Letters to Penthouse XIX

by Penthouse International

  All right, Jerry! I thought. Not only are you losing your virginity, you just rocked this woman’s world! I had thought he would come quickly the first time, but no—he was still plugging away at that pussy like it was second nature, and my wife was about to come again.

  My own cock was rock-hard at this point, and when I reached down to get some relief, I filled my shorts within seconds with a huge load of come. That seemed to put them over the edge, and as Fran climaxed again, Jerry filled her cunt with his virgin seed.

  They lay there cuddling as I excused myself to change my shorts. Who says everyone can’t win? I thought to myself. Jerry just lost his virginity to a sexy lady who really cares for him. My wife got to realize her desire to take someone’s virginity. And I got to watch. Of course Fran and I still hadn’t done an actual threesome, but who knew what might happen when I got back? I was already planning another game of Truth or Dare.—B.N., Scranton, Pennsylvania

  HIS LUST FOR AN ASIAN BEAUTY EXPOSED HIM TO UNIMAGINED THRILLS

  I think it’s fair to say that I have elevated the seduction of women to an art. My creative energy is almost entirely devoted to it.

  At thirty-two, I am a professor at a prestigious university in New York City, where I also consult for high-tech firms and appear as an authority on national television. As a result, my income is well in the six figures. I drive a silver Porsche and dress with taste and style. My home is a meticulously furnished brownstone that serves as the ultimate bachelor’s lair, with a state-of-the-art entertainment center and a thousand-CD collection that includes all kinds of music that women find irresistibly cool.

  If I can get them back to my place, the chances are excellent that they’ll surrender to my charms. I’m a handsome, fit, powerfully built man who is thrilled to be the quintessential bachelor. But life has a way of taking unexpected turns.

  One dripping-hot Friday evening, I was waiting for a friend at a trendy club. The scenery was good, particularly a clutch of three girls at a table at one side of the room: a tall, buxom blonde; a cute brunette squeezed into a micro-mini; and the real gem, an Asian-Indian girl with long jet-black hair, sharp features, full lips and the darkest brown eyes. Her wisp of a halter top made her C-cup breasts look enormous against her slender frame, and her slacks were so tight that a little squinting revealed a tiny lace thong underneath. She was sensuous, exotic and stunning.

  As I considered strategies to make her acquaintance, a guy at the next table swiveled around and said something to her that provoked a burst of laughter. This wolf had bided his time and struck at the right moment. In moments they were locked in intimate conversation. Knowing my chance had passed, I had to admire the guy—handsome, dark-haired, about my height, athletically built and expensively dressed.

  He looked familiar, but I couldn’t place him. Shortly thereafter my friend showed up, and we proceeded with our evening, scoping the talent and enjoying each other’s company. About an hour later, the Asian flower got up to leave with her fortunate companion.

  As they passed us, a look of recognition spread across the guy’s face. “Professor?” he ventured. It was an ex-student of mine who had graduated four years before and gotten in on the ground floor of a spectacularly successful dot-com firm. At twenty-five, Chris seemed to be doing well indeed. He introduced me to Lily, the dark beauty. Everything about her oozed sexuality. Chris and I exchanged numbers as well as knowing glances as we said our farewells.

  A few evenings later Chris called, and we arranged to meet for dinner. After several bottles of wine, I inquired after Lily. He could hardly contain himself while graphically detailing their encounter. His description of her dark nipples, washboard stomach, clean-shaved box and outrageous blowjob technique gave me a raging hard-on. She was, he said, sensational and insatiable.

  Chris and I met now and again over the next few weeks, and he always had new stories about Lily or the other ladies he was banging. He often peered deep in my eyes or rested his hand on my lower back, but I didn’t think much about it until one September Saturday afternoon when we arranged to run together.

  Afterward, we headed for his building, where there is an exercise room and rooftop pool. When Chris peeled off his shirt, I couldn’t help but appreciate his body. His skin was smooth and tan. His muscles, while not bulky, rippled when he moved. I was surprised to find my groin tingling. At the pool he casually peeled off his tight gray shorts. I was speechless. His cock was superb, accented by a neatly trimmed bush and clear tan lines that indicated that he sunbathed in a thong. Again, I was surprised how sexually charged I felt.

