“I’m losing my edge. It might be time,” Alexi says to his therapist, Liv, sitting on a park bench overlooking the river.
“The WILF Hunter retiring? You’ve flirted with retiring off and on for several years. What’s different now?” Liv asks.
“After I took on this new client, a couple of months ago, it seems everything has changed. Not only am I turning away new referrals, but I’m also handing off ongoing assignments. I’m just not feeling it.”
“What is it about the new client that has you… questioning?” Liv asks.
X pauses a moment, then responds, “I don’t know. We communicate on a different level. There is a level of respect, trust, and gratitude that extends well beyond the bounds of a typical transaction. In 25 years, I have never had a widow affect me like this.”
“Sex work is hard. Widow-sex work is even harder. You know that. Most people use us to escape grief. Is there something different here?
"I’m feeling things like I’ve never felt them before. From the very first moment our souls brushed against each other, I could feel it. It wasn’t just a meeting; it was a remembering. A re-connection of some sort."
“I think you answered your own question,” Liv says. “It sounds to me like this may be your chance to lean in with an open heart and see where it takes you. You deserve this.”
______________________________________
Marsha lets herself in the back door of Jill’s home, announcing, “Hey Jill, you decent?”
“In the kitchen,” Jill shouts as she pulls out the upper rack of the dishwasher.
Walking in the kitchen, Marsha asks, “So what do you need me for...” Pausing mid-sentence, she sees an assorted collection of freshly cleaned dildos, anal beads, and butt-plugs on the island. “Holy Moley, Jill!” she continues, "you got a whole fleet of buddies here.”
“Yep,” Jill replies wistfully. “I’d forgotten about some of these. When my guy, Mr. X, commented on a spreader bar he saw under the bed, I decided I needed to dust off and inventory it. Could you pass me the cardboard box, please?”
As they head up the stairs to Jill’s playroom, Marsh asks, "Are you as surprised as I am how committed you are?”
“This guy is different. He reads my mind and feels my heart. He gets me on a different level.”
“How?” Marsha asks.
“Well,” she giggles. “For one, he is a very skillful lover. I mean,” pointing at the box of clean toys, "he is fluent in all of these languages. But beyond the sex, he reads my mind. When he jokingly asked if I wanted to be punished, he zeroed right in for not only consent, but with choices.”
“Paddle or hand?" Marsha asked.
“Belt. He gave me choices. I answered his question by taking off his belt and handing it to him. Then he asked me how many! He is man enough to let me lead and strong enough to hold us both to a standard I set.”
As they walk into the playroom, Jill places the cardboard box of cleaned toys on the bed where bondage equipment and paraphernalia are laid out. Jill continues, “When I was about to go down on him, I said, ‘I need practice,’ and he understood. He knew I was doing this for me, not choking on his dick merely for his benefit. He doesn’t try to control me; he's here to support my need to surrender. And that is some top-tier shit.”
“Jesus!” Marsha exclaims. “What a gift! We’ve come a long way from Frat boys pouring Pop Rocks into our pussies on a slow Thursday night!”
“Haha! Or the Campho Phenique cold sore gel!”
“Well, I have enough props here that, quite frankly, I never thought I would even want to use after Bill died.”
__________________________________________
“Ding!” X’s phone signals the OK to enter. He rings the doorbell, immediately turning the doorknob and letting himself inside. Like the last session, each step leading to the second floor has a lit candle, giving off strong English Patient vibes. This evening, Jill is not waiting on the top landing.
X climbs the staircase among the flickering shadows and enters the same room that he had carried Jill in on their last date. He finds Jill sitting in the cuck chair, naked, with her blindfold and a ball gag inserted in her mouth. Around her wrist and ankles are leather cuffs. On the bed lay a spreader bar, carabiner clips, a leather flogger, a wand vibrator, and a Wartenberg pinwheel. Hmmm! X says to himself.
X kneels at the feet of the blindfolded and gagged Jill. “I’m kneeling before you. I sincerely appreciate your trust in me. I’m going to ask you some questions. If your answer is yes, nod your head. Do you understand?"
Jill nods her head.
“If your answer is no, shake your head left to right multiple times. Do you understand?”
Jill nods yes.
“OK, show me the ‘No,’ response.”
Jill shakes her head.
“Very good. If at any time during our session, when you are gagged, and you want me to stop, I want you to shake your head and say, “Uh uh, uh uh, uh uh” through the gag. This is your safe word. If you say this, I will stop immediately. Do you understand?"
Jill nods yes.
“OK. Show me how you will communicate for me to stop,” X says.
Jill shakes her head while declaring, “Uh uh, uh uh, uh uh” through the gag.
