Jenna Fischer's Therapist (RoleplayMaster x Celebstars)

Grinning, a soft sigh left his lips as she began to stroke him. "Thank you." he replied, letting his finger move in and out of her at a quicker pace. Due to the lack of pleasure for a long time, it would feel really really good. "You can taste it if you like, I don't mind." He winked. "Either kneel or bend over, or we can 69." He offered, preferring the first two options, but open to all three. It wasn't that he was against giving oral, but focusing on someone else's pleasure wasn't something he liked when he was getting oral too.

Her lips were soft and moist, they were tingling beautifully which made her feel nice. With a hand on his cock, she could feel how hard he was for her and she liked that. It made her feel desirable and sexy, like she was a woman with plenty to give still. As she was looking over her shoulder at him, she saw his wink after he suggested she could taste it.

Gulping, her eyes lowered to hip where he was poking his cock against her. Moving off the sofa, Jenna landed on her knees, the fall wasn't that high and she turned around seeing the male lay there still on his side.

Lowering her gaze to herself, the arm which held her bra in place looked stupid now. She was about to give the man head yet she was still trying to hide her breasts? Dropping the undergarment, those heavenly motherly breasts drooped an inch to hang naturally from her chest. Pert nipples stood upon her milky jugs.

On her knees, she reached a hand forward to grasp the base of his cock, holding it still as she hovered her mouth just above it. Placing her tongue to the tip she ran it in circles across his hole. That ring upon her left finger landed on the sofa to steady herself, holding her upright while she licked him up and down.

Finally wrapping her lips around the dick, she bobbed her head up and down the first quarter. Her hooped earrings shook and her hair fell over her forehead and ears making a mess of her. Lifting her left hand up she combed it through her locks to clear her face before she removed the other hand from the base of his shaft. Rolling the male on to his back, Jenna sat up more and let his manhood stand up tall by itself.

Sucking in him once more, she went halfway and tried to find some rhythm, although she was out of practice.

The bra lightly fell to the ground, revealing the breasts he had briefly rubbed before. They had been soft, and now that he could see them, he could tell they would be fun to play with. As her body rose and leaned over him to begin her oral work, a hand reached down to cup a breast, gently fondling it and rubbing the nipple with his thumb. While his touch was sometimes rough, it was the sort of roughness that was pleasurable and not painful.

Groaning as she began, she seemed like a pro. Her movements were fast and shallow, only taking a small part of his cock at first. He did not complain though, as the work she did with her tongue was magical. "Jerk it off and suck the balls on occasion..." He suggested, closing his eyes and moaning in pleasure. "You're an absolute goddess with your mouth, and you have the beauty to match." Henry told her, feeling a trickle of saliva run down the shaft of his dick.

Her left hand took hold of his cock after she had taken her mouth away. Jerking him, she lowered her face and went for his balls, popping one in her mouth and tasting it. Comforting it with her tongue and soft lips, the mother was showing care and attention to his genitals with precise expertise. How her husband didn't want this was mind boggling.

Repeating the process with his other testicle, Jenna finally took his shaft back in to her mouth and bobbed her head up and down. While he played with her breasts, she would sometimes moan when he played roughly with her but it wasn't rough enough to stop her from continuing.

Hearing her moans from the rough play, he knew this mother was a naughty girl. Giving her nipple a small twist, he felt his orgasm approaching. Pushing her down on his cock, he began to cum, shooting a nice load into her mouth. Grunts left the man as he released his seed, before finally releasing her head and pulling out. "Bend over on the couch." Henry instructed, waiting to doggy fuck her. When she got into position, he pushed her arms away, forcing the older woman to support herself with only her legs and face. At long last, she would feel his cock penetrating her, sliding in and out of her untouched pussy. It was definitely one of the biggest she had, at least during her time with her husband and leading up to that relationship. But it had been so long ago that even a two inch dick would have felt good. The man stood over her, thrusting downward into her pussy to provide more power into his movements, and therefore more pleasure.

