Tranny Chasers: Bernie and Ron

Bernie looked around as he entered the Cavalier d'Eon, checking out the patrons. Spying his friend Ron, he worked his way over to him. Ron was sitting at the bar, back to it, also checking out the patrons.

"How's it hanging, Ron boy," Bernie asked, easing between Ron and the guy sitting next to him.

"Low as usual, Bern," Ron replied, turning to his beer on the bar.

The barista came over and Bernie ordered a beer. "Anything interesting?" he asked.

Ron looked at two women sitting together at a far table, like scared deer in a den of wolves, which was exactly their situation. "Looks like two first timers over there."

Bernie followed Ron's gaze. In the dim light of the bar, the two looked to be in their mid-twenties. "Wanna be wingman?" Ron inquired.

"Why not?" Bernie shrugged.

The two picked up their beers and eased their way over to the two women.

"May we join you?" Ron asked when they reached the table.

The two looked at each other nervously, then nodded.

"I'm Ron, this is Bernie," Ron introduced himself and his friend

The two women looked at each other, trying to decide who should speak first.

"I'm Shirley," one of them said in a falsetto that was not convincing.

"I'm Christine," her friend stated, her voice a contralto.

Ron looked them over. Since they were sitting, he could only see that Shirley was wearing a skirt and blouse, and Christine a dress. He couldn't make out colors or styles or accessories. Shirley was blonde, Christine dark. Their makeup was a little overdone: two much blush, eyeshadow, mascara, lipstick. Not garish or campy, just more than necessary. While they looked feminine enough, it was obvious that they wouldn't pass muster in a more well-lighted environment.

"Is this your first time here?" Ron asked.

"Yes," they both said in nervous unison.

"Is this your first time out?" Bernie followed.

Shirley and Christine looked at each other, shock and fear in their eyes.

Ron and Bernie looked at each other, then at the two women. Bernie spoke: "There's only two types of people who come to Cavalier d'Eon. Trannies and tranny lovers. We're tranny lovers, and not ashamed of it. We'd assumed that you were transvestites. If we're mistaken, you have our apologies and we'll leave you two alone."

Shirley and Christine looked at each other again, then at the two men. "We're crossdressers," Christine admitted. Having said it, she sighed as if a great weight had been lifted from her.

"First time in public, or just the first time here?" It was Ron this time.

"Both," Shirley joined in.

"So, how long have you two been at this?" Bernie asked.

"Years ..." "Since high school ..." the two answer at the same time. They looked at each other in embarrassment, then Christine began.

"I've been dressing up since high school. Mainly wearing my mother's underwear under my clothes. After graduation, I got my own place and began dressing up regularly." She then looked at Shirley.

"I started in college," Shirley began, now no longer trying to mask her voice. "I guess I'm gay, although I've never done anything with a man. The university I went to is in Michigan, and the winters are very cold. I read that football players wore pantyhose under their uniforms to keep warm, so I tried it. I enjoyed the feel so I kept wearing them. Then I read about how more sensuous they felt on bare skin. So I began shaving my legs. What I read was right! Well, in for a dime, in for a dollar. I began wearing panties, then stockings and garter belts, then heels, skirts, dresses, bras."

"Did you two know each other in high school?" Ron asked.

"Oh no," Christine gasped. "We met only a few months ago."

"The internet," Shirley added.

"Yeah. Being a crossdresser is lonely." Christine added. "You don't know who to tell, but you want to tell somebody. You want somebody else to see you, to give you feedback, tips, approval. The internet is great."

The two looked at each other with approval, smiling slightly. Christine then looked at the men. "And exactly what is a tranny lover?"

Ron smiled at them. "A tranny lover is a man who loves transvestites." He looked at Bernie, then back at the women. "We love being with them, we love helping them look more feminine. We love helping them act more feminine." He paused and flashed his most engaging smile, "And we love making love to them. Especially their first times."

Again the deer-in-the-headlights look on Shirley and Christine. Bernie chimed in, "Shirley says she's never been with a man. What about you Christine?"

Christine shook her head. She and Shirley then looked at their drinks for a long while. Ron and Bernie said nothing, just sipped at their beers.

Finally Christine spoke up. "So you want to fuck us?"

"Yes!" both men said together.

The women looked at each other, then the men. The lust in their eyes was unmistakable.

"Excuse us," Shirley said, "we've got to go to the ladies."

