When my daughter told me her son’s best friend had made sexual advances I was appalled, not least because she said she had almost accepted! When I asked why she even considered the offer, Sara said breathlessly that the young man is “really well-endowed.” I asked how she knew, and she wouldn’t say. She said before they went too far, they were interrupted by a phone call and hadn’t had a chance since.
I couldn’t get this out of my head. I may be 55, but I am not dead! Several weeks later, I ran into the fellow in question at the supermarket. He offered to follow me home and help carry my groceries. I accepted on condition that he let me offer him a home-cooked dinner. He accepted with pleasure.
Everything was perfectly normal through the meal. Afterward, while we drank our coffee, I asked about his proposition to my happily married daughter, his best friend’s mother. At once smiling and blushing, he said, “Are you jealous or something?”
The phone call from Lester came as a real surprise. It must have been a dozen years since we’d had contact, when I took some golf lessons with him (he was the pro at our club when we could afford to belong to one), and he’d really improved my game. He was an incredibly good-looking young fellow, and I’d been startled when he indicated that he’d like to improve more than my golf game! Hell, I was 20 years older than him! Something probably would have come of it if my SOB husband hadn’t gotten wind that something was up and “ordered” me not to see Lester again. This from a sleazebag who was nailing every bimbo he could!
Lester said he was just in town for a couple of days and wanted to see if he could get hold of me and try to talk me into having dinner with him. We must have spent an hour on the phone catching up. He mentioned he’d heard from old local contacts that I wasn’t married anymore. When I said I’d dumped that asshole, he said, “Yeah, he was kind of a douchebag.”
We agreed to have dinner, settling on a new place I’d wanted to try. (The restaurants he suggested were long gone!) As soon as I hung up, I headed to my closet to look for something to wear. Of course I was getting ahead of myself. In addition to me being 20 years older than Lester, now we were both a dozen years older than we’d been.
Although I grew up in a wealthy family, with the proverbial silver spoon in my mouth, I was stupid and disobedient, and I rebelled constantly. All it got me was a lot of trouble, which finally resulted in my parents throwing me out of the house and cutting me off without a cent.
I only had a high school diploma at that point, having dropped out of college my freshman year, so I wound up working as a waitress in a sleazy bar. The tips were good, which was probably due more to what I wore than to my waitressing talent. My “uniform” generally consisted of a short little dress with a plunging neckline, and black stockings. I looked quite sexy and slutty.
The bar was in a rough part of town, and the crowd was usually kind of rough too. Which is why I got the shock of my life a few months ago, when a tall, distinguished-looking man walked in and took a seat at the bar.
The thing was, I knew this man. It was Alistair, a wealthy friend of my parents. He was in his 50s and married, with three children. I would never have expected to see him in such a place.
“John wants to fuck me,” my wife said.
“I don’t blame him,” I said. “Who wouldn’t?”
“But he’s supposed to be your friend.”
“Lust beats friendship every time,” I said. “Don’t let anybody tell you different.”
“Would you mind if I let him?” she asked.
“I don’t know. Can I watch?”
“I’d have to ask John about that. Do you think you would enjoy it?”
“I do think so. Do you think you would?”
“Would what? Enjoy fucking him?”
“With me watching.”
My father’s former business partner sat behind his large desk as if he was still a commander in the Army. His salt-and-pepper hair made him look very distinguished, and at 55 he was still quite an attractive man. In fact, he looked even handsomer than I remembered. I hadn’t seen him in nearly three months, but when my husband left me and I became desperate, I just had to go and see him.
“Well, Janet, how are you?” he asked me. “You look just as beautiful as the last time I saw you.” With that he got up from his desk and came over to give me a hug. The hug lasted a little longer than I had expected, and I grew slightly excited. I actually felt his prick hardening against my thigh. My mouth went dry as he leaned back to take a good look at me.
As he stepped back I deftly reached behind me to lock his office door. He heard the click and looked at me quizzically. But he seemed to understand when I began to tell him how difficult things had been for me lately, since Barry had left me.
He went back to sit in his leather desk chair, but swiveled it to face me as I slowly moved around his desk and approached him.
Jobs are hard to find in this economy, so when I found a position in the city that paid twice the money I’d been making at my last job, I had to take it, even though it meant working a 4:30–11:30 P.M. shift.
It turned out that there was a commuter train that left the city at midnight and reached my town 50 minutes later. It was cheaper than driving, so I rode it home each night, taking my iPod along to help pass the time. One good thing about it was that the train wasn’t crowded at that hour, and by the time it got to my stop there was almost no one on it at all.
