I’d flown into Chicago at 11, and had been negotiating contracts with a customer all afternoon, so I was beat when I reached my hotel at five-thirty. I checked in and was relieved to find that my baggage had arrived and had already been taken up to my room. I thought of calling my husband to tell him I’d arrived safely, but I needed a drink, so I stepped into the lounge, finding a table in back where I could relax.
I ordered a shot of bourbon with a beer chaser. As I waited for it to come I found myself automatically reaching for my briefcase, but I stopped myself. How the hell was I going to relax if I kept working? Then I remembered I had a copy of my favorite magazine in the briefcase, so I carefully retrieved the latest issue of Penthouse Letters.
Since I travel on business frequently, I had made a plastic folder with the covers of a popular woman’s magazine pasted on the front and back, in which I could sleeve my copy of Letters so I could read it anywhere without drawing unwanted curiosity.
I was soon getting pretty turned on by what I read, and being fairly isolated in my corner, I inched my hand under my short skirt to rub the wet crotch of my panties. I was trying to put myself in the place of the woman whose letter I was reading as she described feeling a man who was not her husband slipping his long hard cock into her quivering cunt. I circled my finger around my clit, and a few seconds later I came, just as the woman’s stud shot his semen into her unprotected womb.
I looked around quickly, not believing that I had just masturbated while sitting in a lounge full of people drinking after work. Hell, I could get myself arrested for doing that, not to mention the other kinds of trouble I could attract. I laid my magazine down, thinking I would just have one more drink before going up to my room, where I could order up dinner and stay out of trouble.
My thoughts were interrupted by a deep voice saying, “Excuse me, but you look just like a lady I used to live across the street from.”
I didn’t recognize the young man who had approached my table, so I asked him where he used to live. He named my home town, and the street I had lived on. I still didn’t recognize him, until he told me his name, which was Tim. Then it hit me.
“My God!” I said. “That was years ago, and you were only about 10 or 12. How did you ever remember me?”
He smiled. “My parents have lots of pictures of neighborhood parties, and you are in most of them. My mom always teased my dad about having a thing for you, because he took most of the pictures.”
I was thankful it was pretty dark in the lounge, because I was sure I blushed when he said that. The fact was that I’d had a very intense affair with his father for about two years. I quickly changed the subject, asking him where he lived now and what line of work he was in. I felt it would be rude not to ask him to sit down and have a drink, and he eagerly accepted my offer.
We talked for an hour and a half before ordering something to eat. I learned that he was in law school and had recently started working as a paralegal for a Midwestern law firm. He’d been sent to Chicago to research a case, and was staying at this hotel.
After we had eaten I told him I’d enjoyed visiting with him, but I had to go now and get some rest. He stood up to shake my hand, then asked if I would have dinner with him the next night. I said that would be nice, and we arranged to meet at six o’clock in the hotel lobby.
In my room I quickly got ready for bed. I slipped naked between the sheets, and my right hand went straight to my damp cunt as if on autopilot. My fingers worked their magic as I thought about the hot passionate sex I had once had with Tim’s father, Glen. I remembered vividly how it had started at a neighbor’s back yard party. Glen and I had flirted before, but this night he became very graphic and told me that his cock got hard every time he was around me.
I tried to laugh it off, but he said, “Just look what you do to me.” With that he moved the towel he’d had across his lap, exposing the swollen purple head of his cock poking out of the top of his shorts.
Well, that was all it took. I met him at a motel the next morning, where he had me naked and flat on my back in less than three minutes. I remembered how good his cock felt as he eased it slowly into my wet and ready pussy, and remembering, I came hard, drenching my hand and jolting myself back to reality, even as waves of pleasure rippled through my body. I fell asleep with a wet and steamy crotch.
I wore a short dress and black stockings for my date with Tim the next night. We had a great time, and afterwards, when he walked me up to my room, I thought it only polite to ask if he’d like to come in for a glass of wine.
As we sat talking on the sofa I kicked off my heels and curled my legs under myself, a movement which caused my skirt to ride high enough on my thighs to expose the dark bands of my stockings. I tugged it down, but it still didn’t cover much. Tim tried to avoid looking down, but his natural instinct won out, and finally he said, “You always did have beautiful legs, you know, and you still do.”
At that point I knew I could have him if I wanted him, and I couldn’t help wondering if he was as well hung as his father had been. But I was old enough to have been his mother, and I pushed such thoughts away. I got to my feet and told him I had some work to do before going to bed, so he really had to leave. For a moment he looked like he was going to protest, but he didn’t.
