistros, attended concerts and plays, and watched fireworks after a baseball game on the Fourth of July. Most nights we fixed dinner together. We were having such a good time with each other that I didn’t even really mind not having a boyfriend.

  There were some things about Amy, though, that occasionally puzzled me. Like the time I was foraging in her medicine cabinet for an aspirin. Something seemed to be missing—and then it hit me. Amy didn’t have any birth control pills, a diaphragm, or even a box of condoms in her bathroom. I couldn’t imagine a woman living on her own—especially someone as hot as Amy—who didn’t have some kind of protection handy. Maybe she has something in the bedroom, I thought.

  One Friday night Amy and I were fixing dinner at her place. We had had a few beers to start off with, and at one point I heard the call of nature. When I took my pants down in the bathroom I noticed that my period was starting. I looked around to see if I could spot some Tampax or pads or panty liner. Nothing.

  “Amy,” I called. “Where are the pads and plugs?”

  “What?”

  “Your period stuff. Where do you keep them?”

  “I’m out,” she replied.

  This surprised me. When I’ve used half a box I always buy another one. I pulled my pants back on. “I’ll just run downstairs and buy some,” I called to her. “Be right back.”

  When I eased back into the apartment Amy was in the bathroom. The door was half open, and glancing that way I saw something that made me gasp. Instead of sitting on the toilet with her pants down, she was doing something that should have been impossible. She was standing in front of the toilet, with the seat up, and pissing—with her cutoff shorts on. When she finished she flushed and put the seat back down.

  When she came out of the bathroom she caught me staring. “God, you scared me!” she said. Then she saw the expression on my face, and I could see her beginning to realize what had happened. Her face went pale.

  “How— Did you . . . Did you see?” she stammered.

  “I saw enough, yeah.” I was still taken aback and didn’t know how to react.

  Tears brimmed in her eyes. Her hand came up to her face, as if she wanted to hide from me. “Now you’ll hate me,” she whispered. “Oh Jesus!”

  “No,” I said. But I was still confused. “My God, Amy, how did you do it? I mean—you’re so pretty!”

  She smiled a little, and blushed. “Let’s sit down,” she said, and we moved to the couch and sat at opposite ends.

  “I’ve always known,” she said then. “Even in junior high, I knew I was really a girl.” She made a wry face and rolled her eyes.

  I waited.

  “This is my real hair, and my boobs and my hips. I started getting hormone shots my first year in college. No silicone or implants.” I just nodded, and she went on. “After the first year my body was becoming obvious, and I had to transfer to another college. I also changed my name. Originally I was Tom.” She wasn’t looking at me. “My family—particularly my dad—pretty much wishes I was dead.” Sudden tears streaked her cheeks. She took out a tissue to blow her nose. I moved closer to her and took her hand, trying to comfort her as she cried.

  “Hey, you’re my friend!” I told her. “I don’t care what’s between your legs.”

  She didn’t stop crying, but she reached out to hug me hard. I hugged her back, and I guess I was crying a little myself. After a while we drew apart, drying our tears and blowing our noses.

  But now I was curious as hell. “Amy, the—the bikini and the bike shorts and the tight pants—I mean, where do you put it? Your thing.”

  She looked hard at me. “Do you really want to know?”

  “Yeah, sure.”

  “It’s called a gaff,” she said. “The thing I wear to hide it. It’s like a thong, but with a little bigger pouch, and it’s thick like a bikini bottom or a support panty. The bikini and bike shorts are thick enough to hide it, since nobody is looking for it anyway. I just sort of tuck it between my legs and cinch it up.”

  I was fascinated. “Show
me.”

  “Okay,” she said. “Come into the bedroom.”

  In the bedroom she opened her dresser and took out something that indeed looked like a thong. She unzipped her shorts and shucked them down her legs, along with her panties. I couldn’t help staring at her penis.

  She stepped into her gaff and hitched it up her legs, tucked herself into the pouch, and pulled it tight around her hips. She retrieved her white panties from the cutoffs and put them on. Then she did a graceful pirouette so that I could admire her from all angles. She certainly didn’t look like a man.

  “Is that thing comfortable?” I asked.

  “There is a scrunch factor, like with an athletic bra. But you get used to it.”

