The Doctor's Daughters Pt. 01

"Scott, I wasn't finished. Because of elevated nature from spanking to caning and the potential to not see the full damage with a cane, all strokes in this house are given on bare flesh. Decide if you want to continue."

He didn't want to drop his pants after such as embarrassing ordeal earlier, but this rule also meant that he would cane Sally bare. He also reasoned that as humiliating as it had been Dr. Kathy had already put a finger in his asshole and seen him ejaculate. He didn't have much to hide. He shamefully put his head down and lowered his pants and underwear down to his mid thigh.

"Count off!"

"One!"

"Two!"

'Three!"

"Four!"

"Five!"

"I will stop at five since you haven't actually done anything wrong. Stand up put your arms behind your head and face me."

He turned around obediently with his penis fully displayed. After a moment he started to falter.

"I'm sorry I almost forgot you require a cane for stability. You may get dressed now."

He hastily complied.

"Dr. Kathy."

"Please I'm not wearing that hat right now, just call me Kathy unless I'm spanking you again then it's ma'am."

"How will I know how to match the intensity you caned me at?"

"We will have to practice. Typically I do not submit to discipline and would use a volunteer to teach, but we are working on short notice and I did see you exposed unfairly. This one time I will allow you to use that cane on me that I haven't felt in twenty five years, but be aware it will be the only time."

He inspected how the handle attached to the smaller piece of wood in surprise. There was more to his parents than he realized. Kathy turned around, dropped her skirt to her feet, and bent over the table. She wore modest black lace panties with nylons so Scott couldn't see much.

"Oh, I thought that -"

"Yes, Scott?"

"Uh, never mind ma'am."

He softly caned her.

"Not hard enough, Scott!"

He added more speed with the flick of his wrist.

"Better, but what were you going to ask me a minute ago?"

"It's just that... well you know I uh thought that uh,"

"Spit it out young man!"

"I thought all caning was done on the bare?"

She smiled over her shoulder and lowered her panties to her knees. She was much older than him, but he still took notice of her labia folds neatly framed beneath her buttocks. He landed another couple strikes and she leaned forward even more opening her crevice and revealing her hairless asshole. After about seven strikes he'd landed three correct intensity strikes in a row.

"Stand up and face me with your arms behind your head!" he ordered not very convincingly.

She turned around as ordered and he saw that unlike the small strip he saw on her daughter Lisa earlier she maintained a neatly trimmed graying bush above her protruding lips.

"You may get dressed," he said after realizing he was staring.

She smirked and put her hands on her waist.

"I hope you enjoyed the view because you will not be seeing this again unless I decide to personally teach you another lesson. Oh, and one more thing..."

She turned and pulled her panties up with her ass bent over accidently giving him one last glimpse of her pink rosebud. Then she sat down without putting her skirt back on.

"You knew about the bare rule for caning, but didn't have the confidence to enforce it, therefore, you need to be punished for your weakness. Since it was your first time I won't do it front of the girls, however, I am going to need you to drop your pants and get over my lap."

He complied, feeling very vulnerable even in his briefs. Kathy pulled his briefs down and trapped his erect cock between her nylons. She then administered ten hand spanks to his ass.

"Dismissed for dinner! Oh, and put that hard on away, I don't want you exposing yourself to my youngest daughter. "

Dinner was an awkward affair, Sarah's cooking was spot on, but it was the first time Sally and Scott had seen each other since Kathy kicked her out of the exam room. Sally was dressed in a white blouse and black skirt. Her usual fun personality was subdued as she picked at her food not really eating anything. When the meal concluded Kathy ordered everyone into the den.

"We will start in order of lowest severity. Sarah dear step forward." The young woman nervously stood in front of her mother awaiting judgment. Scott couldn't imagine that Kathy would bare her eighteen year old daughter in front of him when she was clearly more protective of her. "You fell behind on the kitchen chores earlier this week so you will receive ten spanks with my hand over your panties. However, since you've otherwise been such an angel this week and we have company. I will administer them privately after we are done. You may step back in line."

"Yes, mother!"

The girl breathed a sigh of relief and stepped back. Scott couldn't help but notice the other girls looked jealous.

