Training

Ashley had talked Sharon into spending the night with her on the same night that they had talked to Zack about the possibility of adding Alice to their relationship. She had two reasons for doing that. The first was to make sure that Sharon didn’t have to deal with her mother tonight. The second was so that they could get closer and hopefully make their relationship with Zack and themselves work even better. Part of doing that was to get Sharon to help her with getting ready for Zack.

“So, let me get this straight. All I have to do is help you get ready for Zack and anal?” Sharon asked.

“Yep. I think this could be a good way for you to get used to doing things with me, without having to kiss or even touch me all that much. I mean you touch my ass all the time when you give it a slap at practice.” Ashley said.

“That’s a little bit different though, don’t you think. I don’t make constant contact then. It is a quick smack.” Sharon said.

“You don’t have to do this if you don’t want to. I am fine with that.” Ashley said.

“No, I need to do this. It will help with things in the long run. You are going to have to lube your ass though. That is not something I am willing to do.” Sharon said.

“I can do that.” Ashley said as she pulled down her short shorts and got into a doggy style position.

She got the bottle of lube that she bought when she bought all of her toys and spread a lot of it over her asshole and even pushed her finger inside a little bit so that she would have some inside of her as well. Ashley then passed the lube to Sharon who had picked up the smallest buttplug that Ashley had bought and started to lube it up. Once she was done, she turned to Ashley with a bit of nervousness. She would have never expected to be in this position, but for things to work out this was something she needed to do.

“Are you ready? I will go slow.” Sharon said and Ashley turned her head to look at her friend and nodded with a smile.

Sharon put her hand on one of Ashley’s buttcheeks so that she could spread them out a bit and then put the tip of the toy against Ashley’s tight hole. She stopped again, giving her friend the chance to change her mind. Ashley said nothing, so Sharon took that as her cue to begin. She pushed to buttplug against the blonde’s asshole and it slowly but surely started to enter the tight hole.

Ashley gasped at the new sensation. It hurt a bit, but going at the slow speed helped out a lot. Sharon was slowly pushing more and more of the plug into Ashley’s tight hole. Soon enough the whole thing was inside of the blonde. She stopped to let Ashley get used to the new sensation of having something put into her ass.

Sharon waited for Ashley’s cue to start things up again. Ashley finally looked over her shoulder again and gave a short nod. Sharon then started to pull the toy out of her friend. With only a little bit of the toy still in her friend, Sharon pushed it back forward so that the toy was now fully embedded in the blonde again. Frome here she kept moving the toy in and out slowly.

Surprisingly, Ashley was starting to enjoy it the more Sharon moved the toy in and out of her ass. She was even starting to moan in pleasure a little bit. It was a weird sensation. It hurt a bit, but it also felt good at the same time. It was a very intense feeling.

“How are you doing?” Sharon asked.

“This is really intense. I don’t know how to explain it other than the fact that it hurts a little bit but also feels good at the same time.” Ashley said as she continued to moan.

Sharon kept doing what she was doing for the time being. She didn’t know what to think about this, but she wanted to do this for Ashley. It would make their relationship tighter after all.

“Pick up the speed a little bit.” Ashley said and Sharon did as she said.

As Sharon picked up the pace, Ashley started feeling even better. She was definitely starting to moan more now that she had been when Sharon was going slow. It wasn’t hurting matters that Ashley was now a bit looser now due to the plug as well.

“Oh my God! This actually is feeling pretty good!” Ashley moaned.

“I’ll take your word for it.” Sharon said, knowing that this would not be happening to her for a long time to come, if ever.

“Let’s try a size up.” Ashley said as she looked back at the redhead, who nodded and pulled out the plug completely.

Sharon got the lube and lubed up the next size up and did the same as she did with the last toy. She started off slow and then sped up when Ashley said that she was comfortable. Sharon couldn’t believe how much Ashley seemed to be enjoying this. It just didn’t seem like it would be a pleasurable experience.

Ashley was loving this now. It was getting close to time to go to the biggest plug she had bought in the sex story. She didn’t know if she could take it, but she was sure as hell going to try.

“Let's try the last one. I think I can take it.” Ashley said.

“I don’t know. That thing is really big.” Sharon said as she looked at the last of the buttplugs.

“It’s worth a try.” Ashley said as she looked over her shoulder to her friend and shrugged.

“If that is what you want.” Sharon said as she pulled out the plug she was currently using and got the third one ready.