  “Can I touch you?” I’m not sure what made me say that.

  “Yes,” Amy said. “If you let me touch you.” Then she added, “But it’s murder when I get a hard-on in this thing.”

  “You do that?”

  “Sometimes. When I’m with you,” she said.

  I didn’t know what to say.

  But I did want to touch her. My fingers skimmed the soft skin of her cheek. She had such fine, delicate, feminine features. I toyed with her pixie-like blonde hair, touched her pierced ears, and traced her neck. “You are so pretty,” I said.

  By now her hands were exploring me too. They slid over my neck and shoulders, and hesitated at my red halter top. Her eyes looked into mine, asking me a question. I nodded. She smiled, and a minute later the halter was on the floor. I wasn’t wearing a bra.

  I stood and unzipped my shorts, let them cascade down my legs, and kicked them away. Now we were naked together except for our panties.

  We moved together to the bed. Her lips were hard against mine, and our breasts squeezed together. My fingers slid down her back, and I rubbed the swell of her rounded bottom under the nylon underwear. On impulse I squeezed her ass hard, and she drew a surprised breath.

  “You’re killing me!” she hissed.

  “Then let it out,” I said.

  Amy lay on her back, lifted her hips, and shucked off her panties and the gaff in one fluid motion. I was looking at a woman with a dick, which was hardening into a respectable erection. A drop of pearly precome oozed from the slit. I licked it off and sucked her into my mouth.

  “Oh my God!” she gasped out. Then she spread her legs and arched her back with a guttural moan. Her hands clutched at my head as she pushed her hips against my face. I fucked her with my mouth, and in less than a minute her hips bucked and she wailed as her come erupted into my throat. I swallowed the thick, yeasty load in one large gulp.

  “Oh Jesus, Sally. . .” she panted. “You sweet thing!”

  Slowly we caught our breath. I lay down next to her and nestled close, my lips grazing her ear. For the first time I touched her breasts. They were firm and soft, with high, excited brown nipples. “Touch me,” I whispered.

  “Tell me what to do,” she said.

  “Have you ever made love to a girl?”

  “I’ve never made love with anyone. I’m a virgin.” This surprised me again. I kissed her tenderly on the lips.

  She kissed me back, and I opened my mouth in invitation. Her tongue explored tentatively at first, then with more urgency. I guided her hand to my boobs and gently caressed hers. My nipples were supersensitive, and hers were hard as erasers. They seemed to swell to fill my palm. While I toyed with her chest I kissed her again. She eagerly took my tongue in her warm mouth, and I sighed with tingling pleasure.

  As we turned on our sides to get closer, I could feel her getting hard against my thigh. Then she was on top of me, between my legs, pulling at my panties. I lifted my hips for her. When my panties were off she kissed my stomach, then the inside of one thigh, then the other. She paused over my mound.

  “You don’t have to,” I said. “It’s almost the beginning of my period.”

  “I don’t care. I want to. Your scent excites me.”

  I drew in my breath sharply as she found my hard little clitty. I hugged her with my legs, then spread them wide and arched myself against her face, then hugged her again. My orgasm burst over me like strobing fireworks that seemed to go on forever.

  We lay in each other’s arms in the afterglow. Amy played with my hair and I caressed her arm.

  “Sally?” she whispered after a while.

  “Yes?”

  “I want—that is, I’d like . . .” She nibbled her lower lip. “I want to put it in, but—but I want you on top. Like . . .”

  “Like a guy,” I finished for her. She nodded shyly. I smiled and kissed her.

  Amy lay on her back and I climbed on top of her, positioning my hips right above hers. I reached between my legs and guided her into me. We slid together with a simultaneous moan of pleasure. I brought my legs together between hers, trapping her deep inside me. This was going to be sex like I’d never experienced before—pretending to be a man making love to a man who really wanted to be a girl.

  I began to move my hips, thrusting gently. Amy lay still at first, but then her hips began rocking against mine, and I thrust harder. Her eyes closed and she began making panting, whimpering noises. I cupped her boobs with my hands and tweaked her nipples between my thumb and finger. She squirmed under me as I pumped. I could really learn to like being a guy, I thought.

  “Oh yeah,” she said. “Oh yeah! Fuck me!”

