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Mentor (closed)

Fun



Josephine smiled as Jill left the room. She took this first lesson in proper spirit. Josephine could already tell that Jill would have no trouble obeying any reasonable rules she set, once she understood them. Thus, the rules would serve their proper purpose, a gentle reminder of their relative status and an occasional source of erotic fun.

Today had more to do with the latter. In that spirit, Josephine got out of bed and took from her closet a silky black lace corset bra bustier with garters and laid it on her bedspread. She added to this a pair of vintage Cuban heeled black stockings. Normally, she would have Jill help her into these, but today wanted to surprise her. Once she had donned the bustier and stockings, she stepped into a pair of black stiletto heel pumps. Finally, she pulled a riding crop from her dresser.

“The kitchen is all clean,” Jill announced as she entered the bedroom and found Josephine dressed this way, sitting on the foot of the bed with her legs crossed.

“Very good, Jill,” Josephine said solemnly. Then she slapped the head of the riding crop into her left hand and asked, “Are you ready for the lesson we discussed?”






 
A crop..

Jill froze as she entered the bedroom.. She saw the Professor holding a riding crop. She had never seen one in person. Her face must have turned white because she felt light headed as she realized that the Professor was serious...

The Professor looked amazing in her silky black lace corset bra bustier with garters. "My gosh Professor you look stunning." Was all Jill said as she knew now this was serious and none of it was a game.

Hearing the sound the crop made in the Professor's hand, sent a shiver down Jill's spine. "Yes Professor I am ready for my lesson."

Unsure of what to do Jill just stood still and waited.
 
Dexterity



Josephine stood. She twirled the riding crop a couple times, like a majorette with her baton. She had not wielded it in years. It felt good in her hand.

Smiling affectionately at her new lover, she simply said. “Bend over the mattress, Jill.”






 
Bottok up

Jill didn't say a word...

She moved to the bed and bent over the mattress. As she did that she looked back at the Professor twirling the crop.

Jill was scared and not just a little. As she lay down she could feel her heart racing like she was running sprints. She took a deep breath and just waited.
 
while she was laying there

Jill lay on the soft bed with her bottom on display for the Professor. The giggling from only a few minutes ago was gone. She could feel her palms getting sweaty. At first she was not sure what to do with her hands. For the moment they were at her side.

She wondered if it would be more comfortable to adjust them so they were over her head. Or should she leave them there. If she left them like that she could try to cover her bottom if the Professor was a little too firm with the crop. That may not be the best idea she told herself.

Her throat dry, she cleared it as she moved her arms over her head, and said. "Like this?"

Last night when she slept she didn't notice the bed but it was really very comfortable, she closed her eyes and told herself no matter what she was not going to move her arms, she could handle it.

Jill could not believe just how excited she was becoming, the Professor had not touched any part of her body since last night, but here she was so wet she could feel it once again running down her leg. She wondered if something was really wrong with her. She thought really Jill this is what does it for you bending over this woman's bed displaying your bottom like this, waiting for her to spank you a riding crop...

"Professor I am ready." was all she could think to say.

As she closed her eyes and tried to relax but her whole body was tight, there was really nothing she could do about it.
 
Last edited:
Interrogation



Josephine started by gently caressing Jill’s bottom with the pliant leather flap. She moved in a figure-eight motion, tracing an oval on each side of Jill’s derriere, the sign of infinity.

“Do you understand why you’re being punished?” Josephine asked, then slapped Jill’s left butt cheek with a quick flick of the flap. She did not hit too hard, not wanting to make this hurt any worse than a bare hand spanking.







 
First

"Josephine started by gently caressing Jill’s bottom with the pliant leather flap. She moved in a figure-eight motion, tracing an oval on each side of Jill’s derriere, the sign of infinity."

The soft caressing felt so nice to Jill she could feel her body relaxing, and she could feel the goose bumps forming on her bottom and her thigh's. This was making her even more excited.

She heard the Professors question and then felt the mild sting of the crop on her left cheek. She didn't jump, she just answered the Professors question.

"Yes Professor, because I was wearing your dirty panties. I was wearing them because I wanted to feel flow to you."
 
