Sex stories

Erotic fiction and short sex stories




Henry's Exposed Adventure Ch. 01

[This is a work of fiction. All characters depicted in this fictional work are 18 years of age or older. Any resemblance of any character to any real person, living or dead, is purely coincidental.]




My name is Henry Watson, and when all these things happened I was 18 and a senior at East Point Military Academy, an all-boys military high school in upstate New York. It was good being back at school, though I was a little sad that, come the end of the year, I had friends that I might not see again for a long time, if at all. It was fall, the air was chilly and crisp and tasted like lemon if you just breathed it in through your mouth fast enough. In those hours when the sun shone, the flaming oranges and reds of the leaves stood out against a sky as blue as the blue of Michelle's eyes, but before long it would retreat into a semi-permanent shade of battleship gray. The trees, with their waving masses of reds, browns and golds, were on fire, cold tongues of flame that flickered with each change in the wind. And wherever the wind had piled up hundreds of their little cadavers in small piles I made it a point to kick my way through it as I walked across campus to class.

Michelle is Michelle Hadley, my girlfriend, but she's back in New York City, so I wouldn't see her again until Thanksgiving break. Even though turkey day was only eight or nine weeks away, time passes more slowly when you're young, and it felt like I had to wait two eternities to see her again, and to get our tongues in each other's mouths.

East Point Military is just outside the little town of Armpit. That's not really the name of the town, of course, but that's what all the guys at the school called it. Back in those days Armpit had an ice cream shop, a store that sold cheap clothes and food high in sugar and brimming over with the type of fat that's bad for your heart, and a run-down theater with broken seats that played movies long since out of circulation down in New York City. But Armpit was the only outpost of civilization within a hundred miles of East Point, and it was within walking distance of the academy. The movies and the ice cream shop provided the perfect excuse for a Saturday evening date with a Grimsley girl -- always heavily chaperoned. Plus, you had get a date with a girl there first. We talked a lot about different Grimsleys, as we called them, but until Saturday rolled around, we had to be disciplined and focus our testosterone-addled brains on things like algebra and whether Hamlet really killed Ophelia.

East Point was a military-style school, but it was pretty much like any other all-boys' boarding school, except that the discipline and regimentation were heavier and we were required to wear uniforms. On most days this wasn't so bad because it was just the "daily grays," a tunic that buttoned up the front like a combination shirt and light jacket, and a pair of pants, both gray. For parades and at all formal occasions, though, we had to wear our dress uniforms, which were real 19th century Queen's Own Hussars affairs with white, high-waisted pants, a jacket that was short in the front and had long tails in the back. If we were drilling on parade, we had to wear these tall shako hats made of fake bear hair. We called parades "nutcrackers" for two reasons. First, the get-up we had to wear made us look like 450 Christmas nutcrackers come to life. And, second, because it was ballbuster. Or a nutcracker, in more polite terminology.

The school was on Lake Penasaukee, which was about ten miles long and ranged from about half a mile to a mile and half wide. Legend was that Penasaukee was a Mohican word meaning "penis - suck it." First-years were required to point their fingers at their crotch when whenever they said the name of the lake. It was a big lake, but only about 25 feet at its deepest point. That was more than deep enough to drown in, and it was damn cold, so we weren't allowed in or on the Lake unless it was an official school activity. You could get kicked out if you broke that rule.

I was sent, or rather sentenced, to East Point by my parents. My performance at a regular private high school in New York City was not very impressive. They said it would improve my academic performance so I could get into a good college. Truth was that Michelle and I spent a lot of afternoons together making out and walking around the city when we should have been studying. So my parents had a point because I'd be about 350 miles from Michelle and that lovely mouth of hers.

But after I got to East Point I still got mostly C's and a few D's, with an occasional B- thrown in as a saving grace by some sympathetic teacher. I was counting more on my family's money than my grades to grease the college admission rails. My father traded oil on the spot market, made a lot of money doing it, and traveled around the world for his job. My mom never traveled with him but instead lived in our apartment on the east side of Manhattan.

Colleges aside, their real reason for sending me to East Point was to get me out of the way so they could pursue their own interests. Love interests, that is. They thought I didn't know that they cheated on each other, but it was too obvious not to notice. Parents always seem to have a denial complex about things like that. "Oh, I'm sure he doesn't know that I'm screwing my assistant at the office," when the assistant would be dumb enough to call him at home where I could quietly pick up the extension in my bedroom and listen in. My dad always had an "assistant," sometimes two, always female and most only a few years older than me. Some of them were so outrageously beautiful and dolled up they made me feel embarrassed. I mean, I wanted to make out with them, a lot, but when you knew your own dad was fucking her it made things really awkward. He changed assistants every few months, anyway.

