Training Cristi

Barbara was in the dildo section again, holding a monstrous realistic model, considering it. She looked confident, like she was picking out a toaster, Cristi thought. Cristi strode up to her, grinning.

"You had fun, didn't you?" Barbara said, smiling. "Oh my god, Barbara," she replied. "It was fucking amazing. I came so hard."

"Did you hold off like I told you?" Barbara asked.

"Yes," Cristi said. "The first few times were really hard, but once I got the hang of it...wow!"

Cristi told Barbara how she had learned to edge herself, and of the mini-orgasms she had before finally letting go. "I can't believe how hard it made me come," she told her.

"I'm glad you had fun, sweetie," Barbara said. "Are you ready for your next assignment?" she asked. "If you like that, you'll *love* this."

"Ooh, what now?" Cristi asked, excited. "A bigger toy?"

"No," Barbara said, laughing. "It's smaller."

"Oh," Cristi replied, disappointed.

Barbara selected a small, black dildo from the wall. It was skinny at the tip, increasing in size towards the base where it abruptly thinned again, ending with a flat disk.

"That doesn't look very fun." Cristi said, frowning.

"Oh, but it is," Barbara said in a low tone. She looked into Cristi's eyes and handed her the toy. Cristi melted at the sound of her voice. She suddenly had the urge to kiss her, right there in the store.

"What do I do with it?" Cristi asked quietly.

"I want you to get yourself nice and wet with your vibrator first - but don't come yet, ok?"

"Ok"

"Then I want you to put lots of lube on your new toy, ok?"

"Ok"

"Then," Barbara said, leaning over to whisper in her ear, "I want you to slide it in that sweet little ass of yours."

"What?" Cristi said, recoiling. "That...that's gross!" she exclaimed.

"I know, I know, it sounds nasty," Barbara said, brushing a stray wisp of hair from Cristi's forehead. "But you have to trust me on this."

"Is this supposed to feel good?" Cristi asked, turning the dildo over in her hands.

"You have no idea."

"Will it hurt? It looks like it would hurt."

"A little, at first. You'll need to use lots of lube and take your time. Take deep breaths, and bear down, like you were going to the bathroom."

Cristi looked at her and sighed. "If you say so."

"If you want, you can pretend that I'm there, helping you," Barbara said, and brushed the back of her hand across Cristi's cheek.

Cristi turned crimson. "I don't, I mean..."

"Ok," Barbara said, smiling. "See you Wednesday then, same time,"

"I'll be here."

Cristi drove home, thinking about the strange new toy on the passenger seat. She had never been turned on at the thought of sticking something up her ass, but she trusted Barbara. She remembered what Barbara had said about helping, and her mind filled with a vision of Barbara pressing the black dildo into her. Cristi felt herself getting wet.

She arrived home and opened the door to her apartment. Her roommates had gone out for the evening. Good, she thought. This might get loud.

Cristi took the black dildo out of the box and looked at the packaging. The label read, 'Anal Trainer'. She held the dildo in her hand. It was soft, but heavy for its size. Cristy laid it on the bed and took the red vibrator from her nightstand. She placed a small amount of lube on the vibrator and clicked the button twice, to its medium setting, then ran it gently up her slit. Cristi shivered and nuzzled the tip between her lips, slowly pushing the vibrator into her wet pussy until the knob was against her hard little clit. She moaned, and began softly grinding against it in slow circles. Cristi clicked the button twice, and the vibrator shot quick pulses into her. She began to grind faster, until the orgasm began its slow crawl into her loins, then stopped, letting the warm waves wash through her body.

Cristi turned off the vibrator and pulled it out, then reached for the black trainer. She squirted lube over it, and rubbed more on her ass. Cristi lifted her legs and nestled the tip against her anus, then gave it a tiny push. It feels good, she thought, and she pushed it a little harder. The soft rubber tip slid into the first 1/4" of her rectum. "Oooo," Cristi cooed, "that's nice."

She began making short little thrusts, letting the dildo just barely enter the outside of her ass. She stopped, and gently pushed the trainer in an inch. "Ow,ow," she complained, and stopped the dildo's progress, pulling it out a bit. She relaxed and took a few deep breaths, then slid it back in. No pain this time. Cristi started sliding an inch of the dildo in and out of her tight little asshole. She began to moan. This is amazing, she thought, and drove the trainer deeper into her ass, the widening girth spreading her tight little hole apart. "Fuck," she groaned, and pushed it deeper, until the dildo was almost all the way in.

