The Hiltop Ch. 03

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He shares secrets & masturbates for his role-playing "nurse".
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Part 3 of the 3 part series

Updated 06/07/2023
Created 08/26/2015
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The young woman had made good use of the young man's semen-encrusted underpants she had absconded with after their first meeting on the hilltop. He had just masturbated for her and she used them to clean up his huge mess. She knew she'd keep them to help her relive that incredible experience, and the crusty, yellowish stains never failed to excite her. (She hoped the well-used panties she left him in exchange had been similarly useful).

It was during one of these sessions that she hatched her current plan. They'd shared an extremely intimate conversation on that hilltop during which he revealed that his most potent fantasy was to be controlled and humiliated by a female authority figure. If her plan went well, she'd give him an experience he'd never forget. She'd invited him to dinner, but the first course was definitely not on the menu. She thought the nurse's hat was a nice touch. Nevertheless, she was a bit nervous (as well as excited) as she opened the door.

"I'm glad you're on time for your examination," she said using a professional tone. "Please follow me."

She led him to her spare room which had been converted into a makeshift doctor's office and instructed him to take a seat on the "examination" table. She was dressed in a white skirt and a polo shirt with no bra. She knew he adored her breasts, and she thought her attire provided just the right level of titillation.

The young man was obviously not expecting such a greeting. He had no idea what she meant by the "examination" thing, but he couldn't wait to find out. He realized he was in a vulnerable situation because he'd shared some of his deepest secrets and insecurities with her. But he trusted her and decided to relax and just go with whatever she had planned. Besides, she looked amazing in her nurse's outfit, and he could see the contours of her incredible breasts. They were perfect in every way. He'd spent hours thinking about them and picturing them in his mind (especially when he masturbated). He loved their size and shape, and the way they moved with her body. He could just barely make out her nipples pressing against the soft cotton. She was so beautiful!

"Now I know young men your age can be nervous about being examined (especially by a woman) but please just try to relax. I'll be as gentle as possible. It's important that you be completely honest. Can you do that for me?"

He was thinking more about her amazing body than what she was saying, but he knew he was in store for something special; and he felt a twinge of excitement. He realized she was waiting for him to respond so he simply nodded his head and said, "OK, I promise."

"Excellent. Then I'll just step outside for a moment while you take off your clothes and put on this robe. You can leave your underpants on for now, but take off everything else. I'll be back in a few minutes."

He quickly undressed and put on the robe.

"Good. Are you doing OK? Is the room warm enough? I want you to be comfortable."

"Um, yea, I'm fine. Thanks."

It was almost like she was a real nurse. She had a stethoscope, blood pressure cuff, tongue depressors and one of those things they use to look into your ears. She started by peering into his mouth and ears and felt the glands in his neck. Her fingers felt cold (and sexy) next to his warm skin. She then took his blood pressure.

"158/89," she said with a frown; "and your pulse is 98. Is that normal for you, or are you feeling a bit nervous?"

"I guess, I maybe I'm a little nervous".

Nervous wasn't exactly the right word. Tingling with anticipation was more like it. He knew whatever was in store for him was going to be incredible, and his emotions were on high alert.

"There's nothing to worry about. Just try to relax while we take your temperature. Please open your robe and slip off your underpants."

"My underpants?"

"Yes, of course." It's important that we get an accurate reading, and young men your age can have a hard time keeping a thermometer securely under their tongues long enough to get one. Fortunately, your rectum provides a nice temperature-stable environment so we don't have to worry about that. Go ahead, there's no need to be shy. It's a medical best practice for you.

Even though they were both 23 years old, her plan was to fuel his humiliation by treating him as though he was so immature that he couldn't be trusted to take care of his own basic needs. Her chiding played directly into the feelings of shame and humility he craved, and he reveled in such feelings as he pulled down his underpants.

Her plan was working! She loved his penis and had eagerly anticipated the moment when she could see it again. It was a little on the small side, but somehow it was perfectly proportioned for his body. She smiled to herself at what was in store for him.

