Wall Street Pimp: Back Door Deal {Pan} (MF, anal) pt. 04

By Pan

2004/09/23

Max bought two more sessions with Shannon that month.  Both 
solicited by Shannon.  She called him up and offered 
herself enthusiastically for sale.  Shannon enjoyed the 
sex, and only really had Max as a client.  She enjoyed the 
money too, and purchased new sporting equipment for 
herself.  It was a win-win setup for the two of them.

Shannon wasn't Max's girlfriend.  He didn't have to call or 
take her out every night.  After the ball park he just had 
her come to his apartment for the night.  Shannon was there 
to get fucked, which she enjoyed, and then to go home when 
Max was done with her.

The scholarship Shannon banked on was being cut back.  She 
appreciated the extra money, and thought that Max was a 
nice guy.  He wasn't going to abuse her, and thought that 
he wouldn't make her do anything that she didn't want to 
do.  During their last session Max had wanted to have anal 
sex, but she wasn't ready and he respected that.  Shannon 
found him great in bed.  Her body was getting use to him, 
and she started to be able to control her orgasms better.  
Instead of anal sex, Shannon did all of the work during the 
last session, letting Max relax as she straddled him 
several times that night.

When the next month came, Nina called.

"Hello, Mr. Han," she said.  "I'm here with your rent 
check.  Can I come up?"

Max buzzed her in, and in a couple of minutes Nina stomped 
in on knee high black boots.  They thudded across Max's 
hardwood floors with anger.

She dug into the pocket of her denim mini-skirt, and pulled 
out an envelop which she threw onto Max's couch.  Max 
pulled off his reading glasses while he stood behind his 
desk to look at the girl with angry full lips.

"Here is your check, Mr. Han," she said crossing her arms 
below her breasts which stood out under her green cardigan 
sweater.  "You will find that all of it is there."

"That's good..." Max said carefully.  "Thanks for your 
prompt payment."

"I'm glad you're having so much fun with Shannon," she 
said.

"Yeah, I am.  Are you okay with that?  Wasn’t it your idea 
for us to meet?"

"It was.  But now that you have so much fun with her, you 
don't need to speak to me anymore?" Nina said walking over 
to Max's desk.  "I thought we were friends?!"

Max was starting to understand.  And his fears were coming 
true.  Nina was a complicated girl, he thought.  He didn't 
know what to make of her.

"Look, Nina," Max said with a little anger in his voice, "I 
think you're great to be with, and if I had known you 
wanted to get together, I would have called.   Trust me, I 
enjoy seeing you.  You're a sexy, fun, woman. But if you 
don't believe that, and want to be a little girl about it, 
then I don't have time for it."

Nina looked into a corner chewing on Max's words.  Her face 
softened, and closing her eyes she took a deep breath.

"I apologize... Shannon tells me about your time together, 
and I just thought you had forgotten me.  I think you're a 
gentleman, which is why I recommended you to Shannon."

"Don't you have Antonio... to spend time together, and not 
have to miss the company of an old man like myself?"

"Again, I don't think of you as being that old... Max," 
Nina said using his name for the first time.  Max smiled at 
that.

"And just because I have a boyfriend it doesn't mean I 
can't have 'friends'.  I am sorry for being upset."

Nina stepped up to Max and rubbed his penis through his 
slacks.

"Is there anything you want me to do to make it up to you?"

"You don't have to do anything.  If you want we can go out 
to dinner."

"But I want to do something.  We should order in, and you 
should tell me what you want."

Nina took off her heels, threw her purse on the couch, and 
walked over to Max's fridge to peruse his takeout menus.  
She unbuttoned the lower buttons of her sweater to rub her 
smooth stomach.

"This needs to be fed."

They ordered Chinese, and Nina lay on the couch, with her 
legs splayed wide enough to show her hot pink panties.

"Shannon said you have made love to her.  And she said that 
you were wonderful."

"Shannon's kind.  And Shannon was really good too."

"I want to give you an equal amount of pleasure, Max.  What 
is your heart's desire?"

"Would you like to make love?"

"Sorry, but I cannot let you have sex with – no intercourse 
in my vagina," Nina shook her head with remorse.  "I cannot 
cheat on Antonio."

"Forgive me if I'm not getting something, but didn't we 
have oral sex?"

Nina laughed and rolled over to her stomach.  Max, sitting 
on the chair near her, watched the young girl shift her 
round butt into the air.  Max could now look down her green 
sweater and saw no evidence of a bra, just Nina's breasts 
squeezed against her and the leather sofa.

"I learned how to pleasure a man with my mouth when I was 
ten years old," Nina said startling Max.  "It is quite a 
simple thing.  Like kissing my father or brother.  When I 
kiss them, I do not 'cheat' on any boyfriend I might have.  
Antonio is the only man that can make love to my vagina.  
He should be happy with that.  It is a Spanish 
sentimentality.  Not everyone thinks that way, but I do."

"Does Antonio?" Max asked.

Nina put a finger to her lips to signal silence.

"Okay, I'm okay with whatever you're comfortable with.  
Dinner and the evening together would be fine."

"No.  Not acceptable.  Hmmm... would you like to make love 
to my anus?"

Again Max almost fell out of his chair.

"Uh.. absolutely," he said unbelievingly.

Nina’s smokey blue eyes didn’t even blink.  Most girls 
would be squeemish at best when proposed with anal sex, but 
Nina just brought it up as if it was as casual as a peck on 
the cheek.