Once the last plug was ready, Sharon put it to her friend’s asshole and started to push gently as this was a big size for such a small girl to take. It was harder to get it inside, that was for sure. It was taking time, but slowly it was making its way inside Ashley's tight hole.

“Oh my God! I think it might go in!” Ashley moaned from the pressure that was being put on her asshole.

“I think you are right.” Sharon said as the last little bit finally made it into Ashley.

Sharon gave Ashley a chance to get used to this size that was inside of her. This would be the hardest on the blonde so far. Ashley finally gave Sharon a nod and the redhead started to slowly move the plug in and out of the blonde.

There was a slight grimace on Ashley’s face right now, so Sharon started to move the toy even slower than she already was.

“Do you want to stop?” Sharon asked.

“No, keep going. It is getting better.” Ashley said, so Sharon kept going.

Sharon kept doing what she was doing for the time being and she could tell that the plug was going in easier now. Things started to move a bit faster once Ashley started to thrust backward into the plug. Sharon took that as the blonde wanting it a bit faster, so she sped up the thrusts a bit.

“This is getting a lot better. Try to go a bit faster.” Ashley said and Sharon did just that as she sped up a bit more.

Ashley was starting to moan more in pleasure now. Sharon kept pushing the toy in and out of her friend at a pretty good pace now. Ashley then had the idea to start rubbing her pussy now that she had the biggest of the toys inside of her. Surprisingly, it didn’t take long for her to explode from the pleasure that she was feeling in both her ass and pussy.

“Oh my God! I’m cumming!” Ashley moaned out as she collapsed on the bed.

“You actually came from anal?” Sharon asked, amazed.

“Yeah. I am just as surprised as you are.” Ashley said from her position on the bed.

“Well, I guess that means we are done. We have used all of your toys.” Sharon said, happy for this to be over.

“There is one more thing that I want to try. I found this in Hannah's room the other day. I figured it could help out.” Ashley said as she went over to her drawer and pulled out a huge dildo that was attached to a harness.

“What the hell do you want me to do with that?” Sharon said.

“I want you to put it on and fuck my ass.” Ashley said.

“That wasn’t part of the deal.” Sharon said.

“Pleaseeee. Pretty pleaseee.” Ashley said with her best puppy eyes look.

“Fuck. How can anyone turn down that cute look? Damn you.” Sharon said as she took the strapon and put it on, on top of her clothes.

Ashley lubed up her asshole as well as she could and Sharon took the bottle and did the same with the strapon. As she was looking at the strapon as she was lining it up with Ashley’s ass, she realized that it was pretty much the size of Zack in every way. She could see why Ashley would want this now. Didn’t mean that she had to like it though.

“You ready?” Sharon asked and Ashley nodded.

It was a tight fit and it took a lot for Sharon to finally get the toy inside of Ashley. Once she finally did, she stopped and let the blonde get her bearings. Ashley finally started to move her hips, so Sharon started to withdraw the toy and then push it back in. It was slow work at first, but Sharon felt Ashley get looser, which meant that Sharon could speed up a bit. Ashley was now rubbing her clit too, which was pushing her closer and closer to another orgasm.

Sharon could tell what was happening and was happy that she wouldn’t have to do this much longer tonight. She knew that there would probably be more training sessions in the future, but at least it would be over for now. Sharon was brought out of her thoughts as she heard Ashley get a bit louder as she came.

“Oh shit! I’m cumming!” Ashley moaned.

Sharon pulled out of Ashley and went to stand up so she could take the strapon off. She looked over at her friend who was laying on her stomach trying to catch her breath.

“I can’t believe you actually liked that.” Sharon said.

“It was great. Don’t knock it until you try it.” Ashley said.

“I don’t know if I want to try it.” Sharon said.

“That’s fine. It isn’t for everyone.” Ashley said and Sharon nodded.

“You know. I think I am going to sleep well tonight.” Ashley said as she rolled over on her back.

“I think I am going to have nightmares.” Sharon said.

“Oh, come on, Sharon. It wasn’t that bad.” Ashley said.

“Speak for yourself.” Sharon said.

“Fine. Thanks for your help though. Let’s get some sleep.” Ashley said and Sharon nodded as She got into her sleeping bag on the floor and Ashley got under her sheets on the bed.

“Well, at least we might be getting closer now.” Sharon thought to herself as she could tell that Ashley was already sleeping because of the way she was breathing. Sharon wasn’t far behind her though.