  I stripped too, and we sunbathed and swam. He wasn’t the least bit shy about his nudity. In the pool he lost his balance, or pretended to, and fell against me. It was the first time another man’s member touched my body, and the sensation was electric. Thoughts of making it with him whirled in my head.

  Chris’s apartment was amazing, with modern furniture and a fabulous view. As I showered, he opened the shower door and handed me a vodka gimlet, grinning slyly while checking me out blatantly. As I put on the thin gauze shorts he had left out for me, I peeked in his bedside table and found a vibrator, lubricant, condoms and a bottle of amyl nitrate. He was prepared!

  Chris showered next, and came out wearing only a flattering pair of navy-blue silk bikini briefs. We loaded up his water pipe and proceeded to get stoned. The hot day, the vigorous workout, the refreshing swim, the great view and the excellent herb had me brimming with desire. Chris began to speak of his gymnastic sex with Lily the night before—right where I was sitting now.

  “The last time,” he said, “she begged for it up the ass. It was fantastic! She was whipping her head around and pounding her fists, yelling, ‘Fuck my ass! Yes! Fuck it!’ ” He stroked his bulging briefs openly. “Then,” he added, smiling mischievously, “she did my ass.”

  “She did what?” I said.

  “While going down on me, she lubed me up and used a vibrator. You’ve never had a chick do that?”

  I hadn’t, I said, though a few had given me a rimjob, and one inserted a finger.

  “Did you like it?” he said.

  “Yes,” I said, “but I guess I just never got used to it.”

  Chris stood, his cockhead peeking out of his bikini, and said, “You’ve never made it with a man, have you?”

  I shook my head.

  “Do you want me to go down on you?” he said.

  Overwhelmed, I could only stare at Chris. Then I nodded slowly. He started toward me but was interrupted by the door buzzer. “I’ve got a surprise for you,” he beamed. He answered the buzzer, “Come on up,” and pressed the button to let the caller in. He then motioned me off the couch, put his hand behind my head and kissed me, thrusting his tongue in my mouth. Our cocks rubbed together through the thin fabric of our shorts. Then there was a knock on the door, and he broke free to answer it.

  There was Lily, in a very brief halter-and-shorts set. Unhesitatingly, Chris pulled her to him and untied her minuscule top. Her hands went to his ass, then to his front, releasing his straining shaft. The two of them turned and smiled at me, standing dumbfounded. Without a word, Lily made her way over and kissed me passionately. Chris came up behind me, licking my neck and grinding his cock in my ass crack, then dropped to his knees, pulled down my shorts and fondled my balls.

  I couldn’t believe what was happening! Lily broke away only long enough to pull off her shorts, revealing a completely shaved pussy. She pushed me back on the couch and in one motion swallowed my cock. But after one swift, deep, wonderful suck, she pulled away from me as Chris came closer. He captured my gaze as he had before, then placed my hand on his dick. I was fascinated by its texture and heaviness. I knew I wanted it in my mouth.

  Lily watched as I pulled Chris to me—knowing, no doubt, that this was my first time. My heart was racing. Chris handed me the bottle of amyl nitrate. I took a deep snort, then parted my lips and slid his beautiful cock in my mouth. I was unspeakably high as I felt
him pulsating between my lips. Right then he was the only thing in the world for me. I took his firm ass in my hands and pulled him closer, taking him deeper. He fucked my mouth just as I had often done with women. It was an ecstatically erotic experience.

  Lily wanted to suck Chris too. We passed him back and forth playfully, alternating between his cock and balls. She ran her hand between his legs and inserted her index finger in his ass. This was too much for him. She offered me the chance to take his imminent orgasm. Having gone this far, I took his round cockhead as deep in my mouth as I could while Lily licked up and down the exposed portion of his shaft.

  His jism exploded in my throat, hard and copious. The force was so strong that I pulled away, and the next shot hit me in the chin. Lily devoured the rest of his creamy come. When she finished rubbing his dick over her face she licked me clean, and we exchanged his seed in a deep kiss.

  As Chris collapsed on the couch, Lily led me to the bedroom. Both of us were trembling with anticipation. Her body was exquisite. Her skin was dark and flawless. Lustrous hair framed her full breasts. Her tiny waist and heart-shaped ass were accented by tan lines that showed that she, like Chris, sunbathed in a thong.

