Tuesdays with Mr. Tickles

Cindy waited on her knees, focused on Mr. Tickles’ every gesture. Her arms were bound, her nipples were tingling and the big ball-gag was making her drool. She couldn’t pronounce her safe-word even if she wanted to. She could only wait and stare; wondering whether he would put her on the Symbian again, tickle her with the feather duster, or give her what she really wanted. She blinked at his sturdy erection, longing for it. Drool stretched fell to her chest, then slid slowly downward. It was so ticklish.
This wasn’t something she could imagine breaking off. Neither of them could.
“Cindy?” he asked from the couch.
“Mm-hm?”
“Are you ready to try something new?”
She nodded.
“Good. I’ll just fetch the lube. When I get back I want your cute little bottom propped-up in the air for me, okay?”
“Nn-gay.”
“I'm going to fuck you in the ass, okay?”
“Ong-Gd…. Hhmno. Riehry?”
“Yes.”
“Hm-mm.”
“Yes Cindy. It’s time.”
She fell silent, imagining how it might feel to have his cock in such a tight place. She’d never tried it before. She told herself he would be patient; go slow. Eventually she murmured “N’gay,” and nodded tentatively.
He stood and sauntered from the room, leaving her to improvise a method of lowering herself to the carpet without falling on her face. She knew he’d be back in a matter of seconds. She wanted to be obedient as ever, so she knee-walked in a half-circle and then bent over. When her forehead touched the floor she shuffled her legs backward and apart and relaxed her torso so that her bottom was nicely splayed.
His footsteps approached. She shut her eyes and let out a long, low whine as lube began to pile up on her tiniest orifice.
“Good girl Cindy,” he whispered. “You stay just like that.”
Her mind raced. She tried to rationalize the events of the past few months.
She’d originally chosen Mr. Tickles’ name from the list at the elder-care agency because it made her giggle. It sounded so harmless. Her guidance counselor at college had told her volunteering in an elderly person’s home was an easy and safe way to pad her resume for medical school, especially compared to working at a big public clinic downtown. So she signed up with an agency and took the bus to Mr. Tickles’ house for an interview. It had gone well. His old fashioned charm had been on full display as he regaled her with stories about his career. He’d been one of the few straight fashion photographers on the Eastern seaboard during the peak of the color film era, before digital came in and, as he put it, “ruined everything.” Given his background, she couldn’t help feel a twinge of pride when he mentioned she was pretty. They both agreed she would visit him weekly. They chose Tuesdays because she didn’t have any classes then.
She never imagined it would turn out like this.
After their first few visits he’d given her a shiny new bicycle so she wouldn’t be dependent on the bus. Next he started ordering outfits for her on-line. The first was a sundress two sizes too small that barely covered her butt. He made her wear it throughout that visit despite her blushing objections. The following week it was a silk miniskirt with Japanese-style closures up one side that revealed peeks of skin to her hip. He insisted on high heels too, no matter that she was doing his housekeeping and cooking. Every week there were new clothes. Given his background in the fashion industry, she felt compelled to listen as her coached her on how to dress, pose and wear her hair. She soon found herself performing little cat-walks for him while he kibitzed from the couch. Her outfits became increasingly risqué and she got addicted to his praise, until by the eighth visit she found herself quite happily perched atop his lap in nothing but stockings, stilettos and a mini-apron that didn’t cover anything.
His soft hands roamed her most private places. These ‘tickle sessions’ became the highlight of her week. At first she couldn’t believe what she was doing, but her body responded so positively that resistance seemed impossible. She found herself clutching the reliable tent in his trousers as he fondled her. It seemed a natural. One afternoon in April he at last unzipped his fly and pulled it out. She stroked him tenderly, blushing and grinning like a teenager. Then she pressed her small boobs to his face so he could suck them. Minutes later she slid down between his knees and gave him a slow, adoring blowjob. It lasted much longer than she was used to, and when he came in her mouth it felt like a prize. She barely contained her delight long enough to swallow.
Thereafter the anticipation of seeing him each week distracted her from schoolwork. She couldn’t study. At night all she could think of was Mr. Tickles and the way he made her feel. When Tuesday arrived she pedaled to his house an hour early, stripped herself naked and offered him a blowjob. He wasn’t even fully hard yet and by the time she finished it was a sloppy mess. With the tang of his seed still on her breath she asked if she could visit more often. He agreed on the condition that she keep it secret. That afternoon they had sex for the first time.
It became a ritual. She’d never been with a man who could last so long. He would sometimes fuck her for forty-five minutes straight, giving her to orgasm after orgasm before finally ejaculating. She crawled back for more every other day. His derelict old house began to feel like her second home. It was a magnificent escape from the tedious nightmare of her pre-med studies.
Now the school year was almost over; she had only a month left before final exams and the end of her contract with the volunteer agency.
She suddenly felt him spreading her butt cheeks wider, prying them apart with his thumbs. It jolted her out of her reverie. The tip of his cock nudged her anus.
“Uhnng,” she moaned as he began to push in, stretching her slender rectum wider than ever before. Once the crown of his cock was inside he paused. She could feel every millimeter of movement. Slowly he began to creep further inward. It was so intense she wanted to pee.
“N-goh, n-gohd, n-gohd!” she panted. The clothespins on her nipples dragged against the rough carpet as she squirmed. Her clit felt throbbing and sensitive. She was one simple touch away from another orgasm. His cock kept pushing in, dilating her backdoor. Her eyes began to water.
Once wedged deep inside, he grabbed the rope securing her forearms together and used it like a bridle to control her. He began to thrust, and soon reached around to rub her clit.
Her mind flooded with the white light of climax. Her legs quaked and her stomach fluttered. Her asshole pinched rhythmically around him. Her leaking juices mixed with lube and dripped to the floor. She wailed as she came, curling her toes. He grabbed her hips and increased his tempo, pushing deeper until his balls were slapping her pussy. She coughed into the gag, arched like a whore and came harder, grinding herself onto his cock as the vacuum tightened inside her.
He lasted and incredible five minutes like this, pumping in and out as the lube frothed white. Carpet-friction peeled the clothespins from her nipples. It was so intense that she peed near the end, right before he came. Her little body had never been worked so hard.
Afterward her tight seal kept him in, even as they slumped to the floor and went limp.
“My God,” he said. “That’s my new favorite.”
“Mm-hmm,” she sighed. Her interior was abuzz. Her skin was slick.
He rose from her back and slowly untied the rope and unbuckled her gag. She curled to one side as soon as she was free, closing her eyes to savor the aches and pains. The novel sensation of cum inside her ass made her smile.
He stood and retrieved the feather duster, then he began tracing her legs with it, from ankle to tailbone. Her smile became a giggle, then a squirming laugh. She rolled over and tried to fend him off. She couldn’t take it.
“Get up,” he said. “We’re taking a shower.”