A few years ago I wrote Penthouse Letters about a sexual adventure I had ten days before my wedding. An old boyfriend came to town and we wound up having sex. It was in retaliation for my fiancé getting a blowjob at his bachelor party, but I had unfinished business with this man. We reached closure on the sweaty sheets of his hotel room.
When I wrote the letter, I told my old boyfriend about it and I’m sure he’s jerked off to it all the time. I know my husband read it. I never confessed it was me, but I’m sure he suspected.
I’m in my early 30s, with a hot body I work hard to tone. (My 34DD boobs are all natural.) I do some modeling, including infomercials that I bet you’ve seen. Doug, my husband, is 15 years older than me—a great-looking guy and great lover who keeps me satisfied. But I often think about my fling.
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My wife Stella and I have been married for 27 years, and we are still completely in love with each other. Stella is half Asian and half Mexican, with long black hair and black eyes. She is five feet nine, weighs around 130 pounds and has a great set of tits on her 38C-28-38 body. We have always had a great sex life, as Stella is always horny and loves to fuck and suck cock.
We have both been avid readers of Penthouse Letters for over 20 years. We take turns reading the letters out loud to each other, and we always find them arousing. Over the years I have noticed that the letters that seem to turn Stella on the most are the ones about gang bangs and group sex. They seem to make her pussy particularly wet, especially if the men in them have really huge cocks.
The thought of Stella fucking a bunch of well-hung studs has always been a big turn-on for me too. We often talked about it over the years, but Stella never seemed to take the idea seriously. During these conversations I would often ask her how many guys she thought she could fuck at one time. Her answer was always the same: “It would depend on how horny I was, but if I was really hot, and the guys were young and good looking, maybe seven or eight.” Then she would laugh, as though the whole idea was a joke.
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My husband and I have been married for over 25 years, and our children are grown and have moved away from home. Ike, my husband, is 52, and I am 47. I am five feet 10 and weigh around 170 pounds, with shoulder-length black hair and brown eyes. I work out several times a week and am still in good shape, and Ike and I have always had a great sex life.
We live in a two-story house, and our master bedroom overlooks our pool, as well as that of our neighbors, Tim and Annie, with whom we are quite friendly. One morning about a week ago I looked out of our bedroom window, and nearly gasped at what I saw. Tim and Annie’s 22-year-old son, Ron, home from college for the summer, was swimming in their pool, along with two of his friends, and all three of them were nude.
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My wife Holly and I have been married for almost 40 years, and we are still very much in love with each other. Holly has long dark hair and brown eyes. She is five feet ten, weighs around 145 pounds, and measures 36C-29-32, with a great set of breasts. We have always had a great sex life, and Holly is always horny and loves to fuck and suck cock.
To celebrate our anniversary last year, we decided on a five-day trip to Las Vegas. We planned on taking in some shows, checking out all the new casinos and generally having a good time.
Now one of my favorite fantasies has always been to watch my wife having sex with a well-hung young man. Holly had long known about this fantasy, and had admitted that thinking about it turned her on too. Usually our fantasy had involved a young guy who we meet in a bar or on vacation.
About three days before we left for Vegas, I came home from work early, and couldn’t find Holly. I called out for her, and heard her call back from upstairs, saying that she had a big problem and really needed my help. I ran upstairs to our bedroom and found my wife sprawled out on the bed, naked. Her knees were pulled up and spread wide apart, her head lying on a pile of pillows. She looked fantastic.
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My husband Isaac and I are both in our 50s, but we are in good health, in good physical shape and very sexually active. I still have a pretty nice figure for my age, and I am open-minded and sincerely enjoy all kinds of sexual experiences.
Although our physical relationship has always been good, as with many couples who have been married for over 30 years, routine and habit eventually took its toll, and we finally decided to embark upon some erotic adventures in order to keep things interesting and spicy. I would not define us as hard-core swingers by any stretch of the imagination, but over the last five years we have engaged in a couple of serendipitous trysts, and done the spouse-swapping game with a few other select couples. We both found these periodic exchanges to be pretty exciting and sexually stimulating.
About nine months ago, our favorite local steak house hired a new waiter, who turned out to be very interesting. Ramon was a divorced man of 42, very handsome, six feet five and well built, though not overly muscular, with a light brown complexion and a charmingly sincere manner. After we got to know him, he told us that he was part Spanish, with a little Creole mixed in from his mother’s side, and a splash of Irish and Dutch from his father’s.
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I am a 50-year-old man who has been divorced for more than 10 years, and hasn’t dated much since. Some of the people where I work have tried to fix me up with someone’s friend or relation, but that kind of thing usually just ends up with somebody getting upset. Until recently I satisfied my sexual urges with a lot of masturbation, and a rare visit from my first wife.
