by Jolie Du Prè
I stared at her outfit. “What brings you here?”
“Thelma’s an old friend. Let’s just say we’ve shared occupations in the past. I offered to help her out with this event, her first, to loan her, shall we say, some furniture, to give suggestions if needed, to kick ass, if warranted.” Her delicate, but throaty, laugh bode authority. “We’ve been planning this affair for some time now.” She cocked her head and waited.
“Same thing,” I replied, “I mean, not the same business, er, well, I mean, we’re old friends and I’d like to support her endeavor.”
“I’ll bet you could turn a few bucks by turning a few tricks, Mr. Sexy Man.”
I achieved a full blush.
Sherry leaned into me. “Let’s continue the discussion at my place.” She stroked my crotch.
Goose bumps erupted on my body. “I’d like that. I’d like it very much.” My cock quivered in its leather cage.
“Good. I’ll leave now and warm the place up for us.” She handed me a red card with gold embossing. I looked at the address and tried not to raise my eyebrows. “I’ll say goodbye to Thelma, and be on my way.”
“I’ll walk you to your car,” I offered.
“Not to worry. I’m parked out front.” She gave my arm a light tap and walked toward the bar.
I stared after her. “Wow!”
She and Thelma whispered a few words, and then hugged. Heads turned as Sherry made her way through the crowd.
Thelma plunked her forearm across the bar’s damp wood, and leaned into the bartender. He looked up from the beer glass he was wiping, followed her gaze as Sherry strode through the open door, and nodded. I hurried to the locker room.
I changed and put my right foot into my left pant leg only once. I dashed to my car, glanced at my San Francisco map, nodded, and fought my way through downtown late night traffic to Pacific Heights. My car had enough gas to haul me there, but my net worth wouldn’t permit me to roost. The tops of the twin towers of the Golden Gate Bridge, red lights throbbing, rose through the fog, which glowed with yellow and white light scattered from the bridge’s spires and roadway. Surreal. Almost like a theatrical production. Lost in my tangle of thoughts, I hadn’t turned on the car radio, set permanently to my favorite classical station, or stuffed the impatient jaws of my CD player with my opera-of-the-day selection.
I turned into an upscale neighborhood and searched for Sherry’s address. I stopped peering at numbers when I noticed a brightly lit yard and house in the distance, a beacon in the otherwise dark neighborhood. Although closely spaced, the homes were huge, and enclosed with brick, stone, or iron walls; most sported signs proclaiming vigilant security systems in bold, black letters. I pulled into the lone, open driveway and rolled to a stop before a three-car garage attached to a two-storied brick house. It was obvious that the rear windows commanded a splendid view of San Francisco Bay and the bridge.
I stepped from my car as an iron gate rumbled behind me and clicked shut. So, locked in for the night. The front door, dark-brown oak sporting lustrous, brass hinges, swung noiselessly open and Sherry stood impassively framed. I quickly took in the small, well-manicured lawn bound by precisely-trimmed hedges. An alabaster bird bath held court in the geometric center of the yard, circumscribed by a well-weeded bed of cheerful petunias. Lucky birds. Statues of Venus and David guarded each side of a small portico. Where’s Cupid? In the bedroom, I’d bet.
I barely noticed that Sherry wore tailored black leather slacks and a white, sheer, scooped-neck blouse before she stepped forward and threw herself into my arms.
“Welcome, sexy man!” She nibbled my ear and ground her crotch into me, searching for my erection.
I ran my hands through her hair. “I should blush.”
“Assuredly,” she teased. “The neighbors are probably staring at us from their second story bedrooms.”
My body jerked.
“It’ll do the old fogies good. Let’s give them something really scandalous to gossip about.”
“Like what?”
“Like seeing your car here tomorrow at noon, and like this!” She bit my lip.
“Ouch!”
“Did I hurt my big, tough man?”
“Careful or I’ll put you over my knee and spank you right here.”
Sherry put her hands on her hips. “Or vice-versa. Come in.” She grabbed my hand, tapped the door shut with the tip of her red shoe, and led me into a small marble foyer.
My eyes widened. “I should have worn my tux,” I said.
