A Crossdresser's Love Story

What do you do when your long time friend shares a secret with you? If you're Jim, you respect his confidence and give him a good fucking!

All characters are at least18 years old. This little tale contains bisexual male oral and anal sex. If you have any hang-ups about this, move on! There's nothing here for you!

Rodger inspected his naked image in the full-length mirror on the closet door, imagining what the image would be in a few hours. Smiling, he walked into the bathroom and sank into the tub full of hot steaming water scented with musk oil.

He soaked for a long time, washing carefully with a scented soap bar and ensuring that his skin and body hair was soft. Finally, he sat on the tub's edge and shaved the hair from his groin, carefully guiding the razor around his balls and cock.

He smiled as he ran his hands over the smoothness and then reached for the hair remover. Standing, he slowly spread the remover over the rest of his body, making sure that he thoroughly covered the hairier regions.

After waiting a few minutes, he turned on the shower and washed the solution from his skin. It left his skin smooth and hairless as it washed off! Then he shaved his face ensuring 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. His deceased wife Ellen was right about the hormones. They softened the hard edges, giving him a softer silhouette and small breasts.

Sitting in front of the mirror, he began applying makeup, emulating how his late wife did it. As he put on the eyelashes and eyeliner, his face became softer and more feminine.

He opened a bottle of wine-colored nail polish and applied it to his nails, toes first, then his hands making sure it was just so.

At last, it was time for the lipstick. Slowly, carefully Rodger reddened his lips and then outlined them.

He chose a blond wig from his collection and placed it on his head. The overall change stunned him. Where Rodger once was, Wendy looked back at him, smiling.

Wendy began dressing, first pulling her sheer white stockings up each leg ensuring there were no runs and that the seam was straight. White satin panties next followed the garter belt. As she pulled the panties up, she tucked her cock back against her ass crack so she was smooth in front.

She added a matching satin bra. Before taking the hormones, she padded the bra with stockings to provide the required look. Now she had A cups. She and Ellen decided to let them grow to a small B. That would add a seductive bosom while allowing her to be Rodger. Most people assumed Rodger had gained a little weight. Now looking in the mirror, it was hard to find Rodger. A pretty Wendy seemed attractive in the lovely lingerie in his place.

She sat on the edge of the bed, put on the white CFM pumps with six-inch heels, and fastened the ankle straps. She stood unsteady for just a second, then walked to the closet and selected a short slip.

Wendy slid it on, relishing the feel of the material as it swished over her stockings and panties. She added a sheer white blouse and a mid-thigh short blue skirt to complete the look.

Wandering back to the mirror, she looked at her image. Looking back, was Wendy looking very sexy indeed. The short skirt just covered the tops of her stockings, and her bra was just a hint under the blouse. Satisfied, she turned away and went downstairs.

Looking at the clock, she realized that Jim would soon arrive. She wondered what he would say when he first saw her. Coming out to her 20-year friend was a considerable risk.

He could reject her outright, and she would lose his and his wife's friendship. He cherished them! They supported him through Ellen's long decline from cancer.

Wendy needed a drink to calm her nerves. She went to the bar, made a martinis pitcher, and poured herself one.

As she sat on the sofa sipping her drink, her mind was racing through some of the possibilities she might face when the doorbell rang, announcing Jim's arrival.

Wendy stood, smoothed her skirt, took a deep breath, and walked to the door. She grabbed the doorknob, took another deep breath, and opened the door.

"Hello Jim, come on in."

Jim stood in the doorway in stunned silence. He expected Rodger to open the door. Instead, this vision of loveliness had. He was unaware that Rodger had a girlfriend, especially one as hot as this vision!

"Jim, it's me, Rodger. Please come in. Let me explain this all to you."

Jim slowly walked in, and Wendy shut the door behind him and then led him to the couch.

"Here, have a seat, and I'll pour you a drink. You may need it".

Wendy went to the bar, fixed him a martini, and brought it over. Jim watched her walk to the bar, ogling her long 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 drink, demurely holding her knees together and turning them to the side as Ellen instructed him a lady does. Still, her skirt rode up, exposing her stocking tops.

"Jim, I'm sure you are wondering just what is going on, right?".

"What the hell has happened, Rodger? Have you flipped out? Sue and I knew you were having issues after Ellen died! But this!"

Wendy smiled as she looked at him and took a sip of her drink,

"This isn't new. I've been a secret crossdresser for years. Ellen knew and eventually approved and accepted me like this. But now, since she died, I've decided that I want to be able to dress and look the way I want to when I want to."

Jim sat in stunned silence for a moment, taking it all in. He knew that Rodger had been moody since his wife had passed away, but this was too much.

"Rodger, are you going to be this way all the time? Are you going to, you know, have an operation?"

