The Chaperone Blues
Chapters : 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8
Author's Comment: Life can be a time when everything is pretty much routine, and you've figured out pretty much what you think the world is like and...what you're like. And then something comes along to shake that world view up and everything just goes to hell in a hand basket. That's what this story tries to catch the flavor of.
Claire Richardson was excited as she boarded the school bus. She didn't
take the time to examine that feeling, even though she was thirty-three
years old and was on her way to a high school football tournament. She
just enjoyed the thrills that were coursing through her body as she
bounced up the steps and entered a tiny world of controlled chaos. The
noise hit her like a falling wall as she turned the corner to face
fifty-some-odd students, all of whom seemed to be shouting at the top
of their lungs. Most of them were boys, a few of whom she knew because
her son, Bobby, had brought them to the house for one meal or another,
or because they had dated her daughter, Lori.
No one seemed to notice her at first, though, whether they knew her or
not. The boys were thinking about the upcoming games. The girls were
clustered in little groups that cheerleaders always seemed to sort
themselves into. They weren't exactly cliques, because the girls were a
team of sorts too, but they had natural tendencies to hang with the
other girls who were most like them.
Had Claire stopped to examine the feelings coursing through her body,
she might have recognized them as being remarkably like sexual
feelings. She might have noticed that her panties were a little damp
and that her nipples had spiked through the cream colored silk blouse
she should have known better than to wear to a sporting event weekend.
But she hadn't had time to change after work. She was dressed for
business—a charcoal wool skirt clinging to her hips, making
the jut of her breasts seem larger than they actually were.
She wasn't ignored for long.
Had Claire examined the faces of all those teenagers, she might have
noticed that a lot of the boys' eyes lingered on her as she waded
slowly through the crowd, lugging her bag behind her, looking for her
own children. Or she might have noticed the frowns of some of the girls
as THEY noticed who the boys were looking at with that look in their
eyes that made the girls get wary and careful.
But it had been a long time since Claire had been in an atmosphere
charged so heavily with teen hormones and the spirit of impending
"combat," and she'd forgotten how it affected a person. She'd shut away
her own feelings for the last ten years, after her husband had said
that two screaming kids wasn't what he had in mind for his future.
Back when Claire was in high school, she had fought off all the boys,
looking to her future and wanting to save her virginity for the man she
just knew would sweep her off her feet. It was made that much more
difficult by the fact that she was a cheerleader. She resisted men in
college too, until the team won a big game and a frat on campus threw
them a victory party. She had perhaps one too many wine coolers that
The star of the game was a boy named Denny who had convinced
her to give him a victory kiss. Denny's kisses had set her on fire. Her
resolve to stay a virgin seeped away like the fluid in her wine cooler
when it was knocked over as he pulled her up. The next thing she knew,
she was lying on a bed with him in a darkened room.
And it HAD been glorious. She hadn't had any idea how wonderful a stiff
penis would feel stroking the walls of her vagina and scraping along
her enflamed clit. Her almost instant addiction to that feeling had led
to her lying naked under him time and again. He’d knocked her
up while they were both sophomores in college, and she'd agreed to
marry him even though she liked several other boys more. She'd wanted
to believe they were in love and nothing either of their parents had
said against the marriage had sunk in.
And, truth be told, things hadn't been so bad at first. But when he'd
gotten her pregnant again within a year, and the money troubles had
started, and he'd had to take two jobs, and couldn't party with his
buddies, he'd thrown in the towel. Claire had been left to finish
college and raise Lori and Bobby by herself, with a little help from
her parents now and then.
So SHE was the one who had to take three jobs and forego dating or any
social relationships outside her jobs. And her determination had
finally led her to find something she was good at. She'd taken an entry
level job at a bank and had eventually worked her way up to being the
manager of the loan department. Her single-minded devotion to her two
children had resulted in success in the business world and a
comfortable living for them all. But it was at the cost of her social
life, as she deflected the well meaning...and some
not-so-well-meaning…advances of the men she ran into in that
She knew she was beautiful and desirable. She cultivated that
appearance, because it had helped her succeed in the banking business.
