Teddy Visits a Therapist

"Oh!" Peter suddenly exclaimed, and Dr. Lowenstein quickly applied the squeezing just below the crown. She squeezed a bit harder than he had been doing himself, and it was quite effective. His urge to ejaculate dissipated.

"Very good, Teddy," Dr. Lowenstein observed. The therapeutic plan was to do this until there was approximately five minutes left in their session, at which point he could ejaculate and there would be sufficient time remaining for clean up and wrap up. Teddy seemed to be doing quite well. She had to apply the squeeze technique a number of times, as it was evident that the touch of a woman's hand on his cock was considerably more stimulating than his own.

She made it particularly stimulating by continuing to whisper sultry comments in his ear, her warm breath on his ear, her perfume drifting across his nostrils, her full breasts pressed against his arm, and her sweet, feminine hand sliding up and down his cock. There was even something especially erotic about the fact that she was so much older than him, perhaps old enough to be his mother, yet this beautiful women, dressed in her business suit, was actually giving him a hand job.

Dr. Lowenstein did want the exercise to be as close to in vivo as possible, to optimize the likelihood that there would be generalization to his relationship with Penny. She inquired, "Is this how Penny does it?"

It wasn't. It was still plenty arousing, and what was unique to Dr. Lowenstein's technique (e.g., her breath tickling his ear lobe) was really nice. But, there was something missing. Teddy answered, somewhat breathlessly, his cock straining within her hand, his balls beginning to ache for relief, "Well, doctor, um, it's great, but she, well, she usually doesn't have on a lot of clothes." He blushed when he said that, as did Dr. Lowenstein.

Dr. Lowenstein had not fully thought through what it would mean to be Teddy's sexual surrogate. Well, she had, to an extent, but had not let herself really think about it. She was really quite uncomfortable with the thought of taking off her clothes for Teddy. After all, he was so much younger than her, and, even worse, he was just a student, a patient, her psychotherapy patient. She imagined that many of her colleagues might not approve of what she was doing, nor was she sure herself. When she really thought about it, they would probably really disapprove. How could she actually undress for one of her patients?

But, Teddy was absolutely correct. Quite a bit of sexual arousal is generated visually. And, the job of a sexual surrogate is to simulate the sexual act with a patient. No self-respecting sexual surrogate would refuse to remove any clothing. On the contrary, it was their job to display a comfort about, an openness toward, all matters sexual. And, finally, all of her work, her willingness to even masturbate him, might be all for nothing if she did not include the visual component.

She let go of his stiff dick. "Yes, well, Teddy." She hesitated to say more. She instead just got up off the couch and slowly began to unbutton the jacket of her suit. She could feel the blood rushing to her face as she did so. She hoped that he would not notice that. She felt quite embarrassed to be unbuttoning her jacket in front of this young man, but also embarrassed over the fact that she was feeling embarrassed. It was important to maintain her professional demeanor. If she was going to be a sexual surrogate, she wanted to do it professionally. Instead, she felt like a middled-aged woman being compelled to undress in front of a young man with a stiff cock. She thought, 'Funny how weird some of your countertransference perceptions can be.'

When the last button was undone, she removed the jacket and carefully laid it on her desk. She turned back to Teddy and began to undue the buttons of her white, silk blouse. This was really so very strange. When she had been in training she had never imagined doing anything like this. Frankly, if anyone had asked her even last year she would have been appalled that they would have even thought about the possibility. Take your clothes off for a patient? She would agree to do many things, but this? Yet, here she was: unbuttoning her blouse in front of a young male patient, his naked stiff cock poking up out of his pants.

She glanced at it. It was still rock hard, despite the fact that she had stopped stroking him. Teddy though reached for it anyway. "Uh, yes, Teddy, um, that's a good idea. You can continue the therapy while I." Her voice dropped to a whisper for the rest of the sentence: "undress, for you."

Having Teddy openly masturbate while she continued to undress made her feel even more self-conscious, as if she was putting on a strip show for him while he jerked off. This wouldn't even happen for a stripper at a gentleman's club, yet it was happening to her.

When the front of the blouse was unbuttoned, she unbuttoned the cuffs, pulled the tails from the tight waistband of her skirt, and turned her back to Teddy. She took a deep breath and pulled her arms free of the blouse.

