eve

Three perfect freckles in the center of her foot, just above the strap which held her toes into the strappy sandal. Two leather straps held her foot in place. One around the ankle acting as a choker for her exquisitely narrow ankles, the other across her toes. Brazilian red polish accented her straight toes, each one was the smallest bit shorter than its neighbor, the pinky toe was a shy little school girl barely tucked in behind her bigger sister.  The four-inch heel was the ideal height to display the curve of her arch. Just high enough to imagine is fingers or member finding its way between the shoe and her foot. The soft warm flesh of his cock growing as he fondled her shoe and foot. 

With tenderness he restrained his passion, kneeling in front of her. He blushed as she planted the heel between his thighs and her sandal-clad toe rested on his crotch. His dress pants and boxers did very little to contain the now throbbing cock. It pressed against the fabric as she tic-tocked the bottom of her shoe there.  His knuckles whitened as he pressed his fists into the rug, embracing the pleasure this simple movement brought him. His head bowed he watched as she dragged her foot back, arching her foot so only the inside of her foot drew along his thigh before gliding back up his thigh. He drew a deep breath and exhaled a moan of ecstasy as the full pressure of her foot pressed and rubbed his cock in its fabric cage. He held his tongue fearing she would withdraw her attention. This was more than he could have hoped for. She had agreed he could massage and hold her feet. This gift of attention was exhilarating. 

She slides forward in her chair, extending her leg and dragging her toe up his chest. The tip of her shoe barely touching his chin. He raised his eyes to meet hers. She smiled and her eyes twinkled with mischief and seduction. “Yes, you may” was all she said.

He rose to a full kneeling position and held her foot like a priest holds a challis. He held her arch against his cheek inhaling her scent. Treasuring this intimacy. He supported her calf and felt the weight of her leg as she relaxed in his hand. She trusted him. He made eye contact, she held his gaze and he maneuvers her foot for his pleasure. She licked her lips and grinned as she bit her lower lip.  He kissed the top before rotating it and tracing the arch with his tongue. The ankle strap required deft fingers not clumsy teeth to be undone. 

Charles adored her body and her feet were the most erotic part of her. The softness of the arch, the tone of the muscles from pointed toes. The red toe polish shimmering against her alabaster skin all connecting to a flawlessly toned and defined calf. Today, wrapped in a sheer nude stocking. He cradled and caressed her foot against his body, fingering the taut toned leg made his cock thump. As her held one leg, she slide her toes back and forth across his crotch, he rocked and rose slightly to increase the pressure.

“Oh, baby.” Charles laid her foot next to the other on his lap, sliding both hands under her skirt  and bringing her ass to the edge of the chair. The top of her stocking visible he  kissed his way from her knees to her sex. Her knees hooked the arms of the chair and he slid her panties to the side, holding his mouth against her cunt he inhaled her scent. The heat from his mouth made her ache, she raised her pelvis to him aching for his touch. His tongue was electrifying. His hands cradles and massaged her ass. Her toes curled. He nuzzled and licked her wetness. He longed to slide his cock deep inside and satisfy her, for now tasting the nectar of her honey pot was enough, he thought. 

“That will be all.” She said as she pushed his head away and paced her stocking feet together on the floor. She stood, straightened her skirt and tucked her hair behind her left ear. 

“Yes, ma’am, “ He adjust the bulge in his crotch tucked his shirt in and stood at the door. “You have court at 4:00 and a dinner reservation at 8:30, will there be anything else?”

She was already back at her desk with her reading glasses perched on her nose. “Pass me the paten leather ones for court.” She didn’t look up as she spoke, just pointed to the corner of her desk.  The strappy sandals would be returned to their place in the cupboard. He collected the paten and replaced them with the sandals, lingering over them as he shut them away until the next time she needed him. 

 “That will be all, I’m done with you today.” He silently turned the lock and left, not lookback, he closed the door behind him and went back to his office. Amelia was there sorting papers. 

“Sir, I thought you were in a meeting until 3:00?” she said somewhat confused. 

“No Amelia, it turns out I wasn’t as needed as I thought. I can meet with the other partners after all, thank you.”

I have exceptional tits. The kink website had provided them a constant stream of adulation and praise. New virtual friends and discussion boards had helped me explore and accept my sexual self. My pragmatic nature has kept me safe and no I haven’t had any regretful experiences. Once, I had forgotten my own rules and things got rough, not bad, just surprising. So I meet people virtually  then in person before play is negotiated.  The message showed up on a Tuesday. 

“Your stunning, I’m the female in a couple. Can we chat?” I cringed at the wrong you’re, but this was only the second woman I had been approached by. The couple’s bio was brief but vivid. Admittedly, I will chat online with almost anyone, but she was like me, a lover of sex, masochist,  and living a vanilla life with a pension for pain. The chat room conversation was flurry of chat messages until the Saturday when she would be able to meet.  Basically, he had the fantasy, she found me attractive. I was amused. Yes, I will fuck someone just because they amuse me. 

When we met- it clicked. I was drawn to her as a person. Sexually, I wanted to devour her. She looked like a well-aged rocker chick, untamed waves draped her shoulders and framed her face. Dark eyes and full lips with a creamy complexion. If I wasn’t attracted to women before; her confidence and complementary nature were intoxicating.

I like meeting in coffee shops, they’re safe. I wished I had met her in a club. Where words are lost to pounding base and restraint is dampened by alcohol. As she spoke she explained that she hoped I was the right combination for them.  Her man wanted the threesome, she liked a bit more intensity than he was comfortable providing and I’m a bisexual masochist with a peppering of sadist. I envisioned my hand sliding up from her tits to the base of her neck, sucking and biting those plump deep red lips. Grabbing a hand full of hair until she surrendered her mouth to mine. He could watch, play, sleep, I didn’t care. I was going to make her cum like never before.  Over coffee and conversation, a definite connection was formed. She told me about the session she had just had and how her new partner was a gentle giant with fantastic skills. She assured me I would not be disappointed. Phone numbers were exchanged and the foreplay began. Within a few days of our meet, I heard from Jason. The text chat became a regular thing. About 7:30 I would get a greeting from one of their phones. We would chat about what we had tried and what was a “no thank you”.  The attraction built as the weeks went by. 

