Old Acquaintances

I always hated shopping for clothes. I always seemed to come back with something I didn’t want. Perhaps this was because I went about it as fast as I could, which was a direct result of hating shopping so much. But here I was in a men’s clothing store looking through a rack of pants for my size, which they rarely had – another reason I hated shopping.

On the other side of the rack, at the smaller sizes, was a middle-aged woman. I glanced up at her when I couldn’t find my size. There was something familiar about her. She looked up and our eyes met.

“Tina?” I said in surprise, recognising her now.

“Yes…?” she said hesitantly, “Do I know you?”

“It’s Jake, the neighbours’ kid.”

She stared at me briefly, thinking back to our old neighbourhood, trying to place me. “Jake!” she then exclaimed, “My, I must have not seen you in ten years.”

“Thereabouts,” I said.

“Looking for clothes for Dan Sr.?” I asked, referring to her husband, some twenty years older than she was.

She didn’t reply for a few seconds. “No…” she then said, “No, Dan died a few years ago, this is for Leon.”

“Oh, I’m terribly sorry,” I said.

She shrugged, “It�s ok, we all knew he would die before me. And he never was very healthy I suppose. Lung cancer, in the end.”

Leon was her youngest son, some ten, twelve years younger than his brother Dan Jr. and his sister Maggie. He’d be almost twenty now – a weird thought, because I had visited the family when he was just born. I realised how long I’d known this woman and her family, and how long I hadn’t seen her. “You want to go get some coffee or something, catch up a little?”

“Sure,” she replied, “I’d like that.”

Ten minutes later we had found a coffee bar somewhere in the mall and had our orders in front of us. “How are the kids doing?” I asked, not knowing well what else to ask her. “They’re well,” she said. Danny was working abroad, doing something important that his poor old mother, as she said, couldn’t understand; Maggie had, to my surprise, become an architect, and Leon was still living at home, going to a nearby college.

Tina asked about my life, I told her what I’d been doing these last ten years. That I was in a relationship, although we were having some issues these days. That I had a good, steady job, a nice house. Sitting opposite this woman made a lot of old feelings come back. I remembered when I was a teenager, I had a huge crush on her. She was the biggest star of my sexual fantasies during that time.

“I carried a torch for you for years,” I suddenly heard myself saying.

“Really? For years?”

“Oh yeah, ten years or so.”

“I always figured you had a crush on me at some point, but I never suspected it was so long,” Tina said with a hint of surprise in her voice. I took a sip from my coffee.

“Why?” she then suddenly asked. The question surprised me.

“Why did I have a crush on you, you mean?”

“Yeah.”

I shrugged, “Why do people ever have a crush on anyone. You’re a nice person, and I thought you were really beautiful. Well, you still are.”

Tina blushed, “Really? You think I�m good looking?”

“Yeah, absolutely,” I assured her, “And I don’t just mean ‘good looking for your age’ or something, I mean you’re an attractive woman. But, you know, I might be a little biased.”

I don’t know what possessed me to say all this but I heard myself doing it. I figured maybe meeting Tina brought back all the memories of the rather intense feelings I had had for her and now I was finally sharing them with someone. But the person I had the feelings for might not be the best one to share them with, it occurred to me.

It might have been weird for Tina to sit there with someone she’d known when he was only a boy who now outright told her he found her attractive, and had found her attractive since being that boy. But I suppose she was simply flattered by me complimenting her, because she didn’t seem to be upset or in any way negatively affected by what I said. Instead, she asked, “You don’t mind that I’m… overweight?” I looked at her in surprise, “Of course not. In fact, it’s one of the things I find attractive in you.”

She had been overweight for as long as I had known her. I knew that she’d dieted at several points in time but it never seemed to do much. She was a heavy woman, I’d never describe her as fat although I suspect some people might. I would sooner call her ‘well-filled’ or ‘plump’, both of which sound much nicer and carry – at least in my mind – a slightly different meaning. And I did find it attractive in her. She combined heavy thighs with a full, rounded ass, a potbelly, ample bosom and a surprisingly delicate face, framed by short, dark curls. I had loved all of those things on her and had often imagined myself being smothered between her thighs or in her breasts, squeezing her ass or kissing that bulging belly.

She bit her lip, “So you think I’m still attractive?”

“Yes,” I said, “I do.” “Do you still have a crush on me?”