As soon as I went to bed my faithful right hand again found its way between my legs. Not surprisingly, my thoughts quickly turned to Tim, and I again recalled how it had been with his father. I was teetering on the edge of orgasm when my phone rang. Thinking it might be my husband, I picked it up, although my breath was still coming in rapid gasps, and I was very surprised to hear Tim voice. “Hi, beautiful,” he said. “I can’t stop thinking about your legs, and trying to imagine what a pretty sight must lie between them. I’m lying in bed right now, stroking my cock, imagining that it’s buried to my balls in your sweet pussy.”
I found my composure with difficulty. “My God, Tim, are you drunk or what?” I demanded. “Are you crazy? What makes you think you can talk to me like that?”
Tim’s voice didn’t falter. “You were masturbating too just now, weren’t you?” he asked. “You don’t have to answer, I can tell by the way you’re breathing. Would you like me to come back up to your room so we can watch each other jerk off? I mean, we wouldn’t have to fuck if you don’t want to, but I could watch you when you come, and you could see the semen spurting out of my cock.”
I couldn’t believe it, but I couldn’t deny that he was getting to me. I hesitated for a long moment, and then heard myself telling him to come up.
I thought of not answering the light knock on my door a few minutes later, but of course I did. Tim entered quickly, saying, “Damn, I’ve never been so excited in my life!” He went straight to the bed, stripping off his shirt on the way, then turned to face me as he pushed his pants down and kicked them away. His cock stood fully erect, with precome glistening on the purple glans, and I could see it throbbing with every beat of his heart.
Nothing excites me more than seeing how hard and demanding a young man’s cock can get, and I knew now that this was going to be more than mutual masturbation. “God, Tim, your cock is beautiful,” I told him. “And if you are really interested in being with a woman your mother’s age, here I am.”
With that I let my robe slip off my shoulders and drop to the floor, and we stood facing one another in the soft lamplight.
“Christ, you are a vision!” Tim breathed. “You are one of nature’s wonders, and I don’t think there’s a man alive who wouldn’t want to make love to you.” He slipped into my bed then, extending his hand to me. I moved into his arms and we kissed passionately. Almost automatically we assumed the good old missionary position, and his cock slid smoothly into my slippery snatch.
As with most first-time acts of intercourse, our merger was feverish and lustful; we weren’t making love, we were just plain fucking. Tim had amazing control, banging my cunt like a drum for at least three minutes and bringing me to a gut-wrenching orgasm. My convulsing pussy was more than he could stand, and his warm soothing come blasted into my cunt, filling it with millions of lively sperm.
He collapsed on top of me then, with his half-hard cock still in my creamy cunt as he gasp for breath. “You’re one hell of a stud, young man,” I panted. “My God, that was a good fuck! I love your cock, it gets so big and unbelievably hard. Did you like my pussy?”
“Oh Jesus!” he replied. “I’ve wanted that pussy ever since I was old enough to get a hard-on. To tell you the truth, I ‘d love to eat it right now.”
“Why don’t we eat each other?” I said. “I’d like to suck your cock and drink your come, but I also want you to fuck me again. Will you be able to do it again if I blow you?”
“Hell yes!” was his answer. “I want to fuck you all night long!”
He’d obviously eaten pussy before, because he was a master muff diver, his delightful tongue bringing me to half a dozen pleasurable orgasms while I gave him a slow, sensuous blowjob, building him up and holding him right at the point of blowing his wad, until it just simply burst from his loins. I had him deep in my throat when he came, and I kept him there, letting his come blast straight down my gullet.
It was only a matter of minutes before he was again climbing between my widely spread legs to thrust his sturdy hard-on up my cunt and fuck me senseless. And he did indeed do his best to fuck me all night long, waking me again and again before morning to mount me and screw my ever-ready pussy.
I woke up when the alarm went off at six to discover that he was fucking me yet again, this time spoon-style. I pushed my ass back to give him deeper penetration, loving the feel of his eager cock in my snatch. We couldn’t get enough of each other, and I was an hour late for my first appointment, but I didn’t care.
The next few days were like a honeymoon, and we fucked every chance we got, even meeting at lunchtime to pound one off before going back to work. I left Chicago with a tender pussy, but with the promise that Tim would be in Los Angeles when I was scheduled to go there in a month. Not only that, but he said he might bring his father along on the trip as well. Now that should be interesting!
—Name and address withheld