


Sherry Baby, Will You Cum Tonight

by walterio



Category: First Time
Published: 2011-09-19
Updated: 2011-09-19
Packaged: 2017-04-25 08:37:30
Chapters: 1
Publisher: literotica.com
Story URL: https://www.literotica.com/s/sherry-baby-will-you-cum-tonight
Author URL:
https://www.literotica.com/stories/memberpage.php?uid=429765&page=submissions
Summary: High school senior finally busts his cherry.
Erotica Tags: 18-Year-Old, Anal Sex, Car Sex, Cum Swallowing, His First Time,
Massive Cum Shots, Multiple Partners, Mutual Masturbation, Oral Sex, Sherry
Baby, Will You Cum Tonight
Average Rating: 4.19






        Sherry Baby, Will You Cum Tonight


_Authors Note: I liked this story line submitted in a reader request so I gave
it a shot. The names are fictitious and all characters are at least 18 years
of age._  
  
INTRODUCTION  
  
It was the spring of 1959 and Cliff Walters could not believe that he would
soon graduate from high school. He had played his last high school football
and basketball games and soon baseball would be history as well. Of most
concern to Cliff was that he was still a virgin. Unlike his jock buddies he
still had not gotten laid in high school. His current girlfriend Susan was a
great make out and they petted and played with each other but she would not
let Cliff in her pants. She allowed him to unhook her bra and fondle her tits
and she let him finger her pussy. However he was not allowed to remove her
panties but only pull them to the side to bare her quim. Susan also gave him
hand jobs with his cock and balls exposed through his fly.  
  
In 1959 everything was great; the cars, the music, the dances and the clothes.
Dwight Eisenhower was the President and Rocky Marciano was the heavyweight
boxing champion. Guys hung out under street lamps and sang song hits by a
number of artists including one song wonders. It couldn't have been better
except for Cliff's virginity. He was enlisting in the Marines after graduation
and he did not want to go in as a virgin. Cliff pressed Susan on the sex and
she flipped out. They had a huge fight and broke up at least for a week or
two.  
  
SADIES HAWKINS DANCE  
  
One day after baseball practice Cliff was leaving the locker room and headed
toward the school parking lot when he was approached by a classmate. "Cliff
can I speak with you a second," Sherry Borg addressed him.  
  
"Sure Sherry, what's up?"  
  
"I would like to ask you to the Sadie Hawkins dance?"  
  
Cliff was caught off guard and he was in a pickle. He had assumed that Susan
and he would go to the dance together but she had not asked him. It was an
unwritten rule in school that a boy could not refuse a girl asking him to the
Sadie Hawkins dance. He knew that he had no choice in the matter so he agreed.  
  
"Okay Sherry, I know that I have to accept since Susan didn't ask me. I'll go
with you," Cliff accepted sheepishly.  
  
"Great, I knew that you and Susan were on the outs and I hoped you would say
yes," Sherry beamed.  
  
Sherry turned and walked toward her car in the student parking lot and Cliff
watched her. Sherry was stacked with big tits and a big ass. Her ass was
bigger than Cliff liked on a girl but it least it was round and shapely.
Sherry was one of those 19 year old girls that guys went out with to get all
they could off of her. Her mature size was appealing in high school but she
was destined to be a cow later in life unless she did some drastic with her
life style.  
  
Cliff knew of Sherry's reputation of putting out and he looked on the bright
side of things. Maybe he would get laid after all and not graduate a virgin.
Cliff got in his car and drove home. He would have to tell Susan what happened
and he knew that she would be pissed. Still a rule was a rule and since he
didn't have a date to the dance he had to accept Sherry's invitation. The
dance was in two weeks and it was unlikely that he and Susan would go out
again until after the dance.  
  