“Clothes don’t make the man,” Sherry countered through a she-devil smile. She turned into the living room and said over her shoulder, “Let’s have a drink.”
“You have a stunning home. My compliments on the decorating.”
Sherry settled onto the couch, and patted the cushion next to her. I sat.
She took a deep breath. “Women have a habit of making their fortunes through marriage. I stumbled into mine through non-marriage. I had a client, a young bachelor, who died suddenly from a new disease they didn’t understand then.” She lowered her eyes and continued. “He was bisexual—as far as his family was concerned, that was worse than being gay. They disowned him.” Sherry looked back at me. “The family didn’t need his money, owned an oil company or something, but they sure didn’t want his bucks going to the likes of me. Surprise! They couldn’t contest his will.” She brushed a finely woven silk pillow.
“Quite a story,” I said.
Sherry nodded. “All that was a few years ago. But I’m still attracted to younger men, especially ones who know their way around. Thelma told me about you.” She threw a disarming smile my way. “Let’s drink to the night,” she proposed, “and to our new friendship.”
“I’d like that.”
“Do the honors.” Sherry passed a bottle of chilled Harvey’s medium dry to me. “My favorite,” she said.
I set the bottle on a precisely-folded, white linen towel, twisted the corkscrew into its target, and teased it out with a pop.
“Done like a pro,” Sherry said.
I poured. We balanced on the edges of our cushions, knees brushing, and our glasses touched in a silent toast.
Sherry raised her glass to her lips, stared through the wine’s silky red surface, but didn’t sip. The shade of her lipstick matched the color of her nail polish, and the tip of her nail seemed to vanish into the amber liquid as she slid her finger silently along the rim of the crystal goblet. She raised her head and aimed her radiant eyes at me. “Tell me about yourself.”
I sipped, swallowed, and sat back. “Very good wine. No wonder it’s your favorite.”
“I’m glad you like it.” Sherry paused and rejoined. “I’m waiting.”
I held her gaze as I leaned forward and planted my elbows on my knees. “Where to begin? There’s so much.”
Sherry didn’t hesitate. “Begin at the beginning. You’re a man who comes to the point.”
I sat up. “And you’re a woman who knows what she wants.”
“And knows how to get it.” Sherry languidly took her first sip of wine, set the glass on the end table, and kicked off her shoes. She crossed her legs underneath her and sunk into an amalgam of colorful pillows.
I sat upright and stared out the window as I collected my thoughts. I turned to Sherry and spoke in a low, deliberate voice.
“I suppose you could ask, ‘How did a shy, Catholic kid from a small, conservative, New England factory town become a bisexual sadomasochist?’ I have from time to time. But, I’m not sure I can analyze, explain . . . Hell . . . as some self-proclaimed pundits would say, rationalize the situation. Why even try? I’m no therapist. In fact, some of the weirdest people I know are therapists and psychiatrists.”
Sherry nodded and cocked her head while raising her eyebrows.
“Yep,” I responded, “I’ve had sex with more than a few of them.” We both laughed.
“I was born in a small town in Connecticut. Mom was Catholic and Dad a Congregati
onalist. So, no surprise, I was raised Catholic, and traipsed through baptism, communion, confirmation, confession. Should be called ‘captism,’ and then we’d have a more accurate description, and four C’s to boot!” We both snickered.
“Mom questioned my decrease in piety when I was a freshman in high school. I didn’t think it showed. She never found out that I drove around town rather than attend Mass when I borrowed the car on Sunday mornings. Thank God I never had an accident!” Sherry’s quick laugh gave way to a pained expression.
I leaned back and crossed my legs, one ankle over the opposing knee. “I went to college, married, and had two children. My wife and I finally divorced because ‘we weren’t bringing out the best in each other.’”
Sherry again nodded. I continued.
“I found myself in the Bay Area after a few job changes. Then I explored my sexuality. My nascent kinkiness emerged. So did my bisexuality.” My body tightened.
Sherry placed her hand on my knee. She waited until I relaxed and tapped the tip of my nose with her index finger. “Come sit over here, between my legs.”
Sherry spread her legs. I did as requested, sunk into the rug, and leaned back against the couch. She ran her fingers through my hair and massaged my scalp.