She was aware that she was attractive and that people—both
men and women—saw her as a sexual being, but she viewed that
side of her as a tool, used only to seal a deal and not to pursue
personal enjoyment. Her fingers did for her what she thought her body
needed occasionally. She had grown so used to the convenience of being
able to grab a quick orgasm now and then that she had unconsciously
held herself aloof from any relationships with a man that might have
been vastly more satisfying.
It was almost an accident that she’d met Coach Bondurant, or
"Chuck" as he demanded she call him. She knew he was her son's football
coach, because Bobby talked about him like he was a legend. So, when he
applied for a loan to buy a house in Hillsdale, where she lived, and
his file was brought to her for approval, she’d decided to
meet him in person.
That he was five years younger than she was something she noticed but
didn't dwell on. He had a good job and, as far as she could tell, was
good at that job, so she had approved the loan. Having been turned down
by two other banks, his thanks had been effusive, and her casual, "You
coach my son Bobby," had generated praise for her as a mother.
That was what made her give him another look. Being a mother was her
pride and joy.
And that look had turned into a chat, and that chat had resulted in his
solicitation for her to be a sponsor for the regional championships
that the team was going to attend. When he explained that the team,
along with their supporting cheerleaders, would be staying in a motel
for several nights, and that adults were needed to chaperone them, and
that the cheerleading coach was eight months pregnant and couldn't go,
and that he was having a hard time getting a female to agree to come
along for the ride, Claire made one of those snap decisions that she
had learned to trust.
She agreed to do it.
There had been little time to plan or think about things before it was
time to pack her bag and get in her Lexus to drive to the school. Bobby
and Lori had already made arrangements and were already gone as she
backed out of the driveway and drove to Hillsdale High School. She was
thinking about trips SHE had taken as a cheerleader almost twenty years
ago. She had seen what some of the cheerleaders did with the players
when adults weren't watching and she knew well what football players
were like. "Denny the Derailer," her former husband, was a linebacker
who had battered down her defenses as effectively as he battered down
the defenses around the quarterbacks he sacked.
She hadn't thought about Denny for a long time, moving on with her
life. He dropped a card to the kids once in a while, but neither of
them had ever seen him once they got old enough to remember him. They
knew who he was, but had no real feeling for him. The three of
them—Claire and her two children—had poured all of
their affection into their little family.
Maybe it was the memory of that wild night when she lost her
virginity...and got pregnant with Bobby…that re-awoke the
emotions coursing through her as she boarded the bus that day. If so,
she wasn't aware that she was excited in the same way she'd been
excited that fateful night so long ago. All she knew was that she was
excited and she was having fun BEING excited. There hadn't been much
excitement in her life for a long time.
At any rate, as she bumped and jostled her way down the aisle of the
bus, pushing past students, looking for her children, she looked like
she felt. She was a woman who made the boys turn their heads toward
her, admiring the thrust of her breasts through the silk blouse,
including the prominent nipples that pushed through her thin Victoria's
She saw Bobby and Lori sitting together in a seat toward the back of
the bus and an even warmer feeling raced through her. They were talking
to each other animatedly, obviously fond of each other, and that made
her feel good. So many brothers and sisters fought constantly, but that
was something she didn't have to put up with.
And there were other students involved with them, leaning over the back
of the seat in front of them or standing beside them. They were
obviously popular. It made her feel successful as a parent.
Lori saw her first and smiled widely as she waved. She stood up and
called out, "Hi Mom!"
As Lorie's voice pierced the cacophony of sound, teenagers looked to
see Claire making her way slowly toward them. She heard one boy say,
"That's your mom? Wow!"
That simple comment, made by a boy young enough to be her son, caused
Claire to blush. The compliment that from an older man would have been
shrugged off as normal jarred her into thinking about her
attractiveness in a different way than she usually did. There was a
strange mix of emotions that flooded through her as she thought briefly
about the irony of the fact that a mere boy's positive appraisal of her
appearance meant something to her, while the same thing from a man
would have been deflected like a poorly thrown pass.
