Tranny Chasers: Shirley and Chrissy

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Now it's Shirley's turn.
13.4k words
31k
22

Part 2 of the 2 part series

Updated 08/30/2017
Created 05/14/2008
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1946EW
1946EW
43 Followers

Shirley looked around as she entered Cavalier d'Eon, hoping to spot Ron and Bernie. She had promised that she would be there, and fully expected them to be waiting for her. Her survey caught the eye of many a hopeful tranny chaser. She had not known of the breed a week earlier, now she could spot them with ease. And there easily were over a dozen or two at the club. She saw that the table she and Christine had sat at last week was empty, and she eased over to it.

She was looking at the door when a tall figure eased into the seat next to her. Turning she saw a strikingly attractive blonde woman, face like an ad for a Nordic airline or cruise line. Her hair was in a French curl, with bangs. "I'm the Cavalier d'Eon," she said.

Shirley's eyes widened in amused surprise. She thought that was merely the fancy name of the club, and didn't take her uninvited guest seriously. The Cavalier was not deterred.

"Yes, I know that look, young lady. But I am the proprietress of this establishment, and therefore I am the Cavalier d'Eon, both in person, and as the corporate entity that you're sitting in."

Shirley now understood. But why was she at her table?

"Are you looking for Ron and Bernie?"

"Uh ... yeah."

"Where's your friend?"

Shirley was now a little put out. "Uh ... Ms.?"

"Just call me Cavalier."

"Uh, Cavalier ... I really don't think that just because you own this place that I have to divulge my personal life to you."

The Cavalier smiled, mischievously. "No, you don't. And I can throw you out right now."

Shirley stiffened, and looked at the Cavalier. She wasn't sure whether the Cavalier was saying she would personally throw her out, or have one of her bouncers do it. She reached for her purse.

"Relax, young lady," the Cavalier continued. "I keep close tabs who comes and goes here. Last week I see two trannies obviously new to dressing up and going out come in here, and leave with two of my most lecherous tranny chasers. Three hours later the chasers are back picking up two regulars. I figure things didn't work out—they often don't—and that I've seen the last of you two. Now one of you returns, looking for the guys. I'm curious—and concerned."

Shirley looked into the Cavaliers steel-blue eyes, seeing both the concern and the curiosity. "My friend is at my place, waiting for me and Bernie and Ron."

"Why?"

Shirley didn't really know how to answer the question. "I ... I ... don't understand what ... you ..."

"Why are you here, and why is she not here, and why is she waiting for the three of you at your place?" the Cavalier insisted.

"Uh ... well ... we decided that we'd rather ... entertain ... the guys at my place rather than here."

"Entertain?" the Cavalier asked, raising a well-arched eyebrow.

Shirley looked down, then defiantly at the Cavalier. "Have sex with! Is that what you want to hear?"

The Cavalier smiled, "Depends. Did they fuck you two last week?"

"No ... yes ... no," Shirley stammered.

"Which is it?"

"Uh ... they fucked Christine, but not me."

"Why not?"

"I wasn't ready for that. Especially the way they did Chrissy ..."

"And you're ready for that now?"

Shirley looked defiant again. "Yes. ... well mostly." The Cavalier raised her eyebrow again. "I mean, I'm ready to be fucked, but not just taken like a slut."

"And that's how they took your ... Chrissy?"

Shirley nodded.

"Well, young ... what's your name?"

"Shirley Qua ... Shirley."

"Well, Shirley Qua," the Cavalier smiled at her own cuteness, "Ron and Bernie are pretty easy to deal with. Which is why I let them operate out of here. They aren't gonna rape you, or slap you around, or call you a bunch of names. They're not gentlemen, but they're not goons. I took you two as CDs looking to become sissies. Your friend made it, and it seems you're gonna join her tonight. Ron and Bernie are about as safe a way to become a sissy as any, I guess. But you better lay out your ground rules before you're outta your panties or you'll find yourself with a cock up your ass and another down your throat wondering why they're treating you like a slut. I guess 'your Chrissy' found that out."

The Cavalier looked at the door and nodded. The bouncer then ushered in Ron and Bernie as the Cavalier got up and returned behind the bar. Shirley noticed that she was over six feet tall, maybe 6-2 in her stocking feet, as they say. Shirley also noticed the Cavalier was dressed as a courtesan in a 17th century French court, complete with hoop skirt, which she managed to maneuver around the tables with ease, patrons parting like the Red Sea before her. Ron and Bernie looked at her suspiciously as they went to Shirley.

