The Only Problems with Braces

As I have mentioned in a number of the stories I have written, before my retirement ten years ago, I worked as a professor of English in a small but expensive New England college.

As you already know if you ever went to college, English 101 is required of all freshmen students. The purpose of this course is for the professor to try and enable students to write in some reasonably intelligent way. Many of the students can write only on a 6th grade level. God knows how they graduated from high school.

At any rate, the usual procedure is to give out writing assignments and see how well they do with them. The subjects of the assignments are the usual boring standards: The Best Day in My Life, The Worst Day in my Life, Who I Would Like to Meet From History, etc. One of the typical boring assignments was: The Most Embarrassing Experience of My Life.

Jeremy Hopkins (named changed to protect the guilty) wasn't the brightest bulb in the room, but I thoroughly enjoyed his essay and thought you might like to read it. Here it is:

"We both grew up in the same small town, so I had know Jessica since we both were in the third grade. By the time we reach the senior year of high school, we had both just turned 18 and were looking forward to college.

Also by that time, Jessica had turned from a child into a very beautiful girl. She was about five foot five, 105 pounds, dark brown hair that hung to her shoulders, and a smile that filled the room. The only thing wrong with her smile was that like a lot of the girls, she had to wear steel braces. They always made her mouth look unattractive, like there was something caught in her teeth. But the rest of her was really nice looking. She also had what appeared to be a very beautiful petite body. Even though I had never seen it in the flesh, so to speak, I could tell that it was something special.

In the last year of high school, I was very good at math and science, and Jess was pretty good at English and History. But still, she was worried about the SATs which were coming up.

"I know I'm going to do terrible in math," she told me one day on the way home in the school bus. "How am I going to pass it?"

"Study," I said.

"But I don't understand the concepts."

I shrugged.

"Could you tutor me in math?" she asked. "We only have a week until the tests."

Normally, this would be a boring idea for me, but I began to think of a way I could put it to my advantage. "What's in it for me?" I asked.

She looked puzzled. "I don't know. What do you mean? What do you think should be in it for you? I don't have any money."

"I'm not interested in money. But you do have something I would like."

"What's that?"

"I'll tutor you for two hours after school, when your parents are working, if you'll be naked when I do it."

She stared at me. "You're kidding, right?"

"No. You're the most beautiful girl in the school, so that's what I want."

She thought about it for a minute. "Is that all you want? Just naked."

"Yes."

"Okay, I'll do it. But you have to promise me you won't tell anyone."

"I promise."

"Tomorrow after school."

"I'll be there."

When I knocked on the door the next day around 3 p.m., Jess opened it. She was barefoot and wearing a white terrycloth bathrobe. "Come on up to my room," she said. "My parents won't be home until about six."

I followed her up the stairs and into her room. It looked like a typical girl's room: a single frilly bed, a dresser, and a lot of posters of rock and movie stars. On the floor beside her bed was what looked like a white bearskin rug. "I like to sit here and study," she said. "It's comfortable."

"Okay." I took some math books out of my book bag and put them on the rug. Then I sat down.

"Here goes," she said. She undid the ties around her robe, opened it, and let it slide from her shoulders. She was even more beautiful than I could have imagined: Small but pretty breasts with copper-colored nipples the size of quarters. And between her legs, a pretty brown bush which looked like it had been trimmed. But what did I know? I had never seen one before.

"You look beautiful," I said.

"Thank you. Can we work now?"

"Of course." I gave her all the help I could for two hours even though it was difficult with her sitting there naked beside me.

"What about tomorrow?" she asked. "Can you come over again?"

"Sure. But the price has gone up."

"What do you mean?"

"I've already seen you naked. So now what I would like to have is a blowjob."

"You've got to be kidding."

(I need to interrupt at this point. I have read that back in the Dark Ages, meaning the fifties, a blowjob was something you could only get from a prostitute, certainly not your wife or girlfriend. But after the sixties and the so-called Sexual Revolution, everything was different. Now this was the Modern Age, and in high school, a blowjob was as common as a handshake and pretty much meant the same thing: Nice to know you.)

"I'm not kidding," I said. "I think you're the prettiest girl in the high school, and I would love to have a blowjob from you." I didn't tell her that I had never had a blowjob before, since I had never had a girlfriend.

She thought about it. "You won't tell anyone?"