My mother was a bit different, though. Sure, she had her boyfriends to balance things out. Some of them were "mature" older men with gray hair, but some, like my dad's assistants, looked like they were fresh out of college and couldn't have been more than a few years older than me. What made my mom interesting was that she also had girlfriends, and they weren't just friends who were girls. I was pretty sure she swung both ways, though I never actually saw her with another woman in a compromising position.

Mom and dad each knew what the other was doing, but they'd worked out their own peaceful coexistence for their little Cold War. Mom didn't complain as long as the money kept flowing in. Dad was happy if mom didn't interfere with his women or talk trash about him to people in their social orbit. It was all something we just didn't talk about on those rare occasions when the three of us were together around a table.

So what about me? I'm maybe a little under average height for a guy, about 5'6'', and definitely on the thin side. I preferred the term "wiry" to "skinny," but I had to admit that just never had much muscle in my shoulders or arms. Not having lots of muscle was a problem I could live with, but what I couldn't get used to was the problem I had with girls. I'd had dates, and sometimes a relationship that lasted a few weeks. One lasted a month and a half. But I never had sex with any of them. Whenever things got to first base, I had to stop it there. Sometimes I'd sabotage my own relationship by being rude, other times I just stopped calling the girl. It wasn't that I didn't like them, and I certainly didn't want to be rude. But I was desperately afraid of going too far in a relationship -- and going too far with a girl -- because of my problem.

What problem was that? I had the worst of both worlds. Half of it was that I got a lot of erections, some spontaneous, others triggered by the sight of something intriguing and female. At that age a boy's hormone factory runs three shifts a day, so everybody got a lot of inopportune erections. But I got more than most. My little soldier down below was always ready to stand at attention, even when I wasn't thinking about sex. My morning wood was so hard that just to get rid of it I had to wait until my roommate had gone out to take his shower and then jack off like crazy using the dirty magaziine I kept hidden under my mattress. Sometimes, when I knew I'd have to speak in front of a class, I "bought insurance": I'd duck into one of the stalls in the bathroom on the way to class and jerk off. Paying for insurance has never felt so good since then. But that was just half of the problem.

The other half was that my penis was -- and still is -- small. Not a micro-penis, but it's considerably smaller than average. Soft, I'm just about one and a half inches. Well, not quite, but almost. Getting out of Lake Penasaukee or a chilly pool just aggravated this condition. Erect, I gain another inch, so at maximum stiffness my dick reached the commanding height of two and half inches. Well, almost two and a half inches. A penis my size was impossible not to notice in the locker room and the showers, and so I was given a few nicknames. Among the more colorful ones were "Sparkplug" and "Winecork."

The size of my dick was why I was never very forward with girls. I was always afraid of getting alone and busy with a girl. The thought of her putting her hand on my crotch -- or worse, down the front of my pants -- made me break out in a cold sweat. I always had to stop the action no matter how good it felt. I couldn't bear the thought of some girl getting startled by my diminutive penile dimensions and laughing me into the floor. Even more nightmarish was the thought that she would tell all her girlfriends about the date and how small my dick was. I'd be the laughingstock of Armpit. So I was always reserved around the girls and wasn't always trying to cop a feel when teachers or other adults weren't looking. In consequence I had an unearned reputation as something of a young gentleman.

I had no way of knowing how much trouble that reputation was going to bring me.

Though East Point was all boys, the girls weren't too far away. Grimsley Hall was an all-girls school on the other side of Lake Penasaukee, and about a half hour away from East Point by car. It was closer by water. To make sure none of the boys got the bright idea to break the rules and float their way over to Grimsley for an impromptu tryst all the canoes and rowboats were counted and locked up each night. I don't think anybody would have been fool enough to try to swim it because the water in the lake was always really cold, even in August.

The thought of getting to Grimsley on foot wasn't appealing either. It was all winding country roads with no sidewalks and no lampposts. Soused farmers in their pickup trucks with gun racks in the back windows usually drove those roads at 90 mph to get to their next honky-tonk. It's too dangerous even to bike the route, which is why East Point didn't allow bicycles, just in case anyone might be tempted to try to cycle over to Grimsley. You'd probably be found the next morning along the side of the road flattened into a bloody roadkill pulp.

