One of the positive benefits of getting a divorce after nearly twenty years of marriage was my newfound freedom. I had always wanted to move to the city but my wife was a die-hard country girl. During our marriage we compromised by living in the suburbs. Now that I was single again I had the chance to move back to the city where I could take advantage of the seemingly unlimited singles bars and endless numbers of available women. My one daughter remained with my ex, so it was no problem for me to move into a one-bedroom bachelor pad I easily found. I was in my element, again. I loved every second.
Since I was a very fit, athletic 45-year-old, I had no trouble meeting and dating younger women. This made me feel more alive than I had been used to after years in a boring marriage. My experience and contacts in the business world made it easy for me to land a decent managerial position in a promising young start up company. The owner was an associate of an old friend of mine and I was told nothing but good could come of me taking this job. Everything seemed perfect and my life was right on track.
The job entailed working long hours at first. It was in an industry that I was unfamiliar with, though the work itself was for the most part second nature. My boss was the biggest workaholic I had ever met. John seemingly never left the office. This company was his baby and he was utterly determined to make it work whatever it took. I was the one who felt the need to balance work and play, a need he didn’t seem to have. So, it was a bit of a surprise when one day he suggested we get together for a night on the town. My new girlfriend Joyce, myself, and John and his wife. I had never even imagined he had time for a wife. John was the type of guy who never even took the time for a proper lunch, preferring to run around the office with a sandwich hanging out of his mouth. John suggested we all meet that evening at a local bar for a few drinks then head on over to a cozy Italian restaurant he knew of. Sounded great to me. I called Joyce and she approved. I told her to dress casual and meet me at the bar at six.
John and I tied up any loose ends at the end of the day and headed over to the bar as planned. John as usual had on his jacket and tie. I can’t recall ever seeing him loosen his tie. I had on my work clothes with the sleeves rolled up on my dress shirt exposing my muscular forearms. Joyce liked touching my forearms, reminding me that those years of reverse curls were not in vain.
John and I were the first to show up at the bar. It was shortly before six. I was standing at the bar with my pint of Guinness when Joyce walked in a few minutes later.
“I see you had no trouble finding the place,” I said as she walked up.
“Oh, I’ve been here before.”
Joyce looked hot in her shirt and tight fitting blue jeans. The fit of her jeans accentuated every curve of her young butt and lovely legs. I introduced her to John. He gave me a sly nod of approval.
“Play a game of pool while we wait for John’s wife?” I asked. I really just wanted to see Joyce bending over the pool table in those tight jeans, though I did like playing the game.
We started playing and I easily took the lead though I really didn’t care. I got more of a reward watching Joyce lean over the pool table as I sipped my pint of Guinness. She casually touched my forearms after almost every shot. After a few minutes John made a remark, “Ah, look who’s here.”
Without turning around I had to assume John’s wife showed up. Not exactly expecting much, I turned around and almost spilled my drink down my pants. I was greeted by the most heavenly sight I had seen in some time and I had seen quite a few in my day. Standing before me was a five foot seven, blue-eyed beauty with dark red hair. She had on a T-shirt and tight skirt. Her perfectly applied lipstick matched her nails and her open toed heels. She introduced herself as Debbie. Various thoughts immediately ran through my head, none of which would have furthered my career.
“Can I play the winner?” she asked. Her question made me glad I had spent a significant portion of my misspent youth hanging out in pool halls, as I was way ahead of Joyce in this game.
“Sure,” I said, unable to say much else as I felt the blood run out of my brain and head further south. I could feel a mild bulge in my pants as my cock started to strain against my zipper.
Debbie had a level of charm and a sense of style that was too good to have come naturally. I had no doubt she practiced her moves in front of the mirror at home. She was that good. Lord knows she had the time with John away at work fourteen hours a day. I wondered what a girl this heavenly could possibly see in John. John was a decent guy but he looked like the only lifting he ever did was lifting the phone to his ear at work. Surely Debbie deserved better, I said to myself.
I had no trouble winning my game with Joyce. Debbie grabbed her cue as I began to break. I made an impressive looking break but didn’t sink a thing. I thought of something that I’d like to sink.
Debbie leaned forward to make her shot. As she bent over the pool table her shirt crept up her back, revealing the small of her back. I had a perfect view. It was heavenly. As she leaned forward I felt like rubbing my pool stick along her perfect butt. Actually, that wasn’t the only stick I wanted to slide along her butt. As she finished her shot she passed by me and casually stroked my forearm. I was smitten. I sprung a boner so quick I thought I was a teenager watching the girls’ basketball team back in junior high. I thought to myself that after two months on the job I’m finally getting a raise. But not from the boss, from the boss’s wife.
After a couple more drinks we all got into a cab and headed uptown to the restaurant. Debbie’s unrelenting charm and casual glances my way left no doubt in my mind we were each thinking the same thing. This girl was hot enough to melt the sun and had a natural sexiness that was no doubt coming to a boil after years of relative neglect being alone for so much of her day. I could only imagine how much pent up sexual energy this woman contained. My mind was racing and my crotch was throbbing. It was hard for me to resist telling the cabby to stop at the nearest hotel so Debbie and I could get off. I’d like to get off all right. My skin was crawling as the desire built up in me. I felt like a lion at feeding time.
Man, was my mind working overtime.
