Gambling Debt
Nobody messed with Bobby. That's the first thing you have to understand.
Nobody. Bobby didn't seem to do anything for a living, but he was always in the
money pretty good, and his house was a grand place, out in the country a bit,
and on a lot of land. People who messed with Bobby had accidents. It was
widely considered to be unlucky to get on Bobby's bad side.
That was Jim's problem. He owed Bobby 15 Gs, and Bobby wanted his money. Jim
didn't have it. That particular Wednesday afternoon, Jim showed up at Bobby's
house to try to settle up. Now, Jim is a nobody kind of guy. You know the
type, always about to make the big score. He is a medium sized guy of maybe 25
years or so, with an ugly kisser and a whiney voice. His sister Annie was with
him, just to get out of the house.
He had called ahead. You just don't walk in on Bobby. After all, he might be
busy. Bobby had told him to park around back, and he met them at the door. The
back patio door led into his rec room. Bobby was all business. "OK, you got my
money?"
Jim started his usual whining song and dance, but Bobby cut him off. "Did you
come all the way out here to tell me you're still broke? I knew that. I keep
up with things. I was hoping you would at least have come up with an
entertaining excuse. I'm losing my patience with you, Jim." Bobby was talking
so low Jim could barely hear him. Jim had heard that when Bobby talked low like
that, it was bad. Real bad.
Then he had a thought. Maybe Bobby would gamble for it. "Look, Bobby, I don't
have the money, but how about we shoot pool for it. You have a nice table right
here. What do you say?"
Bobby just shook his head. "That would be great for you, but what if I win?
You can't even pay me the 15. How would you come up with more? You don't have
anything to bet with."
Jim knew he had to think of something. "OK, how about Annie? If I lose, you
get Annie. For an hour."
Annie sputtered, "No way! You can't gamble with me! You don't own me!"
Bobby just laughed. "Even if your little sis agreed, what makes you think an
hour with her is worth 15 Gs? I might go 50 bucks."
Jim grabbed Annie and pulled her aside. She kept repeating, "No way!" He was
practically crying. "Look, sis, I can beat him easy. You know how good I am.
I'm going to get killed if you don't help. Please, Annie." Well, it took some
time, but she finally agreed.
When Annie told Jim she'd do it, Bobby took a better look at her. She was 5'5"
tall, light brown hair, and maybe 115 pounds. She was cute from what he could
see, which wasn't much with the bulky sweatshirt she was wearing. Bobby thought
and said, "Here's what I'll do. I might as well play, since you don't have the
15 anyway. We'll shoot straight pool, one rack, and if you win you are square
with me. If I win, I get Annie for an hour for every ball I win by, and you
still owe the 15."
Jim didn't think he had much choice, and convinced Annie to agree, so Bobby got
out a video camera and recorded Jim and Annie agreeing. They lagged for the
break, and Bobby won, so he broke the rack. He didn't play safe, he just
blasted them. Nothing dropped.
Jim made five and then missed an easy bank into the side. Bobby cleared the
table. "Well, good game, Jim. Ten to five, so I guess I win by five. It's
3:30 now, so Annie is mine until 8:30." He turned to Annie. "Ok, doll, strip."
Annie looked stunned. "W w what?"
"It's not a tough thing to understand, honey. I own you for the next five
hours, so strip off your clothes. I want to see what I won. Now!"
Annie looked at her brother, but he just looked away, so she stood up and slowly
removed her clothes. She was sobbing the whole time. When she was naked, Bobby
told her to stand with her feet separated a bit and clasp her hands behind her
back. Annie was still crying and looking at her brother for help. Now that she
was stripped, Bobby could see she was very nicely formed.
Jim was trying to think what to do. He finally said, "How about another game.
Give me a chance to win her back." Jim knew he would have won if he hadn't
missed an easy shot.
"OK," Bobby answered, "but if we play again, here's the deal. If you win, you
take off an hour for every ball you win by, and if you win by more than five,
you're in the clear on the 15. If I win, we add what I win by onto the five
hours I already have, and the hours turn into days. In other words, if I win by
three, that's eight total, and I get her for eight days."
Jim and Annie talked it over, and finally agreed. Bobby video taped it again.