Friday night arrived and Cliff picked up Sherry for the dance. Sherry was
staying at her aunt's house that night as her parents had gone to the Poconos
for the weekend. Her aunt instructed Cliff to have Sherry home by midnight.
The dance was more like a sock hop and everyone was dressed casual. Most of
the girls wore poodle skirts and saddle shoes with their hair tied up in a
pony tail. The dance was a blast as everyone danced to their favorite songs.  
  
Cliff had more fun dancing with Sherry than he had expected. She was a good
dancer and loved to jitterbug. The slow dances were great too as Sherry
pressed her full body against Cliff crushing her big tits into his chest. He
had an erection the entire time they danced close together and Sherry
purposely pressed her thigh into his crotch. Cliff actually thought that he
might cum in his pants at one point but he was relieved that he didn't. The
dance was scheduled to end at 11:00 PM but Sherry told Cliff that she wanted
to leave earlier. They left at 10:00 PM and Sherry directed Cliff to a parking
area where they could neck.  
  
Cliff had never been to that particular area for making out as he and Susan
had always parked at another spot. This area was very secluded but there were
already a number of cars with steamed up windows there. Cliff found a good
spot and he turned off his car engine. Sherry was all over him and began
kissing him driving her tongue into his mouth. Cliff's 1956 Chevy had a bench
seat in the front so it was easy for them to maneuver. Cliff ran his hands up
under Sherry's sweater and grabbed her big tits through her bra.  
  
Sherry didn't protest when he unhooked her bra and fondled her naked breasts.
Even though her tits were big they were firm and Cliff liked holding them in
his hands. Her nipples hardened and they felt as stiff as the erasers on the
end of his pencils. He twirled her nipples in his fingers and they seemed as
long as the tip of his little finger. Cliff dropped one hand to Sherry's
thighs and pulled her skirt up her legs. He ran his hand along the bare skin
until he reached her panty covered pussy. He found her panties to be soaking
wet and he slipped his finger under the elastic into her pussy. Sherry groaned
into his mouth when he finger entered her and she mumbled something.  
  
They broke their kiss and Cliff whispered, "What did you say?"  
  
Sherry replied urgently, "Take my panties off!"  
  
Cliff had never removed a girl's panty before as Susan had never let him. He
took a hold of the waistband and pulled then down over Sherry's buttocks and
off her hips. Sherry raised her body making it easier for him as he slipped
them off of her. Cliff tossed the panties on the floor of the car and put his
fingers back in Sherry's pussy. He finger fucked her pussy as she maneuvered
her body so that his fingers were rubbing her g-spot.  
  
"That's it keep you fingers there. Now rub my clit too. Oh yeah, like that,
you got it," Sherry blurted out.  
  
Cliff kept rubbing the hard flesh in her vagina with his fingers and her clit
with his thumb. Sherry's body was out of control as she humped her hand racing
toward her first orgasm. Susan had never behaved like this with Cliff and he
was now totally caught up with Sherry's sexuality. Sherry moaned, groaned and
humped her way to her climax and when it hit it rocked her body. Sherry
grabbed Cliff head and pulled him to her as she yelled for him to hold her.
With his free arm he wrapped it around her and buried his face in her tits. He
began sucking on Sherry's nipple as he continued to finger her pussy.  
  
Sherry lost it and her body gyrated frantically and Cliff held on as tightly
as he could. His hand was drenched with her orgasmic juices and the smell of
sex was rampant in his car. Sherry slowly recovered from her intense orgasm
and as she did she kissed Cliff and thanked him.  
  
"That was wonderful. Now it's your turn," she said as she reached for his belt
buckle.  
  
Cliff sat frozen to the car seat as Sherry unbuckled his belt and unzipped his
fly. Next she pulled his pants down and the outline of his erection was
prominent in his underwear. Sherry reached for his underwear and she pulled
them down to his knees along with his pants. His erect 7" cock slapped against
his belly and Sherry took it in her hand. It was another first for Cliff as he
had never had his pants down in front of a girl. Anytime Susan had jerked him
off he only had his fly unzipped. His cock stood out like a flag pole
displaying his obvious desire. Cliff felt like he would cum any second as
Sherry toyed with his dick. It was clear that Sherry was in complete control.
Sherry pushed Cliff back against the car seat and then she knelt before him on
the floorboard.  
  