"That's good. Now bring your knees up to your chest and spread them as far apart as you can."

She used her light to inspect his fully exposed anus while he basked in the degradation.

"I'm glad you're keeping yourself clean down here. It's not uncommon for guys your age to be sloppy in that department." She smiled and said, "I guess it won't be necessary for me to give you my personal hygiene lecture. OK now just maintain that position while I get things ready."

She coated the thermometer with petroleum jelly and said, "OK the thermometer's all set to go so let's get started. Spread your cheeks a little wider so I can apply a bit of lubrication. Now just relax."

She put a generous dollop of lube on the tip of her index finger and applied it to the very center of his asshole. She decided to give him a little extra treat by inserting it up to her first knuckle and lubing the inside. His muscles reflexively contracted around her probing fingertip until she slowly withdrew it.

The combination of his being so completely exposed and the incredible feeling of her finger moving around inside were tremendously exciting. He was savoring every second.

She too was savoring each moment, and she knew he was too. The fact that his penis was beginning to respond was proof of that. But she had much more in store. She used the tip of the thermometer to tease his exposed anus for a few moments before positioning it so it was making contact with the very center of his opening.

"OK, I'm going to insert the thermometer now so just try to relax your bottom."

The feeling of the thermometer as she teased his asshole and slipped it inside was wonderful. But then she pulled it out.

She handed it to him and said, "OK, now you do it."

"You want ME to do it?"

"That's right. We need to be sure you can take an accurate temperature when no one's around to help. Just position it over your anus, relax, and gently push it in about a third of the way. She smiled and said, "There's nothing to be afraid of. Young men often enjoy having their temperature taken this way. As I'm sure you know; it's very sensitive area."

She was right of course. He sometimes got the urge to use his toothbrush handle or whatever else he could find to make a masturbation session special. He usually felt like a sicko afterwards, but he loved the feeling of something going in and out down there. And now he was about to do essentially the same thing under the intense scrutiny of this beautiful young "nurse". He suddenly became aware that his penis was semi-erect, and he tried desperately to think of something else to keep from getting harder.

He realized he was lost in thought when he heard her say, "Excuse me. What are you waiting for?"

Eventually she took his hand with the thermometer and guided it into position. "Go ahead now, push it inside and I'll tell you when it's deep enough."

He did as she instructed; probing with the lubed thermometer until he found the center of his exposed asshole and slowly pushed it inside.

"That's far enough. Now why don't you take it out and practice a few times so we're sure you've got the hang of it?"

He loved the feeling of the thermometer sliding in and out, and the fact that she was watching him so intently. He was horrified about his hardening penis, but he knew there was nothing he could do about it.

She loved watching him too. And his beautiful almost complete erection meant her plan was working. She realized her nipples were showing more prominently through her "uniform".

She smiled once again and said, "I see you're getting an erection, and I don't want you to be embarrassed about it. It's not unusual for young men to get hard when they're having their temperatures taken."

Of course, her talking about his erection only made it worse, but he realized that was her intent. She was giving him every opportunity to savor his degradation as he continued sliding the thermometer in and out.

After a few more times she said, "OK, this time we're going to hold it in place for three minutes; and don't let go or your body may try to expel it. It's important that you retain it securely in your rectum."

After what seemed like a very long time she told him to remove the thermometer and give it to her. He worried that it might be soiled, but there was nothing he could do about that either.

"Ninety-eight point eight," she announced. "That's almost perfect. Now hold still while I wipe off your bottom."

She took a moist towelette and thoroughly wiped his puckered opening -- working it inside a bit as she had previously done with her fingertip to clean out the remaining lube. She couldn't resist giving the tip of his now fully erect penis a few playful tweaks and saying, "Look what we have here! Like I said before, you don't need to be embarrassed. Hormone-ravaged young men often have trouble controlling their erections. I'll bet your penis gets hard without your wanting it to all the time.