Frowning a little as he held her in place, Jenna felt his cock pulsing in her mouth. Seed sprayed in to her mouth, hitting the roof of her gum and crashing in to her pearly teeth. Once she was let go and his dick was removed from her lips the older woman didn't have time to catch her breath, being ordered to bend over instead.

Getting on to the couch, the one he seemed so worried about being stained with oils, Jenna was on all fours, knees and hands down on the fabric. "Ugh" she gasped, not because he was fucking her yet but because she landed on her face, her chest lowering down, making her ass stick up in the air more.

Once he had inserted himself in to her, Jenna opened her mouth wide and moaned. Her pussy accommodated him and she was tighter than he may have expected her to be.

Henry groaned as he entered her, her pussy extremely tight from being untouched in so long. His hands gripped her oily ass, gripping it and groping it as he pounded her from behind. Her moans turned him on immensely, and he wanted to know how much she was enjoying herself. "How much have you missed being fucked?" he asked with a smirk, a thumb moving to rub her ass hole for added pleasure.

The mother and wife was in a submissive position as she was mounted from behind and fucked for the first time in a long while. "Ugh...Mmmm" she whimpered. Jenna scrunched her fingers up in to fists, catching the fabric of the sofa under her nails in the process. "I've missed it so much." Rolling her eyes up in to her head and biting her bottom lip, she focused on his cock, loving the feel of it sliding in and out of her cunt.

"Be nice and loud." he told her, thrusting downwards into her pussy and getting deep extremely easily due to the position. "When I'm done with you, the only thing you'll be able to think about is my cock." He promised, changing from rubbing her ass with his thumb, to sliding his thumb inside her ass. After a few more moments, he pulled out, grabbing some of the massage oil and using it to lube up his cock and Jenna's ass. Slowly, the tip of his cock eased inside of her, as with the rest of it, keep the older woman in the submissive position the entire time. She needed cock, and likely would let herself be treated in any way just to get it. Well, that's how Henry saw it at least.

God her pussy was wet. She was loving his cock buried in her and especially with how deep he went. The thumb in her asshole added something different to the experience, yet she never complained. That was until....he decided to put his dick there. Shuddering when he left her cunt, the mother felt him lube her up. Looking over her shoulder with worry she felt him press himself in against her.

With her being an anal virgin, it slipped in with a tight squeeze but in a less painful way with the added oil to help him slide in.

"Ugh....fuck..." Jenna moaned, more to the fact that she was now being fucked in her asshole.

Hearing her deeper, guttural moans told him that the woman was enjoying the anal quite a lot. Her entire body lurched back and forth as he thrust, gradually getting faster as she grew accustomed to the different penetration. The tighter entrance made everything twenty times more pleasurable, so it was not much longer until he came, his semen leaking out of her ass gently. "I think this is good progress in ensuring you heal mentally." The therapist smiled, giving her ass a squeeze as he pulled out.

The adulterer moaned and kept her hands clenched tightly as her ass was fucked. The male seemed to enjoy it more to. The pace quickened and it wasn't long before he came in her tight entrance. As he pulled out, a long drip of semen came out, sliding down her and running towards her cunt. Jenna was still moaning, calming down from her pleasurable high.

With what he said after, she started to think that this may actually be therapy. That it was ok, especially when she started to think of her husband again.

Getting dressed once more, Henry watched her body relax at the lack of penetration. "Our appointments will be weekly, and you will do the exercises I prescribe. Along with any I have previously stated, I want you to masturbate as much as you can. Our appointments are Saturday, so maybe on a... Wednesday? I want you to try and sexually exhaust yourself. This means lay on your bed with some porn or your imagination, using toys or your fingers, and cum as much as you can. If you feel like passing out at the end, you have done it right." He smiled. "The closer it comes to our appointment, the less masturbation you should have. Finally, one night try masturbating using just your ass. Rub it, finger it, anything you want. Trying new things sexually opens up your mind to trying new things in other scenarios."

Sitting on his chair, he watched her panting form. He wanted to touch her. To fuck her. But he already did that, didn't he? He could wait until next week to try again. "When you're ready, get clothed. The appointment is now over." Henry informed Jenna.