Date: Sun, 31 May 2009 23:27:16 -0400
From: indybicd@aol.com
Subject: Adventures with Creative Endeavors 2

Adventures with Creative Endeavors
By
Stephanie (indybicd@aol.com)

Part 2: "Stephanie''s First Date"

      It took only about half a week for Susan to line up Stephanie's first
date as a full member of Creative Endeavors, Inc.  It was to be on the
upcoming Friday evening after work.  She was told to report to Creative
Endeavors, Inc. about an hour before the date to prepare for the date and
to be "briefed" on the arrangements.  Stephanie could hardly wait for
Friday.  She picked out one of her most dazzling outfits she could find as
soon as she heard about her date on Friday so that she could make sure it
was all nice and clean and ready to go for her first "date".

      Friday at work seemed to drag on forever for Stephanie and she found
it hard to concentrate on much of anything else other than her upcoming
date that evening.  Stephanie was definitely excited about her date but
also a bit anxious as well.  She thought that she'd probably be o.k. but
still wasn't''t sure about what kind of people she would be spending time
with and how safe they would be.  Susan seemed like she wouldn't''t
knowingly hook her up with somebody who she thought might harm her but, as
Stephanie knew from experience, it can still be difficult to know who to
trust.  Caution in their business was even more important since it needed
to be kept discreet because none of them wanted to have to get the cops
involved and poking around the business.  Still, her curiosity was getting
the best of her and she figured to himself that she'd be willing to at
least try this out.  She knew she certainly didn't''t have to keep doing it
if she didn't''t like it.

      After what seemed like an eternity, her workday finally drew to a
close and she dashed out the door to her car and to her fateful rendezvous
with "destiny" at Creative Endeavors, Inc.  When she arrived back at the
office of Creative Endeavor, Inc. and walked through the front door, she
saw Susan, again manning the phones and could glimpse Hannah in her office
also chatting on her phone.

      ""Hi darling,"" exclaimed Susan.  She seemed genuinely happy to see
her again.  Stephanie figured she knew why.

      ""Oh, hi Susan,"" she replied pleasantly.  ""How are you doing this
afternoon?""

      ""Oh, I'm doing fine, darling.  Hannah's in her office making all of
the final arrangements.  Do you need any help getting ready?""

      ""I don''t think so but 'I'll let you know if I do, thanks,"" replied
Stephanie.

      Susan winked at Stephanie.
      Stephanie entered the bathroom and got on her selected "hot" outfit
and began touching up her makeup and lipstick and using the toilet.  As she
finished going to the bathroom and getting ready to wash her hands, she
noticed an envelope on the sink counter with her name marked on it.
Curious, she opened it up and discovered a simple greeting card from Susan
thanking her for joining up with Creative Endeavors, Inc. as well as for
her "high achievement" on her "test" a week earlier.  Stephanie also
noticed a few condoms and a couple packets of lube- which she imagined was
""standard issue"" in case she needed them later tonight on her date.
Stephanie tucked the card and "accessories" into her purse and left the
bathroom.

      When she emerged from the changing room, Stephanie noticed Hannah
leaning on Susan's desk chatting with her.  She also noticed a man who
looked to be in his mid-30's and in a really nice business suit seated
comfortably on the couch glancing at a magazine.  As soon as Stephanie
entered the room everybody suddenly turned and stared at her.  The room
seemed a hundred degrees warmer all of the sudden to Stephanie.  The
gentleman on the couch put down the magazine and started to stand up.
Stephanie felt herself turned red.  She wasn't't sure why but she had
always got embarrassed by lots of people staring at her.

      ""Ah, here she is,"" Hannah exclaimed, looking at the man on the
couch and motioning towards Stephanie.  ""The lady of the evening,"" she
announced.

	The man stood up and moved forward to take Stephanie's hand.
Stephanie reflexively extended her right hand.  He bent over and gently
kissed it.  He seems like a real gentleman, thought Stephanie.

      ""Greetings,"" he politely stated, with what sounded like a slight
British accent.

      ""Hello,"" replied Stephanie meekly.