  Her bald pussy felt like the gentle folds of a perfumed flower. I savored the jasmine taste for only a few moments before she pulled me up, licked her juices from my face and placed my cockhead at the entrance to her cunt. Wet as her pussy was, she was so petite that I had to ease in, allowing her to adjust until I could fill her up. We quickly fell into an intense rhythmic motion, twisting our bodies and arching our backs.

  Soon Lily’s breath began coming in quick gasps, and the sounds she made progressed from low moans to a piercing scream. Her head thrashed about as her body spasmed. “Fuck me! she yelled as her climax mounted, and I erupted with her.

  We lay content in a tangle of arms and legs. The sun had set, but the lights of the city illuminated the bedroom. I was happy when Chris joined us. He lay between us, and caressed our faces, then our chests, then between our legs. Our passions rapidly rose again. Chris now went down on Lily while stroking my rising member. Then he moved over and took me in his mouth. I watched, enchanted, as his lips moved up and down on me.

  After deep-throating me to the brink, he rolled me on my stomach and produced the vibrator and the lubricant that I had seen earlier. He used the vibrator on Lily first. She gasped with pleasure as he slipped it up her cunt, then fucked herself on it as he applied lubricant to my ass. When she climaxed, he removed the vibrator from her pussy and worked it in my ass. I was never so turned on in my life! “Yes,” I rasped over and over as the thing slid deeper in me.

  Chris bent down to me and whispered, “I want to fuck your ass.” He pulled the vibrator out, turned on his back and pulled me on top of him. I felt his rod between my cheeks, and I rocked back and forth, teasing both him and myself. Lily watched as if transfixed. I hesitated only a moment before reaching back and placing his thick rod at my entrance. I lowered my body eagerly, feeling him slide up inside me, joyfully taking every inch until I felt his pubic hair grazing my butt.

  Lily passed the amyl nitrate, and we each took a hit. My head spun as I ground my ass hard around Chris’s thrusting pole. My thighs flexed as I raised and lowered myself, rotating my hips at varying speeds and squeezing my sphincter. I think even Chris was surprised at the thorough fucking I was giving him.

  Lily was now working the vibrator furiously in her cunt. “You guys, that is so fucking sexy!” she cried. Then, while continuing to masturbate, she engulfed my hard-on in her mouth. “God, I’m coming!” Chris panted, jerking convulsively as he filled me with his juice. Seconds later, I exploded in Lily’s throat.

  When I awoke the next morning, Lily had left and Chris was on the balcony sunbathing. He smiled at me, then explained that, though he’s primarily attracted to women, he had been having sex with men as well for five years. He had been turned on by me, but suspected I wasn’t ready, so he and Lily hatched a plan to seduce me. Lily had never been with two guys before, and before leaving expressed a desire to do it again. Only this time she wanted to be fucked by both of us at the same time.

  I said I thought that could be arranged!—Name and address withheld

  HE ENJOYED HIS GIRLFRIEND’S ADVENTUROUSNESS AND HIS SCHOOL FRIEND’S ENDOWMENT

  Several years ago I had a girlfriend who was a cute blonde with small tits but the finest ass any man could ever hope for. Not only was Corinne nice to look at, but she was the most sexually adventurous woman I have ever met. During sex we often talked of having a third person join us.

  The night before Halloween we went out partying with two of my friends from college. The liquor flowed freely, and we were all feeling pretty good. After we left the party, I first dropped off Corinne, then my friend Will. Eric was staying at my house for the weekend. As we drove, I blurted out the question, would Eric like to fuck Corinne? He was understandably surprised but confessed that he had fantasized about fucking her ever since he stumbled on some pictures I had taken of her.

  The following night the four of us went out again. When we decided to head home, Eric and Corinne jumped in the backseat while Will rode shotgun. After we dropped Will off, the three of us went back to my parents’ place but stopped at the guest cabin, to finish off some beer. I think Corinne was suspicious, but she was unaware that both of our fantasies were about to come true.

