Chiara Chronicles Ch. 02

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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, Travesti 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.

Chiara’s date with Nick on Friday went okay but not as well as she had hoped. He’d taken her to The Olive Garden and a movie. She was a bit disappointed though because he seemed to be a bit more into himself than her, monopolizing the conversation and not really seeming to be interested Ankara Travesti in what she had to say. During the movie he’d tried putting his arm around her but she pulled away, not feeling comfortable with his behaviour.

“How’d this one go Kiki?”

“I dunno Annie, he wasn’t exactly what I expected.” Chiara replied.

“Oh, what do you mean? I know I told you before I didn’t want any details but I think in this case we may have to break that rule.”

Chiara proceeded to tell Annie about what happened and she could see that she was getting angrier by the minute. She almost started to feel sorry for Nick, knowing that Annie was going to go after him for breaking the rules of the dating agreement.

“I’m going to rip Nick a new one,” Annie said angrily. “He promised me he’d behave! If you want I’ll cancel your other dates with him.”

“I know you want me to get used to dating different kinds of guys Annie, but Nick just seemed a little too slick for me.” Chiara said.

Annie gave Chiara a reassuring hug, “Okay no more dates with Nick, and I’ll make sure Aaron’s on his best behaviour. I’m really sorry about tonight sweetie.”

Even though she was fuming about Nick and how he had behaved, she knew he was probably trying to impress Chiara with how ‘cool’ he was. Annie was almost glad he’d broken the dating agreement. Now Chiara had seen exactly what kinds of jerks some guys could be and would be even more receptive to Annie’s choice for her.

Saturday went much better for Chiara. When she and Aaron had spoken earlier and he’d found out that she liked to dance he had offered to take her to an all ages dance club out of respect for the fact that she looked very young, thinking that might be a good compromise. Chiara had an amazing time with him. They’d danced all night and every once in awhile he’d come up with a goofy dance step which made her laugh. Aaron’s attention was totally on Chiara and not once did he even try to check out another girl, which she really appreciated. At the end of the night she gave him a goodnight hug and kiss, thanking him very much for a fun evening.

Annie, of course, was waiting for Chiara when she got home that night. “Better?” She asked with a smart-assed grin.

Chiara flopped onto her bed and pulled off her shoes, rubbing her feet. “Way better stretch, Aaron’s hilarious! I think we maybe sat down three times all night. He’s actually a pretty good dancer ya know.”

“Yeah I thought you’d like that about him.”

The following week both of Chiara’s dates with Aaron and Steve went very well again. Both guys treating her like she was a princess, making sure she had a wonderful time while they were out. Chiara was actually feeling brave with these dates and when they dropped her off afterward she made sure that their kisses lasted a lot longer, and didn’t mind at all when she felt their hands gently roam her little body, which sent shivers through her. Having both guys showing their interest in her physically was very exciting to her as she’d never experienced that before.

Annie never even asked her how her dates went. Knowing just by Chiara’s flushed face and quick breathing after both of them that she’d advanced to the next level.

During the week before her final dates Chiara was feeling bummed out. She wasn’t really looking forward to the coming weekend. Her deal with Annie somehow felt very unfair now that she’d had such great dates with both Steve and Aaron. She would have been more than happy to continue seeing either one of them, even though Steve would be off limits after Saturday. She wondered if she could work out a new deal with Annie and maybe see if she could keep dating Aaron after this weekend.

“Annie? I was wondering about this whole three date thing with the guys. I know Steve is off limits after Saturday, but I’d kinda like to see Aaron again.”

Annie looked up from her textbook and gave her one of her evil grins, “Kiki you know what the deal was, you can’t back out of it now. But I’ll make you another deal. Wait until after the Halloween bash, and if you still want to see him you can okay?”

Chiara huffed angrily, “Like I need your permission to see Aaron again? I like him and I’m pretty sure he likes me. If I want to see him that’s my business.”

“I don’t doubt that for a minute pipsqueak, but I don’t want you to settle. Don’t get me wrong, Aaron’s a great guy and you could do a whole lot worse. Just give me another week, that’s all I ask.”

Chiara still didn’t know what was so special about the Halloween party for Annie, but she guessed that she could at least wait that week. “Fine one week, but then I’m calling Aaron.”

“That’s all I asked Kiki. After that it’s all up to you.”

Friday night came and Steve picked Chiara up for their date. He held the car door for her as she got in then climbed into the driver’s side before they headed off to the sushi bar they’d agreed on a few days before.

