So I’m 40 years old, married with two teenaged girls. My life is
pretty good. I make pretty good money as a computer consultant and
work from my home office. I love my wife and my two daughters.
One is 20 and in college. The other is a sophomore in high school.
Life is good.
One of my wife’s good friends is a single mom. Her name is Julie and
she has 3 daughters. Amanda, her oldest is 15 and goes to the same
high school as my youngest. Her other two daughters are Sue and
Jenny, 13 and 11 respectively. Julie is pretty good looking, good
body, and a simple uncomplicated face. Her hair is naturally blond as
is her intellect. Her kids share all of her attributes, or so I
thought. I was nice to Julie, but basically dismissed her. Same with
her kids. Until my wife came home and told me a story about Julie and
her oldest, Amanda.
As my wife tells it, the two were driving somewhere or other when
Amanda blurted out, apropos of nothing, “Mom, have you ever taken it
up the butt?”
I’m told this nonplussed her mom. I can imagine. But Julie recovered
and replied, “no.”
Amanda then told her mom that she’d let her boyfriend fuck her in the
ass. The reason she explained to her mom was that her boyfriend
had gotten mad at her when she’d told him that she’d given her
virginity to some guy she hardly knew at a party… because she
wanted to know what it felt like.
I didn’t get the details of how that transgression against her
teen love had warranted an ass fucking, or who had initiated
the desire to take it up the butt, but that’s what had happened.
Well, Julie asked her daughter if it had hurt, and upon Amanda’s
answer of ,”yea, kinda” she’d told Amanda that maybe if she didn’t
like it she shouldn’t do it. Then Julie told my wife, and
my wife told me. TMI.
A bit about Amanda. She’s 15, a sophomore in high school. She used
to be chunky, but when she hit puberty full-on as a freshman she got
all emo and depressed and dropped down to about 105 lbs. Amanda now
had a nice body, a tight waist, nice b cups and hips that were
just right, flared but not fat. She had blond hair like her mom’s but
wore it with long bangs that usually covered most of her face. She
outlined her eyes in that black mascara, making her look a bit like
a raccoon. I hardly got to see her eyes though as she perpetually
looked down, avoid eye contact with everybody.
I had thought Amanda was a bit dumb based on tales from my wife, but I
was wrong, sort of. When she was happy (not often) she scored 98 or
better on all her school tests. When she was depressed (generally due
to restrictions put upon her for being suspended from school
for smoking and drinking at lunch) she dropped to Ds. As I said
earlier, she always looked down, rarely talked, and when she replied
to a question her answer was generally mono-syllabic.
I personally think she has a very low self esteem and that she has no
drive, no goals and has never learned to express herself. Her
father was a drunk who jumped onto the unemployment and disabled
roles as fast as he could. He ignored the kids and treated her
mom like shit. I think her early experiences shaped her into
a quiet unhappy child with no ability to speak her mind or relate
to others.
She went along with her friends, never standing out, never really
giving an opinion or taking the lead. Sort of a zombie in my
estimation. Her mantra, if she had one would have been ‘whatever’.
So, Amanda got in trouble again. She and some friends were smoking
pot in a car in the school parking lot after school. Some one
snitched and she got taken down the police headquarters, given
a good scare and released into her mom’s custody.
Julie decided Amanda couldn’t be trusted to stay out of trouble
after school so my wife agreed to pick her up from school every day,
bring her. and keep her out of trouble until her mom picked her
up at 5:00. My wife picked up our own sophomore every day after
school anyway so it was not a big deal. Occasionally, when my
wife was busy, I’d pick the girls up and bring them home.
On the occasions when I drove her to our home I began engaging Amanda
in conversation. Mostly she’d answer with “un-huh” or “yep”, or
her favorite “I don’t know”, but it was 15 minutes and often my
daughter would stay after school for activities. Fifteen minutes
of no conversation was too much for me, so I drew her out.
It took a few months, but she slowly came around, asking me a
question or two, telling me about her day at school and even mentioning ‘
boys’ now and then.
I didn’t mention it, but I’d often think about the butt fucking
story. It got me a bit hot, but it wouldn’t be appropriate
for a forty year old man to discuss butt-fucking with a fifteen
year old girl.
One day though I got my chance, sort of. My daughter had stayed
after school and it was just Amanda and me in the car.
