My Mom s Affair With Her Boss
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Years ago I started the second job I'd ever gotten; Sales Associate at Hot Topic. It wasn't prestigious by any means, but I chased after it pretty hard. I was 16, it sounded cool, and it felt like a supreme upgrade from 'fry cook'. After the first three months I would find out if I'd be kept on past the Christmas season, rather than the other two people that had been hired.
During the winter break from school I worked 14 of the 17 days we were out, covering for people's shifts or being available to come in when called, hoping that it would further improve my chances of staying. I was scheduled out at the same time our general manager was, one week before Christmas, and thought it would be a good opportunity to walk out together and try to suss out my standings. 8:00 PM arrived, I pretended not to notice because the boss wasn't clocking out yet. It finally happened, and we walked to the mall entrance where our cars are parked. We made small talk about how crazy work was all day, and joked around like everyone there always did, until we stepped outside into the fresh and still falling snow. I shivered, my jacket wasn't heavy enough for the weather. My manager lit a cigarette, took a hit, and looked at me in an unfamiliar way.
She abruptly asked, "So do you like it here?"
"I love it!" I spouted. A little heavy handed, given what my goal was, but I was new to all of this. I continued, "Even the worst parts of the job are still fun because of the crew here."
"I take it you would be interested in staying on after the season is over then?" She inquired with obnoxious dramatic pauses in the syllables, probably because she could tell how nervous I was.
"Of course!"
She chuckled at me and smiled, "Well, you can't mention it to anyone yet, but we're keeping you."
I don't know if it was the cold, the smoke, the excitement, or all of them combined; but I had tears on my cheeks as I thanked her profusely.
"Aww, buddy come here." She hugged me and I hugged her back, it was exactly what I needed. I wasn't thinking too clearly in the moment, because after the first few seconds, I moved my hand from her shoulder to the back of her head and pulled her closer. She didn't resist it, but something made me feel like I shouldn't have done it. We both awkwardly pulled away at the same time and laughed a little. She took another hit of the cigarette, and got a look in her eyes that made it seem like she was about to say something.
I was frozen, panicking about what I had just done, and wondering why. I tried rationalizing why to myself, and couldn't. I saw her differently, and couldn't understand how I didn't find her attractive before. It was all I could think about while I waited for her to speak.
I could see her deep hazel eyes through the smoke, and the flawlessly maintained dreadlocks framing her face as it cleared. Most of them brown, her natural color, with a few colored blonde, tan, black, red, purple, blue, grey; all in a pattern that seemed to pull your eyes to hers. It was having an intoxicating effect on me. Her usual work attire was unflattering, but today under that coat she had on a thin tank top and matching bra, making her 36D breasts impossible to miss, hugging the curves of her torso. Her jeans looked a size too small, taut against her plump ass and nicely shaped calves, tucked into her boots. I wanted her, badly, and couldn't do a thing but stand there waiting for her to speak.
She hit her cigarette then tossed it and looked me in the eye, "Well, I'll see you again tomorrow, good night."
"Good night," I returned, reeling from the excitement and confusion I walked toward my car.
I was relieved that she decided to ignore it at first, but I never stopped wondering what she stopped herself from saying.
*
A year and a half later
Tara was throwing a party for the staff. I hadn't tried anything since that awkward hug we had, mostly to avoid causing problems at work. I still had a strong attraction to her, and was a little worried about being in her house. Most of our people were already there when I showed up; drinking, smoking, and watching terrible movies. As the night went on people were coming and going, eventually Tara, myself, and 2 others were the only ones left. We all stepped outside to smoke, and the other two both said they needed to get going.
As they pulled away I realized we were alone just like that night, and began to feel very anxious
I took a hit of my cigarette and looked right at Tara, seeing her eyes through the smoke, just like before.
"I guess I should get going after this, let you bring this party to a close," I said, a little uncomfortably
"Yeah it's getting pretty late." She tossed her cigarette and I did the same. When she exhaled her hit it was more than I could handle, the adrenaline was overwhelming.
I stepped toward her to give her a hug, and she returned it.
'You can't back out now, just go for it' I kept screaming at myself.
I moved my hand to her head to pull her in close, and she leaned into me. I could feel her breasts pressing against me, her head against my chest, her arms around me, my fingers entwined in her locks. I was going mad. I had never been so aroused in all my life.
I started running my hand through her hair, fearing it would make her pull away, knowing I had to take the risk. I had to, at the least, get a real rejection so I could let the attraction go. She shifted her arms, and I knew that meant the window was closing. She pulled back slightly, turning to face me as she did.
'Now or never' I thought.
As she began moving her arms back to her sides I went for it. I looked into her gorgeous hypnotic eyes, and leaned in to kiss her.
With my hand still on her head I felt her pull back at first, and let go, feeling defeated. As I lifted my hand away, she didn't break away from the kiss. We stood motionless, our closed lips lightly touching each other, for almost a full minute before she tilted her head away, looking into my eyes. I wasn't afraid anymore, and she hasn't tried to stop me once.
I met her gaze for a moment, slowly wrapping my arms around her again. She smiled as my hand rose to her head and I kissed her again. This time our lips parted immediately, our tongues ravishing each other, her moaning when I pulled at her hair, my moans mixing with hers when I felt her tits against me, her nipples poking me through the fabric.
We went on for 10 minutes without exploring each other's bodies, just running our hands through each other's hair, practically swallowing each other's tongues, we were both so forceful. Tara broke the kiss and stepped back from me.
I was fully erect and there was no hiding it. Her hair was a mess, and we were both breathing heavily.
"Do you want this?" she asked
"Yes I do. I want it more than you can imagine," I declared.
