Let me start off this story by saying that I am by no means any kind of
stud. Frankly, I'm at the opposite end of the spectrum, a nerd. Remember
that nerd movie a few decades ago? Yep, that's me, more interested in
computers and grades then being humiliated by the girls at my high
school. I'm barely five foot seven, with average features. Oh sure, I'm
very interested in the opposite sex, but none of them seem to
reciprocate the attention.
I had just turned 18, my senior year, and I was in the school library
studying when I heard someone sit down across from me. I looked up to
see the head cheerleader Jennifer sitting there. My mouth went dry as I
looked at one of the prettiest girls in my high school sitting less than
three feet away from me. She was blonde, blue eyes, a trim hourglass
figure, and the object of more than one randy story. Rumor was that she
had gone down on half the football team, and her 'rewards' for good play
on the field were much speculated about. I didn't say a word, since I
had no idea why she was sitting there.
"Hello, Gerald." I nodded dumbly. "Listen, I need some help with my science project. Would you be willing to help me out?"
I nodded, barely squeaking out the words, "Okay."
"Great! Come to my house Saturday night. Here's the address." She pushed
a slip of paper across the table at me. "Be there about 7PM, okay?
Thanks! Bye!"
She got up and walked away. I stared after her, wondering why a
beautiful girl like Jennifer would want me to help her out when there
were other students that would be beating down her door to do so. Of
course within the hour I was fantasizing that this was a coded way for
her to tell me that she liked me, and that maybe there would even be a
date or more involved. Maybe this was like one of those sappy novels
where the frog would get the princess!
On Saturday I got all dressed up and my mother drove me over there. Yes,
I know how that sounds, but that was the deal. My father had run out on
us years ago, and there was no way my mother could afford to put me on
her insurance. We barely made ends meet with the job she did have, and
only the fact that I had a full scholarship waiting for me at college
was allowing me to go.
I got to Jennifer's house on time and there was a note on the front door
telling me to go around back. I walked around back to see a nice patio
with wrought iron furniture, with a spreading oak tree casting a deep
shadow in the center of the yard. The yard was dark, with the outdoor
lights off. Jennifer was under the oak tree, and when she saw me waved
me over.
Just as I got under the tree, I felt this liquid cascade over me, then
something else drop on top of me. The outdoor lights flashed on, and I
looked down to find myself covered in chocolate syrup and feathers! I
looked up to see the cheerleaders, sitting up in the tree branches
laughing at me, and then I heard in front of me Jennifer say, "April
Fools!" I had totally forgotten it was April Fool's Day!
There was a tradition at my school that a random senior would be
publicly humiliated each April 1'st. There was no real reason for it, it
was just one of those stupid senior traditions like senior skip day or
skinny dipping in some public place or an annual beer bust on a river
somewhere. Naturally I had heard about it, but I was obviously never
part of it. My normal social isolation would make sure of that.
A flash went off, and I knew that my humiliation would soon be on social
media for the whole school to see. The girls were starting to drop out
of the tree now, and various jokes and insults being flung my way, when I
suddenly heard a female yell, "What in the hell is going on here!"
I heard Jennifer call, "Oh, shit! It's my Mom and she's pissed! Let's
get out of here!" Girls were racing for the back fence and soon they
were gone, leaving me dripping syrup and surrounded by feathers.
I turned to see Jennifer's mom walking over to me, high heels clicking
against the patio stones. She was beautiful! She had curly brunette
hair, pearl earrings and a pearl necklace above a blue dress. Her dress
was cinched around the waist by a thin white belt with gold buckle,
ending a few inches above the knees. Her perfect legs were encased in
nylons, and were accented by the three inch stiletto heels she wore. She
was only a few inches taller than me, and what looked like an
impressive décolletage strained against the V-shaped top of the dress,
and her hips were nicely accented. Her makeup was perfect as well, her
mouth open in an 'O' as she hurried over.
"Oh my God, what happened!? Did my daughter do this to you?"
"Her and her friends, Ma'am. I guess they picked me for the traditional
April Fool's Day prank." Unlike girls my own age, I never had had a
problem dealing with adults, even beautiful adult women such as this
one. I guess I had never thought of them as being on the same level as
me.
"Well, they are going to pay dearly for this!" I could hear the anger in her voice.
"Please don't, Mrs. Owens. It'll only make my life worse. She can come
up with a dozen different ways to pay me back at school."
She looked at me in sympathy. "I know. I guess, despite all the warnings
about bullying, high school hasn't changed all that much since I went.
What's your name? I know I've seen you at the school before."