It was Jim's turn to break, and he tried to play safe, but blew it. Bobby made
eight in a row and then missed. Jim cleared the rest. "OK," Bobby said, "I win
by one. I own her for six days."
Bobby turned to Annie. "So, darling, tell me about yourself. How much
experience do you have with sex?"
Annie practically whispered, "None."
Now it was Bobby's turn to be surprised. "None? You mean you're a virgin?"
"Yes."
Bobby said, "Interesting, so tell me what else you have done. You give
blow-jobs? Hand jobs? You ever take it up the butt? What have you done, and
how old are you?
"I'm 19, and I've never done any of that. I've kissed two different boys."
Jim hadn't known Annie was a virgin. He said, "Look, Bobby, give me one more
chance. Let me win her back, OK?"
Bobby thought about it. "Fine, but here's what I offer. If you win, even by
one ball, you take Annie and we're square on the 15, but if I win, I own her
permanently. Take it or leave it."
Jim and Annie didn't know what else to do, so Bobby taped their agreement.
Bobby said, "I know this isn't exactly a legal contract, and if Annie takes a
powder on me, I'm stuck, but it would be bad karma for her to do that. Who
knows what kind of bad luck would follow something like that?"
Jim didn't know how he got into this, and Annie was just sort of numb. No men
had ever seen her naked before, and here she was, naked in front of two men, one
of them her brother.
It was Bobby's break. He got lucky and made one off the break. Then he ran the
table. There was a long silence, and then Annie started crying. It was Jim's
turn to look stunned. Bobby waited a minute and then said, "OK, when do I get
my 15 large?"
Bobby let it sink in a minute, and then said, "Alright, everybody knows what a
nice guy I am. I'll give you one more chance. Annie has a sister, right?"
Annie started yelling, "No, NO, NO," over and over again. Bobby grabbed her arm
and pushed her onto a sofa. "Shut up, doll. I own you, permanently, so don't
you try to tell me what to do."
He turned to Jim. "You get her sister to agree, and we'll play one game of nine
ball for her. If I win, I own her, too, and if you win you get both women back.
Either way, I wipe the 15. If you agree, go convince her and bring her back
here."
Jim only thought a minute. He knew he really had no choice. He just walked out
the patio door, and didn't say a word. After he left, Bobby walked over by
Annie. His first words surprised her. "I'm sorry. I didn't know you were that
inexperienced or I wouldn't have made you strip in front of Jim. Anyway, I need
some more information. Do you know how to masturbate?"
Annie was still in shock. "I think so. I tried it a couple of times, and it
made me feel good."
"OK, honey, put your hand between your legs and masturbate for me." Annie
tentatively started rubbing her pussy with the fingers on her right hand. She
didn't look trimmed, but her bush was short. Bobby just watched her for a few
minutes, and then said, "OK, stop for a second. I want to see if you are wet."
When she moved her hand, he ran two fingers up her slit and held them up for her
to see.
"Gosh, darling, you are soaked. You must like this." He took his fingers and
smeared her juices across her upper lip. "There, now you can smell yourself.
Put your hand back and get busy. Tell me if you think you are going to come."
Annie closed her eyes and started again. Bobby said, "Open your eyes and look
at me, darling. I want to watch your face." Annie opened her eyes. She was
squirming a bit now as her excitement rose. She stared into his eyes as she
rubbed her fingers up and down her pussy, and Bobby stroked her hair and lightly
ran his fingers over her nipples.
Pretty soon she was moaning a little, but trying to hide it, and shortly after
that she whispered, "I think I'm going to have an orgasm."
Bobby immediately said, "Stop! You can't come without my permission,
understand?" She was still looking into his eyes, and just nodded. His hands
just kept stroking her. After a couple of minutes, he said, "OK, start again."
She nodded again, still staring into his eyes, and put her hand back between her
legs.
Before long she was panting and moaning openly. She said, "Please, can I have
my orgasm now?"
Bobby just said, "Stop!" He kept letting her masturbate until she was close and
then stopping her. He never told her to beg, but by the fifth or sixth time she
was shamelessly pleading to be allowed to come. Finally, he said, "OK, come for
me on the count of five. One, two, three, four, ........ five." Annie nearly
exploded, she came so hard. She though she might faint. It just went on and
on. Bobby held her and stroked her until she quit shaking. She stared into his
eyes the whole time.
