Once gain my fans never cease to amaze me. One of my members wrote this fictional fantasy about me and it just turned me on. Nothing turns me on more than literate men who can express how I make them feel!
My Boss Rebecca by Horn Fly
Ever since I started working at this newspaper, I haven’t been able to keep my
eyes off of my boss. As the editor-in-chief for this small-town paper, Rebecca
seems to be pretty off limits and kinda conservative – at least on the surface.
As the sports editor, she and I meet almost daily to discuss what is going in the
sports section and how that relates to the rest of the paper. I love going in her
office, and yet I hate it at the same time. She’s older than I am, but she is so
beautiful…I mean hot beautiful. It’s nice to sit across the desk from eye candy
like her, but I have to be very careful not to get caught staring at her very
ample chest or her gorgeous neck. Oh my god how I’d love to stand behind her
and softly kiss her neck…and kiss those amazing lips.
Damn, I have to be careful. I work very hard to make eye contact when
Rebecca is speaking to me, but if she looks away for a second, I’m taking up all
that second to glance wherever I can. I’ve noticed enough just working around
her, being in her office, watching her walk by my desk that I have to be honest
and say that I’ve jacked off to her on multiple occasions. I wish she would give
me a look or something that would indicate that she would be into younger
guys. I’m certainly not bold or stupid enough to make a pass at her. I like my
So I have all these feelings and attractions to Rebecca and it seemed like it
wasn’t going to go anywhere past my mind and where my hand meets my cock.
Then one day she makes a strange request. She needs me to pick up a report
from the local police jury and bring it to her on Saturday morning…to her house
Because we are a small paper, we are able to have Saturdays and Sundays off.
On Friday night I pick up the report, and on Saturday I find my way to
Rebecca’s house, finding it after making a wrong turn or two. She lives just
outside of our small town in an area that isn’t in the middle of nowhere but is
still fairly private despite being just off a major state highway.
Honestly, as I walked up to her door, I never gave one thought to how much
I’ve wanted to fuck Rebecca in the past. All I really was thinking about was why
I was doing this on a day off. But, she’s the boss. I knocked, she answered and
invited me inside.
It took all I had not to pop a woody right there. As she walked by me, I saw
my boss – who acts and dresses conservatively at work and any other time
I’ve seen her – wearing a little black pair of booty shorts and a t-shirt that
barely came down to the top of the shorts. She filled out these booty shorts. I
knew Rebecca had a great looking ass, but seeing her in these shorts gave me
a whole new perspective. Her ass just popped in these things. And her chest
filled up the t-shirt, and it was one of those form-fitting t-shirts.
As always, I did my very best to maintain eye contact, but it was hard. I walked
in the house, she walked past me and said, “Come on in,” and I walked past
her entryway into her kitchen. The whole time I’m following her my jaw is
gaped as I stared at her ass. The kitchen was adjacent to her living room in
what was an open floor plan and in her living room was a sliding door that led
out onto a deck at the back of her house.
“You can just put the report on the bar,” Rebecca said. “Would you like
anything to drink?”
I wanted to say the first thing that came to my mind so badly (“Sure, the sweet
nectar from your pussy as you cum in my mouth.”), but I didn’t. She offered
me a beer, a glass of champagne, a Coke, tea, or water. Because I stopped
drinking a few years ago to keep from becoming a slobbering alcoholic like my
dad, I chose a Coke and passed on the alcohol.
As she poured my drink, I was just steadily looking her up and down. “Goddamn
her legs are gorgeous,” I thought to myself. And with her having no shoes on
and me having a foot fetish when I get horny, it didn’t take me long to see that
she had very cute feet, too. I’m just marveling at this unbelievably gorgeous
42-year old woman, knowing that I’m jacking off to her as soon as I get home
and thinking to myself, “Women in their 40s aren’t supposed to look this hot!”
And then it happened. She turned around, and before I could avert my
eyes to a more appropriate level, Rebecca saw that I was ogling her. I was
mortified. I knew for sure that I was going to lose my job or, at the very least,
have a very uncomfortable work environment for a while. I just thought to
myself, “Dammit you dumb fuck! Dammit!”
“What were you looking at?” She asked this question with a stern “mom” look
on her face with one eyebrow raised. I just knew I was about to get lectured. I
wanted to hide behind the bar and slink out of the house as quickly as possible.
But then…she asked, “Did you like what you saw?”