I shook my head, “Nah, don’t worry. They say absence makes the heart grow fonder but they also say out of sight, out of mind. I guess when you don’t see someone for years it wears off. And it was a teenage crush. Took a while to get over it though.”

Tina nodded, I don’t know if she was relieved or disappointed.

“What did you find most attractive about me?” she then continued.

I couldn’t help but laugh, I was amused by the direction the conversation was going in. But I didn’t mind it was going in this direction, I felt surprisingly at easy with it. Then again, that always had been one of the things I liked about Tina, how comfortable she’d make me feel.

“Where to start?” I replied, “I mean, I used to be mad about you, so I found everything attractive – your face, your laugh and your smile, your kindness, and of course your… physique. And they haven’t seemed to change all that much in the last ten years. Not for the worse anyway.”

She blushed, which was interesting to see. She grabbed her cup of coffee and started sliding it across the table a little.

“So… did you jerk off thinking about me?” she then asked with a soft voice. A question I had more or less expected.

“Oh yeah,” I replied, “I most certainly did.”

“What do you mean ‘most certainly’?”

I smiled and said nothing for a few moments.

“Am I making you uncomfortable?” she asked.

I shook my head, “No, not at all. We’re both adults, and sex is a normal part of life. But I get the impression I might be making you uncomfortable.”

“Maybe a little bit,” she said.

“Maybe you could stop asking questions then,” I teased with a grin on my face. A shy smile slid across her face.

She was silent for a few moments, but then she repeated her question: “But really, what did you mean?”

“I meant I used to jerk off a lot thinking about you.”

“During all those ten years?”

“Not at first,” I said, “because I only started masturbating when I was 13 or 14. But yeah, ever since.”

“Wow,” she said, “I didn’t really know about that.”

I laughed, “You weren’t supposed to know.”

Tina smiled back, “True. I just meant, I figured you had a crush but I never knew you thought of me… like that.”

I shrugged, “Kinda comes with the territory doesn’t it?”

“So how often did you do it?” She asked.

I shrugged again, “Two, three times a day? Sometimes more I think.”

“Wow. That is… that’s quite a lot isn’t it? And how often did you think of me?”

“Pretty much all the time.” I thought I saw a glint in her eyes but she didn’t say anything. “I think I thought about you like ninety percent of the time for the first few years that I masturbated,” I continued, “You were my favourite fantasy for years. Probably still are my favourite fantasy of all time, in terms of how often I’ve thought of you.” There was definitely a glint in her eye now.

“So you want some more coffee?” I asked, partly to change the subject, partly just because I felt like another coffee. Tina looked at her empty cup.

“Yeah, sure.”

I signalled a waitress and asked for two more coffees. “Want anything with that?” she asked. I ordered apple pie with whipped cream. The waitress looked questioning at Tina, Tina glanced at me. “I’ll have the same,” she then said.

The waitress left the table. I looked with a smile on my face at Tina. “Not on a diet?” I asked.

She smiled back and shook her head, “Maybe I don’t need to be on a diet.” We both knew what had caused her to take the pie.

Tina first took a sip of her coffee when the waitress had brought our order, then started eating. I looked at her as she cut off a piece with her fork and put it in her mouth, chewing slowly. Then she took some whipped cream. To my own surprise I felt something stirring in my pants when she slowly slipped the white cream in between her lips – the conversation we’d just been having hadn’t done anything to me, but this was all of a sudden strangely erotic. I swallowed hard, then took a sip from my own coffee.

“So let me ask you something now,” I said when I put my cup down. Tina looked at me, waiting. I hesitated for a moment but then I figured that Tina had asked me some very personal questions so I figured it should be alright, and asked, “If I’d told you this when I was like 16 or something, that I wanted to sleep with you, would you have?”

Tina didn’t say anything; I felt nervous, despite there being nothing on the line, it was a hypothetical situation.

“Well I wasn’t a widow back then, of course…” she then said, “But it wasn’t like Dan and I were having much sex at the time. And I have to say, I am very flattered by the thought you were thinking about me so often. I guess I might have, yeah.”

“Makes me wish I had said something, then,” I said.

We sat in silence for a while, lost in thoughts of our own and finishing our pie and coffee. “You could still say it,” Tina then suddenly said.

“What?”

“That you want to sleep with me,” she explained.

