This story is placed within the anal section as it concerns anal sex. If you don’t enjoy stories involving anal sex then you really shouldn’t read this story. You will be wasting your time. But, if you do like such stories, then I hope you like this one!.
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“It was a pretty strange dream.”
“Dreams are the royal road to the unconscious, John. It can be very helpful to explore them. Please, go ahead.”
This was just the second session with Dr. Lowenstein and she was still conducting her assessment of John’s problem. Dr. Lowenstein was a certified sex therapist working with students at Templeton College (e.g., see “There must be something wrong with me” and “Cosplay”). John came to her because he was having erectile dysfunction problems. He would at times have difficulty getting an erection and at other times have difficulty sustaining his erection.
It didn’t happen all the time. In fact, it didn’t happen most of the time. Much of the time he was fine. But, it did happen frequently enough to trouble him.
Fortunately, or unfortunately, he did not currently have a girlfriend. That was fortunate in that his problem was not disrupting or harming a relationship. It was unfortunate because he didn’t have a partner with whom to work out the problem. And, well, of course, it is always unfortunate not to be within a relationship. And John had no intention of dating until he got over the problem.
The problem became evident simply through his evenings at masturbation. John did like doing that. In fact, he masturbated most every night. He would at times refrain for a few days, as he felt that he would then build up quite a head of steam, so to speak, for a really nice, special evening.
But, he began to have some difficulty. Sometimes he would have difficulty getting an erection started. He knew that as you got older you would begin to have some difficulty getting erections, but at nineteen? He felt considerably older than when he was in high school, but he was still just nineteen, a sophomore in college. No, it couldn’t be aging.
He then wondered if he was jerking off too often. Once a day is perhaps doing it too often. When he was in junior high he might do it twice in an evening (and perhaps even once during the same day). Those were good times. Perhaps he was indeed getting old, having cut back to just once a day. But he also noticed that the difficulty did not seem to be correlated with the amount of time off.
He then wondered if perhaps he might be gay. He got aroused thinking about girls. He masturbated to fantasies about girls: girls he knew or actresses he thought were hot, or just girls of his fantasy world. He imagined them doing all sorts of things: slowly taking off their clothes, teasing him, fondling him, blowing him, letting him cum on their faces. All of that got him really, really aroused, except sometimes it didn’t. And, well into a masturbation episode he might just suddenly lose his desire and no matter how much he thought about the respective girl’s boobs, her cunt, her lips, he just couldn’t get his erection back.
So, he tried fantasizing about guys. But, that didn’t work. Much as he tried to think and fantasize about having sex with a guy, it just didn’t work. He would then switch to a pretty girl he knew and he very quickly became erect. It didn’t seem to be that he was actually gay.
He just couldn’t figure it out. He even started to have very restless nights, filled with all sorts of strange and disturbing dreams. He realized that he really needed to see a therapist so he made an appointment to see Dr. Lowenstein. The first session was devoted to gathering information concerning life history, his sexual history, his relationship history, and the history of his sexual problem.
It had been a difficult session for John, talking about all that personal stuff, particularly with a woman, and a woman as attractive as Dr. Lowenstein. She had absolutely gorgeous big grey eyes, dark lashes, long wavy auburn hair, sweet red lips, a delicate, thin nose, and a lovely, incandescent smile. He reminded John of Julia Roberts, with spectacles, and that was pretty darned nice. In fact, after the first session he had gone home to the dorm to masturbate thinking about her, about feeling her breasts, her sucking him off, and even having sex with her on her analyst’s couch.
It was a good session. It began with her explaining to him, “You know, John, doctors can have sex problems too.” She got up out of her chair and stood before him, unbuttoning her blouse. “I haven’t had sex in so, so long, John. It can be so difficult for a professional woman to find a man. I just need a little release, a little relief. You’ll help me, won’t you, John?”
As he stroked himself he thought about Dr. Lowenstein slowly taking off her clothes, standing in front of him dressed in just a lacy brassiere and panties, lifting up her big boobs for him, bending over to have him snuggle his face in those lusciously soft female pillows. He was getting harder and harder. In his fantasy she stood before him and slowly pulled down her panties, her eyes remaining fixed on his, smiling all the time as she watched him get more and more excited as she bent over, the cleavage of her brassiere opening up wider and wider, his eyes uncertain where to look, into her eyes, down into her cleavage, or at her hands drawing her panties down her thighs. She let them fall to the floor and stood back up straight, albeit using her hands to keep her modesty, hiding her cunt from view.
“John,” she asked, “Would you be willing to please your doctor, with your mouth? No man has ever done that for me before, and it would make me so very, very happy. I’ve always wondered what it would be like to have a man use his lips, his tongue, there on my, my….”
“Your cunt,” he said, in his fantasy.
The doctor covered her face with her hands in embarrassment, yet in doing so revealing to his eyes the sight of her womanly cunt. He was rather surprised, but pleased, to see that the doctor shaved herself. “You have no hair?” he inquired.
“Oh, goodness,” she said, her hands retreating back down to her cunt. “You’re not upset, are you?”
He was actually quite pleased, particularly if he was going to eat her out. He much preferred a shaved than a hairy cunt when doing something like that, although he had not in fact done it very much. “No, no,” he said, reassuringly. He took her hands and gently moved them aside so that he could see her again.
“Oh please don’t look,” the doctor said, again covering her face in embarrassment.
“It’s beautiful, doctor,” he said, in his mind, his fantasy, as he continued to stroke his dick.
It was indeed. He imagined the doctor would have a cunt as pretty as her eyes: smooth, white, and pure, a nicely intimate, petite pouch cut by just a small enticing slit. He leaned forward to place his lips against hers and, as he grasped hold of her womanly full butt his cock lurched and swelled in his hand. He stopped for a moment as it felt like he was about to cum, and he had not yet even gotten as far in his fantasy where he was actually fucking her.
He then started licking, sucking, and chewing on the doctor’s cunt and clit, all the while squeezing and pawing her soft, pliant buttocks.
“Oh my, oh my, oh my goodness,” gasped the doctor. She rested her hands on his shoulders, finding it difficult to maintain her balance, to keep her legs steady, as she apparently had never felt anything like this before. “This is so wonderful,” she sighed. “You’re so good at that, John. You make me feel so alive, so excited. Oh my goodness,” she exclaimed, with some embarrassment, “I’m getting so wet!”
