I Had a Youthful Fling With An Older Woman

This is a story of what happened to me my first Christmas away from home.   I had just turned 19 and had just started courses at the local community college that fall. We didn't have a lot of money in my family and my parents were already working hard to make ends meet, so in order to stretch out my funds,   I got a job working at a supermarket bagging and carrying out groceries. I didn't mind; my parents were already sacrificing and this was my way of pulling my weight, doing my bit. The plus side was I could afford a better car. I'd swapped my Volkswagen beetle for a souped-up '69 Chevelle SS, so this made me happy.

This was the only thing that made me happy, however. I missed those days back in high school, where I was the big football hero. I missed Tracy, a hot little cheerleader who loved to express her hero worship by giving me long, slow, loving bl*wjobs in the front seat of my '57 Chevy. Tracy was a c*cksucking fiend, and I missed making it with her Saturday nights.

There was no shortage of beautiful young things strutting around the community college campus in their short skirts or tight jeans, walking in pairs to class with their chests way up high and firm. But for some reason the girls seemed repelled by me, and I wasn't getting any skirt action.

Even though we'd pledged eternal love to one another at the end of the school year, after Tracy had gone off to college her letters to me became less and less frequent, until at last they stopped coming altogether.

I finally accepted that Tracy had moved on; some kind of upper classman at the Ivy League school she was going to back east was making it with the hot little cheerleader I used to make it with. I was alone and miserable. I was practically crying myself to sleep at night, beating my meat to the memories of those Saturday nights with Tracy.

At the supermarket there was this one woman who used to come in and a few times I had carried her groceries to the car. Nothing out of the ordinary up to that point. She appeared to be around late thirties and wore a wedding ring.   I found out later she was 45. She was very attractive for her age, a petite brunette with an olive complexion, full, firm bre@sts and a nice @ss. Naturally I took notice; she was a welcome bit of eye-relief to help cut up the boredom and repetitiveness as I slogged through those long winter nights working at the store.

Then one evening in the middle of the week she came in and as usual I carried her groceries to the car. She thanked me. Then she squeezed my hand and from out of nowhere passed me a note.

"I am going to be alone the entire weekend and I just gave you my phone number," she whispered. "My husband is going to be out of town for a week. Give me a call this Friday evening if you are interested in the entire weekend."

I didn't know what to say. I must have looked like some kind of Neanderthal, standing there with my jaw hanging down as she got in her car and drove off. I looked at the note. All it had written on it was her number.

The more I thought about it more I thought what the heck. I had long accepted the fact that the thing with Tracy was over, and it didn't look like I was going to get involved with any of the campus chickadees anytime soon. I called the number that Friday evening. She said to meet her in the college parking lot #2 north end, at seven p.m.

I was there waiting when the lights of her car came around the bend. She got out and there was a momentary pause; it was almost as if she was thinking the thing over, or maybe sizing me up. I guess she was just as tentative about what was about to happen as I was.   "OK, before we do this, there's just one thing I want to make clear," she said, nodding her head up and down like she was agreeing to a deal. "If you can't keep a secret, get back in your car and leave. Right now." She was right upfront about it.

I assured her I could be very discreet. "Good," she said. "Grab your toothbrush." I locked my car and got in her car. Not much was while she drove, just, "What's your name?" I told her, and she told me her name was Cindy, she was 45 and that was all I needed to know.   She also told me she had been married for 20 years and this was the first time ever she had ever done anything like this, that she had never cheated on her husband. I learned very little else about her.   "I don't want to talk about my marriage," she said. We went about fifty miles down the road to another town. When we got there she checked us into a motel.

Once inside the room she turned to face me, and for the first time I could appreciate the height difference between us. I'm six-foot-three; the top of her head barely came up to my shoulders.   Cindy was wearing this classic dress suit, and a string of pearls, even; she looked like a tiny little Barbie doll looking up at me. She gave a little shrug, like she was saying 'here goes', and before either of us had even said a word she put her arms around me and we kissed.