I had a free Saturday and offered my place for a night of whatever.  No matter how horny you are the first meet is awkward. When they showed up, we hugged, the awkward was settled almost immediately. My Gypsy and I sat close on the sofa, like two kittens petting and poking. He sat in a chair in the far corner of the room. He and I spoke easily and freely,  Gypsy chimed in and stroked my face or caressed my neck.  The desire to move to the bedroom was mutual.

I was so drawn to her that I tread cautiously when we went to the bedroom. I became the monkey in the middle. He was tall and strong, his kisses were deep and warm. I felt myself getting wet and caught up in the rhythm of this sexual dance. Naked bodies were revealed as pairs of hands undid buttons and lifted breasts. Gypsy and I kissed,  drawing my nails down her back and squeezing her bottom. Nothing could pass between us.  He stood close by watching  us and wanking off. When her breath began to heavy just a little I released her, he stood behind her as support as I backed away to admire her splendor. She oozed sexual hunger. I increased the intensity and pressure of my touch.  He moves towards me and kisses the back of my neck, I purr in approval as I guide gypsy to sit on the bed.  I use, my mouth and and hands to taunt and tease.  My licking and blowing erect her nipples as his broad hands opened me and searched for my clit. 

He whispered, “nice,” in my ear when he felt the wetness of my swollen cunt. Gypsy felt my full arousal as my mouth encircle her erect nipples and I began to suckle her deeply. Pressing her nipple with my tongue until she let out the whimper of pain. I stopped and asked, “Red, Yellow, Green?” We had skipped that discussion. 

“Green!” she replied and I resumed massaging and tweaking her ample breasts. As he started to make me orgasm I was keenly aware of how much I was enjoying these two.  I halted my attention to Gyspy as my orgasm grew, dropping my head and holding onto the bed I began to bend forward, my hair caressing its way down her stomach, she moved back on the bed as though to give me access to her sex, my head followed until I was bent over the bed, legs open and wanting to be pounded. They both stopped and I was taken aback as to why we were stopping.  They meet at the end of the bed. He is fully erect, his cock is purple and engorged. I don’t move I just watch. He holds her gaze and passes her a condom.  My gypsy drops to her knees and licks the precum from his cock before she takes him in completely, holds for a moment and releases him. His had is on the top of her head as she rolls the condom onto his magnificent member. It is such a simple act, but their unity is ever-present. I am the entertainment for the evening, and I’m ok with that. I am still bent forward on the bed and they both approach. This time he was monkey in the middle. 

He enters me slowly so I can feel his girth and length. My only comment is “green.” I draw up on my toes and tip my pelvis so I can take him deep. I begin to grind against him as he moves slowly, varying the depth and intensity of stuffing my wet and wanting pussy.

“Is that what you want? I ask.

He firmly hold my hips and pumps to the rhythm I have been keeping. My orgasm picks up where we left off and the sensations fill my body. I fight the urge to buck. I hold the orgasm until his pounding is frenzied. We ride the climax together, I gush and feel the liquid run down my legs as he finished with a half dozen intense drives. My legs are shaking and I have been well services. He finishes with a playful smack on the ass. 

“He’s learning to like it?” I asked. Gyspy swats him as well when she joins me on the bed. We kiss and dissolve into laughter. I am satisfied that I have met my obligation to him, now I want her. The conversation and caressing continued. She is my focus, I want to make her cum. She is shaved clean and I trace the triangle between her legs licking my fingers to slide them between her legs.  I won’t ask for It I will caress and play until she opens herself to me. He is stretched out on the bed, playing with my right tit as I explore Gyspy’s face, neck, and breast. I can’t get enough of her breasts. I hold her nipple between my teeth and flick my tongue until her body responds to me. As I move closer she drops her leg to the floor and slides her cunt towards me. I cup her pussy and use my middle finger to test her wetness. Freud was right, I do want a penis. I want to fill her cunt and make her scream in pleasure. I don’t want to be restrained. I check my thought and kiss my way down her body, her freshly shaved pussy is mine for the taking. I look up and her eyes are closed. He is close and whispering sweet nothings to her as he restrains her. The restraint by him plays to her kinky side and I’m delighted. I can make her cum quickly, but what it is the fun in that. I lick and suck her clit. Sucking her entire clit while two fingers gingerly explore her cunt, I suck in rhythm to fingering her two fingers flat against the front of her vagina get me the desired response, she moans in pleasure. He is nothing more than a restraint at this point. She is mine to tempt and tease. I edge her well after she is wet, her labia is swollen and she jumps when I blow on her clit. The gentlest lick is met with a whimper I have slowed the pace so she is on the edge. As her body starts to relax I build the intensity again. I didn’t ask her for permission. As I finger her she begins to buck. I suck the inside of her thigh and leave a childish hickey. I want her to have a reminder of my visit to her honey pot. I finger fuck her as she gyrates. I suck her clit as she squirts sweet nectar into my mouth. I am satisfied and I continue until her hips bear down into the bed and she stops. Gypsy has ridden her orgasm to the end. I lean over her kiss her with my cum stain mouth and say we’re not done. I rest my face on her thigh and continue to stroke her body.

This time I use her clit to arouse her, being more subtle in awaking her sexual hunger. I nip, bite and suck drawing my nails over her body, holding handfuls of hair and we kiss intensely. Her nipples are erect and alive, my swollen lips purse and blow cool air over them until they are taut. I graze my teeth on them the pain for pleasure made her moan. 

