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Subject: Training Jessica (MMFf, anal)
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This story is a work of fiction and contains sexually explicit material. If
you're not an adult, stop reading now (like this will help…)

This is my first attempt at a story, and my mother tongue is not English, so
forgive the quite clumsy language. Comments are welcome; I would especially
love to hear from female readers (I'm a 27-year-old guy), if there are any.


Training Jessica

Part I (MMFf, anal)

Jessica had met Frank six months ago. He was everything she could ask for and
more: handsome, gentle, and loving. The fact that Frank was quite wealthy and
older than Jessica was further added to his appeal. Frank was mature,
self-confident, and intelligent. He presented a stunning contrast to Jessica's
peers. In a word, he was adult. This was probably what Jessica had found most
appealing about Frank when he had walked up to her on the beach last summer.
Quite frankly, Jessica had never figured out what a 38-year-old business
executive saw in a 19-year-old college sophomore. Nevertheless, their
relationship was a dream come true for her, and she was happier than ever.

Their sex life was blooming, and Frank enjoyed making love to her frequently.
He was always gentle and attentive to her needs and never rushed, but made
sure that she felt comfortable. Frank obviously loved Jessica's petite body,
and she was equally infatuated with Frank's hairy and muscular frame.

During the past few months Jessica had learnt to trust him completely, and
she felt totally at ease with him. Frank paid special attention to making
sure that he remained trustworthy in her eyes and never asked Jessica for
anything she wasn't willing to do. She had been quite hesitant to performing
oral sex, but as she fell more and more in love with him she decided to make
the extra effort to make him happy. Frank never pushed her for a blowjob.
Eventually, he didn't have to; Jessica was eager to please him and knew that
the trick was to take his prick in her mouth.

One night Frank told Jessica not to make any plans for the following week. He
said he had arranged something special, and it would take all week. Whatever
it was, it was to remain a secret, and Frank refused to discuss it further.
Jessica was sure that Frank had arranged something extra nice, and looked
eagerly forward to next week.

Monday evening Frank announced that they would have guests at Frank's house
the same evening. Jessica was quite surprised, as she always liked to make
sure that Frank's place was nice and tidy before they would have guests over
and had wanted Frank to notify her well in advance. Frank told her not to
worry; everything was "set up" according to him. Jessica was eager to learn
what this meant, but Frank just smiled with a mysterious look on his face.

At 8 PM the doorbell finally rang. Frank opened the door and let a man and a
woman in. The woman wore a tight red spandex dress and stiletto-heeled red
pumps. She had way too much make-up on, and quite frankly looked like a madam
of a whorehouse. The man was even older than Frank; he had gray hair and wore
an ordinary business suit. He had a very conservative appearance. In fact
Jessica first thought that he was a business associate of Frank's. She was
confused. Who was this odd couple, and what on earth were they doing here?
Frank seemed to know them from way back, as he greeted them very warmly and
let them in.

"Jessica baby, meet Maxine and Jack. They are good friends of mine, and I
have invited them to my home for a very special purpose. They are here for
what we call 'slut training'." What? Jessica couldn't believe her ears! She
didn't know what it was exactly that Frank meant, but it sure didn't sound
good. "You see, baby, I have aimed for this moment for a long time. I know
you love me and like to please me, but the thing is that you just don't
please me enough. I have promised to take care of you, but you need to give
me something in return. I know you trust me by now, so let me do what I have
to do." Jessica was dumbfounded. Didn't Frank love him unconditionally? Had
he taught her to trust him for some special purpose? Wasn't this the ultimate
love affair but something very different? She loved him furiously and
unconditionally, and couldn't understand that this was necessarily not the
case with him.

"Jessie, sit down and let me explain something to you" Frank continued. As
Jessica sat down on the couch Frank sat next to her and gently took her hand
into his. "You see, I enjoy making love to you, but I have more needs than
you can currently provide for. I love your innocence and freshness, but
there's a lot about sex that you will now have to learn. Just going down on
me every now and then is not enough. But you don't need to worry, honey. I
have arranged everything; you'll just have to do as I say, and everything's
gonna be alright." he continued.

