A Teachable Moment

I am a professor at a small Midwestern college which will have to remain nameless in this story. The college dominates our small town as the largest employer, and the student body makes up a large percentage of the population. There is nothing too unusual about that, there are countless little college towns like ours.

I had called in a female student for a counseling session because she is not doing well in my class. Unlike High School, we do not babysit the students. If they do not attend lectures and do not do well on exams, then they pay the consequences. But this young woman initially showed promise, and I wanted to find out why she had stopped performing.

There was a faint knock on my office door, and I walked over to open it. Standing in the hallway was the student I had summoned, a young lady named Julie. She is incredibly petite, probably under a hundred pounds soaking wet. She is slender and almost flat-chested, and not even five feet tall.

"Come in. Sit down, make yourself comfortable."

I wanted to be friendly and easy to talk to, not judgmental or critical. This was not a session to punish her, it was to help her. I ushered her to a chair in front of my desk, and I sat down behind the desk.

I had seen her in class of course, but up close and personal I was amazed by what a little pixie she is. She has a short, almost boyish hairdo, and a wholesome girl-next-door face with no makeup. She is very pretty in a Tom Boy sort of way, and I was very attracted to her.

"What can you tell me about why you are suddenly not interested in my class? Am I really that boring?"

She avoided making eye contact and fidgeted and squirmed in her chair.

"It's not you, it is my problem. It is very personal, and I don't think I can talk about it."

I got up from behind my desk and walked around to sit on a chair directly in front of Julie's chair. I wanted to be less formal and make it more personal and friendly.

"Julie, I wanted to talk about your poor performance in my class, but it seems you have personal issues. Maybe those issues are the cause of your problems in class. Can you tell me what is going on?"

I waited as she thought for a moment, and then said "It is the guy I have been seeing."

Of course, I thought. A relationship problem.

"Can you explain? Tell me more."

She seemed embarrassed, and reluctant to talk.

"It's a sex thing" she said softly.

"Julie, you can talk to me about anything. This is a private, closed door session. Nothing you say will leave this room."

To reinforce that, I walked to the door and locked it.

There was only awkward silence for a few minutes, but I waited for her to respond.

Her face was red, but she managed to say "He said that I look like a boy, so he wants to do me like a boy."

It took me a moment to understand that, but I finally did. So this jerk she is dating wants to sodomize her. Can't say I blame him.

I have enjoyed anal sex with a few different women in my time, but none were like Julie. Don't misunderstand; I do not like overweight women. However, my past conquests were average size women with some curves and a normal sized butt.

Julie, on the other hand, was petite and slender, with a small, tight butt. I had to fight to maintain my disinterested, nonchalant demeanor. I needed to appear totally professional, with only Julie's best interest at heart.

"Well, Julie, anal sex is something many women like. Some even learn to prefer it that way. Why don't you try it?"

"We did. It didn't work."

"Julie, please don't make me pull everything out of you a little at a time. Tell me the whole situation."

She was even more red-faced now, but she said "He tried to get it in me, but it wouldn't go in."

"He poked and prodded and fumbled around for a while, and then gave up. I was willing to do it, but maybe my . . . umm . . . maybe I am too small."

She almost said 'my asshole is too small' before she caught herself. This was really starting to turn me on. The image of this innocent young woman with some guy trying to get his cock up her ass was exciting.

I began to formulate a plan to get her to try it with me. I knew I could get it in even if she squirmed and squealed and tried to resist. I know from experience that if you push hard enough, a woman's asshole will stretch and accept your cock. And once you get it in, they usually surrender and enjoy it.

"Does your boyfriend have an unusually large penis?"

She said "I don't know. I don't know what is normal."

I seized the opportunity and unzipped my pants and pulled out my dick. It was semi-erect due to the direction this conversation had taken.

Julie burst out the expression that all the young people use, "Oh my God!" She looked away, but her eyes were drawn back to it. "Should you be doing that?"

One of the ladies I see from time to time is an English Lit professor with a clever sense of humor. She said "dick" is not an adequate description for my penis; she calls it "Sir Richard" out of respect for the size of it.