“Very nice,” X continues. “I see you’ve laid out some props and toys. Do I have your permission to use them as I see fit?
Jill nods her head yes.
“Alrighty then. Let’s get you buckled in.”
As she is guided onto the bed, her butterflies flutter, her heart pounds, and her mind is reeling. Oh my God, it’s happening! This was such a good idea when Marsha was here. What did I leave on the bed? He has free rein.
With all the self-talking in her head, Jill is oblivious that X had already connected her ankle cuffs to the spreader bar, her knees anchored 18 inches apart. The top of her toes rest at the edge of the mattress. X has now climbed onto the bed in front of her, connecting her wrist cuffs with a carabiner, then guides her elbows down on the bed.
Her back arched, her ass presenting high, Jill is consumed with vulnerability, excitement, and anticipation. She feels X slide off the bed and hears the familiar sound of his bag’s zipper, while the room air tickles the moistness of her pussy. I feel so exposed. So naughty! I’ve missed this, Jill thinks to herself. I wish I could touch myself.
X positions himself directly behind Jill’s exquisite presentation, contemplating his next move. Choosing the leather mini flogger, he places the handle on Jill’s left shoulder, allowing the 12-inch leather strips to dangle in front of her, then slowly drags them down her back, over her buttocks, until they fall to her calf. He repeats the process on the right side, shoulder to back to butt, then falls to her calf.
Oooh the flogger! Jill thinks to herself. What was I thinking? Bill was the master of teasing me to the brink… The leather strips are sensuously dragged back and forth, sliding down her back like a serpentine slithering to its special hiding hole. Oh! Here it comes…
X pauses, to himself, Oh, I know you’re ready, Miss Jill. Practice patience! He places the handle on her inner thigh, inside her left knee, slowly running up to her moistness. Stopping just short of her wet lips, he crosses over to the right side and draws it down to that knee on the mattress. X repeats the same process, this time running the handle over her buttocks, then dragging it across the sensitive taint between anus and vagina. What were you thinking, God, when you put all these delectable nerve endings here? Did her bunghole just wink?
Jill whimpers through the ball gag. Shouting inside her head, I don’t need a warm-up. I need …
Rrrrap. The gentle stinging on her buttocks disrupts Jill’s train of thought in its tracks; the soft stinging of the leather straps takes her breath away. Rrrrap, another strike to the buttocks. Jill squirms, pushing her restrained feet together; they don’t budge. She extends her cuffed wrists further toward the headboard. X’s stinging craftwork straddles the delicate border between nice and not.
Breathing hard through her ball gag, she expects another strike. Instead, X, using both palms, grazes over the light redness rising from her cheeks. The contrasting sensations raise goosebumps and stiffen Jill’s nipples, triggering soft electrical charges to radiate from her wetness. As a steady stream of air from X’s pursed lips cycling up and down her bung hole and wet lips, Jill thinks, Don’t. Stop, Don’t Stop, Don’t Stop…
X, retrieving the flogger, gazes down at Jill’s tan rose pulsing, a rivulet of cum running down her left inner thigh. Choices, choices, choices, he thinks to himself. The sudden upward flick of his wrist of the flogger squarely nips her swollen lips and clit, evoking a muffled shriek. While Jill tenses and writhes in erotic tingling, X detects no objections. A second flog, another shriek. A second rivulet of cum wanders down her right leg. With no protesting head shakes, X continues at a steady, rhythmic pace, repeating the upward action on her lips and clit, repeatedly. “I’m going to ten,” he says. “Three Mississippi… four Mississippi… five Mississippi… six Mississippi… seven Mississippi… eight Mississippi… nine Mississippi…ten.”
Jill’s head is filled with stars. Having already surrendered to X’s skillfulness, every slap compounds the stinging-pleasure assault. Jill instinctively squirms her hips forward, as if she can escape. She can’t, and she loves it. She’s on the edge of quitting, holding on to see if he keeps his word. X’s hands gently skim across her ass and legs. Jill teeters on the border of consummate pleasure and pain.
“I’m checking in,” he says. “Are you OK?”
Jill nods, her breathing still labored, spittle drooling out of her mouth.
Jill hears X’s bag open, followed by the snapping of surgical gloves, purposefully raising her anticipation. A flip of a cap and a squirting noise heighten her nervous arousal. As X applies the gel to her anus, he says, “Here’s some desensitizing gel,” as his gooey finger rims her bung hole, enhancing the tease of her radiating labia. A single finger slides into her bung, taking her breath away. Curling his inserted finger downward to meet his thumb inserted in the bottom of her soaking wet, highly aroused pussy, he holds her like she’s a six-pack. Jill moans deeply and grinds her hips as he methodically rubs his gloved fingers together through her perineal wall.
