Letters to Penthouse XIV (45 page)

Chelsea told one of the guys to go get her purse. She took out a tube of lubricant, slathering some of it all over my joint for a few minutes. Then, with Sam still plowing the back forty and her left hand fisting my cock, she reached behind me with her right hand and started rimming my ass with her well-lubed fingers.

“Try this, Harry,” she whispered hoarsely as she slid one finger into my bottom while still pumping my penis. She must have touched my prostate because after a few minutes of her talented fingerwork my dick was finally standing up, almost fully erect for the first time that night.

“See, Harry, you can do it,” she said softly, sliding a second finger between my cheeks. The way Chelsea’s fingertips delicately tickled their way around my asshole felt very sexy. I pumped my hips to keep my dick moving between the fingers of one hand while she squeezed my buttocks with the other and ran her fingers an inch or two into my sphincter.

Between being carried away with what Chelsea was doing and being kind of drunk, I didn’t even notice everything else that was happening around me. But when I watched the videotape later on, I saw that my friends Benny and Cary had been standing off to the side, slathering some of Chelsea’s lube all over each other’s cocks. I guess they were getting tired of waiting for their turns to come up and their dicks were just about ready to explode. They started off by stroking themselves, but soon they switched and were doing each other!

I saw something else on the tape that I didn’t notice at the time. At one point Chelsea motioned to Cary that he should get behind me and then communicated to him with some quiet gestures that he should take over fingering my bunghole. Still kneeling in front of me, she put both hands on my ass cheeks and pulled me towards her mouth as Cary, grinning conspiratorially at Benny, slid two of his fingers gently into my sphincter. At the time I had no idea that one of my friends had taken over from Chelsea, and I continued to enjoy the stimulation of my anus, which finally had me hard enough to enjoy Chelsea’s blowjob. You can see Cary and Chelsea exchange glances as she pulled more firmly on my buttocks, opening me wide as Cary withdrew his fingers and quickly slid his long, thin cock into my dilated asshole.

Believe it or not, at that point I really had no idea of what was going on. I swayed on my feet and closed my eyes as what had felt good in my ass began to feel even better. But I still thought that Chelsea was the one who was fingering me. Her face was buried in my crotch, her hands stroking my ass cheeks, and Cary was sliding a boner and a half gently up my rectum. On the third or fourth stroke he brought his arms up and wrapped them tightly around my waist. That’s when my eyes finally popped open and I knew exactly what it was that I was feeling.

Sam had never stopped screwing Chelsea while watching me lose my anal cherry to Cary, and by then he dumped his come into her gash. He reached up to pinch my nipples lightly as Cary went on pumping me from behind. Then Zach began to stroke my pecker as Chelsea released it from her mouth.

I was a little bewildered at this turn of events, but at the same time I was more sexually excited than I could remember. A few seconds later my cock exploded its pent-up come all over Chelsea’s shoulders.

Cary had a tremendous orgasm just a few seconds after that and gave my bowels a tremendous squirt of sperm. Benny finally got to screw Chelsea, too. After he filled her twat, she squatted over my face, and I ate her out eagerly, again savoring the taste of my buddies’ salty sperm. We all laughed when Chelsea said that I was the first bridegroom she’d ever known who drank more sperm at his bachelor party than she did.—
Name and address withheld

THEY SET OUT TO FULFILL THEIR SWINGING FANTASIES, AND THAT’S JUST WHAT THEY DID

Soon after my boyfriend Gerald and I started dating we realized that we both had fantasies about having sex with strangers. We talked about going to a swingers’ club and finally found a place that looked like what we had in mind. It was out of town, so we took a weekend vacation and set out to fulfill our fantasies.

We were both a little apprehensive about doing anything at first. We looked around, then had a couple of drinks. That loosened us up to the point where we finally had the nerve to go into one of the theme rooms, where you could watch the scene through a small window. The first we came to was the bisexual room. There were two women in there—a blonde and a redhead—lying on a large round bed. The blonde was licking the other’s red pussy, and they were both enjoying the hell out of it.