“I want to make you cum again, red, yellow, green?”

Green is all she moans. I go down so I can raise her up.

This was the best part — the first session. Mark was a 30 something once upon a time hockey guy with a love for satin and lace. I wore a green velvet wrap dress and patent leather heels. He had picked the dress out one our first outing. It hugged my tits and offered way too much cleavage when I was seated. I rather enjoyed the once over and grins from the concierge and bellboy as I checked in. The shoes were from my collection. You know the ones, with the ankle clasps and little heart-shaped locks — a subtle nod to the kinkster in all of us.

The clicking of the stilettos drew the notice of a couple waiting near the front doors. The three white-haired suits, previously deep in conversation, looked up in unison. One was ballsy enough to tip his glass to me. I smiled broadly and winked, never breaking stride – the elevator opened with perfect timing. I vanished through the looking glass as the mirrored doors closed. A swipe of the room key accesses the concierge floor, a pleasant surprise from Mark. 

A bowl of white flowers was luminescent in the late afternoon sun. I repositioned them and laid my case on the table. I pulled my worn jeans and white tank top from my oversized bag and hung them on the bathroom hook. A girl needs to be comfortable when she is educating a sissy boy.

I went about setting things up. A plain t-shirt, a collar with a pink ribbon as a leash on the bed, and a silicone cock ring. A subtle but effective start in setting the mood. That would be after he set up my case and showed appropriate gratitude for my presence. An enema bulb and baby wipes in the bathroom. A long blond wig, a pretty dress with ruffles and bows, and a pair of white ruffled panties were hanging in the closet. He would earn those.

The view from this height was outstanding, yet as I skated my fingertips across the glass, I envisioned his hard cock arching as I pegged him spread eagle against it. The thrill of his naked body pressed against the unyielding coldness, the humiliation of his nakedness on display for the end of day commuters, gave me such a rush. I retrieved my crop from the case, leaving it open for him to unpack as instructed.

My phone buzzed. He was texting from the parking garage. 

I texted, “the door will be open. I am going for ice. Come in, undress, your collar is on the bed, put it on. Kneel, facing the window, and wait for me.” 

I grabbed the ice bucket and room key and trotted down the hall. I took my time returning to the room about ten minutes later. Mark was on his knees, his clothes neatly folded on the dresser. He was holding the ribbon leash in his hand. 

“Give” I commanded. His hand came above his head until I possessed the ribbon. “What a good sissy, you listened so well.” I stroked his hair and moved in front of him, making sure my skirt brushed his naked arm. The velvet was dragging against his skin, awaking his sense of touch.

“Rise” He did as instructed and forgot himself meeting my eye for a moment. My raised eyebrows were enough for him to flush and blurt out, “Sorry, Mistress,” and he lowered his eyes. 

“That’s three hairbrush smacks, keep count for later.” I traced down his side and under his balls, ensuring my cleavage was in his eye-line. I stroked his semi-erect cock watching it grow with every stroke of the soft leather. 

“How sad you are, men are the weaker sex. Your cock is delicate and unprotected, and your sex organs are like accessories. Do you wish you could hide your weakness?”

“Yes, mistress,” he blushed and went to cover his hard cock. 

I stepped closer to caress his head, “good sissy,” pressing my velvet wrapped tits against his bare waxed chest. “Are you ready to begin?

“Yes, Mistress,” Mark blushed and smiled.

“What are your safety words, Sissy?”

“Hamilton for stop, no more. Evita for a check-in.”

“Good sissy. I had given you a few tasks, time for an inspection. Pull out the chair and stand on it.” I sat on the couch, watched, and waited. I took a nail file from my bag, inspected my nails, and ignored him. I drank my water and sucked on a piece of ice, taunting him, allowing my skirt to stay hiked up as I maneuver to dig aimlessly in my bag. I began his inspection. He adjusted his stance. 

“Is my little slut getting tired?” I lifted his balls to ensure they were hair-free, I cupped and caresses, his cock began to twitch.

“Almost,” I pulled a stray hair, and he fought the yelp. “Three for the hair, five for whimpering. Women wax without a word. How many is that?” 

I stepped back and held my hand to help him down. He hopped down without a word.

“Oh, no! No manners, that’s five with my hand. You are going to have a very pink ass. On your knees, get the brush from my bag, carry it in your mouth to the couch. Place the pink vibrator and lube on the window ledge, let’s put the ball gag over there too. The crop, flogger, and paddle on the end of the bed.” I held his lead. Encouraging him to move quickly, ensuring he was thrown off, mocking the mistakes. Every so often tapping his ass with or balls with the crop. He was completely erect. 

“You fucking little pansy. You should be ashamed of yourself, a sad little man, not worthy to touch my belongings. Just touching them excites you. Tuck your shame between your legs. I don’t want to see it.”

He dropped his head and kissed my shoe. He held the position waiting for further instruction. I didn’t move my foot. “Don’t stop.” He kissed and licked my shoe. Nuzzling his head gingerly against my calf. “Good sissy, now over to the couch to take your punishment.” I went to the closest and brought out the panties. “I think you should wear these while you take your punishment before you clean out your ass, and I take you against the window.”

His face turned crimson, and his breath drew hard. He was surprised. Every detail of our conversations was creating this session. As promised, the pain was subtle. What he had not expected was how his humiliation promoted his submission and complacency. The bikini briefs were satin and soft, increasing his sense of arousal. His cock pushing over the top. He struggled to tuck it, but it was so hard all he could do was push is to the side. He fumbled to hide his excitement. I would not acknowledge his effort. I wanted him to own his shame. He knelt next to me, waiting for instructions. I pointed to the table.

“Pass me the brush.”

