Adventures in Dentistry | prisoner, woman | free bondage stories

The people who set up the Conclave back in the Nineteenth Century had served in the Civil War, so they laid out the grounds like an army camp, only with cottages instead of tents. Over time, this resulted in three rows of cottages in a big square, and a grassy park with trees in the middle. A blacktop road meandered around the perimeter, and every day for exercise, I jogged around the Conclave a few times. One circuit was half a mile long. I did this in the morning, before the day grew hot and the corn pollen kicked in. You know how bad it is for people who are allergic to grass? A corn stalk is essentially giant grass.

The morning jog was a good way to get my bones working, plus I always ran into people I knew. One day I was out there in the morning haze, assiduously chugging around the Conclave, when Marsha Ferguson flagged me down.

Ms. Ferguson had been my English teacher back at Boone High. She was a local girl who'd gone to State and come back here to work as soon as she earned her teaching credential. She was only about 10 years older than me. (Than I? I can never remember the rules for pronouns. But it's not her fault. She tried.) She was a slender little woman, with small tits and blonde hair. I recalled her wearing it short and curly, but today it was long and straight and pulled back in a ponytail. I had a serious crush on her in my senior year. Today, she was wearing an outfit that would never pass the principal's dress code: a tight yellow halter-top that showed her tanned stomach, and short tight white shorts. I don't know how women manage to keep white clothes so bright, especially in a Midwestern summer, when it's dusty and everyone sweats a lot. The white glow of her shorts attracted me like a moth.

"How are you, Grant? How's college? Come see what I found."

The ancestral Ferguson cottage was a two-story number like ours. I'd never been inside, but the do-it-yourself farmer construction was familiar. Each wall was a different color, for example, depending on what color was left over from painting a shed or barn. The sitting area was full of mismatched old furniture and lamps with yellowing shades. Boxes of junk covered the kitchen table.

"I got these at an estate sale. You remember Dr. Sheridan?"

"The dentist? Sure."

"He died in May. When all the furniture was gone they started selling what was left in sealed boxes. It was only $2 a pop, so I thought, what the heck, I'll take a chance. Look at this."

She opened a wooden box, about the size of a cigar box. The interior was divided into little compartments, each filled with tiny metal dental drills. Just looking at it gave me the creeps. The hand-lettered date on the lid said 1947, with a European-type 7.

"Isn't it fabulous!" Ms. Ferguson gushed. "It's like a nautilus. Do you realize someone made this by hand? I'm going to throw away the drills, and use the box to store jewelry."

Since I had nothing better to do, and because I liked the way her nipples poked through the thin yellow fabric of her halter, I started going through boxes with her. Most of it was antique dental paraphernalia. A jar of discolored teeth. Plaster casts of gums. Cryptic pieces of metal. "I never suspected you were into dental supplies," I kidded, peeking at her chest. The crush had died down at college, but hanging with her reminded me how it began. She could make the most boring assignment seem interesting.

She smiled and shrugged. "I've always been interested in old tools. I used to go out in the barn and look at Granddad's old farm tools and try to imagine how he used them. Do you ever get nostalgic about material objects?"

"Hey, come on, it's summer. No essay questions."

She giggled. I felt very mature, bantering with my former English teacher. She sure was cute. And as we rooted around in the boxes I couldn't help noticing that she would touch my arm to make a point, and brush her hip against mine. The protective force field I remembered from high school seemed to have vanished. In the realm of fantasy I would have jumped her bones in a minute, but the social reality of our small town made that risky. A couple of years ago, the assistant football coach lost his job because he was spotted having lunch with a student in another town. From what I heard from other kids it was completely innocent, but the adults got suspicious and basically ran him out of town. I had nothing to lose, but I didn't want to cost her her job.

Then I lucked out.

She opened a larger box, and contemplated a tangle of metal. A pair of handcuffs? A set of manacles connected by a foot or so of chain? A red ball on a leather strap? Holly cow! Kindly old Dr. Sheridan was a pervert!

"What in the world is this?" Ms. Ferguson asked innocently.

I glanced at her, but she seemed genuinely puzzled, like the asexual dweebs who were selected to be hall monitors and crossing guards. Well, she had spent her entire life living in small towns and teaching farm kids. I decided to get creative. "Maybe Dr. Sheridan had to work on prisoners from the county jail. He was the only dentist in Boone County, wasn't he?"

"Yes…"

I picked up the handcuffs and tried the key to make sure it worked. It did, so I calmly flipped open the metal C's and took her slender right wrist and snapped it on. Click! I squeezed the cuff tighter, click click click on her warm little wrist, until it couldn't come off. "I suppose when the jailers brought Dr. Sheridan a prisoner to work on, the prisoner had to be restrained." Gently I guided her right arm behind her back, then reached around and brought her left arm back too. Click on the other wrist! Just like that, she was handcuffed with her wrists behind her back.

She glanced back over her shoulder and moved her arms around to test her restraints. An odd expression flitted over her face. She reminded me of a woman testing a new perfume at Marshall Fields and trying to decide if she liked it. I kept my own expression neutral, disinterested, like a scientist testing a hypothesis. In fact, I was wildly excited. She was a small, delicate woman, and handcuffing her made her seem even smaller, more vulnerable. It also pulled her shoulders back and made her dainty little tits stick out a bit more.