"Honey, I understand that this can be quite a shock for you, but you have to
trust me and let me take care of things. If you aren't going to be a good
sport, you will make me very unhappy and leave me no choice but to leave you.
I wouldn't want to be with someone who likes to hurt me." Tears came pouring
from Jessica's eyes as she sobbed in a state of shock. She wouldn't ever want
to be separated from Frank. She couldn't even imagine life without him.
"Don't worry baby", Frank continued and begun to gently stroke her cheek.
"Let Frank make it alright. Just do as I say, and everything's gonna be fine
again."

"Jack, I think we ought to start. We wouldn't wanna let her cry her heart out
now, would we?" Frank laughed. Jessica cried silently as Jack approached her.
"Baby, are you with me on this? You can walk out that door right now if
you're not going to be a good sport. Do you want to make me unhappy?" Jessica
could only sob and slowly shake her head. She would do anything to keep Frank
with her. "Are you with me on this?" he asked. Jessica nodded slowly. She
loved Frank more than anything else and would do anything he asked.

"I will see to it that you will learn how to become a good cock-sucking
little slut. I will personally train you to become my little pet whore. You
will suck masses of cock, and also learn to love sperm, both on your pretty
face and hair and also the taste of it. Alright Jack, show Jessica why they
call you 'The Hammer'." Frank continued. Jessica was in shock. How could her
gentle and loving boyfriend say such things. Frank never cursed and always
had behaved like a real gentleman. This was not the usual him; he sounded
like a complete stranger. Nevertheless, Jessica wouldn't do anything that
would jeopardize their relationship. She would do anything to keep him happy.

Jack stepped right in front of Jessica's face and slowly opened his fly. He
pulled out an enormous penis, and openly started to slowly jerk it. The head
of Jack's cock jutted out like a fist on a child's arm. Jessica stared at the
huge organ shocked by what was happening as well as the sheer size of the
shaft. "Baby, Jack is here to pump your tight pussy and to pop your virgin
ass. But first you have to make his cock rock hard. You know how to do that,
don't you?" Frank asked with an aggressive tone. Jessica was terrified. Frank
sounded so different. She had to take a look at her lover's face to make sure
it really was him talking. By the expression on Frank's face she could see
that he meant every word. She was dazed and confused. What was happening? Did
her loving boyfriend really want to see her being used by another man?

"Now suck that cock" Frank insisted. "You need to get it real hard, so Jack
can ram all of your holes." She couldn't imagine engulfing that enormous tool
in her petite vagina, let alone her tight rectum. Frank had occasionally
slipped a finger in her ass while they were making love and even that hurt a
bit. "Go on honey, suck that cock" Frank demanded.

In a daze, Jessica slowly closed her eyes and opened her mouth. Jack grabbed
her jaw with one hand and placed his penis between her lips with the other.
Slowly he pushed forward, making her tool slide deeper into Jessica's mouth.
Jack kept pushing and filling her mouth and started to enter her throat.
Jessica opened her eyes wide in panic and mumbled frantically. "Relax
honey...take that cock deep…swallow as it enters your throat…just relax."
Maxine instructed from a nearby armchair. "Lubricate the shaft with your
saliva…push your tongue way out so that the cock can slide on it...make sure
you have enough spit on your tongue... that's it honey, that's a good girl",
she continued. Jessica tried to relax and fight the choking reflex. She did
as Maxine instructed and didn't swallow any of her saliva, but kept it all on
her tongue. This helped her in her task. Jack had also stopped pushing
further and gently moved back and forth, pushing only half of his shaft in
her mouth. "That's good honey. Swallow that cock." Maxine continued. She
obviously was an expert in this field.

