First Time for Everyone

By Kitty

 
Greg was a little anxious when he showed up at Jamie and Lisa’s house.  
He was about to do 3 things he had never done before, four, if you 
count the fact that he had never actually met them face to face.  He’d 
gotten to know them very well talking to them on ICQ and on the phone, 
had even listened in when they made love.  He reminded himself  that 
they were going to be doing things that they had never done before.   
That made him smile. 
 
Jamie and Lisa waited for Greg to arrive.  They reminded themselves that
just because his name was the same as their rugby friend, they thought 
briefly about whether they could trust him for sure.   “It’s too late 
now,” Lisa said, “he’ll be here any minute.”   Jamie nodded slowly, 
“That’s true but we can always kick him out.”      They looked at each 
other, and laughed.  They were looking forward to what was going 
happen.   Lisa and Jamie were both going to fulfill fantasies. 
 
Lisa’s was a deeply hidden secret until she met Greg.  She had wanted to
fuck a man up the ass.  She wanted to know what it would be like to 
have a man submit ultimately to her.   She had kept it hidden, until 
she met Greg, certain that it would never come true.  Now it was and 
she could hardly wait.   The only way they were able to make the 
fantasies come true was to have the guys be subs while she played a 
dominatrix. 
 
It was a role that she had never played before, but she was willing to
give it a try.  She had been reading stuff for months.  Any story she 
could find on the subject.  She knew that Doms cared as much about 
their subs pleasure as getting their own.  So she made sure she knew 
what each guy wanted and what they ultimately would not do.   She knew 
that Jamie wanted to suck cock but wasn’t’ interested in anything anal. 
 Greg wanted to have his cherry ass broken in but wasn’t interesting in 
sucking anything but her.  So she would make them both happy. 
 
Jamie was thinking about the night ahead.  He knew that she would make
him suck cock.  A fantasy he’d had on his mind for a while now.  He 
also knew he was going to watch her fuck this guy’s ass.  He wasn’t 
sure what that would be like, but that was Greg’s fantasy.  As well, 
apparently, as Lisa’s.   He’d never known that before.  She asked for a 
strap on for her birthday, so he bought it. 
 
He had taken along his good friend Greg, the rugby guy.   He had told
him it was so she could fuck women when they were playing with them.  
Which was true, but it wasn’t the first use it was going to get.   
Greg, the rugby friend, had even bought her two dildos for the places 
for the wearer.   He had wanted to object at first, after all, that is 
personal, but then he thought of all they had done together.   So he 
said nothing and let Greg by them. 
 
They were both startled out of their thought by the sound of a car door
slamming, seconds later they heard the knock on the door.  Jamie 
motioned for her to get it.  She took a deep breath and opened the 
door.   She smiled when she saw Greg, relieved that he was what he said 
he was.  Six feet, dark hair and about the same build as Jamie. 
 
Jamie thought that Greg was fairly good looking, if he was any judge of
men.  He decided that Greg had a nice profile too.  “Profile” was 
Lisa’s euphemism for the male pants package.  He wondered what Greg 
looked like naked. 
 
Greg was happy that Lisa had not underplayed her curves.  She was about
perfect, he thought.  Everybody liked Marilyn Monroe’s figure and Lisa 
had that right about herself.  She was wearing skin tight black jeans 
and a barely there black tank.   She looked hot, black was a great 
color for her. 
He stepped into the house and extended his hand to Jamie.  “Nice to
finally meet you face to face.”  Jamie shook his hand firmly, smiling 
at him, “Same here, been looking forward to it.  We should have fun 
tonight!” 
 
“Gentlemen, it is time.  I have clothes for you to wear in the bedroom. 
Go put them on. “  Lisa pointed toward the bedroom.   The guys looked 
surprised, they thought they would have a drink first.  “So, you 
thought you’d have a drink first, eh?  Not a chance.  Go.  Change.”  
They slowly walked into the bedroom. 
 