She wasn't objecting, so I decided to up the ante. "Let's see if the manacles work," I breezed. She spread her legs for balance and stood calmly as I knelt and attached the metal loops to her bare ankles. This put my nose about four inches from the front of her tight white shorts. Click click! Click click click click!

Ms. Ferguson took an exploratory step to test her hobbled gait. She walked a circle in tiny steps, the chain swishing on the linoleum floor. "So this is penal dentistry," she mused. "Fascinating. Who would have thought?"

"You see? Even if a prisoner were left unattended, she couldn't run away."

"I'm certainly not going anywhere," she said brightly.

She seemed to be enjoying the situation, so I decided to go all the way. I picked up the ball gag. "Open wide."

She looked at it, puzzled. "Now how would a dentist use that?"

"I bet the jailers did. During transport. To keep a surly prisoner from cursing the honest citizens he passed on the street."

"Of course." Ms. Ferguson opened her luscious mouth, and accepted the red ball. Her eyes widened as I pushed it in with my thumbs. Then she turned away so I could fasten the straps behind her head. The ponytail conveniently held her hair out of the way. I buckled the straps snugly. Then I took her bare shoulders (mmm, her warm shoulders) and turned her to face me. What a fetching package!

"NNNggggRRRRzzz," she said.

"Gag seems to be working." I seized her chin and turned her head left and right as if checking the fit. I loved the situation of having this attractive blonde in my clutches. I could do anything with her. Her blue-grey eyes regarded me serenely. The only problem with the gag was that I couldn't read her expression. Would she mind if I went farther? Or was I pushing my luck? I could be totally misreading her compliance.

Someone knocked on the door at the other end of the cottage. "Marsha? Are you in?" It was a woman.

Panic flared in Ms. Ferguson's eyes. I didn't recognize the voice, but she sure did. Instantly my teacher shuffled to the stairs and hobbled up to the second floor with surprising speed and agility for a woman in leg irons. Not knowing what else to do, and to catch her in case she tripped and fell, I followed her up. The second floor was her bedroom: one large room dominated by a big four-poster bed.

We stood in silence, shoulders hunched under the low roof, as the caller knocked again. "Marsha? Marsha?"

I understood her fear. Since everyone knew everyone in our small town, things were very relaxed at the annual summer Conclave. No one ever locked a door. People walked into each other's cottages uninvited. If someone caught the high school English teacher in a compromising situation with a former student…

Finally whoever it was left, and Ms. Ferguson relaxed.

She mumbled something and turned her head away, so I unstrapped the gag and pulled out the ball.

"Thanks," she said. "That was Gloria Dixon. I just cannot stand her. She is the meanest woman!"

"I've heard my mother talk about her."

"Just plain mean!"

Ms. Ferguson sat down on the edge of the bed. I glanced around, curious about the room, which of course I'd never seen before. I noticed lots of feminine touches, like a bowl of poupouri, and a Raggedy Ann doll on the dresser. It was certainly different from the austere intellectual image she'd tried to project in class. It was frilly! Ms. Ferguson was a closet femme. Between the low ceiling and the feminine decoration I began to feel intrusive.

"I'll get the keys," I said reluctantly.

"Oh, no hurry," she sighed.

"Really?"

"It's an interesting sensation. Being a dental prisoner, I mean. It makes me so... helpless." She lay back on the bed, then swung her legs sideways so they were off the floor but her shoes extended over the end of the bed. "Grant, would you be a dear and take off my shoes?"

Being a good former Boy Scout, I hastened to obey. I took off her sandals and plopped them under the bed. As long as I was there, it seemed natural to sit down on the end of the bed and caress a foot. Kinda neighborly like, you know? She sighed with pleasure and parked her other foot on my thigh.

"I do believe you're enjoying this, Ms. Ferguson."

"I can't help thinking of that Willa Cather novel we read. Remember the scene in the meadow?"

"Come on, it's summer."

"You're right. And you're not my student any more." We considered the implications of this. She wiggled a foot into my lap and brushed it against my stomach. "Do you think Dr. Sheridan ever took advantage of his patients? While he had them restrained, I mean?"

"He'd be a fool not to. Especially the pretty blondes." I took off my shoes and socks and lay down facing her, and we kissed. Her mouth tasted fabulous. While we kissed I played with her tits through the fabric, and she whimpered and kissed harder, so I untied the halter top and flung it aside. Then I kinda went wild on her tits, kissing and licking them, trying to suck those yummy little cupcakes right off her body. She gasped and thrashed and egged me on.

She didn't object when I unzipped her shorts and fondled her ass, so I got the key and unfastened her manacles long enough to lose the shorts and panties. Then I fastened the chain again, because I liked having her my prisoner. She was now nude, except for shiny steel. I stripped too, and showed her my erect penis. "Time for your oral exam."

"Oh my goodness. Dr. Sheridan, is this the normal procedure? The deputy said I was going to get a cavity filled."