"Now Jack, give the little cocksucker all you have" Frank hissed. Jessica
knew what was going to happen and tried to relax her throat as much as
possible. Slowly Jack pushed in, this time passing the edge of her throat.
Jessica breathed heavily through her nose, quite clearly concentrating on the
task at hand. Jack grabbed her head and pushed all the way in. "The little
slut's mouth is so fucking hot" he groaned as he pushed the last inch in.
Finally, he covered her nose with his pubic hair. "That's good. That's a good
cocksucker." Frank hissed, watching the action from only inches away, petting
Jessica's head. Slowly Jack pulled back and Jessica breathed frantically. As
soon as the head of Jack's penis reached her lips, he begun to push back in.
The look on Jessica's face was confused and surprised. She thought the ordeal
was over with. But no, this man again begun to shove the monster organ in her
head. "Yeah Jack, fuck her face" Frank encouraged. Jack didn't need any
encouragement, as he very clearly enjoyed using the teenager for his personal
satisfaction. Gradually Jessica relaxed more and more, and let Jack pump his
young mouth. "Feels so fucking good. The bitch is so fucking hot." Jack
groaned as he worked his huge penis in and out of Jessica's mouth. "Don't
come too soon," Frank said. "You still have two more holes to cover."

Maxine clearly enjoyed the show. She was very excited and enjoyed seeing Frank
offer his teenage sweetheart to Jack's disposal. This was clearly what Maxine
enjoyed doing. Seeing Jack fuck Jessica's teenage face was obviously a great
turn-on for her.

After several minutes of face fucking Maxine intervened. "I think it's time
to stretch some teenage pussy," she said. "You're right." Frank answered. "I
think we've made enough progress in the face department for now" he laughed.
Jack pulled his cock out of Jessica's mouth and stepped aside. "Take off your
clothes" Frank ordered. Slowly Jessica complied. She was a shy girl, but
having been molested in front of Frank and a complete stranger had put her in
a daze. She was fueled with a furious desire to keep Frank happy and to do
whatever he demanded. Slowly she stripped until there was not a shred of
clothing on her. "On the floor. On all fours. Maxine will now make sure that
you are ready for some serious fucking" Frank said. The three of them laughed
and Maxine stepped forward with a bottle of baby oil. She took Jessica by the
hand and pulled her on the floor. "On the floor…that's a good girl….on all
fours now" she hissed as Jessica assumed the position. Maxine rubbed plenty
of baby oil on her right hand and without a warning placed it on Jessica's
tush. "What…?" Jessica moaned and looked at Frank with a helpless look in her
eyes. "Just take it honey. Don't look at me for help. Max knows what she's
doing." It wasn't Maxine's competence that Jessica was concerned about. She
had never had another woman touch her intimately and here she was on all
fours with another woman stroking her womanhood.

Maxine circled her hand around Jessica's tush, constantly adding oil.
Suddenly she inserted two fingers into her. Jessica let out a silent moan and
jumped forward. "Take it, baby. That's good cunt…that's a good little whore"
Maxine whispered as she begun to work her fingers in and out of her tight
little twat. Jack stood beside the pair, slowly jerking off. He was pleased
to see that the little box was being well greased up for him. He was sure to
give the little cunt the reaming it needed. Slowly he stripped, as he knew he
was in for a long night.

After a couple of minutes Maxine stopped. "The twat's ready. I think it needs
some cock now" she said and stood up. "Sure" Jack replied and knelt behind
the teenager's bare bottom. With one hand on her ass, he placed his penis on
the entrance to the vagina. Slowly he pushed in, much in a similar fashion as
he had earlier intruded her mouth. After pushing an inch or so in, he grabbed
her by the waist with both hands and pushed forward. With a smile on his face
and his eyes closed he let out a deep sigh of pleasure as he pushed his
monster tool all the way in. Jessica moaned, obviously in pain by the huge
tool stretching her tight teenage pussy. She thanked Maxine in her mind for
lubricating her thoroughly. Without the baby oil the pain would be too much,
she was sure. Maxine knelt beside the couple and begun to gently pet
Jessica's face and hair. "That's it baby…be a good cunt now and take it all
the way in…just relax your pussy…you can do it baby." Maxine whispered words
of encouragement as Jack begun to pick up a steady pace pumping the young
twat. Jessica moaned and sobbed a little bit as she tried to accept the big
penis in her tight womanhood. She wanted to cry; this sick couple was calling
her all kinds of names, and Jack just used her for his own pleasure. They
were treating her like she was a dirty prostitute. She couldn't understand
what she had done to deserve this. This was not lovemaking. This was fucking.