Simplification



“Don’t complicate it or make excuses,” Josephine returned to gently caressing Jill’s bottom with the crop’s pliant leather flap in a sideways figure-eight. “You are being punished because I told you to wear no clothes here without permission.”

Josephine then slapped Jill’s right butt cheek with a quick flick of the flap. She did not hit too hard, not wanting to make this hurt any worse than a bare hand spanking.

“You are being punished because you did not follow one of my rules.” She slapped Jill’s left butt cheek with a quick flick of the flap. “Do you understand?”

Josephine again stroked Jill’s buttocks with the crop with a figure-eight motion, tracing an oval on each side of Jill’s derriere, the sign of infinity.








 
is it red...

Jill could feel the crops touch, she also know it could have been a lot worse.

"Yes Professor, I understand, from now on there will be no more excuses. When you tell me what you want I will follow your instructions." Jill said that as her voice got a bit higher as the crop touched her bottom.

Jill also felt her body moving into the touch of the figure eights as the Professor made them.
 
Reinforcement



“That’s all you need to say,” Josephine told Jill.

Never breaking contact between the crop flap and Jill’s buttocks, Josephine used her free hand to explore Jill’s womanhood, finding it already quite wet. Josephine inserted one, then two, fingers into Jill to prepare her. She then picked up the panties in question and started stuffing them far up Jill’s vagina.

“This will reinforce in your mind the reason for your punishment,” she explained as she pushed the last of the lacy garment in, so just a bit dangled out between Jill’s labia. Then Josephine took a step back and started swatting her bottom with the riding crop, alternating between cheeks. She never struck hard enough to cause a welt, but a rosy glow soon rose on Jill’s tight derriere.







 
arching her back

Jill could feel the crop striking her bottom and it was starting to get warm, not uncomfortable but warm. Then she felt something else the Professor's finger moving inside her, it would not have been difficult because Jill could not remember ever being more wet.

As the Professor pushed her first finger inside her she arched her back causing her bottom to push out just a little more. Then she felt the second, her hips started to slowly tried to push her fingers deeper inside her.

Just as her hips were starting to work with the Professor's fingers they were gone. Jill let out an. "Mmmmmmmmphhh" Then she felt something else, not sure it was like gushy she thought it was some type of odd dildo, but it was too soft for that. It felt very strange to her, and for a moment took her mind off the spanking.

However soon the Professor was back it. Striking each side of her bottom, causing it to get warmer and warmer. She wondered if she should be counting. She really hoped not, because she was not, but then she remembered that the Professor had not told her to count. She was lucky there, but she also needed to have an orgasm.

The more primal part of her mind was causing her hips to rock back and forth making her, like grind against the bed. She closed her eyes and got herself to stop, but she did not know how long she could fight the urge... She was so excited.
 
Turning About



Josephine delivered ten riding crop slaps to each side of Jill’s buttocks. She left no welts, just a rosy glow. She set the crop aside.

Then, gently stroking the small of Jill’s back, she said softly, “Roll over so you’re laying face up.”







 
Yes Professor

Jill's bottom feeling warm, her cunny feeling funny with an unfamiliar object inside her.

"Yes Professor." she said as she rolled over onto her back.

laying looking up at the Professor with a please let me cum look on her face..
 
Finale



Josephine stood at the side of the bed and gently stroked Jill’s womanhood, from which a bit of black lacy fabric still protruded. Josephine flicked this with her finger at the end of each stroke.

“Will you be more careful about the rules from now on, Jill?”







 
Figuring it out

As she rolled over Jill got a look at what was protruding out of her. It took a second but she realized it was the panties she had been wearing to make breakfast because she felt really uncomfortable being naked while cooking.

"Yes Professor, I understand now just how you feel. I will never wear anything without your permission again."
 
Positive Reinforcement



“Yes Professor, I understand now just how you feel,” Jill said. “I will never wear anything without your permission again.”

“For that, you get a reward,” Josephine replied as she knelt down between Jill’s legs. “I’ve been looking forward to this for a long while.”

She leaned forward and kissed Jill right on her clitoral hood, dabbing her tongue there a few times. Then she started licking Jill’s labia, switching between them and her clitoris, careful not to stimulate it too much yet. She wanted to build up to the most intense orgasm Jill had ever experienced.