And if you did get over to the other side of the lake, Grimsley had its own barriers. Grimsley's fortress-like stone walls extended on three sides around the school -- all except on the side fronting Lake Penasaukee. The Grimsley dorms all had double bullet-proof glass doors manned (or I should say womanned) 24/7 by a professional security service -- once again, all female. They weren't going to take any chances. Each Grimsley dorm was like a jewelry store in Manhattan: you had to be buzzed in and buzzed out. To make their appearance even more forbidding, the guards' uniforms had those belts that went across the chest diagonally - bandoliers, I think they called them. Why the hell they needed them, we could never figure out. We concluded it was all done for appearance's sake. Because of the bandolier, the East Point boys nicknamed Grimsley's female guards the "Chastity Belts." Grimsley likes to tell the parents of prospective students that no school did more to protect the virtue of its nubile young charges. Most of the Chastity Belts were older, mature women who might have been mistaken for refrigerators if they stood still and wore white. But there were one or two that were young and smokin' hot, and we joked about wanting to be strip-searched by them. Guys always talked about getting into the Grimsley dorm after lights out, and there were stories that someone had actually done it years before, but I thought that was bullshit. We could get into Grimsley for a blowjob only in the wettest of our wet dreams. Yet but for those wet dreams we were in a desert as far as female companionship was concerned, except for the teas and dances. And except for Miss Frobisher, whom I'll get to shortly.

We had to wear our uniform dress pants whenever East Point held a dance with our "sister school," which was twice each year. Grimsley also hosted two dances, one in the winter just before Christmas break, and the second in the spring about two or three weeks before finals started. Grimsley had a so-many-inches-above-the-knee rule on skirt length, but when the girls came to East Point auditorium for a dance they headed straight to the ladies' room to hike their skirts up as high as they dared. It was as if they were all trying to out-Sailor Moon Sailor Moon. This, of course, had an immediate effect on the penis of yours truly. Little Herby wanted to rise up to get a better look at dozens of naked Grimsley thighs, and maybe even catch a panty shot if one of them bent over to pick something up. Some of them seemed to I always made sure to jerk off right before the dance to avoid making a tent in the front of my pants. That usually worked. But not always.

There were some trips to Grimsley for "afternoon teas" that were heavily chaperoned by faculty. If you had any demerits for bad behavior or bad grades, you would be prevented from going to the teas until those were all cleared up. Having the proper manners with young ladies was something we were actually drilled and tested on at East Point, so the teas were seen as a way to practice what we'd learned.

Tea and scones were served, and you were supposed to make nice conversation. They even allowed you to play bridge if you knew how. It was on one of these tea expeditions that I met Alicia, Regan and Genevieve. The only thing Genevieve French about her was her name, but she absolutely did not want anyone to call her "jenna-VEEV." That was far too American. It was always "zhonn-vee-EV." She was hot but too stuck up for me and after a while I stopped sitting with her.

Alicia and Regan were also very pretty, so I was attracted to both of them, and I guess they were to me since they would whisper to me that I was "cute" or "fine." I was more attracted to Alicia, but learned she had a boyfriend back home. Regan knew Michelle, so if started something with Alicia, Michelle would likely hear about it. But if I started something with Regan, maybe not. Both of them could talk and act in some very bossy ways, and at first I didn't like that. But I found myself jerking off to images of them being bitchy and had to admit that it turned me on.

In the end, Alicia became my Grimsley girlfriend. She had soft, dark brown hair that fell down in waves around her shoulders and caught the light in any room she entered, so that people just had to turn and look at her. Sometimes, in the winter when Grimsely had candles at its teas and she was standing in their glow, I wondered if some angel had just landed on earth. Her smile was honest and nice, and it never had that fakeness that you see in some girls who are smiling at you even when they want you to bugger off. She had perfect, just-enough-for-a-mouthful breasts. I was never a big boob fan, and if a girl didn't have too much on top that was all the better by me. And who was I to complain? I didn't have that much in the dong department.

Our relationship started at one of the teas when we found ourselves alone in a hallway at the Grimsley student center, a gothic monstrosity that must have been designed by the guy who did the sets for all the Frankenstein films. I'd been sent to get something from the van, and she was taking a shortcut from the kitchen and carrying a tray of cookies. As soon as we saw each other our eyes locked. She didn't even hesitate. She put the tray down, right on the floor, and came over to me. I put my arms around her and drew her in close and kissed her, just touching her lips at first, and then opening her lips with my tongue and entering her mouth. Our tongues went at it for about thirty seconds before we had to come up for air. One of her legs had made its way between mine, and my erection was poking her upper thigh. She started to move her leg up and down, masturbating me through my pants. I kissed her again, deeply, and then we heard the click-clack of heels on the stone floors of Grimsley and we broke away -- at warp speed, I might add. I dodged behind a floor to ceiling windown curtain and held my breath, while she bent down to pick up the tray. It was one of the Grimsley teachers asking where she'd been with those cookies. One good thing about being so scared was that the excitement in my pants subsided quickly.

