Letters to Penthouse XIX Read online

  When we got to the room Mike opened the door. Wendy, Caroline, and Dana followed him inside. I stood frozen, having second thoughts when Dana turned and noticed I wasn’t following them. She smiled a devious smile, took my arm and said, “Come on, you’re not backing out on us now, Evan.” She tugged my arm, and I moved through the door, my heart racing.

  Mike had just finished pouring drinks for everyone when Dana and I came into the room. Wendy was standing next to Mike, and Caroline was already comfortable on the bed. Dana walked over and sat down next to her. I made my way to the couch and sat down, trying to not look nervous.

  There was an awkward silence for a moment, then Caroline said, “You guys said you were ready for anything, right?” Mike and Wendy looked at each other. Wendy leaned up and kissed him. She squeezed his crotch. As she took her hand away the outline of his stiffening dick was visible.

  Wendy smiled at the girls and cooed, “Yes, definitely.”

  Dana looked over at me like she was wondering if I was ready to get into it. I nodded, trying to look the part, and said, “Sure.”

  Dana kept her eyes on me, smiling, and said, “We want to see Evan walk over, get on his knees and give Mike a blowjob.” For the second time that night I felt the blood drain from my face, except this time I felt almost faint. It had never occurred to me they would ask for something like that.

  I sat there frozen and heard Wendy say, “Mmmm, I like that idea.” Mike didn’t say anything and I realized that everyone was looking at me. Dana said, “You did say you were up for anything, Evan.” She paused for a second, her smile daring me, and added sternly, “Do it. I want to see you do it.”

  The room fell silent. Still lightheaded, I made my decision. I stood up and walked slowly over to Mike and Wendy. Wendy rubbed Mike’s cock through his pants as I got down on my knees in front of him. She pulled his prick out, pumping it slowly in front of my face. She pointed it at my lips. Someone somewhere in the room said, “Take it.”

  Slowly, I raised my hand, replacing hers on his shaft. His skin was hot and his dick, much larger than my own, twitched in my hand. Pre-come oozed from the tip. I stroked him, forcing more liquid out. My heart was racing and I have to admit I was incredibly horny.

  I opened my mouth and licked the tip before covering the head of his cock with my lips. The tip was fleshy and soft, and I could taste his ejaculate. I sucked him further into my mouth and heard him groan. As I sucked him I stroked his shaft with my hand and swirled my tongue around the head. Then Wendy grabbed his shaft and fed his dick further into my mouth. She said, “That’s it. Take it all the way down and then suck just the head with your lips. He loves that, don’t you, Mike?”

  Mike was groaning loudly and began thrusting his hips into my face. As his prick grew harder in my mouth it occurred to me that he was going to come soon. I didn’t know what I’d do, but I was beyond caring. My own dick ached in anticipation.

  Suddenly I realized Dana and Caroline were next to me, watching. Dana leaned down and whispered, “I want to see you finish him off.” I stroked him harder and thought he would spurt any second when she added, “But not right now. Right now, I need to be fucked.” With that she reached over and took Mike’s dick from my mouth, playfully kissing the swollen cockhead. She then led Wendy and Mike over to the bed, where they began to undress.

  I looked at Caroline. She smiled and pulled me to the couch. We were both naked a moment later. She whispered, “I think you liked that.” Then she slid down and swallowed my cock. The feeling of finally having her mouth around my prick took my breath away.

  I had a clear view of the bed. Mike mounted Dana while Wendy sucked her tits. Dana slipped a finger into Wendy’s cunt and Wendy moaned. I was ready to lose control and told Caroline to back off or she’d make me come. She looked up, grinning, and said, “Not yet, baby. You don’t come until I’m ready for you to come.” She turned around to face Dana and the others, then slid herself onto my dick. She leaned forward, riding me hard. It was as though she was searching for just the right spot in her cunt, and when she found it she began grinding herself onto my pole. “Mmmm yes, that’s it. Fuck, yes,” she groaned. She impaled herself on my dick again and again, bringing me that much closer to orgasm. I glimpsed over to see that Dana was on top of Wendy in a 69 with Mike kneeling behind Dana, pumping into her pussy.