One of my fellow workers is a woman named Doris, who was in somewhat the same situation, having been divorced for four years. Although she works in a different department, we would often run into each other around the office, or at work-related parties. The last few times we talked I had the feeling that we related to each other as more than just work friends. She had an intriguing look about her, and each time we saw each other our connection seemed to deepen.
Doris is a good 10 years younger than me, and still has an excellent figure, which, I must admit, was what first attracted me to her. She is five feet six, with long dark hair, deep brown eyes, shapely medium-sized breasts, curvy hips and really long gorgeous legs.
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I recently had the misfortune of listening to a fellow worker describe his feelings when he found out that his wife of eight years was having an affair with some guy. He went into great detail as he related how he had become ill one day and had gone home early from work, to find his wife on her knees on their bed, screaming into a pillow as some guy with a long pecker pumped into her pussy from behind. He was devastated, and said he would probably never trust her again.
I have to admit that although I felt sorry for him, I was thinking more of my own situation, since Delia and I have been married almost seven years. I wondered how I would take a similar situation if it happened to me. After much thought, I decided to take steps to assure that it never would.
My slim, attractive wife looks to be barely 21, but is actually 29, with a winning smile, a great set of tits, a trim waist and a tight ass. She turns many a guy’s head when we go out, which made my worries seem even more important.
We had just finished one of our twice-weekly sexual encounters when I started asking her some pertinent questions. Since I was the only man she had ever been with, my first question was, “Have you ever wanted to experience sex with another man? Tell the truth,” I added. Delia’s immediate response was to ask me how I ever came up with a question like that. I told her of my friend Teddy’s experience with his wife, and when I finished I asked her the same question again.
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It had been a normally uneventful week, and I was looking forward to the same kind of weekend when I arrived home late Friday afternoon to find Ivy, my beautiful wife of 10 years, in an unusually troubled state of mind. She seemed preoccupied and jumpy, and appeared to be doing her best to avoid me.
Knowing Ivy as I did, I knew she would tell me what was on her mind sooner or later, so I refrained from questioning her. We got through supper and a mostly silent evening of TV viewing until around 11, when I announced that I was going to bed. Ivy said she would join me shortly.
About half an hour later she came into the bedroom, and seemed a bit disappointed to find me still awake. I could sense the anxiety in her as she turned her back to me and started to undress.
My wife Anna and I were going away for a long weekend, on a “marriage retreat” at a mountain lodge owned by our sex therapist, Lilly, and her husband. Anna and I are in our 40s and have been married for 18 years, and recently our love life had gotten a bit stale. I still considered Anna attractive, with her petite frame, thick, silky blonde hair, soft natural breasts and gently flaring hips. But our busy life and our kids had tended to sap both of us of our interest in sex. Once Anna got aroused she was a wonderful lover, but the problem was getting her interested, let alone excited. It had been a joint decision to consult a sex therapist in an effort to renew our passion. We had been seeing Lilly for the last four months, and it turned out to be one of the best decisions we had ever made.
This was the first time we had attended one of Lilly’s weekend group therapy sessions, and both of us were a bit nervous about it. The sessions were supposedly very intense, and involved opening up and sharing with other couples, both emotionally and sexually, in order to become more comfortable with our own bodies and to explore new and interesting approaches.
On the drive up to the lodge, I told Anna that it was still not too late if she wanted to change her mind and turn back. She replied that the thought had crossed her mind, but we needed a vacation in any case, and some new experiences might do us good—as long, she added, as we wouldn’t be expected to share any private fantasies, or to get too explicit in front of anybody else.
It all started about six months ago, when my husband Ellis lost his job. When the unemployment benefits ran out before he could find a new place, money began to get tight. After much discussion, I decided to look for housecleaning jobs on Saturdays. This would not interfere with my full-time job, and would still leave my Sundays free, while bringing in a little more money.
By a lucky chance, it turned out that Hal, a friend of my husband’s, was looking for someone to come in and clean once a week. Hal was a single professional, and had a very nice home within a short drive of our house. He was about five years younger than Ellis, and seemed like a very nice gentleman. We quickly agreed on a fee, and he asked me to start that very weekend.
On Saturday morning I drove to Hal’s house, arriving promptly at nine o’clock. His home was very nice, consisting of two floors and a full finished basement, made into a game room, complete with sofas, a poker table and pool table. The house was not filthy, but it was in need of a good cleaning and straightening up. I started in the basement and worked my way up, straightening, dusting and vacuuming industriously. For most of the day Hal stayed in his office, which he told me I did not have to clean. At the end of the day he paid me in cash, and I drove home thinking that this was going to work out very well.
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