The men stood as the women left the table, watching them as they wobbled to the ladies room. "At least they didn't go for the door," Bernie said as the pair resumed their seats. They ordered another round of beers and began checking out the other patrons again.

There was a long line to the ladies room. Shirley pushed Christine into a nook and whispered "What are we going to do?"

"I don't know, Chrissy," Shirley replied. "I didn't expect to be hit on, much more picked up. What do you think we should do?"

"How 'bout we take them back to my place and continue to just talk to them?"

"I don't think they'll be satisfied with just talk."

"Well, maybe they won't want us when they see us in the light."

"Gee, thanks!" Shirley spat.

"You got any better ideas?"

"Yeah ... Let's just get outta here!"

Christine thought about it, then shook her head. "No. I came here to see if I can pass as a woman. Not just look like a woman, but carry myself as a woman. These two guys know what we are, and are turned on by it. I want to try entertaining them as a woman."

Shirley looked at her friend. "But what happens when they want to ... you know?"

"Handling that situation is part of being a woman."

Shirley's face clouded. "You mean you'd ..."

"I don't know. But I need to find out. And what to do if I don't want to."

Shirley was still hesitant.

"Look, Shirley," Christine said, "you don't have to come with me. I'll pick one to come with me. You can call a cab."

"You're really going to invite one of them up to your place?"

Christine nodded.

"I can't let you do that by yourself. Just because they look okay ..."

Christine hugged her friend. "Okay, let's go back."

Ron and Bernie rose as the two women returned, a little surprised at seeing them again.

"Let's go outside," Christine said.

Ron and Bernie looked at each other, smiled, then followed the two trannies outside. Christine led them several doorways away from the Cavalier d'Eon.

"My place is several blocks from here. One of you can ride with me, Shirley can ride with the other. This is only for us to talk. If you want something more, then you should go back into the bar and hope to get lucky, or whatever you want to do."

Ron and Bernie looked at each other, smiling. "Wanna flip for who leaves his car here?" Ron asked.

"No, buddy. You take Shirley, I'll ride with Christine."

Shirley and Christine were surprised at how quickly the decision was made. "You've done this before," Christine stated.

Ron and Bernie smiled, Bernie putting his arm around Christine as Ron placed a hand in the small of Shirley's back. The ride to Christine's took about ten minutes. Christine pulled into the security gate first, then had to direct Bernie to the guest parking. Shirley guided him to the space beside her own car. The walk to Christine's apartment was a two minute walk. Christine and Bernie were waiting for them. The quartet then ascended the stairs to her second floor residence.

Christine entered first, turning on the lights, and standing by the door as the other three entered. She closed the door and turned around to have Bernie in her face. He put his arms around her and kissed her. She started to resist, but decided to go with the role. Seeing his friend getting ahead of him, Ron took Shirley in his arms and kissed her. Shirley was also initially resistant, but succumbed. After about a minute, both couples separated. Ron and Bernie looked at each other triumphantly, Christine and Shirley at each other sheep-faced.

"Uh ... have a seat," Christine said, stepping away from Bernie. "Uh, Shirley ..." Christine cocked her head toward the bedroom. The two women left the men.

In the bedroom, Christine turned to Shirley. "How do you want to handle this?"

"How do I want to handle this," shouted Shirley. "This was all your idea!"

Christine put her finger to her lips, trying to quiet Shirley. "I know that, Shirley. They're just a little bit more aggressive than I thought they would be. Should we ask them to leave?"

"Do you want them to leave?"

Christine was undecided.

"Then you don't want them to go," Shirley stated.

Christine sat on the bed. Looking up at Shirley, she confessed, "No, I don't want them to go."

"Then it looks like we're either gonna get raped or seduced." Shirley turned to the mirror over the dresser and wiped her smeared lips. Looking at Christine's reflection she commented, "You need to fix your makeup." She wondered why she was fixing her own, since it was due to be smeared again.

Christine got up and stood next to her, fixing her own makeup. "This is how we started this evening," she giggled.

"Yeah, two girls having a night out. Now we're two guys in drag about to be fucked."

Christine looked at Shirley in the mirror. "You can still back out, Shirley. I wouldn't hold it against you."

"No, if I left, the two of them would rape you for sure." Shirley looked at Christine. "You'd probably like that, wouldn't you?"