Teddy's jerking on his cock increased in speed as he saw her bare shoulders, the white skin of her naked back, and the white strap of her bra. His mouth went dry, yet he felt an urge to swallow. He watched as she carefully folded the blouse and laid it on top of her jacket. His eyes fixed on the lovely nakedness of her back, her shoulders, and the intimacy of the bra strap stretched across them.

She hesitated again, staring at her garments lying on the desk. She took a deep breath and reached behind her for the zipper of her skirt. She slowly pulled it down, although somewhat awkwardly. She considered asking Teddy to do this for her, but perhaps that would be too suggestive. She didn't really want him to undress her, to touch her.

She bent over to draw the skirt down to her ankles. Her bottom poked out through her white silk slip.

Teddy knew that he could easily cum right now. He was in fact impressed that he wasn't gushing his cock, despite the fact that he was still playing with it and the gorgeous Dr. Lowenstein was bent over in front of him, dressed now only in her high heal shoes, slip, and brassiere. Imagine being able to actually put his cock in her from behind? He was indeed imagining that. Oops, that did result in the need to apply the squeeze technique. He squeezed hard to stop himself and to regain control.

Dr. Lowenstein carefully folded her skirt and placed it next to her blouse. She then reached for the waistband of her slip. She was glad that her back was turned to Teddy, not only to protect her modesty for as long as possible, but also to hide her beet red face. She wished that she could just will the embarrassment away.

She again bent over to remove her slip.

Teddy resumed his stroking as he watched her draw the silk garment over the curves of her bottom, down her thighs, and to her ankles.

Dr. Lowenstein was wearing an attractively matching set of bra, panties, and stockings. She did always dress well. She felt it was important for a therapist to be well dressed, and she was now very glad to have decided to wear such nice underwear today. She didn't always do that. But, for some reason, she had done so today. As she folded her slip and laid it on her skirt she wondered if she unconsciously knew this morning what would happen later that day. She had indeed thought about Teddy this morning, as she was getting dressed, and the thought of talking to him about his erection and ejaculations had caused her heart to flutter a bit. Counter-transference issues did appear to be really much more problematic in sex therapy! Well, the moment of truth had arrived. She slowly turned around to face Teddy.

Teddy's eyes widened with excitement. There before him stood the most attractive Dr. Lowenstein. He was no longer even thinking about her resembling "what's-her-name;" that actress she so much resembled. She was quite striking herself, particularly dressed only in her bra, panties, and stockings. Her breasts were barely contained within her white, lace, half cup bra, trimmed with delicate fringe. There was even a little pink bow in the center strap, just below her open cleavage, which seemed to be literally bursting from her cups. He had to wonder if she was wearing one of those wonder bras; she wasn't, but it sure appeared that way. Her breasts looked so full, so round, so firm, so prominent. He pounded harder on his cock.

His eyes traveled down, past her firm abdomen, her narrow waist, to her panties, which did indeed match well her bra. They were low cut, trimmed with the same frill, and again topped by the pretty little pink bow. His eyes though were mesmerized by the sight of the large bulge of her womanly mound. He felt that he could perhaps even see a bit of an outline of her lips. Dr. Lowenstein had a camel toe?! He could imagine what it might look like if she would draw back the crotch of her panties, and with that thought he, once again, squeezed hard on his cock to inhibit his ejaculation.

Dr. Lowenstein felt quite self-conscious, standing in front of this young man, a student at her college, a patient of hers, as he was openly masturbating in front of her as she posed for him dressed only in her underwear. She would have to admit that she would have difficulty explaining to the administration that this was in fact objective, professional therapy. She thought, 'Thank goodness I'm not using one of the therapy rooms with a two-way mirror or, even worse, having the session video taped!' She glanced at the door to double check to see that it was locked. Of course it was; she had locked it herself. But, right now, she needed some extra reassurance.

She sighed deeply, her breasts rising up in her cleavage. She had to get back to his treatment. As she saw him apply the squeeze technique, she moved over to sit down, once again, next to him on the couch.

Dr. Lowenstein's perfume seemed now even more enticing. Perhaps it was because so much more of her naked skin was now open to the air, a halo effect of having her sitting next to him dressed only in her bra, panties, nylons, and high heels. His eyes went straight to her breast cleavage, so nicely displayed by her tight, uplifting cups.

She again turned toward him, bringing her naked left arm over his shoulder, pressing her lacy cupped breasts against his shoulder, the exposed luscious boob bulging out from her bra. She took hold of his cock once again in her womanly hand. She said softly in his ear, "Does it excite you, Teddy, to have your doctor be dressed only in her panties and bra?"