"Julie, I need to find out if your boyfriend's penis is larger than mine. This is the only way I can think of to determine that. We are both adults, just try to stay objective."

She stared at it intently, as if it was a valuable work of art.

She said "I can't tell."

"How is that possible? You have had other kinds of sex with him, haven't you?"

"Yes, but it was always in my room with the lights out. I never really saw it as clearly as I see yours."

I said "Well, you must have touched it or felt it in some way. Feel free to touch mine."

She was reluctant for a moment, but then she reached over and grasped my shaft. She touched it lightly from the head to my balls. Her tiny, girlish hand made it look even larger than it is.

"I better wait for a while, it has not finished growing."

That was true; my cock was stiffening and swelling in reaction to her touch. While she waited for it to be fully erect, she took advantage of the opportunity to reach into my un-zipped pants and feel and caress my hairy ball-sack.

Finally satisfied that it was at full attention, she said "Yours is much larger than his. Especially longer."

"Your balls are much bigger, too." She blushed after she blurted that out.

I said "OK, we have determined that. Now I want to conduct a little experiment. I want to show you that anal sex is not only possible; it is very erotic and satisfying. We will consider it part of the counseling. It will be a demonstration and training exercise for your education."

She pondered that for a while, looking away and then looking back at my cock.

"I don't know," she said, "we don't know each other that way. I don't feel that way about you, I barely know you. And if my guy couldn't get his in me that way, you will never get yours in."

"Julie, you need to trust me on this. We are not talking love and romance; this is not the start of an affair. We both need to be calm and objective, and recognize that this is for your future. You need to become more mature and discover your sexual needs and desires. You also need to learn how to please the man you are with. I will show you how to teach your boyfriend to do it."

She remained silent for a couple of minutes. I waited her out. I was confident that I could convince her, because it was obvious that she was aroused by fondling my cock.

I could almost see the thoughts running through her head. She couldn't keep her eyes off of my cock. She was clearly torn between curiosity and arousal, and apprehension and modesty. I am sure that as she stared at my stiff hard-on she was trying to imagine what it would feel like sliding up her asshole.

Curiosity and arousal won out, and she finally answered "OK. But please be careful. How and where are we going to do this?"

"Well, to begin, please take off your jeans and panties. You can leave your top on if that is more comfortable. You can bend over my desk and keep your feet on the floor. Just rest your head and shoulders on the desktop. I will stand behind you."

I expected some resistance, but there was none. She stood up and stripped off her jeans and panties and kicked off her flip-flops. In spite of my generous offer, she pulled off her tank-top and bra as well. She stood facing me, completely naked. Her breasts are small, but perfectly shaped and what some people call 'perky'. Her pubic hair was trimmed into a cute little moustache.

Her slender thighs allowed for the 'crotch clearance' that all the super-models want. Her pussy lips were in view and her perfect little butt cheeks also could be seen from the front because of the wide gap of her crotch. Her asshole was hidden in the crack of her butt, and I could hardly wait to see it.

I pulled off my pants and briefs, and my cock swung fully into view. She gave it an awe-struck look, and said "Oh my God!" again, but she bent over the desk as I instructed her to do.

I couldn't believe my good fortune. She was completely compliant and submissive to me. She was on her toes to keep her feet on the floor, and was face down on the desktop. Her legs were slightly apart to maintain her balance, and her little flower of a pussy was in plain view. Peeking out just above that was her tiny pink asshole.

I reached between her legs and stroked her pussy. I inserted my middle finger and finger-fucked her briefly. Her arousal was clearly evident by how wet it was.

"This is just to get some lubrication" and I moved up to her asshole. I inserted the same finger to transfer some of her vaginal secretions. Her asshole was incredibly tight, but I did manage to get my finger all the way in. She held still and surrendered to this invasion of her most private part.

I pulled my finger out of her asshole and moved into position to fuck her, and I spread her butt cheeks with my hands. That left me without a hand to guide my cock, so I needed her help.