You have a nice cock and I am going to enjoy sucking it," Sherry said in a
very sultry tone.  
  
Cliff was speechless as he watched Sherry lower her head and engulf his cock
in her warm sensuous mouth. He gasped as she closed her lips around it and
then began to bob up and down. Sherry deep throated him and he felt her lips
touch his pubic hair as she swallowed his entire cock. No one had ever sucked
his cock before and he almost lost it at that moment. Sherry continued to suck
his cock and she swirled her tongue around and nibbled the head driving Cliff
crazy. Sherry sensed that he was close to blowing his load and she cupped his
tight balls and massaged them as she tightened her mouth around his cock. That
did it and Cliff could feel his cum travel from his balls through his scrotum
as he started to cum.  
  
"Oh shit, here it is. I'm cumming," he screamed but it was more of
announcement than a warning.  
  
Sherry stayed glued to his cock and swallowed every drop of his seed as it
rushed into her mouth. Cliff came in droves and Sherry had to swallow quickly
to keep his seed from running out of her mouth. Cliff could not believe how
Sherry worked his cock and swallowed every drop. He had never expected a blow
job much less have her swallow his cum. Sherry was pleased with his virile
discharge and she knew that he would be hard again in no time so that he could
fuck her. Cliff shot quite a load in her mouth.  
  
Sherry sucked and nibbled and teased Cliff to no end. Finally he begged her to
stop and he slid down onto the car seat to rest and recover. Sherry sat next
to him and turned his face toward hers. She kissed him deeply plunging her
tongue into his mouth allowing him to sample the after taste of cum. Cliff
reached for her and took her in his arms. Cliff fondled her tits, thighs and
ass as they kissed. He could feel himself getting erect again as they cuddled,
petted and kissed. Sherry stroked Cliff's cock until he was hard again and
then she moved to sit on him.  
  
"I got so hot sucking your cock that I need to sit on your dick," Sherry
gasped and quickly added, "I'm safe tonight to its okay to cum in me."  
  
Cliff sat up and aimed his cock at Sherry's pussy. He slid in easily to the
hilt and reveled in the warmth of her cunt. Cliff began to pump his cock in
and out of Sherry's pussy as she bounced up and down on him. Sherry positioned
herself so that her clit was in constant contact with his cock. Cliff began to
pound Sherry's pussy and Sherry humped her hips back at him just as hard. The
two of them fucked each other frantically breathing heavy and grunting and
moaning. Sherry had another orgasm but continued to fuck Cliff toward his.
Sherry lost count of her orgasms before Cliff finally filled her pussy with
his seed. He was glad that she told him that she was safe because he would not
have thought of it and he didn't have any rubbers with him.  
  
Cliff stiffened and then thrust into her each time he felt his cum ejaculate.
Sherry rocked with him and she clenched her cunt muscles squeezing every drop
of cum from his cock. Sherry collapsed on his body as she felt the last surge
of cum leave his cock. Sherry held him tight as he relaxed his body. Cliff had
never felt so good in his life. He couldn't believe his good fortune in
fucking Sherry. It had been an evening of firsts for him.  
  
Sherry rolled off of him and sat next to him. Sherry then she kissed her way
down his chest passed his stomach to his cock. Cliff gasped in surprise when
Sherry took his cock in her mouth and sucked it clean of their combined
juices. Then she moved up his body and kissed him deeply shoving her tongue in
his mouth again. Sherry wanted to be sure that he got to taste both of them
and that he shed any inhibitions that he previously had.  
  
"That's enough for tonight. I need to get back to my aunt's house. Can we get
together tomorrow?" Sherry asked.  
  
"Yeah, I guess sure. What do you want to do?" Cliff replied tentatively.  
  
