From Wendycd@hotmail.com Fri Jan 10 07:16:12 1997
Newsgroups: alt.sex.stories
Subject: First Date (crossdressing)
From: Wendycd@hotmail.com (Wendy)
Date: Fri, 10 Jan 97 12:16:12 GMT

Chapter one

Rodger stopped and looked at his naked image in the mirror on the dresser, as 
he looked he imagined what the image would be in a few hours.  Smiling he 
walked into the bathroom and sank into the tub which was already full of hot 
steaming water scented with musk oil.  He soaked for a long time, washing 
carefully with a scented soap and ensuring that his skin and the hair on his 
body was soft.  Finally he sat on the edge of the tub and began to shave the 
hair from his groin, carefully he guided the razor around his balls and cock 
then he shaved them too.  Running his hands over the smoothness he smiled and 
then reached for the Nair hair remover. Standing, he slowly spread the remover 
over the rest of his body making sure that he covered the hairier regions 
fully.  After a few minutes he turned on the shower and began to wash the 
solution from his skin. As it washed off it left his skin smooth and best of 
all, hairless! Then it was time to shave his face, he bent to the task trying 
to ensure it was the best, smoothest shave he had ever done.  Satisfied with 
the work he went back to the bedroom,  looking in the mirror he was stunned 
and pleased with the new smooth look, the way it emphasized his nipples and 
cock.  Sitting in front of the mirror he began to put on make-up, trying  to 
remember how his late wife had done it.  As he put on the eyelashes and 
eyeliner his face seemed to become softer and more feminine. He opened a 
bottle of wine colored nailpolish and applied it to his nails, hands first 
then his toes making sure it was just so.   At last it was time for the 
lipstick, slowly, carefully he reddened his lips then outlined them.  Then he 
reached for the wig he had purchased earlier in the day and placed it on his 
head, the look stunned him. Where had once been Rodger now there was Wendy 
looking back at him, smiling , Wendy took in the transformation.  And now it 
was time to dress,  she began with sheer white stockings, slowly pulling them 
up each leg ensuring there were no runs and that the seam was straight.  The 
garterbelt was next followed by white satin panties, as she pulled the panties 
up she tucked her cock back against her crack so she was smooth in front.  A 
matching  satin bra was then put in place and filled with some beige pantyhose 
to provide the required  look. Now looking in the mirror it was hard to find 
Rodger at all, in his place was a reasonably pretty Wendy  looking very 
attractive in the lovely lingerie.  She sat on the edge of the bed and put on 
the white pumps with six inch heel and did up the ankle straps. She stood,  
unsteady for just a second the walked to the closet, she selected a short slip 
and slid it on relishing the feel of the material as it swished over her 
stockings and panties.  The a  fairly sheer white blouse and short blue skirt 
completed the look.  Wandering back to the mirror she looked at the image 
facing her.  There looking back was Wendy looking very sexy indeed, the short 
skirt just covered the tops of her stockings and her bra was just hinted at 
under the blouse, satisfied she turned away and went downstairs.

Looking at the clock she realized that Jim would soon be arriving, she 
wondered what he would say when he first saw her.  Needing a drink now Wendy 
went to the bar and made a pitcher of martinis then poured one for herself.  
As she sat on the sofa sipping her drink he mind raced through some of the 
possibilities that she might be faced with when Jim arrived, then it was too 
late, the doorbell rang.

She walked to the door, then  smoothed her dress, took a deep breath and 
opened the door " hello Jim, come on in".  Jim stood there in stunned silence, 
he had been expecting to be met by Rodger who was going out to the tavern with 
him and now here was, was..  "Please come in Jim, let me explain this all to 
you".  Jim finally walked in and Wendy shut the door behind him then lead him 
to the couch.  "Here, have a seat and I'll pour you a drink, you may need it", 
Wendy went to the bar and fixed him a martini and brought it over.   As Jim 
watched her walk to the bar he realized what a nice looking girl, nice legs 
and tight butt, then he snapped out of it, this was Rodger!?   Wendy handed 
him his drink and then sat beside him with her own, "well Jim I'm sure you are 
wondering just what the hell is going on right?".  For a second Jim could only 
nod, then, "what the hell has happened Rodger, have you flipped out?"  Wendy 
smiled as she looked at him, took a sip of her drink, "well, this isn't really 
all new, I've been a secret crossdresser for years".  "But now since the loss 
of my wife I've decided that I want to be able to dress and look the way I 
want to when I want too".  Jim sat for a moment taking it all in, he knew that 
Rodger had been moody since his wife had passed away but this was almost too 
much.  " Rodger, are you going to be this way all the time, are you going to.. 
you know have an operation?" 