      ""My name is Richard.""

      ""My name is Stephanie,"" she stammered nervously in reply.

      ""Ms. Sullivan and Ms. Anderson have told me that you're new here and
that this will be your first... assignment.""

      ""Yes, sir,"" she replied."  She was nervous beyond belief.  This was
going her first real date as an escort and she didn't't know how to act.

      ""There''s no need to be nervous,"" stated Richard in a reassuring
manner.  ""I just want to spend a little time with somebody this evening
and from what Ms. Sullivan and Ms. Anderson has told me, you seemed like
you would make for good company.  How does a nice dinner out seem?""

      ""That sounds nice,"" Stephanie agreed.  She glanced over at Hannah
and Susan who were both observing her interactions with Richard.  They both
looked back of her and Susan shot her a "thumbs up".  Stephanie took that
to mean she must be doing okay so far with Richard.

      ""Good.  Then why don't we head on out?  The night is not getting any
younger,"" he playfully stated with a grin on his face.

      ""Oh yes, of course,"" Stephanie agreed.  She worried that she was
looking like a blithering idiot so far.  She wondered if she was going to
be able to manage this job o.k. since she could barely even speak to her
"date."  It was her job to be out in front of people all day every day and
yet know she had been reduced to stammering her way through a simple
introduction.  She also wondered what Hannah and Susan must be thinking.

      ""May I take your hand," he politely asked.

      ""Yes, of course"" replied Stephanie, once again offering her hand to
him.  She shot a parting glance at Susan and Hannah who were continuing to
watch their interactions with encouraging looks on their faces.

      ""Have a good time,"" said Hannah encouragingly, with a smile on her
face.

      ""Thanks," replied Stephanie, feeling a little more relaxed but still
unsure about how this was all going to turn out.  ""Don''t wait up for
us,"" she said jokingly.

      Stephanie turned her head, adopted her most feminine stride and
walked out of the door of the office with Richard and her holding hands.
Richard maintained Stephanie's initial impression of him being a
"gentleman" throughout their entire "date".  He held doors open for her,
addressed her calmly and politely, listened to her attentively, and simply
treated her "like a lady" and the more he did it the more like a "lady"
Stephanie began to feel. Stephanie eventually began to relax and open up a
little about herself, her "job", interests, life, etc.  She also was
treated to a marvelous dinner of the finest steak and wine she had ever
consumed and was having such a wonderful time that the concept of time
simply seemed to vanish.  While taking a quick restroom break, she glanced
at her wristwatch which was showing 10:00 PM.  Either because of the wine
or because of her own feelings about Richard, she realized that was
starting to feel quite horny and while sitting on the toilet after peeing,
she began fantasizing about giving herself to Richard sexually.  She
grabbed for her cock and started stroking it while becoming lost in
fantasies about being passionately fucked by Richard.  After a couple of
minutes of jerking off, she realized that she didn't't just want to jack
herself off and then go home "all spent," particularly if Richard wanted to
have sex with her after dinner.  She decided that she'd "save" herself
until at least she knew what would happen between her and Richard.  If
worst came to worst, she'd just take herself back home and pull out her
toys and take care of her needs.  She stopped stroking herself, pulled her
clothes back on, and casually returned to the table, although all she could
do was fantasize about Richard fucking her and didn't't hear a single thing
he said for the rest of dinner.

      She was thrilled to discover that Richard actually wanted to invite
her back to his place for a "nightcap."  Stephanie didn't't exactly know
what a "nightcap" meant for sure but didn't't really care.  All that
mattered to her was that she knew that it involved going back to his place.
Stephanie became so excited that she felt her heart skip several beats and
her cock stiffen- which made her ache even worse for Richard after having
already fantasized about being with him and stroking her cock a few minutes
earlier.