"Meet me at my house tomorrow at noon. I'll tell my aunt that I'm going to the
mall. Park your car a couple of blocks away and walk to my house," Sherry
explained.  
  
It was clear to Cliff that more sex would be on the agenda and he readily
accepted Sherry's invitation. "Okay, I'll be there at noon."  
  
Cliff and Sherry straightened up in the car while the defroster cleared the
steamy windows. Cliff drove Sherry home to her aunt's house and they arrived
just before midnight. Sherry kissed Cliff goodnight and reminded him about
Saturday. Cliff drove home with the car windows open even though it was cold
as his car reeked of sex. He didn't mind the smell but he didn't want it
lingering overnight. It had been quite a night for Cliff getting his first
blow job and losing his virginity. He felt great and he wondered what Sherry
had in store for him the next day.  
  
MORE FIRSTS FOR CLIFF  
  
Cliff arrived at Sherry's house at noon on Saturday and he had parked his car
several blocks away just as she had told him. When she answered the door Cliff
was momentarily shocked as she was dressed in a bikini like outfit. Sherry
ushered Cliff in the house and he followed her up the stairs to her bedroom.
He stared at her big round shapely ass in the tight terrycloth bottoms as they
ascended the stairs. He felt his loins stir and he was anxious to be naked
with her in her bed.  
  
Once they entered Sherry's room they immediately got undressed as Sherry
directed. She pulled off her terrycloth bra top and pulled down her bottoms.
She stood naked in front of Cliff and he admired her full figure. It was the
first time he had ever seen a girl naked in person and his cock was throbbing.
Sherry smiled at him and then spoke.  
  
"Are you going to undress or what?"  
  
Cliff snapped out of his stupor and quickly removed his clothes. His cock was
stiff and sticking out from his body. "Well I can see that someone is happy to
see me," Sherry teased and then she hopped in bed.  
  
"Have you ever eaten pussy before?" she asked.  
  
"No I haven't," Cliff confessed.  
  
"Well I will teach you," Sherry told him.  
  
Sherry lies back on her bed and spread her legs. Her hands went down to her
pussy and she stroked her quim and opened it for Cliff to see. Cliff just
stared at her in all her beauty lying on the bed. Her dirty-blonde hair spread
across the bed, her big firm tits and hard nipples stuck up in the air and her
voluptuous tanned body was splayed before him. Sherry held her arms open to
him and then guided him to her body as he leaned in toward her.  
  
Sherry coached him through every move of his first cunninglus experience.
Cliff buried his tongue in Sherry's pussy shoving it in as if he was fucking
her. Sherry directed the action and she soon had him nibbling on her clit
while he fingered her pussy. Cliff was really getting into the action
particularly because of the way he had Sherry squirming and tossing on the
bed. Sherry moved her legs over Cliff's shoulders and pulled his head closer
to her pussy. Cliff held on to Sherry shapely buttocks and squeezed and
fondled her firm ass cheeks as he ate her pussy.  
  
"Oh, oh, yes right there. You got it. Suck it; chew on it, that's the way to
eat me, oh!" Sherry cried out.  
  
Cliff continued to eat her pussy as he held her big ass tightly in his hands.
He then moved his hands up to her tits and found her hard nipples. Cliff
massaged her boobs and twirled her nipples in his fingertips as he continued
to munch on her pussy and clit. Sherry was tossing and thrusting her pussy
into Cliff's face and calling for him to eat her.  
  
"Stick your finger in my ass," screamed Sherry.  
  
Cliff had never fingered anyone's asshole and he was taken back by the demand.
He snuck one hand behind Sherry's bottom and toyed with her asshole tickling
the tight nether hole.  
  
"Come on, wet your finger in my pussy and shove it in my ass," Sherry ordered.  
  
