Old Acquaintances
By: Date: 2021.10.20. Categories: Sex Stories Tags: , , , , , , , , ,

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

“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

“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

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

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

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


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

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

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

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

“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

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

“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

“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

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

“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

“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.


“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

“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

“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

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

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

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

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

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

“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

“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.

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