Amy's Anal Adventure with Alice Ch. 01

*Author's note: I know this is long, but I like character development. I hope you will too.

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Amy and Todd had been together since Freshman year in college, now, two years later, Amy was pretty sure they'd get married once they were done with school. They were still very much in love two years after their romance began. Amy loved Todd and he loved her right back. They had similar interests, and overall just loved being in each other's company.

Amy and Todd were studying in his room, on his bed, but Amy couldn't concentrate, she knew Todd's birthday was in a week and she couldn't think of what to get for him. Every time she asked he gave the same answer ' you don't need to get me a gift babe.' Such a guy thing to say, but it was probably true, if Todd wanted something, which was rare, he'd ask his parents and poof, there it would appear. Todd's family was well funded, he was doing well studying pre-med, so his parents were proud of him. They didn't want him wanting anything so they took care of any need he had.

Amy came from a household were money was always tight. Her father worked two jobs just to pay the bills, put food on the table for Amy, her sister, and her mother. Luckily, Amy was able to get enough scholarships and student loans to cover the cost of college. She worked as a waitress to pay for other expenses like her books and clothes, etc. She knew she didn't have much money to spend on Todd, but it was his twenty-first birthday for God's sake, she had to give him something he wanted. Amy wasn't the best student, she did her best for most of her academic career to achieve B's and C's, that is, until she met Todd. For some unknown reason, he worked with her for about an hour and he understood the way she learned. He was able to teach her how to study for tests so that she was no longer nervous about them, instead confident. He taught her how to organize papers and writing prompts so that she would do well. He brought her from an average student, to the top of her Journalism class.

Finally, she had had enough of her wandering thoughts. She sighed and as soon as the noise escaped her lips, Todd looked up from his organic chemistry reading.

She looked at him and said "Baby, what do you want for your birthday? I know It's silly, but until I have it sorted out in my head I cannot concentrate."

He grinned at her and looked back down "Aim, I told you before, you don't need to give me anything, I'm happy with you and that's enough for me." Then, he looked back down at his papers and continued reading.

"Ugh," she groaned. "you're so frustrating sometimes, you know that? There must be something I can give you, even if it's small, anything, please, you've done so much for me."

Todd grinned, "Anything? Really? Hmmmm, well, there is one thing."

Amy looked at him a bit puzzled and then asked the obvious question, "Ok, what is it?"

Todd didn't look up at her, but she could see his 'evil grin' emerge on his face 'Well, I've always wanted to take your ass."

Amy wasn't drinking anything and still thought she might choke. She did know that Todd had always wanted to try to take her anal virginity. He had stuck his finger in her butt while they were having sex before, and she liked the feeling of that. So much in fact that if she knew they were going to have sex she'd clean up really well with a finger in the shower sliding up and down in her ass to make sure she was nice and clean for his finger or his thumb, whichever he used at the time. She actually got really horny a few times that she was cleaning up in the shower and slid her finger up there, she'd start rubbing her clit and nearly came right there in the ladies shower in her dorm. There was once when he tried to put two fingers, but it hurt so she asked him to go down to one. Maybe it was because she wasn't quite ready yet, she wasn't sure.

Amy saw Todd during orientation day, literally her first day at school. She didn't expect to meet the person she figured she'd marry on her first day. He wasn't the most athletic guy, he had a tummy, but the way he looked and his kind smile, she couldn't stop looking. After she picked up her books at the bookstore, she was walking to her dorm, not paying attention, she walked right into him as he was making his way into the bookstore, funny enough he was actually trying to make sure she didn't hit him, so she wouldn't be hurt, but he miscalculated her step. He chuckled when she turned beat red and her books flew in every direction. He helped her up and helped her pick up the books and started talking to her, so much so, that he walked her back to her dorm and had to walk all the way back to the bookstore, he didn't mind because he knew right there he loved her.

Amy was small, she was only 5 foot 4 inches compared to Todd's 6 feet. Her skin was a pale white and she had chestnut brown hair and green eyes. Todd, who stood above her, even in heels, had dirty blonde hair and blue eyes, she always thought he had the kindest eyes. They loved old movies, they loved to play Xbox together, and she swore he let her kill him in Call of Duty and Halo multiplayer. She was pretty sure he loved the way she stuck her tongue out between her teeth and twisted the controller in the direction she wanted her player to move, and she was right, he loved it all.

Amy knew Todd didn't want to hurt her, and he could see her wrestling with his revelation of what he wanted for his birthday. "Aims, forget it, I don't want you worrying about anything, it's fine. I've got everything I need right here. Ok? Seriously, let's not make a thing of this."