      Richard drove them both to an elegant two-story home in a high-end
residential neighborhood.  Stephanie's cock was straining to get out of her
panties and her balls were aching.  She couldn't't wait to get her hands on
Richard.  After parking the car and unlocking the front door, he held the
door open for her while she clambered out.  They proceeded to go on into
the house together.  Almost as soon as they had passed through the front
door and closed it, Richard pulled Stephanie towards her and planted the
hardest, longest, and deepest kiss that she had ever received in her entire
life- even slightly more fantastic than the one that Susan had given her a
week earlier.  Stephanie simply melted into his arms.  As they embraced,
Stephanie could feel their cocks pressing up together through their
clothes.  She reached down and started rubbing his cock up with her hand.
Ooooh!  It felt HUGE!  Her cock was so stimulated by now that it threatened
to soak her panties with her man cream before she and Richard had even DONE
anything more than passionately kiss.

      Stephanie gently disentangled herself from their passionate embrace-
albeit with tremendous effort.  She didn't want things to be over too soon.
""I guess somebody wants some extra attention this evening,"" she observed
suggestively.

      ""Yes indeed.""  Richard was panting.  ""I was hoping that you would
offer it.  Ms. Sullivan and her receptionist both thought that you''d be
interested.""

      ""Well, they are certainly correct.""  Stephanie fondly reminisced
about her and Susan''s mutual cock-sucking extravaganza they had enjoyed
when she was first hired by Creative Endeavor's, Inc. a week ago.  ""I was
wondering something, however..."..."  She paused a moment so as to make
Richard beg for her to reply about her request.

      ""Yes, my dear,"" he asked sweetly, gently grabbing her hand and
planting a small kiss on it and smiling.

	""For a long time I have fantasized of wanting to be taken like a
woman and I can think of nobody better than somebody like you to introduce
me to such pleasure.""  Stephanie paused for a moment to let her request
sink in, wondering if Richard would be willing to oblige.

	Richard seemed to know exactly what she was asking for and the
expression on his face suggested that Stephanie would definitely be getting
her wish tonight.  ""It honors me that you have chosen me to do the honors
of claiming your virginity.""

	Stephanie was ecstatic.  ""It would be an honor for my virginity to
be taken by such a fine gentleman.""  Richard''s formal manner of speaking
appeared to be rubbing off on her a bit.  Stephanie could not wait until
they were rubbing each other...in a slightly different way.

       Stephanie and Richard proceeded upstairs to a lavish bedroom
containing a queen-size bed.  Both Stephanie and Richard began undressing
each other until they were both stark naked with each other.  Richard had a
nice-sized cut cock and wonderful ass.  Stephanie's cock was nice and stiff
as well, clearly anticipating the pleasure to come.  They both lay down in
bed on their sides and moved close to each other and embraced each other,
kissing each other gently, their bodies and cocks occasionally rubbing
together.  Richard briefly suckled at Stephanie's firm breasts.  She let
out quiet sighs of pleasure in response to his attention to her boobs.  Of
all of the alterations to her body as a result of her transition,
developing boobs was simply the best part.  After a couple of minutes,
Stephanie reached down to Richard''s cock and began stroking it just as she
had done to her own earlier.  Richard moaned softly and they continued
tonguing each other passionately.  Finally, being unable to keep herself
from letting go, she pulled herself up from the bed and fumbled through her
purse for the condoms and lube she had been given earlier.  She opened the
wrapper and motioned for Richard to roll over on his back, which he
obediently did.  She proceeded to unroll the condom onto his cock.  No
sooner had she gotten the condom on him, she bent over him on the bed and
began hungrily sucking away at his cock, which sent Richard into a series
of low moans and grunts.  Stephanie was careful, however, to stop after
only a couple of minutes of intense cock-sucking because she didn't't want
him to cum like THIS.  She still needed his cock hard in order for him to
properly "deflower" her.

	Richard, noticing that Stephanie had stopped sucking on him, opened
his eyes and gazed at Stephanie lovingly.  ""That was wonderful dear,"" he
exclaimed in the same kind of quiet and thoughtful manner in which he had
addressed her all evening.

	""You''re very welcome,"" she replied.  She then lied down on bed
next to him and stared at him.  ""I'm ready to lose my virginity to you
now,"" announced Stephanie as she carefully opened the packet of lube and,
lifting her legs up to her chest, dabbed some on her ass with her finger.
She then passed it to Richard, who, by now, had gotten up on his knees
facing her.  He rubbed some lube over his sheathed cock and started slowly
advancing towards Stephanie.

