Cougar
By A.J. Brown
Horny woman and young virgin cross paths


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It was just another night at work for Caleb - another night working at the gas
station. He never really studied in high school nor put in a whole lot of
effort. He spent most of his time just sitting around the house playing video
games. He got through high-school but got through it with bad grades and
didn't even have the motivation to try to apply for college.

All of his friends had gone away to college and most of them weren't even in
town anymore. He lived in a small town and his friends just couldn't wait to
get away and party. There was hardly anyone left now and after a long day
working at the gas station, Caleb would just go home to his parents' house and
play more video games.

He talked to his friends sometimes through email and Facebook. They were
having fun at college - and they were getting laid. Caleb still hadn't had
sex, not in his life. He was an 18-year-old virgin and that was probably the
worst part about working at this service station instead of going to college.

He was working behind the register by himself. No customers were in the store
right then and the only other person in the building was his manager, Brandy.
Brandy wasn't a bad looking woman - at least for a woman that was
forty-years-old, smoked, and overall was just a pretty white-trash woman. She
sat in her office with the door open, smoking a cigarette, and she was doing
some paperwork. He thought about his friends being away at college looking at
some hot, young girls, while he was sitting there working at a gas station
looking at Brandy.

He heard the bell ring that was on the entrance to the store and he saw
someone walk in. It was a woman that appeared to be maybe fifteen years older
than Caleb was but it was often hard for him to tell. She was a decent looking
woman but being stuck behind the counter of a service station for forty hours
a week made a lot of women look a lot hotter than they normally would have to
Caleb. He actually felt himself starting to get a hard-on in his pants.

She had long, brown hair and he figured that her face was pretty cute, at
least for someone that was quite a bit older than he was. She wore a navy blue
hooded sweatshirt and she had a tight pair of jeans on that showed off that
her thighs were actually pretty thick for a woman that really didn't look too
big otherwise. She stood at maybe 5'4 and couldn't have weight more than 135
but those thighs of hers did look pretty big, all things considered. She wore
a white pair of running shoes and just did not seem to care too much at all
what she looked like. This was what it had come to for Caleb - these were the
kinds of women that were making him get a hard-on. He still felt his cock
growing in his pants.

"Can I get a pack of Newports, honey?" she said to him and she started to pull
some money out of her pocket.

Her voice was actually pretty cute and Caleb thought that if he just heard her
speaking on the telephone and didn't see her that he would have thought that
she was a lot younger than she looked. If Brandy wasn't there then Caleb most
likely would have sold her the cigarettes without thinking twice about it.
Store policy was to ID anyone that looked like they were under 30. But Brandy
was there and Caleb didn't want to risk getting in trouble.

"Can I see your ID?" he asked her and she immediately got a shocked look on
her face.

"Are you serious??" the woman said to him with disbelief. "I'm 43 years old!"
He hoped that the woman would follow her complaint up by showing him her ID
but she didn't do so and that made him start to feel uncomfortable.

"I just need to see it" he said and this woman almost intimidated him more
than Brandy did to the point where he almost felt like he was going to have to
give into her.

"Brandy!" the woman yelled a bit angrily and she yelled back towards Brandy's
office.

"She's good, Caleb" Brandy yelled back without even bothering to look up at
Caleb. "She's my older sister."

"Oh thanks a lot, you bitch" the woman said jokingly with a smile as Caleb
reached to get her the cigarettes. "Of course you gotta mention that I'm the
'older' sister." Caleb handed the woman her cigarettes. She took them and gave
him a ten-dollar bill, still looking at her sister, and still not looking at
him. She was pretty cute for a woman that was sort of white trash.

"What's the difference, Tammy?" Brandy said back to her sister as Caleb handed
her the change and she took it, still without looking at him. "You just told
him how old you were anyway."

"Shit, you're right" Tammy laughed with a ditzy laugh as she started to walk
behind the counter towards Brandy's office. "I'm not even thinking clearly
anymore."

