My brain was in turmoil all day, though, no one seemed to notice, or, at least, nobody mentioned it. No one except Sam, that is. But, he was only interested in what I had done the previous evening that I was so tired. I ignored him. Although, at one point, I did catch myself staring at his ass as I remembered blowing my load in Raymond. Thankfully, Sam didn’t notice that.
That night, as I lay in bed, still wrestling with my thoughts, I finally came to the conclusion, that it didn’t matter whether I was gay, bi, or straight. All that mattered was the pleasure I had received, and given, and that I was okay with that. Once I’d had this epiphany, I quickly drifted off and slept peacefully until, Riley woke me by wrapping her sweet warm lips around my cock. There will never be a better way to be awakened from a deep slumber.
I closed my eyes and stretched as Riley’s lips and tongue massaged my stiff pole. Even as she moved to straddle my hips and engulf my hard member with her hot puss, I found it hard to believe she had chosen me. She could have her pick of guys and, for some reason, she had chosen me. Even harder to believe though, was the way my life had changed since meeting her. She had turned my world on it’s ear, and I loved every second of it.
Her wet hot pussy slid up and down my cock, quickening my pulse while images of her and Jenn, her and Kate, me and Kate, me and Jenn, me and Raymond flashed through my brain. I caressed her small firm tits and her lips locked onto mine as she ground her hips against my own. Sexual heat poured from her into me as our orgasms flared and our bodies convulsed. She collapsed on top of me and we slept with my spent cock still inside her.
On Saturday, Kate called and asked us to stop by the shop that afternoon. Riley slipped into a very little black dress and we made the rounds to every shoe store at the mall before heading over to Kate’s store. Watching the looks on salesmen’s, and two saleswomen’s, faces as they tried not to obviously stare up her tiny dress was quite amusing, and arousing. One of the women, a petite brunette in stiletto heels, even slipped Riley her number before we left. By the time we made it to Kate’s, there was an uncomfortable bulge in my pants, and moisture coating the inside of Riley’s thighs.
Kate was busy with a customer when we walked in. A broad smile spread over her face and she nodded in our direction. Taking my hand, Riley led me back to the toy room and through a side door into a dimly lit room. Once my eyes adjusted to the near darkness, my jaw dropped at what I saw. The walls were padded and covered with leather and red lights glowed around the room. A sex swing hung from the ceiling and a set of rough wooden stocks stood in the corner. A large strange looking chair sat opposite the stocks, in another corner was an examination table, complete with stirrups. Most surprising though, was a naked woman chained to the wall with arms stretched so she stood on tip toes with a dark hood covering her head. She jumped at the sound of our entrance, but didn’t make a sound.
Riley headed straight for the swing, kicking off her shoes and pulling her dress over her head as she went. I hurried after her, stumbling as I struggled to remove my pants. Riley hoisted herself into the swing and lifted her legs so I could secure the straps around her ankles. The swing positioned her perfectly for easy access to her dripping pussy and tight little asshole. I strummed her swollen clit with my thumb absent mindedly as I tried to decide what I wanted to do with her delectable body first.
“Fuck me baby. I need your big cock in me,” Riley said, interrupting my thoughts.
It was my turn to sport a devilish grin and I walked around to secure her wrists to the chains supporting the swing.
“So you need my big hard cock inside you, huh?” I replied.
“Yes, please,” Riley begged.
I smiled down at her, “Okay, open your mouth and I’ll put it inside.”
I grabbed the base of my swollen cock and pressed the tip to her soft pink lips. Riley looked a little shocked, but obediently parted her lips, allowing my thick shaft to slip into her warm mouth. Slowly, I pushed my cock past her lips savoring every millimeter until my sensitive head was lodged securely in her throat. I pulled back enough to allow her to breathe then pushed back in. I reached out with both hands and twisted her nipples as I slowly fucked her pretty face. I was already pretty worked up from the show she had put on for the shoe clerks and the exquisite heat of her mouth had me on the verge of coming. I had no intention of blowing my load before I got my cock in both her pussy and tight ass, so I pulled out of her hungry mouth and took a moment to collect myself.
“There you go, you had my cock inside you. Is that what you needed?” I asked with an evil grin.
“Please, I need you in my pussy,” Riley answered, after catching her breath.