On my very first night on the train, I was listening to my iPod as the conductor came by to take my ticket. There was no one in my immediate area, but over the music in my ear I thought I could hear faint laughter coming from the rear of the car.
When the train was almost at my stop I got up and headed toward the rear door. Near the back of the car I saw a blonde woman of about 30 or 35, with what appeared to be a cocktail in her hand, sitting on the lap of a bald-headed man, laughing and kissing him drunkenly. The guy was probably in his 50s, and he had her skirt around her waist and his hand between her legs.
It was a warm, starlit summer evening when I met my boyfriend Jody, and we headed for our favorite restaurant in his black Mustang convertible. Our conversation was light, and it was just nice to be together.
When we got to the restaurant our table wasn’t ready, so we waited in the lounge. After our second drink, I reached over and lightly touched Jody’s thigh with my hand. Jody smiled and replied by placing his hand high on my upper leg. He had a mischievous look in his eye. His touch always makes me hot, especially after a few drinks, and this time was no exception. I just love that squirmy feeling when my wetness just starts to flow.
Now our conversation took a new path. Feeling all warm and sensual, I said to Jody that we needed to have an adventure that evening, and that I was game for just about anything.
“Like what?” he asked, smiling. I thought long and hard, and finally came up with the suggestion that we go to a strip club. My excitement rose as I thought about Jody watching me with the strippers. Having private dances, where I could kiss them as I played with their delicious tits and felt the softness of their pussies as Jody watched. He might even be able to see me and a stripper finger-fuck each other. Oh my God, I was getting so hot and so wet!
I was quite surprised to find my friend Joyce sitting on our front step when I got home one Monday evening. She followed my car into the garage, where we hugged each other before she started apologizing for coming unexpectedly. I hugged her again, telling her she was welcome in our house anytime, and it was always good to see her.
I helped her get her bags in before we settled down on the patio with a couple of drinks to catch up. She told me she and her husband Jim had had a serious disagreement the day before, over the fact that she had gotten a big promotion on her job. He thought she must have earned it on her back, because he was very jealous of her boss, who was a handsome but very married man and had in fact never said or done anything out of line. Joyce had already scheduled a couple of weeks vacation time, so she’d just packed her bags and driven to our house unannounced. I asked if Jim knew where she was, and she told me no, but she would call him in a day or two.
I called my husband Roy, telling him we had company and asking him to pick up a pizza on his way home. Roy really liked Joyce, and often found it hard to avoid staring at her, since she is a very pretty blonde with a great body. I knew that he would love to jump her bones, though he claimed not to want any other woman but me.
My husband was out of town on business, so I suppose I should have been expecting it.
It must have been about two in the morning when I was rudely awakened from a deep sleep by a hand covering my mouth. Although I tried to scream, no sound escaped around the gloved hand, which was quickly replaced by some sort of gag. After the first instant of terror I realized what was happening and tried to relax, but my heart continued to pound. As often as it happened, I never really got used to this sudden disruption of my slumber.
The intruder quickly had my hands pinioned over my head with what felt like handcuffs, which he fastened to the headboard of my bed. I began to struggle wildly and to kick my legs, which I knew would please him. One at a time, he tied my legs to the foot posts of my bed.
Realizing how helpless I was, calm spread through me, and any lingering fear disappeared. Is that you, Reggie? I wanted to say. Again? But the gag prevented me.
It was still dark in the bedroom, and anyway I knew he would be masked. Part of the game. Then I heard the sound of fabric being cut, and realized that he was using scissors to cut away my nightie and my panties. This left me naked and totally exposed to my night visitor.
I had to take a trip to Denver last month to consult with one of my clients, and it was on that trip that the fulfillment of a sexual fantasy that had been burning in my soul for years actually took place.
I had just boarded my plane and settled in for the lengthy flight, when to my astonishment and delight I saw Lisa seated just in front of me, across the aisle.
One of the first things I had done when, a few years earlier, I moved to the city where I now live, was to become a member of a local church and start attending its Sunday services. I am a deeply religious person, and my faith has always been extremely important to me. And it was at these Sunday morning services that I first laid eyes on this exquisite creature named Lisa.
Lisa was astounding. I’d never seen anyone quite like her before. She was a flawless woman—beautiful, classy and smart—and I felt as though she had been made only for me. She always wore these super-sexy yet fashionable outfits to church; she knew just what to wear to accentuate what she had, and what she had was heavenly. She was about five feet four and had this slender body, with long legs and a slim, tight ass. Her rather dramatic effusion of red hair was the perfect match for the striking features of her fine face. There was no other woman in the entire town, let alone in our church congregation, who came as close to looking as hot as she did.