When she had settled down, he pulled her head against his chest and hugged her.
"How was that, then?" he asked her.
"It was amazing. How did you make me do that? I must be a slut or something."
Bobby chuckled at her. "Don't worry. You are perfectly normal. Sex should be
amazing. Just wait until we get you really warmed up." He handed her a throw
off the back of the sofa. "Wrap up in this. Your brother will be her pretty
soon. Until he gets here I want you to see how many times you can come, so play
with your pussy under the throw. When your brother gets here, I want you to
keep masturbating secretly under the throw, but you can't come while he's here,
and when he leaves you need permission.
As Bobby got up from the sofa, Annie touched his arm. "Please, could you do me
a favor? Win my sister Amy. She would be better off away from my brother.
He'll just lose her to someone else now that he has the idea she's worth
something."
Bobby stopped. "How old is she?"
"Amy was 18 last Saturday."
Bobby thought. "OK, I'll give it a try, but only if you come at least three
times before Jim gets back, so you better get busy."
Bobby passed the time throwing darts and watching Annie on the sofa. After a
couple of minutes, she had opened the throw so she was fully exposed. When
Bobby gave her a quizzical look, she said, "It turns me on to know you're
watching me."
Jim showed up about a half hour later, with Amy in tow. She looked scared out
of her wits. Annie covered herself back up before they came in, but by then she
had come four more times, and she was covered in sweat with her hair matted
down. When Jim and Amy came in, Amy ran to the sofa and hugged Annie. Annie
whispered in her ear, and Amy gave a strange glance at Bobby.
Jimmy said, "Let's get this over with, you bastard. I want to get my sisters
home before you rape Amy, too."
Bobby laughed at him. "Well, at least you're confident. Of course, I didn't
rape Annie, did I Annie?"
She looked right at her brother and said, "No he didn't rape me, and I don't
think he will. I think in a little while I am going to be begging him to do
me."
Bobby taped Jim and Amy agreeing to the new deal, and then said, "Ok, let's go."
Bobby had the balls racked for nine ball. It was Jim's break, and he made the
seven off the break. Unfortunately, the one ball ended up blocked behind some
other balls, and Jim missed his attempt to bank into it. It was a table
scratch, and ball in hand for Bobby.
Bobby looked over at Annie, and said, "This one's for you, honey, just like I
promised. You did good." Then he looked back at Jim and said, "Watch and
learn." With that, he placed the cue ball on the table, lined up, and stroked
it. The cue ball hit the one, made two rails, and dropped the nine in the side.
Game over.
Bobby turned to Jim. "OK, this is what you are going to do. Here's 200 bucks.
You're going to go rent a truck, and you are going to load everything that
belongs to these girls into it, including family photos, documents, whatever.
You will have that truck here by noon tomorrow. If anything is missing or
damaged, you will be too. After you unload the truck you are going to leave the
state and never come back. Your rights in this state have been revoked.
Understand?"
Jim just nodded and left.
The moment the door closed behind him, Annie said, "Please, may I have an orgasm
now? Please?" Bobby let her beg for a couple of minutes. Amy was staring at
her with an amazed expression on her face. Finally, Bobby told her to go ahead
and come, and her whole body arched into the air, almost lifting her clear of
the sofa as the most powerful orgasm yet overwhelmed her. Amy and Bobby both
watched fascinated as wave after wave of pleasure washed over Annie.
When it was over, Bobby told Annie to put her hands on top of the throw and wait
quietly while he talked to her sister.
Bobby sat in a club chair and motioned Amy to stand in front of him. When she
was there, he said, "So, what did Annie whisper in your ear when you first got
here. Be sure to tell the truth, because Annie will tell me if I ask her."
Amy looked at Annie for a moment, and then said, "She told me not to worry. She
said you would win, and I would be better off."
Bobby said, "OK, now tell me about your sexual experience. I want to know if
you're a virgin, and if you aren't, I want to know when and how you lost your
cherry. I want to know if you have ever given or received oral sex, had anal
sex, given a handjob, French kissed, and so on. Don't leave anything out. I
own you now, and I want to find out about my new property."