Tammy walked right back into Brandy's office, had a seat, and lit up a
cigarette. She actually put her feet up on Brandy's desk as she smoked. Caleb
just stood behind the register watching the two sisters interact out of the
corner of his eye while he worked. He couldn't believe what his life had
become.

"So who's that guy out there working the register?" Tammy asked Brandy as she
took another drag of her cigarette.

"That's Caleb" Brandy said and she looked pretty busy with her paperwork.
"Kid's a good worker. A little weird, but a good worker."

"Yeah, he's weird alright" Tammy said and the two of them were talking loud
like Caleb wasn't even there. "Kid IDing ME for cigarettes? Pretty fucked up."

"He was just doing his job" Brandy said to her.

"He's pretty hot" Tammy said and she took another drag of her cigarette. "Got
really nice arms."

Caleb couldn't help but be flattered. He had been working his arms out plenty
in his spare time and he was glad that someone noticed. And Tammy definitely
didn't seem like the kind of person that would pay a compliment that she
didn't mean. He pretended like he didn't hear her although she was talking so
loud that he couldn't imagine that she didn't realize that he did. Brandy
continued to do her work and didn't say anything.

"I would definitely like to have sex with him" Tammy said and the 18-year-old
virgin quickly went from feeling flattered to feeling quite uncomfortable. He
did his best to pretend like he didn't hear her say that. But he had this fear
that she just knew and that she was going to call him out on it with his boss
right there.

"Tammy!" Brandy said with a surprised smile and she finally looked away from
her work and at her sister. "What's he, twenty four years younger than you
are?"

"Twenty five?" Tammy laughed. "I just turned 43, remember?"

"OK so don't you think he might be just a little bit young for you?" Brandy
asked her.

"I know, but, whatever" Tammy said back. "I haven't had sex in awhile now. I'm
horny."

"How long has it been for you now?" her sister asked curiously.

"Way too long" Tammy said almost like she sounded depressed. "Three weeks."

"Jesus, you gotta be going nuts!" Brandy said like Tammy had just told her
some shocking news. "How long has it been since you've gone that long?"

"Um, like never" Tammy said. "I am going nuts about it too. That's part of the
reason I want to have sex with your little cashier out there. Look at him out
there still so young and good looking. He's probably had sex with a different
girl every day this week. Meanwhile, here I am ... "

Caleb could feel his stomach turning getting nervous as he feared that at any
second Tammy was going to yell out and ask him how long it had been since he
had gotten laid. There that woman complained about how bad it was going three
weeks without sex while he had never done it in his entire life. He always
felt like he was better than Brandy just because she had grown up to be a gas
station manager and since he was still young he felt he had plenty of
opportunity to do plenty more with his life. But right at that moment he had
never felt like more of a loser.

Finally a customer came in to prepay for some gas and Caleb was very thankful
that there was a customer there to make sure that Tammy didn't try talking to
him. A couple of more customers came in and it started to get a bit busy.
Caleb tried to focus on the customers and not what Brandy and Tammy were
talking about.

There was quite the rush of customers after that which kept Caleb busy and he
enjoyed it. Brandy didn't even bother to come out and help him with the rush
that was coming in and she just continued to hang out in the office with her
sister. He could hear them talking more about sex which made him feel like
that much more of a loser. He was kept pretty busy for an hour or so when the
customers finally stopped coming in. Now it was just him behind the counter in
the store again while Brandy and Tammy were still in Brandy's office.

"Alright, well I gotta get the hell out of here" Brandy said to Tammy as she
stood up. "I've already been here for twelve hours today."

"Jesus Christ" Tammy said as she took another drag of her cigarette and it
seemed like she had been smoking the entire time since she had been there. "I
don't know how you do it."

"Neither do I" Brandy said with a not-amused sounding laugh.

Caleb then watched as Brandy walked out of her office but Tammy still stayed
sitting there, smoking a cigarette, and playing around on her smart phone.
Brandy was definitely leaving but Tammy didn't look like she was going
anywhere. Why would she be staying if Brandy was leaving? Caleb now felt
extremely uncomfortable.