 Wendy smiled "no and no Jim, I'm going to dress as I normally do for work and 
dealing with most of the people I know, but when I am home and on my own I 
will be Wendy, please call me that when I'm dressed".  " I felt that you and I 
have been friends for a long time and I needed someone to share my secret 
with, do you think you can find it in your heart to accept me as I am?"  Jim 
sat sipping his drink and thought about the times he and Rodger has shared, 
the fishing trips, the parties, work and just being friends. Slowly it dawned 
on him that if this had been going on all this time, Rodger crossdressing, 
then it was still in  a way, the same Rodger he had always known.  "Well.. 
Wendy, this is going to take some getting used to but I am after all your 
friend so..."  He smiled and held out his hand "it's good to know you Wendy!"  
She took his hand and squeezed it gently so relieved that her friend had come 
through for her "thank-you so much Jim, you don't know what this means to me." 
 Wendy stood up "well, do you still want to go out for a few drinks?"  Jim 
looked at her "like that?"  Looking at him she grinned "yes, just like this, I 
need to see if I can get away with it." "Take me somewhere where the lights 
are a bit low and we will have a couple then come back here for a chat."  Jim 
stood "I suppose we could, you do look good" he blushed a bit "I mean that you 
look nice that..."  Wendy laughed "it's OK Jim. I felt your eyes on me before, 
don't be shy, if I didn't want to be looked at I wouldn't have worn this, and 
thanks for the compliment".  As they left the apartment and walked down the 
hall Jim couldn't help but notice how Wendy walked, it was if she had been a 
woman forever, he had to keep shaking his head to keep in mind that under it 
all was Rodger. 

As they left the building Wendy put her arm in Jim's , he started for a second 
and looked at her " well a gentleman should be there for a lady to lean on 
shouldn't they?"   He grinned and opened the door for her, as she got in he 
hesitated for just a moment enjoying the sight of her long legs and the 
glimpse of stocking top.  He got in and started the car "well let's go down to 
the Figgie's Lounge, they have some nice surroundings and it's quiet".  Wendy 
smiled, "good by me Jim', she had been hoping that he would take her somewhere 
decent, she had been half afraid that he would take her somewhere seedy out of 
 embarrassment.  When they pulled in the lot Jim jumped out and went around to 
open  the door, once again enjoying her legs as she got out, it was odd, even 
though he knew that it was Rodger he still felt a bit aroused at the look of 
her. Again she took his arm as they walked and when they approached she stood 
just behind him while he asked for a booth.  When they walked down to the 
booth she slid in and sat down, Jim went to sit across from her , she patted 
the space beside her "why don't you sit here, it will look more natural, after 
all when you bring a pretty girl out you sit with her don't you?"   Jim 
hesitated for just a second then slid into the booth with her, as their hips 
and thighs met he felt a jolt of electricity run through him, almost like the 
first time he had been out with a girl.  Jim ordered drinks and looked around, 
several of the men in the bar had followed Wendy's  passage through the bar 
with approval, he had seen their eyes wander over her body lingering on her 
lovely legs, he felt a bit of pride in the fact that this pretty girl was here 
with him.  Then he realized what he was thinking and tried to put it back in 
prospective, she was a he, his best friend and definitely a he, why then did 
she seem to arouse him?  While all these thoughts were drifting through his 
mind he felt a touch on his leg and looked down to see he hand on his thigh, 
he looked at her "Jim I know that a lot must be going through your thoughts 
now but just remember I'm still me, I'm just sharing more of me with you than 
before" with that she gave his leg a squeeze.  When she did this Jim felt 
himself becoming more aroused, the scent of her, the look, the touch of her 
was more than his senses could cope with and he felt his cock begin to harden. 
 "Wendy this will take a bit of getting used too, I'm not sure how to act or 
react with you, my eyes tell me woman but my heart say's Rodger."  "Jim, I'm 
both, right now I'm Wendy and I need to be treated like a woman, I want to be 
looked at and touched and loved and..." she took a deep breath "and made love 
to".   She slid closer to him and let her hand slide up to rest on his cock 
feeling the hardness there " I see that I have had some effect on you haven't 
I?"  Jim could only blush and stammer while he tried to find where it was all 
leading "I'm, well, I'm not sure what you mean, what you want, what I want..." 
 Wendy gave him a quick rub "let's go back to my apartment so we can chat for 
a bit, OK?"  Jim paused and looked at her, then he nodded "yes, after all I 
can't sit here like this too long, folks will notice the spot on my pants" 
Smiling, he stood and helped her out of the booth, then he took her arm and 
led he to the car, when she got in, she let her skirt ride very high  looked 
up at him and smiled "better get in quick before that bulge in your pants gets 
noticed"

