The Chaser Pt. 02

The Chaser

Edited by Charlette

Chapter 2: Cassie

Bianca called me from her favorite dive bar. Her speech was somewhat slurred, and she giggled more than usual. She asked me to join her.

"I thought you were having a girls night out." I said.

"We are, but it's just myself and Cassie now, and Cassie wants to meet you."

I had nothing better to do, so I walked the half-mile or so to Tinker's Tavern. When I arrived the lighting was dim, and the air was stale as usual. However, the beer was cold and cheap, so I was not about to complain. I bought a beer and spotted Bianca at a high table. She was sitting next to a young brunette, Cassie, I presumed. The two were looking at photos on a smart phone. I sat down across from them.

"Oh is this your guy?" Cassie asked. "He's cute." Cassie was shorter than Bianca. She was curvier too with larger breasts and softer facial features.

"Only because I tell him what to wear." Bianca quipped.

"Is that true?" Cassie asked.

"Pretty much." I agreed.

"Oh you two are too funny." Cassie said. "How long have you been going out?"

"Just a few weeks," Bianca said, "but we've been friends for, like, forever."

"I think its better that way," Cassie said, "it's good to have trust before you start fooling around. Sex with total strangers can be a bit unnerving, even if they're hot." Bianca looked embarrassed. "What you two aren't--" Cassie whispered into Bianca's ear something that sounded like "doing it?"

"Cassie!" Bianca tried to hide her face in her palm.

"You mean he doesn't--" Cassie circled her thumb and forefinger near her mouth and pushed her tongue against the inside of her cheek.

"Oh my gosh, you are so rude!" Bianca complained.

"Well does he?" Cassie asked.

"Come on stop! You're embarrassing him."

"Are you embarrassed?" Cassie asked me.

"No, not really" I said. I like girls who openly talk about sex. "I think it's Bianca who's embarrassed."

"I think you're right about that," Cassie said, snickering. Bianca blushed, but Cassie continued to press and asked, "So does he suck a good girl dick?"

"Oh my gosh Cassie, you are so exacerbating!"

"You can tell me. You are among good friends here. Nobody is going to judge."

"Okay, okay. If I tell you, will you stop asking sex questions?" Bianca pleaded.

"Sure," Cassie replied.

"He does perform fellatio when prompted." Bianca said, looking away.

"Is he good at it?" Cassie probed.

"We agreed no more sex questions!" Bianca protested.

"I had my fingers crossed." Cassie smirked.

"Oh you bitch!" Bianca shrieked. A few heads turned our way, but the girls didn't seem to notice. I, of course, didn't really care. I found these two quite amusing.

"Slut!" Cassie countered.

"You're one to talk! How many guys have you slept with? Like a thousand?"

"It's under a hundred." Cassie said.

"Wait," Bianca snapped, "that's not right. Just last week you said it was nearly a hundred and fifty."

"That number includes both boys and girls," Cassie explained, proudly. The two were silent for a while, but then started laughing. "He seems like he'd be good at it." Cassie said.

"Good at sucking cock?" Bianca asked. "Why would you say that?"

"He has a really big mouth. Looks like he could fit a lot of cock in there."

"He does, doesn't he? I was just telling him that the other day." Bianca said. Cassie raised an eyebrow in my direction.

"She did say that. I was totally offended."

"No you weren't." Bianca protested.

"So you can fit her whole dick in your mouth?" Cassie asked.

"I tried, but it's too big."

"No it's not, it's average." Bianca said. "You just think mine is big because yours is small."

"Hey, you shouldn't dick shame your guy," Cassie scolded. "You'll give him a complex."

"Oh, sorry!"

"Does he swallow?" Cassie enquired.

"Swallow what exactly? My dick or my cum?" Bianca asked. At that point, she seemed a little more comfortable with sex talk.

"Either makes for good conversation." Cassie winked at me.

"He can only get it about halfway down his throat before he gags and chokes."

"At least he's trying," Cassie said. Turning to me she added, "I think you need more practice."

