Date: Tue, 23 Apr 2013 05:36:14 -0700
From: Kitty and Bear
Subject: Friends with Benefits

It was late Saturday evening when David and Eric, shuffled home to David's
place.  They were returning from a party at the campus pub and were
slightly inebriated.  Eric had never fit in with the popular, party-going
crowd in high school, but now hoped it was different in university.

David had a nice apartment off campus, and Eric enjoyed the freedom of
hanging out with his new friend away from his mother's prying eyes.

They met in their sociology class, and became friends when paired up
together on a project.  David had an engaging manner that allowed Eric to
take the lead on the project.  Another way of expressing it would be that
David left Eric to do all the work.  Eric barely noticed as he was used to
being taken advantage of.

He was ecstatic when David invited him to this party.  Being part of a
group would be a new experience, and he would be going with a tall,
well-built, masculine guy; exactly the time which bullied him in high
school.

He still didn't quite fit in, and clung to David's side most of the night.
He couldn't hold his liquor very well, and was drunk after a few beers.

David seemed unimpressed with the party for his own reasons.  Eric couldn't
fathom what bothered David as he seemed to be welcomed into this social
clique.  However, he readily agreed to leave with him and was excited to
visit David's place.  It must be so wonderful to have your own space.

They settled into the rec room, and flipped through the late night TV
offering.  The only thing they came across of any interest was a blue
movie.  This rather shocked Eric as he could never watch adult films with
his mom and sister around.

David had the opposite reaction.  "This is pretty tame, kind of like those
stuck up bitches tonight."

"What do you mean?" Sensing he was now going to learn why David was bored
at the party, his curiosity was piqued.

"Those girls... Oh excuse me, young ladies," he said sarcastically,
"... They hardly give you the time of day.  Either that or they are obvious
gold diggers.  Not one of them will put out."

Eric nodded in agreement, when in reality he had no idea what David was
talking about.  Girls had always treated him with disdain; the nerdy kid no
girl would hang out with.  Eric seriously doubted that David suffered the
same affliction.

"How open minded are you?"

Eric wasn't certain how to answer.  He was fairly liberal minded, but still
being a virgin, he didn't have the life experiences to know for sure.  "I
guess I'm fairly open minded."

"If I put on something really freaky, do you promise not to tell anyone."

Now this was getting really intriguing.  "I promise."

David went to his bedroom and returned with a collection of DVDs.  They
were obviously copies as there were no cases or labels on the discs.

The video appeared to be your standard porno, with a ridiculous plot, a
buxom brunette in a revealing outfit, and a muscular guy already sweating
from his work.

Eric had accessed some videos like this on his computer when his mom wasn't
around.  Yet it still felt weird to be watching them with another guy.
David was really starting to get into it.  He had unbuttoned his fly and
was rubbing the bulge in his underwear.

Eric tried not to look at David, and was uncertain how he should react.

The woman on the screen was now topless and the man was sucking her
nipples.  Her hand gripped the man's cock and stroked him furiously.
Exactly on cue, and quite predictably, the woman knelt down and began
sucking him off.

David was really starting to get into it.  He now had his dick in his hand,
and was slowly jerking himself off.

Eric was really getting freaked out.  He debated saying something.  Yet at
the same time, he couldn't help looking at him.  David's cock was huge; as
big as the one on screen.  Eric had no compunction to pull out his cock,
and was now more reluctant considering how small his cock was in comparison
to David"s.

On screen, things suddenly took a twist.  The guy pulled down the woman's
panties as they kissed.  Yet as the camera panned down with the man's hand
reaching between her legs, he did not stroke her pussy.  Instead, he
grabbed her cock.

Eric sat forward; stunned. He had watched some tranny porn on his computer,
actually quite a bit really.  However, he had never expected a hunk like
David to like shemales.  David had a wide grin on his face as he observed
Eric's reaction.  His cock was firm, and still being stroked furiously.

The tranny on the screen was bent over, and the man positioned himself
behind her spread out legs.  He then slowly penetrated her ass, and began
fucking her hard and deep.  The tranny gasped with each thrust.

David was sitting back, knees spread, and jerking hard on his cock.  Eric
even spotted some pre cum on the tip of his penis, and unconsciously licked
his lips.  His own cock was now hard and strained against his pants.