  Jim flushed and jumped in the car, while they drove they spoke little, he 
noticed she had not pulled her skirt down and he could see the tops of her 
stockings and how smooth her legs were, again he found himself getting harder. 
 She stole a glance at him as he drove and was pleased to see the effect she 
was having on him, she squirmed a bit and her skirt rode a bit higher yet then 
she reached over and put her hand on his bulge while they drove.  The feel of 
her hand was driving Jim crazy, he wasn't sure that he was going to be able to 
make it to her apartment without soiling his pants, worse he wasn't sure what 
he was going to do when they got there.  They reached the building and fairly 
ran to the apartment, he took the key from her and opened the door, when he 
closed it  behind them she spun into his arms and kissed him deeply.  Much as 
he was unsure and off balance he kissed her back and felt her tongue between 
his lips and her groin pushing against his, he slid his hand down to he ass 
and pulled her close.  Her hand slid between them and grabbed his hardening 
bulge "Wendy be careful, I'm on a hair trigger!" Wendy smiled "well we can't 
have that" she went to her knees and undid his pants and pulled them down, 
then she slid his underwear over his hard cock allowing his uncut cock free.  
She looked up smiled and then touched the tip with her tongue tasting the drop 
of pre-cum there, then ever so slowly she slid her mouth over his cock.  
Standing there watching his cock disappearing into her mouth Jim shuddered, he 
never felt attracted to men but this wasn't a man, was it? All he knew is it 
felt wonderful as she held his balls and pulled him into her, he was already 
at a knife edge and it wouldn't be long before he came "Oh Lord! Wendy that's 
so good, but I'm going to cum soon".  She slid him out of her mouth  grinned 
up at him "so cum then, I want you to last longer the next time so we may as 
well clear this up!" she slide her mouth all the way down to his balls and 
began to suck him harder, she put her hands on his ass and pulled him deep 
into her with each stroke.  He felt the cum rising in his balls as her expert 
mouth coaxed his load from him,  he grabbed her head and started to thrust 
deeply into her mouth as his sperm welled from his cock "yes! Yes! ohhh that's 
it! Ugghh!"   As she felt Jim's balls tighten Wendy sucked for all she was 
worth and was rewarded with jet after jet of hot juice spraying into her 
mouth, she gulped trying to swallow it all and kept on sucking him as hard as 
she could, fucking the last drops of cum from him with her mouth.  Jim gasped 
from the intensity of it,  he had never been blown like this before and she 
was still going, much as he couldn't believe it his cock was staying hard 
'whoa girl! Let's go over to the couch and sit before I fall!"  Wendy stood 
and kissed him letting her cum coated tongue slide into his mouth " no, let's 
go to the bedroom" she took his hand and led him down the hall.  She pushed 
him back onto the bed "now you just sit there for a moment while I get a bit 
more comfortable" she undid her blouse and then her skirt, turning her back to 
him she slid her slip off letting his eyes wander over her ass.  She looked in 
the mirror and grinned at him as his eyes devoured her, she wanted his hands 
on her so she reached back and undid her bra and let it fall to the floor.  
She turned 'I'm a bit small in the breast department , I hope you don't mind" 
with that she reached up and pinched her hard nipples.  Jim could only look  
at her, taking in the smooth skin, the stockings, she still didn't look like 
Rodger just a girl with small tits, he stood and took her into his arms and 
kissed her.  "You look just fine to me", his lips wandered down her neck and 
shoulder tracing a line toward her nipple, his tongue circled the hard little 
nub then he sucked it into his mouth and nibbled it, his hand slid down her 
back then over the smooth curve of her ass.  Then he kneeled before her, "I 
need to know, I need to see" he hooked his fingers in her panties and slowly 
slid them over her  stocking clad thighs,  her smooth cock slowly rose from 
between her legs.  She watched him unsure of what his reaction would be to the 
loss of the illusion, there was no mistake it was a cock, she held her breath 
hoping that the magic would last.  He looked at her hardening cock unsure of 
how he felt, by now he was aroused more that he could ever recall almost 
without thinking he bent forward and took her into his mouth and gently 
sucked.  Wendy threw her head back and moaned, it was as if her cock were on 
fire in the furnace of his mouth, the relief of the moment and the joy washed 
over her letting her abandon herself to his ministrations.   He grabbed her 
ass and pulled her into his mouth as she had him, he was almost frantic now, 
nothing seemed to have any meaning, nothing except the need to taste her sperm 
on his tongue.  He plunged her in and out of his mouth burying her deep in his 
mouth with each stroke feeling her cock throb and her balls tighten as she 
began to cum.  "Oh yes!! Jim! Jim! Make it happen! Oh! Ohhhhh!!"  Wendy was at 
his mercy her cock was pumping out what seemed like endless jets of cum into 
his sucking , she could feel each blast as it moved up her shaft and into the 
waiting cauldron of his mouth.  Finally she was spent and fell back on the 
bed, he moved over her and kissed her letting drops of cum coat their lips and 
tongues as they gave themselves up to the moment.