"Yes," I agreed, "but perhaps on something smaller."

Cassie turned back to Bianca. "You hear that? Now you know what to get him for his next birthday. I'll take you to the sex shop, and we'll buy him a small dildo."

"My birthday isn't for another ten months." I explained.

"Maybe he could just practice on himself." Bianca snarled.

"Most guy's can't reach," Cassie said, "and even those that are capable can barely lick the tip."

"I can press mine against my tonsils." Bianca claimed.

"You can suck your own dick?" Cassie said, shocked.

"Why didn't you tell me?" I asked.

"You never asked." Bianca replied.

"If you can get it in that far, you must be big! Or at least long!" Cassie said.

"No, I'm average. I'm just really flexible. I can even do the splits."

"Oh, I'd like to see that!" Cassie said.

"Me too!" I agreed.

"You've seen me do the splits before."

"But only with your clothes on." I explained.

"Oh stop!" Bianca rolled her eyes. "You two are both perverts."

"I don't think she's really offended." I said to Cassie in a hushed tone.

"I don't either." Cassie agreed.

"Can we not talk about me doing the splits while naked?" Bianca said nervously. "I think that some of the people around us are listening in." Looking around, I noticed that there were, in fact, several sets of eyes directed our way.

"Of course there are!" Cassie said. "The three of us are young, hot, and fascinating. Still, I don't know why you find the subject so uncomfortable?"

"I do." I said. "I always feel uncomfortable when I try to do the splits."

"You and me both!" Cassie said, laughing.

"Please, let's talk about something else." Bianca pleaded.

"Okay, okay," Cassie said, trying to placate Bianca. "We won't talk about the splits. What were we talking about previously?"

"Swallowing." I blurted.

"That's right! Does he swallow your cum?" Cassie asked, straight-faced. Bianca nodded somewhat shyly. "Oh it's good to swallow." Cassie said. "That means there's less mess to clean up later on. Do you swallow your own load when you suck yourself?" The question was directed at Bianca.

"No, I catch it in a Kleenex."

"Oh, you are just too funny!" Cassie said, laughing.

"She is," I agreed. "I'd totally swallow my own load if I could reach."

Cassie turned to me. "What about her?" she asked. "Does she--" Cassie repeated the blowjob gesture from earlier.

"Oh, I haven't gotten around to it yet." Bianca said, effectively spilling the beans. "I'm pretty new to this whole sex thing."

"Yeah, but you've already admitted to practicing on yourself! Why not just suck his?"

"It's different when it belongs to somebody else."

"I suppose that makes sense." Cassie said. "Why did you wait so long before you started fooling around with guys? I mean, you're so hot! Don't you think she's hot?" Cassie asked me.

"Totally," I beamed, "I wouldn't suck her dick otherwise. Unless maybe, I owed her money or something." The girls found this simply hilarious. Bianca laughed so hard she snorted.

"Oh look! She snorts." Cassie said. "How cute!"

"Isn't it now?" I agreed, smiling.

Cassie asked again, "so, why did you wait so long to start this whole sex thing?"

"I guess I really wanted to sprout tits first." Bianca explained. "I know it's silly."

"No I get it," Cassie said, "you wanted to feel more comfortable in your own body before you started getting naked in front of other people. That makes perfect sense." The three of us spent the next few minutes looking thoughtful while nodding, not really knowing what else to do. We had reached a non-verbal consensus that Bianca had good reason to postpone sexual activity into her mid twenties. Of course Cassie couldn't leave the sober mood alone for too much longer and promptly killed it with, "does he give rim jobs?"

"What's that?" Bianca asked naively. Cassie cupped her hand and whispered a description into her friend's ear. "Yuck!" Bianca exclaimed, "That's disgusting!"

"Maybe a little," Cassie said, "but it is to die for when you get past your inhibitions. It feels totally amazing! You've got to try it!"

"No way!"

"Look at him," Cassie said, pointing at me. "He's totally game for it. I bet he can't wait to get you home, bend you over, and lick your asshole raw."

