Serendipity
HIS GIRLFRIEND WAS HOT, BUT HER MOTHER WAS
HOTTER—NOT TO MENTION THE CALL GIRL
I am going to tell you about something that happened to me thirteen years ago, when I was in the military and stationed in Florida. I met a girl there named Dinah. She was just eighteen, a year younger than me, a hot-looking girl with big tits and an ass to die for. We dated for about six months, and during this time I was introduced to her family, including her mother Loretta.
Loretta was forty-one years old and had a hotter body than her daughter. Her measurements were 40D-27-37. She had long black hair, tanned skin, and fabulous legs, and could easily pass for twenty-six. She usually dressed conservatively, except on weekends, when she would wear shorts and tank tops. Her husband worked in some government laboratory, and Loretta worked part-time in the library. They seemed to be very well off.
One day I was invited to a party that Loretta’s husband was throwing for his coworkers and their families. By around midnight almost everybody was fairly well drunk or passed out, and Dinah started driving people home. While Dinah was out, Loretta asked me to help her take her husband upstairs, since he was one of those who’d passed out, and she was a little tipsy herself. When we came back down she asked me if I thought she was good-looking, and I told her I certainly did. Then she told me she wanted to show me something. She brought out a small photo album, and when I opened it I got the shock of my life. There were pictures of her in teddies and very skimpy nightgowns. She told me she’d had them taken for her husband’s birthday a few months ago, but he had just gotten mad at her and told her she was too old to act like that, which of course had hurt her. Then she told me that her husband only had sex with her about once every two months, and then it only lasted a few minutes. At that point she came right out and asked me if I would fuck her.
My dick got hard instantly, but I told her that she was my girlfriend’s mother, and she was drunk, and in the morning she would feel differently. Loretta said she would still want to fuck me even when she was sober, and Dinah didn’t have to know. I then said that if she still felt that way the next weekend, I was going to be in Miami on a four-day pass. I told her what motel I would be staying at, but I didn’t really think she was serious.
A week later, I had just arrived in Miami and was settling into my room, when there was a knock on my door. When I answered, there was Loretta, dressed in one of the shortest miniskirts I have ever seen, along with a cutoff top, six-inch heels and a lot of makeup. She looked like a high-priced hooker, and I got my biggest hard-on to date.
Loretta walked past me into the room. “Are you surprised to see me?” she said. Without waiting for an answer, she sat on the edge of the bed and beckoned me over with her finger. As I stood in front of her she told me she had three conditions for the weekend, and she would tell me what they were after she sucked my dick. She then pulled down my sweat pants, stuck out her tongue and started to lick my cock from base to tip. Then she took the whole thing into her mouth and proceeded to give me one of the hottest, wettest blowjobs I have ever had. I came in about ninety seconds, and she swallowed every drop, after which she got up and gave me a deep French kiss. I was so surprised and shocked that I hadn’t yet said a word.
When we broke our kiss she told me her three conditions. One, I was never to tell anybody about what we did. Two, I was to treat her like my personal slut. And three, for the next four days we would live out our wildest and most intense fantasies, no questions asked. If I could abide by those conditions, she would be and do anything I wanted for the next four days. I told her that was fine with me. Then I laid her back on the bed, pulled her legs apart and started to eat her pussy. Just before she came I switched to her asshole, and that took her over the edge.
After we regained our composure, she said she had a surprise for me. She opened her purse, gave me her credit card and told me we were going to the nearest sex shop so I could pick out whatever I wanted for our time together. We went downstairs and got a cab. During the ride she grabbed my hand and put it on her pussy, then started to fuck herself with my fingers while whispering to me how much of a slut she was going to be. When we arrived at the shop we picked out a bunch of dildos, butt plugs, anal beads, vibrators and—at her suggestion—an instant camera and a whole bunch of film.
