Teddy Visits a Therapist

Teddy could sense her discomfort, her uncertainty. He felt a little weird himself. He quickly buckled up his pants, carefully laid the cum soaked towel on the couch, and excused himself.

Dr. Lowenstein didn't walk him to the door, worried about someone possibly being right outside when she opened it. But, as he reached the door she realized that he might open it too far, revealing much more of her than if she was holding it open for him, standing behind it.

And, he did precisely that. A wave of panic swept through her as she looked out past the door into the hallway, leaning back against her desk, hiding her half-naked body behind her silk blouse. Fortunately, nobody was there.

Teddy turned around to say goodbye. "I should come back in two or three weeks, doctor?"

Dr. Lowenstein took a deep breath, trying to regain her composure, her demeanor as his doctor, but also wishing that he had asked this question before he had opened the door. "Three weeks, no two weeks, actually, next week, next week would be better, Teddy, yes."

"Okay, Dr. Lowenstein, and, um, thanks."

She smiled nervously and thought 'Please shut the door, Teddy' as she in fact said, "My pleasure, Teddy."

She breathed a sigh of relief as the door did finally shut.

- - - - - - - - - - - - - -

A few more weekly sessions passed with repeated administrations of the therapeutic exercise.

The good news was that he continued to improve. With each session he lasted longer and longer before feeling the need to ejaculate.

Dr. Lowenstein always came to his sessions well prepared for her part in the exercise, working her way through an assortment of pretty undies and sexy lingerie. Actually, additional good news was that she found herself enjoying the morning preparation for these sessions. She would spend some time selecting which outfit to wear, trying on different undies, admiring how she looked in the mirror. It had been many years since she had spent time modeling lingerie before her bedroom mirror. And, she was certainly looking forward to once again playing with Teddy's young, hard cock. She even purchased new lingerie, smiling as she realized that she should be able to write off some of the costs as a tax deduction, although she wasn't too sure that she would be willing to explain this to her accountant.

The bad news was that Teddy was improving so much that it was evident that his level of arousal needed to be escalated. It was time to take another baby step forward.

In the next session, Dr. Lowenstein was standing before Teddy in a green halter flyaway babydoll, held together by a slim ribbon, tied in a bow. The ensemble was completed by matching green doodle mesh, thin waistband, silk bikini panties. The babydoll did wonders for her cleavage, yet still providing rather nice support. Her breasts stood up proudly, like two mounds of smooth vanilla ice cream. The baby doll was quite lacy but the silk fabric was solid in the most important places, including, of course, her nipples. The nipples were well hidden. Well, not really, as you could clearly see their outline, poking out against the smooth silk.

Dr. Lowenstein was quite pleased with her ensemble. It was one of her new purchases, obtained especially for her clinical work. She felt that she really looked sexy and should then offer excellent stimulation for Teddy. She was feeling quite excited herself by the time Teddy arrived, as she had been wearing the baby doll and panties beneath her much more demure, business-like suit throughout the day. It had been particularly tantalizing when she was providing her weekly report to the director of the clinic, Dr. Fritz Perlman. The silk felt so nice against her skin. Knowing that she was so provocatively dressed while he sat there, unknowingly across from her, was rather titillating. By the time the meeting was over she could feel warmth emanating from between her thighs. She was already down to the babydoll by the time Teddy arrived for his appointment.

Teddy was also very pleased, very happy with the outfit. "Oh man, Dr. Lowenstein, wow, you really look great in that!"

"Do you really think so, Teddy?" Her self-consciousness was long gone. She spun around to give him a full appreciation of its effect. Just before he arrived she put on a splash of additional perfume and the lovely scent drifted across to him as the lacy skirt of the babydoll swung with her twirl, revealing her silk bikini panties.

She wanted to get his penis out right away. She suspected that he must already be good and hard. But, there was also some important matters to discuss. This was, after all, clinical therapy. She sat down next to him. His eyes went to the bulge of her cleavage, and her hand to the bulge in his pants. "You know, Teddy, that you are making remarkable progress. I am really quite pleased with how long you can now maintain control." She began to undo his pants.