"Of course not."

"Okay, come around at the same time, and if you teach me a lot in two hours, I'll give you a blowjob."

"And you have to be naked at the same time."

She sighed. "All right."

Fantastic, I thought. I could hardly wait.

I didn't know she was going to be naked for the whole tutoring session, but that's what she was. She actually answered the front door naked, which was a big surprise to me.

"You look really beautiful," I said with admiration, looking around to make sure no one was in the vicinity.

"Thank you. Let's go upstairs."

At the end of our two hours of tutoring, I stood up.

"All right," she said. "Take it out."

I unzipped my fly and took it out. It already was semi-erect. She looked at it a moment, then wrapped her hand around the base and put the other end in her mouth. She gagged on it at first but then got used to it. I know that when you're older, you're supposed to have some restraint in making love in order to make it last longer and be more pleasurable for the girl. But I was the typical teenage boy, so in about five minutes, I came in her mouth. She choked on it at first but then swallowed it and kept on swallowing until it was all down—except for the little bit that ran down from the side of her mouth. Wow! What a treat!

I started to pull my now limp and soft penis out of her mouth—and found that I could not. It was stuck. Somehow, the pubic hairs at the base of my penis had gotten stuck in the steel wire of her braces. It hurt like hell when I tried to pull out.

"Mfff?" she asked.

"I can't pull it out," I said. "My hair is caught in your braces."

"Wffff?" She tried to pull back.

"Ow! Ow! Ow!" I cried. She tried to pull back gently, and I tried to pull back gently. But it was no use. My penis was stuck inside her mouth.

"Do you have scissors?" I asked.

"Mffff." She pointed to the floor.

"Under the floor?!"

"Nffff!" She shook her head.

"OW!"

She bent down slightly and picked up her pen and notebook. Then she wrote in it: Kitchen.

"How the fuck are we going to get down there?" I asked.

She made some stupid motion with her fingers, then wrapped her legs around my legs, her arms around my waist, and lifted herself up slightly so her butt was off the floor. I got it: I was supposed to carry her down that way. It didn't look like the best idea in the world, but I didn't have a better one, so I started slowly sliding my feet across the carpet toward her door.

Going down the steps was certainly not the most pleasant experience either. I cried "Ow. Ow. Ow" all the way down.

Finally, we were crossing the hallway at the front door, and the kitchen was in sight. Thank God.

And that's when I heard it. A key turning in the door. The door opened, blocking us.

"I'm home!" her father called. "Had to leave early when the heat went out." Then he walked in, closed the door, and turned. "What the f---," he said.

"Hi, Mr. Johnson," I muttered. "This isn't what it looks like."

Right. That was the perfect thing to say. We must have made a lovely picture. "Do you know where the scissors are?" I innocently asked.

I won't bore you with the ugly details of what followed, but we did live through it. Jessica was grounded for two weeks and forbidden to ever see me again.

But at her request, I continued tutoring her for the SATs. We did it at the town library after school. As a result of this, we actually did become good friends and were looking forward to going away to the state university together.

II

At the state university.

Both the girls dorm, where Jessy was, and the boys dorm, where I was, allowed unsupervised visits from the opposite sex on Saturday and Sunday. So it was not long before she and I became real lovers, and she gave up her virginity to me. Also, another plus was that she no longer wore braces, so she was able to provide me with some fine—and unsnagable—blow jobs.

Then Christmas vacation rolled around, and we went back home. Her parents still hated me and didn't know that we were a "pair" at college, so we had to keep our meetings discrete. A lot of times we met in the town library and just hung out. We couldn't go to my house and make out because my mother was home all day.

"I want to try something different," Jess said to me one day in the library.

"What."

"I want to see what anal is like. I read about it in COSMO. I want you to do it to me."

"You mean...?"

"Yes," she said with a wicked smile.

"Where?"

"My house is empty from three to six."

"Don't you think that's a little risky?"

"Not if anyone isn't there."

"I don't know...."

"Come over tomorrow at three and you can take my anal virginity. And I'll give you a blowjob too."

That was too good an offer to resist. "It's a deal."

"COSMO said you should use a lubricant, especially the first time. I found one in my parents' medicine cabinet. It's called K-Y."

"Okay."