Then Loretta noticed the viewing booths, and asked if we could go in and watch some movies. The booths were clean and roomy and had a selection of eighty channels. As we watched one of them, Loretta opened my fly and started stroking my cock. Then she got up and pulled off her panties. She sat down on my lap, facing me, straddling my thighs with her cunt over my dick, then slowly sank down on it. Her eyes rolled back and she proceeded to fuck me. Soon she was telling me what a nasty whore she was, and begging me to come inside her. Between her dirty talk and her wet, tight pussy I lasted about two minutes. After I came she hopped off and reached for some tissue from the box on the wall, but I stopped her. I was getting into it now, and I told her that if she wanted to be a true slut she would walk out with my come dripping down her legs. Loretta just smiled and gave me her panties, and we walked out with my hand on her ass.
When we got back to the room, Loretta asked me which one of my fantasies I wanted to act out first. I said I wanted to take pictures first, because without them I would never believe this hadn’t been a dream. Loretta loaded the camera, handed it to me and asked me what I wanted her to do. First I had her lie back on the bed, pull up her skirt and start rubbing herself while I started snapping away. I handed her a silver vibrator and she started rubbing it on her clit, then slid it into her pussy. While she was bringing herself off, she asked me to take out my cock so she could look at it.
Next I asked her to get on her knees with her ass in the air, and pull her ass cheeks apart. She looked back at me and said that if I intended to fuck her asshole I better go slow, as it had been many years since she’d had it in the ass. I nearly came again when I saw her smooth, shapely behind, with the most beautiful puckered brown eye I have ever seen. I told her I had to lick that ass and tongue-fuck her anus, which I proceeded to do, continuing to take pictures in between licks. When her ass started to open up under my tongue, I took the anal probe we had bought, had her lick it and then slowly inserted it into her back passage. By this time she was so hot she was begging me to fuck her ass, so I let her lick my dick to get it nice and slick with her spit. Next I pulled the probe out of her, put the tip of my dick against her asshole and gently pushed forward. She let out a low moan of pleasure as the head of my cock broke past her tight sphincter ring. I held still for a minute so she could get used to it, but she looked back at me and told me to fuck the shit out of her. “Fuck me like a whore,” she panted. “Tell me I’m your slut bitch, and fill my asshole with come, you bastard!”
As I proceeded to do what she wanted, I grabbed a flexible dildo, reached underneath her and put it in her pussy, which was literally leaking pussy juice. Soon she started screaming that she was coming. As I felt her asshole tighten up I couldn’t hold back any longer, and I blasted her ass full of come.
As I pulled out I told her not to move. I got one of the butt plugs we had bought and inserted it into Loretta’s gaping hole, letting her asshole close around it. Then I walked around her and told her to clean my dick. That was a mistake, because what started as a cleaning job turned into another blowjob; but this time she inserted her middle finger into her pussy, got it wet, then slipped it into my asshole and finger-fucked me until I came in her mouth.
I was hungry now, and I suggested that we go down to the restaurant and get a little snack, then come back up and fuck some more. I told Loretta not to clean up, to leave the butt plug in and her panties off. Loretta told me I sure was kinky for a young guy, but she loved it. We got a lot of funny looks in the restaurant as Loretta kept wiggling around on the plug in her ass. I wondered if they could smell the sex on her.
Over the next few days we did everything we coul
d think of with each other, and lived out our most far-out fantasies. On our last night Loretta handed me a phone book which was open to the section on escort services, and told me to pick one, and to tell her what kind of girl I wanted. I said I wanted one just like her, but blonde and younger. Loretta went out, and I dozed off for a couple of hours. I woke up when I heard her walk in, but she was not alone. With her was a beautiful blonde with long hair, big tits and a great ass. “Surprise, lover!” Loretta said.
The blonde walked up to me and kissed me, stroking my cock through my shorts. Then she told me her name was Crystal. Loretta came up behind her and started licking her neck as I pulled up her blouse and started sucking her big firm tits. Loretta told Crystal to get down on her knees and deep-throat my cock, and as she did so Loretta got behind me, pulled my ass cheeks apart and stuck her tongue deep in my asshole. I came instantly in Crystal’s mouth. She held my come there as she got up and kissed me, giving me back my own jism; then I kissed Loretta and she gulped it down.
