As I moved to her she reached out to unbuckle my belt, then undid my pants. They fell, and my cock sprang from my shorts. Joanna traced the underside of my rod with her fingernails. Then she bent to me, and suddenly I felt her warm mouth sucking on my cock, her tongue twirling around the head. We both knew it wouldn’t take me very long to pop.
I tried to pull away, to get her to lie down so I could put my cock into her, but she put her hands on my ass and gripped my buttocks tightly, preventing further movement. Then she slipped her middle finger into my rectum, finding my prostate and massaging it. I couldn’t hold off any longer, and I went off like a geyser, shooting all I had into her mouth, past her tongue, and down her throat.
When she pulled away from me, she had a smile on her face, and I was panting hard. “Damn, that was great!” I said breathlessly. “But what about you, honey?”
Her smile got even wider. “Well, I could use a mess of long-lasting French kisses wherever you think they would do the most good. But catch your breath first, baby, okay?”
I did the best I could, but the fact is that I’ve hardly been able to catch my breath with her ever since.
—T.P., Johnstown, Pennsylvania
Highway Hummer
I had left about ten minutes early for the long commute home, hoping to beat some of the heavy traffic. As I pulled onto the interstate a car driven by a dark-haired woman pulled over from the next lane, almost hitting me. I quickly honked the horn to try to head her off, and she gave me a very dirty look.
As I drove on, I soon noticed that that same woman kept pulling up beside me, staring at me through the car windows. I couldn’t tell if she was pissed off at me or if she was trying to apologize or what, but I gave her a smile just to keep her happy.
Then, as I was about to exit the freeway, she suddenly cut right in front of me, and I saw she was waving at me to follow her. So I did.
We stopped in the first parking lot we came to. She pulled up close to my car and waited for me to get out. As I walked up to her car I noticed that she was kind of overweight, but still quite attractive, with long, thick dark hair, pretty eyes, and cleavage that a man could get lost in.
I wasn’t really sure of what to say, but luckily she started talking as soon as I reached her. She said she wanted to apologize for cutting me off on the freeway, and asked if there was anything she could do to make up for it.
Well, considering that I had never seen this woman before, and would probably never see her again, I figured what the hell. In a kind of joking manner, I told her that if she gave me a blowjob we could call it even. I nearly died when she told me to pull it out.
But I did pull it out. She gasped and told me how big I was, licking her lips teasingly. Then she leaned over and took me in her mouth. I was so excited I had to fight to keep myself from coming right then. As she was sucking me she kept pulling my cock out of her mouth to lick around the head. Then she would look up at me and ask if I liked what she was doing. I answered her by shoving my cock into her mouth as far as I could, and she took it all easily.
After a couple of minutes she stopped and turned her head away from me. I didn’t realize what she was doing until she turned back to face me, and I saw that she had removed her false teeth! I really wasn’t sure how to react to this, until she started biting the length of my cock with her soft gums. I had never felt anything like that before. It was great!
At this point there was just no way I could hold back any longer, so I didn’t even try. She was sucking and stroking and biting my cock with those soft gums, and I was about to blow like a frigging volcano.
I guess she knew I was about to come. She took my entire cock in her mouth while she unbuttoned the top three or four buttons of her shirt. Then she pulled her mouth away and started stroking me with both hands. “I want you to shoot off all over my tits,” she told me. “Would you like that?” I was too far gone to say anything. Then she started urging me on, saying, “Come on, baby. Shoot it on my tits. Oh, yeah. Lemme have that hot come on my tits. Come on, baby. Shoot it all.” And she was moaning like she was having the best time of her life. Needless to say, I shot off like a rocket. I had never come so copiously before. And as I spurted and spurted she rubbed the come into her tits, still moaning like crazy.
By the time I finished, the entire front of her shirt was soaked. It didn’t seem to bother her, though. She just started up her car and drove off like nothing had happened.
I never did see her again after that, but you can be sure I think about her every time someone cuts me off in traffic.