"Gerald."
"Okay, Gerald, let's at least get you inside and cleaned up." She walked
me across to the house to a closed door, asked me to wait, went inside
and within a minute opened the door that led into the mudroom. "Come
inside and strip off. I'll get a towel and you can use the guest
bathroom to shower."
"Thank you, Mrs. Owens."
I carefully took the clothes off, putting them into the mud sink. I had
just taken off my underwear when Mrs. Owens came in, "Here's your
towel... - oh, my." I flushed with embarrassment and tried to cover up
my penis, which really didn't help, and I noticed Mrs. Owens eyes were
riveted on it. While I may be a nerd without experience, that doesn't
mean I don't have a suitable set of equipment for when the time did
come, and it was obvious by the look in her eyes that she was rather
impressed with what she saw. She flushed herself a little, then dropped
the towel on the floor and abruptly went out without saying anything
else, and I picked it up and put it around myself.
The next moment she knocked, and after I told her to come in, she came
in and looked at me with a strange expression on her face. "Why would
Jennifer choose you to play a prank on, Gerald?"
"I've always been picked on and teased, Mrs. Owens. Most people think I'm a nerd."
"You don't even have a girlfriend?"
"No. To be honest with you, I've always been a little afraid of girls."
"Gerald, if they saw what you were packing that would change quickly!"
"Ma'am?"
I saw how she was looking at me and suddenly my entire perspective
changed. I smelled Mrs. Owens perfume, a light floral fragrance, and I
noticed that she was bent over a little, giving me a marvelous view of
her cleavage. For the first time I saw her as a woman, not a mother, and
my penis recognized that. It began to tent the towel, and I saw her
swallow. "Let's get you to the shower, shall we?"
She led the way across the family room to what looked like an in-law
suite. It was nicely decorated with an antique four poster queen sized
bed, along with some other heavy oak furniture. The bathroom was rather
large, with a large shower along with toilet cubicle.
"There's soap and shampoo in the shower, Gerald. You can use the towel I
gave you to dry off. There's a robe hanging behind the door. Call me
when you're ready." She closed the door gently and I soon had the shower
figured out and was getting clean. I was just scooping the last of the
feathers off the shower floor and putting them in a trashcan when
Jennifer's mom came in. "Gerald! You didn't have to do that!"
I turned around and there she was in the doorway, wearing a pleased
expression on her face. "Aren't you the gentleman! I appreciate you
taking care of that."
I got up off the floor and tightened the robe around me. "Well, I
appreciate you letting me shower and get cleaned up. It was very nice of
you."
"It's the least I could do after what my daughter and her so-called
friends put you through. To think, Jennifer is supposed to be graduating
in a few months and she's playing foolish pranks like this." She stood
there, thinking, this mature, lush woman, who looked so classy and
elegant, and her beauty and desirability made a funny feeling come over
me. It's the only reason I can think of that gave me the courage to say
what I said next.
"Well, I'm just wish she was as classy a woman as you are."
Mrs. Owens blushed. "Why Gerald! That's the nicest thing anyone's said
to me in quite a while. Aren't you sweet! You better be careful, I might
get the wrong idea and think that you were flirting with this old
woman."
I was starting to get a hard on as I looked over her sensuous body, and
that strange feeling was strong within me. I could feel my heart
pounding in my ears as I took a step closer to her, and dared to say,
"Well, you're so beautiful I'd be a fool not to flirt with you. And I
can assure you that I am no fool."
She didn't back away, she didn't get mad, she just looked at me with
those dark eyes, now smoldering with some inner fire. She said quietly,
"No, I don't think you are. But I do think that you're just a little
young for me. You don't even know how old I am."
"If you say older then forty I'll call you a liar."
She smiled again. "Well, you definitely know how to make a woman feel
special, but I saw forty almost six years ago. What do you think about
that?"
Somehow we had gotten close enough that I was almost standing next to
her. "I think that age is a number, and it's how we feel that determines
how old we really are. How old do you feel right now?"
My cock was raging hard, and I gasped as I felt her hand with her
manicured white fingernails brush against it, poking out of the robe.
"Young enough not to care about doing this." She untied the strap and
the robe dropped open, revealing my erection. She took one hand and
slowly began to jack my cock, taking it in her hand and running her hand
back and forth, with me watching those fingernails go up and down.
"Oh, Mrs. Owens, that feels so good."
She smiled. "It's supposed to, and I think you can call me Karen." She
jacked me harder. "Have you ever made love to a woman before?"
"No."