I nodded, circling her suspended body and trailing my fingers lightly over her supple flesh.
“Right here?” I asked, sliding a finger along her thick labial lips.
“Please,” she nodded, attempting to swing her pussy into my hand.
I slid my finger over the thick lips, then reached down to smear the slick juices around her puckered little hole.
“Or here?” I grinned.
Riley bucked her hips, “Oh please,” she begged.
I kissed the inside of her thigh, before trailing my tongue down to her dripping mound. My lips closed over her swollen clit and I sucked hard, flicking my tongue over it as fast as I could.
Riley cried out, bucking her hips against my mouth. I pulled my mouth away and grinned at her. Her head fell back with a whimper and I chuckled at her frustration. I remembered our afternoon in the backyard and was enjoying getting even. I ran my tongue across my lips, savoring her taste as I did.
“Oh, did you want to cum?” I asked with a mocking tone.
“Please Will?” she begged again.
I parted her moist lips with my finger and pushed it slowly into her needy sex. I curled the tip back to find her most sensitive spot and she moaned quietly. I withdrew and waited a minute before repeating the action with two fingers this time. When she moaned, I withdrew again and waited, before adding a third finger, then began slowly stroking her. Riley moaned and started bucking her hips attempting to get more of my fingers inside her. Her moans grew louder and just when I knew she was about to explode, I pulled my fingers from her dripping hole.
“Ahh no!” she groaned.
I grinned down at her and brought my fingers up to taste the sweet juices coating them.
“Mmm looks delicious,” Kate’s voice came from behind me.
I didn’t know when she had come in, or how much she had witnessed, but I turned and offered my sticky fingers to her plump red lips. Kate’s long tongue curled around the bottom of my middle finger and slid out to the end. Her red lips parted and she sucked my finger just as if she were sucking a hard cock. Her lips made a smacking sound as she pulled them from my finger and she smiled seductively.
“Delicious,” she said, turning her attention to Riley.
Kate slid her hand along Riley’s thigh down to her needy dripping pussy and flicked a finger over her clit. Riley moaned and jumped each time Kate’s finger made contact with her sensitive swollen nub.
“Oh somebody wants to come,” Kate said with a mocking tone to her voice.
She slid her hand up over Riley’s flat stomach to caress each small breast and pinch their stiff nipples. Riley whimpered at her touch and Kate leaned down to kiss her. As they kissed, I slid my finger along her thick moist lips, then down to smear the slick juices around her little brown pucker.
Kate pulled her lips away and stepped around in front, Lifting her skirt and placing her pussy on Riley’s mouth. Riley began lapping at the pink lips and Kate let the skirt fall as she reached for Riley’s swollen nipples. I collected more slick juices from Riley’s dripping hole and pushed a finger into her tight pucker. I pumped my finger in her ass, and occasionally lapped her swollen clit with my tongue as I did. Kate’s eyes closed and her breathing grew heavier as Riley’s mouth worked beneath the skirt. I lowered my mouth to Riley’s swollen clit and sucked hard while flicking my tongue over it. Her hips started to shake and she moaned between Kate’s thighs. Again, just as she was about to explode, I stopped, pulling my mouth from her clit and finger from her ass. At the same time, Kate cried out and grabbed the chains supporting the swing as her knees went weak and she came over Riley’s face.
Riley whimpered and bucked her hips in frustration. “Will, please,” her muffled voice begged from beneath Kate’s skirt.
I leaned in close and breathed, “Please what?”
My hot breath on her sensitive swollen clit caused her to jump.
“Please let me come,” she pleaded.
I chuckled in response as I stood and brushed the purple head of my cock over her moist entrance.
“Oh, you want me to let you come all over my hard cock?” I said, trying to sound sincere.
“Yes, please fuck me,” Riley begged.
“Like this?” I asked, pushing my swollen tip between her warm velvety lips.
“Mmmm yessss,” she hissed.
My dick had never been so hard and I wanted nothing more than to drive the full length into her warm dripping tunnel, but I wasn’t ready to end her torment just yet. I fought off the overwhelming urge for release and withdrew.
“My that cock looks so hard, I have just the thing for that,” Kate smiled and walked toward the bound woman against the wall, whom I had completely forgotten about.