Eric wasn't certain what was coming over him.  Perhaps it was the alcohol,
or his favorite type of adult video with a hot tranny, or just the bizarre
situation with David jerking off beside him, but he was getting really
horny.  Not just horny, but turned on by David and his huge cock.

He couldn't tell what compelled him to do this, but he knelt down and began
to suck David off.  David ran his hands through Eric's hair and just
enjoyed the moment.  Eric was really getting into it, imagining all those
videos and photos of trannies and crossdressers devouring a throbbing cock.
He loved the hardness with the smooth touch which penetrated deep into the
throat.  He could hear the man on screen grunting with his own orgasm.
David was not far behind.  Eric tasted the first bit of salty goodness, and
began to suck even harder.  David gripped his hair.  "Oh yeahh!!  Take it
bitch."

David shot his load deep into Eric's throat, and Eric didn't miss a drop.

Exhausted and drunk, David passed out on the sofa with his pants open and
Eric kneeling before him.

Eric rose with a blush of embarrassment which no one saw.  He looked down
at David and his now softening penis.  Part of him wanted to be mad at
David for setting up this scenario.  The other part of him knew he had not
been forced, and could forgive this gorgeous man anything.  He looked back
at the TV where a new tranny was being fucked on the bed.  He slipped
quietly out the door, wondering if this was how they began.

Chapter 2

Eric's sister Claire noticed something was up right away.  "What's up with
you?  You've been acting strange since Friday night."

"You know me, I can't hold my liquor, and I got a little drunk."

"That's for sure, most of my girlfriends could drink you under the table.
But even a sissy like you can't be hungover the following day."

Eric was startled by Claire calling him a sissy.  He shouldn't have been
surprised as she always called him that.  His sister noted his reaction,
particularly the lack of his usual denial.  Sensing she was onto something
juicy, she pestered him further.

"Why aren't you returning your friend David's calls."

"Why do you care?"

"Ohhh touchy, touchy.  Lovers quarrel?" She said with a laugh.

"No!". He looked away as he said it.  "He's just a study partner, and a new
friend.  Do you think I'm not able to make friends?"

Eric was completely over reacting to her teasing, which made it apparent
something had happened.  She was tempted to torment him further, but it
seemed that now was the time to be his protective older sister.  She sat
down on the sofa next to him, and hugged him.

"What happened?"

He was caught off guard by her sudden gentleness.  She hadn't been this
nice since the years she fended off bullies at school.

"Sis, am I really a sissy?'

"Oh honey, did David pick on you."

He stared at the ground and shook his head.  "No, it wasn't like that". He
spoke so quietly she could barely hear him.

"I know I always tease you, but you are my brother, and I love you.  You
can tell me anything sweetie."

"Well David and I went back to his place after the party.  We were both a
little drunk, so I don't know how much he remembers".  Claire was listening
intently, rubbing his shoulder reassuringly.

"... Anyways, he put on this porn flick.  But it wasn't a typical porn
flick.". He was starting to sound defensive.  "It was a shemale flick"

She nodded.

"And I got horny.  Well, we both got horny.  Then I sucked him off.  I
mean, he didn't even ask me to - I just did it."

He started to cry.  "I guess that makes me a sissy now."

"Sweetie, you have been a sissy since you started stealing my clothes."

Eric sat up straight and stared at his sister.  "What?!"

"Oh please, I've known for years."

He looked down in embarrassment.  "So you think this was inevitable."

"I have imagined making you over so many times.  It always makes me
excited."

"And why should I get made over now?"

"David wants to see you again, and we both know what turns him on.  And we
both know what you have been fantasizing about for years."

"Yeah, but those shemales were hot".

"O yea of little faith," she chided.  "I'll make sure David gets a hot
girlfriend."  She curled her finger through Eric's hair and smiled at him.

He was starting to buy into all this.  Claire smiled, delighting in how
easy it was to manipulate him.

* * * Eric avoided David until the next day at class.  It was in the
lecture hall where he could have avoided him further, but instead waited
behind after class.  David walked over to him.  "I'm sorry I freaked you
out the other night.  I was phoning to apologize."

