Chapter Two - The training of a Tart
It was a couple of days after Chiara and Annie's first time together and they were sitting in their room snuggled up on Annie's bed chatting quietly.
"So Kiki, how many guys have you been with?" Annie asked the little redhead in her arms.
Chiara was surprised by Annie's question at first, "Huh? What do you mean?"
Annie laughed and kissed Chiara on the cheek. "How many guys have you had sex with sweetie?"
"Um, none." Chiara replied as her face grew hot.
"So you're still a virgin then?"
"Well...technically no I guess," Chiara hedged as she turned an even deeper shade of red.
"Good well at least we don't have to worry about that then," Annie chuckled. "How far would you be willing to go with a guy pipsqueak?"
"Hey are you already trying to get rid of me?" Chiara twinkled up at her gorgeous roommate.
"Oh hell no Kiki! I'm just trying to figure out what I need to do to protect you from the dozen or so guys who were eyeing you at the parties we were at during Frosh. You, my little poppet were a lot more popular than you realize. Luckily I know a few of the guys who were gawping at you, and for the most part they're decent guys and not bad in bed either."
"God Annie! The only thing I've ever done with a guy was go to Burger King and catch a movie, and that was two years ago! The guy didn't even want to make out with me for fuck's sakes!"
Annie laughed again and gave Chiara a squeeze, "Okay so one really pathetic date. We're going to have to fix that quick. I will give you this short stuff, you're a natural kisser. You've got nothing to worry about there. So seriously, how far would you go?"
"Uh depends I guess. How far should I go?" Chiara asked, feeling a lot more worried about the whole college dating scene now.
"God didn't your mom talk to you about this stuff Kiki?"
"Well yeah, but I only ever had that one crappy date before. I didn't really think it would be much different here."
Annie shook her head, not really believing that her cute little roommate had no clue exactly how hot a commodity she really was. "Kiki, Kiki, Kiki. You are probably one of the cutest freshmen this year, if not the cutest. Guys are going to start flocking to you like bees to honey. You need to listen to your Auntie Annie and learn how to handle these sharks before they have a feeding frenzy."
"Jesus, maybe I should just buy a bee smoker or some shark repellant?" Chiara joked as she snuggled into her friend's arms.
"Seriously Kiki, enough with the jokes. Would you be willing to give a guy a hand job or a blow job?" Annie asked in a serious tone.
Chiara blushed again, "Sure I guess, if I knew how. But I haven't got a clue of what to do."
Annie tousled Chiara's short hair, rolled out from behind her and went to her dresser, pulling out a dildo and returning to the bed.
Chiara started to laugh when she saw what Annie was showing her. Even in the brief time that she'd known Annie she knew that her roommate had never had a problem finding a willing guy to fool around with.
"What the fuck do you need that for Annie? It's not like you're ever hard up for dates."
"Sometimes I just can't be bothered going out. This little guy comes in handy when I'm feeling lazy." She responded with a devilish grin.
"Sooo...what's the deal?" Chiara asked her.
Annie waggled the dildo in her hand and laughed. "Well short stuff, with my little buddy here I'm going to instruct you on the finer points of male manipulation."
With that Annie proceeded to not only demonstrate manual and oral techniques over the next hour, but also expected Chiara to practice her newfound skills on the toy. Annie was very pleased with her friend's rapid progress in her training. She actually wondered if there was anything sexual that Chiara couldn't do once she set her wicked little mind to it.
"Okay Kiki, I think you've got the whole hand job and blow job thing down pat. Somehow I think when you actually get to sex you're going to be a natural, so I'm not even going to cover that. If it's okay with you I think I'd like to set you up on a date with my friend Steve. He was one of the guys who was interested in you last week."
"Uh, okay. Will I have to do anything with him? Y'know, like what you've shown me today?" Chiara asked hesitantly. She was a little worried about having to perform if she didn't feel ready for it.
Annie laughed and gave her friend a hug. "No. Steve won't make you do anything if you don't want to, but he won't say no if you do. Plus I'd kill him if he did. Of course I'll tell him to be extra careful with you."