Kate unlocked the chains holding the woman and led her to the stocks in the corner. Though her head was covered by the hood, I guessed the woman to be middle aged. She was rather short and plump, but by no means fat. Her round ass and thick thighs were firm and her plump breasts sat high on her chest without sagging. Kate placed the woman’s head and wrists in the stocks and closed them with a resounding thud.
“You’ve done quite well today, as a reward I’m going to allow you to come, while your ass is fucked. Would you like that?” Kate said, in a condescending tone.
“Yes Mistress, very much. Thank you,” a muffled voice answered from beneath the thick hood.
Kate smiled in my direction and nodded toward the plump ass before me. Being bent with her head in the stocks forced the woman’s ass out, and the plump cheeks to part, exposing her tiny puckered opening.
I stepped forward and pressed the swollen head of my cock to her pink hole and the woman stiffened a little. Kate frowned and slapped the woman’s ass.
“I offer you a reward, and you respond to my generosity with resistance?” Kate’s voice grew menacing.
“No Mistress, it just surprised me. I’m sorry Mistress,” the woman cried.
Kate grabbed the woman’s breast roughly and squeezed. “Very well, but don’t embarrass me like that again or you won’t come for a month.”
“I won’t Mistress. I promise. Thank you Mistress,” the muffled voice trembled.
Kate turned and nodded and I pushed my thick head against the tight orifice. Slowly, the tight opening began to yield and the woman grunted as I stretched her. I grabbed her full hips and pushed harder. With another grunt her rosebud opened and the tip slipped in. She was tight and with no lube I wasn’t sure if I could even get the remainder of my stiff cock in. I pushed again and my hard shaft slid further in causing her to moan. Her tight chute squeezed my cock and scratched at the sensitive head as it travelled up into her bowels. It felt so good I could tell I wan’t going to last long and I paused to let myself calm down. I stood there with my stiff cock buried in the ass of a woman who I had never met, and who’s face I hadn’t even seen, while my mother’s friend twisted and pulled at her nipples, and my girlfriend was only feet away naked, bound, and begging to be fucked. The whole scene seemed so surreal and erotic, and it had me about to burst just thinking about it.
Kate’s hand cupping my ass interrupted my thoughts and I began slowly pumping my thick member in the woman’s tight ass. Kate’s fingers slipped between my cheeks and teased my puckered hole. I began driving my cock into the woman’s ass forcing her against the stocks and causing her to moan. Her moans turned to cries and her cries turned to screams as her body started to tremble. Kate’s hand dove between her legs to stroke her clit as she came and her already tight ass clamped around my stiff shaft. The pressure was too much and I filled her with my hot cream. My legs stiffened and my cock twitched as jet after jet shot through it. I held her hips for what seemed an eternity as waves of ecstasy crashed over me.
My spent cock slipped from her ass as I stepped back and cum trickled from her stretched hole. Kate’s fingers continued to stroke the woman’s clit and a river of juices were flowing down her thighs. The woman’s body shook and trembled and her muffled cries filled the room until Kate stopped stroking and she finally went limp.
Kate stepped back and offered her sticky fingers to my lips. I sucked two fingers into my mouth and licked at the sweet juices coating them.
“She’s one of the sweetest I’ve ever tasted,” Kate whispered in my ear.
I nodded in agreement as she pulled her wet fingers from my mouth and returned to release the woman from the stocks. Her legs were shaky and Kate helped support her as she stood. Kate guided her to where I stood.
“Janine, kneel and thank my friend for making you come,” Kate said, her voice much kinder than before.
Janine dropped unsteadily to her knees and Kate removed the hood. It took her eyes a moment to adjust to the light and when they did she quickly hid her face. It wasn’t quickly enough though, in the moment it had taken for Janine’s eyes to adjust, I had clearly seen her face and immediately recognized her.
Kate’s voice was stern, “I told you to thank my friend!”
Janine jumped and lifted her head slightly, “Thank you sir, for fucking my ass and making me come,” she said quietly.
“That’s better, now clean up your mess,” Kate ordered.
Mrs Stalely scurried across the room on hands and knees and returned carrying a bucket of warm soapy water with her teeth. She set the bucket before me and bather my cock and balls with a rag, attempting to hide her face the entire time.