"Listen, jailbird. The deputy is an alkie. He dropped you off and headed straight for the tavern. For the next hour I fill whatever cavities I want. Got any problems with that?"

"No, Doctor. I'll do whatever you say."

"Then open wide." I perched at the head of the bed, and she rolled over and wiggled until her face was at my cock. She licked it all over, then concentrated on the head. I loved the slick feel of her tongue, and I loved knowing whose tongue it was pleasuring me. I discovered the pony tail made an excellent handle for aiming her face at whatever part needed more stimulation.

When I was ready to burst, I rolled her face down and climbed on her back and ran the head of my cock up and down her slit. Mmmm, was she juicy! I teased her a little, then plunged in. Oh, what glorious thrashing! I was afraid the Gloria Dixons of the area would hear her yell, so I gagged her with a pillowcase. Her face turned red and her eyes bulged out, like a boiler about to explode. And soon enough we did explode. Both of us.

Eventually we came to. Was it afternoon already? The ponytail was shot, so I pulled out the band and fanned out her hair. I love playing with women's hair. She mumbled something, but I just kissed her cheek above the gag and rolled out of bed. I tried to stand, but ended up sitting. Every cell in my body felt drained. God, I love good sex.

While I was up there on the second floor, there was something I had to check. There were a number of places to look, but the nightstand beside the bed was the obvious place. Sure enough, the bottom drawer contained her sex toys. Several vibrators of varying gauge. Some kimono sashes and belts and pieces of rope. And the decisive clue: three Harmony bondage magazines.

"MWUMWMU!" she sat up, glaring.

Without deigning to explain myself, I removed the manacles and tied her ankles to the foot of the bed with the kimono sashes. I winged each leg out, so she was open nice and wide. Then I did the same with her wrists, tying them to the posts at the head of the bed. When I finished she was as nude as before, only tightly spreadeagled. I patted her honey-toned bush affectionately, and found myself caressing her slit. It was slick with our love juices. Her cunt was a whirlpool, sucking me in. I felt drugged. I bent down and licked a few times, high on the smell.

"Just for the record, I don't appreciate being taken for a fool," I said between licks.

She arched her eyebrows innocently.

"The dental stuff was old. The bondage gear was new. That wasn't Dr. Sheridan's. That was yours. You planted it there."

She had the integrity to blush. I'd never seen a nude woman blush. It started in the shoulders and worked its way up her neck.

"I'm glad it was me you chose, because I had a great time, but I think you need a lesson in proper student-teacher relations."

I worked a pillow under her ass to raise it and display her cunt. Then I selected the biggest vibrator. It was obscenely huge, a pink cucumber on steroids, the kind of thing you give someone as a joke. I rolled it on her stomach to warm it up, and her eyes went wide. "NNNNN! NNNNNN!" she shook her head wildly.

"Come on, Marsha. Think of it as a chance to really get to know a classic tool." I put the tip to her vagina, and twirled it to distribute the lubrication. Then I gradually worked it in. She squealed and thrashed and practically levitated off the bed, but she wasn't going anywhere, not the way I'd tied her. When it was in I had to hold it in place, because I could feel her trying to squeeze it out. The blunt end thrust against the palm of my hand like a periscope coming up, and when I pushed it back in she moaned like a log being split by a wedge.

I could have used three hands for the next few steps, because I hadn't planned carefully enough, but essentially I fastened one belt around her waist and ran another from front to back, anchored on the first, and used it to hold the vibrator in. Securing the waist belt was easy, since that's what belts are designed for; the engineering problem was making sure the one securing the vibrator didn't let it slip out. When I was finished the huge dildo was in that happy place where I'd just been, and it wasn't coming out until I released it. I stroked her smooth inner thigh and contemplated my prisoner. She gazed back at me with a mixture of lust and frustration.

I knelt and licked her right breast until the nipple firmed up. "Put away your books, Marsha. This is a pop quiz."

"Mmmmm?"

"I want you to compose an essay. A mental essay. I want you to think about how you had a crush on me in my senior year, and how you ached to fuck me, and how you lay awake in your bed every night, tossing as you imagined having sex with me."

"HHmmm."

"I want you to think about how you found it difficult to take your eyes off me, and how you kept sneaking glances at me, and how you hung on every word when I spoke in class. How you thrilled when I approached your desk to ask you a question, and how you found it hard to stick to your lesson plan when I was in the room."

"UMFF!"

"This is your assignment, Marsha. You have, let's say, two hours to complete it." I reached down and turned on the vibrator. She squealed, and tensed as if shocked with electricity. Her body arched, her pelvis raised off the pillow. Muscles appeared in her thighs as she strained against her bonds. A bit more of the blunt end of the vibrator eased out of her as she strained to expel it, but the belts held it in. She thrashed around as much as the spreadeagle allowed, but she clearly wasn't going anywhere.

"I'm going to finish my exercise now. I'll be back in two hours to hear your answer. And don't peek at anyone else's paper, OK?"

I squeezed her left tit, and went downstairs. Thinking: walk a few laps to rest up and get the blood going, and then pay her another visit. A line from a Shakespeare play she made us read came to mind. Henry V: Once more unto the breach, dear friends. Once more unto the breach.