Christine said nothing, but the look on her face indicated that she would not truly object to that. The two finished their makeup and went into the living room. Ron was sitting in an armchair, Bernie on the loveseat. They had checked out the living room while the two trannies conversed. In addition to the armchair and loveseat, there was a sofa, two end tables with lamps, a cocktail table, a credenza against the wall, pictures and a throw rug under the cocktail table. The room was fully carpeted. The men stood as the women entered.

"Would you two like something to drink?" Christine offered.

"Nothing alcoholic," Bernie said.

"Yeah ... the beers were enough," Ron added. "Speaking of which, may I use your bathroom?"

Christine nodded, pointing in the direction of the bedroom. The bathroom was right across from it. Christine went to the kitchen, which adjoined the living room, and placed four bottles of blackberry flavored water on the counter separating the two rooms. She took out four glasses and placed them on the counter. She put ice in them, then filled them with the water just as Ron exited the bathroom. Shirley came to the kitchen side of the counter and picked up a glass, taking a sip. Bernie and Ron took their glasses from the living room side, the counter serving as a wall between the men and the women.

Christine and Shirley placed their glasses on the counter, telltale lipstick prints on them. "There is always something sexy about lipstick on a glass," Bernie commented.

Christine and Shirley laughed nervously, looking at their glasses. Bernie picked up his glass and moved back to the loveseat; Ron did likewise moving to the armchair. The increased distance heightened the tension between the two genders. Christine and Shirley moved around the counter, Christine sitting on the loveseat next to Bernie, Shirley on the sofa.

"So what do you two do ..." Bernie and Christine asked simultaneously. All four laughed nervously at this.

"Ladies first," Bernie said.

"I'm in household goods," Christine volunteered.

"Sales," commented Shirley.

"Household goods?" asked Ron.

"Yes. Kitchen gadgets. I have a few here." She got up and went to the kitchen, producing automatic can openers, microwaveware, various kitchen organizers. As she produced the items and explained them, Bernie got up and entered the kitchen, pretending to be interested in each item. Ron moved next to Shirley on the sofa.

The last item Christine retrieved required her to squat so that she could get something from a lower cabinet. When she stood, Bernie was again in her face. He put his arms around her and kissed her again, pulling her body to his. Ron put his hand along the back of the couch in back of Shirley.

Breaking the kiss, Bernie looked at Christine. "I really want to fuck you."

Christine looked at him, then into the living room. Ron still had his arm along the back of the couch, while Shirley was leaning forward. 'Well,' Christine thought, 'if Shirley doesn't want to go further, she's on her own.' Christine brushed passed Bernie and headed for the bedroom. At the doorway she stopped and looked at Bernie, who hadn't moved. Christine raised her eyebrows, then disappeared into the bedroom. Bernie quickly followed.

Christine had her back to him. "Unfasten me."

Bernie began unbuttoning the back of the dress, then pushed it off her shoulders. She quickly pulled in to her waist, letting it drop to her feet. Stepping out of it she sat on the bed and removed her pantyhose and panties. Leaving her bra on, she stood and turned, climbing on the bed on her hands and knees, presenting her ass to Bernie. Bernie reached into his pocket and pulled out a condom packet and some lube, and tossed them on the far side of the bed under Christine's gaze. She looked at them and closed her eyes, letting out a heavy sigh. 'I'm gonna get fucked!'

Bernie then caressed Christine's ass before removing his pants and briefs. He sat down to remove his shoes, then walked to the far side of the bed, presenting his cock to Christine. Christine stared at it. He wants me to suck his cock! She thought. She looked up at him, noting the cocksure look in his eyes. Looking back at his cock, she crawled to close the distance between herself and the cock. Within range, she opened her mouth and took him in. As she slid more of him into her mouth, he slid his hand back until her nose was touching his pubic hairs. She closed her mouth around him and pulled her head back until he was nearly out, then pushed her mouth back to his pubis. Bernie put his hands on the sides of her head and held her still while he moved back and force, fucking her face. Christine knelt there passive, letting Bernie use her mouth. She felt him harden and prepared to taste her first mouthful of sperm.

Bernie felt himself nearing climax. For a first time cocksucker, Christine was doing okay. However, he didn't want to cum in her mouth. He could save that for his second load. And teach her to suck cock properly. He pulled out. Christine looked up at him forlornly, wondering what she had done wrong. He smiled down at her, picked up the condom packet and opened it. He placed the it on his dick and rolled it down. He then picked up the tube of lubricant.