As she tongued Jill, she began pulling on the bit of her black panties still protruding from Jill’s vagina. She’d played this game before, from both sides. So she knew the extraordinary sensations added to her cunnilingus as the lacy fabric began unfolding and moving inside Jill as she very slowly extracted it from her.







 
not going to last

Jill felt the Professor between her legs as she lifted her head to watch her.

She felt the Professor between her legs as she said. "I have been looking forward to this for a long while." That made Jill wonder if the Professor might have eyes for her since the day they first met.

Jill felt the Professor kissing her hood, how she wished the Professor would just Press down on it and make her cum. Then she felt the Professors tongue, that made her arch her back as her head hit the mattress. Then it stopped, and Jill had to bite her tongue, she wanted it so bad.

Then the Professors tongue on her labia each side, Jill's hips trying to move in time with her tongue. Then she felt the Professor slowly starting to work the balled up panties inside her out of her. It felt unlike anything she had ever felt before.

Jill told herself to relax and enjoy what the Professor was about to do to her.
 
Double the Pleasure



As Josephine tongued Jill, she began pulling on the bit of her black panties still protruding from Jill’s vagina. She’d played this game before, from both sides. So she knew the extraordinary sensations added to her cunnilingus as the lacy material began unfolding and moving inside Jill as she very slowly extracted it from her.

At first, she started licking just Jill’s labia, eventually switching between them and her clitoris, careful not to stimulate it too much. Then, after several minutes, when about half of the panties had emerged, she began concentrating on Jill’s clit with her tongue. As she did, she continued to draw out the textured fabric, adding its unique sensations to the intensity her tongue provided.







 
cant help it

Jill was already so close to the edge.

Jill was moaning and her body was getting tight, she knew she was not going to last long...

"Professor, Professor, I'm I'm going to cum, I cant help it.."
 
Finally!



“Professor!” Jill moaned. “Professor! I’m... I’m going to come! I cant help it....”

Josephine just smiled, flicking her tongue even more quickly on Jill’s clitoris as the last of the black lace panties slipped out of Jill’s vagina.






 
thats all it took

Jill was overcome with sensation from the Professors tongue and the panties being pulled out of her cunny, it was too much, she was already so excited, the spanking with the crop may have been enough with her grinding against the bed but not her orgasm was going to be something so much more. The Professor's tongue was expert and amazing. That last flick of the tongue is all that was need..

Jill's hands slammed down on the bed as her body was overcame with her orgasm. Her back arched she, grabbed at the sheets and squeezed them. Her whole body shook as she came for the first time for the Professor.

Her clit so sensitive, her breathing coming in gasps.

After a few minutes she looked up at the Professor and said. "My gosh your are amazing, oh wow. Reaching out with her arms, wanting to the Professor to lay on top of her and kiss her.
 
Aftercare



“My gosh, you are amazing!” Jill sighed as the last tremors of her orgasm subsided. “Oh... wow.”

Still on her back, she reached up with her arms, looking all the world like a child seeking to be picked up and hugged. Josephine crawled up between her legs, over her body, and laid down on top of her. She kissed her deeply, letting Jill taste the remnants of her own juices on Josephine’s tongue.







 
kiss

Jill, took her time savoring the kiss she could have laid like that all afternoon.

Her mind however was already on how she could please the Professor some more.

She made herself lay back and enjoy the kiss. Their tongues dancing together, like two friends who knew each other so well. Her arms wrapped around the Professor's body holding her tight and caressing her.

For the moment Jill did not want this to end...
 
Getting Acquainted



For the moment, Josephine did not want this to end. She took her time savoring their kiss, thinking she could spend all afternoon this way. Eventually, as it always did, her mind wandered to an at hand issue.

“This all happened so quickly,” she whispered as she kissed Jill’s ear. “We ought to spend some time getting to know each other out of bed.”






 
is that a rule

Jill giggled and whispered back into the Professor's ear. "Is that a rule?"

Jill was now looking the Professor in the eyes as she said. "I need to go for my run, then I need to get cleaned up, and I have to go by my apartment." Running her hand through the Professor's hair. "So maybe I should go do that?" Jill said that more as a question.

Jill was not sure what the Professor wanted to do as next step, all she knew is that she wanted there to be more steps than just one.
 
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