We finally arrived at the restaurant and we all headed in. Debbie would smile my way from time to time. She had a gorgeous grin and perfect white teeth. We all were seated in short order at a cozy table for four. I sat across from Debbie. Joyce was to my left; John was seated to my right.
The waiter introduced himself as he brought over our menus. We ordered a bottle of red wine and continued our conversation. John was especially talkative. He probably had not been in a social situation in some time. Joyce was relatively quiet and Debbie continued to be her hot, sexy, playful self.
After a couple of glasses of very nice dry red wine, I could contain my urges no more. Debbie’s sly glances my way as she played with her auburn tresses made it clear in my mind that she wanted me to make a move. I really felt like knocking the wineglasses off the table and taking Debbie right there, while her husband and Joyce watched. What was the worst that could happen, I thought? I could always move out of town and get a paper route or something, worse comes to worse. I knew what to do. I casually slipped my left foot out of my boat shoe and slipped my foot under Debbie’s skirt. She was directly across from me so it was no problem. She gave a startled look at first followed by a big grin. I worked my big toe along her thigh up to her crotch. I started to toe fuck her very gently at first, sliding my sock-covered toe up and down her ever wetter slit. I could see by her expression that she was thoroughly enjoying every minute. Getting toe fucked under the table while her husband went on about the price of crude oil in South America or something. I gently massaged her clit with my big toe while my other toes teased her womanhood. I could feel the moisture permeating my sock. After a few minutes I pulled back. I felt like reaching down and touching my toes and running my fingers under my nose. I wanted to smell this woman’s scent so bad. But I hesitated.
In a few moments Debbie excused herself and got up to leave the table. I started to think if I should follow her but John started talking to me about something and I hesitated. John’s words went in one ear and out the other. I could see his lips move but my mind was a million miles away. I looked at John with his thinning hair and skinny arms and thought, what a lucky bastard. If I had a wife like his I would be home every night at five bearing gifts as she greeted me with open arms, and legs.
Just as I started to think about getting up, for about the tenth time in the last five minutes, Debbie walked back. She seated herself with an extra-devilish grin on her face. I tried not to stare at her though I wanted to so bad. In a moment I felt something on my lap. I glanced down thinking that maybe my napkin had fallen off my lap. It was Debbie’s panties. She had gone to the bathroom to remove them and now she had tossed them under the table and on to my lap. I carefully unfolded them. I noticed she had kissed them just above the wet spot. I tried not to be obvious as I carefully concealed them in my napkin. Oh, I wanted to reach down and sniff them right away. But, I had to be careful. I did have a lot to lose, but oh so much to gain.
I carefully and as unobtrusively as possible raised the napkin containing the panties to my face. I opened it just enough so that Debbie could see me sniff the panties and no one else. I quickly wiped the panties under my nose and kissed the lipstick spot on the white panties before lowering the napkin back onto my lap. Debbie had an ear-to-ear grin on her face that would have been enough to give me a rock solid hard-on if I didn’t already have one.
After more wine, dinner and Debbie just looking so damn scorching hot, once again I had to do something. I excused myself from the table and walked out into the lobby. Either Debbie follows me out or I would have to take matters into my own hands. I felt like a rabbit on Viagra after an oyster dinner. Sure enough Debbie showed up about two minutes later. I grabbed her hand and led her out the door without saying a word. We ducked into an alley about two doors down as I quickly undid my belt and dropped my pants. My throbbing cock sprang to life. It had been waiting for this moment the last two hours. Debbie bent over and took it all in her mouth like a pro. As she applied her tongue to the sensitive underside just below the head, I almost came immediately. She grabbed my shaft and started stroking me up and down. When she sensed I was about to shoot my load, she immediately stopped stroking and pulled down, tightening the foreskin around the head. She removed her mouth and tilted her head back, allowing me to shoot my warm cream all over her face and into her lovely auburn hair. I was in ecstasy. I took my fingers and wiped the cum off her pretty face. She licked my fingers one by one in a slow, deliberate manner that by itself would have caused me to cum if I hadn’t just shot my load a minute before.
“Let me clean up your hair,” I said as I removed her panties from my right pants pocket. I noticed the lipstick marks on my cock matched the lipstick on the panties. I got what I could out of her hair with her panties then put them back in my pocket.
“We should go back in. I’ll go in first. I’ll say I saw you on the phone if anyone asks,” I told her. I added, “By the way, I think it best if this is it. We both have way too much at stake.”
She nodded in agreement as I pulled up my pants and headed back in the restaurant. When I got to the table John was still ranting about the price of soybeans in Lithuania or something as Joyce pretended to be interested.
“Did you see my wife?” John asked after I sat down.
“I saw her just outside the door. I believe she was on the phone,” I answered.
Debbie came back a few minutes later.
“My sister says hello,” she said as she looked at John. ‘Wow, she has a sister,’ I thought to myself.
A couple of days later I was sitting at my desk. It was late afternoon and the phone rang. I picked it up and a familiar voice was on the other end.
“Hello there,” the voice said.
“Do you want me to get John?” I asked.
“No, I need you.”
An hour later I was heading out the door. As I was rolling up my sleeves John asked, “Big night tonight?”
“Ah, something like that,” I answered. I walked out the door with a sly grin on my face.
04-27-09.
Published
 – Sex Stories){kind=link}