Cliff stuck his middle finger in Sherry's pussy and got it good and wet with
her juices. He then positioned it at Sherry's asshole and shoved it in. Sherry
gasped with the abrupt anal penetration but soon had Cliff's finger buried in
her ass. Cliff pumped his finger in and out of Sherry's ass as he continued to
maul her pussy with his mouth. Cliff loved the feel of his finger in the warm
recess of Sherry's ass.  
  
Sherry stiffened and gasped aloud as she came on Cliff's face. Cliff held on
to her with his finger still buried in her ass and his mouth glued to her
cunt. He felt the waves of her orgasm rock Sherry's body and his face was
flooded with her cunt juice. Sherry kept humping his face until the last of
her orgasms passed and she flopped back on the bed.  
  
Cliff slipped his finger from her ass and his hands found her breasts again.
He stroked her tits and nipples as he gently licked her pussy dry of all her
juices. Cliff finished eating her and then sat up kneeling between Sherry
legs. Cliff followed Sherry's eyes to his cock.  
  
Sherry smiled at him and said, "That was great. Now get that cock in my pussy
and fuck me!"  
  
Sherry again reminded him that she was still safe and that it was okay to cum
in her. Sherry preferred that guys didn't use rubbers as she liked the feel of
the warm cream shooting into her womb. Cliff leaned forward and aimed his cock
at Sherry's pussy. He slid in easily to the hilt and reveled in the warmth of
her cunt. Cliff began to pump his cock in and out of Sherry's pussy as she
wrapped her fleshy legs around his back. Sherry pulled him in with her legs
and positioned herself so that her clit was in constant contact with his cock.
Cliff began to pound Sherry's pussy and Sherry humped her hips back at him
just as hard. The two of them fucked each other frantically breathing heavy
and grunting and moaning. Sherry had another orgasm but continued to fuck
Cliff toward his. As she always did with boys, Sherry lost count of her
orgasms before Cliff finally filled her pussy with his spunk.  
  
Cliff stiffened and then thrust into her each time he felt his cum ejaculate.
Sherry rocked with him and she clenched her cunt muscles squeezing every drop
of cum from his cock. Cliff collapsed on her body as he felt the last surge of
cum leave his cock. Sherry held him tight as he relaxed his body. Sherry
rolled to her side and Cliff rolled with her. They held to each other and
gently caressed each other's sweaty body. Cliff stayed hard after his initial
ejaculation and Sherry noticed his state.  
  
"I can see that you are ready for action again. Have you ever fucked a girl in
the ass?" Sherry quizzed him.  
  
"No I haven't. I really never thought about it," Cliff admitted.  
  
"I love it in the ass. Will you fuck me in the ass?" Sherry asked sexily.  
  
"I guess, if you want, yeah sure I'll do it," Cliff replied unsurely.  
  
Sherry smiled at him and then got off the bed. She retrieved some lubricant
from her nightstand and handed it to Cliff. Sherry then got on all fours and
directed Cliff to lubricate her ass. Cliff got turned on by putting the lube
in her asshole. He enjoyed fingering her hole and caressing her curvy ass.
Sherry rotated her ass in arousal as Cliff inserted a second finger into her
bung hole.  
  
"Okay I'm ready for your cock Cliff, fuck me in the ass," ordered Sherry.  
  
Cliff knelt behind her and eased his hard cock into her ass. He worked it in
slowly and reveled in the methodical penetration of her luscious ass. Cliff
had never felt anything like this before. Sherry's ass was a warm tight
receptacle. Sherry used her sphincter muscles to perfection as she massaged
Cliff's cock in her anal sheath. Cliff caressed both of Sherry's gorgeous ass
cheeks as he fucked her ass deeply. They both sensed he was about to cum again
and Cliff picked up his pace as Sherry squeezed his cock with more intensity.  
  
"Cum in my ass, I want your cum in my ass," Sherry cried out.  
  
Her words sent Cliff over the edge and he fired his second load into Sherry's
hot ass. Sherry felt the warm sperm coat her rectal passage, a feeling that
she never tired of. She squeezed her anal muscles and milked Cliff's cock dry
of every drop of cum. Cliff continued to fuck her slowly until his cock
softened and slipped from her ass. Cliff just looked at her beautiful ass and
watched as trickles of cum ran out of her ass down her thighs and across the
lips of her pussy.  

