Amy's Anal Adventure with Alice Ch. 02

She and Alice continued with the remainder of their classes for the day. They ate supper together, though Amy barely touched anything, she was far too nervous. They made their way back to their room and started prepping for the night. They showered together and used the water enemas to clean out and clean up. Amy and Alice both felt an attraction to each other, and it was difficult to restrain themselves from having another session of sex while in the shower together. Amy's stomach was still in knots over Todd. She really hoped that they would make it through the night together, yet something was bugging her.

She had conflicting thoughts. She loved Todd, wanted their relationship to last. Yet, she didn't want to lose this new relationship she had with Alice. She felt like she loved them both, and she wanted to keep them both in her life.

As they were drying off and gathering their things Alice and Amy wrapped themselves in towels and walked back to their room. As they entered, they put things away and started dressing for the night. Amy wondered if Alice would be interested in keeping their relationship going.

"Ali, can I ask you something?" Amy started off.

"Sure babe, what's on your mind?" Alice asked, getting herself dressed, she was wanting to wear clothes that were pretty. She mostly had jeans and t-shirts because it pissed her family off to see her in what they called 'guys wear'. Now, she was interested in looking nice for Amy and for Todd.

"Would you, well, umm, be interested in being with me and Todd together, more than just tonight? Amy asked in a squeaky high voice.

Alice laughed and was going to reply with a resounding "No." Then, she stopped right before the no fell out of her mouth and really thought about it. She was falling for Amy, there wasn't any doubt. Though, she'd never shared someone before. She wasn't sure if she could do that. Todd, not the ugliest guy around by any means, was nice and warm and she could see herself with them. She thought that she would be sort of the third wheel in the relationship. She didn't like feeling that way, but she liked the thought of being able to continue fucking Amy. She even liked the thought of doing things to Amy while Todd was fucking her. Even still the thought of Todd fucking her wasn't totally unpleasant. She decided to play it safe, at least for now.

"Let's see how tonight goes. Then, we can figure out the details. Sound ok?" she finally replied.

Amy nodded and continued to dress. She put on her silky panties, put on white nylons and a pretty skirt that wasn't too short, but that her parents probably wouldn't have like the hemline. She was ready, she looked at her clock, ten minutes to seven. She knew it would probably be the longest ten minutes of her life.

"It's going to be ok." Alice assured her. "Don't be surprised if he freaks at first, just let him settle into it and he'll calm down" she continued.

Finally, the moment arrived, a few minutes before seven, there was a knock on the door. Amy froze and Alice could visually see that she wasn't motioning to get up. So, she decided to answer the door. Todd was standing there, handsome as ever. Freshly showered and shaved, Alice could smell his soap and aftershave.

"Hey Alice." Todd said.

"Come on in" Alice replied with a bit of a smile.

Amy did her best to maintain her composure when Todd walked through the door. Todd looked at her and he could tell something wasn't quite right with her. Something was up, and he walked over to Amy's bed and knelt down in front of her.

"Hey, babe, what's wrong? Are you feeling sick or something?" Todd questioned.

"No, not sick, just ... well, do you remember what you told me you wanted for your birthday?" Amy replied still trying not to get upset.

Alice walked over and sat on Amy's bed and started rubbing her back. Todd looked up at her. He'd never really seen Alice touch Amy before. He didn't mind it, but it was another thing out of place.

"I think I jokingly said something about, well, uh, anal. Why?" Todd stumbled on his words a bit because he wasn't sure how Alice felt about open discussions of sex.

Alice smiled at him to let him know that it was ok, and that they had probably discussed this a lot more than he thought.

"Well," Amy continued. "I really wanted to give it to you, but, I knew I didn't know what to do so that I wouldn't hate it. I know you like anal play and I didn't want to hate it, I didn't want to only give it to you once. Mostly, I didn't want it to hurt." she said.

"Ok?" Todd said and then added "Please tell me you didn't sleep with some guy to try it out while I was busy." he started to flush a bit and his voice rose just a tad. Todd wasn't one to get upset easily and he took a breath to calm himself.

"No, I didn't sleep with another guy." Amy answered, her voice shaking a bit. "I asked Alice to help me try it out." she managed to say.

"Alice?" Todd said and looked over at Amy's roommate.

