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. More to cum