The two of them flopped down on her bed to rest briefly but Cliff would soon
learn that they were just getting started. Sherry rolled onto her left side
and Cliff snuggled up behind her. He draped his right arm over her and
caressed her breast and tweaked her erect nipple. Cliff's cock was semi-hard
and he pressed it against Sherry's hot ass. Cliff was curious as to when she
started taking it in the ass so he asked her.  
  
"When did you first start butt fucking?" he questioned.  
  
"On the day after my 18th birthday a couple of months ago, you know Ziggi and
Vinni, right," Sherry began.  
  
"The Palmisano brothers, sure I play ball with them," Cliff replied.  
  
"I had a birthday party at my house Friday night and Vinni and Ziggi were
there with their dates. At the party they promised to take me out for my
birthday on Saturday. We went to their house because their parents were away
and we fucked all day. The first thing we did was with me on all fours sucking
Vinni's cock and then Ziggi fucked me in the ass," Sherry described.  
  
Cliff pictured Sherry on all fours with the two Italian studs banging her. He
had seen Vinni and Ziggi naked in the locker room plenty of times and he knew
that they were hung. Both Vinni and Ziggi had a reputation with the girls and
it was known around school that they had their share of pussy. Cliff tried to
imagine Ziggi stuffing his big Italian sausage in Sherry's virgin asshole.  
  
"Christ, didn't that hurt?"  
  
"Hell yes it hurt. Ziggi even greased me up good and it still hurt like hell.
I couldn't do much about it as Vinni had my mouth stuffed with cock and he
held me by the ears. Eventually the pain went away but I felt really bloated."  
  
"Did he cum in your ass?"  
  
"Yeah he did and it actually felt pretty good. The warm cream help soothe my
ass." Then Vinni came in my mouth and I swallowed every drop as he held onto
my ears. Next they switched places and Vinni fucked me in the ass while I
sucked on Ziggi's cock. My pussy was on fire but they hadn't touched it yet,
so I fingered myself until I came too."  
  
"Wow that sounds so hot. I'm sorry that you felt pain," Cliff offered.  
  
"They weren't done though and we had sex for nearly six hours. Once they goy
hard again they double fucked me with Vinni in my pussy first and Ziggi in my
ass. Then later they switched positions again. I kind of liked the double
penetration because I had a cock in my pussy and I had many orgasms. By the
time we were done they had cum four times each and I had two loads in my
belly, two in my pussy and four in my ass."  
  
"Unbelievable, how did you feel on Sunday?"  
  
"I could hardly move and I felt really constipated. The following weekend I
went out with the both of them again and they took me to their older cousin's
house. Pauli has his own pad and the three of them triple fucked me until they
had cum at least three times and I seemed to orgasm continuously. I had never
had better sex and I was exhausted when they finally brought me home."  
  
"Three guys at once."  
  
"Yeah, one in my mouth, one in my ass and one in my pussy; then they rotated
positions. It was pretty wild," Sherry sighed.  
  
"I bet. Are you still seeing them?"  
  
"No we got together a few times after that but then they moved on to other
chicks. Hey, what's that poking me in the ass?" Sherry giggled.  
  
Cliff realized that he was hard again and that his cock had slipped between
Sherry's buttocks. He snuggled closer to Sherry and they kissed and fondled
each other. Cliff kissed and sucked her breasts for a long time while his
fingers played with her sweet pussy. Cliff next kissed his way down Sherry's
lovely body and he soon had his face buried in her pussy. He brought Sherry to
three moaning, writhing and gasping climaxes. He moved up beside Sherry and
they kissed for a while. Finally, Sherry moved over him, slid down and took
his turgid cock in her hand and began to stroke it. Smiling, she slipped her
lips over its velvet head and slid it into her mouth. Sherry licked it then
she moved her mouth up and down. Her mouth moved up and down his shaft and she
rolled his large testicles in her hands.  
  