	 ""It would be my honor, dear,"" Richard stated with a reassuring
smile.

	""Just take it slow for a couple of minutes,"" requested Stephanie.
Although she had used dildos and other butt toys on herself she had never
before taken a full-sized cock in her asspussy and wanted to make sure it
would be a pleasurable experience for her.  She wanted to remember and
savor this moment forever.  She was feeling like a woman awaiting the first
penetration of her pussy by a boy's cock and in many ways her experience
would probably not be too dissimilar.

	""As you wish,"" replied Richard as he gently lifted Stephanie''s
legs onto his broad shoulders and began lining up his cock with
Stephanie''s asspussy.  Once everything was aligned, he slowly and
cautiously started entering her ass.  Stephanie concentrated hard for a
couple of minutes on making sure her ass muscles relaxed enough to allow
Richard's wonderfully massive cock to fully penetrate her.  Although she
got a lot of pleasure out of dildos, simply nothing could compare to this
new sensation of having a REAL cock in her asspussy, a nice-sized one at
that.  After what seemed like an eternity, Richard''s cock was finally
stuffed all the way inside of her and Stephanie could feel his balls
resting just outside on her butt crack.  Stephanie was amazed at just how
awesome it felt and took a moment to simply relax and savor the fullness of
his manhood.

	""Well, are you ready for me to start thrusting,"" Richard politely
asked.

      Stephanie was pleased by how Richard's gentlemanly manner seemed to
extend even into the bedroom.  He was a real catch, she thought.  ""Please,
Richard, take me"," Stephanie requested breathlessly.  Richard started
moving his cock in and out of Stephanie''s asspussy- slowly at first and
then increasingly faster as the minutes wore on.  Stephanie''s cock was
starting to get hard in response to the intense prostate stimulation she
was getting from Richard''s cock rubbing up against it inside of her and
she began gently rocking her hips to match the rhythm of Richard''s
thrusting.  Stephanie closed her eyes and began to moan softly.  Nothing
could have ever made her feel like more a woman than this, she thought.
Richard gradually increased his speed and tempo.  As he got faster the
prostate stimulation got even more intense and the more she wanted him to
go deeper and deeper.  Richard was eventually moving his cock in and out so
effortlessly that she forgot for a moment that she had an asspussy and not
a REAL pussy.

      ""Oh yes!!!  Fuck me, Richard!!!!  Fuck me!!!!!"  Stephanie couldn't
stop from shouting out loud.  Richard continued to increase his thrusting
speed even more in response to Stephanie''s pleas.  Stephanie could hear
him start to moan and pant while thrusting his cock in and out of her.
Although she had initially decided that she wanted to just lie on her back
and take Richard's cock, she suddenly decided that she didn't really want
to cum in this position and that she actually wanted to ride Richard''s
cock the rest of the way to orgasm instead.

      ""Richard, Dear?"" She suddenly asked breathlessly, panting,
attempting to put a momentary pause to their passionate lovemaking- with
considerable personal difficulty.

      Richard brought his thrusting to a complete halt and looked at her
lovingly.  ""What is it, my love,"" he replied, also struggling to catch
his breath.  His rock-solid cock remained buried in Stephanie's asspussy
while he patiently waited for her to speak.

      ""I really love your thrusting, darling, and you're doing a
magnificent job taking me like a woman but I've decided that I actually
want to ride that beautiful cock of yours the rest of the way,"" she
replied lustfully.

      Richard seemed pleased with the request and gently withdrew his cock
out of her asspussy and lay down on the bed on his back.  ""Very well, my
dear.  You may proceed"."

