Letters to Penthouse XIV (10 page)

SOMETIMES OUR GREATEST PLEASURES ARE THE MOST UNEXPECTED

I’m a happily married man and have never thought of cheating on my wife, until a few months ago.

I was in New Orleans for a three-day conference. I arrived a night early so I could get the registration out of the way and attend an orientation. I decided to go out on my own for dinner and went to a very popular, informal but crowded restaurant. I was waiting for my meal and watching all the customers when a very attractive woman asked to share my table. We spent the meal talking about our lives, the city and what brought us to town. It turned out that Josephine was attending the same conference, she was single and she was from out of town, too.

As we were finishing up with dinner and getting ready to leave, she asked me if I’d mind walking her back to her hotel. It was a few blocks away and she didn’t feel comfortable walking back alone at night in this strange city. Having a small sense of chivalry, I agreed.

Up to that point, there had been no thoughts in my mind about anything developing between us. As we were walking back to her hotel, we came upon a doorway that opened into one of those beautiful old New Orleans courtyards. We stopped and peeked in and were caught off-guard by the sight of a young couple in the shadows making passionate love. They were fully clothed, but her dress was up over her hips and he was giving it to her doggie-style, and he was fucking her hard. They were so deeply into what they were doing, they didn’t notice that we had been watching them. Josephine and I just stood there and watched in silence. I jumped slightly when I felt her hand softly entwine with mine. It seemed so natural that I just grasped hers back in response. She turned around, looked me in the eye and said, “We’d better go.”

When we got to her hotel, she invited me in for a drink. There was a bar on her floor around the corner from her room. I felt a bit uncomfortable walking through a hotel with this pretty woman, but there was some kind of attraction between us that I couldn’t deny. As we were making our way towards the bar, we passed a room and heard moaning and groaning. She stopped me and laughed, “Twice in one night? This must be a sign!” before showing me into her room just down the hall. I hesitated for a second when we reached the door, but she massaged my crotch and pulled me in. No matter how much I kept thinking about my wife, I couldn’t resist.

My brain went completely blank when she fell to her knees, opened my fly and pulled out my cock. As I looked down, I was treated to the view of my cock completely disappearing and reappearing as Josephine deep-throated me. The events leading up to that moment as well as the thrill of the forbidden had me shooting into her mouth in no time. She moaned with pleasure as she swallowed my come. My wife rarely lets me come in her mouth, much less swallows it.

“Let me return the favor,” I said as I pulled off her skirt and panties and laid her down on the bed. As I bent to eat her, it suddenly dawned on me that she was the first woman other than my wife that I would taste. Her scent and flavor were decidedly different from my wife’s, and her aroma had me swooning. I was able to make her come much more quickly than I expected, and I had to hold on for dear life as she screamed her way through it.

After she calmed down, we decided to order some room service. I shared my fantasy of watching a couple make it, and I could tell she was intrigued by the idea of possibly screwing another complete stranger while I watched. When the delivery person showed up, it was a woman. Josephine cast her eyes down to the floor, blushing a bit, and said, “Sorry, I’m not ready for that.” The delivery woman looked at us strangely and left. Josephine suggested we take a shower together. I ended up fucking her standing up under the pulsing stream of water, another first for me.

After cleaning up and drying off, I was overcome with an enormous feeling of guilt, so I dressed and left, apologizing to Josephine. She said she understood and gave me her business card, telling me to call her if I ever got the urge again.

When I got home, I tried my best to put this incident behind me so I could get on with my life. My wife seemed to notice that my lovemaking was a little more energetic, but she never said anything about it. A week later, I went into work and my boss introduced me to my new associate: a beautiful woman named Josephine!—
C.M., Chicago, Illinois

A HORNY WIFE USES THEIR COUNTRY GETAWAY TO GET SOME ON THE SIDE

My thirty-eight-year-old wife Diane works as an auditor for an accounting firm and I have my own business consulting firm. We’re both fairly well-off, so last year we bought a small country place about two hours from our home in the city. It’s the very last house on a small road located by an old creek, without many other residences in sight (there’s an undeveloped hillside above our property). Because of the way it’s situated, we have roman shades on the windows but usually leave them fully open since no neighbors can directly see in and people rarely walk by. I often have to work on Saturday so Diane goes up almost every Friday for the weekend. I join her there on most Saturday nights, and our teenage children usually stay with relatives.