I looked at her in surprise and saw that she was serious. “Wow…” I managed to say, “that’s uhm… that’s very interesting. But I have a girlfriend. And, well, I’m not really in love with you anymore, I mean, it was just a crush back then.”

“But you think I’m attractive,” said Tina.

“I do,” I replied, “of course I do, but that’s another matter.”

“Are you hard right now?” she then asked.

I looked down, as if to verify what I already knew, and nodded.

“So something of that torch you carried might remain,” Tina concluded.

I shrugged, “Of course. But I still have a girlfriend.”

“That you’re having trouble with,” Tina countered.

“You didn’t have a girlfriend when you were 16,” she then said, “did you?”

I shook my head.

“So what if we pretended you’re 16 and I’m 38 again.”

“And you’d be cheating on your husband?” I asked.

“Well like I said, we weren’t having much sex back then. And it’s not every day that you get the chance to have sex with a horny teenager,” Tina replied.

I smiled, tempted by the prospect of this little role play she had started. “When I was 16 I was still too shy to talk to you about this,” I countered.

Tina got up from her chair and sat down next to me on the bench, “But what would you say if I asked you if you were in love with me?” she said in a husky voice.

“I’d mumble nervously,” I said, finding myself getting into character.

“You see Jake,” she continued in the same voice, “my husband is neglecting me and I need a young man like you to take care of my needs. Someone who jerks off several times a day thinking of me. Do you ever do that, Jake? Do you jerk off thinking about me?”

I was really beginning to feel like I was 16 and madly in love with her again, so tempting was the presence of her body, her voice that had dropped to nearly a whisper.

I tried to look embarrassed as I said that yes, I did. She then placed her hand on my groin and my erection grew even harder. She leaned over and whispered into my ear, “Would you want to make those fantasies a reality?”

At that moment I forgot about my girlfriend and could only remember the crush I had had on this woman for such a long time, and the countless times she had starred in my fantasies. “Y-yes,” I stammered.

She squeezed my cock through my pants, “Maybe we should go someplace else then,” she whispered and got up.

I got up as well, ready to follow her.

“Your place or mine?”

“I didn’t have a place when I was 16,” I replied with a smile.

Tina smiled back, “My place then, I guess.”

We left the caf� and walked to Tina’s car.

“How far is it?” I asked.

“About ten minutes or so,” she replied and unlocked the car.

We got in and Tina took off. “Any of your kids home?” I asked.

She briefly glanced at me, then replied in character, “No, they’re still in school. Shouldn’t you be, as well?”

I shook my head, playing along, “Teacher got sick, we got the afternoon off,” I replied.

“I have the afternoon off as well,” Tina said, “maybe we could hang out together or something. Unless you don’t want to hang out with an old woman like me.”

“You’re not old,” I said, “And even if you were, I still wouldn’t mind hanging out with you.”

“Really?” Tina asked and turned into a parking lot, “You don’t think it’d be boring to hang out with the mother of your friend?”

I shook my head as Tina brought the car to a halt, “Nah, I think you’re pretty cool.”

“‘Cool’ like you would find a friend of yours cool, or ‘cool’ like you’d find a girl cool?”

“Mostly like how I’d find a girl cool.”

She turned off the ignition and took out the keys. “So would you say you’re attracted to me? I’m old enough to be your mother.”

“I know, but still… I think you are very attractive.”

We were both doing our best to play our roles, me the shy 16 year old, she the 38 year old married woman being told by a teenager that he found her attractive. I guess it wasn’t very realistic, but it was still convincing enough for us. “Would you like to come in and show me how attractive you think I am?” Tina whispered.

“I would love to,” I said, and with that we both got out of the car, and I followed her to her house. I saw her fingers were trembling as she tried to put the key in the lock. She opened the door and let me in, then came in after me. I turned around and before the door was fully closed we were engaged in a kiss that lasted about a minute. My hands roamed her full body, from her shoulders down to her round hips.

She broke the kiss and took my hand. “Bedroom?” she asked. I nodded. She led me up the stairs and into her bedroom, a light room where a large bed awaited our love-making. I lay down on the bed, she lay down on top of me and we kissed some more, my hands again exploring her luscious body.

Tina started tugging at my shirt and I quickly took it off. She ran her fingernails over my skin. “You have a real nice body,” she said, then kissed my chest.