Crystal got on all fours on the bed. Loretta pulled up her skirt and proceeded to tongue-fuck her ass, getting it ready for me to fuck. I was hard again in minutes. Loretta took my cock in her mouth to coat it with her saliva, then guided it to Crystal’s asshole. I quickly sank in and started to fuck her with slow, steady movements. I was so engrossed in fucking that tight hole that I didn’t realize that Loretta was behind me until she whispered in my ear, telling me to relax and enjoy. She then squirted some K-Y jelly on my ass crack and started to slip her finger up my asshole. Then I really got a surprise. Loretta had gotten the strap-on dildo we had bought and put it on. Now she removed her finger and slipped the head of the dildo into my virgin back door.
Now I am not gay or anything, nor do I intend to become so, but after my initial surprise and shock, I found that I was enjoying the stimulation. Loretta proceeded to fuck my ass, her thrusts driving my dick deeper into Crystal’s clutching hole, and I was loving every minute of it. I groaned loudly as I came in Crystal’s ass.
The two women now laid me down on my back, and Crystal positioned her asshole directly over my face, so that my own come dripped out into my mouth as I ate out her ass, savoring our combined flavors. The moaning blonde leaned forward to take my flaccid dick into her mouth, as Loretta put my legs over her shoulders and started to ass-fuck me again. After a few minutes she unsnapped the strap-on, leaving it still in my asshole, and traded places with Crystal. Then Crystal was fucking my ass and I was eating Loretta’s tasty anus, while the two of them kissed each other just above my head. By now I was hard again. Crystal pulled out of my ass and the two of them took turns sucking and licking my cock until I shot into their open mouths.
Loretta and I left the following day. Loretta took the bus home, and I hitched a ride back to the base. We managed to get together three more times in the next six months, while I still continued to date Dinah. No one ever knew what was going on between us. If you should print this letter, please don’t print my name or address, as I don’t think Dinah, now my wife, would appreciate finding out about this.—Name and address withheld
SHE USED TO BE THE CAMPUS SLUT.
DID SHE EVER CHANGE? ASK HER HUSBAND
My wife Marion was a slut when she was in college. There was a widespread slogan on campus: “If you get a hard-on, go see Marion.”
She had started college as a cute, chubby, lonesome girl, but by her sophomore year the ugly duckling was changing to a beautiful swan. The guys took notice.
Rob was one of the big men on campus. He and five of his fraternity brothers were known as the “six-pack,” both for their well-defined abs and their fondness for beer.
One night Rob’s fraternity took over an empty house for a sleepover party. They hauled their mattresses from the frat house, got loaded up on beer and brought their dates for a night of fun and frolic.
Marion was invited by Carl, a tackle on the football team. It was the first time she’d been asked out by any of the “in crowd.” Carl was a big puppy dog. He drank beer by the gallon, and pretty soon he had passed out on the carpeted floor. That left Marion on her own. Some time later Rob arrived. He told Marion that his date had passed out too, and he sat down on one of the mattresses with her to comfort her.
Rob was charming, talented, intelligent, clever, handsome and—rumor had it—well hung. He was said to be able to charm any girl out of her virginity. He accomplished this quite easily with Marion, who was anxious to be included and be part of the crowd. Rob found that she was willing to do anything to please him. She sucked her first cock that night, as well as losing her virginity. Rob was good, and he had a lot of experience. He taught Marion so well that she was addicted to sex from then on.
After that, Rob found her a willing and eager pupil. She was what he called a natural. He never took her out on a regular date, just had easy sex with her whenever he felt like it. Meanwhile he was dating a girl named Margot, who was frigid but socially desirable.