She pushed him away, apparently realizing that she was herself getting close to cumming. “Please, I must have you. I must feel your, your….”
“Cock?” he answered for her, the inhibited, frustrated doctor apparently quite insecure about speaking so bluntly, so wantonly.
Her face turned red at his imprudent, bold language.
“Yes, yes, your, your penis. I must feel it inside me. You must have such a big, hard, stiff penis. Please, please let me see it.”
In his fantasy he undid his slacks and pulled out his cock, displaying it with some pride to the doctor.
“Oh yes, yes. Oh my goodness, it’s so impressive.” She blushed again at the sight. “I don’t know if I can take one that big in me.” John did not hold back on his fantasies. Why should he? It was his fantasy. It might as well be as good as he wants it to be.
She got down onto the floor, spread open her legs, and pulled her knees back against her chest, to offer herself in as open, inviting, and obscene manner as possible. “Fuck me, John, fuck the doctor with that big, hard, oh my, that, that, COCK of yours!”
But, then, John could suddenly feel the arousal, the excitement, suddenly dissipating, slipping away from him like air from a punctured balloon. His dick went limp, and he lay there confused, disappointed, and distraught.
He was now back for his second session with Dr. Lowenstein, lying down on her analyst couch, the doctor sitting in her chair behind him and to his right, where she was out of his sight, but he was fully within hers. Dr. Lowenstein was having him describe one of his recent nightmares for her.
“Well, um, I was trying to burrow through this tight, dark, cave, or tunnel. I’m not really sure now which it was. I guess it must have been a tunnel. It was really very frightening, so narrow, so tight, but the walls were so soft and squishy, not like any tunnel or cave I’ve ever seen. It was like I woke up buried alive and I didn’t know where I was and I was trying to squeeze and burrow my way through this cramped crawl space, trying to escape, trying to get out, yet it seemed like I was in fact going in deeper and deeper, but…”
He paused.
“But?”
“What?”
“You said, ‘but.'”
“But?”
“Yes, you said ‘but.’ But what?”
He wasn’t too sure he wanted to tell her all of the parts of the dream.
“You need to tell me all of the dream, John. It’s really quite important.”
He took a deep breath and told her the rest. “Yea, well, the weirdest part was that I developed this big erection. I mean, like, a really, really big one.”
“Yes, yes, very interesting,” Dr. Lowenstein replied, crossing her legs.
“It was so weird to be so frightened yet to have this really, big, hard….” He couldn’t say it.
She finished for him, “Cock?”
“Yes,” he shamefully admitted. “I mean, well, it was so big that it was making it difficult for me to squeeze through. It just kept getting caught. The tunnel was so darned tight, and dark, and I was getting more and more scared, yet more and more excited, getting harder and harder, swelling up really, really big making it even harder to get through the tunnel and then…I woke up.”
“Yes, yes,” Dr. Lowenstein replied, “very interesting, John, very interesting, indeed.”
“You think it means something?”
“Oh, I don’t know. I don’t know.” She knew full well what it meant but it was always best for the patient to reach his or her own insight. “What do you think, John?”
“It doesn’t mean anything to me, other than being just so weird.”
“Yes, well, did you have any other dreams this past week?”
“Yea, quite a few of them, all of them nightmares.”
“Tell me about another one.”
“Well, there was this other one in which I was sitting on this big soft white pillow. It was actually more like a giant round cushion, one as big as a room. But, it was outdoors. I was in this field, lying on this giant round, soft, white cushion, looking up at the moon. There was a full moon that night. I do like staring at the moon, don’t you, doctor?”
“The moon is a very wonderful symbol, John.”
“Yea, I was just lying there, admiring the big round white moon, and then, like, suddenly, I got this big hard-on. I don’t know why. All I was doing was looking at the moon and I got really sexually excited.”
“When you’re awake does that ever happen?”
John turned his head away to face the wall, away from the doctor, as he admitted, very, very shamefully, “Yea, actually that has happened, a couple of times.” He knew that must sound really crazy. “Does that mean something?”
“What else happened in your dream, John? So far it sounds like a very pleasant dream.”
“Yea, it was weird, ’cause then suddenly, well, not suddenly, slowly this hole opened up beneath me, just gradually, slowly, getting bigger and bigger, and I found myself being drawn down into this hole in the cushion, being slowly pulled in, or more like squeezed in. I tried to get out. I tried to hold onto the cushions, but they were so slippery, smooth, and soft. I couldn’t get a good grip, and I kept sinking down into this tight little hole, like I was being sucked into a cushion’s quicksand, and all the time my, my…” He again couldn’t say it.
“Your cock?”
“Yea, my, you know, my penis. My penis was getting harder and harder, and stiffer and stiffer, and it was so difficult squeezing it in, until eventually only my head was outside of the hole, just my head was poking out, and as it popped in I took a deep breath and felt like I was going to ejaculate, but I woke up.”
“Yes, most interesting, John, most interesting indeed.”
“You really think these dreams mean something, Dr. Lowenstein?”
“Well, sometimes they do, John, sometimes they do.”
“Yea, well, you’re the doctor. There’s this third one I remember. Do you want me to tell you that one too?”
“If you wish, John, if you wish.”
“Yea, well, in this one I was with this girl I know, Nina Hartley. I don’t really know her at all. She’s just this girl I know. Well, actually, I kind of like her, you know. Actually, I can’t really say I really like her, ’cause I don’t really know her. I would like to know her but, well, you know, I really don’t feel right about asking any girl out right now.”
“And what happened in this dream, John?” He was clearly demonstrating some resistance in talking about this girl.
“Yea, the dream, well, it started off fine. I was in fact, well we were in fact, making out, you know, kissing, and I had this….um.”
“Erection?”
“Yea, but, well.”
‘Tell me everything that you can remember about the dream, John. Each detail can be quite important.”
“Yea, well, it was, well, kind of weird, ’cause I like had this…erection, but it was, like, so much bigger than I had ever had before.” He turned his face back toward the doctor, although he couldn’t actually see her. “I mean it was gargantuan big, crazy big and, well I mean, like, it was so big I was thinking that there was no way she would be able to take this thing. Is that really possible, doctor?”
“Excuse me?”
“I mean, is it really possible to be so big a girl can’t take it?”