"Yes, she wanted to make sure I was able to give you what you wanted without it hurting me, so that I'd want to do it with you more than just the once. She helped me train it so that I could take you. She'd also like to help me take you into me tonight, if you're still interested. She wants you to take her as well." Amy explained.

Todd stood; he wasn't sure what to say. In a way he felt betrayed, he could have helped Amy to like anal without just plowing his cock into her ass. He should have been here during this session they had, or was its sessions? Yet, the thought of being able to take Amy's ass without her being in pain excited him. She had done this to him, and also done it for him.

"Please baby, say something. I wasn't trying to hurt you; I wasn't trying to cheat. I just wanted to be able to give you something special for your birthday. I know how it looks, but really I just wanted to make you happy without hurting myself." Amy started to cry.

Todd hated to see her cry. On the other hand, he was angry, and he was hurt. He could have been here for their sessions together. He knew he needed to talk to David, his older brother, he was two years older than he, and a senior at a different school. He knew he couldn't do it here. He needed a walk, just to clear his head. He wasn't sure if he wanted to take them both up on their offer, or if he wanted to walk away and not look back. The thought of never seeing Amy again upset him more than he was angry. He knew he needed air and to talk to David.

"I'm going for a walk." Todd said

"Are you leaving me?" Amy squeaked out with tears in her eyes.

"No, I just need a minute to wrap my head around all of this. Ok?" he replied getting up and walking toward the door.

As he walked Todd could hear Alice consoling his girlfriend, telling her not to be upset and that it would be ok. He thought that should be him rubbing her back. He didn't want to make a bad decision. So, he left the room and closed the door. He made his way downstairs and outside into the cool night air.

He dialed his brother's number. It rang several times and went to voicemail. He texted David that he needed to talk quickly, and it was an emergency. He waited a few moments and his phone buzzed. It was David, Todd picked it up on the second buzz.

"Hey Todd, you ok? I just got to a party, I can't talk too long, it's going to get loud in here." David said.

"I'm not sure if I'm ok." Todd replied, and proceeded to tell David everything that he had learned about Amy and Alice and their exploits.

Once Todd finished, David thought for a second and asked, "do you love Amy?"

"I do." Todd replied.

"Ok, then let me see if I can get this straight. You jokingly said to your girl that you wanted anal sex for your birthday. Something she'd never done and had heard nightmares about. She, wanting to give you what you wanted without hurting herself and maybe getting a little pleasure out of it herself, asked her cute roommate to stick things in her butt to help her get ready for your dick. Then, when you get there, she feels guilty for cheating on you with said girl, but they now both want to fuck you and give you anal in a threesome, possibly to continue into a three-way relationship. Now, you feel upset, why exactly? Most guys would give their left nut to be in your position. Hell! I'd give my left nut to be in your position. If Amy's half as cute as the pictures you texted me and if the roommate isn't half bad and you're not interested just send me the address." David exclaimed.

"But she gave her anal virginity to someone else." Todd said.

"Oh, get over yourself Todd." David said. "You're the first actual guy who will penetrate her ass, does that make you feel any better? She trusted another girl who'd done what you wanted before and the girl showed her what to do with some toys. Toys that you may get to use on one of them, or even both of them. You mean to tell me that Amy hadn't used any sex toys before you had sex? Yeah, ok, maybe not with someone else, but who cares. This situation is hot as hell. Like I said, plenty of guys would kill to be where you are now. Where are you now anyway?" David replied.

"I left their dorm and I'm outside." Todd explained.

"You moron, get back in there and have the time of your life. Hopefully, they haven't changed their minds by now since you killed the mood. Honestly." David yelled.

"Thank you, David, I just needed to talk it out." Todd said as he started to walk back toward the door.

"No problem dummy. Heh... I'm off. Take pictures for me, will ya?" David chuckled.

"Goodnight, brother." Todd said and heard David say "aww, come on!" as he ended the call and hurried back up to Amy and Alice's room. He knocked on the door and Alice answered. She didn't look pleased.

Todd walked right over to Amy who was slumped on her pillow and threw his arms around her. He pulled her back up to a sitting position and leaned her body against his. Alice sat down on the opposite side from Todd, next to Amy and Todd moved his arm so that Alice's body touched Amy's. He rested his hand in the middle of Alice's back and she made no move to remove it.

"I'm sorry." Amy sniffled.