"Julie, please reach back and spread your butt for me. I need to see what I am doing."

"God, this is embarrassing. You will see everything with these lights on."

"Julie, I am an adult man. It will not be anything I haven't seen before. Please just cooperate."

The authoritarian approach worked and she reached back and spread her tiny butt cheeks as far apart as she could. I put the tip of my cock up against her asshole and waited. She was trembling with anticipation and maybe a little fear.

I started to push but the resistance was too much. I adjusted my aim and pushed up into her vagina. She looked back at me with a puzzled expression, so I told her that this was just to get more lubrication. She was not a virgin, but her vagina was still incredibly tight. I guess there had never been anything as large as my cock in it. I only pushed about half of it into her.

I had forgotten what a young woman's vagina was like. Having never gone through child birth, Julie still had the frills and ruffles and ridges inside her that tickle a cock and coax the semen out. I wanted to continue, but I also wanted to be the first man up her asshole.

I pulled out of her vagina, and my cock was now wet and glistening with her slippery love-juice. I wished that I had an economy-size jar of Vaseline, but this would have to do. I put the tip up against her asshole again and pushed.

Her anus finally realized that resistance was futile, and the head of my cock disappeared into her. She yelped like a small dog that had been kicked, but she didn't ask me to stop. I paused for a moment to let her get used to it, and then I began to methodically push it up into her.

Slowly but surely my rock-hard cock slid up her asshole, a fraction of an inch at a time. She surrendered to it and just held still, holding her butt cheeks open for me. I was amazed that my cock was continuing to slide into her tiny body, but there was no indication from her that she had all she could take so I kept going.

When it was all the way in, my pubic bone pressed hard against her tail-bone. My other lady friends have more substantial butts that provide a cushion for me to bump up against. Julie is so slender that her butt cheeks are much smaller, and with her pulling them apart I got 100% of my cock into her.

"Is that all of it?" she whispered.

"Yes, Julie. You took it all. I knew you could."

I pulled out a few inches and pushed back in, and repeated that a few times. I couldn't fuck her fast, she was way too tight, so I had to fuck her in slow motion. She was so aroused I could almost feel the heat rising from her body. I was just as hot because this had to be the best sex I have ever had.

I tried to maintain a steady beat, like a metronome, as I methodically slid my cock in and out of her asshole. Her eyes were closed with her head down on the desktop, and her face to the side. She was breathing heavily through her open mouth.

With each thrust into her my pubic bone bumped up against her tail-bone, and my balls pressed against her pussy. My cock is about nine inches long, and I imagine the head is in the vicinity of her belly-button (on the inside) when it is all the way in.

Each time it slid all the way in and I bumped against her it forced her to exhale and make a little grunting sound. This wasn't pain or even discomfort, it was just caused by me slapping into her wide open butt.

After a few minutes of this, she moved her hands closer to her asshole, and touched my cock right where it disappeared into her. Now my cock slid through her fingers on the way into and out of her asshole.

That was too much for me to take, and I knew I was about to cum. I slammed all the way into her and held still while I shot my load. My cock throbbed and twitched as the cum raced through it out to the tip.

Julie's eyes snapped open with a startled look as the first spurt of cum went forcefully into her. As it continued to gush into her, her expression turned to curiosity as she experienced the strange new feeling of cum filling up her asshole. I had not ejaculated like this since I was a teen-ager. I was surprised that one of my internal organs didn't fly out of my cock.

We stayed locked together for a few minutes, with me huffing and puffing to catch my breath. I started to pull out of her, but her anus was still so tight it wanted to go with me. I had to pull out of her as slowly and carefully as I had pushed into her so that I would not turn her inside out.

When the head popped out I stepped back, and she turned and sat on the edge of the desk. We stayed that way for a while, me standing in front of her while she stared at my still-hard cock.

I asked "What are you thinking about now?"

Still staring at my cock, she answered "I am amazed that all of that went into me. It was way up in my stomach."

"I told you it would work."

A little cum was still oozing out of me, and it formed a creamy gob on the head of my cock. It was about to drop off and splatter on the floor, and she didn't want it to go to waste.