—V.B., Savannah, Georgia
The Older Generation
My fiancée, Deborah, and I were recently invited by Howard and Evelyn, Deborah’s parents, to vacation with them in Jamaica to celebrate Evelyn’s fiftieth birthday. Deborah is an only child and very close to her parents, so she definitely wanted to go. I get along very well with Deborah’s parents, so the idea of spending a week with them in Jamaica sounded like great fun.
Howard and Evelyn met Deborah and me at the airport when we arrived. They had gotten there earlier in the day, and had already been to their rented condo and topped off the food and booze. It felt great driving across the island in a convertible with Evelyn and Howard, with the wind blowing in our hair. A lot of guys might have dreaded vacationing with their future in-laws, but Howard and Evelyn were a fun couple and more like slightly older friends of Deborah’s than conventional parents. In fact Deborah has said she considers Evelyn to be her best friend.
The condo was a two-bedroom unit with an amazing view of the sparkling blue ocean and a beautiful sand beach. Deborah and I agreed that this was going to be a great vacation. We quickly unpacked and decided to hit the beach that afternoon.
On the beach I thought to myself how lucky I was to be engaged to a girl like Deborah. She’s an attractive, sexy blonde with a great figure, and in my opinion had one of the best-looking bodies on the beach. I was equally impressed with her mother. Even though we were here to celebrate Evelyn’s fiftieth birthday, I thought she was the runner-up for the title of best-looking woman on the beach, second only to Deborah. Evelyn was wearing the kind of bikini that few fifty-year-old women could wear, and she looked great in it.
Like her daughter, Evelyn was blonde, beautiful, and in incredible shape. She could easily pass for a woman of forty, or even younger. She and Deborah looked more like sisters than mother and daughter. In fact on the beach, from the back, it was tough to tell the two of them apart.
Evelyn was one of the reasons I had decided to engage myself to Deborah. In college one time, a guy had told me that if I was curious about what a woman would look like in twenty or thirty years, I should check out her mother. So when Deborah and I had started dating and I met Evelyn for the first time, I definitely liked what I saw, and I figured if that was how Deborah would look in the future, I had nothing to worry about.
My only reservation about Evelyn was that she was a very strong-willed woman and liked to have things her own way. Fortunately, while Deborah had her mother’s body, she had inherited her father’s more easygoing personality.
The four of us had a great time sunning, swimming, sailing, snorkeling, and putting in lots of beach time during the day, and exploring the local nightlife at night, when we weren’t having our own little party in the condo. Deborah and I had some great sex during that vacation, and more than once I heard Howard and Evelyn getting it on in their room down the hall, and it sounded pretty wild. I mentioned this all to Deborah, and she said that her parents had always had a pretty active sex life. I figured that Howard was almost as lucky as I was.
In fact during that vacation I became increasingly aware of my future mother-in-law’s sexuality. One afternoon I spied Deborah—as I thought—from behind on a secluded stretch of beach. Running up behind her, I grabbed her around the waist and lifted her off her feet. I nuzzled her neck and licked it as I cupped one of her breasts and pressed my cock against her ass. I whispered in
her ear that she was a cock-tease, and that I couldn’t wait to get her back to the condo, strip that bikini off her, and give her the fucking she deserved. I was shocked to the core when I heard Evelyn’s voice saying, “Well, that’s fine with me, darling, but what will my husband and your fiancée think of that?”
Damn! From behind Evelyn looked so much like Deborah that I hadn’t realized I was propositioning and feeling up my future mother-in-law instead of my girlfriend. I apologized profusely, but Evelyn told me not to worry about it, saying that it was flattering that I had mistaken her for Deborah. She promised that my case of mistaken identity would be our secret. Later, after I had gotten over my embarrassment, I kept thinking how good Evelyn had felt in my arms, and how firm her breasts had been. At fifty, Evelyn’s breasts were as firm as those of her twenty-three-year-old daughter.
Another time the four of us were snorkeling near a reef. I was taking a break, hanging on to the ladder at the side of the sailboat. Evelyn surfaced a few feet away, swam over to me, and joined me at the ladder. The waves kept pushing her into me, and I felt my cock rising every time her body bumped or brushed against mine. I loved the sight and feel of her breasts, which were barely held in check by her bikini top. A few times I felt her lower body brush up against my erect cock.