"No, I'm sorry." Todd said and Amy looked up at him.

"I just needed to wrap my head around everything you said. I needed some air." Todd explained.

"You called your brother, didn't you?" Amy asked.

"Yeah, I did." Todd said.

"What did he say?" Amy asked.

"He called me a moron for not being with two hot girls who have been practicing anal sex to get ready for me to take them." Todd said with a smile.

"I like the way your brother thinks." Alice said. She still wasn't sold on being fucked by Todd, but if it meant she'd still get to do Amy, she could live with it. Heck, she might even enjoy it.

Alice looked down at Amy. "See, I told you he just needed a little time. It all worked out." she said in a soothing voice.

Amy looked up at her and leaned her body over to kiss her roommate. Alice met Amy's mouth with her own and they kissed breathing deeply as their mouths and tongues made contact.

Todd felt a little strange watching Amy kiss someone else that wasn't her family. That feeling turned into heat as he watched the two girls making out next to him. He watched Alice's hand move to fondle Amy's breast through her blouse. He didn't feel like he owned Amy or anything, but there was a certain jealousy that he felt watching his girlfriend being felt up by another person, even if it was a cute girl. He stifled the feeling and continued to watch the two girls. His jealousy started to fade when Amy reached for his leg and moved her small hand up his thigh. He could feel himself getting erect.

Todd unbuttoned his shirt and took it off. Alice started to pull Amy's blouse over her head and arms, revealing a sexy white bra underneath. Todd got up and made sure the door was locked. He wasn't entirely sure what was going to happen tonight, but he was sure that he didn't want someone accidentally walking in on them. As he returned back to Amy's bed, Amy was clawing at Alice's shirt, trying to expose as much of her flesh as she could. He was satisfied just watching the pair tearing each other's clothes off while he sat.

Eventually, Alice got up, took off her shirt and removed her pants. She wore pink panties and matching bra. Todd looked over at her and was aroused by the sight of her. She stood and inch or so taller than Amy. She had dyed her shoulder length hair pink which she had put into a ponytail. Her breasts were larger than Amy's, not that he ever complained about Amy's body, he loved her just the way she was. Where Amy was a thin build, Alice was a medium build, not overweight, just curvier. The black and grey tattoos on her upper arms and lower back, that he'd seen previously, stood out on her pale skin. The more Todd looked at Alice, the more he wanted to touch her. He loved her full lips and wanted to feel them around his cock. He knew she was more into women than men, but, he thought, he might be able to change her mind.

"You're really beautiful, Alice." Todd said and he could see her face flush instantly. With her skin color, there was no hiding her embarrassment.

Amy smiled at Todd; she liked the fact that Todd accepted Alice. She decided to get off of the bed and remove the rest of her clothing. She slid the skirt off of her hips and let it fall to the floor. She revealed her white silky panties, matching bra, and white nylons. She walked over to Alice and started to unhook her pink bra. Alice let it slip through her arms, exposing her full chest. Amy bent down and took a soft pink nipple into her mouth and sucked on it, like a baby would feed. As she did, she hooked her fingers into the sides of Alice's panties and slowly drew them down her legs. Todd watched as his girlfriend pulled Alice's panties down. Any feelings of jealousy melted away. Yeah, she'd clearly done this before, but now she was putting on a show as much for Alice as for him. He stood up and removed his clothing down to his boxers and sat back down. He continued to watch his girlfriend, who he always thought was so innocent and green to the world of sex, suckling on her roommate's breast, stripping her underwear off and watched as she removed her own bra and panties. His cock jumped to attention, tenting his boxers straight up. Once they were both naked, Amy turned her back to him and bent over at the waist showing off her parting butt cheeks and the glistening slit of her pussy. She ran a finger over both holes, paying particular attention to her ass.

Amy wanted Todd to enjoy this show, she wanted Alice to enjoy it. She felt like she was stuck between two worlds that were in the midst of colliding. She had her boyfriend's world of a relationship, and now she had her new lover's world of role play and anal sex. Amy wanted to mix those two together and make them one. She felt that suckling on Alice's breast was a good ice breaker for Todd to see. By following it up with removing Alice's underwear, she could show Todd that she wasn't a little girl, though she did enjoy playing one for Alice. She really loved that feeling of being dominated by her and hoped that, somehow, Todd could fit into that. She wasn't sure how into role play he would be, but maybe, just maybe, he'd like it. As Alice and she were both undressed, Alice moved toward her side of the room for a moment. Amy decided to take a peek into Todd's shorts.