Amy turned bright red, but didn't say anything for almost a minute. Bobby just
waited. Finally she took a couple of deep breaths and started. "I'm a virgin,
and I have never done any of those things. I have never even seen a penis,
except in pictures in health class, and I've never kissed a boy. Are you going
to rape me?"
"No, probably not. Do you want me to rape you? Are you going to be
disappointed if I don't? Do you want to see a penis? Do you masturbate?"
Amy took a couple more deep breaths. "No, I don't want you to. Please don't
rape me. I have played with myself in the shower a few times." Now she was
bright red, and she didn't think it was possible to be more embarrassed than she
was right then. She was wrong.
"OK, Amy, undress now. I want you standing right there naked in about one
minute. Don't make me wait."
Amy had known it was coming, but it was still a shock to hear the words. Like
her sister, no man had seen Amy naked since she was a little girl. It took her
a minute to work up the nerve to start, but her sister encouraged her, and once
she started, she undressed in record time. She thought it would be easier if
she just got it over with.
Once Amy was naked, she stood there, shivering slightly, right in front of
Bobby. He didn't say a word. He just watched her. Before long, she was
shivering harder, and was still bright red. Finally, Bobby reached up and
lightly ran his fingers up her slit. She made no effort to stop him. He
grinned at her. "You're soaked, girl. You're really turned on, aren't you?"
Amy just nodded. "Why are you so turned on?"
Amy didn't know what to say. "I don't know. I never felt like this before.
I'm a good girl. Please, let me get dressed."
Bobby ran his fingers up and down between her pussy lips, and she shuddered
violently as he did. "Is this how good girls act?" Amy shook her head no.
"Well, then I guess you have to be punished, don't you? Lie down over my
chair." Bobby guided her so she lay over the padded leather arms of the chair,
with her hands barely reaching the floor on one side and her feet in the air.
She wasn't really lying on him, because the arms of the chair held her up off
his lap. When she was in position, Bobby said, "Tell me you've been a bad girl,
and ask me to punish you."
Amy was starting to sob, but managed to say, "I'm a bad girl. Please spank me."
Bobby reached under her with his left hand and began circling her clit with his
fingers. Then he started spanking her with his right hand, very gently at
first. Amy started moaning almost at once.
As Bobby spanked her harder and harder, she moaned louder and louder. Bobby
warned her not to have an orgasm without permission. Amy's mind was whirling
and she felt so dizzy she thought she might die. She had always had fantasies
of being captured and then spanked by some powerful man, and she didn't know how
he had known to do this to her. It was like he could see inside her mind.
Finally, she started begging. "Please let me have an orgasm. Please give me
permission. I can't stop it. Please. Please. Please."
Bobby just said, "OK," and kept spanking her. She came almost instantly then,
her mind whirling faster and faster as she spiraled out of control. She had
brought herself off a few times in the shower, but those experiences did nothing
to prepare her for this. Her body spasmed completely out of her control, and
only Bobby's strong arms kept her from falling to the floor. Her mind spun down
and down into a black whirlpool.
When she came back to herself, Amy was lying in Bobby's arms on the sofa, with
Annie kneeling on the floor next to her. For some reason she felt very safe
lying on his chest. They had covered her with the throw, but she was still
shivering a bit from the aftermath of her incredibly powerful orgasm. Bobby was
kissing her forehead gently, while Annie was rubbing her feet.
"Did I pass out?"
"No, darling, you didn't quite pass out. It was close, though. Was that better
than the shower?"
Instead of answering his question, she said, "Now I know why Annie told Jim she
would beg you to do her. What are you going to do with us?"
Bobby smiled at her. "I'll do whatever I want with you. I own the two of you."
Both girls knew it was true. Their brother may have lost their bodies, but
Bobby had claimed their spirits.
Bobby held Amy for almost an hour, and she slept most of that time. When she
woke up, she was still lying on top of him, under the throw, and her sister was
sitting on the floor with her head leaning against Bobby's side. Annie was
sound asleep. Bobby and Amy tried to slide out without disturbing Annie, but
she woke up. Once both girls were fully awake, Bobby asked them if they wanted
to see the rest of the house. When both expressed enthusiasm, he took them on
the "Cook's Tour" of the place.