At one point Evelyn changed her hold on the ladder, which brought our bodies closer together, and then wrapped her legs around my waist. She said that should stop us from bumping into each other. And it did, but it also kept her breasts pressed firmly into my chest, and my stiffening cock pushing against her pelvic area. Evelyn kept talking about the coral and the fish, never letting on that we were in a highly sexual position. When Howard and Deborah surfaced about thirty feet away, Evelyn immediately unwrapped her legs from me and swam off, leaving me with a painful hard-on. I couldn’t help wondering if Evelyn was coming on to me or if it had all been innocent and I was imagining things. That night I had a very erotic dream, but it was about Evelyn, not Deborah.
The next day the four of us were scheduled to take a tour boat to a nearby island. I was kind of beat, not having slept much the night before, and decided to stay back at the condo. Deborah debated staying with me, but finally decided to go with her parents. After they left I read for a while, and then decided to lie down for a nap. I closed the blinds in the bedroom, took off my clothes, and stretched out on the bed.
I’m not sure how long I was asleep, but I woke up in the most incredible state of horniness. With the blinds closed it was dark in the room, but I could make out the blonde head bobbing up and down on my cock. Deborah always gives pretty good head, but this time she was really outdoing herself. She was doing something new with her tongue that was just driving me crazy.
Now I admit that the thought may have gone through my head that maybe this wasn’t Deborah; but if so I quickly put it out of my mind. Of course it was Deborah, I told myself. She must have decided at the last minute to not go with her parents, and had come back to the condo. In a hoarse voice I told her to swing around so that I could return the favor and eat her pussy. She pivoted around, never removing her mouth from my cock, and positioned her knees on either side of my head. I reached up for the cheeks of her ass and pulled her pussy down to my face. I noticed that her blonde pubic hair was thicker than usual; I hadn’t realized she was letting it grow out on this trip. (At least that’s what I told myself.) I found her clit with my tongue and was rewarded with the sound of a muffled groan of pleasure as she continued to suck my cock. We continued in this position for several minutes, until she pulled her mouth off my cock and I heard her groaning as she climaxed. There is nothing I enjoy more in life than pleasuring my beautiful fiancée, and I eagerly sucked her juices out of her pussy.
I told the lady that I wanted to fuck her with my cock, and she repositioned herself on her back, spreading her legs wide. I got between her thighs and began to ease my cock into her. I felt the head of it slide between the lips of her pussy, and the shaft slowly followed. She was groaning as my cock moved deeper inside her. I noticed her groans were muffled, and could just make out in the dark that she had her face buried in a pillow and was moaning into it. I reminded her that her parents were gone and she could make all the noise she wanted to, but she just kept moaning into the pillow.
I started to fuck her then, taking deep strokes into her pussy. I felt her wrap her legs around my waist and lock her ankles behind the small of my back. Her pussy felt wonderful. I wanted to kiss her, but she still had her face buried in the pillow, and maybe, just maybe, there was something inside me telling me to leave things that way.
After fucking her for several minutes, I noticed that the woman beneath me was doing something with her pussy that I had never felt before. She was somehow flexing the muscles of her cunt around my cock, making it feel as though it was being squeezed by a gentle hand. It felt great, but I wondered where she had learned that trick. I was getting very close to shooting my load inside her when a sudden breeze came through the window, causing the curtain to flap open, and in that moment I got the shock of my life. Or so I told myself.
Lying nude underneath me, with my cock inside her, was not my girlfriend, Deborah, but Evelyn, my future mother-in-law! In the brief flash of daylight that illuminated the room, Evelyn saw the recognition in my face and said, “Surprise!”
Well, whether it was a true surprise or not, I knew that now I should immediately pull my cock out of her. But with Evelyn’s legs wrapped tightly around me, and that squeezing thing she was doing with her pussy, it was too late. I felt my cock swell before the come started shooting out of it into my girlfriend’s mother’s pussy. I couldn’t stop myself, and at that point I didn’t want to. Evelyn was coming again also, and this time I watched my future mother-in-law’s face contort and heard her full-throated screams of ecstasy.