"Alright" Brandy said to Caleb with her raspy voice as she pulled her own pack
of cigarettes out of her purse. Her sister was three years older than she was
but if one were to hear both of their voices they'd think Brandy was probably
fifteen years older. "I'm going home for the day. You know how to close up.
And just so you know ... whatever happens between you and my sister after I
leave is between the two of you. Don't worry about me being mad about it or
anything. You two can even go back in the break room there if you want. See
ya."

Brandy gave Caleb a smile and it was probably the nicest that she had actually
treated him the entire time that he worked for her. He watched her walk out
the door and then he looked back at her office. He thought that maybe Tammy
would wink at him or something which would probably make him nervous. But that
didn't happen. She just sat back there smoking a cigarette and playing around
on her phone. With the two of them alone in the store, the young guy still
felt pretty nervous.

The clock struck midnight and it was time for Caleb to close up the store. He
had balanced out the cash register, checked the gas levels out front, and
swept the floor. Tammy was still in the back office. He turned one of the
lights off which got her attention. She looked at him for the first time since
Brandy left, got up out of her seat, and walked towards him.

"So" she said to him as he looked at her nervously. "You gonna have sex with
me or what?"

"Um, um, yeah s-sure" he stuttered.

"Jesus, don't sound so excited about it" she said as she started to walk
towards the break room. "I know I'm old and all but I'm still damn good,
believe me. Grab a box of condoms off of the wall there and bring them back
with us. I'll have Brandy take them out of your paycheck. Hope you don't
mind."

As she walked towards the break room Caleb noticed for the first time that her
ass was rather large especially in comparison to the rest of her body. It was
still pretty firm though and it actually turned Caleb on that her ass was
rather big. He felt his cock rapidly growing in his pants as the horny young
guy followed the experienced woman back into the break room.

"So how longs it been since you've been laid?" she asked him as they now stood
in the break room all alone.

"Ah, I don't know" Caleb said and he felt himself start to blush as he looked
at the ground.

"What do you mean, you don't know?" she said curiously and now it sounded like
she was on to him a little bit. "How many girls have you had sex with in your
life?"

"Jeez, I don't even know" he said extremely uncomfortably as he looked at the
ceiling.

"Are you a virgin?" she asked with surprise and Caleb didn't answer her. "Tell
me that you aren't. Oh fuck me, you are!"

She fell back on the leather couch that was in the break room, looked up
towards the ceiling, and buried her face in her hands. This 43-year-old horny
chain smoker was making him feel like the biggest loser in the world. He just
wanted to be away from her but he feared trying to leave would just lead to
more ridicule.

"So do you really want to have sex with me?" she asked him as she took her
face away from her hands. "You're not one of those good little Catholic boys
that wants to wait until marriage or wait for 'the right one' or anything like
that, are you?"

"No, no" Caleb said trying to sound like he was tough. "I definitely want to
have sex with you."

"Well alright" she said to him. "I didn't really think 18-year-old virgins
existed in this day and age. I need to get laid cuz it's been way too fucking
long and you ... well ... you just need to get fucking laid. So take your
clothes off and let's get this over with."

Tammy didn't even waste any time. She immediately pulled off her sweatshirt so
he could see her there wearing nothing up top but a black bra. She took that
off right away as well and Caleb realized that he better start undressing as
well or it was going to look weird.

He started taking off his clothes and Tammy was just undressing without paying
any attention to him. She kicked off her sneakers, pulled off her socks, and
then took off the jeans that she was wearing. Her thighs looked even bigger
now that she had her pants off and they were definitely a lot bigger than
Caleb's were.

When she was completely naked Caleb saw that her pussy was quite hairy. He
continued to take his clothes off until he was completely naked. Tammy started
fingering herself and looking up towards the ceiling, not paying attention to
Caleb. His cock which was rock hard earlier had now gone completely limp based
on how nervous he was, being around this woman.