"Thank you, Dr. Lowenstein," Teddy happily replied. He felt like a student getting the compliment of his teacher for doing so well on his homework.

"Oh my," she said as she pulled his hard cock out from his shorts. "He looks very happy to see me today."

He beamed with pride and basked in the pleasure as he felt her fingers wrap around his stiff, naked cock. It was so nice to be able to enjoy the moment and not have to worry about cumming. He could now last quite awhile before she had to apply the squeeze technique, and even thereafter it continued to be quite a bit more time before another squeeze was needed.

"Have you noticed any improvements with Penny?"

Teddy would have liked to tell her that everything was fine. He didn't like disappointing a woman who was dressed in such a revealing baby doll while she masturbated him. However, she was still his doctor and it was important to be honest during the course of treatment. "Well, yes, I'm not having any trouble at all, except, um." He hesitated to say more.

Dr. Lowenstein let go of his cock and sat back. Her breasts notably jiggled with her movement. The cups in the baby doll did provide support, but they were hardly constraining. "Except what, Teddy? C'mon now, there is something on your mind that you're not revealing." She leaned forward again and lightly rubbed the head of his cock with the palm of her hand as she said, "Tell the doctor everything, Teddy, even if it is personal or embarrassing." This was a pretty effective technique for extracting the truth from a patient, although not one that she would likely use with all of her male patients, or frankly with anyone other than Teddy.

The problem, though, wasn't embarrassing for Teddy. It would more likely be potentially embarrassing for her. That was the problem. "It's, well, it's just that I do still have some difficulty when she's, you know, naked and everything."

Dr. Lowenstein withdrew her hand once again. This was an understandable problem. It was an objective, scientific fact that the sight of a naked female body would be quite arousing, and in order for the treatment to fully generalize to the conditions of his activities with Penny, this situational context would need to be recreated within the therapy session.

Dr. Lowenstein's heart pounded as she contemplated what she knew she had to do. Any professional surrogate that she would have hired for Teddy would have had to remove her clothes entirely, at least at some point. She could not pretend that it would not be useful, important, and even necessary, for his treatment, for her to likewise remove her own clothes.

But, the thought of being so fully exposed, so entirely naked, in front of this young man. Letting him actually see her nipples, her bottom? My goodness, even her cunnie? Well, it did seem to be inconsistent with her professional role, her status as a doctor, his doctor.

Yet, it was precisely because she was his doctor that she knew she should, she had to, get naked for him. She pulled the ribbon holding together the front of her baby doll

Her full breasts plopped out and jiggled into view, and they were quite a luscious sight to see. Teddy's eyes widened with delight, as did his cock swell with equal pleasure. He slowly stroked himself as he gazed at her big round breasts. They stood up very well, at least for a lady her age. They did hang down a bit, but this reflected in part the fact that they were so full, so womanly.

Teddy noticed her face turning red, but he could not understand why. These were breasts for which any woman should feel terribly proud. There was no reason for her to feel embarrassed. "Wow, Dr. Lowenstein, man, I mean, they're like, really big."

Dr. Lowenstein glanced away in self-consciousness at his comment and said quietly, "Thank you." Her blushing was not due to any feeling of inadequacy or uncertainty, it was the insecurity over what she was doing, it was the embarrassment of sitting with her breasts fully exposed to someone who was young enough to be her own child. She once again felt very unprofessional, as if with the exposure of her breasts she had lost her professional stature, reduced to being simply a sexual object for his prurient interests, as if she was nothing more than a stripper at a men's club showing her tits to a customer.

But, it was also rather nice to hear his compliment. She had not shown her breasts to a man for quite a number of years, and she couldn't deny that it was rather, no very, exciting to be doing it once again, to be enjoying the fact that a man found her body to be so exciting to see.

She also knew that she blushed at his compliment because she was embarrassed at how nice it made her feel. Her heart was pounding with pleasure, not just with anxiety. In fact, what better way perhaps to enjoy such showing off than through the facade of acting as his doctor. She could play the stripper, but not really be a stripper. She was stripping as his doctor.

She stood up before him, grasped each breast in her hands and lifted them up to provide a better display. She smiled sweetly at Teddy and said, "Does Penny like to show them to you like this?"