I went through the basics, asked her about school, how life was
treating her, and told her a harmless joke. Conversation lagged.
There was silence for a minute or two and then Amanda ventured,
“There’s the boy at school…”
“Un hun”, I replied. “A boy?”
She was looking down, as she always did, but I gave her quick side
long glance and she was showing that little half smile she had. Her
half smile always looked conspiratorial, like she was trying to hide a
secret, one you’d die to hear.
I waited. Another minute went by and then she said, “Yea, I kinda
like him.”
“Oh yea. Let me guess, drugs, booze and pot?”
“No, he’s clean,” she murmured, her smile brightening a bit,
perhaps in anticipation of my silent approval.
“Well, that’s good.” Amanda smoked, did pot and drank a bit. I
thought she was just following along with her friends, but who knows.
More silence. Then Amanda said, “I haven’t slept with him… yet.”
I nodded but said nothing. Maybe she was trying to shock me. I don’t
shock easy. But her words got my mind buzzing. My mind raced.
Amanda was on the pill (by order of her mom some time ago. She
knew her daughter well enough to fear an unwanted pregnancy).
Amanda did whatever was easiest. She was a follower. She seemed
to have no will of her own. My mind went to the “butt fucking”
episode, and my cock twitched.
So now I had something to think about. I thought fast and made
a snap decision. Sometimes you just know when to make a move and
I felt I knew enough of Amanda to say what I said next.
“So Amanda…”
“Yea?”
“Can I ask you a personal question?”
“I guess so,” she said with a slight shrug. Her voice was neutral,
no inflection, no worry, no anticipation. Whatever.
“Well, um, this is a bit embarrassing. Do you promise to keep it
to yourself?””
Another shrug. Another monosyllable answer. “Sure.”
“Well, ” I started. “I’m turning 40 in 3 months.” I paused, not
sure how to start this next sentence. “Um, I heard second hand
that you had, um… anal sex with your boyfriend. True?”
She looked down, the ghost of a smile on her face? “Yea.”
“OK, ” I continued. “So, you and I are friends. And look,
you can just say no, but I’ve wanted to butt fuck a girl for years but
my wife said no, and I don’t do hookers and I’ve been thinking about
you letting your boyfriend fuck you in the ass.” I was rambling.
“Would you let me fuck you in the ass just once?”
I started back pedaling, terrified of what she might say or do.
“Look, ‘manda, you can just forget what I said. I’m sorry. I
shouldn’t have said…””
There was silence in the car. I was afraid to look over and see
her expression. I stammered. “Look, just forget I said it. OK? I
won’t bring it up again. Just don’t tell your mom.”
More silence. Finally she said “ok.”
“Good,” I said. “I’m sorry.”
“No, I mean OK. I’ll let you fuck me in the butt.”
My cock got hard and my brain got soft. I blanked.. We were only
about 2 minutes from home and it was all I could do not to floor it
and probably drive the car into a tree. We said nothing more on the
drive.
I almost laughed picturing it the post-accident interview with the
police. “Yes officer. This fifteen year old told me I could butt
fuck her and I had to get home fast.” Oh, that would go over well.
Well as luck would have it, we made it home safely and here was nobody
home and there wouldn’t be for about two hours. We walked into the
house, no word spoken. She put her book bag down and said, “where?”
“The guest room, please.” Please? I can’t believe I said that. “Um,
I don’t have any lube, ‘manda.”
“We used squeeze margarine,” she replied, heading up the stairs.
“It was kind’a gross after words, hard to clean off, but it
worked.”
Margarine? Hmmm. I decided on olive oil. We were going greek after
all. I silently smiled at my own little joke. If I’d had half a
brain I would have punched myself in the face and walked away.
But I was a forty year old anal virgin and fuck the consequences.
By the time I got upstairs Amanda had removed her top and her pants
and was slipping out of her panties. She left her bra on. I took in
her teenage beauty and gasped. She was beautiful and so hot. I stood
there with the olive oil in one hand not moving. She looked down
and saw my cock pressing against my zipper. She smiled that half
smile of hers and waited.
I came back to myself and quickly shed my pants. Then I pulled off my
shirt, then my underwear.
“Yours is bigger than Robbie’s she said.” My ego swelled a bit at
her comment. Yea, bigger.
“God, you’re beautiful,” I said out of breath. Her bush was brown
and neatly trimmed. “Can you take the the bra off?” I asked.