"Lisa, you have already been corrected for what happened at work. However, I couldn't help but notice our guest's pubic area was a little more tidied this afternoon. Technically that was on your day off, but all I asked you to do was put the catheter on. You took it upon yourself to shave him isn't that right?"

"Yes, mother."

Scott looked more embarrassed than Lisa at this discussion of his pubes. Especially the admission to Sally that he had exposed himself to Kathy after the exam had concluded.

"Sarah bring me the shaving bucket. Lisa assume the position."

Lisa took off her skirt and lowered her panties. She got on the bench in the middle of the room with her legs spread wide apart giving his Scott his first look at an opened pussy. Her mother shaved off the landing strip and slight stubble around her lips.

"Change position!" Kathy barked.

Lisa quickly got up, knelt on the bench and pulled her ass wide apart while Kathy shaved around her anus. Scott's already large bulge lurched at the display and Sally took note of the reaction.

"I kind of assumed you were an ass man, but you look like you want to eat the hole package." She jokingly whispered in his ear. He didnt laugh at her pun, but the whisper combined with her hand running down the front of his pants made his predicament even worse.

When Kathy was done, Lisa presented herself to Scott again with her hands behind her head and a newly bald pussy to apologize. That left only Sally.

"Sally, step forward! I've divided your punishment into parts for each offense.  For the skin exam you will be naked for the duration of your punishment, for the observed drug test you will be tied in place until you wet yourself, for the prostate exam you will receive a ginger plug followed by an enema. For using his anxiety against him and harming my patient you will receive twenty five strokes with a cane. Finally for withholding our mother daughter relationship from him, you may serve him, but you will not be allowed to orgasm today. Do you understand?"

For the first time Sally looked a little scared nodding.

"Yes, mother."

She disrobed in front of Scott for the first time revealing firm breasts, a toned abdomen, and bare pussy lips. She walked over to the bench in the middle of the room which was covered by disposable padding after Lisa's punishment, and knelt so that her head was down, her pussy was visible, and her cheeks were spread wide enough to reveal her tight puckered asshole. Her sisters tied her in place and her mother asked what order she would like the punishments in.

"Strokes first, then the ginger, and the enema to wash it out. I had a lot of water at dinner so I suspect I'll lose bladder control during the figging, and I don't want to have to hold the enema for very long."

"Clearly this wasn't a new thing for her!" Scott thought.

"Wise choices indeed, but then again if you'd been wiser sooner you wouldn't be in this mess." Kathy said inserting a lubed piece of carved ginger with a wide base into her daughter's rectum out of preferred order.

"Scott begin!"

Scott began administering strokes.

"One! Two!"

Scott noticed each blow caused Sally's asshole to tighten on the ginger. But due to the ties she could do very little wriggling other than swaying her reddened ass. 

"Sixteen! Seventeen!"

At this point Sally started to cry and wet herself. The mat caught the dribble, but Scott wondered if the punishment was going too far.

"Do you want to use your Latin word?"

"No! Pardon my French, but fuck off with your weak ass strokes!" She defiantly replied.

He brought the cane down harder.

"Eighteen!" she wailed.

He lashed down at similar speed for the next few strikes and bruising started to occur on her already crimson ass.

"Twenty three! Twenty four! Twenty five!"

Scott lowered his cane, and now that the adrenaline rush wore off he felt rather awkward standing there with his girlfriend crying bare assed in front of her mother and siblings.

"Should I untie her?"

"No, she's not done yet. Sarah fetch me the enema equipment."

Kathy donned latex gloves and pulled the ginger root from her daughter's asshole. Applying more lube she inserted an enema nozzle and hung the bag. Sally moaned as it filled her up. Once the bag had dispensed. Kathy pulled the nozzle put and placed a large plug in Sally's ass.

"The session is over! Release her and you are dismissed except Sarah you are to report to my study."

The two sisters untied Sally and quickly made their exit.

"Sally receiving the enema is the punishment, not expelling it, so you may dress now and take Scott home. It was very nice to meet you young man my clinic will not be billing you for services this time. "

"Thank you ma'am."

And with that Kathy walked out.

"I'll take you home," Sally said.