She continued to look as though she was thinking it through and working out what her response would be. She finally looked up and said "umm, I don't know if I can... I mean I could try, I don't know babe, I mean, um, errr, I don't know if it'll hurt too much, maybe, ok, maybe."

Todd got up, went to her and held her and said "Forget I said anything, let's just have a good day together and we'll get ice cream or something."

The funny thing, she thought, was that he meant it too. He didn't want her to worry, and he loved ice cream, so he actually would have been fine doing just that. Amy couldn't stop thinking about it, she loved giving herself to him in every way she could, this was just one thing that made her nervous, but she had a plan. After they finished studying, they made out for a bit and she and Todd walked back to her room. Todd left her once she was safely inside and went back to get some sleep, Amy flopped down onto her bed face first. She wanted to cry, she loved Todd and wanted to give him this. She sobbed and hugged her pillow, she waited for Alice, her roommate, to get back to the room.

Amy had started to drift off to sleep when she heard the door open and close and her roommate, Alice dropped onto her own bed. Alice looked over and said "what's new with you Donna Reed?", her nickname for Amy as she thought Amy had the perfect life with the perfect boyfriend. Where Amy's family worked hard and loved she and Todd to pieces, Alice was a disappointment to her family. She wasn't following in the family tradition of becoming a lawyer, she wanted to work on TV as a news writer. She had tattoos and a punkish look of which her family didn't approve, and, worst of all, according to her family, she was bisexual. Her very conservative family could get past the tattoos, the clothes that they figured was a phase, but the fact that she loved women sometimes more than men, that they could not look past and so she rebelled against the family Attorney business since she knew she'd never be truly welcome. She'd never see her name up on the wall. Most of all, she never wanted to be with people who didn't accept her for who she is.

When Amy looked up Alice could see that she was upset, she was a bit taken a back but offered, 'hey Amy, I'm sorry, you know how I joke around, I'm sorry, what's wrong?" She looked at her roommate who she really liked as a sister who wasn't saying a word. She had that look of 'I can't say it' on her face.

"Is it Todd?" Alice asked, figuring that this is the most upset she'd seen her roommate of two years ever, it must be serious.

Amy nodded and held her hands over her face and whimpered.

"Did you guys break up?" Alice asked, hopeful that wasn't the case, but it was worth a shot.

"No, it's Todd's birthday next week" Amy sobbed into her palms

"Err, ok, and that's bad?" Alice now had no clue what was wrong until she remembered how obsessive her roommate is about finding 'the perfect gift' and for Todd, that could be a tough call, the guy had everything.

"No, it's what he wants for his birthday." again Amy sobbed. Alice could see her mascara running down her face.

Alice thought 'he can't want something that she can't afford, he'd never do that to her, he knows her family's financial situation.'

"Amy, what is it that he's asking for that's making you this upset?" Alice asked her.

"He wants my anal cherry, he said he was kidding and he'd be fine with ice cream instead, but he's never asked for anything from me. How can I deny him this?!" She muttered as her hands finally dropped from her face.

It took Alice a minute to decipher exactly what Amy said through the hands covering her face, hyperventilating, and sobbing, but in the end she was pretty sure she understood.

"Oh, is that all? I thought you guys broke up or had a huge fight, geez Aim, no one died, what's the big deal?" Alice asked.

"The big deal? The big deal?!" Amy cried out in shock. "I've never done that before! I don't really want to, I'm afraid it'll hurt" Amy started to cry again.

"Hey, hey now, it's not that bad, I can tell you how to get warmed up, so you'll be fine. Relax, I love anal now, there are days I prefer it." Alice tried to comfort her.

"Really? Amy stopped crying.

"Sure, I'll tell you how to get comfortable with it, and you'll be fine." Alice assured her again.

"Could, well, could you, um, you know, help me? Like, do it with me?" Amy asked.

Alice knew Amy was straight. Sure, they'd shared a kiss, a fondled breast and butt cheek after a drink or two, but this was very different.

"Amy, you love Todd and..." Alice began but was cut off by Amy.

"I do, I love him with every part of me, but I've always loved you Alice. You've always been here for me whenever I've needed you. I've been curious about doing more with girls for a long time. Whenever you and I would start cuddling or touching each other, you'd break it off. I figured I was doing something wrong, or maybe it's because I like guys more than girls." Amy confessed to her roommate.