She reached behind her back, twisting her arms in that way only women
can to undo the snaps of her bra, and just let it fall to the floor.
Her nipples were hard and her firm young breasts pointed skyward, as
only a teen age girl’s can. Now she looked me in the eyes, saw my
expression and looked back down at her feet.
I wasn’t sure if it was allowed but I stepped in close and pressed
myself against her, hugging her softly. I reached with my hands to
gently press them against her ass cheeks and pressed my cock cock into
her stomach. I would have kissed her, but something told me not to.
I wasn’t her boyfriend. We weren’t lovers. This was a favor.
Her hand reached between us and she gently grasped my cock, her
fingers running up and down it before gently cupping my balls.
I gasped, almost coming in her hand, but I was stronger than that.
Anyway, if I had shot my load into her hand at the first touch, I
probably would have been too embarrassed to go on.
She gently broke from my grasp and turned toward the bed. “Start
slow,” she said, climbing into the bed and getting on all fours.
I got up behind her. “How many times have you been butt fucked?”
“Just once.”
I maneuvered myself behind her and opened the bottle of olive oil.
The bottle had one of those plastic tops to prevent the oil from
just pouring out. I stared at her ass crack. I took in the sight
of her anal rose, the pouch of her pussy and I marveled at my
luck.
I drizzled some of the oil into her ass crack, not much, just a thin
bead that ran down to her anal rosebud, a bit of it running down to
her pussy.
Damn, I needed towels.
“I’ll be right back,” I said, jumping out of bed. “Don’t move.”
I ran into the master bath and got some paper towels. Climbing back
into bed I poured a bit more olive oil down her crack and then caught
the flowing stream with a finger where it met her ass hole. I gently
rubbed it around her the tight bud with my finger and gently pressed
my finger into her. I could feel her start slightly, but she didn’t
say anything.
I sawed my finger in and out of her again and again, adding more olive
oil every few strokes. My finger got that shit stink on it, but that
sex smell combined with the shit stink was the fragrance of ambrosia.
I poured more olive oil and added a second finger. Again she started
slightly but said nothing.
After a few minutes of this I pulled both fingers out and cleaned them
on a paper towel. Then I used the towel to clean around the target.
And finally ripped off some sheets and placed them under her.
“You ok?” I asked her.
“Yea,” she said quietly with no real inflection.
I covered her body with mine and gently kissed her shoulder. I
reached around with my left hand and gently caressed one of her tits.
“I”m gonna lube up and then put my cock in your pussy.”
“What?” Finally some emotion, and a bit of surprise. She might
balk, but I thought I could handle her.
“I’m just gonna get a head of steam going in your pussy. then I’ll
switch to your ass. It’ll hurt less this way since you’re not
really used to ass fucking. You’re on the pill, right?”
“Uh huh.”
“OK, so as soon as I feel my self getting close to coming I’m gonna
switch to your ass, ok?”
“OK.”
I kissed her shoulder a few more times. I smelled strawberry in her
hair, inhaling softly. I gently flicked a taut nipple with a
finger. “Relax.”
I backed up a bit and looked at that inviting ass and pussy. I
gently bent down and kissed one of the half moons of her
ass cheeks. Her as was alabaster and soft, the perfect ass of
a beautiful teenage girl, unspoiled by age and attention.
Telling her I was gonna fuck her pussy for a bit had been a risk. I
wasn’t sure she didn’t just see this whole thing as doing me a quick
favor by letting me fuck her ass. She might not be so giving when it
came to her pussy. But I might never get another shot at her.
I wanted to feel my cock in that fifteen year old tight pussy. I’d
finish up in her ass, but I’d enjoy my time in her cunt too.
I drizzled some olive oil on my hand and wrapped it around my cock,
spreading it around. I already had a good bit of pre-cum on the tip of
my cock, but wanted the entire shaft well oiled. I got my cock good
and soaked with olive oil and then capped the olive oil and gently tossed
it on the floor.
I reached my thumbs between her ass cheeks and spread the lips of her
pussy with them. God what a sight. As I gently spread her nether
lips I saw some moisture, a small sign that maybe she was a bit
excited and maybe not just a fuck doll. She was wet.