About five years ago, Diane started to exercise regularly, rising fairly early in the morning to work out at a local fitness center. As a result, she has toned her body into a very shapely 37-24-36 figure. She’s five foot four and usually keeps her weight around one-hundred eighteen pounds. She’s a natural auburn redhead with wide green eyes, a classic nose and a broad mouth with sensuous lips. She inevitably attracts attention when she walks into a room, but she has such grace that it’s usually striking but not overly sexual.

Her audit assignments usually result in her traveling overnight at least once a month for a few days. While we’ve had a full, active sex life throughout our sixteen years of marriage. I’ve thought that she’s probably had some affairs. When she drinks alcohol, she gets kind of flirtatious. At business parties, she always watches carefully not to drink too much, but on vacations, I’ve seen her get fairly friendly with some of the men whom we’ve met. To my knowledge nothing ever happened, but I could see the reaction she was getting.

Diane also cares about clothes and prefers outfits that are stylish and expensive. About six months ago, I noticed some changes in the way she was dressing. She always had some sensual lingerie, but now that seemed to be all she would put on. She was wearing low-cut bras and string bikinis or thong underwear. She stopped wearing pantyhose and started wearing garterbelts and stockings or just stand-up stockings. Her skirts and dresses were almost all above her knees or with fairly high slits. She was wearing tank tops and left her blouses open to show off her breasts more than before. At our place in the country, she would usually wear short shorts or tight jeans with halter tops in warm weather. She seemed to be going braless a good deal of the time, too. A few times when we were out in the country on a warm Sunday, I noticed that she would be wearing a skimpy sun dress and nothing else. Her nipples frequently got stiff from brushing up against the dress’s material. When we were in a local restaurant for lunch on one of those Sundays, I noticed several guys at a table near us looking our way. Diane smiled back. It even seemed at one point that she had crossed and uncrossed her legs so that they could see that she wasn’t wearing undies. Diane didn’t say anything about them.

A month ago, the kids and I were at our city home for the weekend. Diane had gone up to the country place on Friday morning. Diane said that she had to meet with a client whose office was in a town on the way to our country home. I planned to go up on Saturday afternoon. The kids had stuff to do in the city, and Diane’s parents, who live down the street from us, were going to look after them. But on Friday afternoon, the appointment I had for that Saturday canceled out. I arranged with my parents to keep track of the kids on Friday night and decided I’d leave after rush hour and surprise Diane.

I approached our country home at about nine o’clock that night. To my surprise, I saw a number of other cars parked out in front. Instead of going up the driveway, I left my car about a hundred yards down the road. I had some binoculars in the trunk and went to the hillside overlooking our home. I got a clear view of the living-room window, a bedroom window and our hot tub.

When I looked through my binoculars, I saw Diane and the three guys whom I had noticed at the restaurant a few months before. Diane was dressed more provocatively than I’d ever seen. She had on a very short, tight black skirt that barely covered her ass, a pair of fishnet stockings, high-heel sandals and a sheer black blouse covering up a lacy black bra. The guys were wearing jeans and T-shirts and looked quite well-built. It seemed as if there might be music playing because Diane was swaying back and forth as she served hors d’oeuvres and drinks.

One of the guys got up and put his arms around her, grabbing her ass as they began to dance. He pressed tightly up against her as she gave him a deep kiss. I was shocked. I watched as Diane proceeded to dance with each of the guys. They didn’t hesitate to squeeze her ass or touch her breasts. The dancing stopped for a moment until Diane started to strip for the guys. She undressed for them slowly, and she went up to each one to let him feel her breasts and rub her cunt. I noticed that she had trimmed her bush to a small, neat triangle. She then encouraged them to undress. They all had huge erections. She bent down and licked each prick but did nothing more. Instead, she led them to our hot tub. Once they were outside I could hear them as well as see them.