We kissed long and slow, a true open-mouthed soul kiss. I felt her her ample bre@sts pressing against me; her b**bs were large, yet incredibly firm for an older woman. Then her hands started moving over the muscles of my upper arms, all up and down my chest, and our kiss turned into something more.   She started sucking my tongue into her mouth, making me think that if she did it the way she kissed I was in for the **** of my life. It wasn't any ordinary open-mouthed kiss; the girl sucked on my tongue like she was sucking c*ck.   When we finally broke the kiss she cooed, "Ooh, I've always wanted to try it with a guy like you." I could tell she was totally hot and h*rny.

I started to peel off my clothes but she said, "No, I want to undress you." I shrugged and stood there, held my arms over my head while she pulled my sweater off.   She was running her fingertips all over my chest; "Oh, do you work out?" she whispered. I just shrugged - I was still doing the football workout, knocking out some pushups and situps and running some miles every day, and I guess it showed.

Sitting on the edge of the bed before me, Cindy started to untuck the tank top I had on under the sweater, and that's when it came to me: it was like Christmas morning, and she was opening her presents.   She undid my belt and pulled down my jeans and my b*ner poked forward, making a tent out of my shorts, inches in front of her face.

She placed the palm of her hand right on my bulge, grabbed my hard c*ck right through my shorts. She looked up at me with the most serious and intent look in the world on her face, as she put her fingers in the waistband of my shorts and pulled them down. My d-ck sprang right out, bold and impudent and free at last in the cool air of the room.

Cindy was staring at my c*ck like she was studying it, to the point where I was almost becoming embarrassed. She was still fully dressed, after all, and there I was standing fully exposed with my pants down around my thighs.   She closed her eyes and there was a momentary pause, like she was giving herself permission or something. Then Cindy parted her lips and took my c*ck into her warm, wet mouth.

All I could do was close my eyes and groan as this beautiful, middle-aged angel worked her magic with her lovely mouth on my organ. She formed an 'O' with her finger and thumb and was stroking my c*ck into her mouth as her lips went up and down my pole.

Finally I could take it no more; I dropped my hands to her shoulders and tried to indicate that I was about to come, that she should release me.

"I always wanted to try that," was the first thing Cindy said once my c*ck was out of her mouth. This surprised the hell out of me because as far as I was concerned she sucked c*ck like a pro - she put my little cheerleader to shame.

"You mean you've never sucked . . .?" I stammered.

"No, honey, of course I've done THAT!" she laughed, "I've been married for twenty years, do you think I've never sucked a d-ck?" Still holding my c*ck in one hand, she put her hand to her face as she smiled in an embarrassed way.   "What I mean is, I've never done it while fully dressed, with a totally naked guy who's young enough to be my son, in a motel room with all the lights on!" Cindy looked back at the head my c*ck where a shining droplet of pre-c*m had formed, and the tip of her tongue darted out to lap it up. "Mmmm . . . " she said thoughtfully. Then she glanced back up at me with a mischievous look in her eye. "It's kind of kinky, don't you think?"

We ended up in the shower together. She enjoyed running her hands up and down my body, rubbing the soap all over me and making me hard again. Then she turned and I soaped her up. Her muscles of her back were firm, there was a nice line running down her back to the two little dimples right above her round @sscheeks.   I rubbed the soap up the crack of her @ss as she backed toward me, then I reached around to make her bre@sts all slippery with soapsuds as I fondled them from behind, a nice round pair of slippery handfuls.

The showerhead was spraying hot water from behind as Cindy squirmed her back up against me like a slippery little otter. I pinched her n*pples and this made her sigh, then I soaped up her flat, firm belly and moved my hands down to cup and hold her mon du Venus. I was delighted to find her p*ssy neatly trimmed, her natural hair cropped close into a narrow *****, she was shaved completely bald from her cl*t on down.

I had one arm about her full, firm bre@sts, the other fondling and diddling her cl*t. Cindy was so small she was practically like a toy in my arms; it was like playing with a sexy little doll. Cindy held onto my bicep as she melted before me; her knees were going weak and I could tell I was bringing her to org@sm as her p*ssy became hot and wet beneath my fingers.   Finally she turned and we embraced beneath the steaming hot needles of the shower. She snuggled her hot box up against my stiffening tool as we kissed long, slow and lovingly.