On the bed they saw 2 outfits, side by side.  Pants and a shirt, no
jockeys.  The only difference between the clothes was that one outfit 
was red and one was black.  They put them on and discovered two things. 
One, the pants were precisely one size too small, making their profiles 
bulge.  Two, the shirts only had buttons half way up.  They looked 
silly, they both thought.   They looked like a couple of male hookers.  
They laughed at each other. 
 
A mocking voice came from the doorway, “Did something amuse you,
children?”  Both men jumped and shook their heads guiltily.   Good, 
Lisa thought, they’re already getting into it.  “Here are the rules.   
You do exactly as I say, when I say it, and you call me Mistress Lisa.  
You may only speak when spoken to.  Understand?”  Both men nodded.   
“Pardon me? I don’t think I heard you!” 
 
“Yes Mistress Lisa!”  Both men barked it in unison.  They felt like they
were at boot camp, not in for fun.   Lisa was going to change that 
attitude in a hurry.  They didn’t know that though, they were beginning 
to regret it. 
 
“Now, gentlemen,” she sneered the word,  “You asked for me to be
dominant in this situation, did you not?” 
 
Both men started to nod, then remembered, “Yes, Mistress Lisa!” 
 
“Well, then, that’s what I’ll be.  No regrets, no questions.  First,
Greg, go and get me a drink.  A screwdriver, and it had better be 
right!   Jamie, you massage my feet.  I need to relax.”  Greg ran into 
the kitchen and fixed her drink.  Jamie removed her shoes and began to 
rub her feet. 
 
He successfully rubbed one foot and had started on the other when she
impatiently pulled her foot back.  “Did I do something wrong Mistress?” 
Jamie asked.  She glared at him for speaking, she thought about 
smacking him but decided on a different punishment instead. 
 
“For speaking out of turn Jamie, you will be the last to cum.  You will
make sure everybody else has cum before you do.”   Lisa smiled at him, 
enjoying the crestfallen look.   Greg returned with her drink and she 
took a sip.  “Perfect my dear,” she decided to make him her favorite 
for the night.  “You may kiss me.” 
 
Jamie watched as Greg leaned over his wife  and gently placed his lips
over hers.  Greg did it quickly, unsure of what she wanted.   As he 
started to pull away she grabbed his head and thrust her tongue deep 
into his mouth.  He parried with us and a tongue war began.  She kept 
him there for several minutes, long enough to make Jamie squirm. 
 
Jamie was thinking that this night might not be as much fun as he
thought.   He decided to not put a stop to it, and see where it went.  
He knew he could stop it if he wanted to. 
 
Greg, meanwhile, had developed a major hard on.  Lisa’s kissing
technique had thoroughly turned him on and it was all he could do to 
stay in his role. 
 
Lisa was watching them as they thought.  She could see Jamie’s
reluctance and Greg’s obvious hard on.  It was straining against his 
pants, trying very hard to get out.  She decided to move it to the next 
level.  She stood up and walked into the bedroom. 
 
As she walked, she thought about what she was wearing, a purple lace
teddy under tight black jeans.  She wondered how best to get her 
clothes off.   She thought that Jamie should take off her jeans and 
Greg should work on her teddy. 
 
When she looked back she saw that the men were still in the same spots. 
She snapped her fingers and pointed to the floor beside her.   They 
scrambled to get where she was.  “Unless I say otherwise, you move when 
I do!”  They looked at each other, behind her back and grinned.  “Yes, 
Mistress Lisa!” they both snapped out. 
 
She walked into the bedroom and stood in the middle of the floor.  She
held her arms out and commanded, “Undress me!  Jamie, you remove my 
jeans and you take off my underthings.”  She pointed at Greg.   They 
leaped to do her bidding.  After Greg looked her over, he realized that 
he would have to wait for Jamie to remove her jeans. 
 
Jamie undid the snap and zipper and began to pull the jeans down.  She
glared at Greg, “What are you waiting for?”  He jumped and began to run 
his hands over her upper body, looking for away to do as she asked.  He 
found that the straps slid down over her shoulders and started there. 
 