His house was the biggest the sisters had ever been inside. There were three
floors, seven bedrooms, 10 baths (one for each bedroom and a public bath on each
floor), sauna, hot tub, indoor pool, professional class workout room, a huge
living room, library, ... well, you get the idea. Amy asked and was told the
house was about 14,000 square feet.
During the tour, Bobby showed them his huge master suite, and asked if they
could keep a secret. They both said they could, but he made them both swear and
promised them dire consequences if they ever told. They he showed them the
concealed panel that slid back and gave access to an entire hidden complex.
There were passages that connected to most of the other rooms, secret
staircases, and whole hidden rooms. Bobby said he was only showing them because
he owned them and they would be living in the house from now on.
He also told them that the bedroom closest to his would be theirs to share. It
had easy access to the master suite via either the regular hallway or the secret
passages. Like all the rooms, it was ample in size, and would easily
accommodate two full or queen beds. He explained that they would have to shop
for furniture in the next day or two.
After they had toured the house, he brought them back to his master suite and
told them to both lie on the bed. They were both still naked, of course, and
had been throughout the tour, so Bobby hit the remote for the gas fireplace.
Then he told them both to masturbate for him. "Remember, you can't come without
my permission, so don't forget to ask. You may begin."
Annie and Amy were a little embarrassed to be lying side by side, but they
seemed to be getting less nervous about the whole situation. Annie was first,
begging Bobby for permission to come. He let her beg for a while, until she was
quite frantic, and then made her stop and lie still. Meanwhile, Amy was getting
close and started to beg for release. As with Annie, he let her get pretty
frantic before stopping her.
The three of them continued like this for nearly an hour, and both girls were so
close to coming that he could only let them rub their pussies for a minute or
two before he had to stop them. Finally, he made them both stop. Then he
flipped a coin, and Annie won. Bobby got on the bed between her legs and
started running his tongue up and down her slit, around and around her clit, and
then back up and down again.
He had told her it was OK to orgasm now, and she quickly did, but he continued
to lick and suck her until she lost count of how many times she had come.
Meanwhile, he was making Amy rub herself until close every few minutes. After
about 1/2 hour of keeping Annie in ecstasy, he switched to Amy, giving her
permission to come. For the next 1/2 hour, he brought her to one crashing
orgasm after another.
When he was done with them, both girls were as tired as they had ever been, and
both were thinking that the life of a slave wasn't so bad. Annie finally asked,
"When are you going to have sex with us. I thought you would have by now. I
don't think either one of us would mind."
Bobby laughed quietly. "You call that begging? You'll have to do a lot better
than that before I agree to penetrate either of you. You will, too. I promise.
Let me tell you how it's going to work. You girls had no experience giving or
receiving sexual pleasure. I decided it would be best to teach you about
receiving pleasure first, so that's what we've been doing."
"When I think you are getting good enough at that, I will start you learning how
to give pleasure as well. You'll start with some basics, like hand and mouth
work to make a man happy. You don't get to have intercourse until you know how
to give and receive pleasure. When I think you're ready, I'll get you really
ready. I'll probably make you masturbate like I just did, but you won't be
allowed to come until you convince me to break your cherry. After a couple or
three hours of this kind of stimulation, I'm sure you will beg very prettily for
my cock. Now let's go find some dinner."
Bobby led the two girls to the kitchen. Along the way, Amy said, "Can I ask
something?" When Bobby told her it was OK, she said, "When can we get dressed?"
Bobby's answer surprised both of the sisters. "I've been thinking about that.
You won't be allowed clothing of any kind as long as you are virgins, and even
when you aren't, you will have to earn the privilege of wearing clothes. It may
be weeks. If I were you two, I'd get used to being nude. Luckily I have the
secret passages, so you will be able to move around unseen if necessary. I
don't want anyone else seeing you two naked. I don't share."
When they got to the kitchen, Bobby asked the girls if they could cook. Both
said they could cook pretty well, since their brother had made them do all the
cooking. Bobby told them to look around and rustle something up quick. They
found some roast beef and stuff in the fridge, and asked if hot roast beef
sandwiches would be OK. Bobby agreed, and a few minutes later, they had them
done.