Was this question a trap? How in the hell am I supposed to answer this
question? I don’t want to sound like a pervert, but what if she liked that I
was looking? I had all these questions rolling threw my head and some mumbo
jumbo kinda stumbled and bumbled its way out of my mouth. I’m sure I
sounded like an incoherent retard.
“It’s okay if you liked it. It’s kinda flattering.”
“In that case, um, I was noticing that, ahem, that you really look, um…”
“Just say what you want to say,” she interrupted.
So with a swarm of 10 million butterflies frantically swirling inside my gut, I
blurted out, “Yes, I liked everything I saw! I more than liked it…I loved it! I think you look fucking amazing!”
I stopped suddenly when I realized I dropped the f-bomb in front of her. I was
raised that you don’t cuss in front of ladies, and you especially don’t drop the
f-bomb in front of them.
“Sorry about my language,” I muttered.
“Don’t worry about it,” Rebecca answered. “Do I look like a stuck-up bitch? If
you want to say I look ‘fucking amazing’ then feel free to say I look ‘fucking amazing.’”
I was surprised and supremely aroused at this point. I love cussing and dirty
talk. When I get horny, it just turns me on even more. I was so close to feeling
like I could say, “Hey, I’ve got a serious hard-on and want to fuck you until my
dick throbs,” and get away with it. Of course, while I would say that if Rebecca
liked that kind of talk, I would at least initially try to think of a more eloquent
way to put it. I felt like she had to be into me…at least a little. Surely she
wouldn’t act like this if she wasn’t, right? I just couldn’t be sure, especially
with a lady that I answer to five days a week.
As I stood there with some dopey look on my face, she asked, “What was your
With the boldness of a pair of brass balls I threw all my cards on the table and
surprised myself by saying, “Well, it was hard to tell because the best parts
were covered up.”
As soon as I said it, I cringed. Was I about to get my teeth knocked out like
Chiclets? Was I about to get fired? Was I about to get laid?
Leaning over the opposite side of the bar, Rebecca looked up at me with a
quaint smile and said, “If you want to fuck me, then just say it.”
“But you’re my boss, and you’re old enough to be my mom.” She would have
been a young mom, but since I was 25, she was old enough for sure.
“Then won’t that make it even more erotic?”
I had just jacked off to Rebecca to this point, but now the reality that I may
actually get to have sex with her was setting in. I had to admit that knowing
she was my boss and just three years younger than my mom escalated my
arousal. I suddenly felt way more erotic and naughty, and that made my dick
get that much harder.
She walked around to my side of the bar.
“What parts do you want to see?”
“I want to see every inch of you,” I replied with an air of confidence that I had
not had, now that I knew she wanted the same thing I did.
“All in good time.”
Rebecca leaned over and softly began to kiss my lips. She put her hand on my
shoulder close to my neck, and I stepped closer to her, pulling her closer as I
place my hands on her hips.
“Holy shit,” I thought to myself. “I’m making out with my boss, and she’s older
than me. This is so fucking sexy!”
Rebecca began to slip me her tongue and we kissed softly, yet passionately,
for several minutes. I broke up the kiss to make my way down to that gorgeous
neck that I’ve been wanting to kiss for a long time, and as I kissed her neck,
she worked her lips around to mine and began to caress my neck with her
tongue. I wanted to cum right there, but I managed to repress it.
She pulled away and asked me if I had ever had sex outside. Since I had only
had sex with one girl a few years ago, that was an easy question to answer.
Rebecca grabbed both of my hands and walked me outside to her back patio.
I did notice that she had some really cool outdoor furniture, including a nice
patio couch. We sat down together and embraced in a kiss once again. She
placed her leg over mine, and I began to gently caress it with my fingertips.
I worked my hand slowly all the way up her leg and began to rub inside her
booty shorts, and I realized that I was massaging her ass. When I did, she pulled
closer to me, pressing her breasts into my chest. This let me reach all the way
around and begin rubbing in between her cheeks. I wasn’t sure how Rebecca
would react to me rubbing around on her asshole, but with every stroke my
fingers got closer. And with closer stroke she said nothing. Finally I was there,
and she said nothing, so I rubbed around for a little bit. As we continued to kiss
and kiss necks and such, I wondered if she liked anal action. So I pressed my
middle finger into her asshole just a little. She pulled away from kissing and
said a smile, “Don’t worry, I like it there, too.”