We went to bed and it was my turn to go down on her. "Do you like the way I trim my p*ssyhair?" she asked as my face hovered mere inches above her neatly coifed mons - the girl didn't have any kind of self-confidence issues, not at all.

"MMMMMmmmmm" was all I could reply with my mouth buried in her wet sl*t. I lifted my face to let my tongue tickle her little hard cl*tty. "I like it!"

"I read about it in Cosmo, all the girls are doing it nowadays."

I did it all to her; fingers, tongue, lips on her classic bald-as-a-billiard-ball qu*m. Cindy thrashed about on her back and moaned, until it was almost as if she couldn't take it anymore. "Please? . . ." she begged, " . . . please? . . . **** me now?"

I moved up and regarded my tiny little middle-aged lover beneath me. "Here honey," she said quietly, reaching into her handbag on the bedside stand. She pulled out a cond*m. "Let me put this on you."   I sat back on my heels with my raging b*ner poking straight up in the air while Cindy scooted up a bit so she could tear open the foil packet. Her fingertips felt terrific as she placed the rubber on the head of my c*ck and unrolled it onto my shaft.   Then she wiggled into place, her beautiful thighs wide apart, and reached down to part her l@bia guiding me in with two fingers. Her little tw@t was small and tight around my c*ck like a little clam; I could feel her hot wetness right through the rubber.

Cindy was c*mming on my pole from the minute I stuck it into her. I held on to her @sscheeks, gripping tight, as she thrashed beneath me like a landed trout. My face was in the pillows next to her head, muffling my roars as I came, filling the rubber with j*zz. I came so hard some even leaked out the top.

Then we just lay there, connected still; it was like I was dead on top of her. Finally I lifted myself; Cindy regarded me, her hands were on my upper arms. Then I had to reach down to make sure the cond*m stayed on as I withdrew. I pulled the thing off and we both marveled at the amount of c*m in it; I must have spurted gallons.   Then I did a run to the bathroom, and when I got back she got up and it was her turn in the bathroom.

We fell asleep in each other's arms; that was it for the first night. I woke up hard and h*rny, and I woke her up with my b*ner prodding her @ss. She turned around, opened her legs so she could lay there for a while with my hard meat on her inner thigh. Then she said, "I've got to go brush my teeth," and she got up went to the bathroom.

Then I went in because I couldn't hold my pee anymore. While I was taking a p*ss Cindy poked her head in the door and watched me urinating. I glanced up and she was smiling wide, her eyes all bright and twinkling as she watched me p*ss, standing there naked with my d*ck in my hand. I brushed my teeth and returned to find her with the sheets up to her chin and smiling at me. I could see her n*pples poking through the bed sheet.

I climbed on top of the sheet, trapping her. We kissed while she squirmed beneath the sheet, rubbing her hot box up against my hard c*ck, trying to part her legs. When I'd finally tormented her to a state of total h*rniness I moved over to the side and ripped the sheet away and we made love right on top of the mattress, the bright light of the morning flooding the room. Cindy was looking down to watch as my hot steel rod drilled her p*ssy to the mattress.

After we got cleaned up, it was obvious we'd have to go out, leave the confines of our sanctuary, to get something to eat and to give housekeeping time to do up the room. We found a nice restaurant downtown in the business district and had a sumptuous feast; f*cking like minks had built up an appetite, apparently.

She'd said she didn't want to talk about her marriage, but two people have got to talk, right? So she talked about it, rather, she talked about why she was doing it, why she'd passed me that note in the parking lot in the first place. "An opportunity like this comes up only once in a person's lifetime, right? And it's Christmas, so I thought this year I'd give myself a Christmas present."   She paused for a moment, took a sip of coffee, looked out the large plate glass window at the goings on in the street outside, then she looked back at me. "You just lucked out," she shrugged. And then she smiled, "Merry Christmas!"

To kill a little more time we wandered around the shopping district. The streets were full of holiday shoppers. We window-shopped in front of the old-fashioned department store, then we wandered inside.