"Oh wow, this is a lot. No, I didn't back away because you were doing something wrong. I backed away so that I wouldn't push you. I knew you loved Todd, and well, I didn't want to jeopardize that. Honestly, I didn't trust myself not to want more. I didn't think we'd have a relationship like you and Todd do, but I would have loved to do more with you." Alice spoke softly to Amy, making her own confession of sorts.

Then, she continued "Amy, if you like, I'll help you with this. By the time his birthday comes around, you'll be an anal pro. There may be times that you'll want an anal orgasm instead."

Amy didn't see how that could possibly happen, but she trusted Alice just as much as she trusted Todd. They'd never hurt her, lied to her, or tried to deceive her. She smiled and calmed down knowing that her friend would help her.

"How do we start? When can we start?" Amy asked inquisitively.

"We can start tonight if you like." Alice smiled. "We'll start slow, and take it one step at a time. You have to trust me, I promise not to move any faster than what you say you can handle. Deal?" She asked.

"Deal. Teach me, teacher. What's my first lesson?" Amy sat up on her bed and perked up. Alice swore she saw Amy's breasts bounce and nipples harden through her shirt and bra when she sat up. Alice melted a bit knowing that she'd finally be able to touch Amy in the way she'd always wanted to, but didn't want to freak her out. Now, she salivate with the chance to touch Amy in the most intimate of places.

"OK, then, get up." Alice commanded.

"Whe..where are we going?" Amy asked curiously.

"To get cleaned up." Alice said grabbing towels, face cloths, soap, and shampoo.

Amy and Alice both undressed and slipped into bathrobes and made their way down the hall to the shower. There were shower stalls on both sides of the room and the had a door and curtain for privacy. Inside there was a bench for placing personal items as well as towels and hooks for clothes. Amy started into the first stall on the left. As she did, Alice was right behind her and looked surprised as Amy was closing the door.

"Are you coming in my shower with me?" Amy asked with a puzzled, almost innocent look on her face.

"With all that we're about to do, and you're going to get modest with the shower." Alice grinned.

"Ahh, good point." Amy agreed and stepped aside to allow Alice entry into her shower stall.

They both smiled at one another as they put their personal items down and started to take off their robes. Amy notice that there was an odd object mixed in with Alice's things.

"What is that?" Amy asked.

"The big thing with anal is being clean and being relaxed. This little ball enema gets you clean on the inside, so there are no worries. Don't worry, it won't hurt or anything, promise." Alice smiled with her explanation looking over at Amy's body as her robe slipped from her shoulders revealing her pale skin and perky breasts which were just the right B cup size for Alice.

She loved how the curve of Amy's breast almost made that tear drop shape from the profile, with gorgeous nipples protruding from the tips. Alice eyed her up and down with out making it seem too obvious. Amy was smaller than she, with small features, her legs were cleanly shaven and shapely, Alice loved the way her legs stopped and the curve of her ass began, it just bumped out, curved around and connected with the small of her back in an arch. Her hair was down and spilled from her neck down to her shoulders to almost the middle of her back. Alice wanted to throw herself at Amy, but thought better of that idea. She removed her own robe, she wasn't as pale as Amy, her breasts were larger and her hair was darker, and she was an inch or two taller, but, like Amy, she was clean shaven from the waist down. Alice picked up everything and headed to the shower, turning it on so that the water would be warm for her friend.

"Are you ready Amy?" Alice's voice changed to a very sultry and calm voice, one that Amy wasn't sure she'd ever heard before. She was drawn to her roommate's call, like a ship to the Sirens. She nodded slightly and padded over to the shower where her friend was waiting for her with her hand in the water to ensure that the temperature was just right. Amy's cheeks were flushed, a little excited, a little nervous, and a little self-conscious of being so naked and exposed in front of who she would consider to be her best friend at school, but she continued to walk forward until the warm water cascaded down her back, dampening her hair. Alice loved the way the water glistened off of her skin and she was thankful that they were the only two people in the shower room. Before Alice ducked into the water herself she looked at the lock on the stall door, just to make sure it was closed completely.

Alice entered the water with Amy and the skin of their arms, their legs, and their breasts brushed against one another. Both girls quivered at the electric feeling that coursed through their bodies as they touched. Alice made the first move, her hands raised up and rubbed Amy's arms as she leaned forward and gently kissed Amy's lips.

"Don't be nervous, ok? I think we'll both enjoy this and we know where we stand, everything is out there, no surprises. Ok?" Alice comforted her roommate.