Oh my God, Jill thinks to herself, now grinding in a perfect rhythm with X’s finger massage. He gradually deepens the stroke of his now fully impaled, lubed finger with his thumb pressing from her pussy. He delights in anticipation as Jill’s body surrenders to her oncoming orgasm.
Relaxing into X’s rhythmic six-pack massage with ever-increasing intensity, the sudden buzzing of the wand vibrator both startles and titillates Jill. Breathing hard through her nose and her gagged mouth, Jill responds to the vibrator’s touch on her upper left inner thigh with a deeper arch of her back. X moves the head of the vibrator to her right inner thigh, and Jill squats to contact her quivering pussy lips. X stops the vibrator, and his fingers continue his devilish perineal massage. Jill’s legs are shaking with anticipation.
“Are you ready?” X asks.
Jill nods her head with shameless enthusiasm as the familiar sound of her wand vibrator clicks on. Her pussy lips can feel the sympathetic vibrations as X teasingly holds the vibrator millimeters from her dripping hunger.
Oh my God! I am so close, Jill thinks.
You are so close, Jill! X says to himself. X varies the intensity of his six-pack grip, diverting attention from the vibrating buddy, then places the head of the wand square on Jill’s begging pussy lips.
“OOOHHH!” Jill screams through the ball gag, twisting her body for relief from the direct contact. X is holding her perineum tight with his finger and thumb, pressing the vibrator tightly against her lips.
“Aaaggghhh!” Jill screams again, and again, as X pushes the vibrator head directly onto Jill’s swollen, sensitized clitoris. No amount of writhing can free her from his fingers’ grip and intense, torturous vibrator stimulation. “Aaaaggghhh!” she screams as waves of orgasmic bliss radiate in and through her body.
Jill finally shakes her head violently, “Uh uh! Uh uh! Uh uh!”
X immediately moves the wand from her pussy, ungrasps her perineum, and slowly withdraws his finger from her bung hole. With both hands, he lightly grazes the back of her thighs and buttocks, while paying attention to the moans and whimpers coming out of Jill’s gagged mouth. “Very nice work, Jill! I am very proud of you.”
Jill continues to breathe heavily through her ball gag, her chest heaving. With his hands on her ass, X leans in and swirls his tongue around her anus, flicking the ridges.
“OOOhhh!” Jill moans long and loudly.
X keeps his hands on Jill’s ass, waiting for her breathing to settle. He walks to the side of the bed, picking up the Wartenberg Pinwheel, the tiny pizza cutter. He puts his hand on Jill’s back, then bends over to kiss her forehead, then whispers, “Thank you. Thank you for your trust. Are you doing OK?”
Jill nods, her breathing nearly back to normal.
“I have another toy here, your pinwheel. Shall I continue?”
Jill shakes her head no, then says some garbled words, which X doesn’t understand.
“I’m sorry, I can’t understand you.”
Jill garbles again.
“Would you like me to remove the ball gag?”
Jill nods yes.
X unbuckles the strap; Jill says, “I want you to fuck me!”
“Very well,” X says. “ I’m going to unbuckle your feet, then suit up. Alright?”
Jill nods, “Yes, please.”
X removes his surgical gloves and unfastens the restraints from Jill’s ankle cuffs. He slides the spreader bar out from her feet, placing it on the floor. As he reaches into his bag for a condom, he sees Jill shuffle her knees forward and lean her face into the pillow with wrist restraints in place. She arches her back to present her hot pussy for a doggystyle pounding. X notes to himself that she definitely likes the deep pounding coming from behind.
X crawls on his knees behind Jill, grasping his sheathed cock at the base, and slapping it against her taint and pussy lips. The smacking sound confirms she is as wet and ready as he is hard and steady.
X slides his cock into Jill’s pussy, first one inch, then two, then all the way home.
“Ooohhh!” Jill moans. “Yes! Fuck me! Ooohhh!”
Holding both hips with his hands, X picks up his pace, rhythmically pounding his cock into Jill’s honeypot. His latex-covered cock glides noisily in and out of her overflowing canal of natural lubrication. Jill isn’t the only one on the cusp of an explosive orgasm.
X deepens his thrust game by shifting into the Captain Morgan pirate position, hooking his left foot in front of Jill’s left knee, with his right knee remaining anchored behind.
“Ooohhh! Jesus God!” Jill screams. “Yes, fuck me. Fuck me!” She pushes her torso back to meet X’s thrusts.
“AAAHHH!” Jill and X scream in unison as they cum together and collapse on the bed. X instinctively pulls Jill close to an inside spoon position, where she falls into a deep slumber.
X leaves a small box and a note on the table where his check is waiting. He already knows it’s going in the drawer with the other undeposited checks.