I was beginning to get excited myself and decided that I wanted to participate, but I was too scared to walk into the room. When the blonde strapped on a dildo and started fucking the girl she’d been licking, I glanced to the side and saw that Gerald had gotten a bulge in his pants as he watched them.

The redhead looked over at the window and saw us watching. She smiled at me and motioned for me to come join them. What the hell, I thought, and before Gerald could say anything I stood up, made my way into the room and stripped my clothes off. Not surprisingly, Gerald was right behind me, and we found that there were two men in there as well, sitting and watching everything that was going on. On a table off to the side of the bed were some oils, dildos and other equipment we could play with.

I was welcomed by the blonde, who without any preliminaries took me in her arms and kissed me. A little nervously, I looked over at Gerald, who just smiled and nodded his encouragement. He soon came into the room and kissed me, reassuring me that whatever I wanted to do that night was okay. He then went and sat down in the corner, leaving me to get busy with the two beautiful women. The blonde laid me down on the bed and started to kiss my nipples, and the redhead quickly joined her. She then moved down to my already wet and anxious pussy and started licking and sucking. I came almost immediately, having one orgasm after another as much from the excitement of being watched by a crowd as from what my new-found partners were doing to me physically.

The blonde decided to test out my pussy-eating skills, so she spread her legs and squatted over my face. That’s when I learned how to lick pussy.

Out of the corner of my eye I saw one of the men walk over to Gerald, kneel down in front of him and start sucking his cock. Gerald not only allowed this, but he was soon tangling his fingers in the strange man’s hair, eagerly fucking his mouth while he watched the three of us women eating and sucking each other. Then the other man in the room approached him and held out his dick for Gerald to suck, which he did willingly. I watched as my lover shoved his cock deep into the first man’s mouth and dumped his come down his throat. The second man pulled out of Gerald’s mouth and shot a load of jism all over his chest.

The blonde girl leaped off the bed and started licking the come off Gerald’s chest, sharing it with the second man, who turned out to be her husband. Gerald walked over and kissed me deeply. I could taste the dick he’d been sucking, and he could taste the blonde’s pussy on my tongue. We gave each other a reassuring and loving smile at the turn our love-making had taken.

After having a couple more drinks, we found an empty room and started kissing and groping each other. In a few minutes a couple walked in and asked if they could watch. The idea of strangers watching
us
fuck made me so hot! It must have excited Gerald too, because we really went at each other. He was already fucking my ass when the man walked up to us and pulled out his cock for me to suck. I turned around to look at Gerald, and he was smiling. “Go ahead, suck him,” he said.

Like a good little whore, I took the stranger’s cock in my mouth and started to blow him. This turned Gerald on so much that he quickly came up my ass. The man asked Gerald if he could taste his come in my ass. Gerald smiled and said, “By all means, go ahead.”

As the man moved behind me, Gerald went over to the woman, who was busily fingerfucking herself. My lover helped her out by kissing her breasts and fingering her pussy along with her. I watched them, more turned on than ever. Meanwhile the strange man knelt behind me and started eating my cunt and my asshole, pushing his tongue deep inside each of them in turn, sucking the sperm out of me as I came over and over and over.

The man then asked Gerald if he could fuck me, but Gerald was so busy eating the woman’s cunt that I didn’t know whether he heard the question or not. “Yes, go ahead and do it!” I said to the stranger: “Do it! Fuck me good and hard!” He then thrust his cock inside me and plowed me hard and fast, bringing me to orgasm several more times as he commented on how good it felt to be fucking it.

Gerald was soon fucking the stranger’s wife. She yelled as she came, and then told him she needed a break. But Gerald was just getting started. He came over and asked me to get on top of the stranger. When I did, he got behind me and worked his prick into my ass. They were both fucking me so good! I could feel their cocks going in and out of me, and it drove me wild.

At that point another couple came in and decided to join us. The woman went over and started licking the stranger’s wife’s pussy, while the man stood in front of me and gave me his cock to suck. I had three cocks in me at once, filling all my holes, and it was the hottest and most erotic thing I had ever experienced. The three of them came almost at the same time, and I found myself with a smile on my face and my pussy, ass and mouth full of come.