“Well, technically,” Dr. Lowenstein hesitantly replied, uncrossing and then re-crossing her legs, a warmth developing in her thighs as she imagined taking a really, really “gargantuan” one, “I suppose that it is conceivably possible that a boy, a man, could be too big, but the average woman can in fact take quite a big one, if she wanted.”
John felt like asking the doctor what was the biggest one she had ever taken, but he figured that might be too personal. “Yea, well, it was weird, I mean, like…” His voice quieted. “I’m not really that big,” he confessed, “and it was so strange to think that I would be too big, that it wouldn’t fit, and,” his speech accelerated, “and I really wanted this girl and she clearly wanted me. We were really going at it, but suddenly my erection just slipped away, and I had this big panic. What was I going to do now? What would she think? One moment I’m dying to have her touch me, down there, you know, and then the next moment I’m scared shitless that she will, ’cause then she’d discover that I didn’t even have an erection, and probably wasn’t going to get one. I thought of telling her that I didn’t want to go too far too fast, like as an excuse, you know, and then suddenly we’re in this field of rose bushes, like we’re surrounded by roses. That’s my favorite flower, a rose. Seems weird for a guy to have a favorite flower, I know, but for some reason I really like red roses. Pink ones are good too. Do they have brown roses? They really should.”
“A brown rose?” That did seem to be an odd association, an odd preference.
“Sure? Why not? Well, in any case, with the roses my erection returned like gangbusters and she had her hand down in my pants, feeling it, and I had my hand down in her panties and we were like feeling each other up but she had the weirdest, strangest, um….”
“Pussy?”
“Yea, like her vagina just felt so weird. Not right at all, not like one is supposed to feel. I mean like the mound was really abnormally large and round, like all puffed out cheeks, and, well.” He knew this was going to sound weird, but dreams can indeed be very weird, “you know, the crack, the slit, it actually wasn’t like that. There was instead a really large crack, spilling the cheeks of her vagina, and down inside there was just this rounded puckered tight curly hole, like all squiggly, and wrinkled, and dry, real dry, like she wasn’t excited at all.”
The doctor clarified, “A tightly puckered, wrinkled dry hole?”
“Yea, but I wanted to get in there so, so bad. My, well, my penis was so rock solid hard, and clearly way too big for that little thing, and the hole was just so tightly shut I was even having difficulty getting my finger in there. And then she took her hand away from my, you know…”
“Your cock?”
“Yea, she took it away, which was pretty disappointing, but she did that to reach down, with both hands, down into her panties, to grab hold of those big cheeks of her vagina to spread them open for me and, she said, ‘Fuck me, John, I want you to fuck me up my’ and then I woke up.”
They were quiet for a second.
The doctor asked, “Up her what, John?”
“Up her, you know, doctor, up her, you said it before…her vagina.”
“Are you sure, John?”
“What?”
“Are you sure that’s what she wanted?”
“Goodness, I think so. I mean she was spreading it open, and everything.”
He wasn’t getting the point of her question.
John pondered her question further. “Well, you know, in real life I don’t think Nina would, you know, want me.”
The root of the problem was obvious to Dr. Lowenstein.
“John, have you ever tried anal sex?”
“Dr. Lowenstein!” John was quite shocked at such a question. “I am not gay, Dr. Lowenstein. I already told you that.”
“Nobody is suggesting that, John, not that there is anything wrong with it. I was just wondering if you had ever tried anal sex, with a girl, for instance.”
“Goodness, no, Dr. Lowenstein, that would be, like, perverted.”
She didn’t answer him immediately.
“Wouldn’t it?” he asked again.
“John, what I think is happening is that your repression of your unconscious desires is blocking your conscious desires from being expressed. It’s really like something stuck in a narrow pipe. It’s hard at times for your conscious desires to push their way through when your unconscious ones are so constipated, blocking the way. You need to flush them all out. You need to discover your unconscious desires and expel them, purge them from your system. You need to ream out that unconscious.”
Well, that was a lot for John to absorb.
“Here,” the doctor offered, “let’s try a little psychodrama.”
“Psychodrama?”
“Yes, psychodrama. It’s a very standard psychotherapeutic technique in which you act out your sexual relationship difficulties. It’s a marvelous way to release and expose subconscious thoughts, fantasies, and fears.” Dr. Lowenstein was really quite skilled at psychodrama (e.g., “There must be something wrong with me”).
John had never taken any psychology classes so he really didn’t know what she was talking about, but that would hardly matter. She was the doctor and you should always trust your doctor. “Yea, sure, okay.”
“John,” she instructed, “sit up on the couch, facing me.”
“Alright,” he said, following her instruction but with some apprehension.
“John,” she asked, “Do you find me at all attractive?”
“Excuse me?”
“Don’t be shy, John. Just answer the question as honestly as you can. It’s all part of the psychodrama.”
An honest answer would be to say that she was incredibly pretty; in fact, beautiful: the big gorgeous grey eyes beneath the large round spectacles, dark lashes, long wavy auburn hair, sweet red lips, delicate, thin nose and lovely, shining smile. “Well, yea, sure. You’re a pretty darned attractive woman, Dr. Lowenstein.”
“Well, thank you, John. That’s very sweet of you to say so.” It might not be professional, but she did always like hearing that a patient found her attractive. Counter-transference feelings aren’t all bad, are they? “Have you ever thought about having sex with me?”
John could feel the blood flowing into his face. Why do psychotherapists have to be so insightful. He wondered if she even knew that he had already tried masturbating while thinking about her. She probably did. You really can’t keep anything hidden from a clinical psychologist. Well, he would at least try. “I, uh, um, no, no, of course not.”
It was a pretty pathetic lie. You didn’t have to have a Ph.D. to notice that lie. Dr. Lowenstein though smiled patiently. “John,” she softly explained, “transferential feelings toward your therapist are really very common in psychotherapy.”
He knew going into this that therapy would be difficult, but he hadn’t imagined anything like this, and certainly not so soon. He answered quietly, averting his eyes, “Yea, yea, I have, he confessed.”
“Well, that’s wonderful, John. That will be very helpful. Now, tell me what you have thought about, with me.”
Keeping his eyes averted he told her about the fantasy he had after their first session, although it felt more like a confession than simply a recounting. He didn’t though tell her all the details. He left out the part where he ate her out. He was a little embarrassed to tell her about that.
“You ate me out, didn’t you, John.”