"What was that all about?" Bernie asked.

"I'm not sure," Shirley replied, "you two came back here last week?"

Ron and Bernie were surprised, and turned and looked at the Cavalier, who just stared back. Ron spoke first. "Well ... we'd thought we'd scored with you and Christine. As you know, things didn't exactly work out."

"I don't know that, Ron," Shirley said, now angry. She looked at Bernie. "You took Christine's virginity ..." She then looked at Ron, "I practically promised you mine."

The two guys looked at each other, sheepishly. Ron spoke again. "Look, Shirley. We're two very horny guys. Cumming once a night ain't enough. We needed more. Besides, we didn't know if you'd show up, if we'd ever see you or Christine again!"

Bernie now spoke. "By the way, where's Christine?"

"She's waiting for us," Shirley stated.

Bernie and Ron grinned at each other, then at Shirley. "Then we're still gonna party?" Bernie asked.

"If by 'party' you mean will you get to fuck us, yes we're still gonna party. But not like last week." Shirley looked toward the Cavalier. "There's going to be some ground rules."

"Ground rules!?" the guys said in unison.

"Yes, ground rules."

"What sort of ground rules," Ron asked, uneasy.

"Nothing special. Just things to make sure you treat us like ladies, not like sluts. Not like you did last week."

"I thought we'd treated you trannies alright," Bernie said.

"That's what I'm talking about," Shirley said. "Calling us trannies. We're ladies. And I expect to be referred to as such."

Ron and Bernie looked at each other. "Sorry. You're a lady. I'll try to remember that." Ron said.

"You'll do more than try, Ron, or you'll never get into my ass!"

Ron began to think her ass wasn't worth it. Damn! She's as bitchy as a real woman.

Bernie was more receptive. "Okay, okay, Shirley. You and Christine are ladies. But can we please leave. I really need to see Christine again."

Shirley looked down at Bernie's pants, his arousal quite evident. "You get that way just thinking about her?"

"Yes!"

Shirley smiled smugly. This was going to be easier than she'd hoped. Men. Once their dicks get hard their ability to reason—or resist—ends. She reached into her purse and pulled out a business card. On the front was the name of Sheldon Quarles, marketing consultant. On the back was an address. She handed it to Ron.

"That's my condo. I'll meet you there." She then eased pass them and out the door.

Ron looked at the card, then at Bernie. "I'm not to sure about this."

"Well, I am," Bernie replied, taking the card. He started toward the door, "You coming?"

Ron shrugged and followed his friend out the door.

* * *

Christine opened the door, wearing a sea green terry-cloth robe. She put her arms around Bernie and kissed him as Shirley and Ron eased pass them into Shirley's living room. Shirley's condo was much bigger than Christine's apartment, and more lavishly appointed. She had two full sofas, one commanding a wall at right angles to the door, another in the center of the room as part of a sofa/love seat/two arm chairs/cocktail table/2 end table/credenza set; the credenza was in back of the sofa, dividing the living room. A corner of the second part was an office, where Shirley had a desk and her computer. There was also a large flat-screen plasma TV on the wall facing the center set. Christine had some type of video playing.

The video showed two persons laying on a bed, 69 fashion, sucking each other's dicks. One was blonde, the other dark. The blonde was wearing a baby doll outfit, the panties around her ankles, the dark one a nightgown, gathered around her waist. The camera was in a stationary position, since it showed only the one angle, from above, at a distance. The two CDs sucked at each other rather inartfully, the dark one slightly better, until they evidently came. They then sat up, smiling through lipstick-smeared mouths at the camera. It was Christine and Shirley.

Christine and Shirley were sitting on the center sofa; they looked at the guys in anticipation. The guys in turn looked at the TV screen, then the women, in shocked awe. "When did you make this?" Bernie asked.

"Sunday," Shirley replied. "Christine and I had been making out since you two left ..."

"Kicked out." Ron said. "You kicked us out."

Shirley frowned at him. "I didn't kick you out. You'd had your fun with Chrissy and the evening was over. We needed some girl time. That's all."

"Ummph," Ron fumed.

"Okay," Bernie joined. "So you and Chrissy had some girl time. When did you began doing each other, and why show us?"

"Well, we started after you two left," Shirley continued. "Neither Chrissy or I knew what a cum slut she'd turn out to be once she gave in to you. I'd always wanted her, but didn't know how to approach her. Once you broke her in, Bernie, everything was go. I really wanted to do a 69 with her, and once we had done it, I thought we ought to tape it the next time. I have a camcorder, so we did it. I thought you guys would enjoy it."