Well, no matter. It's actually good that you're erect because it's time for me to examine your genitals and an inspection of both your flaccid and erect penis is part of the procedure. The fact that you're already hard will save us some time. Now stand up nice and tall and open your robe."

His body was perfection -- thin and fit, but not overly muscled. His hairless chest and stomach were flat and his legs looked like those of a runner or a biker. But of course, his penis was the immediate focus of her attention. It was perfect. In fact, it was almost the exact size and shape of Fred, her favorite vibrator. She couldn't help but admire the textured shaft and the way it was moving with the beating of his heart.

"Um, is something wrong?" he said; interrupting her thoughts.

She realized she was mesmerized by his gorgeous manhood. "No, not at all", she responded, "I'm simply performing a visual inspection. At first blush your erection appears normal and healthy. Your penis responded quickly to anal stimulation from the thermometer. Is it usually easy for you to become erect?"

The frank discussion about his penis was making him more erect if anything. "I guess so," he responded.

"That's good. And are you usually able to maintain your erections?"

"Yes, I usually can," he said.

"Well, the fact that you're young and otherwise healthy is a plus in that department. If you don't have any concerns about your erectile response, let's move on."

"Now let's take a look at your scrotum. Spread your legs a bit please."

Gently she began examining all sides of his dangling sack -- shining her light on the fuzzy pink skin as she probed it with her fingers.

"Any sensitivities, down here? Soreness, itching, inflammation -- anything like that?"

"Um. No nothing like that."

The young man was relishing this experience more than she could know. The fact that this beautiful girl was inspecting him so intimately while being in complete control played directly into his submissiveness. He didn't want this experience to end. He didn't notice, but the young girl was enjoying the experience too. Her nipples were now decidedly erect and she was getting moist.

"So far everything looks normal. I got a pretty good look at the underside of your scrotum while we were taking your temperature, but why don't we take another look just to be sure? Turn around, bend over and separate your cheeks once again please."

He loved the idea of getting to expose himself so intimately again; and did as he was told.

She lifted up the robe to inspect his perianal area and once again, and shined her light on the underside of his sack and fully exposed asshole.

"As I suspected, I don't see any issues down here. You can turn around and face me again. You're doing fine, but the next part of your exam is especially important. It's time for me to examine your testicles. I know how fragile they are so I'll be as gentle as possible, but I'll need to feel each one with my fingers to look for any bumps or irregularities; and it will be necessary for me to apply some pressure to be sure we don't miss anything. Now, please spread your feet a little further apart."

She began palpating his left testicle -- feeling all around it with her finger tips. When she had completed this task she gave her prize a bit of a squeeze. His immediate reaction was to pull back defensively.

"Stay still please! I need to you cooperate. It's very important that this part of the examination is thorough. I'll try to be more gentile with the next one; but I need you to be brave.

He was on high alert as she moved to the right side, and she relished the feeling of power she was exerting over him. She used a bit firmer squeeze to conclude the exam of her second victim. He had clearly braced for this assault, but still was unable to prevent his involuntary reaction. As she anticipated, his erection had disappeared.

"OK, all done with the hard part. That wasn't so bad was it?"

"I guess not."

She decided a little reward was in order so she said, "You're testicles are nicely developed. They seem very sensitive to the touch. Are you performing regular testicular exams on yourself?"

"Um, not really. Nobody ever told me I should do that."

"Well, it's never too early to start taking good care of yourself. All you have to do is feel around each of your testes with your fingers as I did. If you feel anything odd, you should let me know right away. Now, let me see you do it."

"Do I have to squeeze them like you did?"

"No, that won't be necessary. Now go ahead and show me how you can do it."

She watched as he intently examined first one testicle and then the next.

"That's very good. Your scrotum is currently distended because it's nice and warm in here so it's easy for you to examine your own testes, but if you're cold or sexually aroused, you scrotum will be retracted and things won't be so easy. Therefore, it's a good idea to do self-testicular exams in the shower or a warm bath."

"Um, OK."