Eric smiled, consciously appreciating for the first time how nice and
attractive David was.  "I'm sorry for not returning your calls.  I've never
done anything like that before.  I guess I was a little freaked out."

"Let's forget it ever happened".  David tried to reassure him.

"Was I that forgettable?". Eric teased him.

David chuckled, startled by Eric's sudden eagerness.  "Not at all".  And
then whispering, "actually it was the best blow job I've ever had."

"Beginner's luck."

"Beginner?"

Eric smiled in response.  "Are you free on Saturday night?"

David shuffled in his seat, visibly uncomfortable.

"For a moment I thought you had done this before," Eric stated in a half
questioning manner.

"No, not really.  I mean... well there was one kid back in high school.  We
didn't date.  I just made him suck me off a few times.  But people never
knew.  I'd have beaten the shit out of him if he ever told anybody."

David evidently was just like the bullies which used to taunt and beat up
Eric in high school, only he had a secret.

"So you are worried about people seeing us together."

"Yeah, if I'm going out on a date, or to some party, its going to be with
some hot babe.  Sorry, but that's just the way it is."

Eric nodded, "Don't worry about it.  And hey, maybe we could hang out like
regular guys."

"Yeah, sure, but you better not say a word".  The implied threat was
obvious.  Then he lightened up.  "What happens if the chick doesn't put
out, like Friday night?"

A few short days ago Eric would have been terrified of the implication.
Now, he was excited.  His only response was a wink.


Chapter 3

David didn't have any plans for Saturday evening, and the two of them
planned to go to a club Saturday together.

Claire was almost as excited as Eric when she heard about it.  "Now is your
chance."

"What?!  We're just hanging out."

"You're just hanging out until David finds a hot girl.  I think you should
be that hot girl."

"David isn't going out with a sissy.  I told you, he's still in the closet,
and he'd beat the shit out of me if I outted him."

"Give me the day to feminize you.  If you don't think you're beautiful at
the end, just phone David and tell him you're feeling sick."

"And why should I let you make me over, even if you could do a good job?"

"Because if you don't, you are going to spend the evening pinning after him
in the corner of the club while he hits on every available girl in sight."

She was right, no matter how much Eric wished that she wasn't.  "What if
someone finds out?"  "Who?  Mom's on her business trip, so we have the
place to ourselves for the day.  And I promise you'll be ready before David
picks you up."

Eric stood up and paced a bit.  "OK, but no tricks.  If I don't pass as a
woman, I'm not walking out this door."

"Agreed".  She took his hand and lead him to the bathroom.

"Now, run a bath".  Handing him a razor, "... And shave all of your body
hair.  All of it!"  As Eric sat in the bath, alone with the razor in hand,
he began to have second thoughts.  Yet the other part of him felt there was
nothing to lose.  He had spent so much time over the years wearing the
clothes he stole from his sister.  Now it was time to find out if he could
really pull it off.

His sister was always hot looking, and he had envied her popularity.  If
anyone could help him look sexy, it was her.  He began shaving.

He was just finishing when his sister walked back in.

"Hey" he cried out and attempted to cover himself.

She laughed, "Don't be silly, you've got nothing worth looking at."

In humiliation he dropped his hands and finished up in the bath tub.  She
tossed him a tub of cream.  "Here, put some of this on.  It will releave
any itchiness from shaving and make your skin smoother."

He noticed the flowery scent immediately, but proceeded as instructed.  As
promised, it did make his skin feel soft.  He idly stroked his legs,
delighting in their silky feeling.

Claire giggled at him.  "I should have forced you to do this years ago."
"Ok, put these on".  She tossed him a matching bra and panties.

He put them on, feeling silly, but he had done this many times before.  The
bra had some padding which gave him some breasts.  He was then led to her
bedroom, and seated before her mirror.

"I am so glad I talked you out of cutting your hair.  Now you don't need a
wig".  She combed his hair out, trimmed it in a few spots, added some
extensions, and then began styling it.  Eric sat patiently, trusting her
judgment.

Eric's only complaint was a lack of clothes.  She dismissed this by simply
saying, "No, I like you better this way."