As they lay there kissing each other and relishing the taste of cum between 
them Jim's throbbing cock pulsed against Wendy's  spent one.  "Hmmm  I know 
what we can do with that!" sliding down she slid her lips over his cock again 
and gently began to swirl her tongue over the tip.   He turned and moved into 
the classic 69 position and began to arouse her again.  They lay there for a 
bit sucking each other almost feeling like they were sucking their own cock, 
mouths moving in unison over each other.  Wendy pulled away for a moment "Jim, 
I want you to make love to me like a woman, put a finger into my man-pussy and 
loosen me up, I need to be filled with you".   Jim let his hand slide over 
Wendy's smooth ass until the tip of his finger was touching her puckered 
opening, he slowly worked it into the tight opening bit by bit wondering how 
he would ever get his cock in such a small hole.  He decided that it would 
need some lubrication so he traced down her balls with his tongue and then to 
her man-pussy,  he let his tongue replace his finger as he worked it into the 
musky hole fucking her with his tongue.  Wendy gasped as she felt him enter 
her and thrust back against his mouth spreading her legs as much as she could. 
  Jim worked at her hole feeling it become softer and looser, the musky smell 
of her was driving him wild and he wanted her more than ever,  he sat up and 
put her on her back  holding her ankles he spread her open  before him.  He 
leaned forward and placed the tip of his cock against her wet man-pussy and 
slowly began to push in watching as the tip pushed in then feeling the warm 
embrace of her hole as the knob went in.  Wendy couldn't believe the feeling, 
first a bit of pain while the head of Jim's cock went in then the wonderful 
feeling as it slid deep into her finally bumping into her prostrate.  " Oh 
yes! Jim please fuck me, I need to be fucked hard  use my pussy... please!!"  
Jim put her legs up over his shoulders and  let his cock sink into her as far 
as it would go, the tightness of her was almost more than he could bear and as 
he stroked in and out of her he could feel his balls tightening  "oh Lord, you 
are so tight, I can feel a load building in my balls" he ploughed into her 
hard "ugh!"  "Yes! Yes! That's the way Jim, pound me!"   She reached down and 
grabbed her ass and pulled the cheeks apart letting him go as deep as he could 
feeling the tip of  his cock bouncing off her prostrate, she could feel he own 
 cum rising as her prostrate was being  massaged "I'm going to cum!! Yes! Yes! 
Deeper! Deeper!  Yesssss!!!".  With that, a jet of cum sprayed from her cock  
all over her chest then her cock pulsed spurt after spurt with each plunge of 
Jim's cock in her.  As he pounded into her he saw her cum begin to spray and 
it triggered him " here it comes! Now! Now!  Ugggh!!!"  spurt after spurt 
sprayed into her as he plunged up to his balls.   "Yes! Yes! I can feel it oh 
yes!!" Wendy felt each spurt of Jim's hot juice as it washed over her 
prostrate, her cock still sprayed a small drop with each push of him until she 
was drained completely. He collapsed on her, cock still deeply buried in her 
and felt her cum and cock sandwiched between them hot and deliciously sticky, 
she wrapped her legs around him and held him close not wanting the moment to 
end.

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