Anal 101

Anal 101

"Want to try something new tonight?" Mike asked. He slid his hand down her the side of her breast, dipping into the curve of her waist, and back up to her hip.

"What did you have in mind, professor?" Jill teased. She was his T. A. and they were currently engaged in a temporary living arrangement, which would not go over well with the school.

"Have you engaged in any sort of anal play?" Mike asked. He slid his hand over her hip to her back and cupped her ass. His thumb stroked light circles over her tail bone.

"No," Jill answered. Her hips moved in time to his gentle sttokes. "That should be an exit only."

"How do you know you won't like it if you haven't tried it?" Mike inquired. He slid his finger down her tail bone to just above her anus. His other hand stroked the warm wet folds between her thighs, coating his fingers with her juices. He slid two wet fingers over her peranium to just below her buttoks. "I won't do this if you realy don't want me to, but I think you should at least try it.

Jill squirmed and panted with pleasure. "Alright, but is it ok if I face away from you?"

"It will give me better access," Mike agreed. "But I won't be able to see your face, so you'll have to tell me to stop, and mean it."

"Can I use a safe word?" Jill asked. She found it helped to have a word other than stop or no when exploring new sexual territory.

Mike was all about pushing the envelope of people's comfort zones, but he was also respectful. He never forced someone or berated them for not wanting to be adventurous. He simply found gentle ways to coax them into exploring things they would not otherwise do. "Let's have two words; one for slow down and another for stop altogether."

"Ok," Jill nodded. "How about yellow for slow and red for stop?"

"Hmm that sounds a bit familiar," Mike teased, "but if that's what you're comfortable with."

"The only other thing I can think of is peaches and cantaloupe."

"How about cherry for slow down, and pit for stop," Mike suggested.

Jill nodded her agreement and rolled to her side facing away from him. Mike pressed soft kisses to her neck and shoulders as he slid his hands up and down the front of her body. He left one hand at her breasts and slid the other down her belly. He gripped her thigh and lifted her leg, bending it back over his arm. He rubbed his fingers into her sex to coat them with her juices while he pinched one nipple and suckled the other. Jill gasped and moaned her pleasure until his fingers slid over her perineum and rimmed her anus.
"Cherry," she whispered.

Mike pulled away two fingers and continued to rim her with one. She squeaked in distress as he slid the tip of the finger into her anus. He probed with the tip, and listened for her response. When she did not say anything he eased the finger in a bit further. He could feel her juices running down from her opening to her anus, and knew she was beginning to enjoy his exploration. He moved the finger in and out, listening to her moan. After she came once he soaked another finger in her release, and added it to the one already working her anus. The addition of the second finger made Jill tense but she did not stop him. She groaned as he added a third finger, and moved himself up so he could whisper in her ear.

"Are you enjoying this?"

"Yes," Jill admitted.

"May I try sliding my cock in there?"

"I suppose," he could hear the nervousness in her voice.

"I'll put lube on it first," he stated.

Jill felt her anus clench after he removed his fingers. She listened as he squirted the lubricant onto his hand and stroked his stiffened cock. His lubricated fingers stroked over her anus, and slid inside to keep her lose and ready. She cried out as he slid his long, thick, hard shaft inside her rear.

"Are you alright?" Mike asked. He remained still waiting for her to answer.

"It feels uncomfortable."

"Sorry," Mike apologized. He withdrew to his tip and teased the small opening with it. He used the hand he'd been using on her breasts to rub her sex. After she released a few more times he slid his cock a bit further into her anus. She did not seem to mind it this time. He continued stroking her sex to make her come, and inched his cock into her anus until he was balls deep inside her. He slid fingers inside her warm wet opening and used the heel of his hand on you clit.

Jill writhed and moaned as he thrust inside her from both sides. She turned her head and met his mouth with hers. Their moans intermingled as he filled her with his release, and she gushed over his fingers.

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