Claire was clearly loving this whole exercise.  It was also clear from the
way she quickly moved the process along that she had given this a lot of
thought.

Eric tried to resist having his ears pierced, as this would be permanent,
but this too was easily dismissed.  "Don't be silly, lots of guys wear ear
studs."

Next came his eye lashes, which were tweezed, and sharpened with eyeliner.
It was really coming together.  Eric was amazed by his reflection.  Once
earrings, some rouge, and lipstick was applied, the effect was complete.
With each step, he - or was it now she - was looking more and more
gorgeous; and his resistance diminished.

Next came the false nails, which were then painted scarlet red.  The toe
nails were painted to match.

Hours had passed since they had started, but they were both still having
fun.  They were even beginning to joke and gossip amongst themselves in a
way they had never done before.  It was becoming the slumber party they had
never had.

"Ok Erica, I bought a dress that I think is perfect for you."

"Erica??"

Claire pointed to the reflection in the mirror.  "Yes Erica.".

Looking back was a lovely woman with wavy brown hair, smooth skin, a thin
graceful body, long sexy legs, and beautiful blue eyes.

"Ok, Erica it is." Looking back at the reflection, he wondered out loud,
"Do you think David will like me."

Claire embraced him.  "Sweetie, he's going to love you."

The dress was indeed perfect; black with red flowers, knee high skirt, and
a long neckline.  "Oh sis, it's wonderful!" Erica squealed with delight.

"Ok, ok.  Don't get ahead of yourself," Claire chided, but was secretly
delighted in the reaction.  "You need to put your stockings on first."

It was revealing that he put them on with ease, even getting the seam
right.  As Erica was putting on the dress, Claire pulled out a pair of open
toed, high heeled shoes.  The shoes fit perfectly.  Claire shook her head
in disbelief.  "Given how much you match my size for dresses and shoes, I
can't help but wonder how many of my clothes you have worn without me
knowing."

His silence and sheepish grin spoke volumes.  She shook her head, partly
out of disgust that her things had been used so brazingly, and partly out
of amusement at her sissy brother.  "From now on, come to me, and I will
help you buy your own clothes and makeup."

"I promise." He was really enjoying the look and feel of this dress, and
felt certain he would be doing this again.

Erica wobbled in the heels initially, but quickly got the hang of it with
some tutoring from her sister.

"When is David supposed to come by, or are you meeting him somewhere?"

Suddenly, Eric had a lump in his throat.  He had forgotten that all of this
was for him, and David had no idea about any of this.  Eric had never
expected this would work, but now that he was a sexy looking woman, he was
not certain how David would react.

Claire could tell how nervous he was.  "Since you're going out to a club, I
suggest you ask him to pick you up here around 9."

Eric nodded.

"Well go on, make the call."

Eric slipped into his bedroom for his cell and called David.  Returning to
his sister's bedroom, he informed her, "David's going to pick me up around
9:30.  I told him I have a surprise for him."

"Great that gives us lots of time to practice you're walking, and maybe
some dancing.  And we'll also need to work on your feminine voice.  Let's
have something to eat first."

They proceeded downstairs to the kitchen, being extra careful walking down
the stairs, and made dinner.  They chatted throughout, stopping and
correcting Erica's tone periodically.  Later they did some touch ups on his
hair and makeup.  By 9:25 when the doorbell rang, Erica was as ready as she
would ever be.

Chapter 4

Claire welcomed David in, and exchanged introductions as they walked to the
living room.  She called out from the bottom of the stairs, "Erica, David's
here!"

David paused for a moment and then shook his head, figuring he just
misheard.  He sat on the sofa and waited.

Eric's other sister came down the stairs and into the living room.  "Hi
David, what do you think?" She did a slight turn and pose.

He looked at her like she was crazy.  She was smiling at him as if she knew
him.  He looked at her more closely.

"Holy shit!"

Erica stood nervously before him, praying that he would not walk out the
door.  "Surprise," she said softly with a shy grin.

Claire walked to Erica's side and put her arm around her.  "Doesn't she
look great."

David nodded, "yes, SHE does."

"I told you I had a surprise for you," Erica said.  His soft feminine voice
was very alluring.