"Well now, this looks so uncomfortable. May I take them off for you? She asked in a high sultry voice.

Todd flushed with excitement and nodded at the doe-eyed girl he now wondered where she'd come from.

Alice returned with what looked like some vibrating toys, a couple of condoms, and a bottle of lube. Todd looked at her with a curious look in his eye. He looked down and Amy had her hands hooked into his boxers and was tugging them down. He stood to make it easier for her. Once they were off, Amy pushed him onto the bed.

Alice stopped and said "One rule, nothing is off limits until someone says its off-limits. Ok?"

"Keep an open mind about all of this Todd. Also, it's been a while since I've been with a man, so if we get to doing anything, just take it easy, deal?" she continued.

"Deal." Todd said.

"Yes Mama" Amy cooed. Todd looked at her with eyes wide. This was new to him. Clearly, they had an established role play here.

"If she's Mama, who am I?" Todd asked.

"Oh, that's easy." Amy said kissing his mouth deeply and swirling her tongue around his. As she broke their kiss, she dragged her breast across his chest and put her bottom in his face. "You're Daddy." she smiled.

Todd melted and instantly pulled Amy's bottom over to his mouth and started to lick the entrance to her butt with eagerness.

Amy eep'd in response.

"That's right baby, you let Daddy lick you" Alice said taking Todd's stiff cock in her hand and stroking it slowly up and down. She heard him breath in and tense up, but then relax as she continued to stroke him. She leaned forward and kissed Amy deeply who moaned into her mouth, filled with pleasure from Todd's mouth which had moved from her ass to her pussy and back to her ass.

Amy broke from Alice's mouth "I want you to try taking him inside of you" she said.

Alice wasn't sure. She wasn't having a problem stroking Todd's cock, it felt nice and warm in her hand, unlike the cold toys she'd used over the past few years. She wasn't afraid or anything, she just didn't want to be hurt by another guy. She didn't know where this was all going. She trusted Amy, she didn't know if she could trust Todd, but after stroking him for a minute longer and watching Amy writhing on Todd's face, she decided to risk it.

Alice threw a leg over Todd and lowered her body onto his. She paused as the tip of his cock touched the lips of her pussy. She raised her hand, licked her palm and rubbed her sex. She then took hold of Todd's cock again and rubbed it against her pussy. Up and down she moved the deep red, almost purple, head of his cock. She could hear Todd moan into Amy's body. She let the head of his cock find the beginning of her tunnel and started to lower herself slowly onto his cock. Just a little at a time, then she would stretch her legs up before lowering herself down a bit more. Finally, she sat on his hips, his cock was fully inside of her. She was surprised how much more natural it felt to have a live cock inside of her instead of plastic or silicone. She leaned forward and kissed Amy again. Amy reached out and fondled her breast as Alice started to rock back and forth on Todd's cock. She started breathing heavily and making high moaning sounds into Amy's mouth as their tongues explored each other's mouths.

Amy wasn't totally sure that she'd like to watch Todd fuck another girl. It ended up turning her on more than she thought it would. She could feel her juices flowing inside of her as Todd's mouth continued its migration from her pussy to her ass and back. She enjoyed this new freedom; nothing was off limits. She felt safe with these two. Todd's tongue slithered up her bottom and she squealed with delight. As it withdrew and he started to move toward her pussy again, she knew she'd cum if she didn't actively try to stop it. Soon, it would be time for her to offer her ass to Todd for the first time.

Todd couldn't believe how he was feeling either. From feelings of anger and resentment to lust, to ecstasy. His view of Amy's bottom and pussy were turning him on so much it made it cock rock hard, almost to the point of hurting. Then, when Alice started to stroke him with her cool touch, it made him jump a bit. Whenever she took his cock into her pussy, he was actually shocked at how good it felt. He'd only been with Amy for the past couple of years, he was hoping that she wasn't jealous of his cock being inside another girl. He figured she told Alice it was ok, but he couldn't quite hear over his own moans and Amy's thighs by his ears as he continued to feast on her holes. God, she was so warm and tight. She started to move up and down on him and between that sensation plus the vision of Amy's back side in his face, he had to struggle not to cum.