Sally and Scott had been dating for about three months, but had been taking it slow in part because of Scott's shyness. Sally had never seen the inside of Scott's home, and obviously she had kept much of her family life from him. She did know he owned the third story of a brick building that housed an antique mall on the bottom level, and a large salon and spa on the second. She also knew he'd received a large inheritance that allowed him to live on dividends, but he wasn't a big spender.

"Thanks for the ride... look I'm really sorry if things went to far back there." He kissed her and started to get out.

"Wait! I'm coming up with you, and no I'm not mad...I just hope you didn't hurt your back more than my ass with those pathetic swings."

She grabbed a duffel bag out of her car.

"Is she planning on staying the night?" he wondered in surprise. He wasn't planning on showing her his place yet, but felt some of his confidence waning without Kathy present to make him feel in charge. They took a hand operated elevator to the third floor to save Scott the extra steps. He could manage stairs, but it was easier not to with his cane.

He unlocked the door and to Sally's surprise the whole floor was opened up with no walls save for bare studs in the massive space. She could roughly discern the layout from the open beamed walls.  His large bedroom area was in one back corner, with a walk-in shower, jet tub, urinal, toilet, and double sinks. Then there was a guest bedroom planned across from it, what was probably an office overlooking the cove on one side, and a guest bathroom with laundry attachments. There were also two rooms that didn't appear to be developed.  The kitchen and living room looked to be staying open. He'd turned an entire factory floor into a single person condo! She led him into the bedroom and put her bag down.

"Charming." she said gesturing at the master bathroom toilet in plain view.

"Uh, sorry, I wasn't really planning on having guests yet. I'm redoing all the walls in original brick and the construction crew is on a holiday break. I can't lift much myself."

"Sounds lovely, but listen up. This enema is getting really uncomfortable and expelling it front of you is not going to happen! Go kneel on the bed with your back turned until I give you permission to turn around."

He complied. He didn't really know why he complied, was it because he wanted to give her privacy or was it because she was really still in charge? A couple minutes later he heard the toilet flush.

"You can turn around now."

He turned over so that he was now lying on the bed facing the future master bathroom. To his surprise she was completely naked.

"You can watch me take a shower, but don't touch yourself."

He nodded in excitement. She put on a show of soaping her breast and pussy before spreading and washing her ass.

"You know maybe you should just do a half brick wall for the bathroom, a glass wall in front of the shower might be fun..."

A hand inched towards her clit, but then she stopped.

"Oh, yeah I'm not supposed to cum today!  Guess you're not getting your first pussy yet."

She turned the shower off and dried herself. Walking over to his bedside she reached into her duffel bag and produced a bottle of lube.

"Still I can't imagine your virgin cock will last long enough in my ass to make me cum... especially not after the saw the way you were staring at my sister's asshole earlier. Besides I believe I'm supposed to service you master." She said sarcastically.

She yanked his pants and underwear down! Taking him into her mouth she bobbed up and down until he was at full length.

His cock looked a little over six and a half inches. Not bad! She thought. She bent over standing up and grabbed two of the exposed beams for support.

"Lube my hole up and fuck me in the ass like you mean it!"

Needing no encouragement he proceeded to fuck her from behind. The plug had widened her tight hole enough to enter. Watching her ass cheeks slam against his pelvis he couldn't resist the urge to slap them.

"Yes, spank my ass!!"

He felt in charge again for a moment before exploding his cum into her rectum. She pulled him out.

"Too bad we couldn't keep going for my sake, but rules are rules. I need to rinse my ass out and if you want your cock anywhere near my mouth again you better rinse off."

They showered together for the first time.

"Uh, Sally I need to pee could you turn around while I use the -"

"Don't be silly just pee in here!" She said grabbing his soft dick and pointing it at the drain. He nervously complied, again not sure why he was taking orders when he was supposed to be in charge tonight. They got out and Sally made sure Scott took his medications before passing out naked in each other's arms.

When Scott woke up he noticed something wasn't right. His hands were tied to the beams above him and his legs were tied open to the beams on the remnants of the side walls completely exposing him. Sally sat in front of the bathroom facing in with her sketch pad. 

"Sally! What's going on?" he mouthed.

"Oh just doing some sketches in case we ever want to update that book my mother gave you. I noticed you had some marks on your ass in the shower, so my mother must have trained you. Naughty boy, exposing your cock to my mother outside the exam room!"

He blushed and she stood over him.