  After a little more beer, I was eager to get things started, so I started kissing Corinne. As usual, once I had my tongue in her mouth she became hot as a volcano. I unbuttoned her shirt while Eric looked on. As I took a pert nipple in my mouth, I whispered that we were being rude to our guest. Sensing her approval, I looked over and invited Eric to join us. He wasted no time sliding next to me and sampling a nipple himself.

  The two of us sucked and kissed our way slowly down Corinne’s belly until we reached her jeans, where we continued to suck and kiss while we unbuttoned and removed them. Soon we were taking turns licking her tasty little cunt while she moaned in ecstasy.

  Eric and I stood to remove our clothes. In school I had often seen him naked, but never erect, although he had often bragged about the size of his cock. When he turned around, Corinne and I got a big surprise. (He told us later it was seven and a half inches long and two inches in diameter.) As he crawled on the bed, I asked Corinne if she thought it would fit. She said she would make it fit.

  Eric and I knelt at Corinne’s head and let her take turns sucking our cocks. I still remember the excitement I felt watching her try to wrap her mouth around Eric’s uncircumcised head. Finally I landed on top of her and thrust my cock in her pussy as she continued to suck away at Eric’s monster, just a few inches from my face. She sucked and slobbered on the head while jacking him off in her mouth.

  The action was so hot that I was approaching orgasm. Not wanting to come yet, I suggested we change positions, and there my beautiful girlfriend was lying on the bed with her legs spread and my friend above her preparing to shove his giant cock in. She grabbed it to assist in the penetration.

  They started by rubbing the head slowly up and down her slit, until it finally eased in. At that point she let out a giant moan. They continued slowly until she was able to take him all in. Then they went wild. Eric pulled out and slammed back in with tremendous force, and Corinne responded with moans of pleasure.

  When he stuck his tongue in her mouth, she began to thrash against him, still fucking that giant cock for all she was worth, grabbing his ass and pulling him in as deep as he could go. Now that she was warmed up, she pushed him off, and as he rolled over, his shiny cock towering above him, she got on top of him and slid it in all the way to his balls. I saw his cock stretch her completely open.

  At one point his cock slipped out, and I stuffed it back in. I licked my way down her crack till I reached her hole. As I licked it, his balls occasionally hit me in the chin. I lubricated her asshole, then positioned myself to enter her. The feeling of being in her ass whil
e my friend’s giant cock fucked her petite pussy was so indescribably arousing that I couldn’t hold off for more than a few moments before coming inside her.

  I slid out of Corinne’s ass, but she continued to fuck Eric for a few more minutes while I watched. Then she rolled off of him and onto her back. She spread her legs wide to allow him full penetration, and he sank his huge cock in again up to his balls. Again she grabbed his ass and pulled him in deeper. His balls tightened as he began filling her with his seed.

  They kissed as they came down from their high. Eric rolled off of Corinne, and for the first time I saw her pussy stretched out and full of another man’s come. She got up and set out for the kitchen, walking kind of bowlegged, with semen dripping down her legs.

  We got dressed and headed over to the main house. Eric went to the guest bedroom, Corinne and I to mine. I couldn’t wait to get in her tasty pussy. As soon as we were undressed, I tried to eat her, but she said no, she hadn’t cleaned up yet. I said it didn’t matter and dove between her legs. I loved the taste of her fresh-fucked pussy—their combined juices were a treat.

  When I finished eating her, I mounted her and slid my cock in effortlessly. Her stretched pussy seemed to suck me in. I told her how much I had enjoyed watching her make love to another man, and said she could do it anytime she wanted, as long as I could watch or at least get sloppy seconds. This was the beginning of an exciting series of adventures we had together.—N.M., Cleveland, Ohio

  HE LUSTED AFTER HIS WIFE’S HOT FRIEND FOR SEVEN YEARS. TONIGHT WOULD BE THE NIGHT

  Violet is a friend of my wife’s I’ve gotten to know well over the seven years of our marriage. My wife is aware that there has always been a kind of sexual tension between us, and it has been the subject of many jokes among the three of us.

  “You wouldn’t know what to do if Violet offered it to you,” Beth would say. To which I would reply that she was probably right but we would never know until it happened. Both Beth and Violet always swore that it never would. And nothing ever came of it until recently, when the two of them decided to put me to the test.