  Watching the three of them finally became too much for me and I started to come. I thrust my prick even further into Caroline, hitting that spot deep inside her until she started coming, too. My balls emptied into Caroline’s pussy, sending sperm racing toward her womb. She fingered her clit as she rammed herself onto my dick, moaning loudly as she climaxed.

  Mike concentrated on fucking Dana, pumping her with an abandon I’d seldom seen before. Dana brought her head up from licking Wendy’s pussy and cried out, “Oh yeah, suck my clit, Wendy, suck it. I’m coming, I’m coming!” At that Mike let out a loud moan and shot his load deep into Dana’s twat. When Dana started coming down from her orgasm she lowered her face back to Wendy’s pussy and gave her a climax as well.

  We all collapsed, exhausted and fucked out. After a few moments Caroline and Dana looked at each other and began laughing. “Wow!” Dana exclaimed as they giggled. “That was really wild!” Then Dana caught my eye. “But then again we’re not done yet, are we, Evan?”

  I flushed once again, knowing exactly what she meant. “I love the way he blushes,” Caroline laughed.

  “Come over to the bed, Evan,” Dana cooed. “There’s something that I want you to finish.” There was a twinkle in her eye. I went over to her ready to do what she wanted, with Caroline following me close behind.

  Dana had Mike sit down on the edge of the bed and lean back. Caroline told me to get on my knees in front of him. Dana was kneeling next to me on my left, Wendy was to my right and Caroline was looking over my shoulder. I stared at Mike’s semi-hard dick. My heart raced again and I felt my dick twinge. Dana grabbed my rod then whispered, “Do a good job and you’ll get a reward.”

  My dick got immediately hard in her hand. Wendy took Mike’s cock and, as before, brought it toward my lips. His cock was slick with Dana’s juices and his own come. Caroline pushed me forward gently and I took the head in, swabbing the tip with my tongue. I had to admit to myself that his cock tasted great as I felt him grow harder in my mouth. I sucked deeper until my lips touched Wendy’s hand at the base of his shaft.

  Mike moaned and thrust his hips upward. I pulled back to the head, licking and sucking it. Wendy moved her hand away and I grabbed hold of his shaft, stuffing him back into my mouth. Dana began slowly stroking my dick and Caroline said, “Yes, that’s it, suck him. We want to see you make him come.” Mike thrust his dick further into my mouth as I continued.

  I could only get about half his cock into my mouth, so I began jacking him off and concentrated on sucking the first few inches. I slid my tongue back and forth against the slit of his cock. He was rock-hard by then, and his dick was throbbing. He groaned and grabbed his dick with one hand and the back of my head with the other. The girls watched transfixed as he pumped his cock into my face. Dana wiped the back of her hand across her mouth and said, “He’s going to come. Are you ready, baby?” I was. I couldn’t wait.

  My hands on his thighs, thumbs kneading the tight muscles there, I held still while he jacked himself off with my mouth. Suddenly he grunted loudly and his hot come hit my tongue. I pressed my lips tightly around the head, sucking him forcefully as he squirted down my throat. His dick slipped out of my mouth and he sprayed come on my lips and down my neck.

  Dana moaned and stroked my cock faster. I felt a set of lips wrap themselves around my cock and looked down to see that Caroline had started sucking me. As Dana jacked me off she kissed me deeply, Mike’s come mingling on our tongues. As Dana stroked and Caroline sucked me I came harder than I ever had in my life. When my orgasm was over I fell back on the bed, numb and exhausted.

  I may have been spent, but the g
irls were still raring to go. For the next hour Wendy and Caroline teamed up on Dana, making her come again before turning their attention to each other. Finally, we all collapsed into one big, sweaty heap.

  I woke up after four and slipped out of bed. I leaned down and kissed Dana, who stirred out of her sleep and smiled at me. I whispered, “That was incredible.”

  She replied, “I didn’t think you would actually go through with it all. I’m sure glad you did.”

  I thought for a moment and said, “That was wilder than anything I ever dreamed of.” We gathered our things and dressed quietly in the dark. When we were dressed and had all our things together she kissed me and said, “You know Evan, I see something in you that really gets me going.”