I aimed my cock at her pussy and gently pressed it into her. God,
she was good and tight. I paused for a moment, just looking at my
cock half-buried in her pussy. In a moment half of it was gone, then
three quarters, then I was buried in that sweet 15 year old tight
pussy.
I could have come with about five strokes. It’d be difficult not to
come in five strokes, but that wasn’t what we’d agreed to and
though her pussy was tight and right I wanted to cum in by the
back door to heaven, not the front.
I again folded myself over her body and massaged her tits with both
hands, gently whispering, “Oh God, Mandy, you feel so good. You’re so
tight.” I kissed her neck, her back then I gently. I tried to keep
still so I wouldn’t cum. After a moment I pulled out a bit. I then
buried my cock again all the way into her again but I made sure to
pause often. I didn’t want to get a rhythm going. If I did, I’d cum
in 5 seconds, no doubt about it.
“Damnit.” I cursed softly, feeling my cum rising.
“What?” she asked.
“I’m so close. I’ve gotta pull out.”
“OK.”
I pulled out gently and slowly, for my sake, not hers. “I need a
minute,” I said. “Baseball, nuns, old women, george bush,” I
said rapidly. “nuns nuns nuns, old women,” again.
Amanda giggled.
After about a minute I looked at my cock, a few inches from her ass.
“OK, babe. It’s time. The nuns did the trick. I’m good to go.”
I aimed my cock head at her ass and pressed forward. I pressed
a bit harder. Her ass gave way and the head of my cock disappeared
up into her rectum. I could feel her tensing up a bit, but so what.
If she didn’t complain then no harm, no foul.
I was good and lubed and ready to go. I figured I didn’t have much
time before I came so I didn’t take it quite as slowly as maybe she
would have liked. I gently but firmly pushed deeper into her ass. I
just gently but firmly shoved my entire 7 inches into her rectum.
She grunted, but again, said nothing. I looked down. My cock was
buried to the quick in her ass. “This won’t take long, amanda” I
said. I took a firm grasp on her hips with both hands and pulled half
way out. My cock had taken on a shit brown sheen and the smell
of her shit again wafted, this time more strongly combined with
that sex smell. That fragrance was now forever locked in my
memory, and even now when I recall that smell my mind’s eye
clearly sees my cock half buried in her ass.
I shoved it all the way back into her, moved back, in, back and in
maybe 5 more times before I felt the pressure build to an unbearable
level. I thrust into her as hard as I could.
Amanda grunted. “Ow,” she said but I was beyond caring. I was
buried up to the hilt in her and I pressed forward as hard and
deep as I could.
“Gahhhh” I gasped, filling her ass with my cum. This was as good,
maybe better, than the very firs time I’d had sex in the back seat
of my car at 17. I felt like I was cuming over and over again.
I stopped breathing, my vision started to darken, but finally
I could feel the last of my cum pouring into her ass. Unforgettable.
I folded over here, again, for the last time. I kissed her shoulder,
fondled a tit with one hand while rubbing her pussy with my other
hand. I pushed a finger into her pussy. “Oh god, ‘manda. Oh god.”
My cock was still hard in her ass and I know I could have gone again
but it wasn’t going to play out that way.
She made a little twitching motion with her body. She didn’t say
anything but I took the cue and gently pulled out of her ass. I
watched as my cock plopped out and her ass slowly winked shut.
As soon as I was out of her she got out of the bed. There was
no anger or fear, just a matter of fact emotion, like she’d just
gotten out of the shower or off the toilet.
“I’m gonna go clean up she said,” grabbing her clothes and heading to
the bathroom. There was no real emotion in her voice as she
left. She was not hiding disgust or fear or joy, just ‘done’.
I rolled over on my back and stayed where I was for a minute just
breathing. Finally I got my clothes, went into the master bath and
used wet paper towels to clean her shit off my cock and balls. I
heard the shower start up in the other bathroom and thought it a good
idea.
After my quick shower I headed down stairs. Her shower was still
running. Fifteen minutes later she came down the stairs, dressed and
looking fine. “You ok?” I asked?
“yea” she replied, grabbing and opening her laptop. She surfed the
web and I went back in my office to try and get some work done.
Well, that was 4 months ago. I still pick her up from school
sometimes, and bring her to our house. Neither of us has mentioned
the incident and obviously she did not tell her mother or my wife.
She just did me a favor, letting me fuck her ass. Thanks ‘manda!