“What?!” His face turned beet red. “How did you know?”
“A good therapist is intuitive about these sorts of things, John. And, besides, it’s a fairly common fantasy for a male patient.”
“It is?”
“Oh yes, yes, of course. It’s really only natural. Now, tell me, did you have an ejaculation?”
“No,” he said quietly, shaking his head in shame and embarrassment. His face grew even redder as he explained to her that he had lost his erection just when he was about to mount her on the floor.
“That’s wonderful, John!”
“What? Why?”
“You experienced your problem with me. It’s very common for patients to experience within therapy the problems they are having in their real lives. It’s all part of transference. But it can take weeks for the transference to become as strong as it is for you now. And, well, the fact that it has happened so quickly in your case means that we can now further assess, and even begin treating your problem within the context of the therapeutic relationship.”
“What?”
“Take out your penis, John.”
“What?!”
“Relax, John. This is a very common variation on a well validated phallometric assessment technique. There was in fact an article precisely on this technique published in the latest issue of the Journal of Anal Psychology.” It was really the Journal of Analytic Psychology, but the doctor preferred its abbreviated title. “Please, John, take out your penis, just so it’s outside of your pants, so I can observe its behavior.”
John could feel his heart racing, his hands trembling, his palms getting wet as he did as she instructed. It seemed like an awfully, awfully strange thing to do in therapy. She was a doctor though, and a sex therapist. She probably asks pretty much all of her patients to do this, at least at some point. Thank goodness he didn’t have an erection. Wouldn’t that be embarrassing. Imagine a doctor telling you to drop your trousers while you have an erection! He would frankly just leave the room rather than have something like that happen.
John unzipped his pants, reached inside, and struggled to get out his penis. He was wearing particularly tight briefs. Frankly, he didn’t even use the flap when he had to pee, it was so awkward to get to it. He wondered if clothing designers actually tested their products, discovering how hard it was for guys to get their dicks out through these little flaps.
Dr. Lowenstein waited patiently. She didn’t understand why he was having so much difficulty. It was likely another demonstration of unconscious resistance. She considered providing John with some encouragement but she felt that he would be able to do this on his own. He might be resisting but he would eventually have to show her his penis.
When John did finally get it out he was actually a bit disappointed that it wasn’t erect. It looked awfully small just flopped out of his pants, lying there limply. A good cock should be thrusting out, sticking out. It was like his just sort of fell out. It was anything but impressive. He was reminded of why he so much preferred male doctors over female doctors.
“Very good, John,” Dr. Lowenstein observed. It was actually better for the psychodrama for the young man to be limp. As she got up from her chair John appreciated the doctor’s long, shapely legs, stretching out from her short summer skirt. She was wearing a white blouse and a very pretty yellow skirt that was sprinkled throughout by all sorts of gaily colored flowers. She stood before the young man, so strikingly attractive, and leaned down in front of him, the cleavage of her blouse opening up for his eyes, her lovely perfume wafting across his nostrils. John could see down within the doctor’s cleavage to notice that she was wearing a yellow brassiere.
“Dr. Lowenstein,” John gasped, in panic and arousal, with the panic predominating over his arousal.
“Now, John, place your hands on my breasts.”
“Excuse me?”
“Just cup, or hold, whichever you prefer, each one of them in your hands, like you were going to pick out some nice fresh juicy melons.”
The doctor’s big grey sparkling eyes were now just inches from his, her nose almost kissing his, which was itself being intoxicated by the wondrous scent of her perfume. He reached up and grasped hold of each breast.
“Mmmmmmm,” Dr. Lowenstein sighed with pleasure at the touch of the young man’s hands on her breasts. An experienced older male would provide a more sensual touch, but there is also something inherently pleasing about the grasp of a very appreciative, inexperienced young man, and especially so when he is one of your patients, for whom you are providing such generously therapeutic help. Susan Lowenstein had always wanted to become a therapist, ever since she was herself an undergraduate in college, and it was at times like this that her commitment to her career, her devotion to her studies, were proven to be so worthwhile. She just loved being a therapist.
And, right now, John loved being her patient. Dr. Lowenstein had quite magnificent breasts. They were not humongous or anything like that, but they were clearly full, soft, squishy, and well rounded, and simply the fact that a beautiful woman such as her was bent over before him simply so that he could grab hold of them, squeeze and fondle them, was so darned wonderful. His dick instantly swelled without him even touching it, and for a moment he did not feel the least bit self-conscious about it.
The moment though was only brief. He did not have a particularly large cock. Plus he wasn’t really even fully erect. He was just clearly on the way to getting there. He had no expectations that the doctor would say any of the things he had imagined her saying the other night, in his fantasy. Plus, he was frankly unsure that he was even supposed to get an erection. What if she was offended?
But, she actually didn’t seem to take any notice of it. He wasn’t too sure if that was good news or bad news. It’s not particularly flattering to have a pretty woman be indifferent to your developing erection.
“Now, John, for this exercise I want you to tell me how aroused and excited you feel, on a scale from 1 to 10.”
“That’s easy,” he quickly answered, “a ten.”
“No, no,” she replied, smiling at his youthful enthusiasm, “leave yourself some wiggle room or, I should say,” waving her breasts back and forth in his hands, “swelling room.” She suggested, “Let’s make that on a scale of 1 to 100, but for this first one you can’t give me a score greater than 60. Now, close your eyes and concentrate on how your cock feels right now, as you’re holding my bosoms.”
He did as she instructed, letting himself bask in how sexy, how arousing, how exciting it was to be grasping hold of the doctor’s soft breasts. He could feel his dick swelling further. “Well, okay, this is a 60, ” he finally said, “but it’s really a lot greater than that.”
“Well, we’ll just see. Now, that’s enough of that.” She edged his knees apart, stood up straight and stepped up in between his legs. She reached out for his right hand and brought it right to her crotch, pressing it firmly against her mound.
If she wasn’t holding onto his hand so tightly John would have quickly removed it. It just seemed so wrong, so inappropriate, to be grasping a woman’s cunt through her skirt. And, this wasn’t just any woman, this was a really very attractive one, and the university’s psychologist no less. But, that’s precisely also what made it so appealing, so exciting, so thrilling.