Bernie looked at the TV screen again. Shirley had rewound the CD and was playing it again. "Looks like you don't need us," he said.

Shirley looked at the TV until the part where they shot into each other's mouths. "Well, Chrissy doesn't. I can take care of all of her needs ... except one. But I'm still a virgin. And I don't want to be." She looked at Ron, then Bernie. "I'm ready for one of you to bust my cherry.

"This is not going to be like last week, like you did Christine. One of you will take my virginity. After that, the other one can fuck me. The question is which one makes me a woman. And I mean exactly that. I want to be fucked as a woman, on my back, missionary style. Have either of you fucked a crossdresser that way?"

Bernie spoke first. "Yeah. We've had trannies that way. In fact, I usually have trannies that way." Shirley looked daggers at him. Bernie took the hint. "You ladies like being fucked that way, and I have no problem with it. In fact, it's preferable to me."

Shirley looked at Ron.

"Like Bernie said, we've done you ladies that way. I don't have a preference, as long as I get to fuck you ... or Christine."

"Such a gentleman," Shirley said, sarcastically. "Bernie, come stand in front of me."

Bernie complied. Shirley opened his pants and took his cock in her mouth, going down on him as far as she could, then sucking back up until he was out of her mouth. She then grabbed he shaft and rubbed the head around her lips, kissing it. She turned to Ron, her lips smeared with Bernie's pre-cum.

"Kiss me."

Ron looked at her and hesitated.

"Kiss me," Shirley repeated.

Ron bent forward hesitantly, then stopped.

Shirley turned to Bernie. "Kiss me."

Bernie dropped to his knees and grabbed her, kissing her in a bear hug. After several minutes he broke the kiss.

She turned to Ron. "If I hadn't promised to let you fuck me, you'd be out the door right now. I'm not a tease, but I'm not a cum slut either. If you can't kiss me after I've had Bernie's dick in my mouth, then I doubt you'd want my dick in your mouth. And I intend to have my cock sucked before I'm fucked. And I'm gonna cum."

She stood and turned her back to Bernie, who quickly unfastened her dress and pushed it off her shoulders. Shirley quickly pushed it down her body, stepped out of it. She was wearing a bustier, wine red, matching panties, stockings. She turned around and removed her panties. She sat on the sofa, legs spread, her arms along the back of the sofa. Facing him was her rampant cock.

Bernie dropped to his knees and took her into his mouth. He slowly licked and sucked Shirley's entire cock, deep-throating her stiff dick. He pushed her legs up and over his shoulder, giving him access to her balls and the area behind them. He rimmed her asshole with his tongue and his fingers.

Shirley tried to remain nonchalant, watching Bernie bobbing between her legs. She noticed the difference in technique between Bernie and Christine, Bernie being much better. He deep-throated, which Christine had not mastered. He sucked harder. He used his tongue more—on the glans and the underside. He rimmed her asshole. For the first time Shirley had second thoughts about kissing him. But she'd set the conditions: if kissing her after she'd sucked cock was a requirement of getting into her ass, then she couldn't very well refuse to kiss someone who had rimmed her.

Bernie had unfastened his pants as he sucked Shirley, working them and his briefs down his legs when he rimmed her. He knew she wanted to cum first, and was trying as hard as he could to make her cum. But he had his needs too.

"I need to fuck you," he yelled, looking at her in desperation.

Shirley looked down at him. She was still some way from cumming, but took pity on Bernie. He really was trying to make her cum, and he could always continue later. She lifted her legs from his shoulder, exposing herself. Bernie stood and began to remove his clothes when she swung her legs to one side and stood up. Bernie looked at her in wonderment.

"The bedroom," she said, walking across the living room. Bernie quickly kicked himself free of his pants and shoes and followed, his cock leading.

Shirley's bedroom was nearly twice the size of Christine's. In place of Christine's double bed, Shirley had a California king. Instead of a dresser, a walk-in closet whose doors were mirrors. She had turned the covers back before leaving, revealing her satin sheets and a love pillow in the center. As Bernie entered, Shirley was already in position, on her back, ass raised on the pillow, legs splayed, encased in her stockings, her hard cock pointing upward, framed by the garters of her bustier.

Bernie nearly jumped on her, but stopped, realizing he hadn't clothed his cock. He looked down at himself, and Shirley followed his gaze. She rolled to the edge of the bed and opened the drawer of her nightstand. Rifling through it quickly, she produced a condom and some lubricant. She resumed her position as Bernie prepared himself. Prepared, he turned and looked at her, debating whether to apply lube to her asshole. He knew he should, but he really needed to cum. He applied more lube to his cock and climbed on top her.