Teddy gasped at the feel of her hand, the sultry sound of her voice, as well as what she said, "Oh yes, yes, doctor."

"Do you think I look sexy in my undies?"

"Oh, ma'am, yes, yes, very much." Sweat was forming on his brow and dripping down his sides.

"Would you be willing to cum for me, Teddy? I so much want to make you squirt your manly juice all over the floor."

"Oh, ma'am!" She saw him clench his muscles and thrust his pelvis, and she felt a sudden swelling in his shaft. She squeezed hard.

"Doctor, please," Teddy complained, his eyes clenched shut in the agony of his desire.

"Not yet, Teddy, the session is not yet over." She continued to apply hard pressure just below his crown. "We still have a few more minutes." When it was apparent that he would not ejaculate, she let go of his cock and gave him a bit of time to regain his composure.

She smiled flirtatiously and blew in his ear as she once again grasped hold of his hard cock, starting off though with just a mild, light grip as she drew her hand up and down its hard length. She whispered in his ear, "I bet you would like to touch my breasts, wouldn't you, Teddy."

"Oh, ma'am, I mean doctor, yes," he said, with considerable enthusiasm as he began to reach over with his left hand.

"No, no," Dr. Lowenstein scolded him. She had only been teasing him with the suggestion, the possibility, of touching her. "Don't you think Teddy that touching your doctor's breasts would be inappropriate? My goodness, you're so much younger than me, and you're my patient."

"Yes, ma'am," Teddy groaned. She was the doctor. He couldn't really argue with her.

"But, I can understand why you would want to, Teddy. Look at them. Look at my breasts, Teddy."

Teddy had been trying to be polite about the fact that her blouse was off. He hadn't wanted to stare directly at them, thinking that would be rude or childish. But, it would be fine now, as she was in fact ordering him, as his doctor, to look right at them.

"They are exciting for you, aren't they, Teddy. So full, so white. See how they rise out from my brassiere, Teddy, my deep cleavage, such a heavenly valley." She could feel his cock twitching and squirming in her hand.

"See how they rise and fall with my breathing, Teddy. You're making me a little excited, holding onto your stiff, manly penis while I have to show you my bosoms, my brassiere. It's a little embarrassing for me, Teddy, but I think I kind of like it."

Teddy's heavy breathing was also very noticeable.

"But, you mustn't touch them, Teddy." She clenched him extra hard and tugged as she said, "That would be a bad, bad boy." She let go of his stem and just circled the top of the head of his cock with the palm of her hand, breathing deeply, watching him watch her breasts rise and fall.

"What would your mother think, Teddy, if she knew that you were playing with your doctor's breasts?" Dr. Lowenstein often used role-playing techniques in her clinical treatment. She would have the patient pretend that he was a significant person in his or her life. This approach was often useful in generating empathy for the other person as well as drawing out hidden conflicts the patient might have. In this instance, though, she wasn't too sure why she raised this association.

"I don't think she would like it," he admitted, his face clenched with urgency and frustration.

"No, no, I imagine she wouldn't. That would be a very bad boy, touching your doctor's boobies." She again grasped the shaft and stroked her hand up and down its length. "Such a bad, bad boy, but, then, she probably wouldn't like you even to be masturbating, would she."

"No," he gasped.

"Squirting your dirty, nasty, cum all over the floor, the bed spread, your clothes, wherever you happen to spend. Such a dirty, nasty boy." The contrast of her disapproval, the naughtiness of it, with the reality of what they were doing was so very intense for Teddy.

"No, Teddy, you can look, but you can't touch." She leaned in closer to him, pressing the lace of her bra, the softness of her full breasts, against his arm. She lightly flicked his earlobe with her tongue, and whispered, "Maybe if you're a good boy, Teddy, and squirt for your doctor, I will let you touch them."

"Oh doctor," he again pleaded, feeling the internal pressure of the inevitable rush of his orgasm but, once again, Dr. Lowenstein squeezed hard, very hard and steady, just below the crown.

Teddy felt like his balls were about to burst. He had never waited this long to cum before, at least when he was by himself.

Dr. Lowenstein let go of his cock and lightly drew her index finger around and around his soft, engorged, purple bulb. "It's so smooth, Teddy, and so red. You must be very proud of it."

Teddy could feel the urgent pressure rising.

"I bet Penny likes to lick it, doesn't she, Teddy."