“Hmmm, that’s nice,” I moaned.
She slid her hands down my neck and kneaded my shoulders. “You’re tight here.” She flicked her finger against my back. “Take off your shirt,” she ordered.
I shucked my shirt and she gave me one hell of a massage, even from that position.
“Nice, smooth back.”
“Yeah. I shave what I can reach, get occasional help for the wisps I can’t.”
She reached around and slid her hand through the forest on my chest, followed by a quixotic, “Mmmmmm . . . ”
She resumed her two-handed kneading, which eased into caresses, and my head sunk to my chest. Her next remark jolted me from my reverie.
“Have you ever been fucked by a woman?”
“Huh?”
“I mean with a dildo, a strap-on, silly.”
“I thought only dykes did that.”
“You have a lot to learn, Mr. Stud.”
“I guess so. Is this considered Sex 101 or the advanced course?”
“It’s whatever we make it to be. But enough of labels. It’s just good, old-fashioned fun.” She looked at the bulge in my jeans. “I see you’re intrigued.”
“We both are.”
“Great! Go upstairs and use the bathroom at the end of the hall—it has a douche hose—while I freshen up.” She leaned over and rubbed my crotch. “I’ll fetch a few marital aids and wait for you in the master bedroom.”
I climbed the circular staircase humming, “When the Saints Come Marching In.” I cleaned out, but not leisurely, my established procedure accelerated by curiosity and excitement. I dried off with a huge, fluffy, white terry cloth towel, draped it around my flanks, and found my way to the master bedroom. I was about to be fucked by a woman. Would it count as losing my cherry a second time?
Sherry reclined on a red velvet fainting couch, her pale skin illuminated by a Tiffany lamp. I thought of a Renaissance painting—all that was missing were two or three cherubs. No, it couldn’t be a Renaissance painting, not with a Tiffany lamp. Perhaps a Victorian painting, yeah, that was it, Victorian. No, Tiffany came after that, in New York, wasn’t it? Well, then, a classy Upper East Side bordello—but the cherubs would have to go—perhaps a cupid or two. I halted in front of Sherry, hands fidgeting, eyes darting about the room.
She laughed. “Shy, are we?” She looked at my towel, which hung from my waist to my ankles. “Come over here, Mister.”
I edged toward her. She leaned forward and yanked the towel off in mid-step. It disappeared into a shadowy corner.
“That’s better,” she purred.
My hands flapped at my sides. Sherry sat up.
“Gonna make me work for it?” she asked, eyebrows raised. “All the way over here, Mister.”
I stepped as close as possible, my horizontal dick bobbing in front of her nose. She put her arms around my thighs, and drew me closer. Surprise! No blow job. Instead she stood and issued a command.
“Kneel and put your elbows on the couch. Don’t worry, it’s not a prostate exam . . . well, somewhat, I suppose.”
I did as ordered and peered over my shoulder. I still hadn’t conquered my awkwardness when my doctor told me to bend over his examination table, and, of course, marriage had never been like this. Sherry smiled and gave my butt a love pat.
“Relax,” she cooed. I stared at my knuckles, took a deep breath, and closed my eyes. I felt droplets of sweat forming on my brow, lining up in precise formation to jump onto Sherry’s pristine couch. I wiped my forehead.
“Don’t worry. The cleaning service will take care of it. Again, relax!”
Cleaning service? Well, it went with the place. Must be a gardening crew also. I tucked my arms under my chin and cradled my head like a lazy cat.
“At last.” Sherry spread my ass cheeks, careful not to scratch me with her long finger nails. “Nice asshole,” she cooed, “and nicely shaved, too.” Then her tongue went to work.
I was surprised at how proficient she was. Her technique was better than most guys’. I wished I could lick pussy as expertly as she rimmed. I wondered if she was bisexual and had rimmed other women. Or, how many men she had done. She moistened my hole with long strokes of her tongue. Then she nibbled the perimeter as a prelude to running her tongue around in ever deepening circles. Finally, what else can I say? she fucked my hole with her tongue. She seemed lost in her mission. My legs began to tremble and she slowly withdrew. She gave my butt a second and final love pat. I slumped into the couch.