He extended his reach as he placed himself across my velvet lap. As I slide my hand under the edge of his panties to pull them down, his cock pressed into my thigh, weeping onto the fabric. I could feel his humiliation as I brought his panties down and exposed his bare bottom. Rubbing his lily-white ass, letting my nails brush his balls until he whimpered. 

“How many?”

“Eleven with the brush and five with your hand, Mistress.”

“And how many for soiling my dress?”

“But I,” without thinking, he kneeled up. He instantly realized he had not been given permission to move. His mouth was on my shoe again. 

“You’re learning, but soiling my dress, your dirty little piss ant. Velvet, do you know how to clean velvet?” Before he could speak, I cut him off. “If you can’t answer, I will discipline your stupidity. Five more! Now, you are wasting my time. Tuck the cock and get across my knee. Count for me.”

I rubbed his ass, letting my fingers hesitate on his asshole, pressing and rotating my finger until an involuntary moan. “That’s it slut show me your weakness.” With my hand, I slapped his ass in quick succession, each smack harder than the one before. He whimpered a little. I cooed his name and rubbed the pinked ass cheek. Without prompting, he checked his cock, was tucked, and reached for the hairbrush and put it in my open hand. 

“Why am I spanking you?

“Because I’m a slutty sissy who keeps messing up…Mistress.”

He counted each smack. His ass was red, and he was silent. 

I checked in, “need to talk to about Musicals?”

“No Mistress,” he fumbled the panties back up, he was flustered and attempted to cover up. His humiliation was palpable, he knelt at my side, fingering the fabric of my dress.

“You did well, my little sissy, now we can start. Into the bathroom and bend over.” 

“How do you want me?” he asked. I removed the collar and place it on the counter.

“Turn on the water and pass me the showerhead.” I retrieved a pair of rubber gloves and opened a bar of soap. “Remove your panties, I’m going to wash your ass.”

Mark got in the tub. “Lean forward and spread your cheeks.” He looked back towards me but did not speak. I soaped his ass and used the showerhead. The humiliation and stimulation engorged his cock. “That will do, dry off, and wait here for me.” He stood in the tub, drying off. I retrieved the lube from the windowsill. The sun was setting. A dusk pegging would have to be next time. Nighttime would have to do. I flicked on a light and returned to the bathroom. 

“Are you ready?” he nodded and went to kneel again. I stopped him. I filled the bulb with warm water and a drop of shower gel. I lubed the top of the oversized bulb. “Spread your checks.” He did as he was told. As I inserted the bulb, he drew breath. “I washed you and now I am cleaning out your pathetic ass, and you don’t thank me. Ingratitude is an insult. Ten more smacks with the brush.” My voice was the sternest it had been all session. I left the bulb in his ass. “Hold that there.” I removed my panties, balled them up and stuck them in his mouth.

I emptied the contents of the bulb into his ass and waited. He was fully erect with a mouth full of worn panties. As he stood in front of me, I began to stroke his cock until he was utterly engorged, and he was unable to stay still. I caressed his ass; he was holding it tight. At least 30 minutes had passed since I had filled him with warm soapy water. “You can sit on the toilet, but I will be very disappointed if you use the toilet without permission.” He sat, and his ass began to leak. His eyes widened in acknowledgment that he had failed. I kept going with my plan. I pulled perfectly pink nail polish from my bag on the counter. 

“My sissy must look her best before we continue. Give me your hand.”

His ass continued to leak, and he continued to blush. As I finished painting his pinky, I told him to release it. Mark was mortified, but out of options, his bowels evacuated as I continued to paint his nails. He had no control over his body. His cock had been torturously edged, his gut gurgled and squirted. He had a mouth full of dirty underwear, all the while I painted his nails, made ugly faces every time he passed gas. I explained how lucky he was that I was willing to raise him up from being a dirty pig to a pretty little sissy who I was going to peg for the whole world to see. When I finished his nails, I removed the underwear from his mouth and left him sitting there, unable to do anything except wait for his nails to dry. I put a piece of gum in his mouth, turned off the bathroom light, and closed the door. 

I put on my harness and dildo, under my jeans and pulled the tank top over my braless tits. I grabbed the dress and wig and brought them to the bathroom. Time to turn things up a notch.

The adrenaline made her heart pound in her ears. Aroused and scared, she fought the urge to call red, she closed her eyes and worked to control her breath. It was so quiet, she chewed on her bottom lip, listening. It was weird. She found herself listening for the clock in the kitchen. It was not physically possible to hear it. Her husband’s heat against her back warranted her attention. She opened her eyes. A purple satin blindfold was in front of her. Cal’s mouth was warm on the back of her neck. He didn’t speak as  he traced along her shoulders, making her cunt ache. The arousal worked its way through her body. Her nipples pulled taught and hurt. The smallest murmur of pleasure escaped her parted lips as she licked them and pulled her bottom lip into her mouth, biting down as the blindfold was tightened around her head.

Karen was thrilled with the attention. Her body was alive and electrified with waves of pleasure. Cal’s hands were everywhere, and she had never been more aware of how responsive her body was to his touch. He was on his knees behind her, drawing his prickly, unshaven face across her ass. His right hand slid between her legs. His fingers opened her lips as his middle fingers entered, his thumb on her clit and pinky on her asshole. As he pumped his hand, Karen’s body responded hungrily. She gyrated and called for more.

Cal encouraged her as she became more vocal. She was so wet. He removed his fingered and swatted her ass. He licked her off his fingers as he maneuvered to stand in front of her. He was going to need to rethink this setup.  He massaged, squeezed and pinched her breasts while she sucked his fingers, her mouth open like a baby bird hungry for the worm. “Don’t you dare cum without permission, or I’ll stop?” he said as he squeezed her nipples. She whimpered in protest, “please?” He stopped moving and removed his hands.

He could feel her eyes get big and stare through the blindfold.  She drew breath to speak but suddenly chose not to. Her shoulders dropped the restraints held her body weight, and she mumbled, “yes sir. ” So quietly it was clear she had learned it was useless to argue.