Lisa closed her eyes, enjoying the feel if her jeans sliding down her
legs.  She slipped an arm out of one strap, then the other.  She was 
almost free of her clothes.  Jamie lifted one foot so she could slide 
her foot out.  Greg pushed her teddy past her breasts and she sucked in 
her breath as cool air brushed her nipples. 
 
Out came her other foot and Jamie tossed her jeans to one side.  He
stayed on his knees, waiting.  Greg slipped the teddy down her legs and 
off her body.  She stood there, gloriously nude, and let them admire 
her. She knew she had a few places that models might cal flawed, but 
she also knew she was sexy as hell and it didn’t have everything to do 
with the way she looked. 
 
She basked in their attention a moment longer then moved again.   She
stretched out on her back on the bed and said “Make me cum!”  They 
looked at each other, wondering what to do.   She sighed, exasperated.  
“Take some initiative!  Jamie, you know what I like!  Show him!” 
 
They walked over to the bed and kneeled on either side of her.   At her
command they nibbled, sucked and licked till she screamed to a crashing 
multiple orgasm. 
 
When her breathing returned to normal, almost, she told Jamie to get her
new toy.   Jamie walked over to her dresser and pulled out her strap 
on.    Greg’s eyes widened at the sight of it.   It has places for 3 
dildos.  An anal, a vaginal and the one on the front.  The anal dildo 
is 5 inches long and an inch around.   It’s the smaller of the two.  
The other one is  7 inches long and 3 inches around.  The same size as 
the one strapped onto the front. 
 
They watched as she lubed up the dildos, the ones for her, and inserted
them.  They groaned as the dildo slid in her wet pussy and moaned as 
she screwed the other up her own as.   She finished strapping it on and 
sat on the edge of the bed.  “Come here.  Both of you.”  They walked 
over to her unsure of what to expect. 
 
When they were close enough she grabbed both their dicks in her hand. 
She had decided to warm them up to their fantasies by blowing them 
both.  She stroked Jamie while slurping Greg’s 6 inches into her mouth. 
   All the way in, all the way out.   She did it until he almost fell 
down.  Then she did the same to Jamie. 
 
When Jamie was panting with the need to cum she pulled him to his knees.
  "You are now going to wrap your lips around this cock in front of 
you.   Open your mouth,” she commanded.    Jamie opened his mouth and 
leaned forward when she told him to.  She guided Greg’s cock to Jamie’s 
mouth and told him what to do. 
 
“Open your throat, relax and go with it. “  She put her hand on the back
of his head and steadily pushed him onto Greg.   Only when Greg’s 
entire length was in his mouth did she let go. 
 
Greg was in heaven.  Jamie’s mouth was the hottest mouth his dick had
ever been in.   He watched as Lisa began whispering in Jamie’s ear.  He 
felt Jamie’s tongue start to move.  Jamie slowly moved his head back 
dragging his tongue over the bottom.  His head slipped out of Jamie’s 
mouth and he gasped as he felt the cool air on himself again. 
 
Lisa whispered more instructions and Jamie’s tongue swirled around his
head.  He licked the precum of and made a sound of appreciation.  He 
lifted Greg’s cock with his hand and looked at his balls.   Jamie 
glanced at Lisa and she nodded.  He leaned in and slowly tasted Greg’s 
sack.  Rough, but not unpleasant.  He tongued them more and had the 
satisfaction of hearing Greg moan. 
 
Jamie tongued him till Greg pushed him away slightly and then he wrapped
his mouth around the cock before him again.  He made his mouth a vacuum 
and  moved it up and down Greg’s length.  As he got started he felt 
Lisa take his length in again.    He moaned around Greg’s cock as she 
sucked on him.  He felt around with his free hand until he felt her.  
He traced her body to her head and tangled his fingers in her hair. 
 
Lisa immediately stopped what she was doing.  “No, you don’t!  You don’t
get to do things on your own! “  She slapped Jamie on the ass.   “How 
are you feeling Greg?”  He stuttered several times, gasping for air 
before he could tell her that he was going to cum any minute.   She 
said no.    She moved Jamie off of him and told Jamie to get the lube. 
 