Sherry continued sucking his cock for several minutes till it was stiff, rigid
and menacing looking and she had Cliff moaning. She pulled back and got on all
fours, shifting her hips so that Cliff had to mount her from behind. Cliff
moved behind her and pressed his wet gleaming organ against her pussy. Sherry
reached back and guided him into her. Slowly he thrust forward, his cock
slipping deeper with each stroke. He pulled back each time letting her pussy
juices grease the way.  
  
"Oh God, that feels good. Deeper, fuck me, deeper. Oh yes!" Sherry moaned
aloud. "Oh, I love your cock."  
  
"Oh, Cliff, that feels so wonderful. I'm so glad we got together. Your cock
fills my pussy so well. Fuck me slowly." Sherry begged.  
  
Cliff held her by her hips and with long slow strokes fucked her. They fucked
for what must have been five minutes till Sherry began to moan.  
  
"Oh, Cliff, fuck me faster. It feels so good, fuck me hard. I love it when you
fuck me hard and fast. Fuck me hard. Yes, like that," Sherry begged.  
  
Cliff was more than eager to comply, and his muscles rippled as he began to
stroke long and hard against Sherry's body. His hips slapped against hers
causing Sherry's lovely breasts bob and swing as he slammed into her.  
  
"Oh yes, Cliff, that's the spot. Fuck me hard right there. It feels so good.
Yes, like that. That hits the spot that feels so good. Fuck me hard, harder!"
Sherry cried out.  
  
Cliff bent over and with his hips still thrusting he slipped one hand down to
finger Sherry's clit, the other reached under and caught one jiggling breast.
His hips moved faster slapping against her body. She moaned and sobbed her
passion. She cried out and threw back her head as she climaxed.  
  
Cliff continued to thrust. He quickly brought her to another climax. After her
third climax, Cliff joined Sherry in a fourth as he pulled out of her pussy
and shoved his cock back up her ass. Sherry loved the feel of warm seed
flooding her ass and she cried out telling him to cum in her ass. Cliff and
Sherry separated and lay together kissing. They talked for a while and then
Sherry took his cock in her mouth and licked his and her juices off of it,
cleaning it. She began to suck it in and out, and in a few minutes he was hard
again. Cliff was still amazed that Sherry would suck a cock that had just been
in her ass.  
  
"Now I want your big cock in my ass again. I want you to fuck my ass again and
cum in my asshole again," Sherry said in a sultry tone.  
  
As Sherry moved to all fours she placed her head on the bed and turned her
face to one side as she arched her back and accentuated her big curvy ass.
Cliff pushed a thick finger into her asshole and then he added a second finger
which caused Sherry to gasp. He worked the two fingers in and out of her ass
stretching her as much as he could. Cliff then placed his impressive erect
cock between Sherry's beautiful smooth round ass cheeks and pushed into her
asshole.  
  
This time Sherry moved away from him and ended up on the bed lying flat on her
stomach. Cliff followed her to the prone position and lay on top of her
shapely body with his cock between her ass cheeks and in her asshole. Cliff
began to hump Sherry at a slow pace and then faster with his hips pumping into
her. Sherry's screams and moans were louder than ever as her body took Cliff's
7" cock. Cliff lifted her back to her knees on all fours and reached around to
feel her tits. Her nipples were rock hard as he twirled them in his fingers.
Cliff then moved one hand down to play with her pussy and Sherry went wild
humping her hips faster and faster. Cliff then placed both hands on her hips
and watched his cock penetrate her curvy ass as he moved her hips in time with
his humps.  
  
Sherry yelled for the world to hear, "Oh my God, fuck me, fuck me, please fuck
me!"  
  