As Jack pumped his cock in and out of Jessica's tight pussy, her own juices
started to flow involuntarily, and the fucking became easier. She even begun
to rock herself back and forth, trying to accept as much as possible of the
huge cock in her. Maxine and Frank were very pleased to see this happen, and
encouraged her to go on. "Good, good, baby. That's a good little slut." Frank
encouraged her from the couch. Jessica looked up at Frank and with tears in
her eyes and smiled a little bit. She was relieved to see that she was doing
ok. "You're doing great…are you my little cunt?" Frank said. "Uhhh…yeah…"
Jessica managed to answer, rocking back and forth as Jack slammed the monster
cock in her. "Say it…say you're my little cunt whore!" Frank demanded.
"Mhh…Ahh…I'm…your cunt…I'm your whore" Jessica groaned as Jack continued to
work his giant prick in and out of her. Maxine and Frank laughed in approval,
obviously amused by the amount of concentration Jessica had to use just to
speak a few words.

"Man, I gotta stop before I come" Jack soon announced and pulled his cock
out. Maxine and Frank were a bit disappointed as they would have preferred
Jack pumping Jessica's tight twat for at least an hour or so. Jack had been
able to keep a steady pumping rhythm going for half an hour; even that was
quite a performance, as most men would have come ages ago. The sensation of
penetrating a tight teenage pussy and then giving it a good reaming would
probably make most men come in minutes. Jack was clearly an expert in the
field. "We can always use one of your toys to stretch her some more later,"
Frank said to Maxine. "Good idea. Originally I had planned to plug her ass
only, but I suppose we can do both holes." she replied. "What are you
saying?" Jessica protested from the floor, obviously afraid of whatever the
trio had planned. "Don't you trust me? Are you quitting, is that what you're
saying? You can put your clothes on and walk out whenever. Just remember that
you can never come back. You can leave right now if you want to." Frank said.
Jessica lowered her eyes in submission. "Please Frank, don't say that. I will
do anything you say" she sobbed. "That's better. Max, I think it's time to
change holes." Frank said. "Sure thing" Maxine laughed.

Maxine grabbed the baby oil again, this time smearing it across Jessica's
anal passage. Jessica was terrified, as she knew what was coming. She had
serious doubts that she was up to what was about to happen. However, she had
long ago decided to do whatever it takes, and just closed her eyes and
waited. Maxine lubed her ass up in a similar fashion as she had done her
pussy. Jessica moaned in pain as Maxine shoved two fingers in her tight ass
and begun to pump back and forth. "Relax. You're way too tense. It will only
hurt more that way. You need to let go." Maxine instructed. Jessica nodded
and tried to comply the best she could, but it still hurt a bit.

"She's as ready as she will get. I think you still better grease up that cock
too," Maxine said to Jack after a couple of minutes of ramming the young
asshole with her fingers. Jack picked up the baby oil and smeared lubricant
all over his cock. Maxine pulled her fingers out of Jessica's ass, and Jack
again positioned himself behind her. "Now take that cock…be a good whore…be a
good ass-fuck" Frank hissed as Jack started to penetrate the virgin asshole.
Jack had his left hand on Jessica's lower back and with his right hand he
shoved his monster cock past the entrance to her ass. Jessica opened her eyes
wide and screamed in pain as Jack continued to brutally penetrate her anal
passage. "Take it bitch" Jack groaned as he continued to thrust forward.
Tears begun to flow from Jessica's eyes as she tried to allow Jack's monster
prick in her tight rectum. As Jack had thrusted past the entrance he again
grabber Jessica by the hips and started to push deeper into her. Jessica
cried and sobbed as Jack continued to conquer her tight ass. "Good girl…take
the cock…just take it like a good ass whore…that's a good girl" Maxine
encouraged Jessica and gently wiped tears off her cheeks. "That a girl…that's
a good girl" Frank hissed, obviously very turned on by the sight of Jack
brutally violating the teenager's virgin asshole.