One guy was mentioning how much they missed Diane during the week. She said, “I don’t think your wives feel the same way.”

Another said, “But they don’t know.”

Diane looked over and said, “I’m not so sure about that …”

There was a lot of groping going on in that hot tub. Diane has sensitive breasts and really gets off when they are rubbed just the right way, and it looked to me as if that’s what happened. They were in the tub for about fifteen minutes. After they toweled off, they wasted no time in moving to the bedroom.

From my perch I could see everything they were doing. I noticed that one of the guys had a video-camera. Diane started out giving one guy a blowjob while another guy ate her out. The third guy started filming them. They soon switched and let the video guy get a blowjob while the first guy started giving Diane head and the third guy took over handling the video. No one seemed to have gotten off yet.

Diane then motioned that she was ready to get fucked. The guy who was getting the blowjob got on top and began to move his prick slowly in and out of her. The guy with the video-camera kept filming, while the other guys sat off to the side watching with huge erections. After the first guy came, the one not filming immediately took his place. Diane seemed to be continually twitching and having orgasms. After about five minutes, he was replaced by the guy who had been working the video-camera. He lasted about ten minutes while the one not fucking her and not videotaping managed to get in the action with her licking his prick while he used his hand to increase her pleasure. It all ended with Diane apparently having a huge orgasm. The guys left at about eleven o’clock. I had been watching for nearly an hour and a half. I didn’t know what to do or say.

After they were gone, Diane took a shower. She also changed the linens on the bed and put them in the washing machine. I then noticed that she turned on the television and inserted a videotape. It was the one they had just made. As she watched, she got out a huge black dildo and began to play with herself. When she was good and wet, she inserted the dildo and had another orgasm. She then stopped the video and turned off the lights.

I decided that I should stay somewhere else that night and found myself a motel room on the other side of town. When I returned in the morning, Diane expressed surprise at me getting there so early, but she also seemed delighted to see me. I said that I just missed her too much and cancelled my Saturday meeting. I then took her in my arms and started to kiss her and feel her up, rubbing my hands where the hands of other men had been the night before.

Diane said, “My, you are horny, aren’t you? But then, so am I.” We proceeded to have one of the best fuck sessions ever. Diane was unbelievable. She did things to me with her mouth that I just couldn’t believe. She used her cunt muscles to give me pleasure like she had never done before. I asked her to tell me a dirty story, and she started to tell me about what she did with the three men the night before, but as a story she was making up, not as something that really happened. I asked her if that was what she wanted. She looked up and said, “Maybe. If you wouldn’t be jealous. Because no matter what my sexual fantasies are, you’re the only man that I love.”—
D.R., Boston, Massachusetts

SHE ASSUMES THE RIGHT TO FUCK OTHER MEN, AND HE SECRETLY APPROVES

When my wife Mandy turned forty, she announced that she intended to date and party with other men. Although I’m a sweet guy, a good father and generally supportive of what she does and wants to do, it turned out that I was deficient in one area. I wasn’t satisfying her sexually. Before she got too old, she said, she wanted to see what it would be like to start fucking other men. Our daughter was off at college so she had much more free time than before. She didn’t want to cheat behind my back and hoped that I would understand and stay with her.

Mandy is still a very striking woman. She is five-foot-eight-inches tall and weighs one hundred twenty pounds. She dyes her shoulder-length hair blonde. Recently she had plastic surgery to tighten her breasts—her measurements are now 36C-28-35.

The reality of the situation is that I’ve always fantasized about her sleeping around. In fact, I’m fairly certain that she had had some affairs before. Her libido has always been very strong. While we would fuck several times a week, Mandy would usually come every night, either by masturbating or by me fingering her or going down on her. But now it seemed like she was going to be more blatant than before.