She took the bottle of lube, and craning her neck, squirted it over the trainer. She lay back and spread her legs further apart, then pushed the final inch of the dildo into her ass. "Ohmyfuckinggod," she moaned, as her stretched hole spasmed around it. She lay still for a moment, allowing her ass to become accustomed to the strange object inside of it.

Cristi reached for the red vibrator and turned it on. She touched it to her open pussy, and immediately felt her ass clench around the trainer. Cristi held it there, panting, then began sliding it up and down her slick, wet opening. She thought for a moment, then, biting her lower lip, slowly inserted the vibrator into her cunt.

Her head snapped back, and a loud, guttural moan escaped her lips. She felt full, ready to burst. Her ass squeezed the trainer and it began to slide out of her. She reached between her legs and pushed it back in, holding it in place. Having both of her holes stuffed felt incredible. Her pussy was now dripping, the juice running out of her and over the trainer.

She began to fuck her pussy with the vibrator. Her eyes closed, face pointed into her shoulder, her voice now one long, continuous moan. She clicked the button to the rapid-pulse setting, and began to grind her hips. Cristi gripped the trainer and began to slide it in and out of her ass while grinding against the vibrator. Her cunt twinged. She was going to come. She held back, slowing the movement of her hips, but continued to fuck herself with the trainer. Her virgin ass had accepted the object, and it now was loose enough to allow Cristi to take deep plunges in and out of it. Cristi began grinding against the vibrator again.

She felt herself go over the edge, unable to stop. She bucked against the vibrator, plunging the trainer in and out of her ass with deep, furious thrusts of her arm.

The orgasm ripped through her body in a violent shudder. She felt her ass contract over and over again around the trainer. Her entire body felt like it was coming, every nerve and muscle ablaze. The orgasm seemed to go on forever, before finally beginning to wane. Her ass continued to spasm around the trainer as the orgasm faded.

She turned off the vibrator and lay back, her head spinning. She was covered in a fine layer of sweat. Cristi could feel a cold wet spot under her ass. She looked down over her abdomen, between her legs, and pulled out the vibrator, then slowly, gently slid the trainer out of her ass, crying out as it left her rectum. She slowly got off of the bed, her muscles stiff from the orgasm's relentless contractions.

Her ass didn't hurt too badly, she thought, as she made her way to the shower. She stepped in, taking her toys with her and letting the hot water run over her body. She soaped herself and the toys, then washed her bottom. She inserted a finger into it, amazed at how the trainer had loosened it.

She smiled, thinking how far she'd come in a few short weeks. Meeting Barbara was the best thing that had happened to her in a long time. Maybe it's time I took my new knowledge out for a test drive, she thought. Maybe it's time I had the real thing, with an older man as Barbara had suggested. She looked down at her lithe, soapy body and smiled. A man over 40 would love to get his hands on this, she thought - his mouth and cock too.

--

Cristi finished her Wednesday night shift and changed clothes, then headed to the adult store. She arrived a little before 10 and waited for Barbara in the parking lot. Barbara pulled in a few minutes later, and parked three stalls down. Cristi could see that she was on the phone. Cristi got out of the car and met Barbara as she was getting out of hers. "Hi sweetie," Barbara said, giving her a hug. "Well? What did you think?"

"I had no idea that it would feel like that. I have to admit, I was turned off at the thought of it, but, Barbara, oh my god."

"Did you like it?"

"Yes. Very, very much."

"I'm glad." Barbara lowered her voice and leaned close to her. "Did you pretend I was there, putting it into you?"

"Yes," Cristi whispered.

"Good," Barbara replied, and gave her a light kiss on the cheek.

"Should we go inside?" Cristi asked.

"Actually, I could use a drink. It's been a rough day. Would you like to come with me?"

"Sure!" Cristi said. "Let's get one of those streetcars again."

Barbara laughed. "It's called a Sidecar. Let's go have a few."

They sat at the same table, near the back of the room. "So, have you learned anything over the past two weeks, Cristi?" Barbara asked.

"A lot," she replied. "I can come whenever I want now," she said proudly. "I think I've learned what pleases me. I didn't really know before."

"What else do you want to learn, Cristi?"

"I'd like to learn how to please a man. Not a boy - a man."

"And how are you going to learn that?"

"I need to find an older guy," she replied. "Like that one over there," she said, looking towards a handsome middle-aged man at the bar. "He'd do."

"Not so fast, tiger," Barbara said, laughing. "What are you going to do, just walk up and tell him you'd like to fuck him?"

"Well, no. I could just go hit on him and see what happens."