“Alright then, John, what is the level of your arousal meter now?” Dr. Lowenstein asked, thrusting her cunt hard into the grasp of his hand, encouraging him to get a real firm, intimate grip on her cunt. “Close your eyes and think and feel how your hand is grasping my, um, my…” She hesitated herself in saying it. She had by now worked with many patients, but there was always a bit of self-consciousness in crossing this line with a young undergraduate student. “My cunt.”
John could not get as good of a feel of Dr. Lowenstein’s cunt as he would like, having to grope it through two layers of clothing. At least though her summer skirt was quite loose. This made it a lot easier than if she had been wearing a tight business skirt. The gaily colored skirt was in fact quite pretty but its prettiness was not what was on his mind now. His mind was on how her soft womanly mound felt through her skirt and panties. He felt he could even feel a bit of her lips and certainly warmth emanating, radiating, from inside her skirt, and feeling his dick as well swell and stiffen even more, perhaps now just about at full strength. “Eighty,” he suggested, feeling though that he could have really gone even higher.
“Alright then, you can take your hand away now, John.”
He quickly withdrew his hand. “Oh yeah, sorry,” he said, embarrassed over the fact that perhaps he should have known that himself, not wanting her to think that he was letting his hand linger there out of any prurient interest of his own. This was all just a doctor’s laboratory exam, after all. Still, it was pretty nice gripping the doctor’s cunt through her dress.
The doctor smiled at the young man. It was understandable for the patient to take a little extra feel during this procedure. One needed a bit of flexibility in the usual therapeutic rules and mores when conducting sexual psychodrama. And, besides, she did like feeling the young man’s hand there herself. There was something that was so enjoyable, so pleasing and fulfilling, in experiencing a youth’s enthusiastic interest in your body.
She took hold of both of his hands, stepped even closer to him, the front of her dress, her cunt, just inches now from his face, and brought his hands around her body to place them firmly on the soft, round, cheeks of her butt.
“Oh my goodness!” John instantly exclaimed. It was like an electrical switch had been turned on, a sudden surge of power, arousal, coursing through his body, energizing his very being with a lustful sexual ecstacy. He squeezed and pawed the doctor’s wonderfully firm yet pliant derriere, his dick swelling quickly to its fullest capacity, twitching in the air like a divining rod that had discovered buried treasure.
“What’s the score now, John?” The doctor inquired, but she knew the answer just by the expression on his face, and the groping of his hands on her butt.
John gasped, “Ninety easily, a hundred really, maybe 110.”
It wasn’t perhaps the most objective form of phallometric measurement but it was quite revealing. The doctor let the young man’s hands linger on her bottom, feeling him explore her curves, squeezing and caressing her cheeks. She felt like pulling his face into her crotch, to rub and caress her there as well, but she knew it was important to maintain a professional demeanor and poise. Crushing the boy’s face into her cunt would be going a bit far, at least at this point. She would certainly enjoy it, of course, but as a professional therapist Dr. Lowenstein would always maintain appropriate professional boundaries with a patient. This was especially important in sex therapy.
She did though eventually reach back with her hands to remove the boy’s hands. But, she did it so she could step back and observe John’s reaction for herself. “John, what a very lovely cock you have. Yes, you will make a girl very happy with this someday, and I suspect probably soon.”
It wasn’t what he had fantasied her saying the other night, but it was still a plenty darned good compliment, particularly from a doctor. A good prognosis from a doctor is always well appreciated. “Thank you, doctor,” he smiled in return.
She then turned around and bent over, presenting her bottom to John, to his hands, and to his face. “There you go, John. You can get a much better appreciation this way.”
John felt like he was a boy at Christmas. No girl before had ever presented her butt this way to him. He hadn’t even done it from behind. He never thought a girl would like doing it that way. It just seemed so animalistic, so demeaning, for her to get on her hands and knees and stick her butt up like that for him, presenting herself to him like a doe, a dog, in heat. He now realized how so terribly sexy that position would be. The doctor’s bottom looked so round and full, like a big pumpkin ready to be carved.
The doctor said, softly, “Lift up my skirt, John, and have a peek.”
His eyes widened in shock, and lust. “Really?”
“Oh yes, John. It’s very useful in psychodrama to act out, bodily, in treatment, one’s anxieties and impulses. You can often work through conflicts and issues through the psychodramatization exercises.”
John could feel his heart pounding. He was even feeling a bit lightheaded, a bit faint. He reached for the hem of the doctor’s skirt, and slowly pulled it up.
Dr. Lowenstein was wearing white nylons, which accented well her shapely legs and thighs. John soon discovered that they were being held up by a matching white lace garter belt and straps attached to the comparably lacy nylon tops. He then undraped the buried treasure: Dr. Lowenstein’s lusciously full round bum, wrapped tightly in her yellow bikini panties that failed to fully cover the rounded, cupped, bottom halves of her cheeks, leaving them to poke out from her panties like scoops of upside down ice cream. Her panties were themselves really quite lovely: yellow with little gaily colored tiny flowers scattered about, matching well her skirt, which John draped over her back, opening entirely up to view the pantied bottom of Dr. Lowenstein.
Dr. Lowenstein bent over even further, wrapping her arms around her partly bent knees to give her bottom an even rounder, tighter, and fuller presentation. A bottom presented in this manner was so provocative, so fetching, so inviting. It looked so big, so curved, so orbed. The shape was even a bit like a heart, much fuller and wider in the curves at the top, and coming to a V right at the pouch of her cunnie, which was itself poking out so invitingly. John’s eyes though were fixed on the doctor’s round fanny cheeks.
“Pull my panties down, won’t you please, John?” She gave him a little wiggle of her bottom for encouragement.
John’s mouth went dry as he reached out again, this time for the waistband of the doctor’s panties. She was wearing her panties on top of her garter straps and so John could pull them down off her bottom without undoing her garters. It felt to John that his cock was going to stretch right out of its skin as the butt naked skin of the doctor came slowly into view.
It was indeed a heavenly moon, and John recalled his fascination, his enjoyment, with gazing at the moon, even to the point of obtaining an erection. Perhaps the doctor was right, perhaps there was some sort of meaning to his dreams, and perhaps he was staring at it right now.
He let the panties fall to the floor once they reached the doctor’s thighs. He could not pull his eyes away from the crack of the doctor’s ass. It seemed to have him hypnotized, mesmerized. It was so enticing, so inviting, so suggestive.
The doctor, sensing a potential breakthrough, unclasped her hands and reached back to spread open her cheeks, opening up to the boy’s lustful gaping, gawking eyes, her puckered rosebud.