Finally Jack had managed to thrust his cock all the way in and started to
pump in and out. Every time Jack shoved his cock in, Jessica moaned and
produced another burst of tears. "Hell, this ass feels so good…it's fucking
hot" Jack begun to whisper as he picked up a steady pace. Jessica was in a
daze. She could only sob as the giant shaft pumped in and out of her.

Frank wanted Jack to pump his little treasure for a long, long time. He
decided to make sure this would happen. "Max, get a glass of cold water,
would you please" he said to Maxine. "Sure" she replied and headed for the
kitchen. "Jack, when you feel you're about to come, pull out and squeeze the
head of your prick. Then dip it in the cold water. This way you'll last way
longer!" Frank instructed. "Excellent idea! I wouldn't want to come too soon
and spoil the fun. I want to pump this bitch's ass for a long time!" he
replied. Jessica sobbed in desperation. The love of her life was making sure
that the brutal violation of her most intimate places would last as long as
possible! This was a nightmare she thought. But no, it was reality, and there
was no escape.

Maxine came back with the water and placed it beside the fucking couple. She
herself sat down on the couch next to Frank. "What a beautiful sight" she
commented as the middle-aged man pounded the teenager's tight asshole. "It
really is" replied Frank.

Every now and then Jack pulled out and did as Frank instructed. Every time
Jessica hoped that Jack was coming and that the ordeal was over. But no, Jack
kept intruding her asshole and again and again picked up that same, steady
rhythm. His cock was like a mechanical piston, working steadily in and out.
Jack kept his hands on her hips, constantly dirty talking. "Sweet ass-fuck
whore…that's a good girl" he whispered and pumped away. Jessica felt lower
than she had been capable of dreaming earlier the same day. She was being
used and converted into some sort of slut. Was her future to become a fuck
toy and porn slave for Frank? She wished it wasn't so, but she knew better.
This was only the beginning; she was sure that Frank had lots of things in
store for her.

Jack continued to pump the teenager's ass, maintaining a steady pace. Every
now and then he would pull out and do as Frank instructed. The trick worked
perfectly; Jack repeatedly prevented himself from orgasming. His erect dick
even shrank a bit every time after the cold water treatment, and he was able
to maintain the steady pace when fucking Jessica's ass.

Frank and Maxine very much enjoyed the sight of Jessica being introduced to
the pleasures of anal sex. The teenager seemed increasingly at ease as Jack
continued to pump away. Gradually she became less and less tense and was able
to receive the reaming with relative ease. She didn't seem to enjoy the
fucking too much though but passively took it like an animal being breeded.
This was a fact that clearly turned both Frank and Maxine on; they wouldn't
want their pet whore to enjoy this all too much. After all, they didn't want
things to slip out of control.

"Man, I can't take it anymore. I need to come" Jack finally announced. He had
pumped Jessica's ass for nearly two hours now, and despite the cold water
treatment he felt his groin was going to explode. "Ok. Come around her, I
want you to come on her face and hair." Frank said. Jack pulled out and
walked around Jessica. "On your knees, cunt" he hissed and grabbed Jessica by
the hair. Jessica rose on her knees in front of Jack. Slowly Jack begun to
masturbate, his cock only inches away from Jessica's face. "Remember to spurt
across the face and hair" Frank instructed. He was very specific; he wanted
to see Jack make a real mess on her. This was obviously going to happen, as
Jack's balls were nearly the size of tennis balls and he had been fucking the
teenager's holes for hours.