Chiara was quiet on the drive istanbul Travesti over, disappointed that her latest adventure was soon going to end. Steve could sense her mood and tried to draw her out a bit, not wanting her last date with him to be melancholy.

“Hey Kiki, you know I still owe you that movie. I promise I won’t talk your leg off tonight if you still want to see it.”

“Sure,” Chiara said with a smile. “You sure you’re still okay with a romantic comedy?”

“I have two sisters Kiki, the only time I don’t have to watch romantic comedies is when they’re out shopping.” He chuckled. “Besides they kind of grow on you after a while…like moss.”

Chiara giggled at that, “Eww! Bad mental image Steve!”

“Cool, I made you laugh.” Steve said with a smile.

Chiara’s mood picked up after that and they had fun at dinner. She’d never had sushi before so Steve showed her what he thought she’d like to try. Everything went well until she decided she wanted to try the wasabi.

Later at the movie Chiara didn’t shy away when Steve wrapped his arm around her, and snuggled under it while they watched. At every sad or romantic part she would give a little sniffle, at which point Steve would lean into her ear and ask her if she was still having wasabi issues. Every time he did that Chiara would elbow him in the ribs and tell him to ‘fuck off’ with a giggle.

On their drive back to the dorm Chiara decided that she wasn’t going to let her date end with Steve quite yet so she asked him to take a turn onto a quiet side street. They drove down a bit then she asked him to pull up next to an empty lot.

Once they were stopped she undid her seatbelt and leaned over to kiss Steve. “I’ve had a lot of fun these past few weeks Steve,” Chiara said with a grin once they broke their kiss.

“So have I Kiki,” he replied as he rubbed her back and pulled her in for another kiss.

Chiara decided to throw caution to the wind and let her hand slide down into Steve’s lap where she found his growing erection already straining his jeans. She gave it a gentle squeeze and stroke, just like Annie had taught her to do, which made Steve groan.

Steve pulled Chiara closer as she continued to slowly stroke and squeeze him through his pants. His hand drifted to her chest and he was pleasantly surprised to find that she wasn’t wearing a bra, so his fingers tweaked one of her nipples, making her gasp and pull away from their kiss.

“Oh shit. I’m sorry Kiki, I didn’t mean to push you.” Steve said, worried that he’d gone too far.

Chiara giggled and grinned at him as she squeezed him again. “Jesus Steve your hands were all over my ass last week. Do you really think I’d rat you out for grabbing my boob?”

Steve laughed as well, “Well, yeah I guess you’ve got a point there.”

With a mischievous twinkle in her eyes, Chiara told him to lift his ass as her nimble fingers worked on his belt and pants.

“You know you don’t have to do this Kiki,” Steve said as he hesitated.

“I know,” Chiara said as she grinned and kissed him again. “Now would you just shut up and lift your ass please?”

Once Chiara got Steve’s jeans and boxers down she gently took him in her hand. She stopped for a moment, marveling at the fact that she was sitting in a car holding on to her first cock. She moved Steve’s cock back and forth, getting a good look at it, then grinned up at him again and began to stroke it. It was a bit hard like her ‘Bob’ and Annie’s dildo, but also felt soft and hot.

Steve moaned and leaned his head back as Chiara gently played with him. He knew that she didn’t have very much experience because Annie had warned him about it before they started dating. He could feel Chiara’s small hand slowly stroking him from his base to the tip of his cock and over the head, and couldn’t help but think that whatever Chiara had in mind he was sure he’d enjoy what the little redhead had planned.

Without any warning to Steve, Chiara popped the tip of his member into her mouth and began a steady suction on it as her hand moved up and down him. He tasted a bit salty to her and there was a tiny hint of bitterness, but she kept right on sucking lightly. At the back of her mind she registered that he moaned again, and felt his right hand stroking her back as he murmured encouragement to her. She took it as positive reinforcement that whatever she was doing was making Steve feel good, which was what her goal was.

When Chiara’s mouth dove down and took half of his length in one gulp Steve gasped in surprise. Her small hand kept on stroking him and began to pick up speed while she bobbed her head in his lap and lavished her tongue across the underside of his shaft. He pumped his hips up a bit pushing more of himself into her mouth, which made her let out a soft moan, but she didn’t stop sucking him.

Chiara kept on sucking his cock until Steve’s full length was buried in her throat. All she could think about was how wonderful it felt for her, and how much she wanted to make him cum. Every time her head pulled back her hand would replace her mouth and give him a few quick strokes until she dipped down again. She kept having to gulp every once in awhile as her mouth would fill with his copious precum but she didn’t mind as she liked his taste.

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