“Yummy,” she chortled. “Great tasting butt.” She sat next to me and raised me to a sitting position with her index finger. Two flutes of white wine waited on a marble table. We drank silently, thighs and hips touching. I shivered. She fashioned yet another enigmatic smile.
“Follow me.” She rose and I trailed behind, conscious of her full attire and my nakedness. But any embarrassment had vanished. She led me to a closed door, probably over the garage, swung it open, flicked a light switch, and stood back.
“It’s the old billiards room. I didn’t have any use for it or old fogies with cigars. So I converted it into a dungeon. For old time’s sake.” She laughed. “But I kept the pool table. Great for bondage.”
I wondered about the balls and cue. Walnut paneling matched the veneer of the table and other furniture and equipment: a bondage bench covered in black leather with eyehooks protruding every six inches along the frame; a shelf displaying leather hoods ranging from slight sensory deprivation to total encasement; pegboards with coiled rope of various girths, lengths, and colors; more pegboards with collars and gags, and wrist, ankle, and thigh restraints; multi-drawer cabinets concealing God-knows-what; two gleaming, circular stainless steel chef’s potholders, from which hung floggers, cats-o-nine-tails, crops, and signal whips. A T-bar dangled in the center of the room, its suspension linked to a motorized rack and pinion. And, of course, mirrors everywhere, including the ceiling.
My eyes were drawn across the deep-pile, black carpet to empty territory against the far wall. Sherry followed my gaze.
“I loaned my cross and fuck bench to Thelma. But we’ll make due.” She ran her finger up my spine. “To the center of the room,” she ordered.
I positioned myself under the T-bar and held out my wrists. Sherry paused.
“Eager are we?” she asked.
“Eager and curious,” I replied. “Well?”
Sherri frowned. “I like my men to be willingly submissive. To squirm while I fuck you, yes; to have the option and pull away, and not, even if it hurts. Oh yes.”
I nodded. “You want me to continually give myself to you.”
“You understand.”
“I understand. I don’t agree.” I stepped toward Sherry. “I want to sur
render myself to you all at once. And then sink into your power.”
Sherry’s eyes softened. “You’ve bottomed, but never really submitted, have you?”
“You understand, Cougar. Take your Puma, now!” I knelt, lowered my head, and held out my wrists.
Sherry put one finger under my chin and gently raised my head. Her eyes sparkled from the moonlight reflected in the mirror.
“I’m glad I can give you this,” she said softly, and then whispered, “Puma.”
She released my head.
“Thank you, Mistress.”
Her eyes misted. “And thank you.”
“Now, down to business.” She shook her head, squared her shoulders, and looked every bit the senior executive. Or Domina. “Stand!”
She turned away. Soft music pervaded the room; an indeterminate, meandering melody supported by a subtle, yet driving bass. She soon returned with two fleece-lined wrist cuffs. She cinched them on my wrists and locked them to the T-bar. A whirring sound followed and my hands rose as far as possible while still allowing my feet to touch the rug. She stepped back and admired my taut torso. “This is how I like my men—helpless.”
I moaned.
“You like this, don’t you?”
I looked at my crotch. “More than you can guess.”
“I don’t guess. I know.”
Sherry leisurely unbuttoned her blouse, folded it neatly, and placed it on the billiard table. She smiled, undid her bra, and wrapped it around my neck. Then she kissed me. Deeply. She grasped my dick between her thighs.
“Feels good,” she said. “Very good.”
She dry humped me for a few seconds and backed away. Her breasts were small, tight, and well formed. Her nipples were perky, probably as hard as my dick. I stared at the tattoo over her left tit.
“I’ll tell you about that sometime. Perhaps, maybe, you’ll get a matching one.”
Before I could respond, she removed her shoes and placed them beside her blouse. Her hips gyrated and she did a slow half turn as her pants slithered to her knees. She bent over, wiggled her butt, and removed her slacks. As I had projected, her narrow hips supported lanky, perfectly formed legs. Not Playboy material, but my type—runner’s thighs and calves. She tossed her slacks toward the billiard table, but they only made it to the floor under the side pocket. She laughed and pulled off her panties. These went over my head. “Smell good, Puma?” she cooed.