Jack moaned as the first spurt of sperm shot out of his cock. It landed
across Jessica's nose and she instinctively dodged a little. "Take it all.
Don't move. Open your mouth" Frank instructed from the couch. Jessica did as
instructed, and Jack instantly took advantage of the opportunity and shot a
spurt of sperm into the teenager's open mouth. He continued jerking his cock,
chancing his aim after each spurt. His cock produced nearly ten powerful
squirts, and he carefully made sure to cover all areas of Jessica's face and
squirted plenty in her hair as well. Finally Jack was drained, and he stepped
aside. Jessica's face and hair was completely covered with cum, and the
thick, white fluid started to slowly drop down from her face onto her chest.

"Beautiful…good girl…that's a good girl" Frank whispered. Maxine got on the
floor next to Jessica and smiled. "Now, little girl, you need to eat some."
she said. Jessica naively thought Maxine was referring to food and gave her a
little smile back. "Open wide" Maxine ordered and grabbed Jessica's jaw. A
little surprised, she complied. Maxine used her fingers and long nails to
scoop semen from the teenager's face, and then pushed it into her mouth.
"Lick it up" she hissed and continued to fill Jessica's mouth with sperm.
"Now swallow," she said as Jessica's mouth begun to fill up. Hesitantly she
gulped down the semen, trying hard not to throw up. This was another first;
Frank had always come inside her (she was on the pill), and had never even
suggested coming in her mouth. Quickly the teenager continued to clean the
mistress's fingers and swallowed each portion dutifully as Maxine filled her
mouth again and again. Finally there was no more semen left on her face, only
her hair was a total mess. "Now she's been fucked and fed" Maxine laughed.

Maxine then stood up and reached for the bag she had brought with her. She
pulled out a pair of rubber panties that had two dildos attached to it. The
dildos were attached to the inside of the pants so that whoever wore them
would have both her pussy and ass filled. "Put these on" Maxine ordered.
Jessica took the panties hesitantly and tried to fit them on. "Go on slut,
your holes have been properly probed, and ready to accept the rubber cocks.
Just shove them in and pull the panties all the way up." she continued.
Slowly she placed the heads of the dildos on the entrances of her holes and
started to push them in. They slid in easily; after all, she had just been
thoroughly penetrated in each hole, and her flowing juices had made her quite
slippery. Slowly she pushed the rubber cocks all the way in and then pushed
the panties all the way up her waist. Neither of the rubber cocks were nearly
as big as Jack's prick, but having one in her pussy and another one in her
tight ass made her feel even more filled up than when Jack had fucked her.
"Wearing that over night should keep her mind on what's important" Maxine
laughed. "You're the best" Frank replied.

Maxine got up and Jack started to dress up. Frank thanked them for a lovely
evening, and told Jack that she could drop over any time and fuck Jessica in
any or all of her tight holes. Jessica was terrified to hear that the session
could and probably would be repeated in the future. Maxine and Jack told
Frank that the pleasure was all theirs, and that it was always a pleasure to
break in a new slut. So they were professionals! Who was Frank, the man she
loved anyway, Jessica wondered. What kind of perverted beast had conquered
her heart?

"You did good, sweetheart" Frank said to Jessica. "I'm very pleased and will
allow you to stay with me. Tomorrow you will practice cock sucking some more.
I will also see to it that you will get accustomed to the taste of sperm. I
have lots of friends who are kind enough to help me with this. Now you need
to clean yourself up and get some sleep. Take a shower but keep the panties
on. Tomorrow's a big day." He continued. Jessica headed upstairs for shower,
scared of what Frank had just said. If this was the beginning, what more is
to come? Jessica didn't know what could be more perverted that what had just
happened. "Later guys. See you tomorrow at the glory holes." Frank said to
Maxine and Jack as he escorted them to the door. Glory holes? What was Frank
talking about Jessica wondered as he continued upstairs, walking awkwardly
with the dildos filling her holes…

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