She told Greg to get on his hands and knees on the bed.  He did,
hesitantly.  Now that the moment had arrived, he was unsure.   She 
warned him that it was going to hurt at first.  She ordered Jamie to 
lube Greg’s ass while she did the same to the dildo.   He chose to do 
it by licking him.   Greg started as Jamie’s tongue came into contact 
with his ass.  Jamie slowly licked around the outside, up and down 
Greg’s crack.   He moistened the skin all around and then wiggled his 
tongue inside. 
 
Greg tightened up at first, then relaxed as he realized it felt good.  
Jamie got him good and wet then inserted a finer.  Greg moaned at this 
invasion, unsure if it felt good or bad. He settled on good.  When he 
had relaxed, Jamie added a fingered.  Jamie fucked him with those two 
fingers until Greg moaned.   Then he added a third.  Greg’s ass was 
stretched out, almost ready for Lisa. 
 
She tapped Jamie and told him to move.  She got on her knees behind
Greg, talking softly.  “Jamie did a great job loosening you up, now 
it’s my turn.   You’re going to feel some pressure I’m going to put 
this cock at your opening.”  She pushed his shoulders down so that his 
ass was sticking way up.   She settled the tip of her cock at his anus 
and slowly pushed. 
 
“I’m putting it in you now.  It’s going in slowly, we’re almost past the
head.” 
 
Greg whimpered, it hurt like the dickens.  “You tell me if you want me
to stop,” she said.  He moaned but managed, “Keep going.”   She told 
him to stay relaxed and she made Jamie lie between their knees and 
suck Greg.  “Don’t you let him cum!  Just help him forget about the 
pain a little.” 
 
Jamie sucked on the tip of Greg’s head and was rewarded with a moan.  
He increased his efforts.  His cock throbbed too.  He was in desperate 
need of cumming.  His hand strayed to his cock to stroke it.  And it 
got slapped.  “It is Not your turn!” 
 
She had finally gotten the head into Greg’s ass and stopped.   The
blinding pain he felt was subsiding.  She talked to him gently.  
Reminding him that the pain would go away and it would feel good.  
Pretty soon, it had stopped and he moved against her.   She took that 
as a sign that he wanted her to continue. 
 
She pushed further into him, slowly and just as slowly pulled back out. 
He moaned at the loss and she thrust it back in.  Jamie continued 
sucking on him as she fucked his ass with increasing vigor.  He felt 
vibrations as she turned on the vibrator in her toy and knew she would 
cum again anytime.  He didn’t want it to stop so he begged her to keep 
going.  She slapped his ass in response and fucked him harder. 
 
Jamie could feel Greg’s cock tighten and sealed his mouth around him.   
He wanted every drop.   “Oh God!!” Greg screamed, “I’m going to 
explode!”  Lisa moaned and fucked him harder.  She was sweating, her 
hair flying as she fucked him for all she was worth.  She could feel 
her orgasm intensifying.   She screamed as it ripped through her and 
Greg spunk exploded in Jamie’s mouth. 
 
He swallowed every drop, licked him clean, and moved out from under him.
He then begged Lisa to let him cum now.  She pulled out of Greg and 
ripped that strap on off.     Greg collapsed on the bed, panting.  With 
her orgasm still vibrating through her she  pounced on Jamie.  “Fuck 
me,”  she growled. “Fuck me hard!”   She threw herself on her back, 
pulling him on top of her. 
 
He plunged in to her and thrust into her hard and fast.   Her tits
jiggled and he wrapped his mouth around one of her nipples.  He bit her 
for punishment.   And she cried out.  She kept cumming, cumming like 
she never had  as he screwed her.   He thrust hard into her one last 
time and bellowed as he came. 
 
She dug her fingers into his ass and tried to swallow him with her cunt
as one last wave of pleasure washed over her.   They both almost passed 
out.  They looked over at a sleeping Greg and laughed.  Jamie lay his 
head beside her and they slept for awhile. 

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