Teddy was now pounding furiously on his cock. If he wanted to, he could cum at any time, but he wanted this to last, and he had been learning well. He stroked hard, but he felt in control, and it was quite a fantastic feeling to be stimulating himself so much with his eyes and with his hands, and yet to be able to sustain and maintain these sensations at such a high level for so long. "Yes, ma'am," he replied.

Dr. Lowenstein let go of her tits, which jiggled and shook as gravity pulled them down to rest, or hang, against her chest, like two large, oblong balloons stretched with water to full capacity. "And, I imagine that she shows you other things as well?"

Dr. Lowenstein turned her back to Teddy and slowly pulled the straps of the baby doll from each of her shoulders. She let it fall gracefully to the floor.

She was now standing before him dressed only in her bikini panties.

She slipped her fingers into the waistband and slowly pulled the panties down to just passed her buttocks. She looked back at him over her shoulder as she held the panties just below her round, white orb.

She felt a little self-conscious about this, wondering, worrying, if her cellulite would be a source of distaste for Teddy, negating the fact that she was now letting him see her naked bottom.

Teddy, however, hardly noticed any cellulite at all. There was in fact very little to notice. What was of most interest to his eyes were the full, round, soft, white cheeks, split by the most heavenly crack. He considered letting himself cum so that he could shoot his load across the carpet onto those ivory hills and into that dark, inviting valley. But, to do so would be inconsistent with his treatment and would as well end the pleasure well short of where it could still further go.

Dr. Lowenstein then slowly bent over from the waist, at the same time gradually pulling her panties down her thighs. When she reached her knees she let her panties fall to the floor, gathering in delicate green layers around her ankles. She then placed her hands on her knees, looked once again back at Teddy, bent her knees, and pushed out her bottom.

The effect was magnificent. Her butt was now gorgeously stretched tight and rounded. The crack opened up, revealing to his eyes her womanly rose bud, winking at him down deep in the brown valley of her white cheeks. His eyes would have loved to linger there but they were also drawn to further pleasures and so followed the large crack down to where it ended but was picked up by a much more delicate crack that could be seen hiding beneath a soft, delicate shrubbery.

Dr. Lowenstein smiled back at him, her face now a deep red. She could feel the heat of her blush. She knew that this was a very, very provocative pose, displaying for him both her anus and her vagina, although, perhaps, as a surrogate she should use less medical terminology. Well, no matter what you called them, she had them poking out right at his face. She asked, "Do you like what you see, Teddy?"

"Your butt is really beautiful, Dr. Lowenstein."

Dr. Lowenstein smiled graciously back at Teddy. "Well, thank you, Teddy, how very nice of you to say so." She said this in a rather cliched, formal, business-like manner, like she had before when a patient had complimented her on a new dress or hairdo. However, this did seem to be a bit different, not only because it was the sight of her bare fanny he was complimenting, but also because she was secretly quite pleased to hear it. She knew that her bottom was not quite as firm as it used to be, and she couldn't help but appreciate his delight with her butt.

Teddy was leaning forward in the couch, grasping, grinding, stroking, and twisting his hard, swollen cock. He wondered if she would do just one more thing. It might, though, be asking a lot. She could be offended. It might even make him seem like a pervert.

Dr. Lowenstein, the good therapist that she was, could see that his mind was distracted. She asked, while still displaying her bottom for him, "What are you thinking right now, Teddy?"

He hated when she forced him to reveal his thoughts, without censorship, but, he had to admit that it was always good for his treatment. "Well, um, doctor, I was, well." He swallowed in nervousness. "Teddy, I am your therapist. You can tell me anything." As she spoke she waved her bottom back and forth to encourage him to open up. Being naked with a patient did appear to do wonders in drawing out his thoughts. What patient could deny the request of such a sweet waving bottom?

"Well, doctor, I was wondering, um, Penny does do one thing that I like."

"Well, Teddy, you should tell me. If we want this treatment to generalize to your pleasures with Penny, I need to know what it is that does in fact pleasure you."

"Yes, well, she." His voice became a whisper as he said, "She spreads open her cheeks."