  “Come for me, baby,” I said, feeling an erotic surge at the masculine part I was acting. “I want you to come. I’m going to make you come! I’m fucking your tight little pussy, and I’m gonna squirt my stuff in your cunt, and you love it, don’t you, you hot little thing. You love getting fucked with my big cock! You’re going to come for me, aren’t you baby? Aren’t you?”

  “Yes!” she shrieked. “Oh God, I’m gonna . . . I’m . . .” Suddenly her arms tightened convulsively around me, and she grabbed my buns and shoved her hips hard against mine. I could feel her inside me, pulsing with release as she wailed and held me tight between her legs.

  Slowly we relaxed. “How was your first time?” I whispered.

  “Oh God! I think you might’ve turned me into a sex fiend.” She giggled, and we both dissolved in laughter.

  We spent the night in her bed, and in the morning we made love again. It seemed strange at first—not like lesbian love, and not like straight sex either. But we learned to love one another as people. We lived together for the next two years, until I graduated with my master’s degree, and Amy fell in love with a man and had the final surgery. But we still keep in touch, and I visit her, her husband, and their adopted daughter when I’m in the city.

  My love for Amy is something I could never explain. The truth is that I don’t really understand it myself, and I doubt if she understands her feelings for me any better. Still, we continue to care for each other. I guess what it comes down to is that it’s not how you love the person, it’s the person you love.

  —S.L., Tulsa, Oklahoma

  TO APPRECIATE MOTHERHOOD, TRY SEX WITH

  SOMEONE ELSE’S PREGNANT WIFE

  If you have ever wondered why porn videos featuring pregnant women are so popular, you should realize that for many men, pregnancy has its own erotic excitement. Most marriages produce at least one pregnancy, and generally speaking, some form of sexual activity continues throughout most of it. Interestingly enough, a woman’s complexion seems to glow during the nine-month process; her breasts get fuller, and many women experience increased erotic vigor. Many husbands like to take nude photos and videos of their wives during this period. Most wives are all right with this, and even proud to model their expanded nakedness. I know this is true because I have seen at least a dozen of my buddies’ private preggie pictures of their wives, and they’re usually pretty sexy.

  Unfortunately, there are still some assholes who think pregnant women are gross or unattractive. Pregnancy puts many demands on a woman’s body, and they have complex physical and emotional issues to deal with. This is a time when the mot
her-to-be needs extra tenderness and affection—and more. Which leads me to my story.

  Lauren was an attractive blonde who worked in our construction office. In addition to being sexy, she was hardworking and proficient, so she was respected by all of us.

  One day she proudly announced that she was pregnant, and that she intended to take an extended leave of absence to prepare for her child’s delivery.

  In the eighth month of her pregnancy she stopped by the office to check on her health insurance, and we talked for an hour or so. We had often kidded each other about our sex lives, and exchanged naughty jokes, but had never done anything intimate.

  I asked her about her life as a full-time housewife and potential mother, and Lauren started to cry. Then she told me that since she’d become pregnant her husband would not go near her, and had even gone so far as to sleep in the spare bedroom. She suspected that he was repulsed by the sight of a pregnant woman.

  “That’s crazy,” I said. “I think you are more beautiful now than ever. You really do have a glow—and your tits are absolutely spectacular.”

  Lauren blushed, but then she smiled and said, “Thanks, I needed that.”

  I am usually the last one to leave the office, and about three weeks after that conversation I was just going out the front door when a car pulled up and Lauren got out. I could see a look of determination on her face. Before I could say hello, she took my hand and pulled me into the office. Then she took my face in her hands and kissed me with incredible passion. In the midst of it she grabbed my crotch, to make sure she had my attention.

  After we completed the longest and sexiest kiss I’d ever had, she unbuckled my pants and pushed them down, along with my shorts, and with some effort went to her knees. She examined my already excited cock for a minute, then moved her mouth to it. As soon as she decided it was hard enough, she pushed me into a chair, pulled off her panties, and knelt on the chair seat, straddling my lap. She made certain that my dick was angled exactly right to slip into her hot pussy. She then took it in and rode me for ten wonderful minutes. When I fumbled for her tits, she opened her blouse and pulled up her bra to give me free access to her beautifully full breasts. She smiled when I sucked out some breast milk.