"You wouldn't, would you?" Bianca asked. I nodded, but mostly for shock value. "Well, don't expect a kiss on the lips afterwards." She said. We all laughed at that one.

"Does he top?" Cassie asked, building on the fantasy expanding in her sex crazed mind. "He seems like he tops. Wait, maybe not! If he'll suck your dick, and you're not sucking his, he probably bottoms."

"What's a top?" Bianca asked, predictably.

"A top likes to penetrate," Cassie explained, "while a bottom takes it up the ass."

"Oh I tried to top, but I only got the end in before he started screaming like a little girl."

Cassie laughed hard and slapped the table. "Oh, that is just too funny! The same thing happened to me the first time I tried to top a guy."

"Wait, you're trans too!" I asked in near shock. "What are the chances of that?"

"Considering we met at a transgender support group, I'd say pretty high." Cassie explained.

"Oh," I said, feeling rather stupid. It's something I should have known already given how much Bianca talks about her friends. Perhaps I wasn't listening intently enough.

"But no fuss," Cassie said, putting me at ease, "let me guess what happened. You figured you'd do what you saw in porn movies, and you tried to just shove your dick up his ass?"

"That's exactly what happened." Bianca said. I nodded.

Cassie shook her head. "You two are so damned naïve. That's just not how the ass works. There's a lot of prep work to be done beforehand, but they seldom show it in pornos."

"Prep work?" Bianca asked.

"Yes, you've got to get your partner to relax, and you need to get everything down there all loose and lubed up."

"You need lube?"

Cassie shook her head and rolled her eyes. "Oh my God, you didn't even consult the internets did you?"

"No," we both said.

"I guess we were trying to be spontaneous." Bianca explained.

"You can't be very spontaneous with anal," Cassie instructed, "and you need lube. Lots of it, or it's going to hurt."

"Where did you learn all this?" Bianca asked.

"Friends mostly, when I was in a similar situation as the two of you are right now. Also there are some good websites."

"Like what?"

"Well, let's see there's 'Backdoor Buddies,' 'Buttsex.com,' the aptly named 'How to Have Anal Sex,' and 'Anal University,' just to name a few."

"There's an Anal University?" Bianca asked in total shock.

"Yes, but it's more of a virtual program, and I don't expect it's fully accredited." Bianca and I laughed, but Cassie remained silent. Her demeanor had changed. She seemed pensive.

"What?" Bianca asked, sensing the change in her friend.

"Oh, nothing," Cassie said, "I was just thinking."

"Thinking about what?" Bianca pressed.

"No, I shouldn't say it." Cassie's expression changed from serious to mischievous. I could tell she was baiting Bianca and that Bianca was completely clueless.

"Oh no you don't! Now you have to tell us!" Bianca commended, springing the trap.

"Okay, okay," Cassie said with faux resignation. "If you really want a useful hands-on experience. We could go back to my place, and I could walk you through it."

"You mean we'd have to--"

"Get naked in front of me? Yes, but you should total remember I have so much experience that I'm practically a licensed sex therapist."

"And you've got--"

"Toys, lube, everything we will need."

"I don't know," Bianca said apprehensively. "I'd feel okay doing it in front of you. I mean we're pretty good friends and all, but I don't know about him. He hardly knows you."

"I'm okay with it. She doesn't seem the type to write about me on bathroom walls, but it's your call." I replied. I was hoping for a 'yes.' It would be such a cool kink.

"Gee, I'm still not sure." Bianca said, "It might be kind of awkward but..." she leaned forward a bit.

"But what?" Cassie and I asked.

"I really want to fuck him up the ass." Bianca said softly.

"We'll then it's agreed." Cassie gleamed with happiness. "We shall retire to my place?"

"You live nearby?" I asked.

"Just around the corner, but you should probably get your self a beer first. It will help calm your nerves."

I was more thrilled than nervous, but I got up to grab a beer anyway.

"Oh while, you're at it, get me one too, bottom boy!" Cassie called after me.

Bianca snickered. "You called him 'bottom boy,' that's funny."