When we had both recovered I pulled my cock, coated with a combination of my come and her juices, out of Evelyn’s pussy and asked her what the hell was going on. Evelyn explained that when I had mistaken her for Deborah on the beach the other day and propositioned her, it had gotten her thinking about what it would be like to have sex with me. She had gotten a feel for the size of my cock in the water by the boat the day before, and realized that I was pretty well hung, so she’d decided to treat herself to a special fiftieth birthday gift by fucking me. When I said I was going to stay at the condo today, it had seemed like a perfect opportunity. She had faked a migraine and told Howard and Deborah she would take the car back to the condo and then pick them up at the docks later that evening. When she had gotten here and found me sleeping in the nude with the curtains closed, she had simply taken advantage of the situation.
Evelyn said she had assumed I would realize she wasn’t Deborah at some point, but it had gotten to be a game to see how much time would go by before I figured out I was fucking her and not my fiancée. She had purposely avoided speaking to me, and she only groaned when she couldn’t help it.
I was pretty upset, though it was at myself more than at Evelyn. I had never cheated on Deborah before, and now I done it with her mother, of all people. Even though I tried to convince myself that it was unintentional, deep in my heart I knew better. Surely I had realized that there was at least a possibility that the woman I was fucking was Evelyn and not Deborah, but I had done nothing to stop it. I had even eaten her pussy and sucked the juice from it, for goodness sake!
Evelyn, however, was not interested in my pangs of conscience. She said I should be honest with myself; we both knew I had been lusting after her for a long time. I denied it, but Evelyn said I was a poor liar. Even Deborah had told her that I thought she was a very sexy older woman. She said I had to admit that we were great in the sack together and that the sex had been awesome for both of us. Then she pointed to my cock, which was rising again even as we talked, and said that my dick certainly seemed to like her. She was right, and I finally admitted that I had wanted to fuck her since the day I met her, but never had the nerve to do anyt
hing about it.
Finally Evelyn said, “Enough talk,” and she pushed me onto my back and mounted my erect cock. She then rode me for two or three orgasms before I came again. We rested for a few minutes and then fucked again, and then again and again, for the rest of the afternoon. Once I got over the shock of the whole situation, I really was into screwing Evelyn, fucking her with the deepest, fastest, hardest strokes I could produce. I wanted to wipe the smug look off her face, and I did that every time I brought her to orgasm and she screamed and moaned and told me what a cock-hungry slut she was. I even fucked her ass a couple of times. We finally had to stop so we could shower and go pick up Howard and Deborah at the docks.
The rest of the vacation passed in a blur, with Evelyn and me having sex with each other whenever we could be alone for a few minutes. The last couple of nights we snuck out of our bedrooms in the wee small hours of the morning, leaving Deborah and Howard asleep, to have sex on a secluded stretch of beach we had found a few hundred yards from the condo. We did it under some low-hanging tree limbs that made it almost like a cave, with the stars above us and the roar of the waves a few feet away. Our cover story, in case Howard or Deborah ever discovered us gone, was that we couldn’t sleep and had gone for a walk on the beach, but we never had to use it. It was very romantic having sex on the beach, although Evelyn said she kept having to wash sand out of her ass and pussy.
Now Deborah is great in bed, but her mother is an all-star, on another level of sexual skill and intensity altogether. She can do things to a man that I didn’t even know were possible. Evelyn is vague about where she learned to do some of these things, but I strongly suspect it wasn’t from Howard.
Our vacation finally ended, and we flew home. I haven’t seen Evelyn since we got back, as she and Howard live in another city, but I think about her all the time. Fortunately, she and Howard are scheduled to come for a visit soon, and Evelyn has already sent me an e-mail telling me how she can’t wait to fuck me, and that I should start thinking of ways we can slip away from Deborah now and then. I already have a few good ideas.
Letters to Penthouse XXXXIV Page 6