"Well, I think we have enough time for me to give you a lesson. My
husband won't be home for hours, he's at some damn business function,
and Jennifer won't be home until after midnight."
I could feel my orgasm building. "Karen, I'm going to come!"
"Do it!" In another second the first orgasm I'd ever had with a woman
exploded out of me and covered her hand with my cum. It felt like I had
run a marathon, and I slumped down some. She smiled, "Well, no surprise
there. Now that we have that out of the way, let's get serious." She
walked over and turned the lights off then walked to the bathroom where I
heard the sink running. "Why don't you pull the covers back?" I
hurriedly did as she told.
She came out of the bathroom and stood there, almost posing for me.
"Well, if I'm going to be your first, I better teach you a few things.
Let's see how you kiss me." I took her in my arms and kissed those
beautiful red lips, tasting the cream of her lipstick. Our mouths moved
on each other, then her mouth opened and her tongue came into mine. I
knew at least the idea of French kissing, and I promptly returned the
favor. We stood there for a few moments, trading deep kisses, and I
began to run my hands up and down her back, eventually daring to cup
that beautiful, tight ass.
She finally broke her mouth away, although we remained in each other's
arms. "Well, I must say you certainly know how to kiss a girl! Are you
sure you've never done this before?"
"No, but I have read about it and watched videos."
She stepped back and turned around. "Unzip my dress." I found the tiny
zipper and slowly pulled it down, exposing her bra strap and ending just
above her panties. Her skin was smooth and tanned, without a hint of
cellulitis, and looked like it belonged on a much younger girl. I slowly
ran my hands up her back, and I felt her shiver under my touch. "Well,
you certainly have the right ideas!" She turned around, letting the
dress slip to the ground, and I saw her exposed.
She was wearing plain white lingerie, a white bra that strained to hold
her large breasts. They were round, about the size of cantaloupes, and
the bra held them high and proud on her chest. Both nipples were
pointing out, and her areolas were brown, much darker then the white
skin. She had pronounced tan lines from a bikini. Her stomach was flat
and smooth, the result of aerobics I'd later learn. Her white panties
were rather standard, but I could see the damp spot on them behind which
was her Venus mound. Her pantyhose were nylon, thigh highs. She saw my
stare and smiled softly. "It's obvious this is the first time you've
seen a grown woman almost naked."
"Oh My God, Mrs. Owens, you're beautiful!"
She blushed a little. "It's nice to know I can still turn someone on. My
husband stopped looking at me like that a long time ago. And it's
Karen, remember?" She waggled one white fingernail at me.
"You ready for the next step? Looks like part of you is!" pointing at my
dick, already starting to recover. "I do love young men and young
cocks, Gerald!" She did a slow pirouette, then stopped with her back to
me. "Take my bra off."
My fingers were fumbling with the small hooks that close to a female's
naked flesh, and it was a wonder that I got any of them loose, but
eventually I did. Mrs. Owens let the bra fall to the floor, and then she
sat on the bed, shaking her now loose titties at me. "Well, what do you
think?"
They had now relaxed, drooping towards the floor, but they were still
firm. The nipples were rigid, and I saw small bumps surrounding each
nipple. They were fat, about the size of the end of my little finger.
"Come over here Gerald, and let me show you how to pleasure a woman's
breasts." I took a long step and she took my hands, placing one on each
breast, and I could feel those hard nipples poking into my palms. "Rub
them gently until she tells you to either make it harder or softer. Work
on each one, using both hands. Her nipple is very sensitive. She may
like it hard or soft there as well." I went to work on each one,
massaging that soft tit flesh, letting her moans of encouragement direct
me. Then I reached down and took a nipple in my mouth, sucking on it
and kissing and licking it. She liked it when I lightly bit on it,
squealing with delight and encouraging me to continue. I made sure to
pay attention to both of them, and I felt her hand come up and begin to
stroke my cock.
"Oh, Gerald, you're doing so well. You're making me so horny for you,
sweetheart. Let's move to the next lesson. This can make or break you
with a woman, sweetheart; eating her pussy. Kneel down on the floor.
Here, use this pillow." I kneeled down, my face level with those magical
white panties. "Go ahead and take them off." I reached up, feeling more
confident, and gently pulled them towards me while she lifted her
buttocks, allowing them to slide off. Her pussy was already exposed and
wet.
"Now, use your fingers to explore it and rub it gently." I promptly
touched a woman's vagina for the first time. Instantly my fingers were
soaked in her juices. I rubbed all over it, sending my fingers where she
pointed, finding a woman's clit for the first time and rubbing on it.