Tammy was still taking care of herself and Caleb wasn't sure exactly what to
do. He had never had sex before and didn't know how to go about this. His dick
was still completely limp but he didn't know what else to do. So he pulled out
one of the condoms and tried putting it on. Tammy finally realized what he was
doing as she watched him unsuccessfully trying to get a condom on his limp
cock.

"What the hell are you doing??" she said to him in a tone that really made him
feel embarrassed. "That's not going to go on you until your dick is hard. Come
over here."

Caleb threw the condom aside with frustration and walking towards this
impatient, naked, older woman was not getting him aroused in the least. He
stood in front of her and she started jerking him off but it wasn't doing
anything for him. She started getting annoyed and doing it even harder but she
was making Caleb so uncomfortable that it wasn't working at all.

"Oh for fuck's sake!" she yelled out and then she let go of his dick. "You're
hopeless. I finally get an opportunity to get laid and it ends up being with a
scared little virgin. Fuck my life. Well I need to get something out of this.
Suck on my toes." She then lied down on the leather couch and rested both of
her bare feet on the arm of it.

"What?" Caleb said to her.

"Look, I'm really horny and I need to get something out of this" she said to
him. "It really turns me on when a guy sucks on my toes. So make yourself
useful and do that for me at least. And I promise you that you don't want to
piss off a 43-year-old horny woman so you better get going and do it."

Caleb was an 18-year-old man that worked out a lot and here he was intimidated
by a 43-year-old woman. The fact that she was his boss's sister did not help
matters at all. He didn't want his boss to be angry at him for any reason but
even more than that, he definitely didn't want his boss to know that he was a
virgin that didn't even know how to have sex. Not only did Tammy intimidate
him but she intimidated him to the point where he actually felt he needed to
do the extremely degrading deed of sucking on her feet.

And so he did it. He got right on his knees in front of the woman's bare feet
just like she told him to. He hoped that maybe once she saw how demeaning it
was for him that she might lay off but she just proudly lay there like it was
something that he should be doing. He got to work sucking on her toes.

And the second that his mouth touched her toes, as humiliating as it was for
him, he felt his cock instantly get rock hard. He had always had a foot fetish
- looking at women's feet just turned him on. It was something that he not
only kept to himself but also was in denial about it to himself most of the
time because he was so ashamed of it.

But once he tasted the taste of those toes as he sucked on them his horniness
took over and he started going to town. He sucked on every one hard, enjoying
the taste of them so much. His longtime fetish was finally coming true as he
had never done this before. In addition to sucking on each one of her toes he
started kissing and even licking the bottoms of her feet as well. His cock was
going crazy and Tammy was moaning with complete satisfaction.

"Oh yeah!" Tammy yelled and she was clearly enjoying this a great deal as
well. "Oh fuck yeah, that feels good. I'm so fucking wet right now. Come eat
me out!" That was also something that Caleb had never done before and he was
far from eager to do it.

"Um ... " he said.

"I told you not to piss me off!" she yelled at him with an extremely impatient
tone that he had never heard in another human being before.

This time she didn't wait for him to respond. She kicked out her lower legs,
actually grabbed his neck with her legs, and pulled his face right into her
wet pussy. She then wrapped her large thighs right around his neck and head to
make sure that he wasn't going anywhere.

"You better do a good fucking job of this" she said, breathing kind of heavily
as she said it. "If you don't I'll fucking crush your head with my thighs, I
swear to God."

Just to get an idea of exactly where he was with everything, he grabbed her
thighs with his hands and realized that no matter how much he had been working
out his arms, there was no way he'd have a chance of pulling his head free
from this woman's big thighs. Her threat scared him and he began eating her
pussy.

He got to work but this was not enjoyable for him like sucking on Tammy's feet
was. In fact, it was not enjoyable for him at all and he wanted to stop. But
as he licked her pussy more he felt her tightening her thighs around his head,
probably not even realizing that she was doing it, but that reinforced to him
that he better keep doing what he was doing, and do it well. Tammy seemed to
be enjoying it based on the way she was moaning.