"Turn around," he ordered.

Christine scooted around on the bed to see Ron and Shirley standing in the doorway. Ron had a shit-eating grin, Shirley's mouth was open as far as her skin and muscles would permit. Did she see me sucking Bernie's cock? Christine wondered. Oh my God! She knows I'm a cocksucker! She felt Bernie's fingers on her ass cheeks, then at her ass hole, oily and slippery. I'm being prepared to be fucked, and Shirley's watching. Bernie took his time, inserting one finger, twisting it inside her, then two. The second finger hurt a little and she moaned.

"Look in the mirror, Christine," Bernie commanded. "I want you to look at yourself being fucked. I want you to watch me take your cherry."

Christine looked in the mirror. Her blonde wig was slightly askew. Her blush and foundation were smeared. And all her lipstick was off except a telltale ring around her mouth. She looked above her to see Bernie place one hand on her hip and felt both that hand, and the tip of his cock as it touched her opening. Bernie leaned forward, resting his knees on the edge of the bed, and guided his cock just inside her ass, moving it around without really penetrating.

Christine kept looking at him, wondering when he was going to do it. Out of the corner of her eye she watched Ron move into the bedroom and leaned back against the top of the dresser. Shirley took a step or two inside, and leaned against the door, her arms folded across her chest. The look of disgust on her face was unmistakable. The feel of Bernie's cock rimming her was delightful. But when was he going to fuck her?

Just as the thought occurred, Bernie placed his other hand on her hip and held her tightly. "Push out like you're taking a shit, but don't shit," he instructed.

She did so and Bernie pushed in steadily. She felt a moment of white hot pain that caused her to close her eyes and gasp loudly. Bernie was watching her in the mirror, and when she closed her eyes he pushed all the way in, pulling her back toward him until his hairs were mashed against her cheeks. Christine took several short breaths, exhaling with short moans.

"Are you okay, Christine?" Bernie asked.

"Yes ... yes ..." Christine panted. "It hurts."

"Yeah, I know," Bernie said. "It usually does the first time. Part of being a woman, having it hurt when your cherry's busted. It's gonna continue to hurt until I pull out. Ready?"

Christine looked at herself in the mirror. She had not noticed that she was crying, the tears making her mascara run. She looked at Ron, smirking. She looked back in the mirror at Bernie. He was reading her face to see how he should proceed. She glanced sideways at Shirley, still leaning against the door, her expression unchanged.

"Ready," she said.

Bernie began pulling out as Christine grimaced, then pushed back in slowly. He repeated this, picking up speed until he had established a rhythm and Christine was staring at their reflections, the grimace replaced with a slight smile.

"Mine if I join you," Ron said to Bernie, breaking his rhythm. Without waiting for a response, he stepped in front of Christine and unfastened his pants, pushing them and his boxers down his legs. His cock bobbed in front of Christine. She opened her mouth and Ron guided it to her lips. He pushed it in to the back of the glans, then grabbed her head as Bernie had done. He began fucking her face, matching his movement to Bernie's

"Don't cum in her mouth," Bernie ordered. Ron looked at him, confused. "I want to be her first cum load. I want to take all her cherries."

Ron smiled in acknowledgment, and adjusted his face fucking to keep him hard, without his cumming. After a few minutes, he pulled out and sat on the bed next to her head, removing the rest of his pants, underwear and shoes. He reached into his pants pocket and retrieved a condom packet and tube of lubricant similar to Bernie's.

Christine watched him doing this. "You two really planned on getting lucky tonight, uh?"

"Well, not as lucky as we thought," Ron answered, looking at Shirley. He opened the condom packet and placed it on his cock. He returned to Christine. "Hope you don't mind my taking sloppy seconds."

Just then Bernie gripped her hips tightly and began pistoning in and out of her rapidly. "Yeeahh!" he yelled, holding her ass to his hips, his cock twitching inside her as he filled the condom. He held her to him until he finished cumming. He pulled out after he went soft.

Christine suddenly felt an emptiness. Not just the removal of a cock from her ass, but like something meant for her, something she was made to have, was no longer where it belonged. As she was contemplating this empty feeling at her rear, Ron got up and moved to where Bernie had been and Bernie came around to Christine's face. She felt Ron's hands on her hips, then Ron's cock at her hole. Without ceremony, Ron pushed inside her and began pumping.