Rebecca pulled up her t-shirt to reveal an amazing set of breasts. And right
out of my mouth came,” Goddamn, that’s fucking beautiful.” I knew what
she wanted, and I began to kiss her nipples and run my tongue over them as
she turned in the couch and began to lay back some. I continued to kiss those
amazing titties, and I worked my way off the couch and onto my knees in front
After a few minutes I began to work my way down her stomach. When I got to
her shorts, I slowly began to pull them down until finally they were completely
removed. And there before me was this clean-shaven, absolutely beautiful
slit. I stared for a few seconds at her unbelievable pussy before lowering my
face between her legs. I love to eat pussy. Man, do I love to eat pussy. It
almost seemed like Rebecca had this whole thing planned out because she had
apparently taken a shower shortly before I arrived. When I began to caress
her lips with my tongue, it scent was lovely and the taste was so scrumptious.
Her pussy was already wet, and I spent a long time there, listening to Rebecca
moan softly and squirm around. I slipped my middle finger on my right hand
into her pussy, getting it nice and slick. Then I slipped my finger between her
cheeks and pressed it against her asshole. With minimal pressure, my finger
slipped in. She jumped a tad and moaned a little louder before uttering, “Fuck
After a few more minutes of this, I noticed Rebecca’s moaning starting to get
louder and more frequent. Her body stopped squirming and began a slow,
steady pulsing, pressing her cunt into my face with each soft thrust.
“Do you care if I cum now,” she asked?
“Absolutely not,” I answered, pulling away just long enough for those two
The moaning became a groaning. Rebecca got louder and louder, and her body
movements became more and more intense. As I alternated between sucking
the tip of her clit and plunging my tongue inside her pussy and flicking her
clit with my tongue, she grew in volume. I began to feel the pressure on my
middle finger as her asshole clinched around it, and I knew she was about to
cum. Finally, she began to almost scream, “Oh my god! Fuck yes! Don’t stop!”
With a final scream her body convulsed, and even though I could feel her hands
pushing the top of my head, I would not release my mouth from her stunning
southerly lips. I pulled my finger out of her ass and reaching around with
both arms, grabbing her legs, and I pulled her into me. I continued to work
her pussy, which made her continue to moan very loudly, but I collected my
bounty. Her juices began flowing from inside, and I made sure to lap up every
drop I could.
She looked amazing. She tasted amazing. I wasn’t quite sure what would
happen now, but it didn’t take long for her to climb out of the couch onto her
knees and instruct me to sit. As I did, she asked if she could return the finger-
up-the-ass-while-I-give-you-oral-pleasure favor. I hesitated a bit but then
agreed. How bad could it be, right?
Before she started, I had to take her shirt off the remainder of the way. Then
Rebecca began to work her pussy with her middle finger and as she began to
swallow my cock, she slipped her finger into my asshole. I never in a million
years would have thought of that as a pleasurable thing to do, but dammit if it
didn’t feel great. As she ran her tongue up and down my shaft and caressed me
with her lips, she slowly pumped her finger in and out of my ass.
I was so worked up, I knew it wouldn’t take long to cum. And it didn’t. As she
felt the pressure of my ass around her finger, Rebecca plunged it as deep as
she could and quickly intensified the blowjob she was giving. With the loudest
orgasmic groaning to ever come from my mouth, I blew my load into her
mouth. She returned the favor by grabbing me and continuing to work my dick
until every last drop of cum was released. It was simply the most pleasurable
torture I have ever endured.
I’m so eloquent after sex. As soon as she was done, I said, “Goddamn mother
fucker! Holy fucking shit that was the most amazing goddamn blowjob! Fuck!”
Rebecca smiled at me, and I apologized for my outburst. “Don’t apologize,”
she said. “Just makes it obvious how much you enjoyed it.”
I also apologized for the quick ejaculation.
“Well, how about you stay for lunch, and after that you I’ll let your cock know
what the inside of my pussy feels like?”
Music to my ears.
I stayed, and we ate lunch…still naked as a pair of jaybirds. While we sat at her
bar eating, I pulled up her leg and began to massage her foot. I explained that
I have a foot fetish when horny, and I commented that she had a beautiful pair
of feet. “Do whatever you want with them,” she replied. So I rubbed them,
kissed them, and then began to lick around her toes before finally putting a
couple of them in my mouth.
We were done with lunch, and it had been a couple of hours since we each
came in the other’s mouth. She grabbed my hand and walked me back outside.