“Roses,” John said.
“Excuse me?” Dr. Lowenstein inquired, looking back at the young man as she continued to spread open her butt cheeks.
“Roses are my favorite flower.”
“Yes they are, John. I wonder why.”
“I think I know,” John replied, staring at the doctor’s rosebud, his cock feeling like it might ejaculate without him even touching it.
Sometimes it can take days, weeks, or even months for a psychotherapist to guide a patient to an insightful revelation. One typically needs to carefully hint and suggest, but never confront too early, as the patient may only retreat deeper into a safer repressive cocoon. But, few clinicians are as skilled or as innovative as Dr. Lowenstein, who simply had to spread open her butt cheeks and display her asshole to the patient to help him discover his epiphany.
“And, what would the reason be?” She wanted her patient to fully express his insight.
John said quietly, softly, his realizations slowly sinking in, “I think it’s that I really like girl’s anuses, or at least, I mean, well…I want anal sex.”
“Yes, John, I think you’re right,” the doctor replied with considerable understatement. She could have told him that she knew it all the time, but it was best to have the patient feel that the insight was his own, as he will then own it and more likely keep it. She added, softly, almost whispering as she looked back at him, “Touch it, John, with your finger.”
“You’re kidding!”
Dr. Lowenstein smiled, “Psychotherapists don’t kid, John. Go ahead, touch the doctor’s rosebud.” She even squeezed her sphincter a few times. “See, it’s winking at you, flirting with you, calling for you in her own special way.”
John took hold of his cock with his left hand, squeezing it as he cautiously, breathlessly reached out with his right to gently lay the tip of his finger directly onto the doctor’s butt hole.
“Mmmmmm,” the doctor sighed with pleasure at the feel of the boy’s prudent touch, and her anus twitched with the tingly ticklish sensation of his finger.
John recalled his third dream, of the girl, of Nina, as he touched what he thought in his conscious mind was her cunt, which he now realized was her anus: all dry, wrinkled, and puckered. He had never felt anything so mysterious, so alluring, so disturbingly heady. It was comparable to the first time that he had touched a girl’s naked breasts, and, surprisingly so, even better than his first touch of a girl’s naked cunt. John boldly asked as he gently felt the curves, wrinkles, and ridges of the doctor’s pretty anus, “Can I stick my finger in it?”
Dr. Lowenstein smiled. It always felt so good when significant progress was being made with a patient. Her feelings might be biased somewhat by his pleasing caress of her butt hole, but it was apparent that John was breaking through his repressed desires, and was in fact even beginning to express and assert them. But, she also knew that there was still more work to be done and this was not the right time to simply give in to his impulsive desire. “Well, doesn’t a girl deserve a kiss before you stick a finger up her butt?”
“Oh yeah,” John replied, “sure, I’m sorry,” feeling like he was waking up from a hazy dream, and realizing how ill mannered he had just been. He certainly didn’t want to sound like he was disrespectful of girls, particularly to his therapist, herself a woman, although it did seem awfully weird to kiss your therapist, and to do so in order to stick a finger up her butt.
But, he soon discovered it was even weirder. John waited for Dr. Lowenstein to turn around so that he could kiss her, but she just stayed in the same position, presenting to his eyes her puckered winking asshole.
“I’m waiting, John,” she intoned.
He then realized. She meant for him to kiss her on her butt hole. Whoa! This was one curious form of psychotherapy but, surprisingly, he was not repulsed by the thought. Not at all. In fact, on the contrary, he stroked his dick as he contemplated it, and he squeezed his dick as he leaned forward to plant his lips on hers, equally puckered as his own.
“That’s a good boy,” Dr. Lowenstein complimented her patient as she felt his lips planted on her butt hole, and then brought her cheeks together, squishing his face within the cheeks of her butt.
She couldn’t wrap his face, his head, nearly as fully as she could with her breasts, but it was still plenty cool for him, his face crushed within the soft pliant cheeks of his pretty therapist’s butt as he repeatedly kissed her arse hole. He was now reminded of his second dream, when he was being drawn down into the soft cushion, sucked down inside, and he slipped his tongue out through his lips to tenderly lick the doctor’s anus.
“Very, very nice, John,” Dr. Lowenstein softly sighed. She so much enjoyed having her asshole licked, and not many guys will do that. Actually, she still wasn’t dating anyone, and her sex life was largely limited to her clinical practice. She had established a fairly substantial clientele, but licking her anus was not currently a prescription for any one of them, so this for her was a really special treatment session.
She allowed herself to enjoy the licking and lapping for sometime. It felt like a puppy thirstily lapping at an ice cream cone on a very hot and dry day. She could not help but to wiggle and squirm her butt as John tongued and rimmed her pinkish brown hole.
John was so surprised at how much he enjoyed it. Prior to treatment he would have been repulsed by even the thought of what he was doing and, yet now, within just his second session of psychotherapy, he was feasting on the asshole of a woman, stroking his cock with delight, which he quickly stopped though as he felt himself getting close to cumming. His balls were beginning to ache with the desire, the need, to ejaculate, but he knew he should wait for that until this evening, although he may in fact go right back to his dorm room after this session to take care of himself, thinking about tonguing the doctor’s asshole as he jerked himself off. This was actually much, much better than the fantasy he had himself constructed after the first session.
But, he withdrew his lips from the doctor’s butt to ask, “Doctor, am I some kind of pervert or something. I mean, will I always have trouble with normal sex?”
Dr. Lowenstein had to first catch her breath before she provided her patient with the helpful guidance and instruction he was seeking. “No, no, not at all,” she responded, looking back at him and speaking in a professional, confident voice, still holding wide open the cheeks of her ass, “the release, the expression, of your normal desires were being plugged and clogged by your repression. With its expulsion, its release, the path is open for your usual, your more common impulses and desires, to come forth. You will be fine after a few cathartic expunges of your pent-up, repressed anal needs.”
It was a bit clinical, or perhaps it just felt odd to be so didactic while holding open her asshole to the boy. But, any competent therapist must be flexible in her technique.
John felt relieved. In fact, he was ecstatic. Not only would he no longer have erectile dysfunction problems but he had discovered a new source of sexual pleasure. He would now have his butt cake and eat it too. “Am I now alright then?”