"And then what? What if he's married, or worse?"

"I hadn't thought about that," Cristi said, looking at the man.

"Sweetie, men are different than us. They don't have the same, well, sensibility as we do."

"I don't understand."

"They think with their cocks."

"I thought you said older men were nice?" Cristi asked, puzzled.

"Many of them are, yes. But even the nice ones have one goal in mind: to get into your panties. The romance is just a means to that end. The not-so-nice ones, well, they're not so nice about it. You have to take the time to see where a man falls on that spectrum."

"That sounds like a lot of work."

"It is, and there are no guarantees. You must be very, very careful Cristi. Don't put yourself in a dangerous situation."

"How the hell am I supposed to find out what it's like to fuck an older guy? I don't want to wait!"

Barbara thought for a moment. "There may be a way, but... Hell, never mind, it won't work."

"No!" Cristi complained. "Tell me!"

"I don't think he'd go for it."

"Who?" Cristi asked. "Who wouldn't go for it?"

Barbara looked away. "My husband. He'd do anything for me, but this is a lot to ask."

"You'd do that for me? You'd let me fuck your husband? That's so sweet!"

"Like I said, I don't think he'll go for it. I mean, I could ask."

"Would you? It would mean so much to me."

"You have to understand, I would need to be there," Barbara said, serious.

"That would be nice," Cristi said, taking her hand.

"I'm going to call him. Let's see what he says."

"You mean tonight? That would be awesome!" Cristi exclaimed.

"I'll be right back."

Barbara stepped outside and called her husband. "Hi. I'm bringing her home, tonight."

"Already?" Troy asked. "You closed this one fast. Nice work, babe!"

"You're welcome," Barbara said sweetly.

"What do I do when she gets here?" Troy asked.

"You resist a bit, then act like you're doing me a favor by agreeing to fuck her."

"I'll fuck her, if I must," Troy laughed.

"You better not blow it, mister!" Barbara warned. "I worked hard on this! I even got her to do anal."

"Really?" Troy said. "Wow. This one's special."

"Wait 'til you see her. We'll be there in a half hour," Barbara said, and started to hang up. "Wait, Troy?"

"Yeah?"

"Get Tiffany ready."

"Are you sure? This soon?"

"Yes. Tonight," Barbara said, ending the call.

Barbara went back inside and sat down. "I told him I'm bringing home a friend. I didn't tell him about our plan."

"Ok, what should I say when we get there?"

"Let me do the talking."

"Ok"

"Are you ready?" Barbara asked as she paid the check.

"Yes. Do you live far? I should stop for gas."

"There's no need," Barbara said. "We can take my car and pick yours up later."

They got in the Lexus and pulled out of the lot.

--

"What's your husband's name?" Cristi asked as they drove.

"Troy. His name's Troy."

"What's he like? Is he nice?"

"He's wonderful," Barbara said with a smile. "He's smart, funny, romantic... I couldn't ask for more."

"What you're doing for me is so sweet, Barbara. You're such a good friend," Cristi said, squeezing Barbara's leg.

"It's my pleasure, really," Barbara replied, smiling back at her.

Barbara and Troy lived in a large house at the end of a cul-de-sac, in a quiet neighborhood outside of town. Cristi marveled at the sprawling home as they pulled into the driveway. "This is beautiful, Barbara," she said as they stepped out of the car.

"Remember, let me do the talking," Barbara said as they walked to the front door.

"Hi babe!" she called as they entered the house. "I'm home!"

Troy walked into the living room. Barbara said, "Babe, this is the friend I told you about. Cristi, this is my husband, Troy."

"Nice to meet you, Troy," Cristi said, extending her hand.

"Why, nice to meet you too Cristi. Please, sit down. Would you like something to drink?"

Cristi looked at Troy. He was tall, probably 6'2", and had light brown hair, graying at the temples. His bright blue eyes sparkled as he smiled at her. He seemed pretty fit, she thought. He obviously takes care of himself. He's actually quite attractive, for an older guy. Cristi briefly imagined him on top of her, thrusting, with Barbara standing by, watching them fuck.

"Sure, whatever you two are having would be fine, thank you."

Troy went to the kitchen to fix a few drinks. Barbara looked at Cristi and said, "So, what do you think?"

"He's very handsome. You're a lucky woman."

Troy returned with three brown cocktails, handing one each to the girls. Christi nervously at sipped hers.

"What do you do, Cristi?" Troy asked.

"I go to art school part-time, and work at Chili's," she replied. "What do you do?"