  As we left I wondered how this would end. Would Dana and I pursue a relationship? If so, I know I’m in for one helluva ride!—E.W., New Orleans, Louisiana

  A SAD OCCASION BECOMES ANYTHING BUT WHEN OLD FRIENDS GET REACQUAINTED

  My wife Dawn recently drove us down to D.C. for the funeral service of an old college pal of hers who’d recently died from breast cancer. From where she stood behind the grieving family members, Dawn spotted two old friends from our old swinging days. When she pointed them out to me I recognized them instantly as Wayne and Kathleen. They were much older than Dawn and me but still looked fit and attractive. Wayne had grown a beard that was almost white. Kathleen was dressed for mourning with a long-sleeved, black silk dress. Even with Wayne holding an umbrella over them, Kathleen’s wet dress clung to her natural 38C breasts. Her rain-spattered nipples were erect and poking out about an inch.

  The girls were eyeballing each other, trying to figure out where they knew each other from. When the service was over, we made our way over to them. Kathleen and Dawn held each other and cried. Slowly the girls began to kiss and we decided to meet Wayne and Kathleen back at their hotel before things became too uncomfortable for everyone.

  After we got into the room, Wayne called room service and ordered up some wine. Besides the girls’ kissing, I could tell that the old spark was still there because he remembered Dawn’s favorite, and she thanked his consideration with a lingering kiss.

  Kathleen began to undress in front of us. Dawn blushed from the excitement. The crimson hue rose from her chest up into her neck, face and ears. Then Wayne stripped down to his boxers and his uncut boner stuck out like a flag pole from its cotton sheath. A shit-eating grin crossed his handsome face when he noticed Dawn gazing at his hard cock like she did in the old days.

  There was a soft rap on the door. Kathleen nodded to me to answer it, making zero attempt to cover herself, standing near-naked except for her lacy black push-up bra and high-rise panties. I recalled that she and Wayne played tennis year round and her legs still showed the firm muscular tone the sport can give.

  Opening the door, we saw that Carlos, a hotel staffer whom I put at about twenty, brought the two bottles of wine in on a cart along with some glasses. One gaze at the scene before him and I noticed a tent begin to form in his pleated uniform trousers. He had an island accent that I recognized from my tour in Vietnam. It was always Dawn’s fantasy to have sex with a black guy, but no serious effort was ever made to that end until that night.

  Kathleen moved with the silent grace of a panther as she grabbed his hard-on through his pants. He liked her advances but a weird smile twisted his face. “Oh Miss, that feels so nice, but I can lose my job if anyone finds out.” As he looked my way I locked the door.

  Dawn unsnapped Carlos’ uniform pants. I hoped that Carlos could last long as Kathleen pulled the guy’s pole down from against his flat abs. She swallowed his monster cock down, feeling the weight of his smooth-shaved balls in her cupped hand. Kathleen has the most expressive eyes and just one look at Wayne brought him over. She took her lips off Carlos and fed the black cock to her husband as if it were a dinner she’d prepared.

  Dawn moaned as Wayne began giving the boy a blowjob. Kathleen came to my side as Dawn pulled my pants down and fed Kathleen my dick. After a few delightful minutes I had to stop Kathleen from sucking so I wouldn’t shoot off too soon. All the while the girls made each other’s clothes disappear item by item. Carlos and Wayne watched in awe.

  Wayne very calmly produced a rubber from his shaving kit. He unwrapped the condom, grabbed Carlos by the dick and rolled it down his cock. “You first,” Dawn said. Kathleen kissed her deeply before kneeling at the edge of the bed, ass pointed right up for easy access. Wayne and I helped position Carlos at the foot of the bed.

  To everyone’s surprise, Carlos preferred performing oral sex before mounting a woman, so he knelt down and tongue-fucked Kathleen’s ass and cunt till she was out of her mind with desire. Wayne quietly produced a camera and began snapping shots as Carlos slowly entered his bride of almost forty years. “Ah yes, give it to me, Carlos. Feed me that black meat!” Her cries were practically incoherent as he slipped it into her moist pussy.

  Dawn was completely horny by then and took her place on the bed beside the new lovers. Wayne put a condom on and devoured my wife’s cunt and ass until she begged him to fuck her. The scent of sex was heady as they fucked. I shot at least a full roll of this doggie-style orgy. A few minutes later Carlos removed himself from Kathleen’s cunt and Wayne from Dawn’s even though neither man had come. Dawn squealed with delight as Carlos stood there while he and Wayne removed their used condoms and replaced them with new ones. I was impressed with their staying power and with their obsessive hygiene.