"No and no, Jim. I'll dress as I normally do for work and when I deal with most 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 feel that you and I have been friends for a long time. 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 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, uh, Wendy! This is going to take some getting used to! But I am your friend, so..."

"it's good to know you, Wendy," Jim said, extending his hand.

She took his hand and squeezed it gently, relieved that her friend had come through for her

"Thank you so much, Jim. You don't know what this means to me."

Wendy wanted to cry but didn't want to ruin her makeup.

"Do you still want to go out for a few drinks?"

"Like that," Jim asked?"

"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. We will have a couple, then come back here."

"I suppose we could," Jim said, standing. You DO look good!"

Jim blushed a bit

"I mean," Jim stammered, hurrying to correct any mistakes, "that you look nice that..."

"It's OK, Jim," Wendy laughed, "I felt your eyes on me before. Don't be shy. If I didn't want you to look, I wouldn't have worn this, and thanks for the compliment".

Jim couldn't help but notice how Wendy walked as they left the apartment and walked down the driveway. Her hips swayed seductively as if she had been a woman forever. He had to keep shaking his head to keep in mind that under it all was Rodger.

Wendy put her arm in Jim's. He started for a second and looked at her

" A gentleman should be there for a lady to lean on, shouldn't he?"

Jim grinned and opened the door for her as she got in his SUV. Jim hesitated for just a moment, enjoying her long legs and the glimpse of her stocking top. He got in and started the car.

"Let's go to the Shelter Lounge. It's in a nice section of town, has some nice surroundings, and it's quiet.".

"Good by me, Jim," Wendy smiled.

She hoped he would take her somewhere decent. She was half afraid that he would take her somewhere seedy out of embarrassment.

When they pulled into the lot, Jim jumped out and went around to open the door. Once again, he enjoyed eyeing her legs when her skirt rode up as she got out. It was odd; even though he knew that it was Rodger, he still enjoyed looking at her.

Again, she took his arm as they walked across the parking lot to the lounge. Wendy demurely stood just behind him when they entered, and he asked for a booth.

She was aware of the stares of the men sitting at the bar as the server escorted them to a booth. She hoped they were staring because she was a sexy woman and not a man in drag. Early on, before his wife began helping him with clothes and makeup, he hadn't fit the illusion he was trying to create. In those dark days, she heard derisive snorts.

Wendy sat down and slid into the booth. When Jim sat 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 next to her. When their hips and thighs met, he felt a jolt of electricity run through him, 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 saw their eyes wander over her body, lingering on her lovely legs. He felt proud that this pretty girl was here with him. Then he realized what he was thinking and tried to put it back in perspective.

She was he, his best friend, and a he. Why then did she arouse him? While all these thoughts were drifting through his mind, Wendy lay her hand on his thigh.

"Jim, I know that a lot must be going through your thoughts now but remember, I'm still me. I'm just sharing more of me with you than I used to share."

"Rod...er...Wendy, when did all of this happen? Did Ellen know?"

"Yes, she knew! She had some issues when she first caught me in her panties and bra. However, over time she accepted it. She helped me with walking, selecting clothes, and applying makeup. Why on some vacations, we went as two women!"

When Wendy squeezed his leg, Jim's cock stiffened. Wendy's illusion of being a woman was enhanced by her scent, how she carried herself, and her looks. Her touch was more than his senses could cope with.

"Wendy, this will take a bit of getting used to. I'm not sure how to act or react to you. My eyes see a woman, a very attractive woman! But my mind says Rodger."

"Jim, I'm both," Wendy/Rodger said earnestly! 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."

"I don't know about all of that,' Jim said, taken aback. "I'm not gay!"

"And I know that! Since Ellen died, I needed to share my secret with someone, and I chose you! It needs to go no further than that!"

She slid closer to him and slid her hand to rest on his cock, feeling his hardness

"Despite what you say, I see that I have affected you, haven't I?"

Jim could only blush and stammer while he tried to figure out where it was all leading.

"Can I ask a question? Hell! Can I ask lots of questions?"

"Absolutely! But first, order us another drink."

Jim walked to the bar and ordered two drinks. The bartender sat them down and leaned in conspiratorially.

"You got a nice piece of ass there, bro!"

"Uh, thank you," Jim stammered.

He walked back to the booth and sat the drinks on the table.

"I saw the bartender whisper something to you. What did he say?"

"Uh, he said you looked like a nice piece of ass!"

Wendy tittered, caught the bartender's eye, and smiled. He winked at her.

"So how did you...!" Unable to say the words, he pointed at Wendy's chest.

"Hormones! Ellen suggested I take some to round off my figure. I'm a smallish guy at 5' 7" and 150 pounds, but a tall female. She thought natural breasts would make me voluptuous. I'm a big A or a small B in cup size. You like them?"