About two weeks after that we arranged to go out on a date to the lone movie house in Armpit -- chaperoned, of course, by one of the Grimsley teachers. Alicia told me what she though I might be good at, telling me I should look at this or that for a career, even though I hadn't asked her for her opinion. But I felt good that she was interested, in fact, more than interested. She wanted to direct me. I was getting turned on again.

We got our tickets and went into the theater. I thought for sure that the teacher was going to sit down between the two of us, but to my surprise she sat on Alicia's left so that she and I sat together. She kept looking over at the teacher, who eventually drifted off about a half hour into the film.

"She always falls asleep," Alicia whispered to me. "That's why I always beg and plead for her to be my chaperone."

For her to whisper without risking waking up the teacher she practically had to bring her lips next to my skin and breathe into my ear, and that had it's predictable effect on my cock, which was straining to get out of my pants and listen in on the conversation. Then she reached her hand over and put it right on my crotch. And she started feeling around. I froze with some combination of surprise and raw fear.

"Are you erect?" she asked me, practically out loud in a regular tone of voice.

"What?" I wasn't sure if I'd heard her right. I'd never had a girl ask me so direct a question. "Not so loud," I said. I guess I did hear her just fine.

"Silly boy. I asked you whether you have an erection. Answer me. Is your penis erect?"

I looked over to the teacher, but she was still asleep. "Unhh...Unhhh," I stammered, "I think so."

"You think so? You only think so? What kind of boy doesn't know if he's hard or not? Take it out and let me see it."

"What??!! Here?? What if she wakes up?"

"She won't, trust me. Now don't make me ask again, of believe me I'll make you sorry for it. Take it out. Now."

I reached down and zipped down the fly on my pants, reached in and started groping around for my cock. My shorts had gotten bunched up and twisted around a bit, and I couldn't find the opening, so it was taking longer than it should have. She looked over at me and started giggling.

"What's the matter? Can't find it? Here, let me." And with that she jerked my hand back out of my pants and thrust her own into my fly. She was much more violent than I expected, and for a moment I thought she was going to rip my shorts, or my zipper, or even my pants. That would have been tough to explain. Then she got to the opening in my shorts and I felt her soft hand grip me around my shaft and lead me back out. I was so afraid that she would be disappointed with my lack of size that she'd laugh out loud and definitely wake up the teacher, not to mention the consequences to my reputation at Grimsley.
"Is that all there is to it?"

"Yu..Yu..Yeah."

"Poor baby."

"Will you not tell anyone?"

"Of course. Provided..." Here, she looked at me with a sly smile curling the corners of her mouth.

"Provided what?"

"Provided you do as I tell you and obey me in all things."

"I thought you had a boyfriend back home."

"Silly! I never said I had a boyfriend. I said I had a boy. I like having more than one, and I think your little thingy is very cute. Still, one of the things you'll have to learn is that I will be in complete command of when you may, and may not, have an erect penis. You'll have to learn that if a girl hasn't asked you to stiffen your penis for her, it's simply uncouth to present her with the fait accompli. How often do you jerk off?"

"No, I...I mean I don't..."

She quickly shoved her hand further down in my shorts, grabbed my testicles and squeezed them firmly. The pain shot up from my groin, all the way up around my sides and what felt like my kidneys. It was like I'd just been kicked in the stomach. I took in a sharp breath and lifted my butt out of the seat in a vain effort to appease her hand, to get closer to it so that she wouldn't use it to hurt me so much. She was squeezing me, all right.

"Another rule is you must not lie to me. If you do I'll punish your balls. Do you understand?"

"Yesss!" I hissed, my breath seizing in my throat with the sudden onset of pain from this girl. I learned really fast that when a girl's got you by balls, the threat is real, and submission is all that matters.

"Good boy. Now tell me how often you wank."

"Usually once in the morning and then before I go to sleep."

She answered with a quick squeeze and I did another deep breath intake and butt-out-of-the-chair move.

"Not more than that?"