Claire's eyes darted to her daughter's face, which was showing a mix of
surprise and embarrassment. Lori was looking at her mother's breasts.
Claire looked down and saw immediately what Lori was embarrassed about.
Claire had very prominent nipples most of the time, and they were
advertising their presence plainly.
The woman in her was proud of them. The mother in her immediately
recognized that her daughter would think she was improperly dressed.
Never mind the fact that Lori had inherited her mother's nipples and
that she often showed hers off too. What Lori thought was fine for
herself did not apply to her mother.
"Sorry," said Claire to her daughter. She looked at Bobby who was also
staring at her chest interestedly. There wasn't anything she could do
about it now. If she covered the tips of her breasts it would only draw
more attention to them and she was used to men staring, so she decided
to tough it out. "I'll change when we get there," she said.
"I would hope so," said Lori, looking around. She counted at least five
boys who were staring at her mother. The look on their faces was just
like when they stared at her or one of the other girls. She was aware
on a cerebral level that an "older woman" could be a turn on for a
younger man, and she knew her mother was beautiful, but the emotions
she felt at that moment were distinctly uncomfortable. It was
odd to think of her mother as potential competition. At the same time,
with the certainty of all young women, Lori was sure that she was more
desirable than any older woman could be. "Never mind. I'm
being silly. You want to sit with us?"
That sent another shot of warmth through Claire as her children, rather
than being standoffish that their mother was there, welcomed her. There
wasn't any place nearby to put her bag, but a boy offered to put it in
the back with the other luggage, which was piled high on the last two
rows of seats.
By the time she sat down, Claire Richardson was an overflowing jumble
of emotions, almost all of them pleasurable. She was immediately
surrounded by boys who, for some reason, wanted to talk to her
children. It made her feel young again.
At least until all the kids started calling her "Mrs. Richardson." That
brought her back to earth pretty quickly. But even then it was obvious
she was being accepted by the kids, and that made her feel almost as
She had barely settled in, squeezing Bobby and Lori up against the
window of the bus, when Coach Bondurant got on the bus. He called the
roll and, when he had decided everyone who was supposed to be there
was, he introduced her.
"Mrs. Richardson has kindly agreed to chaperone this trip," he
announced. "I know you won't give her any hassles ... RIGHT?!" A chorus
of “RIGHT” was yelled out in that tone of voice
that kids all use to let adults know they've said something stupid,
even though they are expected to agree with it. Coach Bondurant went
on. "AND, just so we all understand each other, Mrs. Richardson was a
cheerleader when she was in high school, so she knows all the tricks.
Don't think you're going to be able to game her, because you aren't."
Claire wanted to giggle when there was a softer chorus of sighs that
clearly indicated some hopes had been dashed, both male and female. The
coach waved her forward and, as she left, she heard a boy whisper
behind her. "Man Bobby, your mother is HOT!"
There was a smack, as of a hand on an arm perhaps, and Lori yipped,
"Shut UP Thomas!"
Claire just grinned and went up to talk with the Coach. He had saved a
seat for them, it turned out, because he’d assumed she'd want
to sit with him rather than the students. As she sat down she saw that
his eyes were fastened firmly where every other male's eyes had been.
He looked up and caught her...catching him.
He blushed. "Sorry," he said. Then he smiled. "But I'm normal I guess.
I hope you won't hold it against me."
He sounded so sincere that she decided not to react as she normally
would have reacted. "I suppose I could give you another chance," she
said. "I didn't have time to change into something more appropriate."
"Thank you," he said and, to her surprise, he sounded like he meant it.
"Sit down and I'll show you the schedule and go over the expectations
of the school board.”
It never occurred to Claire that his thanks might be for more than just
... another chance.
He hauled out a thick three ring binder and flipped it open to a list
of rules and policies that the board expected the team to follow on
trips like this one. He was all business now.
"You can read over these in the room tonight, or as we drive if you
want," he said.