“I’ve already seen your face Mrs Stalely,” I said, rather enjoying the situation.
Mrs Stalely’s class had nearly torpedoed my high school career and she had taken great joy in tormenting me with extra work in order to receive a passing grade. Now I fully intended to get a little payback.
Kate’s eyes opened wide and her scarlet lips formed a wicked smile as her confusion cleared.
“You’re already familiar with your new master, good,” she grinned.
Janine’s expression changed to one of horror as she continued to cleaning my genitals.
“That’s enough,” I said, brushing her hand away roughly. “Open your mouth.”
Mrs Stalely glanced over at Kate. I grabbed a handful of her short black hair and jerked her face around.
“She said I am your new master. Now, open your mouth!” I glared at her.
For a moment I thought she would cry, but her mouth immediately dropped open and I placed the tip of my cock on her tongue.
“Let’s see if your mouth is good for anything, but scolding teenagers,” I sneered, holding her by the hair and pumping my stiffening cock in her mouth.
Janine’s lips closed around my shaft and her tongue began working on the underside. Fucking my former teacher’s mouth soon had my member back to full hardness and I decided to test her limits. I pushed further in prepared to pull back when she gagged, but she never did. Her lips were sealed around the base of my cock and the swollen tip was lodged securely in her throat and she never offered a shred of resistance. I pulled back and she inhaled sharply through her nose while her tongue continued to caress my swollen member. I pushed all the way back in and held her in place. The muscles of her throat squeezed my sensitive tip while her stroked the shaft. She was an amazing cocksucker and quickly had me ready to explode. I yanked her mouth off my cock and sneered down at her.
“Hmm your pretty good with a cock. Let’s see how you do with pussy,” I said.
I led Janine, by the hair, over to Riley and placed her face between Riley’s thighs.
“Suck her pussy, but don’t let her come,” I ordered.
Janine began lapping at Riley’s thick moist lips and I released my grip on her. Kate had removed her clothes and followed us to the swing. She offered her plump breast to me and I took the stiff nipple between my lips while reaching for her slick sex. She began stroking my stiff cock as I plunged to fingers deep into the wetness between her lags.
Riley had begun to moan under the ministrations of Janine’s tongue.
“Don’t let her come,” I growled, “lick her ass!”
Janine, dutifully, began tonguing Riley’s ass and I returned to sucking Kate’s nipple. Her juices were flowing steadily, coating my hand and she pulled away.
“I need you inside me,” she whispered, leading me around to Riley’s head.
Kate positioned her pussy directly over Riley’s face and leaned forward placing her hands on Riley’s firm tits. I stepped up behind her and ran the tip of my cock over Riley’s lips before pushing it into Kate’s waiting pussy. I began slowly pumping in and out and felt Riley’s tongue on the bottom of my shaft as she lapped at Kate’s swollen clit. My hands slid over the flesh of Kate’s back and up to grip her shoulders as I began pumping her harder.
“Mmm yessss that’s it, fuck me like a man,” Kate moaned, bending lower and pushing her ass out.
I started slamming into her thrusting with all the force I could muster. My balls were slapping Riley’s face as the force of my thrusts caused Kate’s body to shake with the pounding she was getting. I was grunting with every effort and another orgasm was beginning to build in my balls when Kate cried out and started to shake. I squeezed my muscles tight preventing my own orgasm as her pussy quivered and her juices washed over my cock. I held out while Kate quivered in ecstasy then pulled my stiff cock from her dripping snatch and hurried around to push Janine out of the way and bury it in Riley’s tight sheath.
I held Riley’s waist and resumed where I had stopped with Kate, driving my stiff rod into her as hard and fast as I could. Kate was still squeezing her tits and Riley cried out with each stroke as I pummeled her. Blood roared in my ears and lights flickered in my eyes as the need to come rose in my balls as sweat ran down my back. With one last powerful thrust, my teeth clenched and I exploded in her tight tunnel. My whole body jerked and I felt Riley tighten around my twitching shaft and I grunted deep in my chest as the pleasure took my breath away. My knees went weak and my cock slipped from her sweet hole with a wet pop. On wobbly legs, I sunk to the padded floor and gasped for breath.