She said "Can I have that, please?"

"Of course, help yourself."

She reached over and scooped the cum off of my cock with one finger, and put it in her mouth. She sucked her finger clean, as if she was tasting the frosting on a cake.

I helped her get down off of the desk, and she sat down in the chair she originally was using. There was a wet spot on the edge of my desk, so I went into my private bathroom to get a towel. While I was there I washed my cock using the hand soap on the sink. I took two towels with me back into the office.

I wiped off the edge of the desk because I didn't want to leave a cum stain for the cleaning lady. I handed the other towel to Julie so she could put it under her to sit on. I imagine cum will soon be leaking out of her asshole since I put about a quart of it into her.

I sat in my chair opposite her and we talked for a while. It was quite a scene with her completely naked and me naked from the waist down, talking as if we were having a conversation at a social event.

"So was it painful at all for you?"

"No, not painful. A little uncomfortable at first. Then there was some pressure, and a feeling of being filled up as it went all the way up into me."

She collected her thoughts for a moment, and then said "After that I liked it. Especially when you finished in me. It just kept squirting and squirting and squirting into me."

She smiled modestly when she realized what she had said.

"I imagine you think I am a depraved little slut."

"No, Julie, I think you are a completely normal woman, with a healthy sexual appetite."

Eventually talking about sex led her to reach over and fondle my cock again, waking it up. It was obvious that she wanted more, so I returned to my teacher persona.

"Julie, you have had the lecture and the demonstration, now it is time for a test to see what you have learned. You take charge and tell me what to do. I will not do anything except what you say."

She dropped to her knees in front of me and began to suck my cock. I was disappointed because I wanted to get it back up her asshole. I wasn't disappointed for long.

Julie pulled it out of her mouth and said "I just wanted to get it hard enough to go up my ass."

She turned around and positioned herself over me, and reached between her legs and held my cock with one hand while she pulled one butt cheek out of the way. She lowered herself and guided my cock to her asshole, and slowly sank down on it. With one slow continuous motion she sat down and took the entire length of it up her ass. The fact that her asshole was stretched and lubricated with cum made it fairly easy.

"Just hold still and let me do this."

She held onto the armrests on the chair for support, and started to raise and lower herself onto my lap. When she lifted up just the head remained in her, and when she sat down my whole cock was in her. Holding onto the armrests meant she couldn't spread her butt, so I watched as my cock appeared and disappeared into the crack of her girlish butt. She kept this up, essentially fucking herself; until she sensed that I was about to cum.

She sat down firmly on me and stopped while I pumped another cum-load into her. She rocked back and forth and swayed side to side with pleasure as the cum shot into her like the Old Faithful geyser at Yellowstone. Then she reached between her legs and rubbed and stroked her clit, and brought herself to an intense orgasm. Her anus clamped on my cock in a series of spasms as she grunted and squealed like a monkey.

She collapsed on my lap as if she felt safe in my arms, and I reached around and fondled her breasts with one hand and her wet pussy with the other. She reached between her legs and grasped my balls a little too enthusiastically.

"Julie, you are squeezing too tightly. It is uncomfortable."

"Oh, I'm sorry. I just wanted to make sure they were empty."

I suppressed a laugh at that. I will have to give her a lecture about male anatomy so she understands that cum is not stored in the testicles. I guess she thought that my cock was like a long enema tube, and my balls were like the rubber bulb you squeeze to force the liquid into you. It was charming to realize that she wanted to completely empty me inside her.

Eventually we realized it was over, and she lifted herself off my lap, withdrawing my cock as she did. She returned to her chair across from me, and sat on the towel. I was glad I had brought her the towel, because cum will probably flow out of her now. She has two big loads in her, and the last one went in as she was sitting straight up, so gravity will cause it to run back down and out.

"Julie, you passed the test with flying colors. I would say an A+. You can now show your boyfriend how to do it. For the first time you should probably sit on it like you just did so you are in control. Just tell him to shut up and hold still like you did to me."