Toward the end of Rob’s senior year, Marion naively started talking about marriage. Rob had to explain to her that, though he loved her (he said), he had a lot of ambition. Margot came from money and power, and he had to marry her to get where he wanted to go. He told Marion that Margot wasn’t half the woman she was. In fact she was a cold fish. Margot would be his wife, he said, but Marion could be his mistress, and he would always take care of her. Marion slapped his face and ran back to her dorm.
Marion turned for consolation to Louis, another member of the “six-pack.” At first she just wanted a shoulder to cry on, but to Louis it meant that he was about to score with the girl his friend Rob said was the most sexually liberated female on campus. He was right. He had never experienced such a variety of sexual activity in his life. Soon each of the other six-pack members was treated to sex beyond his wildest dreams. Then they thought it would be wild to have her “pull a train.” This was Marion’s first, but not last, gang bang on campus.
At first she did it all to get back at Rob, but she loved the attention and the desire she inspired in the guys, and she thrived on the sex. Of course the guys couldn’t help bragging about their exploits with her, and soon others came around. That’s when the slogan was created—”If you get a hard-on, go see Marion.”
It was in Marion’s senior year that I met her. We had several classes together, and I started talking to her during breaks. Eventually I asked her for a date, and she readily accepted. The final outcome was that we were married a year after we graduated. Marion knew I was aware of her reputation and her exploits, but I assured her that I loved her just as she was and wouldn’t change her for anything.
Things were fairly normal for a while, but by our second year of marriage I could tell that Marion was becoming restless. I finally got her to admit that she was attracted to a guy at work who was always coming on to her. Benny had a reputation much like Rob’s. He too was very handsome and charming. I encouraged Marion to have a fling with him. I said I would enjoy hearing about it all when she got home, just as she had told me about Rob and his friends. She knew how horny and excited I got when she related her experiences in college. Actually I often had her tell me about it as foreplay.
Marion did eventually go out with Benny, and of course he fucked her brains out. I enjoyed it almost as much as she did when she told me about it. She was so turned on by this first extramarital affair that she had no qualms about fucking other men if she was attracted to them. She always shared every detail of her liaisons, which turned us both on. I didn’t mind how many men she had, and I still don’t, because I know that it is me she loves and trusts, and that we have a relationship that is far more than just sexual.
Benny has now become a very close friend. He feels free to come and take Marion out for a night of dinner and dancing while I baby-sit. They either go to his place afterward for sex, or come back here and use our bed for their fun and games. The door is always open for me to watch, listen or sometimes participate. We are all happy with this situ
ation, strange as that may seem to many. To each his own, I say, and this is mine.—B.K., Amarillo, Texas
IN THE BIG CITY HE BOUGHT HER A BIG DILDO
AND THEY BOTH GOT A BIG THRILL
My wife and I have always enjoyed a great sex life throughout our twenty years of marriage, and over that time we’ve managed to come up with ways to keep it exciting for both of us. We often share our fantasies with each other as a part of our foreplay, and sometimes we choose to act them out. Let me share one such event with you.
About a year ago we decided to get away and spend a special weekend in the big city, just enjoying each other. Arriving on a Saturday morning, we spent a few hours at the nearest mall, shopping for a dress for Georgia to wear to dinner that night. She tried on several, but nothing really turned either of us on. While she was in the dressing room I picked out a short skirt and a sheer top and took them to her. I waited patiently for her to come out and model the outfit for me, but when she opened the door she had changed back to her own clothes. I told her I really wanted to see her in that outfit, but she just grinned and said I would have to wait until dinnertime. We then made a stop at Victoria’s Secret, where Georgia bought a black demi-bra and a pair of open-crotch pantyhose. Then we headed for our hotel and checked in.
When it was time to dress for dinner, Georgia suggested that I go ahead and get dressed, and then leave while she got ready. She said she would meet me down in the lounge at seven o’clock, and that I should try to pick her up there, pretending that we didn’t know each other. She gave me a passionate kiss to send me on my way.
Letters to Penthouse XVIII Page 15