I leaned back on my arms and stared up at Riley’s thick luscious lips as pearly white cream leaked out and trickled down over her exposed brown pucker. I noticed Mrs. Stalely out of the corner of my eye. She was kneeling just to the side of the swing waiting for direction.
“Clean her up,” I ordered, still panting for breath.
Mrs. Stalely crawled between Riley’s suspended legs and traced the trickle of cum from her asshole up to her dripping lips.
“Oh, I have customers,” Kate suddenly announced and hurried out the door, pulling her skirt down over her round ass as she went.
I wondered how she knew she had customers until, I noticed the small monitor above the door. I could see two customers were browsing through the lingerie section and Kate rushing to greet them. A quiet moan from Riley drew my attention away from the monitor and I turned back to my naked former teacher sucking my cum from my girlfriend’s pussy. I admired Mrs. Stalely’s full round ass and narrow waist, with the baggy sweaters and thick dresses she always wore at school, no one would ever suspect the attractive body that was underneath.
“That’s enough. Now come clean my cock for me,” I commanded.
Mrs. Stalely instantly turned on her knees and crawled between my knees. She lowered her face without ever looking up at me and sucked my spent sticky cock into her mouth.
“Look up at me. I want to see your face while you’re cleaning the cum off my cock,” I said, still getting a thrill out of ordering my former strict teacher around.
Janine slowly lifted her eyes to meet mine with her lips sealed around the base of my cock. The humiliation was plain to see in her brown eyes and I wondered how many of her former students would enjoy taking revenge on her like this.
“Don’t forget my balls,” I grinned down at her.
Her warm tongue snaked out around my pole and lapped at my sack as her mouth began to revive my flagging member. I leaned back on my elbows and let her work my shaft until I was fully hard again. She could definitely teach a class in cock sucking, that’s for sure.
“That’s enough, for now,” I said, pushing her away.
She looked at me with a slightly hurt look as I stood and went to Riley. I undid the straps holding her ankles, then the ones holding wrists, and helped her down from the swing. Once on her feet, Riley wrapped her arms around me and crushed her firm tits into my chest.
“That was amazing,” she said, rising up on her toes to kiss me.
I held her for a moment while we kissed and let my hands roam over her soft warm flesh.
“What should we do with her?” I asked, turning and nodding toward Mrs. Stalely.
Riley circled the kneeling woman, running her fingers through her short hair. “She seemed to enjoy eating your cum, maybe we should give her some more,” she said, balling her fist in Mrs. Stalely’s hair.
“No, she hasn’t earned that. I have a better idea,” I said, noticing a table near the wall with an assortment of dildos and butt plugs on it.
I walked to the table and Riley followed, leading Janine by the hair. I perused the various items on the table and selected a rather large black butt plug. I turned, holding the plug so Janine could see, and sat on the edge of the table.
“Show me your tits,” I ordered.
Riley pulled Janine up to her knees, then released her grip and joined me by the table. Mrs. Stalely straightened her back and pushed her chest out, displaying her large firm breasts. I slipped my arm around Riley’s shoulders as I ogled Janine’s breasts and their small pink caps.
“Play with your nipples,” I said flatly.
Mrs. Stalely swallowed as her hands rose and she began pinching and stroking her nipples. Riley’s hand slid down over my thigh and she began fondling my balls as we watched the older woman twist and stroke her own nipples. I reached around and started lightly circling Riley’s puffy nipple with my fingertip and tossed the thick butt plug on the floor between Mrs. Stalely’s knees.
“You know what to do with this, don’t you?” I said, staring her in the eye.
Mrs. Stalely picked up the toy and nodded. “Yes Master,” she said quietly.
“Then do it! I don’t have all day to wait for you,” the harsh tone in my voice even surprised me a little.
Janine rose up on her knees and reached between her thighs to position the toy at her rear entrance. She took a deep breath and lowered herself onto the thick plug. She whimpered and her round face twisted into a grimace as her tight hole stretched to accommodate the thick plug. She bit her lip and breathed again, trying to relax her muscles as she pushed down. After rocking forward and back a few times, her round cheeks touched the floor and the large plug was fully inserted.
“Now show me your pussy,” I commanded.
Janine sat back on her plump cheeks, her eyes fluttering as the large plug shifted in her bowels. Her thick thighs spread wide, exposing her delicate pink flower and small tuft of black hair just above. Her puffy lips were dripping with evidence of her arousal.