"I work in finance. Very boring stuff, but it pays the bills."

"It looks like you both have done very well," Cristi remarked, looking around the room.

Ten seconds of uncomfortable silence later, Barbara said, "Babe, Cristi has a bit of a, well, a problem, and could use our help."

"Well, we'll certainly do what we can. I think it's important to support our community's youth. What can we do for you, Cristi?"

Cristi opened her mouth to speak, but Barbara cut her off, placing her hand in her lap and giving her knee a gentle squeeze.

"Honey, I have to tell you, it's a very special problem, and it's going to take a bit of sacrifice from both of us."

"Do you need money, Cristi?" Troy asked.

"No. I mean, I'm broke, but I wouldn't ask for money," Cristi replied.

"Are you in some kind of trouble? Do you need legal assistance? Barb and I know a very good attorney, and we could help with the fees."

"No..."

"Troy, Cristi needs our help with something very personal. Now, I'm going to ask you to do something for me."

"Anything for you, my love."

"I've been helping Cristi learn about herself," she said, looking at her and smiling. "But I've taken her as far as I can. She needs your expertise now."

"I'm still not clear on what you're asking, Barbara," Troy said, his voice now serious. "Just say what it is you want from me."

"I want you to sleep with her."

Cristi looked at him sheepishly.

After a few seconds of silence, Troy replied. "Well, that certainly is a very unusual request, isn't it?", doing his best to look nervous.

"Honey, you'd have nothing to worry about. I'd be there the whole time. Think of it as a medical procedure. Of course, I'd want you to put your best effort into it."

"I don't know Cristi," he said, turning to her. "I mean, we hardly know you."

"I've never been in any trouble, Troy. I'm a good person. My boyfriends have all been young, and didn't know what they were doing. I just need to know what it's like to be with an older man."

Troy looked back at Barbara. "I'll do this, because I love you." He turned to Cristi. "You must never tell anyone about this. Do you understand?"

"I won't say a word. I promise."

"Troy's right sweetie," Barbara said. "You must never tell anyone."

"I swear, I won't tell anyone," she replied, solemnly.

"Well then," Troy said. "We might as well get this over with."

"Come with me," Barbara said to her. She took her hand and led her to the master bedroom.

Cristi could hardly believe it. It looked like she was going to fulfill her fantasies of being with Barbara and fucking an older man, together, at one time.

In the bedroom, Barbara told her, "Now, you must remember that he is going to be fucking you much longer than what you're used to, and he may do things to you that will make you feel good, but things that you haven't done before. I want you to tell us right away if you're uncomfortable with anything, ok?"

"I will, Barbara. Are you sure you'll be ok watching me with your husband?"

"I'll be fine, sweetie." she replied, pushing Cristi's hair behind her ear, then said, "You never know. I may decide to help him a bit."

Cristi flushed, and came to the realization that she was about to fuck them both at one time - man and woman, husband and wife. She became extremely aroused, and felt her pussy begin to drip in anticipation. She almost leaned in to kiss Barbara, but decided against it.

Troy called from outside, "Can I come in?"

"Yes, honey. We're just having a little girl chat."

Troy entered the bedroom, looking serious. He walked up to the two women. "Cristi, are you sure this is something you want to do?" he asked.

Cristi looked at Barbara, then back to Troy. "Yes," she said. "I, I want to."

Barbara replied, "Are you absolutely certain, sweetie?"

"Yes," Cristi whispered. "I'm sure."

Troy ran the palm of his hand down Cristi's cheek, and looked her up and down. "So sweet," he said, and began unbuttoning her shirt. Barbara stepped behind Cristi, reached around her waist, and unbuttoned her jeans, then slowly unzipped them. Troy pulled her shirt over her shoulders while Barbara slid her jeans over her hips. Barbara unfastened Cristi's bra. Her ripe breasts bobbed as Barbara took it off. Troy leaned forward, and kissed between them, then lightly down her taut abdomen to her stomach. He hooked his fingers in the waist of her panties, then slid them down to her knees. She gently stepped out of them.

Cristi was now standing naked before two relative strangers, and instinctively moved her hands to cover herself. Troy looked at her hungrily, then began unbuttoning his shirt. Cristi could hear Barbara undressing behind her. Troy took off his pants and Cristi could see that he was aroused, his manhood tenting through his briefs. He stepped out of his underwear. Troy's cock was fully erect. Cristi stared at it. It was shorter than Brad's, she thought, but much thicker. She felt her pussy moisten further, and suddenly had the urge to take him in her mouth. She decided to wait for an invitation.