Dr. Lowenstein had bent over in front of guys in the past. She in fact liked to do it from behind. But, she had never spread open her cheeks. That did seem to be a bit raunchy. It was essentially saying, 'Look at my asshole,' and she was certainly not into, had never even done, anal sex.

But, as a good therapist, she should not pass judgment on her patients. Patients will at times engage in things that a therapist will find to be personally objectionable, offensive, or even disgusting, but it was important to maintain an unconditional positive regard rather than becoming personally offended. One should not impart your own values onto the patient, particularly when it came to sexual preferences.

Dr. Lowenstein's face got even a darker red, if that was possible, as she tried to smile bravely while actually feeling very, very confused. "Well, of course, Teddy, I would be happy to."

She reached back, grasped each cheek in her hands, and spread them open.

The brown valley came full into view, the slopes of her cheeks being stretched apart by her fingers. And, at lower center, being now as well partially pulled open, was her brown, nether hole.

Teddy had not yet had anal sex with Penny, but he sure did want to. It was a big fantasy of his, and having the doctor display herself like this to him, was lustfully ecstatic.

Dr. Lowenstein looked back at Teddy as she spread open her ass cheeks. She could see by the reaction on his face as her anus came into view that this was a good therapeutic move. Her mentor had always said that the best sign of a good interpretative remark was the reaction of the patient, and there was little doubt that opening up her cheeks was resulting in good therapeutic work.

She asked flirtatiously, a mischievous smile on her face, "What is it that you are looking at, Teddy?"

Teddy really didn't want to say. It was too embarrassing to say it. He really couldn't admit to it. He didn't say anything.

"C'mon, Teddy, let your doctor know what you are thinking?" She even tried to wink at him with her anus by squeezing and puckering with her sphincter. She couldn't believe that she was really doing something like this, but she knew that a good doctor was often asked to be brave and bold.

"I'm, I'm, um, I'm looking at, you know, your, um," his voice went down to a whisper. "Your anus."

Dr. Lowenstein smiled and blushed at the same time. "Is that what you call it, Teddy? Do you tell Penny that you like her anus?"

"No, ma'am," Teddy replied, his hand working hard on his cock, his body squirming with intense pleasure and embarrassed discomfort.

"Well, what do you call it?"

Actually, Teddy had never called it anything with Penny. He knew what he liked to call it. He had a lot of names for it. 'Anus' was not one of them, but he had never actually used any of his words for it with Penny. "Your, um, your asshole," he groaned, and now, finally, had to apply the squeeze technique to keep himself from ejaculating all over her carpeting, as well as her asshole. He clenched his eyes shut as he squeezed hard on his cock. His eyes were squinched shut in part because of the displeasure, the strain, and the pain of the squeezing of his fingers on his dick, but also because he simply could not continue to look at the delightful, enticing, provocative sight of Dr. Lowenstein spreading open her ass cheeks, openly displaying for him her butt hole, her rosebud, her poop chute.

Dr. Lowenstein found herself breathing a sigh of relief when she looked back and saw him close his eyes and apply the squeezing. She was beginning to feel quite uncomfortable posing for him like that. It felt rather obscene, perhaps even frankly demeaning, to be bent over in front of this young man, spreading open her bottom cheeks so that he could masturbate to the sight of her puckered anus. She wondered what it would be like to speak to him later, as her doctor, fully dressed. Would she still command authority and respect, after she had been bent over for him, showing him, displaying for him, her butt hole? She knew though that her insecure thoughts were just problematic counter-transference feelings that would go away with time and perhaps her own self-analysis. Nevertheless, as soon as his eyes were shut she let go of her cheeks and stood up.

She moved over to again sit by him on the couch. She placed her left hand around and over his shoulder as he squeezed hard on his cock. "Good job, Teddy," she said. "You really lasted quite a long time there."

He gasped, "Oh yes, doctor. That was real helpful. I really think I'm getting better."

Dr. Lowenstein reached over with her other hand for his hard cock and began to slide her hand up and down its stiff length.

Teddy let out a soft groan at the first touch of her soft, womanly fingers. It had been plenty arousing before when she was masturbating him in her business suit. There had been something uniquely erotic about that: him being naked, her being fully clothed.