“Touch yourself,” I demanded.
Mrs. Stalely continued fondling her breasts with her left hand while her right slid down over her rounded belly and began rubbing her swollen clit. Riley’s fingers lazily stroked the length of my stiffening shaft and I let my hand slip down to her plump mound as we watched my former teacher masturbate. I glanced over to the monitor above the door and saw Kate still assisting two women in the lingerie section.
“Is that Principal Simmons?” I asked trying to sound surprised and watching Janine out of the corner of my eye.
Mrs. Stalely instinctively turned to look.
“I did not give you permission to stop touching yourself,” I roared, before she could get a look at the monitor. I recalled a line Mrs. Stalely was found of using on her students when they’d made mistakes. “Are you incapable of following simple instructions?” I asked, trying not to smile as I spit her own words back at her.
Janine stared up at me and jammed two fingers into her dripping hole. “No Master. I’m very sorry Master.”
“Does Principal Simmons know what a disobedient slut you are? Maybe I should invite him to come see the real Mrs. Stalely,” I threatened.
A look of shear terror crossed Mrs. Stalely’s round face even as slick juices began pouring from her pink lips.
“On your knees,” I said, walking past her toward the rack of paddles and whips.
Riley grabbed Mrs. Stalely by the hair and followed as I examined the punishment devices on the wall. Most of the whips seemed too extreme to me and I selected a leather paddle that I thought less likely to cause injury. Taking the paddle down, I ran my hand over the smooth leather and lightly tapped it on my palm. I was surprised such a light tap caused such a sting. I turned and held the paddle for Mrs. Stalely to see.
“Stand up and bend over,” I ordered, “maybe this will teach you to follow directions.”
Riley pulled Janine up by her hair as she stood, then forward and down as she bent to grab her ankles. I stepped beside Mrs. Stalely and prepared to deliver her punishment. I hesitated, unsure how hard or how many strokes to give her. Seeing my confusion, Riley took the paddle and began rubbing it in circles on Janine’s plump cheek. After three or four circles she lifted the paddle and popped it against the creamy flesh, then moved to the other cheek and repeated the action. Riley gave her six strokes always moving the paddle to a new spot on the plump cheeks with each one. She now returned the paddle to me and guided my hand for the first stroke to demonstrate the force for me.
Riley stepped aside and I gave Mrs. Stalely another five strokes, admiring the way her creamy flesh turned pink, then red as I punished her. Though Janine whimpered with each stroke and tears streamed down her face, a glance between her legs revealed a river of fluid running down her thighs. I pressed on the base of the plug filling her ass and rocked it within her, bringing a groan from her.
“I think, maybe, I should go get Principal Simmons and let him continue your punishment,” I announced.
Janine moaned and started to tremble as a fresh gush of moisture erupted from her sex. I brought the paddle down on her backside again, harder this time.
“You’d like that, wouldn’t you?” I accused, “Filthy slut! You dream about being bent over his desk while he paddles your ass, don’t you?”
Janine didn’t answer, but moaned loudly, and her pussy had become a virtual river of fluids. I gave her five more hard strokes with the paddle, alternating cheeks with each one. I couldn’t believe the way she was reacting to her punishment and watching her body respond had my cock throbbing with excitement. I dropped the paddle and jammed my shaft into her dripping hole. I was overcome with the need to fuck her. I grabbed her hips and rove my rod into her over and over as hard as I could. She cried out and began trembling as I filled her tight hole and slammed my hips into her, repeatedly. Riley reached up to pinch my as she pressed her lips to mine. I kissed her hard as I exploded in Janine’s tight sheath filling her with hot cum.
I released my hold on Janine’s hips and pulled Riley against me as we continued to kiss. Janine collapsed to the floor, her body still trembling with pleasure. Riley wrapped her fingers around my twitching shaft sending another intense shiver through me as we kissed. My knees felt weak and I slumped to the floor, pulling her down atop me.
We lay on the floor resting when I felt something warm on my spent cock. Looking down, I discovered Mrs. Stalely with her lips wrapped around my member. She slowly pulled her lips up the length of my shaft sucking her own juices as well as mine from my dick. My thick head popped from her lips with a wet pop.
“Thank you Master,” she sighed.