"Yes, yes you did, but... Holy Shit." He really didn't know what to think.
He was completely ambushed.  However, he couldn't deny that 'Erica' looked
hot.  He was getting aroused staring at 'her'.

She stood before him, shifting nervously in her heels, as he looked over
her body.  At least he wasn't pissed, or walking out the door, which had to
be a good sign.

"OK, fuck it.  I didn't recognize you, so who will at a night club where no
one knows us." He stood up and kissed her.

Erica squealed with delight and hugged him.  Even wearing heels, she had to
look up to him.  She then gave him a long passionate kiss.

Flushed, he took Erica's hand.  "OK sweetheart, let's see how you move on
the dance floor.  I'm sure your sister didn't dress you up to be a
wallflower."

"Have fun." Kate wished them as they exited the door.

When they got to the club, Erica started to get nervous, and could see
David was also on edge.  A couple of drinks later, they started to relax.
That's when Erica coaxed David onto the dance floor.  She was now grateful
for the practice her sister had given her earlier, as she was able to move
gracefully.  She swayed her hips, and was really getting into it.  David
held her close, and she rubbed her body against him.

He whispered in her ear, as much as the noisy club would allow, "You are
being a big tease."

She whispered back, "I'm not teasing." Erica turned around, locking herself
in his arms, and tightly against his body.  She continued to dance and
sway, rubbing her buttocks against his crotch.

They were like most of the other young couples at the club; dancing and
kissing in the corner.  No one paid them the slightest attention, and
apparently no one either noticed or cared about Erica's secret.

They were both a little drunk when they left the club at around 1:00.  Yet
more than than that, they were energized and horny.  Erica in particular
had never felt this level of excitement.  As a man, he had shunned such
parties or sat awkwardly alone in the corner.  As a woman, she had danced
the night away and delighted in the attention of several men who regarded
David with envy.  Even some women complimented Erica on her dress or hair.

Yet even as the princess, she did not forget the Prince Charming who had
awaken her.  They kissed for most of the cab ride to David's place.

Once there, they quickly found themselves on the sofa where their adventure
had begun a week before.  They french kissed and fondled one another.
Erica leaned back to allow David to lick her neck and nibble her ears.  She
moaned with each caress of his fingers or tongue.

David fondled Erica's breasts, reaching down the dress and squeezing the
lace trimmed bra.  She giggled, "You know it's just a padded bra."

"I know, but don't ruin the fantasy.  And you know that can be fixed."

"Can and will be."

He paused to look Erica in the eyes.  "Wow, you're really getting into
this."

"There's no going back.  I've fantasized about this for so long.  I always
thought it was silly, or I would look ridiculous.  But now that I am here
with you, everything feels right."

He kissed her deeply.  The zipper of her dress was opened and it was
lowered past her shoulders and down her body.  He kissed his way the silky
body, eliciting gasps of pleasure as she opened up to him.

With the dress removed, Erica cuddled up next to David and slowly
unbuttoned his shirt.  She stroked his muscular chest, while he squeezed
her firm butt.  She kissed her way down to the bulge in his pants.

There was no waiting for the inevitable.  Erica knelt before him, undid his
fly, and quickly pulled his pants off.  She instantly sucked him deep.  It
was every bit as hard and smooth as she had remembered.  She gagged on it,
and came back for more.  Her lips pressed down on his shaft providing a
wonderful friction.  Long deep sucks gradually intensified until she was
madly bobbing her head in and out, and her lips never leaving the cock.

He was moaning now, and coaxing her on.  "Yeah baby... Suck it... That's
it!" He had hoped to hold out a little longer, but he soon shot his load
deep into her throat.

Erica savoured every drop.

She then curled up next to him on the sofa, resting her head on his
shoulder.

"That was fantastic baby.  I can't believe you never sucked cock before."

Erica smiled, "Only in my fantasies."

He laughed and then kissed her deeply.  "Do you want me to recipricate?"

"Do you want to?"

"I don't know, I've never thought about it."

Erica kissed him.  "Don't worry honey, I'm the bottom and the cock sucker
in our relationship.  If you've never fantasized about it after watching
your tranny videos, it's not your thing."

"You're the bottom are you?". He squeezed her buttocks.