I imagine to anybody paying close enough attention it might have been obvious what was going on; a smartly-dressed business woman in the company of a much younger guy in jeans and a leather bomber jacket.   I suppose we might have been taken for a mother and son, out shopping for the holidays. We didn't care what anybody thought; there was this otherworldly feel to what was going on. Nobody knew who we were and we would never see any of these people again.

Cindy selected a few items, held up a few shirts to see what they'd look like on me, but I didn't want her to buy me anything. She ended up purchasing a nice dress shirt for me anyway, something that I could get away with wearing with my jeans, though.   Then somehow we ended up in the ladies lingerie department. Cindy took a skimpy black lace bra-and-panty combo off a rack and turned to me, holding the scanty garments against her body with a naughty smile all over her face. I indicated a garter belt, and Cindy scooped up that item, and a pair of stockings as well, thigh-high's, the kind with the line going up the back of the legs.

It was time to make our way back to the motel room.

I put on the new shirt, because Cindy obviously had a thing about undressing me. It was a nice shirt; long sleeve, button-down collar, blue Oxford strips, a classic Brooks Brothers number.   I was standing in front of the mirror doing up the buttons and practically threw my neck out of joint when Cindy came out of the bathroom in her stockings-and-heels lingerie outfit. The bra and panties were made out of this sheer, see-thru material; they just accentuated her naked body, they didn't cover her in any way, and this was so s*xy in such a beautifully naughty way. With her string of pearls she looked like a thousand-dollar-a-night h**ker.

She sidled up to me, put her hands all over my chest, all over the new shirt as she pressed her **** up against me. Looking down, the view of her generous bre@sts pressing against the sheer material of her skimpy bra was making me hard.   "Oooh," she cooed, "You look so handsome in that shirt, mister." She was acting the wh*re part, living the moment. I could feel her heat as she rubbed her hot, panty-clad p*ssy up against my thigh. "Mmmm, I like it," she murmured as she began undoing the buttons.

Cindy undressed me, led me to the bed, then she went down on me. I was in total heaven, kicked back with my hands folded behind my head as I enjoyed the spectacle of this glamorous vixen slurping on my c*ck, done up to the nines in her fabulous underwear, stockings and heels.

Making love to this beautiful woman in exotic lingerie was a wet dream come true. I loved the look of her thighs coming out of the tops of those sheer black stockings, the way her little string-sided panties accentuated her round hips.   I kissed Cindy's p*ssy through those barely-there panties, nibbled and kissed her hard little cl*t until the sheer fabric of her panties was absolutely saturated. Then I pulled them off and tossed them aside and gave her wet p*ssy the tongue ride of her life.   When we did it she wrapped those stocking-clad legs around mine and hung on for dear life. I sank my fingers into her soft, round @sscheeks and when I came I roared like a lion.

I don't think I have ever met any woman who enjoyed it as much as Cindy did. She was a total nympho; she couldn't seem to get enough of my c*ck. She literally s*cked me and f*cked me sixty ways to Sunday.   "I want to do it all, Sean," she explained. "I want to make up for twenty years of being good, I want to have something to remember when I get old."   We did sixty-nine, she even let me c*m in her mouth; in fact I was beginning to worry if I could even keep up with her. We spent the entire weekend in bed except for when we went out to get something to eat.

Early Sunday evening we drove back. Pulling into the college parking lot, Cindy turned to me and said, "I want to thank you for a wonderful weekend." Then she added, "Merry Christmas, Sean," and we kissed like we did the first time; long, slow and lovingly.

I got out of the car and Cindy drove off, and that was the last I saw of Cindy, the rest of that winter. She stopped coming to the store where I worked. The holidays came and went but something definitely missing; not seeing Cindy, or even knowing where she was. . .

. . . Sturmbringener sends . . .
sturmbringener sturmbringener
46-50, M
3 Responses Jun 6, 2007

Great story, that was a very lucky encounter!

Great story! class act...pity about the....rubber......it always....s'ucks!

Ditto with the WOW!!!!!