“Good slut, such a good girl.” He left her alone for several minutes. He was examining the selection of toys, canes, a hairbrush, and a couple of floggers. Karen stood in her restraints, moving her neck and shoulders. She had to be aching. Cal returned and kissed her roughly until her body responded. “What do you want?” he asked.

“You,” she stated. He smacked her thigh with the hairbrush.

She winced in surprise but said nothing. Cal wet his fingers in her mouth and began to flick her clit. Bringing her to the edge and backing off. He teased her by occasionally sliding his fingers deep inside, leaving them only long enough to feel the muscles contract. Impact play mixed with the edging was making Karen’s head spin. Sweat glistened and dropped from her. Cal’s traced a rivulet of sweat from her sex to her breast as he brought her close. She relaxed into his body; she was exhausted and sexually electrified. Every touch drew a deep breath and anticipation. 

“Ok, baby, you did so well. I’m going to let you cum now.” She had expected to be let out of the restraints. Her body instantly cooled as Cal backed away. He was on his knees, released her legs. Before she could draw her legs together, his hands were cupping her ass, and he had positioned her legs over his shoulders. She struggles to pull herself up, acutely aware of her size and weight. She was in her head again, just like that.

He gently maneuvered himself away and let her stand on her own feet. He removed the blindfold and released her arms.  He had pushed her far enough tonight. He wrapped a large soft blanket around her as he leads her to the bed. He cradled her in the pillows. He removed the hair elastic, freeing her hair and laying it across the pillow.  She was too tired to protest. He walked to the other side of the bed, “My darling, you were magnificent this evening. You are so beautiful”. Karen’s head was empty. She was raw and unable to respond verbally. Her arms were heavy; she flicked the blanket away, inviting him to join her. 

He was playing with his cock as he stood, admiring her.  He was mostly done giving orders. When Cal crawled onto the bed, something softened in his body language. He stroked her face and kissed her forehead. “Are we still green?” he asked.

“It’s all good, but my body is” She struggled to lift her arm, “kinda’ tired. I enjoyed this evening, but I can’t explain how I feel. My head is so empty.” 

“Will you let me make love to you, cum when you want, be as loud or silent as you want. Let me love you.” He didn’t wait for her response. He kissed her hard and maneuvered himself to between her legs. He planked himself above he cradling her head in his hands. His cock pressed on the outside of her sex. He came to his knees and continued to kiss her neck and face until she relaxed and opened herself to him as he entered her body wrapped around him. Karen’s head fell back as a moan of ecstasy left her. Cal moved slowly bring her to the edge quickly. He kept the pace, feeling her pussy contract. “Relax, your pussy for me.” She obeyed immediately, as soon as he felt her relax, he increased the speed and intensity. Karen’s body reacted; she felt like she was outside herself yet wholly presented. The first wave of her orgasm came as her hips raised and bucked. She dragged her nails across her back as her body responded to Cal’s attention. Words of praise and adoration stumbled from her mouth, trying to articulate the pleasure. “Shhhh, I know. Just enjoy the ride, baby.” She grabbed the sheets, locked her ankles around his ass, and rode the orgasm to the very end. As she finished, he slowed the pace feeling her relax. 

“Finish me.” She felt his cock twitch inside her as his words hung in the air between them for a moment.

She smiled coyly, “yes sir, of course, sir.  On your back, sir.” He rolled off and onto his back. Karen’s aches and pains were gone; she had forgotten all about them. She licked him from his balls to the tip, taking special care with the head. She sucked just the tip increasing the pressure until his hand was on her head. He took him to the back of her throat and sucked softly as she moved up and down his shaft. His balls were in her hand being pulled every so tenderly the way he like it. She mixed the speed and pressure as his cock grew hot. She took him in hand and stroked him as she maneuvered herself forward, letting her breast sit either side of his engorged cock. “If it pleases you, Sir, I would like to drink,” she said as she squeezed her tits around him and put the tip in her mouth again. Within moments he exploded into her mouth, hot cum hitting the back of her throat. She continues to milk every drop until he pulled her head away.  She didn’t move from between his legs. Instead, she placed her head on his stomach and said nothing. She twined her fingers through his chest hair lazily as he stroked her hair. Drifting on calm seas, they were both soon asleep. 

Sissifying a hard body was more than fun. It made me happy. I loved turning my fit fantasy men into sissies on the down-low. On the hotel room desk, I placed a selection of new cosmetics. Cherry pink lipstick, matte eyeshadows, a simple mascara, and blush. The essentials for the transformation.

He stood between the toilet and the tub in the dress and stockings. Baby had put himself in a corner. Mark looked at his chiseled features under the curly blond wig and smiled. It wasn’t a smile of joy. It’s what relief looks like. “Thank you, Mistress,” shot out of his mouth when he saw me in the door. He was quick to comply and anxious to please. While I enjoyed the compliance, a little resistance would be nice. The multi layered skirt was short, just to the edge of his ass. He had picked it out and had it delivered to my house. The only condition on the play was I keep his things with me. 

“Bend over and show me your ass.” I fought the urge to use the common courtesy of please and thank you. Mark hesitated. He placed his hands on the back of the toile and straddled the basin. I dipped the anal plug in the tub of lubricant. I amplified his sense of vulnerability with silence, I tickled and careless his ass and asshole under the satin panties, the satin of the skirt rustled as I used my nails on the fine hairs at the edges and pressed my thumb to his asshole. Only when a moan and body shutter indicated the intensity of his arousal did I proceed. I order him to masturbate as I lift his skirt, his arousal makes insertion easier. I knew the large plug would stretch his asshole and make him all to aware of it with a playful smack on the ass and a “good boy.” He stands upright and faces me. His 6′ 1″ frame contained in satin ribbons and bows pleased me. He is very beautiful, yet venerable. My nipples ached they were so erect. 