Cliff complied with her demands and pounded her ass as hard as he could.
Sherry squeezed her ass cheeks together and she orgasmed as Cliff joined her
and shot another huge load of cum deep into her ass. Sherry screamed and
moaned as she felt Cliff pump several shots of cum into her rectum. Sherry's
beautiful body radiated heat as Cliff pumped cum into her ass. Sherry was
almost out of breath but started to return to normal breathing as Cliff
caressed her body lovingly. Cliff eased his cock from her ass and traces of
cum ran out of her asshole between her ass cheeks, over her pussy and down her
inner thighs. Sherry scooped cum up with her fingers and licked them clean.
Cliff flopped on the bed next to her and Sherry once again dropped down and
took his softening cock in her mouth and sucked it dry.  
  
It took quite awhile but Sherry got Cliff hard again. Cliff moved to his back
and Sherry straddled him and reaching down she guided his swollen cock into
her pussy, slipping down till she had all of him in her. She leaned forward,
kissed him and then she began to rock up and down on his hard cock. Sherry
reached back fondled his swollen scrotum and rolled his testicles around.
Sherry's lovely big firm breasts bounced and the Cliff could see her nipples
erect and pointed. Cliff fondled her tits as Sherry moved up and down, her
hips thrust forward as she moved on him.  
  
Sherry rose and fell as she rode Cliff's hard organ. He caught her hard long
nipples in his strong fingers and pulled on them gently. He stretched them and
wiggled her breasts from side to side using her nipples. Sherry moaned aloud.
She rode him for a long time before she climaxed. Sherry collapsed on Cliff's
body and then he rolled her to the side. Cliff didn't cum again and he was
sure that he wouldn't be able to that day. However as they lay in the spoon
position, Cliff slipped his cock back into Sherry's ass. They fucked in this
position until his cock softened and slipped from her asshole.  
  
"You can really cum a lot," Sherry whispered.  
  
"I think that you had something to do with that," Cliff replied although he
knew that his ejaculations were always volcanic like and that he could cum at
least four times a day. However that day was the first time he came four times
with a girl.  
  
They rested awhile and then Sherry suggested they shower and get dressed. She
straightened up her room and stripped the bed. She knew that she would have to
wash the sheets and then remake the bed. Cliff finished his shower and got
dressed. Sherry was still naked when he left the house and he could not resist
grabbing her ass as he left. He walked the several blocks back to his car and
then drove home. It had been quite a day for Cliff and he was exhausted and
hungry.  
  
As he drove home her thought about everything that he and Sherry had done. He
had fucked her pussy and ass; she had sucked his cock and he had eaten her
pussy. Those things were all firsts for him. He had been worried about not
losing his virginity but that worry was over. He had never expected to learn
so much so fast. He wondered if he would go out with Sherry again and how he
would deal with Susan if she wanted to get back together. Cliff went home made
himself something to eat and then crashed in the TV room contemplating his
remaining days at high school.  
  
EPILOGUE  
  
The following week all hell broke loose as it was all over the school that he
and Sherry and made it together. Susan was livid and vowed never to speak to
him again. On the other hand Vinni and Ziggi slapped him on the back and
congratulated him for busting his cherry. A couple of girls who were known
action at school approached him. They said that Sherry said that he was a good
lover and they asked him if he wanted to go out sometime. Cliff smiled and
told them he would think about it.  
  
As it turned out Cliff did date some of the other fast girls and he had great
sex with them. He also dated Sherry a few more times and had incredible sex
with her. By the time he graduated he was having sex several times a week with
different girls and he loved his new found life. After graduation, Cliff
enlisted in the Marine Corps as planned and he felt very confident bout his
sexuality as he headed off to boot camp.  
  
It would be over four months before Cliff got laid again but he experience
came in handy for his first duty station. Cliff was assigned to security guard
duty in Naples, Italy. It was a two year duty assignment and he had a
marvelous time in Italy and other countries he visited, particularly France.
He would learn that many French women loved anal sex and he was only too glad
to accommodate them.




End file.