Shirley was breathing heavy in anticipation of being deflowered. She grabbed her cock and began to stroke herself slowly. As Bernie climbed on top of her she realized he'd not prepared her for his entrance; she didn't care. She closed her eyes and pursed her lips as she felt his cock at her hole, then the back of her eyelids went white as he entered her. Her entire being was centered around her asshole.

Bernie collapsed on top of her as he entered her, driving all the way home. As his hairs contacted the cheeks of her ass, he began spurting. He felt her breath on his cheeks and covered her mouth with his, invading her mouth with his tongue. He kept her pinned that way until he finished cumming.

Shirley lay there, feeling Bernie's cock twitching in her burning asshole. She tasted herself on his lips when he kissed her. Her cock was trapped between them, still hard. But she was no longer a virgin! She was being fucked!

Bernie felt himself going soft, raised himself off her and pulled out. He rolled over beside her. "Sorry, Shirley. I haven't cum since Friday. A whole week. I'm not usually quick on the trigger. I'm really sorry."

Shirley lay there, her cock now pointing skyward. She had been fucked! Not as good as she had wanted, but the deed was done. She listened to Bernie's apologizing, thinking So this is what women put up with when a man underperforms. She hadn't changed her position; she just lay there. She felt something warm and wet on her cock. Looking down her body she saw Bernie's head. He was kneeling at her hips, sucking her cock. She turned on her side to give him better access. He adjusted his position, bringing their bodies into a sixty-nine. Shirley removed the condom and took him into her mouth.

##

Christine had led Ron to the rear sofa when Bernie began sucking Shirley's dick on the center sofa. Unknown to Shirley, the rear sofa was position to be captured by the computer's webcam. Christine was sucking Ron hard when Shirley and Bernie went into the bedroom. She stopped, leaving him on the verge of cumming, and went to the center furniture set. Ron stood there open-mouthed, his cock bobbing, as he watched her pick up the tuner and flick it at the TV. The image of Shirley, her white skin against the deep red of her satin sheets, her bustier and garters and stockings dark against her skin. They watched as Bernie fumbled getting the rubber on, then jumped on Shirley. They were disappointed that the further action was just Bernie bobbing on top of Shirley then his rolling off of her. Christine removed her robe and returned to Ron.

Christine resumed her seat on the sofa, pulled Ron to her and ingested his cock. She worked it in and out of her mouth, licking, sucking, nibbling, kissing, stroking. Damn she's learned to suck cock! Ron thought. Christine looked at the screen as she sucked Ron. She saw two people in a sixty-nine sucking each other's cocks and thought the tape of her and Shirley was replaying itself. Then she realized that the pair on the screen was not her and Shirley.

"Yesssss!" Ron hissed as he came in Christine's mouth. Christine swallowed until he stopped cumming, keeping her eyes on the screen. She perfunctorily licked him clean, then concentrated on the screen as Ron slumped on the couch beside her.

She realized the couple sixty-nining were Shirley and Bernie. Christine felt pangs of jealousy. Sixty-nining is what she and Christine do, what they'd done every night for the past week, here and at her place. This is how they went to sleep and how they woke in the morning, their special thing, something they had not done with others. Now Shirley was cheating on her! Or so Christine thought. They had never declared sixty-nine their thing. They had never promised to never do it with anyone else. Like Shirley fucking her missionary-style. It didn't have to be said! How would Shirley like it if she let Ron fuck her that way?

She looked over at Ron; his cock was still soft. She went over to the credenza and picked up a condom and some lube from the stash she and Shirley had placed there earlier. She returned to Ron, kneeling before him. She began mouthing his cock, knowing it would take some time before he could perform again.

###

Shirley licked Bernie clean, but could not really get into sucking his cock since he was doing a great job of sucking hers. She held his cock just beyond her lips, breathing heavily on it as Bernie sucked her, fondled her, licked her. "Oh my God!!" she exclaimed as Bernie used one of his practiced suck and lick techniques on her glans and pee slit.

Bernie knew he had her close. He ran his tongue along the underside of her dick, followed by his thumb rubbing furiously as he sucked and tongued her cockhead. Christine didn't suck dick like this. Shirley tried to hold back, but Bernie was too good. He locked his mouth around her cock and jacked the shaft; she came, hard.

1946EW
1946EW
43 Followers