They sat around the kitchen table eating the sandwiches and talking. Both
sisters were surprised at how comfortable they had started feeling, considering
the situation. Bobby said he was glad they could cook, because that would now
be one of their jobs, along with some cleaning. He asked how they were enjoying
themselves so far.
Amy said, "It has not been as bad as I feared when you first made me undress.
When Jim lost us to you, I thought you might be going to make us prostitutes or
something. I am still a little scared, though. I really don't know what is
going to happen to us."
Annie added, "I guess I feel pretty much the same way. You haven't hurt us, but
we don't really know you. It seems pretty OK so far. I had expected to be
raped right away. Thank you for not raping us."
Bobby smiled at them. "Well, there's no reason for you to worry as long as you
do whatever I tell you to do. I plan on keeping you two right here. I will
teach you what you need to do to make me happy, and then you just have to do it.
Now, Amy, tell me why being spanked earlier got you so hot. Do you want me to
do it again?"
Amy turned red all over. She started to speak a couple of times, but the words
just wouldn't come out. Finally, she said, "I don't know how you knew to do
that. I have had fantasies about that for years, almost as long as I can
remember. I don't know why it affects me like that. I used to think about
being spanked when I played with myself in the shower."
"I don't really know if I want you to do it again or not. It was really scary.
I don't mean the spanking. I mean my reaction. I got so aroused when you made
me undress, and then it just got worse. I've never felt like that before. I
couldn't stop myself, and then I came so hard, I thought I was dying."
Bobby looked her right in the eyes, locking his gaze with hers. She couldn't
look away. He said, "Earlier today, you called me a rapist. You thought I was
going to rape you. Was that nice?"
Amy's voice was almost a whisper. "No, it wasn't nice. I'm sorry."
"It was rude, wasn't it?"
"Yes."
"So, are you a rude girl?"
"Yes, I guess I am. I'm sorry."
"Is that what good girls do, being rude to their host?"
Suddenly Amy couldn't breathe. Her chest felt like something was tightening
around it. His eyes were still locked on hers, and she was shivering and
sweating at the same time. He said, very quietly, "Answer me, Amy."
It took everything she had left to say, "No, good girls aren't rude to their
host."
"No they aren't," Bobby replied. "So, if you aren't a good girl, what kind of
girl are you?" Annie was watching her sister with her mouth open.
Amy started to sob lightly. "I guess I must be a bad girl."
"If you're a bad girl, what should I do with you?"
"Please don't make me say it, please." Bobby just waited. Amy was sobbing
louder now. She took a shuddering breath and said, "Bad girls should get
spanked. Please spank me."
Bobby stood up and took her hand. He led her to his bedroom and sat on the edge
of his bed. Then he pulled her across his lap. This time he didn't rub her
clit or pussy at all. He just started spanking her very gently, but gradually
increasing both speed and firmness. Soon his hand was leaving red prints, and
her bottom was glowing. Bobby kept a steady rhythm, never letting up, and Amy
felt herself getting more and more sexually excited.
Finally, she couldn't stand it, and started begging. "Please make me come.
Please. Please. I need to come so bad. Please help me. Please make me come.
Please. I'll do anything you want. I will. Please make me come." She was
sobbing and begging and writhing on his lap.
Bobby suddenly slid his other hand under her and started flicking his fingers
over her clit. "OK, Amy, come for me right now." It was like she exploded off
of his lap. Bobby wrapped his arm around her to keep her from falling and
rolled her backward onto the bed, landing with his face between her legs. When
his tongue hit her clitoris, she wailed, an inhuman, primal sound, and her whole
body went rigid. Her muscles were twitching with spasms, and she wailed and
sobbed as the mind-wrenching orgasm just went on and on and on.
Bobby reached up and rolled her nipples between his thumbs and fingers. Her
back arched as the orgasm reached a new level, and suddenly she couldn't breathe
at all. Then everything spun down into black again, and when she came to her
senses, she was lying on the bed cradled in Bobby's arms. He said, "That worked
pretty well. In a day or two, I'm going to do that and you are going to beg for
my cock. Imagine how it's going to feel when you are in the middle of an orgasm
like that and I shove it up your pussy."
Amy could imagine all too well. Suddenly, she couldn't wait. She knew she'd
beg for it whenever he was willing to let her.