“Come with me.” In the bedroom, I had pushed the table aside. There was ample space on the floor. “If you are going to be my dolly, you have to know how to play the sissy games girls play. I grab a small container, sit on the floor, and motion for Mark to join me. Matter-of-factly I say, “We will start with something simple.” Mark fusses with adjusting himself to sit cross-legged in front of me. I smirk with amusement as he struggles to be graceful. Good girls learn early on to be seen and not heard. I pass him a ball and six jacks. I show him how to bounce a ball and pick up the jacks. 

He fumbles the ball and scrambles after it too many times to count. He is visibly flustered. I simply tell him to start again. Once he can bounce the ball and pick up a jack, I reward him with a “good girl” and a sweet kiss on the forehead. He blushes and waits. 

I continue to push his expectations to the side and offer another juvenile pass time. “Good sissies know how to play nicely and  know how to play girlie games.” I teach him a clapping game, Miss Mary Mac. He is agitated. I smack his fingers when he makes a mistake and remind him that 6-year-old girls can do this. His face is flushed and the wig is sticking to him.  He stumbles, but masters the rhythm and the words, I’m satisfied. 

“Are you having fun? If you are going to be a true sissy, we need to get you ready, that rough face is just not going to do at all. Crawl to the chair and wait. Don’t touch anything.”

I sit in the chair between the desk and the window with a cold glass of water. “Go ahead, make yourself pretty for me.”

I watch as he examines the items laid before him. He touches each item gingerly, not quite sure where to start.

“Start with the eye shadow. “

“Yes, Mistress.” It’s odd. I suddenly realize I don’t need to be called Mistress, his desire to please and actions demonstrate his obedience. 

He is tentative in opening and applying the color. I lean against the desk and move a curl to the side. His fingers are too large for the small sponge tip applicator. He reaches to adjust the desk lamp and pause, “May I, Mistress?” I nod in approval and approach him. I slide the cosmetic to the side and sit on the desk facing him. The dildo makes a somewhat awkward bulge in my jeans. Adjusting my crotch, I settle in front of him. Placing a finger under Mark’s chin, I apply an excessive amount of eyeshadow, mascara, and blush to my little slut. I pluck a few stray eyebrows, just to enhance the experience. “The price of beauty sweet-heart,” I quip. The final touch is a deep red lipstick. I lean to the side so he can see his reflection. He is my doll, my dress-up barbie. The makeup is over the top, but there a change in his features. With the blond waves and the makeup s/he is my little slut.

“Undo my pants,” I order. S/he does as she’s told. “You know what to do,” I motion to the dildo in my strap on. I lean back on the desk, freeing up my pelvis to move. I raise my ass so s/he can pull my jeans down and free to cock. S/he is hesitant. 

“Be a good slut and put that cherry mouth to good use.” My tone is flat and indifferent. S/he bends forward and takes the tip into her mouth. I place my hand on the top of her head, not pushing, but encouraging a rhythm. Words of praise and pleasure for Mark’s efforts are rewarded. S/he is on task taking the silicon cock deeper into his throat, gagging and drooling saliva. I’m wet from his attention but show no sign of pleasure. He licks and sucks the cock while I rock my hips, I slowly edge forward, pushing his chair back until I can stand. Marks mascara is running a little from watery eyes. His lipstick is smeared. 

“Look at yourself, a slutty mess, and we’re just getting started,” I say as I use his skirt to draw him close. “Present yourself for inspection.” Mark interlaces his fingers behind his neck and stands with his legs apart.

Moving the panties to the side reminds my sissy that she is still a man. “You really can’t control yourself, can you?” I stroke his cock slowly as I speak. I intensify the stroking until he can no longer be silent. I am close, my words are stern, but softly spoken. I remind him of his flaws, and I how disappointed I am with him. “Where is all the enthusiasm I saw when we met and talked about you wanting to serve me?” I query. My stroking has him driven to distraction. He doesn’t answer. I stop mid-stroke. 

“I’m bored; you bore me.” I walk to the window abandoning him and the intimate moment. He is exposed.

“I’m sorry, Mistress,” he mumbles. And he goes to cover himself. 

I watch his reflection, waiting until he squirms, one shoulder drops, he thinks it’s done. I turn, “are you ok? Are we still green?”

“Yes, Mistress.” He is short on words, but his body language is relaxed and comfortable.

I retrieve a small leather-covered paddle and a silicone cock ring without prompting Mark turns and lifts his skirt. Never wanting to miss an opportunity, I smack his ass with my bare hand until the skin is pinked up. 

“Thank you, Mistress.”

“Good, Sissy, that was enjoyable, but I wanted your cock.” I spit in my hand and wet him so I can slide the ring on. “Are we green?” He nods but doesn’t speak. “I think it’s time you demonstrate your maid skills. I would like a cup of tea, one milk, one sugar. And while I am enjoying my tea, you will be my footstool.”

I picked up my phone and gave it a passing glance while watching my sissy-maid attempt to be elegant. S/he presented me with my tea and positioned himself on all fours. As my footstool, he would learn patience. I place my feet on his back and sip the tea. I trace along his back, down over his ass, and along his stomach with my foot. “Well, you have a little think about. What you could have done wrong while I finish this lovely tea, even if it is too hot.” Ensuring he is still erect. I read blurbs on my phone and turned on my music. I rise and leave my footstool. 

“Do you know how many mistakes you just made?” 

“No, Mistress.”

I return to the window. The glass is icy. The cold on my back is refreshing.

“Ok, Slut! Let’s put that manly strength to use. The table needs to be moved. I want space in front of the window.” 

“Yes, Mistress” he says indifferently. 

Sternly I spit at him, “do show some enthusiasm, you waste of air. Get my strap, hands on the dresser, and drop those panties.” 