      Stephanie started to position herself to straddle Richard.  She was
eager to plant his cock deep in her asspussy again until she came but then
realized that she wasn't't wearing a condom and the agency probably
wouldn''t approve of her spraying her man cream all over Richard's belly,
which is probably what would happen if she didn''t cover up while riding
him.  She reached over to the nightstand and grabbed herself a condom and
proceeded to aggressively impale her asspussy on his still rock-hard cock.
He gasped out of surprise at Stephanie''s aggressiveness but did not resist
her in the slightest.  Stephanie''s asspussy was so relaxed by now that
Richard''s cock just slid right on in effortlessly.  Stephanie had always
fantasized about riding a cock like how women had rode her in the bedroom
before but she had never had an opportunity to actually try it
out... ...until now.  With Richard''s cock planted firmly up her asspussy,
Stephanie stroked her cock until it was hard enough and then sheathed her
cock with a condom.  Stephanie then began effortlessly bouncing up and down
on Richard's cock and stroking her cock at the same time.  Richard's eyes
were closed and Stephanie could hear him moaning with pleasure at her
actions.  With his cock firmly planted in her asspussy, Stephanie leaned
forward to put her hands around the back of Richard's neck and began
kissing him.  Richard eagerly welcomed the embrace.  Stephanie then leaned
back and resumed her bouncing on Richard''s cock.  Soon, she and Richard
had found their "rhythm" together and they both became lost in a state of
exquisite pleasure.  The angle that she had managed to maneuver herself
into was allowing nearly every jab and thrust of Richard''s huge cock to
hit her prostate.

	After a few more minutes of Stephanie''s bouncing, Richard''s body
suddenly jerked and he shouted out in pleasure and Stephanie felt him lift
his waist up making his cock give her insides a deep jab as she brought her
asspussy down to meet it head on.  Stephanie couldn't control herself
anymore either and responded to Richard's orgasm by aggressively impaling
herself on his cock one last time before violently spraying her own man
cream into her condom in concert with her own shouts and cries of orgasmic
ecstasy.  For their added pleasure, she ground her ass down on Richard's
cock as far it could go as she continued in the throes of her orgasm.
Finally, sensing Richard''s cock starting to deflate a bit, she reached her
hand around her back towards her ass, lifted her ass up slightly, grabbed
his cock around the base of the condom, and gently eased herself off of
him.  She then collapsed onto her back on the bed.
 	Stephanie was relieved to see that Richard''s condom was still
safely in place on him and that no bodily fluids had ended up on or near
her asspussy.  Stephanie imagined that it would be interesting to feel what
it would be like for somebody to ejaculate into her ass without a condom
and feel their seed all over her insides but she knew what kind of awful
chances she would be taking of getting an STD that way.  Stephanie observed
Richard still lying on his back panting and moaning with his eyes closed
and body limp.  It took a few minutes for the both of them to even start to
recover from their intense and passionate lovemaking session.  Finally,
Stephanie tentatively sat up and stretched her arms.  Richard was still
lying on his back with his eyes closed and a grin on his face.  Needing to
go to the bathroom, Stephanie got out of bed and walked (stumbled?) to the
bathroom.  She peeled off her used condom, wrapped it up, and tossed it in
the trash.

      As she sat on the toilet, she suddenly felt like the world had opened
up to her in way that was not unlike how her asspussy had eagerly opened up
to Richard's cock this evening.  She could tell that her life would never
be the same again.  Her asspussy would almost certainly remember tonight
for the rest of her life and she knew that she would continue to savor her
experience with Richard.  She also realized that her first "date" would be
soon coming to an end and that she would be returning back to her "normal"
life, at least until Creative Endeavors, Inc. arranged her next "date" for
her, but she knew that this was only the first in what would surely be many
wonderful dates- some of which she may again enjoy with Richard, who had
earned a special place in her life by being the "first" person to take her
"anal virginity" in a way that lifeless dildos simply couldn't.  Stephanie
smiled warmly at herself in the mirror, put her cup down, and strode back
to the bedroom.  Richard was passed out on the bed breathing comfortably.
She decided to lie down on the bed and join him.  She curled up next to him
and gently rested her hand on his chest and her head on his shoulder.
Stephanie could feel him stir slightly as he moved his arm around her back.
She had never felt so warm and secure as she did right now. She knew then
for sure that she was going to LOVE going on more "dates" for Creative
Endeavors.