Meanwhile she was taking off her own shirt, revealing her ample, bra-clad bosom. She dangled her breasts in front of my face, I kissed the tops of them as I reached back to unhook her bra. I fumbled a little, not knowing myself if I was playing my part as a horny teenager, or just genuinely nervous. But I finally got it undone and Tina slipped her bra off.

Her breasts were now hanging in front of me, uncovered, and I took one of her nipples into my mouth. I bit softly, eliciting a small cry from Tina. I let go and asked if I’d hurt her. “No baby, you’re doing fine, that was a good noise,” she said, and pushed my head back onto her tit.

I licked and suckled, she moaned louder and louder. Suddenly she got off the bed. She slid her panties down to unveil her hairy snatch. “I’m sorry,” she said apologetically, “I’ve not really been trimming much lately…”

“No,” I said, “it’s fine, I always imagined it like this.” I got off the bed as well and dropped to my knees before her. “Just makes it more realistic,” I added, then leaned forward to taste her pussy for the first time.

Tina sighed as I placed my mouth of her vulva. She moaned when I sucked her clit, trembled when I stuck my tongue out to lick her wet labia. I licked her pussy up and down, flicking her clitoris with my tongue, kissing the insides of her heavy thighs every once in a while. I thought I was going crazy. The taste and scent of her snatch was unlike that of any woman I’d ever been with and the fact that this was the pussy of the woman who had dominated my fantasies only added to my excitement.

When I had brought her to the edge of orgasm she suddenly pulled my head back. “I want you inside me,” she said. I got up and took my pants off, then quickly slipped my underwear off as well. My erection stood proudly upwards, a slight curve in it, bouncing lightly up and down with every beat of my heart. “Oh my goodness, it’s beautiful,” Tina said breathlessly. She got back onto the bed and spread her legs before me. For a moment I had to resist the urge to lick her pink folds again, then I moved into position.

The head of my cock rested against her slit. I looked her in the eye as she grabbed my rigid member and rubbed it along her pussy a few times, coating the head in her effluent juices. Then she placed it at her entrance and gave a slight nod. I slowly pushed in, entering the woman I had spent so many hours fantasising about. She moaned loudly as my seven inches made their way into her eager womanhood.

When I bottomed out inside her, with our bellies mashed together, I looked into her eyes again. She smiled and reached up to kiss me. She then placed her hands on my ass and flexed her Kegel muscles a few times, squeezing my cock until I nearly exploded. She smiled again and nodded, giving me the signal to start fucking her.

I began slow, wanting to last as long as I could inside her, although I felt that wouldn’t be very long anyway. Her pussy was stretched around my erection, clinging to me every time I pulled back, welcoming me every time I pushed in again. I couldn’t keep up this slow pace for long. Encouraged by Tina’s moans and my own burning desire I picked up the pace, slamming my belly against hers every time I moved in, my cock touching places that I suspected had not been touched in years.

Tina’s breathing became laboured. I noticed a thin film of sweat covering her entire body now. Then she pushed her hips upwards and her body became tense. I kept up my pace when I felt her pussy starting to contract around my thick shaft. Tina cried out as she came. The ripples travelling through her cunt pushed me over the edge as well and I started emptying my balls in long jets of white cream, shot deep into her receptive snatch.

I kept pumping even as Tina relaxed, until I felt myself weak and exhausted. I collapsed on top of her. She kissed me and smiled, then kissed me some more – my neck, my shoulder, my cheeks. “That was incredible,” she said, “I don’t think anyone ever felt that good inside me.”

I smiled back at her. “I don’t remember anyone feeling this good around me,” I replied.

I then rolled off her, my still semi-erect cock flopping free. Tina got up, leaning on one elbow. “Can I clean you off?” she asked. I nodded. She leaned into my groin and took my cock into her mouth, licking and sucking the combination of our juices off. I couldn’t help but get hard again. Surprised, Tina took me out of her mouth. “You’re ready to go again?” she asked.

I shrugged, “I suppose that’s one of the benefits of having a 16-year old lover, they’re always eager and ready to go.”

She smiled and took me back into her mouth, turning her cleaning into a full blowjob.

I meanwhile placed my hand between her legs and slowly pulled her towards me. Finally she got the meaning and swung one leg to the other side of my head, her pussy now hanging inches from my face. I reached up and placed a few kisses on her labia. As a reaction she sucked hard on my cock.

I smiled, knowing we wouldn’t be leaving this bed for quite some time yet.