Then he launched into explaining a matrix of lines with names beside
them of all the schools that would be playing at the tournament,
explaining how losses and wins affected lines that didn't have anything
beside them. Claire began to remember how things worked and soon they
were chatting about their chances of advancing and his tactical plans.
Claire loved football. It was one of the few sporting events she
followed and watched on TV. That her children were like-minded made
their weekends full of sports, both inside and out of the house. The
bus started off and the noise level abated somewhat as kids began to
cluster into smaller groups and have their own discussions.
"So, other than enforcing the rules, what am I supposed to do?" asked
The bus was bounding along on an uneven road now and she saw Chuck's
eyes drawn again and again to what she felt bouncing up and down on her
chest. To his credit he tore his eyes away from her breasts again and
again, looking at the book or at her face. She thought his attempts to
make good his "second chance" were cute. He appeared to be trying to be
a gentleman, at least.
"Well, really, it mostly amounts to making sure the kids don't let
their emotions get away from them...off the field," he said. "I mean
they're kids and they do what kids have always done if they get the
chance." His eyes strayed to her bouncing breasts once again.
Claire laughed. "Well, if they're in separate rooms that shouldn't be
Chuck didn't smile. "The boys know that breaking curfew will get them
benched, but the girls sometimes don't care about that and try to sneak
into the boys' rooms. And, of course, the boys who AREN'T involved
won't rat them out to the coach, so we have to keep our eyes peeled."
"Are there really that many problems?" asked Claire.
"You were a cheerleader. Were there problems back then?" asked Chuck,
not knowing her history, but assuming that such a beautiful and
successful woman would not have any skeletons in the closet.
Her response was confusing to him. First she took in a breath and
didn't breathe it back out. Then she blushed. Then her mouth opened and
closed several times. Finally she stammered, "I see what you mean." It
left him wondering about her past, but he didn't ask any questions.
"We'll try to put their rooms as far from each other as we can," he
said. “Sometimes we don't have much choice in the matter."
The rest of the trip—several hours—was spent in
light conversation, during which both adults developed a respect for
each other that didn't surprise them...and an attraction that did.
The coach's words were prophetic, in ways he couldn't have dreamed. It
turned out that all the other schools had arrived already. Several had
taken more rooms than they had originally booked and, based on Chuck's
preliminary room diagram, they were two rooms short at check-in. The
motel manager was apologetic, blaming his staff for overbooking the
motel. He called three other places in town, but if they went that
route the team would be scattered all over the place. Fire codes
prohibited more than a set number of people being lodged in a room and,
as they pored over the paper map the manager produced, it became clear
that there would be one female and one male student left over after all
the rooms were assigned. And that didn't take into account either Chuck
Oddly, the solution was offered by Lori, who came to the desk after
being chosen by the team to find out why they were all standing around.
When she found out the problem she said simply, "Why don't we put Bobby
and me and you and Coach in one room?"
Chuck looked at Claire and she stared back. It wasn't perfect, but it
was a lot better than either of them had come up with. It was agreed
that it was the best fix to the problem.
The manager was all smiles then, until it was determined that, in one
of the rooms, there was a bed missing. Investigation revealed that one
bed had been broken the night before, so badly that it couldn't be used
any longer, and the maintenance staff had removed it. The remaining bed
was a queen sized bed, but it wouldn't sleep four.
Everybody else was assigned a room and told to return to the bus at a
time specified for supper. In the meantime the manager scurried around,
looking for another bed. He came back looking unsure of how his news
would be received.
"The best I can do is provide a mattress and linens" said the harried
innkeeper. "I realize it would amount to little more than a pallet on
the floor. I'm sorry, but there's nothing else I can do."
"Don't you have a roll-away or something?" asked Claire.
"I'm really sorry, but they're all taken," said the man. It became
obvious that he had put more people in some rooms than the fire code
allowed, but wasn't willing to admit it.
Claire looked at her children and Coach Bondurant. "What do you think?"
she asked helplessly.
Chuck said, "I'll sleep on the floor. It's no big deal."
The manager fidgeted. He made it obvious he had other things to do.