Wendy arched her back, poking her chest out.

"They're nice! You know what they say; anything more than a mouthful is wasted!"

Wendy leaned in, cuddling with Jim, her breasts against his bare arm.

"Stop that! Everyone is watching us!"

"Jim, they think you're going to get lucky with that hot bitch!'

"I'm, well, I'm not sure what you mean, what you want, what I want..."

Wendy gave his cock a quick rub.

"Let's go back to my apartment so that we can chat for a bit, OK?"

Jim paused and looked at her. 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 her 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 vehicle. They spoke little while they drove. Jim noticed she had not pulled her skirt down. He could see the tops of her stockings and how smooth her legs were. Again, he found himself getting harder.

Wendy stole a glance at him as he drove and was pleased to see her effect on him. She squirmed a bit and let her skirt ride a bit higher. She reached over and put her hand on his bulge while they drove.

The feel of her hand on his dick was driving Jim crazy. He wasn't sure that he would be able to make it to her apartment without soiling his pants. Worse, he wasn't sure what he would do when they got there.

"Jim."

"Yes?"

"Can I give you roadhead? I've always wanted to do that! Ellen would sometimes wear a strap on when she drove, and I would suck that! But I have never given a real cock roadhead."

"Look! You're my friend! I'm having trouble processing all that's happening. But roadhead? I don't know!"

Wendy got on her knees in the car seat. Jim mildly protested when she unzipped his pants and extracted his rigid cock.

"Rodger, I don't...!"

Whatever Jim was going to say was lost when Wendy inhaled his cock. Her head bobbed slowly; she didn't want him to cum, but she did want him to accept that a blowjob was a blowjob, no matter who gave it to you.

Wendy was a world-class cocksucker, honing her skills in men's rooms at train stations and parks over the years. She learned how to suppress her gag reflex. She swallowed her friend's cock and hiccupped, applying pressure with her throat.

She sat up in the SUV and daintily dabbed at her mouth, removing saliva and Jim's precum.

"What do you think?"

"You're better than my wife," Jim admitted.

They reached the building and fairly ran to the apartment. Jim took the key from her, opened the door, let her proceed into the house, and closed it behind them.

Wendy 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 the ass and pulled her close.

Her hand slid between them and grabbed his hardening bulge

"Wendy, be careful! I'm on a hair trigger!"

"Well, we can't have that," Wendy smiled.

She dropped to her knees, undid his pants, pulled them down, and slid his underwear over his hard cock.

She looked up, smiled, and then touched the tip with her tongue, tasting the drop of pre-cum, then ever so slowly, she slid her mouth over his cock.

Standing there watching his cock disappear into her mouth, Jim shuddered. He was never attracted to men, but this was not a man. All he knew was it felt wonderful as she held his balls and pulled him into her. He was already at a knife's edge, and it wouldn't be long before he came

"Oh Lord! Wendy, that's so good, but I'm going to cum soon".

"So, cum then," Wendy grinned up at him. "I want you to last longer the next time, so we may as well clear this up!"

She slid her mouth down to his balls, gagging as his dick entered her throat. She sucked him harder, putting her hands on his ass and pulling him into her with each stroke.

Jim 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! Oh, that's it! Ugghh!"

When 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 sucking him as hard as she could, sucking the last drops of cum from him.

Jim gasped, he was weak in the knees from the intensity of Wendy's blowjob. He had never been blown like this before, and she was still going. Much as he couldn't believe it, his cock stayed 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."

Wendy 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 ached to have his hands on her. She undid her bra and let it fall to the floor.

"I'm a bit small in the breast department. I hope you don't mind," Wendy said, pinching her hard nipples.

Jim surveyed her body, taking in the smooth skin and the stockings. He rationalized that she still didn't look like Rodger, just a tall 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 knelt 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 his reaction to the loss of the illusion. There was no mistaking it was a cock. She held her breath, hoping that the magic would last.

Jim looked at her hardening cock, unsure of how he felt. By now, he was more aroused than he could ever recall. He leaned forward, 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. Her best friend was accepting her as Wendy! The relief of the moment and the joy washed over her letting her abandon herself to his ministrations.

Jim grabbed her ass and pulled her into his mouth as she had him. He was almost frantic now. Nothing mattered anymore. Not that he was sucking his first cock and that it was his long-time best friend. The only thing that mattered was 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, her cock throbbed, and her balls tightened as she began to cum.

"Oh yes!! Jim! Jim! Make it happen! Oh! Oh!"

Wendy was at his mercy, her cock pumping out what seemed like endless jets of cum into Jim's mouth. Wendy felt 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.