We spent the rest of the weekend doing even more. We’re really looking forward to our next trip.—
V.S., Lansing, Michigan

HE SETS UP A BASKETBALL GAME WITH A SPECIAL TROPHY FOR THE WINNER: HIS WIFE

My wife Stephanie is a beautiful, petite thirty-year-old brunette, and we’ve been married for ten years. About five years ago we started talking about Stephanie’s fantasy of being gang-banged by a group of young studs. I always enjoyed the effect these discussions had on her, so I agreed that for our tenth wedding anniversary, which would also be the weekend of her thirtieth birthday, I would arrange for her fantasy to come true.

I work part-time at the gym on a military base, where every Friday night there was a pickup basketball game between five black Marines and five white sailors. I began to put my plan into action by asking the ten studs to schedule their game for after closing time one Friday and telling them that I’d provide a very special and interesting trophy for the winners. They must have had some idea of what I had in mind, because they agreed willingly.

I then told Stephanie to show up that night in her sexy tennis outfit: a short skirt with white-cotton panties and a cotton shirt that, when worn with no bra, shows off her large nipples.

When Friday night came, I closed the weight room early and set up a video-camera. Stephanie and I had agreed that this was to be a one-time event, and we wanted to be able to enjoy it over and over again.

The guys were just warming up in the gym when Stephanie walked in. She looked a little nervous but fantastically sexy. I wasn’t sure how she would feel when she saw the ten guys who would soon be filling her with come. She had never slept with a black man, but just by watching the Marines taking their practice shots, I could tell that was about to change real soon.

The guys were thrilled to find out that the trophy I’d promised them was my wife. I explained that the contest was to be a simple game of twenty-one points, with the winners getting to fuck her pussy while the losers (if you could call them that) would have to settle for blowjobs. For an added twist, the winners and losers would pair off, each pair taking her in her mouth and pussy at the same time. The guy in each pair who could refrain from coming the longest could fuck her ass as a bonus.

I could see that Stephanie was going crazy watching ten sweating studs with erections trying to win her favors as a sex trophy. Finally the Marines won the right to her pussy by a score of twenty-one to fifteen.

I moved behind her and whispered, “Enjoy,” as I pulled her shirt over her head, exposing her breasts. She smiled at the gasps and moans that came as they looked at her. I took her hand and led her into the weight room, the others following to claim their prize.

I had the five black Marines line up on one side of a weight bench, with the five white sailors on the other side. Then I bent my wife over it, crouching on all fours by the side of the bench for support. I gently kissed her as she looked into my eyes and told me she loved me. I then prepared her to be gang-fucked by ten horny studs.

I lifted her skirt and pulled down her panties, exposing her wet, shaved pussy and the first Marine and the first sailor in line pulled down their shorts. Stephanie moaned in anticipation as she got a look at two of the cocks that were about to invade her body.

I watched with mixed emotions as the Marine positioned the purple head of his tool at my wife’s pussy and slowly pushed it in. A low moan escaped her lips, but her open mouth was quickly filled with the sailor’s erection. With encouragement from their teammates, they began to fuck her really hard. Her body moved in rhythm with the Marine’s thrusts, but from the way her lips and tongue were working on the cock in her mouth, I knew she’d be having mostly black cock up her ass, because her oral talents would make short work of the sailors.

Sure enough, within five minutes she was drinking her first load of come. The still-hard Marine pulled out of her pussy reluctantly, although he was willing to wait for the tight little ass that he had been looking at while he was fucking her.

The second pair moved into place and started to work her over. I stroked her hair and played with her nipples as I watched her dream come true. She soon began to shake with her first orgasm of the evening. Once again the sailor in her mouth was the first to come.

Stephanie continued to experience a strong orgasm with each new set of cocks. The third Marine’s cock was larger than anything she had ever taken. As she cried out in ecstasy under his hard, steady strokes, she kept letting the cock in her mouth fall out. The Marine finally shot into her pussy and the sailors cheered, happy to know that at least one of them would have her ass.