Claire, used to being in charge of things, said, "OK, we'll work it out
somehow. Let's just get in the room before somebody else comes along
and takes it." She gave a dark look at the manager, who just shrugged
"Of course we'll give you a discount," said the manager.
"I would hope so!" barked Claire.
When they got to the room a motel worker was already dragging in the
mattress that would go on the floor. It was only a double.
"We can't fit two people on that!" complained Claire. She remembered
what it had been like in college, when she and Denny had shared such a
bed. Back then it had been romantic, but this was a different situation.
Once again it was Lori who suggested a solution.
"Look, Bobby and I could fit on that. His stinky feet will hang over
probably, but then they won't be under the covers where their smell
will keep me awake." She grinned as her brother gave her a gentle
shove. "There's plenty of room in the big one for two people to sleep
and not run into each other."
Claire wasn't overjoyed about this fix. "Couldn't Bobby and the coach
sleep in the big bed?" she asked.
"Mom," said Lori with exaggerated patience. "You wouldn't be
comfortable sleeping on the floor and you know it. Bobby and I can
share the little bed. Like coach said, it's no big deal."
"But still, you two would have to be right next to each other," said
"That's OK," said Lori. "He's not so bad."
Chuck spoke up. "How about if Bobby, and your mother and I slept in the
queen? That would leave the smaller bed for Lori. Bobby could sleep in
Bobby laughed. "I like you coach, but not that much. I don't think I
could sleep rubbing up against a man. I mean Lori's my sister, but I'd
rather bump into her than a man."
And so it was decided. There would be a male and female in each bed. By
then it was time for supper and they didn't have time to argue about it
anymore. Claire couldn't even think about it as she tried to get
through the pandemonium of feeding in excess of fifty kids, while
busloads of kids from other schools competed for available seats and
By the time the screaming kids piled out in the motel parking lot and
began to straggle toward their rooms, Claire was so tired she didn't
care who she slept with. She and Lori claimed the bathroom first.
Claire sat on the commode while Lori showered and they talked about
things in general. Then Lori dried her hair while Claire stood under
the warm water. That water suddenly started going cold and she had to
shut it off as she got goose bumps all over her body. She got out of
the shower and dried off hastily, putting on the silk pajamas she'd
brought to sleep in, not dreaming she'd have to sleep with anyone.
She looked up to find Lori staring at her. "Aren't you going to wear a
bra to bed?" asked her daughter. Claire looked in the mirror and saw
that she hadn't dried her body all that well and the cold had spiked
her nipples again. They were making two damp points in the thin silk of
"I hate to wear bras to bed," she complained.
"Well Coach will love you in that outfit," said Lori.
"Coach will be gentleman enough to ignore me," said Claire.
"I wouldn't bet on that if I were you," said Lori. "I can't believe my
own mother looks sexy in pajamas!"
Claire looked at Lori, who was wearing a white T shirt and panties.
Claire could see her daughter's dark nipples through the shirt.
"You don't have much room to talk," she said. "You aren't wearing a bra
either, and you don't look so shabby yourself in that. Surely you
aren't going to let coach Bondurant see you in just panties."
"I thought I'd be staying in a room with girls, Mom. I didn't bring
things to wear for bed around men!"
"Well you can't just show a strange man your panties," said the mother
in Claire. "Wait here."
Claire went into the room and asked the two men if either of them had
an extra pair of boxer shorts or gym shorts that Lori could wear. Bobby
dug through his suitcase and pulled out a pair which he threw to his
As far as Claire was concerned, the shorts didn’t help all
that much. Her daughter was growing up and was beautiful.
"You're still going to make their eyes bug out in that outfit," she
Lori laughed. "This old thing?" She giggled some more. "Coach will be
so busy looking at you he won't even notice I'm there."
By the time Lori had helped her dry her hair and pull it back into a
pony tail, Claire's nipples had softened and weren't so pronounced. She
felt much better about going out into the room, where she planned on
getting under the covers as quickly as possible.