"Good. Now just relax and stand up normally. It's good that you're no longer erect because it's time for your flaccid penis inspection. Let's take a nice close look at it together. Let's start with your urethra which runs along the underside, very close to the surface. It's mostly used for urination, but seminal fluid also flows through it when you ejaculate."

She continued to work her way down his length.

"The head of your penis is called the glans; and the ring that encircles the underside of your glans is the corona. The skin of your glans is very smooth, just like it should be; and you have a well-defined ridge defining your glans. Many girls like penises with a nicely defined head like yours. Since you're circumcised you don't have foreskin which makes it easier for you to keep clean. Now let's look at this little triangle on the underside of your glans -- it's called a frenulum. Sometimes it's called the male G-spot because it's so sensitive. I'll bet you know all about that!"

She continued to manipulate his cock so she could see it from all angles until she arrived at the very tip.

"Your urethra opens here in a small slit at the very tip of your glans. When I squeeze the top and bottom of your penis we can look inside."

He savored the feelings of submissiveness as she squeezed open his little hole and peered inside.

"Now let me see you do it," she instructed. "I want you to repeat this procedure whenever you examine your testicles."

"Go ahead, don't be bashful!"

He did as instructed, squeezing open his little slit while she shined her light into the exposed hole and looking to her for approval.

"That's good. See how shiny and smooth it is in there? That's exactly what I like to see." She looked directly into his eyes, and announced, "The physical results of your genital examination are entirely unremarkable -- in other words, you have a perfectly healthy young penis and scrotum. You can close up your robe now; but I have a question. How would you say the size of your penis compares with that of other full-grown men?"

She knew this was safe space because of their previous hilltop conversations or she would not have confronted him with such a potentially threatening topic.

"Um, I guess it's a little smaller than most guys."

It seemed strange even to him that he was turned on by being forced to admit that his penis did not measure up; and by having to defend it to her.

"I'm glad that you're able to admit that. The first step in coming to terms with a smaller penis is acceptance. Do you sometimes feel ashamed or embarrassed when others see you naked? Are you shy about showing yourself to females?

"I guess maybe I am a little bit, sometimes, but there's nothing I can do about it, so I just try not to think about it."

"It sounds like you've reached the acceptance stage. That's OK as long as it's not inhibiting your socialization. I hope you know that having a smaller penis has nothing to do with your virility. One of my patients is a lawyer who's a complete macho badass and has a penis way smaller than yours. And I know another guy who's hung like an elephant that's a total asshole. Besides, smaller penises tend to increase is size more than larger ones when they become erect. Even though size is really irrelevant, that fact can be reassuring for young men like you. We can see about that later.

"What does that mean," he thought to himself.

"OK, let's move on. Now in this part of the exam we're going to talk about your masturbating. This topic can be difficult for some young men but it's especially important for you to be open and honest about it. Masturbation is a very important part of life for young men your age, and if you have issues or concerns, we need to have a conversation about them. Let's start with the basics. How often do you do it?"

Even though he suspected this subject was coming (and hoped it would) he felt himself blush at the thought of admitting that he masturbates and discussing it openly. One of his biggest fears was getting caught, or being confronted with evidence that he plays with himself, so he hesitated while trying to figure what to say.

"Come on now, it's a simple question. I know for a fact that you masturbate. I just need to know how often...once a day, twice a day, once a week -- whatever it is."

"Um, I guess I do it just about every day."

"OK, I think we can assume that means every day. Do you ever do it more than once a day?"

"I guess sometimes I do, maybe once or twice a week."

"Now see, that wasn't so hard to admit, was it? Did you already do it today?"

"No mam. The last time was last night in my room."

"That's nice, I hope you enjoyed it. Is that where you usually touch yourself?"

"Yes mam. I usually do it at night before I go to sleep. Sometimes I do it in the shower too; if I can't wait until bedtime and my roommates aren't around. But then I usually do it again at bedtime anyway."

"That seems like a healthy pattern for a young man of your age. Where do you usually ejaculate?"

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