---
Chiara was sitting on her bed with her laptop across her legs working on an assignment. She kept checking her notes and typing but occasionally giggled, thinking about Annie's plans to set her up for a date. Her girlfriends back home had offered to set her up on dates after her first disastrous one two years ago, but she'd declined, thinking that the results would be the same.
She couldn't believe the changes that had occurred in her life over the past few weeks. She had been a virtual innocent when it came to sexual matters when she'd arrived at university. Now she was in a Lesbian relationship with her roommate, and that same girl had just taught her everything she needed to know about oral sex, and now Annie was preparing to unleash her on the male populace of their school.
Chiara did remember Annie's friend Steve from the party and had thought he was kind of cute but way out of her league. Annie had assured her that he was a decent guy who was fun to be with and that he would treat her well.
Her thoughts were interrupted when Annie came into their room grinning happily. "Wednesday at seven pipsqueak, Steve can't wait. In fact he was almost drooling he was so happy. I told him no Burger King and anything you wanted to do. He's going to call you later to set things up."
"Already?" She asked, a bit surprised at how fast Annie was setting things into motion.
"The sooner the better Kiki, but I'm only loaning Steve to you for a few dates. He knows already and is more than happy to date you even if it's only a couple of times, although he did seem disappointed." Annie replied with a smirk.
"Gee don't I feel special," Chiara said sarcastically.
Annie laughed evilly, "And so you should poppet, you also have dates on Friday and Saturday. Nick Chalmers and Aaron Smith, both good guys and both interested. Same rules apply with them."
Chiara gave Annie a blank stare for a moment before blowing up. "You've got to be kidding me Annie! What the hell are you thinking? I don't even know these guys!"
"God Kiki, we've got three weeks before the big Halloween party at Tappa Kegga Bru. I don't want you being a little wallflower or shrinking violet and not having any fun when we go."
"Tappa who? What the fuck are you talking about?" Chiara asked, feeling very confused by Annie's rapidfire statements.
"Tappa Kegga...Kappa Kappa Nu. It's Marc...my friend's frat. They throw great parties and we're going okay? Trust me you'll love him...it."
---
Annie was kicking herself mentally. She'd almost blown the whole bloody thing when she was talking with Chiara. She knew she was totally in love with the pipsqueak and would love to keep her forever. But she also knew it wouldn't be fair to her friend to expect her to be in an exclusive relationship with her while she continued to fool around with guys. Her only solution was to set Chiara up with the 'perfect guy' and she knew exactly who he was. Yes, she had set up dates for her friend with some very nice guys, but she also knew that none of them were the little redhead's ideal. She was saving him for the Halloween party. Annie also knew that Kiki was this guy's ideal girl, she was everything that he loved in a girl, smart, funny, sweet and full of spirit. It also didn't hurt that she was a little slip of nothing, which she knew was a major turn on for him. Now she just had to figure out exactly how to get the two of them to meet.
---
Chiara's date on that Wednesday with Steve went very well she thought. He was everything that Annie had advertised him to be. Steve had taken her to a little Greek restaurant not far from campus and they'd had a wonderful time. They never did get to see the movie they'd planned on going to, but had spent much of the evening sitting and chatting long after they'd finished their meal. Chiara had quite enjoyed the evening, Steve had been a total gentleman and had treated her with a lot of respect.
When Steve walked her to her back to her dorm Chiara got a bit nervous. She knew he wouldn't make her do anything, but she felt that since he had shown her such a good time that she should at least give him a kiss in thanks. They talked outside for a few minutes, neither one wanting to take that first step. Finally Chiara looked up at him then reached up and pulled him down for a brief but sweet kiss. When they pulled away Steve smiled at her and thanked her, then confirmed that they would have another date the following week before saying goodnight.
"So how'd it go shrimp? I don't want any gory details, I just want to know if you enjoyed it." Annie asked when Chiara got back into their room.
"It was a lot of fun!" Chiara said with a grin. "We never made it to the movie but ended up talking our ears off at the restaurant. You were right about him though, he really is a nice guy."
"See? Am I good at picking them or what?"
"Well so far so good, we'll just have to see how well you did with the other guys." Chiara laughed.