His humiliation and embarrassment were evident with the hesitation of bringing his panties to his knees and lifting his skirt. I checked that the color of his cock was still right. I slide my icy fingers along his balls and around his engorged member. He moans in pleasure at the attention. Jizz seeps as I pump. I use the lubrication to remove the cock ring. I have been edging him for hours. I check that the cup I took from the bathroom earlier is on the table. 

His body is quivering from the intense attention. I stop. Move around, to look into his face. “Now your punishment for not using please and thank you, making my tea too hot and not cleaning the bathroom up after you used it. There will be 15 straps on your ass, 15 on your thighs, I want a nice red behind to play with. Count for me. If you cum while I am punishing, you. I will stop and you will have to put on your street clothes and go home. Tell me, you understand.”

“I understand.” I smack him across the face. “You worm, who are speaking to?”

“I’m sorry Mistress, I forgot myself. I am unworthy.” He drops to the floor, placing his face on the ground, arms forward, and ass in the air. He moves so quickly his skirt leaves his ass exposed, he wiggles his ass, trying to get it to fall into place. His panties had dropped to his ankles when he prostrated himself. I step on his fingers, watching his face carefully. I press until his face winces. 

Without prompting, Mark’s words are measured and careful, “thank you, Mistress, thank you for teaching me. I am not worthy.” 

I go to the bathroom and get his underwear. He is still on the floor with his ass in the air, I grab his hair and bring him to the kneeling position. 

The underwear is balled up in my hand. I intentionally don’t speak. I hold them in his face until he opens his mouth. I wait until his mouth is wide, and I stuff them it. 

“Stop wasting my time, Assume the position. You panty waste.” I retrieve my strap from the table. Without warning, I deliver the first strike across his thighs. He counts one loud and clear. I flick his skirt up, caressing his ass and plug. I tap his legs to open wider, so his balls hang free, and I can see the ass plug. I deliver the strap at changing speed and intensity of each impact. At the halfway point, I take his penis in hand and stroke his engorged cock. The marks cover his thighs and ass thoroughly. 

“Do you want to cum?”

“Yes, Mistress, please, Mistress.”

I step away. “Let’s try that response again.”

He is confused. 

“When do you get to cum?” I ask from behind him.

A light bulb goes off. “When you say so,” he says brightly.

“Good. Take off the dress and stand in front of the window.” He did as I asked, carefully hanging the dress back in the closet. I opt not to rush him at this point. As I begin to lube my strap-on, I speak, “now you see that cup on the table, I am going to fuck you in the ass, and when you cum, you cum into that cup.”

I give him the lube to stroke my dildo, I tweak and pinch his nipples. His eyes closed, and his breathing becomes ragged. At the window, I arrange him as though he was on a St. Andrew’s cross, remove the ass plug and toss it onto a towel I had placed on the floor earlier in the day. I remind him, that he is on display for the whole city as I grease his asshole and load the tip of the cock with lube before I slowly fuck his ass. I have him hold his ass cheeks apart and guide the cock slowly, feeling his ass release and take it all. I keep it buried, pressing my body towards his back. His chest presses into the window have the desired effect of shaking his senses. The thrill of being on display tangled with the icy window against his chest amuses me. I increase the rhythm as he settles back on my cock. The control is invigorating, his inhibition is intoxicating. Words and sound of surrender tumble from his mouth His pleasure is palpable. I barely need to move; he’s writhing and doing all the work. It’s like a standing reverse cowboy. When I am satisfied, and he hasn’t lost his erection, I pull out and leave him there. I pass him the cup. 

“You can cum in the cup.” Without hesitation, he masturbates and comes almost immediately. He squeezes every drop into the cup. 

“Drink it” is all I say without inflection. He throws it back like a tequila shot. Mark is spent, his makeup has run, and his wig is disheveled, he is naked, and his cock is becoming flaccid.

I sit in the chair; my shirt is damp and clings to my erect nipples. I rub and caress them as I watch him try and figure out if he should stay or come to me. He kneels in front of me and says nothing. 

“What does my little slut want? I ask.

He motions to my chest. He leans against my chest, and I pull off the wig. He settles in as my nails gently scratch his head. We make small talk. He strokes the curve of my breast. I close my eyes. My mind is quiet. The session is done.

He thumbed through the handwritten pages. Colorful descriptions and dry accounts of their play intermingled with some reflections of her day to day. He knew this stuff. There was very little here that wasn’t said or texted. He tossed the journal on the bed and paced the room. He knew Karen had enjoyed the increased intensity, but he was sure she was still holding back. The release he wanted to give her would mean shattering barriers.

He took her leather corset and patent leather heels from the coffee table chest in their bedroom. He went about converting the bedroom into their dungeon. The curtain rod was a metal pipe spray painted to blend into the room. A simple blackout curtain behind the drapes ensures complete privacy. There were extra rings that anchored on the ends to hook chains into. Two large eye bolts were into the wall near the floor for securing ankles. He knew every inch of her body. Tonight, would be the agony, and the ecstasy, her spread eagle on display for him, was pure delight. It was time to push her boundaries this evening. 

Cal was in the shower when Karen arrived. Her journal was open and next to her corset, g string, and heels. She felt amazing in her corset, the way it hugged her, raised her breasts, and made her look sexy. The shoes were too high for outside the bedroom; they made her ass look amazing and made her the perfect height for Cal to cup and caress her ass as he drew her close. She stripped to her bra and panties and sat to her makeup table. Karen brushed her hair into a high ponytail. While pulling her hair tight, she was automatically leaning into the mirror for a closer look at her skin, looking for fine lines. She smoothed the stray hair back with a small amount of hair product. Blue-black mascara and navy eyeliner accentuated her eyes, a creamy deep red for her lips and a dusting of powder to set. Panties and bra tossed into the laundry hamper she now stood with one foot on her chair, she stroked her sex and watched her nipples pop. She wet her middle finger and rubbed her clit. She dropped her head and curled into herself, all the while keeping her foot on the chair. Karen’s breath quickly became ragged.

