Loving Lisa Bk. 01 Ch. 03: Training

As she teased herself, she remembered a conversation she had overheard between her two coworkers Shawna and Terry. Shawna was frank about her ability to, in her words, "take any cock in my ass" — something Lisa had witnessed a few hours ago. At the time of the conversation, Terry was dating a guy who had expressed some interest in her butt, and she was asking Shawna for tips. Terry had been very scared about making a mess, but Shawna said that any guy who wanted to go there should understand that a mess was a risk. That said, a good diet and making sure you had emptied your bowels a few hours before anal was all she ever did, and she was almost always clean. Terry was also understandably worried about pain, and Shawna said that plugs, lube and conditioning were the way to address that issue.

"It's like Pavlov's dog, Terry. Every time something gets near your ass, you should be rubbing your clit. While you're training, always masturbate with a plug in. That way your body starts to associate having something in your ass with an orgasm. And, baby, don't let him fuck your ass in his car or over the kitchen table, at least until you have some practice. It needs to be in a bed, so you can experiment with positions, with a towel under you to catch the lube, because too much lube is probably just enough. The other thing you need is a guy who isn't a jerk. You have to trust him to go slow and to stop if you're hurting. I was lucky that my first guy really wanted to get into my ass, so he took his time and listened to me when I told him what I needed. The best guys will rub your clit for you when they're in your ass. There's nothing like the feeling of your man deep in a place where most girls won't let him go, while you're coming all over his cock. Learn how to do it right, and he'll be back for more."

Lisa remembered that Terry's boyfriend left the scene pretty quickly after that conversation, so she probably didn't take Shawna's advice. But Lisa was taking it now, rubbing her clit as she pushed the plug into her ass. She felt a momentary discomfort as her anus stretched over the wide part of the plug, but that ended as soon as it was fully inserted. Then, the only sensation that Lisa felt was fullness. Lisa slowly teased her clit as she pulled the plug partially out and then pushed it back in. She could tell that it was going to take some time until that was comfortable, especially with the larger plug, but she couldn't say that she found the sensation unpleasant — certainly not painful. She thought that she could at least tolerate anal from Bill, after more training.

Happy with her progress, Lisa cleaned her toys, got ready for bed, and fell into a deep sleep.