"Oh fuck yeah!" she moaned and Caleb really wished that he could be getting
the same kind of enjoyment out of all of this that she was. "Oh it's been
awhile since I've had anything like this. This is so fucking good. I'm gonna
cum. I just came!" She used her foot to rudely just push Caleb's face away
from her crotch and then she sat up looking extremely satisfied.

"Wow I just came but I definitely feel like I could go again" she said. "Too
bad you're just not ready for sex."

She actually didn't sound that mean when she said it but Caleb felt extremely
insulted and embarrassed nonetheless. He had just shown her a really good time
and he would have felt cheated if he didn't get the same thing. His hard-on
had completely gone away when he was eating her out but now he knew exactly
how to get it back.

"If you let me suck your feet again, I bet I could get hard" Caleb said shyly.

"What?" she said back to him and she didn't sound so nice this time.

"My dick was really hard when I was sucking on your feet" he said. "Let me do
that again and then we can have sex."

"Well you're just some kind of freak, aren't you?" Tammy laughed with a laugh
that didn't sound very friendly. "You seriously got turned on when you were
sucking on my feet? Wow, that's fucked up. And so is you asking me to let you
suck my feet just so we can have sex. But hey - I gotta get out of this
drought and you just need to get laid so I guess we both gotta do what we
gotta do. So get to work."

Tammy leaned back on the couch and put her bare feet back up on the arm of the
chair. They looked extremely inviting resting there waiting for him and just
looking at her sexy feet made Caleb not even realize the negative things she
said about him. He put his face right into her feet and began kissing,
licking, and sucking.

"Yeah, that's right you little bitch" Tammy said and now she sounded like she
was enjoying this whole thing. "Suck on my feet and do it good."

Caleb worked hard sucking on Tammy's toes on her one foot while she excitedly
started to slap him in the face with her other foot. It was extremely
humiliating for him as she did it but it made his cock grow even more so he
kept sucking on her toes. She was treating him like such a little bitch but
they both really seemed to be enjoying themselves.

"Oh my God my cock is going crazy here!" he yelled out like he was completely
at her mercy. "Holy shit, do I want to fuck you."

"Ha-ha-ha" Tammy laughed with extreme satisfaction as she slapped him in the
face with her foot again. "You want to try to fuck me again, you little bitch?
Give it a try. Let's see what we can do here."

Caleb looked at the extremely satisfied look on this woman's face. They made
eye-contact and there seemed to be an unspoken understanding between the two
of them that she was just the superior one of the two. Caleb pulled out
another condom and this time he had no trouble getting it on.

"Wow, even with your cock rock-hard that's gotta be the smallest one I've ever
seen" Tammy said with amusement as she spread her legs. "Guess beggars can't
be choosers though. Show me what you can do with that thing."

Wasting no time whatsoever, Caleb stuck his rock-hard cock right into Tammy's
wet pussy. It was just what his hard cock needed and he started fucking her
like crazy. He moaned like he had never moaned before as he fucked her harder
and harder. But Tammy didn't look impressed. She just sat there looking at him
with a look on her face like she wasn't getting anywhere near the pleasure
that he was.

Seeing that look on her face made him go even harder which was doing plenty
for his own pleasure but didn't appear to be doing anything with her. He felt
himself cum a bunch and then he pulled out. He took a deep breath then looked
at Tammy who just shook her head. She didn't waste any time getting herself
dressed. Caleb just lied on the ground after the amazing experience.

"Well that was pretty awful" Tammy said once she had all of her clothes on and
she made her way to the door. "Worst sex I've ever had by far. Glad you seemed
to enjoy it, though. I hope you did, anyway. Because there really aren't going
to be too many girls out there willing to have sex with an 18-year-old guy
with a freaky foot fetish that's only had sex once in his life." Tammy left
the room while Caleb remained lying on the ground staring at the ceiling. He
had finally lost his virginity but he was definitely not feeling good about
himself.

**Email me at ajbrown2005@yahoo.com for more information on Quick-Start
Stories or Custom Stories**