"Do you have any tequila?" she asked.

"Yeah, I have some Cuervo," Max said getting up for his 
liquor cabinet.

"You're bigger than Antonio, so it's going to hurt at 
first."

"Are you sure you want to do this?"

"Yeah.  I should be able to take it.  After I get use to 
you back there, I'm sure I'll enjoy it."

Max poured a shot for Nina and himself.  She took it down 
straight, without a flinch.  She pounded the glass back 
down on the coffee table and pointed at it.  Maxed downed 
his shot and filled two more, but before Max could reach 
for his, Nina took the both, one in each hand.  With two 
tosses of her head, she threw both back with ease.

"Tres bien," she said grinning at him and wiping off some 
Cuervo running down the corner of her mouth.

Nina tried to stand from the couch, but stumbled on the way 
up.  Max caught her in his arms and propped her up.   Her 
lips sought Max's out and they kissed for the first time.  
The Spaniard smelled of lavender from her dark hair and she 
tasted like peaches.  Maybe something in her lipstick, Max 
thought.

Nina undid the button and zipper to her denim skirt, and it 
fell around her feet.  Max gently squeezed her ass cheeks 
with both hands.  Where Shannon was firm and athletic, Nina 
was all smooth and soft-like a feathered pillow.

"Touch me between my legs," she slurred into Max's ear.  
"Touch me everywhere."

Max obeyed and sent one hand down the back side under her 
panties, and the hand down the front of her panties.  He 
had a finger go into each orifice, one was a tight hole and 
the other wet and warm.

Nina then unbuttoned her sweater while she was prodded 
below.  Max moved one hand to fondle a breast while the 
other continued to massage her anus.

"Wait!" Nina reached down to her purse - while Max's finger 
was still in her - and pulled out a small bottle of KY.  
"Show me to your bed, Mr. Han."

Max then picked the intoxicated girl up producing a giggle, 
and walked her to his bedroom.  Max's bedroom had spacious 
vaulted ceilings, and a large king sized bed with four 
walnut posts.

Max laid the girl on the bed and pulled off her panties.  
Nina's complexion was dark, because she was Spanish, but 
Max could tell that her face and chest were flush with the 
Cuervo, and she squirmed in her open sweater from the heat.  
Max took off his clothes and climbed into bed with her, and 
situated himself between her legs.  She opened up wide for 
him holding out the bottle of KY for him.

"Please lubricate me," Nina said sweetly.

Max first placed a pillow underneath her pelvis to raise 
both her vagina and anus up to a good angle.  Nina kept 
both legs spread out and up giving him full access to her 
pussy and anus.  Nina did not shave her pubic hair, so she 
had a little bush of dark brown around her vulva, but her 
anus was a clean little hole.  Max squirted some jelly onto 
one finger, and then felt Nina hands reach down and wrap 
around his penis.  She stroked him and moved dangerously 
close to positioning him into her vagina.

"Dammit," she cursed.  She then said something in Spanish - 
something Max had a hard time making out - about wicked 
thoughts.  "Please make love to my anus..."

Max started spreading the jelly around her anal sphincter, 
and then into her hole with his fingers.  First one, and 
then two fingers.  Nina was surprisingly clean inside, and 
Max suspected that she had washed herself before coming.  
Next Max greased his own penis with the jelly.  Nina helped 
with a few slathers of her own.

Max then placed the head of his penis on her anus.  Nina 
looked down curiously, and grabbed her own legs to keep 
them wide apart.  Max put one hand around his shaft so that 
it would stay on her anus, and then leaned into Nina with 
his body weight.  She gritted her teeth in pain and 
concentration as she felt him start to force her open 
farther than two finger's worth.

"Aaaa!" she screamed as the tip of Max's penis forced her 
anus open.

"I'm sorry," Max whispered and was ready to pull out."

"No... keep going... make love to me, Max... make love to 
my anus!" Nina grunted.

Max listened in case Nina asked to stop, and continued to 
push.  Nina groaned in more pain, but Max kept pushing.  
Nina's asshole was tight, and the pressure felt great on 
Max's penis head. 
When Max was halfway in, Nina was panting and sweating 
buckets.  But she made no signal to stop.  Max leaned his 
body on top of Nina.  She arched her pelvis up so that it 
was almost vertical and her feet spread back towards her 
head.

Max got three quarters of the way in, and didn't think he 
could get any deeper.  He withdrew until only his head was 
resting in her.  She sighed in relief, and even Max took a 
breath from the exertion.

After a moment, Max pushed back in.

"Mi culo!" Nina grimaced and moaned.

The second time was easier than the first, but her anus 
still resisted - which was great, because Max loved it.

"Geez, that's a tight hole," Max said.  "You're so fucking 
sexy."

The motion started to get smoother, as Max's sweat, precum, 
and the KY made its way all around Nina's asshole.  She 
didn't stop grimacing in pain, but her moans quieted down a 
little as Max reached a rhythm fucking the nineteen year-
old asshole.

"Ah... mi Dios!" Nina moaned.

Max rocked into the girl until he couldn't hold it back 
anymore.  It might have only been a couple of minutes, but 
the sensation overpowered him and he cummed right down her 
anus.

After Max pulled out Nina laid there panting - legs still 
splayed wide - with cream trickling out of her anus.

"Was that enjoyable?" she asked with a smile.

"Thoroughly, my sweet."

The phone then rang.  Food had arrived.