SMACK

“What the fuck?” Karen dropped her hand and straightened up to the sting on her ass. Her eyes were filled with fire as she stared at Cal in the mirror, too shocked to turn and face him. Her foot still on the chair frozen. Then the rush of embarrassment. She was at a loss for words, torn between being caught and fury of having her pleasure halted. She turned to face him and speak.

“You didn’t ask if you could. You got one, I’ll give you a choice for the other 9, over the chair or my knee?”

He stepped close and caressed her cheek, “The rules were clear, no kids, in the bedroom, no questions.” She resisted the urge to storm off. She liked this game. Their relationship was better than ever. Cal was attentive and confident; her love for him had grown deeper. 

“Over your knee, Sir.” She reached for her corset. 

“You won’t be needing your things tonight. Over my knee and count for me.” He rubbed her ass as she adjusted herself. The intensity of the impact increased with every slap. Karen was silent until the last one when a small yelp escaped her lips.

“That’s my girl.” As she went to get up, he maneuvered her, so she was now sitting on his lap. Her ass tingled, and the hair on Cal’s legs itched against her ass. Cal placed his warm hand on her pussy, and she opens her legs for him. He dipped into her wetness and fed it to her, smiling as he did. She blushed. 

“Are you ready, my beauty?

“I guess?” Cradled in his arms was lovely, she could stay there all night.

Cal motioned for her to get up, he escorted her to the window. As he spoke, he stood directly in front of her, holding her face in his hand. “You are so beautiful, and I want you to own that. I had these made for you.” On the couch were teal wrist and ankle cuffs.

Karen was at a loss for words and felt a little foolish. She knew about the renos Cal had done in the bedroom, and he had talked about increasing the play, but she hadn’t put it all together. 

“Do you want to proceed?”

“Yes, Sir.” She smiled broadly. How bad could it be really? Leather bracelets are all they were really.

“Do you trust me?” He purred, his charm and confidence were electrifying.

“Yes”

“I am going to put your cuffs on. I am going to admire and inspect you. Then I am going to tease and arouse you. I will use your body as it was intended to be used. Safewords?”

She presented her wrist to him, “Red, Yellow, Green,” she said. She looked at the cuffs and the detail. The chrome grommets had little crystals on them. The velvet lining felt nice. Cal tapped her thigh, and she raised foot onto his leg. Fully exposed, she instinctively covered her naked sex. He eyeballed her hand until her arms were at her sides. Karen wondered why he wanted her on display laid bare. It hurt to be on display. Her throat was tight. Her cunt ached. She could not articulate how vulnerable the idea of restrained, and on show now made her feel.

“If you want me to stop at any point, just say the word.” He was continuously caressing as he spoke. “I want to help you get out of your head into your body. Trust me-sweetheart.” He kissed her full on the mouth and held her close until she relaxed into his arms. 

Karen’s body resisted as Cal clipped her restraints. As he guided her wrist, he supported her from behind, whispering admiration and praise in her ear.

SNAP

Her arm restrained panic hit, she hauled up short when she went to bring her arm. Karen’s heart pounded, and she began to breathe hard, “I have to go, she repeated. She was scared. Cal wrapped himself around her, not releasing her. Instead, he held her firmly to his body. 

“Focus on your breathing, you are safe, you are loved, inhale for me baby, breathe. I am so proud of my girl. You are doing so well. Breathe, inhale, exhale.” Tears rolled down Karen’s face. She couldn’t process her reaction or emotions. She struggled against the urge to call red, choosing to listen to Cal’s voice and feel him caress her back and ass. 

“Stay in your body; concentrate on my touch.” Her thoughts bounced from the fight or flight response in her head to the sensual caress and heat Cal provided. He continued to speak softly. Her breath ragged with shutters. Eventually, her restrained arm relaxed at the shoulder. He took that as his cue to continue.

He devoured her mouth and neck as he slid his finger across her sex, still a little dry. He retreated and made his way to her breasts. He held her free wrist and used her hand to touch her left nipple while he licked and nipped the right. Her breathing had slowed, and purrs rose from her throat. Karen’s free arm went towards the back of Cal’s neck. He knew that was her wanting him close. A gentle “ah” escaped her swollen lips.

“Good girl, that’s it.” He placed his finger on her clit. It was rock hard. He flicked it with lightning speed. Karen rose to the balls of her feet and tilted her hips forward to give her master better access. “Is that what you want? You want me to make you cum?

“Yes,” she quivered.

He smacked her tit, and it wobbled. The sting got her attention. She winced. “Five a side.” He tortured her nipples a little in between the smack and squeezes. 

“Yes, Sir, if it pleases you, sir.” Cal increased the intensity of the clitoral stimulation. She was still on her toes, and the legs were beginning to shake. She has instinctually held the back of his neck for balance. 

He stopped and took a step back. 

Karen crashed onto her heels. The cuff bounced on her hip. She was thrown off balance and dazed by the abrupt halt. Karen said, “Sir?”

“Good Slut. Do you want me to continue?”

“Yes, please, Sir.” She was flushed and felt off-balance with one free hand.

“Look at yourself, all warmed up and ready to cum, but not restrained. Are you prepared to have the other arm restrained?”

She raised the left arm without hesitation. 

SNAP

Karen was spread eagle, restrained, and sexually aroused. Cal stepped back, sat on the edge of the bed, and smiled. “My beauty, you have never looked more spectacular. Shall we continue?”

Karen blew an untamed curl from in front of her eye, grinned, and said, “if that would please you, Sir?”

Cal walked over to the treasure chest pulled out a couple of Velcro straps and a vibrator. “Let’s talk about your journal.”