She wasn't prepared for the change in temperature between the bathroom,
with its fogged mirror, and the cool of the main room. By the time
she'd taken five steps into the room her nipples were again proudly
Lori was almost correct. When the two women walked into the room, both
men looked at them. Chuck's eyes were, in fact, riveted on Claire,
though he glanced at Lori, too, several times, his eyes looking like he
was at a tennis match. He settled for looking at the ceiling. He and
Bobby had been watching TV. He stayed in his chair and told Bobby to go
on and take his shower.
"There's no hot water left," warned Claire. "It ran out in the middle
of my shower."
The men took it like men and dashed in and then out of the shower
quickly. Both wore gym shorts and T shirts to bed.
It was odd being in bed with another person at all, much less a strange
man. Claire's emotions, which had already been on high alert, built
even more. She couldn't sleep. As she lay there trying not to make any
noise in the semi-dark, her eyes adjusted to the light from the parking
lot coming in through the thin drapes over the motel windows. Her mind
flitted here and there, remembering things. She could feel heat
emanating from Chuck, even though there was a chaste fold of blanket
gathered between them. It took her ten minutes to realize she
It took her ten more minutes to realize she wasn't going to get to
sleep unless she did something about it.
Ever so slowly, she slipped her right hand down her stomach and under
the waistband of her silk pajama bottoms. Her senses were heightened
and anticipation made her tense as she felt the first strands of her
pubes on her fingertips. She almost couldn't suppress a sigh as her
finger split her labia, which were stuck together with the proof of her
excitement, and her fingertip slid onto her engorged clit. She spread
her legs automatically and her right leg bumped Chuck.
Listening, she realized she could hear the smallest
sounds—Chuck’s slow breathing, the rustle of bed
clothes from the makeshift bed her children were in, as they moved in
their sleep, voices from outside somewhere, and the sighing of air as
the wall unit under the window tried to pump warm air into the room.
Hearing nothing that caused her to believe she'd be discovered, Claire
pressed with her index finger on the little bump that was her ticket to
sleep. She rolled her fingertip in a circle, playing with the
protrusion, and felt the thrills shoot through her that always came
when she mauled the little lump of flesh. She went slowly, enjoying the
way her passion built as she played with herself.
She was perhaps halfway to her orgasm when she heard Lori's almost
"Bobby! Not now! Mom's right there!"
Claire froze again. Very slowly she turned her head. Her hair was in
her face and she was afraid to lift her hand from under the covers to
remove it. She could see through one eye the heap of covers that were
her children. It was moving. There was a little sighing moan that was
in a voice too deep to be her daughter's.
"Please?" came Bobby's voice in a whisper.
"You'll wake up Mom," came the whisper of her daughter. "You want her
to know what we do?"
"Nooo," moaned Bobby. "We won't wake her up if we're careful. You know
how hard she sleeps. Pleeease? I'm sooo horny."
What Bobby was referring to was the fact that, most nights, Claire took
a sleeping pill. Her work was demanding on an emotional level, and the
pill ensured that she'd get a good night's sleep to face the next day.
But this night she hadn't taken the pill. She hadn't thought it would
There was silence, broken by the sound of what was most likely a kiss.
It sounded like a long, wet kiss. Claire couldn't believe what she was
hearing. Her own children? Kissing? And quite likely more than that?!
Lori's voice still came in a whisper, but it was a breathy one, as if
she were breathing hard. "Do you have a rubber?"
"In my suitcase," was Bobby's equally breathy reply. "But I can't get
up and get it. It would wake her up for sure," he moaned.
"Mmmmm that feels good," sighed Lori. "But you know we shouldn't do it
without a condom."
"Wouldn't you like something more than just my finger?" he whispered.
"We shouldn't do it without a condom," repeated Lori. Now it was
obvious that she was breathing hard. Claire could hear her deep rapid
breaths in the quiet of the room.
"Just this once?" pleaded Bobby.
"You always say just this once," said Lori.
But Claire could hear in her voice that Lori was going to let her
brother do it. She was going to let her brother slide his stiff young
prick into her teenaged pussy, where it would spurt long sticky ropes
of his potent teenaged sperm into her womb.
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