She leaned closer so no one in the library would hear. "See you at three. And you can fuck me. Not in the grass. But in the ass."

Wow, what a poet.

So I got there at three, and as she had promised, no one was there but her. She greeted me at the door in the same white terrycloth robe—which instantly brought back some frightening memories. But I suspected she had nothing on beneath it, which brought back some good memories. She held up her hand with a blue tube of KY lubricant in it and smiled.

"Hi," she said, then took me by the hand and led me up to her room.

"Are you sure about this?" I asked.

"I'm sure I want to try it. I'm not so sure I'll like it. But I'll try anything once. That's what education is all about, right?"

"I guess so."

And she didn't waste any time. When we got to her room, she untied the white belt around her bathrobe and pushed it off. I could never resist staring at her when she was naked. What a cute little bush.

"Get undressed," she said.

"Okay."

I did so, as she hopped on her bed and got into the doggy position.

"Can I at least have that blowjob first?" I asked. "This might be a little difficult, so I would like to be as hard as possible."

"Oh all right. Lie down up here."

That's what I did, as she knelt over me and proceeded to give me one of her wonderful blowjobs that I had become accustomed to. Within a short time, I was as hard as I was going to get.

"Okay, let's do it," she said, as she got up and assumed the doggy position again. She picked up the tube of KY and handed it to me. "Here, rub this on my you-know-what."

"Inside too?"

"I don't think that will be necessary. Your thing should push the lubricant in. But put a lot of it on my you-know-what."

"Okay." I proceeded to do as she had instructed. "That enough?" I finally asked.

"I guess so. Let's do it."

I positioned my stiff member so it was pointing at her tiny butthole. I didn't know if this was going to work, since her butthole was about the size of a dime and didn't look like it was going to get any wider. But I pushed forward as hard as I could.

"Ow!"

"You want me to stop?"

"No, do it! I want to see what it feels like. The article said it would hurt at first."

"Okay, here goes." The KY did its trick and greased my pole so that I was finally able to push all the way in her.

"Ow!" she cried again. "Are you all the way in?"

"Yes."

"Then pull it out slowly, but not all the way, and then push it back in slowly."

I did as she instructed. "How does that feel?" I asked.

"It feels like we're doing something really dirty," she said with a giggle. "I like it."

And since she was so incredibly tight—tighter than her virgin pussy had been—I liked it too. It did not take me very long to come inside her. "Ahhhh!" I cried.

"I felt your sperm. How did it feel to you?"

"Different, but good. I liked it too." I collapsed on her back, which caused her to flatten out on the bed as well.

Finally, after about ten minutes of just enjoying each others' naked bodies, I decided it was time to pull out, clean up, and get dressed. I noticed the time was 4:30.

But there was only one problem: I was soft and limp. I couldn't pull out. Her tight asshole was holding me like it was a vise grip. When I tried to pull out, it felt like her vise grip was going to pull my dick right off. "Ow!"

"What's the matter?"

"I can't pull it out."

"What do you mean you can't pull out?"

"I can't pull out, Goddamn it. Your asshole is like a tight fist. It was hard to get in, but it's impossible to pull out without ripping my dick off."

"Can't you get hard again?"

"Not this way. Can't you relax your muscles?"

She tried to. "No. "

"What the fuck can we do?"

"Can you use some more of the KY?"

"No, there wasn't that much in the tube—and I used all of it."

"Great....Wait a minute, I've got an idea."

"Which is?"

"I remember reading about a movie called 'Last Tango in Paris.' Marlon Brando used soft butter to do it to some girl."

"So? I suppose you have butter up here?"

"No, but there's some on the counter in the kitchen."

"How will we get there?"

"You're strong, and I only weight a hundred and five. You can pick me up and carry me down."

So that's what I did. I kneeled up on the bed, put my arms around her waist, pulled her toward me and slid off the bed. Then I carried her out of her bedroom and down the stairs with her hanging off my dick. What a lovely picture we must have made.

I crossed the hallway at the front—and then stopped.

Someone was turning a key in the front door. The door opened, effectively blocking us.

"Anybody home?!" he called. "I think I'm getting the flu, so I thought I should come home!"

Then he closed the door...and turned. "What the f---," he began.

"Hi, Mr. Johnson," I said, with what could only be described as a 'shit-eating grin.' "This isn't what it looks like."

What else could I say?