Dr. Lowenstein let go of her butt cheeks, closing the curtain on her tight pink cave, much to the disappointment of John. She had said something about further catalytic expunges, or something like that, hadn’t she? He didn’t really want to end treatment now. Amazing to think that a patient would actually want psychotherapy to continue.
Dr. Lowenstein stood back up straight, her skirt falling back over her bottom. She stretched her back a bit as she had been bent over for quite some time. She wasn’t as young as she used to be. She did not answer the young man, not immediately. She stepped out of her panties and strode over to her desk, feeling the boy’s eyes following the swaying of her bottom beneath the thin loose cotton skirt.
When she got to the back of her desk she bent over it, to reach all the way over to the front drawer, and pull it open. It would have been easier to have just walked around the desk, but she wouldn’t then have been able to let John admire how her skirt fell so nicely across the curves of her bottom. She even took her time rummaging around the drawer for what she was looking for, her bottom wiggling and squirming before his eyes as she struggled to find it.
John grasped his cock but he didn’t stroke it. He didn’t dare take the chance. Imagine cumming all over the doctor’s nicely carpeted office floor. That wouldn’t be too good.
Dr. Lowenstein stood back up and turned around to face the boy, an understanding smile on her face, as well as a pleased one. He looked so cute, so endearing, clutching his erect cock like it might escape if he let go. She could see that he desperately wanted to jerk off, but knew that he couldn’t, or at least shouldn’t. It wouldn’t be therapeutic. No, his treatment was not yet over.
She stepped away from her desk, again turned her back on the boy, and got down on her knees. She looked back at him over her shoulder, smiled flirtatiously, and lifted up her skirt, past her white nylons to the rounded curves of her naked rump. “Time for your first expunging, John,” she said coquettishly, and got down on her elbows, lifting her naked bottom up in the air, arching her back, and spreading out her legs. She again looked back at him and said softly, “Come and fuck a pretty woman’s butt, John.” It was perhaps less than modest to put it that way, but it’s narcissism only if it’s not true and, besides, it sounded so nice to John.
He got up onto his feet, feeling a little wobbly and shaky, and strode over to the upraised, naked ass of Dr. Lowenstein. Why did he deserve such a prize, such a treasure? He certainly hadn’t done anything to deserve it. But, actually, it wasn’t really a reward. It was a prescription, a necessary medicine to swallow, and one that would taste very, very good going in, going down.
He wondered if he should take his pants off. It would be easier to fuck her that way, but she hadn’t told him to disrobe. He didn’t want to presume anything, or to do anything that might be disruptive to his treatment. And, besides, perhaps it was best to keep as much clothes on as possible, in case somebody suddenly arrived at her office, like her next patient maybe, coming early. As he got in between the doctor’s legs he glanced at the door. He hadn’t locked it when he came in.
“Don’t worry, John,” she said, looking up at him, past her upraised bottom. “My next patient isn’t due to arrive for at least ten minutes. You have time to finish your session.”
Ten minutes? She clearly wasn’t expecting him to last very long but, then again, he would not have been terribly surprised if he came just walking over to her. Still, it would seem like they didn’t have much time to waste. He got down onto his knees behind her, his heart pounding with anticipation, and excitement. He couldn’t believe what he was about to do. He was actually going to fuck a woman up her ass and, as she said, a pretty woman at that, with a very lovely round white butt.
Dr. Lowenstein reached back to hand to him what she had retrieved from her desk: lubricant. “You should always use something when you put it up a girl’s butt, John. Sometimes they can take it without much, if any, but it’s really best to use it.”
He just nodded. He felt a little silly not thinking of that himself, although he had gotten her pretty wet with his tongue. Nevertheless, he accepted the lubricant, squeezed out a dollop and, as she again opened up the crack of her ass, applied it to her anus. However, he did hesitate. He wanted to first admire the sight of her puckered asshole, at least for a moment.
The doctor wiggled her butt at him. “John,” she said, “hurry up now, we don’t have a lot of time.”
Apparently they went from plenty of time to little time, although he suspected that it was just the expectant position she was in, her bottom poking up, her cheeks spread, her rosebud shining in the light of her office lamps. She must feel a little embarrassed, a little exposed. He applied the wad of lubricant to the pretty doctor’s anus.
Dr. Lowenstein sighed with pleasure at the feel of his warm, and now slick and slippery, finger, caressing her anus, working the lubricant into her skin. “Poke it up inside, John, make sure you get it good and slippery.”
John squeezed out another blob of lubricant onto his finger, and used this wad to work his finger down into her ass. He was surprised at how tight she was. Of course she would be. An asshole needs to be very tightly sealed. He marveled at the thought that his dick could actually fit through there. It was difficult to imagine. He worked his finger in and out of her asshole, feeling around inside her rectum, deep inside where no finger should be, certainly no finger of a boy. He wondered if he could, if he should, tell his friends about this. Of course in doing so he would be revealing that he was in therapy, and he would then have to explain why. But, still, what young man wouldn’t want to tell his friends that he had been sticking his finger in and out of the pretty Dr. Lowenstein’s butt. Well, actually, nobody would really believe him. How could they? Nothing like this ever happens in real life.
“Your finger feels so nice, John,” Dr. Lowenstein purred. It did indeed. It was like a wiggly little snake was playing around within her anus and rectum, teasing her, tickling her, exploring her. It felt so naughty, so dirty, but that’s why it also felt so sexy.
John realized that time was slipping by and he slipped his finger out, making a little popping sound as he did so, causing the doctor to giggle. He put a final dollop of lubricant on the head of his cock, the thick round purple bulb that was to somehow jam its way past her tight anal sphincter. He got up higher on his knees to position the swollen plum at the entrance to her rectum. He leaned forward into her butt.
Dr. Lowenstein’s eyes widened at the pressure. The head of John’s cock was clearly much larger than his finger. She grunted with the forced compression onto her clenched sphincter. But, she was a professional, a skilled therapist. A layperson would have resisted the blunt intrusion into her rectum, particularly under the pressure of time as well as cock. But, Dr. Lowenstein calmly relaxed her sphincter to let him in.
It wasn’t easy though for John to get it in. His dick did not slide in like his finger. But, he could not take his time, as the seconds, the minutes, were ticking away. He used his weight to help force his way in, and suddenly he felt the doctor’s sphincter give way. Her butthole opened up and the head of his cock plunged all the way in, disappearing from sight down into her dark, tight rectum.