"Before teas and dances and anytime we might see Grimsley girls. I don't like to take chances that I'll get an erection." She released my testicles and drew her hand out of my pants.

"That's much better. You have to be completely honest with me, at all times, as well. If you disobey me, or if you tell me something that's not true, I'll simply have to punish you. Now strip from the waist down."

"Here?? In the theater??" Was she really asking me to do this? Yes, she was. I didn't even like changing for gym class where everybody was male, but here I was being told to get half naked in a public place. My mind raced from fear to embarrassment to thoughts of being jailed as a flasher and back again.

"Don't worry. It's dark enough. No one will see."

I hesitated. She leaned over and in a stern whisper said "Either you strip off those pants and your undies right now, or by tomorrow every girl at Grimsley will be snickering over the size of your penis and calling you Thimble Watson. So you decide. Which is it?"

Without another word I quickly unbuckled my belt, unzipped my fly and pushed my pants and shorts down with one movement as I lifted my ass off the seat. When they were down around my ankles I left them there. Big mistake.

Alicia looked at me and shook her finger in my face. "I said naked below the waist. That means shoes and socks too, and pants all the way off."

Damn that was embarrassing. I'd be in trouble if an usher came down with a flashlight. But I didn't have any choice in the matter. If I wanted to keep at least some of my dignity among the Grimsley girls, I'd have to sacrifice all of it for a little while in this theater. When I got everything off, she reached down, picked everything up and put it in all in her school bag. Holy shit!!! I did not see that coming. My clothes were not merely off -- they were taken from me. If somebody saw me there would be nothing for me to do except cover up with my hands.

While these excruciating fears were racing through my mind, I felt her hand grabbing the shaft of my penis. She started stroking me up and down, at first slowly and smoothly, then increasing both her tempo and firmness. In mere seconds I forgot my fears and became as stiff as steel. I felt my scrotum tightening, and then a tingling feeling started way down between my legs. Her hand was so good, and she knew so exactly how fast and hard to wank I wondered if she might have been a boy in prior life. It was like she could tell what was going on in my groin. All I could do was grip the armrests and close my eyes. My breathing got more raucous, shallower, and came only through my mouth. Then I felt it coming and my whole body tensed up. That was a signal to her to concentrate her stroking entirely on the frenulum on the underside of my cock, near the tip. Then it hit me. I started to jerk my hips up and down to intensify what she was doing with her hand, and my first spurt of com shot out and landed god knows where. The second went up only a little bit and fell back, the warm wet drops landing on my lap and upper thigh. From there on out, it was just a dribble. Alicia kept squeezing my shaft and she stroked upwards, almost like getting the last bit of toothpaste out of the tube.

"There, doesn't that feel a lot better?

The teacher on her left let out a cough that made me panic. Here I was sitting half naked, my erect cock softening with cum dripping out of the tip, in a public theater. If that lady opened her eyes, I was completely done for. Forever.

"Yes. Can I please have my pants back now? Please?"

"Lick this first." She held her hand up to my mouth. There was cum all over it, and I licked it. It was the first time I'd ever tasted my own spunk. She pulled her hand back.

"I should keep your clothes as a punishment for not obeying my command immediately and let you get home by yourself -- bottomless. But since this is your first time accepting orders from a girl, I'll let it pass. Though it's just this once."

"Thanks." I didn't know what else to say. I was desperate to get my pants back on before her teacher woke up.

Just as I was pulling my pants up she started to nudge the teacher in the ribs with her elbow to wake her up. I zipped myself up as fast as I could, wondering why Alicia didn't wait until I was fully dressed before trying to wake up her teacher. Maybe that was more punishment, or more excitement. Maybe it was both. I was just putting my second shoe on when the teacher woke up.

"That was a nice movie," the teacher said. "Did you two enjoy it?"

"Well," Alicia said, "the acting was a bit stiff in places, and some of the smallest parts were really the best. But they managed to pull it off. Don't you think so, Henry?"

"Absolutely. Definitely pulled it off."

She put her arms around my shoulder and said "Such a good boy."

The memory of Alicia forcing me to strip in a public theater and then jerking me off right in front of her sleeping teacher -- who could have awakened at any moment -- fueled my masturbatory fantasies for weeks. The handjob was all the more exciting because of the fear of being caught. But my auto-erotic happiness was tempered by my fear that she might not keep her promise, that she might tell the other Grimsley girls about my small penile dimensions. That thought could kill an erection in seconds, but there was nothing I could do.

henry's   exposed   adventure  

Mar 16, 2018 in femdom

Tags

Search