"Yes, ma'am," he replied, watching as his cock twitched with her delicate titillation.

"Oh my, yes, I'm sure she does." She pouted coquettishly as she said, "I think I'm feeling a bit jealous of your little girlfriend, being able to wrap her warm, sweet lips around such a manly cock head, drawing it into her mouth." She firmly grabbed the shaft, and moaned, "Would you mind terribly much if I put it in my mouth, Teddy?"

"No, doctor, no ma'am." That would be a great way to finally cum.

"Oh but no, Teddy, you know that would be wrong. That's why I'm your doctor, Teddy." She was again sliding her clenched fist up and down the shaft. "You have all of these dirty thoughts and nasty impulses. Wanting your doctor to lick your hard penis. Why, my goodness, all she is wearing is her bra and panties, and you want her to kiss your penis too? Such a very bad boy with all sorts of nasty ideas, but I won't let you act them out, Teddy. You're safe with me."

"Thank you, ma'am," his voice distorted by his gasping for breath.

"Yes, we don't want you to do anything inappropriate now, do we?"

"No, ma'am."

"My goodness, Teddy, my heart is pounding. My nipples, Teddy, if only you could see my nipples. They're so very hard." She was being seductive but she was indeed becoming quite excited. The office was feeling very warm despite wearing only her undies, and there was considerable warmth, even heat, between her legs.

She sighed deeply and brushed her erect nipple back and forth against his arm. "Teddy, you're such a bad boy, you're making your doctor all hot and bothered."

"I'm sorry, ma'am, I mean, doctor."

"Oh, that's alright, Teddy. I guess it's only natural for a lady to get a little aroused, stroking such a big, masculine cock in her hand." She used more force and speed. "I want to do so much more with your hard cock. I want to feel it against my nipples, my bottom, my lips. Can't I please just kiss it once, Teddy?"

Teddy didn't know what to say. He was in a deliriously confused state. He was so very close, and he wanted to cum so bad.

"But, we must be professional, Teddy," Dr. Lowenstein said.

However, her fist was now working harder on his cock. The room was filled with the sound of her fist slapping up and down his shaft. "But, you can cum for me, Teddy, I don't mind. In fact, I want you to do it." She pounded furiously with her fist, jerking him fast and hard. "I want to see your white, hot, sticky cum, gushing for me, Teddy, squirting out all over, all over the floor, dripping down my hand. Won't you do that for me, Teddy? Please?"

"Doctor!" he gasped, and his gism gushed forth. She not only let it happen but she continued to pound on his dick as his cum shot out, spewing across the floor in big white ropes and gobs, shooting up and out from him into the air and then raining down on the towel draped across the carpeting.

"Good boy!" Dr. Lowenstein, exclaimed. "So much cum for such a young man." She continued to praise and extol his blasts as his body jerked and spasmed. He was not himself watching his gushes, as his eyes were closed with the rapturous feeling of his orgasm, waves of intense physical pleasure sweeping through him, each wave like a fainting spell swiftly engulfing him and then followed by another.

Dr. Lowenstein though was watching, in part to be sure that he didn't get any of his cum on the carpeting, or her nylons and shoes, but also simply because she was enjoying the sight. He really did have lots of cum, and he was shooting with the energy and force of a healthy young man, something that she hadn't seen for quite some time. He had shot off pretty darn good during the first session, but this was clearly with much more intensity and thrust. It was like she was holding onto a jammed hose, blasting bullets and streamers of cum across the floor.

When he was done he fell back into the couch, exhausted, his balls aching with the release of such a huge load with so much intense pressure.

Dr. Lowenstein leaned down and picked up the towel, being careful not to let any of the gobs and pools of cum drip off, which wasn't easy as it was pretty thoroughly soaked with quite evident puddles. She wiped off her hand on a clean, dry corner and then handed it to Teddy to clean himself.

She then felt a wave of insecurity, doubt, sweep through her. With the therapeutic exercise over she was reminded again that she was sitting next to Teddy dressed only in her bra and panties. They were no longer lost in the sexual moment of passion. Now she just felt like a doctor whose dress somehow fell accidentally to the floor. She quickly got up and took her blouse from the desk to cover herself. It was still though a pretty sexy, alluring sight, as her nylons and panty clad hips remained exposed, and the sight of her trying to protect her modesty with just her silk blouse was rather endearing. "Um, well, Teddy, alright then, we can pick up where we left off next week."