Annie was still in shock. She had followed them to the bedroom, and the power
of her sister's orgasm had frightened her. What scared her more was that she
was tempted to tell Bobby her own fantasies, and she didn't know where that
might lead. What scared her even more was that her current situation was very
close to her fantasy.
An hour later, Bobby left Amy sleeping on his bed and led Annie to the living
room. He sat in a large leather armchair, and told Annie to kneel at his feet.
Bobby knew she was a submissive, like her sister Amy, because of how easily she
had come over and over in the rec room earlier. Now he just needed to find what
really put her over the top.
"Tell me, Annie, do you dream of being spanked, too? Or maybe it's something
else? Tell me now."
Annie had really known it was coming, but it still caught her by surprise. "I
can't... maybe sometime, but not now. Please."
Bobby caught her eyes in that gaze neither sister could look away from. "Never
say 'no' to me. If you don't tell me now, I'll get a riding crop and whip you
until you do." He saw Annie's eyes freeze with fear, and her breath suddenly
got ragged. He said, "Wait right there," and got up and left. In a minute, he
was back, and he was carrying a black riding crop. He went to the stereo and
put in a CD. When the music started, he told her, "Get up and dance for me.
Make it good."
Annie's eyes were like saucers. She practically stumbled to her feet, and
started to sway to the music, trying to get the rhythm so she could dance. She
couldn't tear her eyes from the crop in Bobby's hand. After a moment, he came
over to her, and pulled a blindfold from his back pocket. He led her into an
open area and put the blindfold onto her, and then told her to start again.
Annie finally started to really dance, but Bobby paced around her telling her
she would have to do much better if she was going to please his men. When he
said she would have to please his whole crew, she was so startled she gasped out
loud. Bobby caught it instantly and switched to a pirate theme.
"You landlubbers are all alike. None of you can dance a lick. If you don't
improve, I'll have my bosun string you from the mast and whip you bloody.
Unless your daddy ransoms you, you'll belong to my crew, and they're a cutthroat
lot, so you better please 'em." Then, as he walked around her, he started
flicking her with the crop. Across her butt, a nipple, her belly, even her
pussy, she never knew where it would strike next.
The music, her dancing, the crop, his words, all became a blur as she fell
further into her pirate fantasy. She could feel the arousal running down her
thighs. Then she heard herself speaking. "Please, Captain, don't give me to
your crew. I'll learn to please you. Please give me a chance." Bobby was
slapping her faster and harder with the crop, and she was getting dizzy with the
need to come. She started begging him.
"Please, Captain, make me come now. I need it. Please. Please. Do whatever
you want, but please let me come."
His voice snapped at her. "Down on the floor and spread your legs, wench.
Now!" Annie quickly lay on her back and spread her legs wide, wondering what
was next. The crop answered her, slapping against her pussy. Over and over it
fell, as Bobby spanked her pussy with the flat leather of the crop end. She
never thought of closing her legs. She just arched her back and moaned. Her
orgasm took her with no warning, and she screamed.
The crop continued to fall a few more times, pushing her higher and higher, and
then was suddenly replaced by his tongue. Bobby had to grab her hips to control
her as she bucked, and then, like Amy, her screams turned to wails as the power
of the orgasm swept over her. It seemed to last forever, and then she was on
the sofa. Amy was wiping her forehead with a cool rag, and Bobby was gently
stroking her body with his hands, mumbling words of comfort to her.
When she had come back to herself, she smiled at him to let him know she was OK.
He smiled back and said, "In a couple of days, you are going to beg that Captain
for his cock."
"Yes, I will," was all she said.
Amy was grinning at her. "I guess he figured out the pirate thing, huh?" Annie
started to laugh, and it felt good. She couldn't remember ever feeling this
good. Pretty soon Amy joined in the laughter. Both were thinking about sex,
and neither could believe they were aroused again already.
Bobby told them to follow and led them to their room. He told them to sleep
well, because they would be busy tomorrow. They had to learn to please him.
Both the sisters were asleep almost before their heads hit the pillows, and the
dreams were very sweet indeed.
So much for day one. Let me know if you want to read what happened the next
day. Oh, and just a quick warning so you won't be disappointed. I'm not really
into incest. It just doesn't happen to be one of my kinks, so don't look for
the sisters to do each other.