“Unnng,” Dr. Lowenstein groaned. She felt so distended, packed, clogged, and stuffed. “Wait, wait a second, John.” She had to have a moment to get used to it, to adapt to the fact that her rectum was so thoroughly engorged.
That was fine with John. It was nice just to pause and treasure the moment; as his mother always said, to stop and smell the rosebuds, or at least something like that. All he could see was the stem of his dick; the round bulb of the head being tucked inside. And, it felt so cool. It was such a tight fit, like there was a thick rubber band clenching his shaft, with the head itself cushioned by receptive soft tissue. And, perhaps the best part was psychological: the fact that his cock was actually inside a woman’s butt. It seemed so wrong, so filthy, so nasty to do something like this. Not too many men, and perhaps even fewer women, would do such a thing. But, the fact that it was so lecherously raunchy made his cock swell even thicker, plugging her hole even more tightly.
Dr. Lowenstein grunted. “John, your cock feels so fucking big up my ass.”
It was music to John’s ears. He slowly began to push in farther, but not very far, and he then pulled back. He repeated this tentative movement again and again, each time going in a bit farther. It wasn’t easy. She was so awfully tight. But, he enjoyed so much the feel of her rectum rubbing and massaging the head of his dick as it worked its way in and out of her ass. He also enjoyed the sight of it entering and leaving her so fully distended asshole, down deep between the pale womanly cheeks of her soft round derriere.
John began to more rhythmically slide his cock in and out of her ass, never pulling out too far or moving in too deep. He certainly didn’t want to let it get all the way out, although there really wasn’t much chance of that, because when he got close to fully pulling it out he again felt the resistance of her sphincter, this time acting against his departure, his escape, as if she was trying to hold his cock captive inside her ass.
Dr. Lowenstein was giving him nice squeezes with her sphincter, not to resist him but to instead hug him affectionately. After all, he was making such good progress in treatment. This was a very big step for him. And, it did feel as well pretty darned good to the doctor. A good butt fuck was a nice change of pace. A man’s cock, even a young man’s cock, felt so abnormally big when it was up her ass, like she was again getting fucked for the very first time. She reached back beneath her body to get to her clit, to rub and massage it as the boy worked his cock in and out of her rectum.
She roughly diddled her clit as he began to stroke short rapid thrusts with his hips. He was now giving her asshole a good quick fucking, not too deep but still rather bestial, like a dog mounted on its lover, plunging rapidly to get a quick release.
John knew he wasn’t going to last any longer and he wanted to fuck her as hard as he could before he came.
Dr. Lowenstein at first tried to meet his frenetic thrusting with her own bottom bounces, but she could not keep up. She then just held her butt still, and let him fuck her derriere like a passive doe, giving her butt to him for his to fuck as he saw fit, but all the while squeezing tightly on his cock with her sphincter to maximize the sensation.
John’s plunges quickened in pace, lost in the wonder of her rectum wrapped tightly around the head of his cock as his shaft was grasped by her sphincter. He wanted to cum now, wanted to release his stuff deep into her bowels. And, then, he felt his legs tremble with the inevitability sweeping through his loins. He pushed down in deep, as deep as his cock would go, his abdomen pressed against the soft cushions of the doctor’s ass, his cock stuffed deep down inside and he let it cum, the first wave of cum jettisoning down through his shaft with substantial force, bursting out from his cock deep into her rectum. It was like his cock was a plugged hose that finally had forced out an unconscious impediment and was bursting and gushing forth its insights.
Dr. Lowenstein felt the twitching and pulsations of the young man’s cock through her sphincter muscles, and she closed her eyes, and rested her head on her arms, to enjoy the sensation of him spurting his cum deep down into her ass. She could feel the young man’s shaft twitch and jump with each ejaculation. She thought she could even feel the liquid mounting in her rectum, like she was getting a rather obscene enema. But, it was such a satisfying one. It was such a concrete, vivid demonstration of therapeutic success. She squeezed and milked his cock with her sphincter, drawing out more and more of his gism.
John, gasping for air, leaned forward over the back of his doctor, gripping and bracing himself with his hands on her hips, basking in his exhaustion, his exertion, his bliss. He breathed a sigh of deep relief. It had felt so good, and he now felt so wonderful. He felt cured, self-actualized, self-realized. He smiled with profound satisfaction, and slowly pulled his cock out, the head giving a pop as it was released through her clenched sphincter. Her anus stayed open a bit after he removed it, gaping at him, showing him the globs of cum down inside her rectum, then slowly shut once again.
The doctor squeezed her anus tightly shut, holding his cum inside. They now had very little time. She pulled some sanitary handy wipes from her desk. She always had an ample supply. She helped John clean himself off and then get his slackening penis back into his pants. Only then did she retrieve her own panties and pull them back on.
As she did so she reiterated to John the importance of his insights. John was surprised at his prior inability to see, to know, what must have seemed so obvious to anyone else. But, the doctor explained that what might be obvious to others can often be obtuse to the individual. It’s a psychological blind spot, and being blind to its presence he was also blind to its effects. It was how the unconscious worked.
As she opened the door to her office, to shake his hand as he left, standing there was her next patient.
“Dr. Lowenstein, hello, it’s me, Adam. I hope I’m not early,” he said, seeing what must be her prior patient now just leaving. He sure hoped he hadn’t disturbed her.
“No, no, please, we ran a little late. Please, do come in.” She said goodbye to John, reminding him of the time of their next session, and then turned her attention to Adam, which wasn’t that easy, her rectum being filled with John’s cum.
Adam was having sleep troubles, his nights repeatedly disrupted by quite disturbing dreams, involving the eating, or more like gorging, on clams, as well as getting his face smacked and splattered with sloppy fish pies, and the weirdest of all was munching on a thick furry carpet. Dr. Lowenstein knew that she would have to use a very different approach with Adam. Well, not entirely different.
The session turned out to be a bit awkward though, as she was tightly squeezing her sphincter throughout to avoid having an accident in her panties. She had to retain John’s slippery gism up her rectum throughout the session, and it was a bit uncomfortable, a little awkward, a little risky, but that’s what also made it rather enjoyable. It turned out to be a very nice session indeed.
As John left the building he felt so wonderful, so good, so optimistic but, then, it hit him. What girl would share with him such pleasure in anal sex?