"I've gotten you off twice now and it's after midnight so you're going to have to make it up to me before I give you any attention. Did my mother teach you the Latin word?"

He nodded as she climbed over him and starting lowering herself onto his face

"Good, now lick my clit until I say stop!"

Scott licked and sucked on her nub until she bucked violently against face.

"Oh yes!!!" she gushed.

"One thing still confuses me. I didn't see any marks on Lisa earlier, and my mother would never let you cane Sarah cause she's so fucking special, which must mean..."

The look on his face gave it away.

"I thought so!" she grinned. "I bet you got hard checking out my dear old mother's asshole too!"

His face burned with shame at the true accusation.

'Well if you like ass so much...I'm clean, you can stick your tongue where your cock was earlier!"

She smothered him in her cheeks and he lapped at her asshole until he partially impaled her with his tongue. Sally started whimpering and lowered herself down.

"The score is even, but I don't feel like untying you just yet. I mean what would you even spank me for later? I haven't been that naughty yet. I suppose you can always use the safeword, but if you do everything stops and you don't get to cum so use it carefully. Do you understand?"

"I understand."

She slid a blindfold over his eyes. But he didn't feel anything. Shortly after he heard a knock at the door.

"Sally, what could be so emergent that you need me to rush over to a strange address after midnight without telling Mom? Wait why the fuck are you naked?"

The grumpy voice sounded like Lisa! He groaned knowing Sally would probably show her sister his naked body all tied up.

"Love you too sis! I know it's late, but I was wondering if you'd give me some advice about male anatomy doctor."

"What are you talking abo-? Oh!" Lisa gasped as she stepped in and saw Scott tied up across the condo with his flaccid penis on display.

"Oh, I'm rather familiar with this anatomy! I practiced grooming it earlier. Why don't you don't you don some latex gloves for this lesson, start with his head, and work your way down?"

'You got it sis!" Sally replied snapping her exam gloves while gently licking his head and piss hole.

"Oh, that's hot! Now give his shaft some attention."

Sally ran her tongue up and down his shaft for about half a minute before Lisa interrupted.

"Don't let him cum too fast! Now show his testicles some love."

Sally sucked each testicle individually then licked his scrotum. Scott moaned in pleasure. He was embarrassed that Lisa was watching, but so turned on!

"Oh, Sally my panties are so wet! I'm glad you called. Okay, he's probably feeling very sensitive so if you want to continue he might need a break."

Lisa pulled a cock ring out of her bag and eased it onto him.

"Smart! Okay, if you lift his scrotum up you'll see his perineum."

Sally lifted his scrotum to the side so Lisa could see and dove in with her tongue. Scott's anxiety started to fade and as he moaned loudly.

"Sounds like somebody is enjoying himself. That expertly shaved hole is his anus and judging by the fluids on his exam table sheet I'd guess his is very sensitive." Lisa said still role-playing the anatomy lesson.

Sally gently flicked her tongue across his asshole, causing him to twitch uncontrollably. She changed tactics by circling her tongue around his hole before it started to enter. Suddenly she stopped.

"You're such a little freak in bed Sally!" Lisa chided her.

"Oh like you're not touching yourself! I bet you're close to getting off too. Everyone knows you like being a peeping Tom more than you like getting laid you perv."

Scott heard her Lisa moaning as Sally took him partway into her mouth.

"I think you've seen enough of my boyfriend, plus it's rude to talk with your mouth full." Sally joked. "But before you leave I think it would give poor Scott here a huge confidence boost to see how turned on he's made you."

"I don't know, he already saw me half naked earlier. I'm more into watching than being watched."

Scott felt a tinge of disappointment.

"Oh, that's really too bad! I guess we won't bother you like this again." Sally slyly returned knowing she held all the cards over her voyeuristic sibling.

"Ok, fine I'll do it!

She pulled the blindfold off Scott and lowered her panties under the nightgown she rushed over in.

"Don't forget his prostate."  She reminded her sister.

Lisa was now sitting on the bed masturbating with her nightgown pulled up. He admired her bare pussy as she rubbed her clit. Meanwhile Sally slid a nitrile gloved finger into his rectum and curled into his prostate causing him to swell into the cock ring. Lisa was rubbing faster now.