  Wayne opened a fresh condom and put it on me. A confused look crossed Dawn’s face as another man handled my dick, but Kathleen never left her kneeling position as I set out to refresh her well-worn womanhood with my mouth. Still sensitive from Carlos’ cock, she moaned as I licked her ass and cunt in one stroke.

  After entering Kathleen’s cunt I noticed she was still tight as hell even after the pounding she received from the young black stud’s dick. I reached up and under Kathleen’s body to fondle her beautiful tits. They were swaying from each thrust I fucked her with.

  Kneeling next to us, Dawn couldn’t hold out any longer. I could see her toes curl as she sped into a strong orgasm, kicking her feet up and down on either side of Carlos’ lean torso. Carlos came with her, not bothering to slow down his pace as he spent his load into the prophylactic. I decided that I was ready. I felt Kathleen’s quim convulse as she came with me. I lay next to her happily fulfilled.

  What started out as a sad reunion turned into an erotic adventure we won’t soon forget.—T.W., Los Angeles, California

  THEY TRIED TO HELP A SPECIAL FRIEND SORT OUT HER EROTIC INCLINATIONS

  Growing up, I had a special relationship with my neighbor Donna, who lived next door and was about the same age as me. (She’s maybe a year older.) It’s not that I didn’t find her attractive—frankly, she’s a knockout. It’s just that somehow that never figured into our relationship. Maybe it was because neither of us had any brothers or sisters. For whatever reason, she always felt like a sister to me, or really a best friend.

  Even when she went off to college, she was sure to call me at least once a week, more often than not to complain about the men she met. In fact, it was through Donna that I met my future wife. She and Janice started out as college roommates and over time became the best of friends. It was in their senior year that Jan complained once too often that the men she met were all after one thing. Donna brought her home to meet her best friend, me.

  Now I don’t consider myself a studmuffin. I don’t have the rolling abs you seem to see all over the magazines these days. But the ladies seem to like what they see—six feet two, two hundred pounds of muscle, not from working out, but from working. I’ve worked for the city roads department ever since I graduated from high school. It’s hard, demanding physical labor, and I know a lot of people look down their noses at it. But it’s honest, satisfying work, and the obvious fringe benefit is that it keeps me in permanently good shape.

  Janice is a petite wo
man, with long legs and long raven-black hair, and a body that could induce a second look from even the most devout priest. Her large, round breasts certainly don’t detract from the picture. All in all, it was no wonder that she was having problems with men in school—they must have been all over her. Anyway, she and I hit it off right away, and within eighteen months we were married. The sex was incredible; our adventures are probably worthy of a letter of their own.

  Four years after we married, we had settled down as your standard suburban family, with a house, two cars, three kids, a dog and a cat. Through all those years, once a week like clockwork Donna would call to keep us up-to-date on what was going on with her. We were the closest thing she had to family now—her parents had passed before she graduated from college. So anytime anything went wrong in her life, she called us, and we tried to make sure we were always there for her. We helped her through countless boyfriend breakups and one failed marriage. In addition, she visited as often as her work schedule allowed, always bearing presents for the kids.

  Overall, life was good. I just had no way of imagining how much better it was going to get.

  It was early this past summer that Donna popped up out of the blue, knocking on our door, even though she has a key. Janice was the only one home at the time. She was surprised but happy to see her best friend of so many years. Soon after, Jan called me at work and said to come home right away. I hurried home expecting the worst, and was surprised to find Donna in the kitchen making coffee.

  “Donna has a problem,” Janice said, a little embarrassed, pulling me aside. “She needs our help.”

  “What do you mean?” I said.

  “She thinks she’s a lesbian,” Jan whispered.

  “What?” I said. I couldn’t help it.

  But as soon as Jan said it, I knew it was true. All the signs were there. I just never acknowledged them. She wasn’t the bull-dyke stereotype, with the muscular body and short hair. No, Donna was and still is a dynamite-looking woman who could have her choice of any man she wanted.