Amy nodded in response and licked her lips, and pushed herself forward kissing her friend on the lips hard and opening her mouth, her tongue pushed out and connected with Alice's. Alice pulled her close so their bodies pressed together, and Amy melted into her arms as they kissed. Alice let her hands fall down Amy's back and rest on the cheeks of her bottom, she lifted the fleshy globes and separated them, pulling Amy's ass apart, the warm water streaming down between her cheeks, washing over Amy's tight hole and teasing the very bottom of her pussy. Amy gasped into Alice's mouth and moaned a little as Alice's hands massaged her cheeks. Realizing that she too could touch, Amy rubbed her hands up and down Alice's back, each time exploring further down Alice's body. Alice moaned and Amy could feel her mouth turn up into a smile as they continued to kiss, their tongue's dancing with one another. Amy couldn't believe how nice Alice's mouth tasted.

Alice reached down, breaking their kiss for a moment, grabbing the soap and squeezing it right between their bodies, then giving her body a little shake against Amy, spreading the soap around between them, making their bodies even more slippery. Alice put more soap into her hand and rubbed it down Amy's back and between her cheeks, grazing ever so lightly over the tight opening to her bottom. Amy gasped and then relaxed remembering that she needs to relax. Alice rubbed her hands up and down between Amy's cheeks, getting them very sudsy. Amy pushed her butt out into Alice's hands. Alice, feeling Amy push into her hands smiled and ran her finger up and down Amy's ass, paying special attention to slow down over the entrance to her rear. Then, her hands wandered slightly down to the lips of Amy's pussy. As she started to touch and rub, Amy shot up.

"Wait, am I cheating on Todd? I love him, I don't want to cheat on him." Amy looked a bit worried again.

Alice went back to stroking Amy's back "Hey, you're not doing this against Todd, you're doing this for Todd. We're doing this so that you'll have a more enjoyable experience with him and so you'll want to have anal sex again. Instead, we could do nothing, you'd be nervous and I would hate for your hand for him to have a negative experience an then you don't ever want to do it again.

Amy once again nodded and settled back into Alice's hands which began to rub her up and down her back again. Alice stood up and let Amy bend over more. Alice moved the shower head so that Amy wouldn't be doused with water. She moved behind Amy and bent down so that she was eye level with Amy's pussy and ass, all laid out in front of her. Finally, after more than a year, she could finally touch Amy like she really wanted to. In the back of her mind Alice did wonder what would happen when this was done, once Todd was able to take Amy's ass and Amy liking it. Would Alice be thrown aside to find a new lover? She didn't think that either Todd or Amy would do that to her. Todd was always nice to her, and she did think he was cute, for a guy. She'd have to take a chance on this and hoped that she wouldn't feel jealous at the end.

"Alice? Am I ok back there? You're not doing anything, are you ok?" Amy asked in her self-conscious voice, and turned her head to look behind her.

Alice, emerging from her inner thoughts looked up into Amy's gorgeous pussy and her ass, which Amy had started to part with her hand, exposing her pink entrance to her bottom and the lips of her pussy just barely starting to part, revealing the dark tunnel. She smiled and met Amy's eyes.

"Oh my god Amy, you're gorgeous back here, every inch of you. I was thinking and just staring at how beautiful you are" Alice smiled back at Amy's staring eyes.

Amy looked forward again and Alice began by sliding her hand up Amy's thigh until it reached her pussy. She let her hand rub back and forth over the skin covering Amy's clit before leaning forward to taste her for the first time. Her tongue just making its way between her lips, she heard Amy gasp and moan as Alice's tongue touched her in her most intimate of places. Alice then slowly pushed her tongue into Amy, she was a bit mesmerized by how sweet her roommate tasted. She could have spent all day here, with her mouth licking and tasting her friend. She reached up and spread Amy's butt cheeks, she looked up as she licked and saw Amy's tight entrance part just slightly. She felt and heard Amy moan. Alice soaped up her hand and rubbed her thumb over Amy's butt hole, she pressed slightly, but didn't enter her. She could see Amy reaching down to grab her own breast with her hands and pinching her nipple. Alice's tongue pressed further into Amy and Amy's body began to rock backward, pressing her bottom into Alice's face. Alice loved feeling Amy's bottom press against her face, her nose pressed into her taught rear, she could breath in all of Amy's scent. Her tongue immediately, almost without her knowing, left Amy's pussy, and flicked over the tight skin of her butt hole. Amy breathed in sharply and began to moan as Alice pressed her tongue into her butt.