Sexy Fun Times/Work/Doctor/Karen
"This is Karen," Sally says. Dr Jim was supposed to see her but he's a bit tied up."
Karen looks nervously at you. She is small for seventeen and quite attractive. Her dark hair is cut fairly short and her face still has the bold but innocent look of a teenager. The buttons on the front of her white blouse are stretched across her breasts and she is wearing jeans.
You smile at her. "Will I do," you say.
She smiles back, stands up and follows you into your room. "Now, what seems to be the problem," you say.
"It's a bit embarrassing," she says, blushing. You give her the usual spiel about confidentiality etc, and wait for her to speak.
She takes a deep breath. "It, It's my boyfriend... He wants to do things."
"I'm sure it's nothing I haven't heard before."
Another breath. "He wants to put it in my bum."
"And you don't?"
"Well, I'm not sure. Isn't that what gay men do? Does it mean he's gay?"
"Yes, and no. Anal sex is something a lot of hetero couples do. Not all girls like it and a man should always ask, but it sounds as if your boyfriend hasn't tried to force you."
She shakes her head. "He did... sort of... but I was worried that it would hurt so I pushed him off."
"If he's careful and uses plenty of lube, it shouldn't, but if you like I could examine you to make sure there's no problem."
"Would you? I want to be sure."
"Take off your jeans and panties and get up on the couch," you say. She goes behind the curtain and when she calls you see her on her back with her hands over her pussy. "You need to roll on your side and bring your knee up," you tell her.
The giggles nervously and does as she's told. Her ass is perfect. Smooth, round and feminine; creamy white and without a blemish. "Sorry, cold hands," you say when she jumps. She just giggles.
You spread the cheeks of her bum apart to reveal the tight, slightly darker starfish of the anus. She shifts slightly to get more comfortable. "I need to feel inside," you say. "The cream might be a bit cold."
You pick up a pair of gloves and a tube of KY and spread some of the jelly into her ass crack making her giggle again. When you press against the starfish, she tenses up. "Try to relax. Push back as if you're having a poo," you say.
She tries, and eventually you manage to get a slippery finger past her sphincter. She is panting a little but not resisting. "Is it okay," you ask.
"It, It feels weird, but it's okay," she says.
You push the full length of your finger in and wriggle it around a little, feeling the smooth walls of her colon and the tight ring of her sphincter gripping you. "That's very good so far," you say. "Do you want to try something bigger? I am guessing that your boyfriend's cock is bigger than my finger."
She stays where she is. All you can see of her are the perfect globes of her bottom and the entrance to her asshole which has almost closed up again. She mumbles something which you take as assent.
"Stay there, Ill be back in a minute," you say.