This time she walked to the rail of her patio overlooking her back yard. With a
full erection, I walked up behind her, placed my hands around her stomach and
embraced her with my dick pressing up against her ass. I slowly grabbed her
waist and began to kiss her neck again. As I did, she leaned back into me and
laid her head back. With one hand I moved my dick down between her legs,
and she helped guide it to her once-again soaking wet pussy.
Before inserting my dick, I slid it back and forth against her lips and massaged
her bountiful breasts. We both moaned with pleasure, and after a few minutes
I pressed my head into her slit. He didn’t slip in like I assumed he would. So
I slowly pressed a little bit, pulled back, pressed again, and did that until my
cock slipped right into heaven.
I slowly worked my average-sized cock in and out, almost like I was trying to
massage the inside of her pussy. As I did, I kissed her shoulders softly and ran
my fingers up her sides and across the small of her back. After a few minutes
of this, I wrapped my arms around her and began to kiss the back and the
side of her neck. Because I had just cum a couple of hours earlier, I was not
concerned about how quickly I would cum this time. After god knows how
long of fucking Rebecca from behind, she pulled away and swung around to
face me. She threw one leg up on my hip and eased her cunt back onto my
cock. This time we worked together, pumping our pelvises in perfect rhythm
with each other. The tempo got faster and faster, and Rebecca’s moaning got
louder and louder. Once I realized she was about to cum, I felt more and more
aroused and the tingling below my sack grew strong. She leaned back against
the railing, pointing her mountainous tits towards the sky. I couldn’t resist. I
wrapped my mouth around one of her nipples and began lick around her nipple
and flick it with my tongue, all the while still able to maintain perfect rhythm
with Rebecca’s thrusting pelvis.
And it happened. It was almost magical, and I can’t thoroughly explain the
sensation that ran threw my dick, my sack, my general crotch area and up my
torso. It was the first time I had been able to sync my orgasm up with another
woman’s. Rebecca and I climaxed together to a chorus of “Oh my gods”
and “Fuck me’s” and “Fuck yeahs” and “Goddammits” and “Holy shits” and
whatever the hell else came out of our mouths…well, mostly mine.
Having worked up a thin lather of sweat, Rebecca and I embraced each other
with my dick still inside her and her leg still wrapped around my hip. I grabbed
her leg to hold it up and we kissed for several minutes. It was undoubtedly the
most amazing day of my life.
And you know what? It wasn’t over. She asked me to stay for dinner and then
to stay the night. So I did. She laid on her back and let me fuck her titties.
Everytime the tip of my cock emerged from the tops of her tits, her mouth was
waiting for a sweet, wet embrace. As much as I wanted to blow my load in her
face, I wanted to cum inside Rebecca again. So we finished up doggy-style.
Over the remaining nine months I would spend in that small town working
at that small-town newspaper, Rebecca and I were amazing lovers. We role-
played some. Even though it was weird and awkward at first, two of the roles
we played were aunt-nephew and mother-son (sick, but strangely erotic and
arousing). We experimented with different things and positions and toys. I even
let her talk me into letting her fuck me in the ass with a strap-on dildo. We
did the occasional threesome. She had a girlfriend who was 10 years older than
me – blonde with creamy white skin and a gorgeous body. Her face was “eh”
but the rest of her was great. After I let her talk me into using a strap-on on
me, I let her talk me into the real McCoy…a mmf bisexual threesome. That
was truly an amazing and unforgettable encounter, but my preference was
strongly one-on-one with Rebecca, who I grew to love dearly. I didn’t love her
in like a husband-wife or boyfriend-girlfriend way but rather as a lover and a
friend…and yes, sort of like an aunt. A really cool, horny aunt.
We had sex on every piece of furniture and on every surface in her house.
Because she lived outside of the town, we even dared to fuck in her front
yard at night…late at night. We fucked in her office at the newspaper and in a
couple of other rooms in the newspaper, always after hours. We fucked in our
cars, on the beach at a nearby lake (again, very late at night), down a dirt road
in broad daylight. But our favorite spot was outside on her back patio. There,
more than anywhere else, we felt like we could cut loose and scream or moan
or holler or whatever. It was our sex haven.
It’s been a little over 10 years since I left that town, and I’ve lost contact with
Rebecca. But I still think about her quite often, and yes, she is the object of
my thoughts on many, many occasions when I masturbate. Maybe one day she
and I will find each other again and rekindle some old magic.