She moaned and squealed with pleasure, repeating endlessly "yes - Yes,
Oh baby Yes - Yes" again and again. I then leaned in and licked it,
using my tongue to explore it's crevices, licking and nibbling on her
clit, using a finger to fuck her gently while I stimulated her clitoris.
"Yes, baby, right there. Keep going - oh my God, I'm - I'm - Oh God
Yes!!!!" Suddenly I felt her clench up, and she let out a mighty groan,
and I felt her entire pussy vibrate and her body shake. Her face was
twisted in pleasure.
Mrs. Owens took a few deep breaths. "Oh, Gerald, that was amazing."
"Did I actually make you have an orgasm?"
"Yes you did, sweetheart, and it was one of the best I've had in a long
time. I bet your cock is hurting pretty bad right now, isn't it?"
"God, yes."
"Well, then it's time for the final lesson, dear. Get up here and put
that massive cock of yours in my pussy. Oh God, Gerald, I want you so
bad!" Mrs. Owens scooted back on the bed, her head resting on the
pillows, her beautiful legs, still encased in the nylons with heels,
spread wide. "Shove that cock in me, honey. I need it so badly, give it
to me!" I awkwardly climbed in between her legs, and she helped guide my
cock with her hand to her pussy. She was so wet it slid right in, and
instinct took over then, and I shoved it as far as I could into her.
Her pussy felt like a warm, wet glove on my aching dick, and it felt so
good sliding back and forth in and out of her. She cried out in
pleasure. "God, I love it. It's so deep and hard. Oh Fuck me Gerald -
fuck this old married woman with that young cock of yours - make me come
again - fuck me - fuck me - Oh God don't stop fucking me!" My body was
beyond my control at that point as I began hammering her, slamming it
into her again and again, pushing it as deep as I could. I was so
excited that I could feel another orgasm building,
"Oh Karen, I'm going to come again!"
"Yes, baby, give it to me. Give me that cum. Put it deep inside of me. Don't you dare stop!"
With a growl I came again, blowing a load of seed deep inside her cunt,
and I felt her pussy clench around my cock as she came as well. I
collapsed on top of her while she put her arms around me, hugging me and
kissing me on my neck.
"Oh, sweetheart, you get an A for that lesson. You're a natural, baby." I
felt my cock soften and slip out of her pussy. Her legs were wrapped
tight around me, and we kissed slowly and deeply. We laid like that for a
long moment, and just when I felt myself drifting off, Karen moved.
"Baby, as much as I'd love to spend the next few hours in your arms,
neither one of us can afford to fall asleep. Let's get up." Reluctantly
we got up from the bed, and Mrs. Owens gathered up the stained sheets
and cover and toted them into the laundry room. "I'll wash these real
quick. Wouldn't do for my husband to find our homework, now would it?"
She winked at me seductively. My clothes had already gone through the
wash, and she now put them in the dryer.
We spent the next hour waiting for them to dry getting to know each
other. I found out that her husband had been neglecting her for years,
and she suspected him of having multiple affairs, although she could
never prove it. She was also fully aware of her daughter's reputation
around school, "apple doesn't fall far from the tree, does it?"
referring to her husband. She also said that the only reason she stayed
with him was the expense and trauma of a divorce. She said that I was
the first time she had strayed outside her marriage. "Sweetheart, what
you did for me was priceless. I regret nothing. Don't worry, I'll take
care of Jennifer for you."
She ran me home after my clothes were dry, after getting my cell phone
number and giving me hers. She told me that we'd be continuing our
lessons very soon, and that amazing evening drew to a close.
Monday at school there was no mention of the April Fool's prank, in fact
nothing had popped up on social media at all about it. I was shocked,
frankly I thought they had filmed it live and it was on one of those
sites, but apparently not. I was walking down the hallway when Jennifer
came up behind me and grabbed me. shoving me into a small alcove.
"Is it true?"
Somehow I was no longer nervous around this girl. In fact several people
had mentioned a new found confidence I had. "Is what true?"
She looked around, seeing no one listening, even so she lowered her voice. "That you and my mother got it on Saturday night?"
"A gentleman never kisses and tells."
She glared at me. "Well, you may not, but my mother sure does. And she
let me know that if I or my friends let one of those pictures or videos
show up on the Internet, she's post her own! Do you realize what that
would do to my Daddy and me? She says I better leave you alone Gerald,
so consider yourself safe for now. But you stay away from my mother!"
I pushed past her and went back out in the hallway. Turning, I looked at
her. "Is that before or after Karen and I's next date?" Her expression
of rage was a fitting end to a very interesting April Fool's Day!

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