She gently stroked his cock, which was now recovering its firmness.  "Yes,"
she whispered seductively into his ear.

They kissed and caressed one another.  Erica began jerking David off, and
he was starting to get hard again already.  David was patting Erica's ass,
and began to finger his asshole.  Erica gasped when the first finger was
inserted, but began to settle in as the finger rubbed against his inside.

She began moaning when the second finger began stretching her asshole.
When he removed his fingers, Erica felt really open.

David stood up and extended his hand to Erica.  They walked hand-in-hand to
the bedroom.  To some degree, the steady hand guiding her was a necessary
reassurance.  Entering the bedroom, and all this meant, was advancing this
relationship and Erica's new identity to a new level from which there was
no return.

David guided Erica to kneel down on the edge of the bed. He then removed
the decorative panties.  Erica knelt in silence, ass in the air, and her
small penis fully erect, such as it was.  She wanted to say something, or
ask if he had done this before, but the time for conversation or second
thoughts had passed.

He squeezed a cool gel over the crack of her ass, and then rubbed it over
and then in her asshole.  She gasped at the sudden intrusion.  The gel
warmed up, and the lubrication now allowed his fingers to slide in easily.
A third and forth finger were subsequently inserted, which really stretched
her anus wide.

The fingers were removed and Erica waited nervously as David positioned
himself behind her.  The tip of his penis nudged her ass, eliciting a gasp
from Eric.  It was the last moment it would be him, not her.  With one
hand, David firmly grasped her hip, and guided his penis into her with the
other hand.  He pushed into her with a slow and steady thrust.

Erica moaned with a mixture of pain and pleasure.

Once his cock was fully buried inside her tight ass, he began a rhythmic
fucking.  Erica could only grunt and moan as her insides were thoroughly
stretched.  His hard thrusts nearly knocked the air out of her.

David grabbed hold of her hips and fucked her with wild abandon.  The
tightness of Erica's ass, and the way it gripped his cock was exquisite.
Erica's moaning was turning him on more and more.  It was so much better
than he had fantasized, and the sensation of penetration was much better
than a woman's pussy.

He was losing energy from the rapid thrusting and began to breath heavily.
His cock was tingling with pleasure, and he could feel his orgasm coming.
With one last thrust, he buried himself deep inside her and shot his load.
Erica arched her back to receive him.

Both exhausted, he pulled out and they collapsed onto the bed.  They
embraced and kissed one another.  They murmured endearments, kissed and
stroked one another, as they bathed in the afterglow.

They drifted off to sleep in one another's arms.


Epilogue

When Erica returned home the next day, she remained in femme attire.  Her
sister was eager to hear all the news.  The two of them joked and gossiped
amongst themselves as sisters.  They even went clothes shopping to build
Erica's new wardrobe.  Erica was nervous at first being out in the day, but
relaxed as apparently everyone accepted her as a girl.

They were sitting down for dinner at home when their mother came home.
Erica had a sudden lump in her throat as she had not thought about her
mom's reaction.

Claire welcomed her at the door, visibly nervous herself.

Sensing that something was wrong, Ms. Simon asked, "What's wrong?"

Claire took her mother's hand and led her to the dining room.  Erica waited
nervously, resisting the temptation to run.

"Mom, please don't be angry." Claire took a deep breath.  "This is Eric."

Ms. Simon was stunned.  All she could muster in response was "Oh my."

The three of them were motionless, unsure how to react.  Then Ms. Simon
started to giggle, and then laugh out loud.  It was infectious.  Claire
started to laugh, and then Erica joined in.  It was a laugh of release.  A
release from the tension and the absurdity of life.

"I always suspected... well something," Ms. Simon said between fits of
laughter.  "And I knew about you stealing your sister's old clothing.  I
just never imagined you would look so pretty as a girl."

Erica hugged her mother and from then on, it was only Erica around the
house.  Her father left the family years ago.  To some degree, Ms. Simon
was relieved that Eric no longer reminded her of his/her lousy father.

It was not long after that David was welcomed to the house for dinner, and
was accepted in the family.

The following semester, Erica registered for the university courses, and no
one noticed or cared about the transition.  There was no going back.  And
Erica, with her handsome boyfriend, wouldn't have it any other way.

THE END