"You won't be getting what you're expecting." She strode toward me as she said it, grasping my hard cock through my pants when she reached me. I kissed my way to her neck, biting and nibbling at her ear. I moaned with desire right into her ear as she squeezed my cock harder. I bit into her neck again as I reached her breast with one hand and tugged at her hair with the other, all the while we were moving closer to her door. As we got to the door I moved to feel her tongue in my mouth again, and she grabbed my hair and stopped me from leaning in to kiss her.
She held me still like that, staring into my eyes, stroking my cock through my pants. She unzipped them and freed my cock without letting me move, rubbing the head slowly with nothing but her thumb and forefinger until I couldn't keep from crying out in pleasure and agony.
The second I made the sound she gripped my shaft so hard I thought she might tear it off.
"This won't be going inside me." Still crushing my cock in her palm, stroking me in sync with every word, it was torture.
"You won't feel my tight wetness enveloping it, not that filthy thing."
Tara put more pressure on my shaft, I began to feel lightheaded.
"You'll be lucky if I touch it again after we go inside. This worthless thing protruding from you is disgusting to me. Your orgasm is not important to me."
Releasing the shaft, she moved to my balls, cupping them. She slowly crushed them as she asked, "Do you understand?"
I barely managed to whisper, "Yes Tara."
"Good boy. Once we get inside you are not to touch your cock. If you do, I will tie your hands and gag you. If you are going to cum tonight, it will happen while I am fucking you. It will happen when my strap-on is pounding relentlessly against your prostate. It will happen while you're gagging on it. Understand?"
I couldn't believe any of what I was hearing, or how good the pain she was inflicting on my member felt. It wasn't at all what I expected, but the thought of it was turning me on so much that all I managed to say was, "Yes Tara."
"Good boy. Are you ready to feel what you'll be missing? So you can imagine what it might be like? So you can use those thoughts when you and your stupid meat stick are all alone?"
She took my hand up her skirt and forced three of my fingers into her. It was the tightest pussy I have ever felt. "But you aren't getting in here. This is off limits to you." She put my fourth finger into her slit, and locked eyes with me as she fucked herself with my hand, knowing it was almost enough to make me cum just watching her.
"Keep your hand still, I'm going to make myself cum while I punish your cock. It's the closest your cock will ever get to actually pleasing me."
She let go of my hand and started gyrating on it, getting herself off as she resumed torturing my member with her hands. I was in so much pain I couldn't think, all I could do was focus on her through the tears, watching the elation dance across her face as she approached her climax.
She suddenly applied insane pressure with both hands and I let out of shriek of pain, at which she giggled.
"Turn to the side, keep your hand in place." She released my throbbing organ as I did what she commanded. She paused her gyrations.
"Look at me. Drop your pants. Don't make a sound until you hear me finish and feel it on your hand, or it will get worse."
Leaning her shoulders against the door she angled my fingers to hit her g-spot as a very evil grin reached her lips. She began riding my fingers and sliding her middle finger into my ass without warning. The nail hurt, I couldn't help myself; I screamed out in pain.
Her smile somehow grew wider as she pulled out, and slammed two fingers home even harder, curling them inside me, scraping at my insides. I screamed again, even louder, and she pulled out. Tara's eyes seemed beyond gleeful, and she began laughing and riding my hand harder. Still cackling at me, she forced three fingers into me, I bit into my cheek, hard, and managed to hold it in this time. This upset her, and she began fucking my ass with her hand more vigorously than she was working her own pussy. I couldn't take it, it was too much
"Please, Tara, it hurts! I can't, please, Tara!"
Her body was shivering as I begged, her hand slid out of my ass, and by the time I finished pleading, her eyes were rolling back in ecstasy and my hand was being drenched in her sweet release.
I leaned against the door, unable to hold myself up any longer. Tara straightened her skirt, pushed her locks out of her eyes, and looked at me with what I knew to be tremendous desire.
"I have to get ready, why don't you take your clothes off and rest on the couch while I do. You're going to need it, I haven't even gotten started yet."
*
I sat there waiting for her to come out, excited and terrified of what was about to happen. It felt like an eternity before I heard the door open and she entered the room.
I was stunned. The red and black leather corset that barely contained her breasts was what I noticed first, I was rock hard in seconds. She had changed her skirt to a longer one matching the corset, made entirely of leather belts. She still had the same boots on, and by the time my eyes made it that far down her body, I was drooling.
"You will call me Miss Tara from now until I have finished. Calling me anything else will be painful for you. You will do exactly what I say, when I say it. Hesitation will be painful for you. You will not let yourself cum until I have finished. If you do, it will be painful for you. Are you ready, boy?"
Shocked by her appearance and what she was saying, I made my first mistake.
"Yes Tara." Instantly I realized what I had done wrong, but it was too late. That grin lit her face again, and she crossed the room to where I was sitting. Pointing to the belt at the top of her skirt she said, "Unfasten it with your teeth quickly, and I will forgive you this once."
I but down on the metal and tried to open it three times before she backhanded me so hard I fell off of the couch. Undoing the belt herself she said, "So much for forgiveness. Get back in your seat."
I righted myself on the couch just in time to see her skirt fall from her waist to the floor. I gasped as a massive purple strap-on popped out and hit my cheek. I knew she wanted me to suck it, but I was waiting for instruction this time. She put a hand around my throat and used the other to open my mouth. Still holding my throat, she spit on her other hand and started stroking her strap-on, pushing the other end in and out of herself.
"It's beautiful isn't it? Nothing like that filthy piece of meat sitting up like a pathetic puppy dog in your lap right now. You want to take the whole thing down your throat don't you? You want to feel every inch of me inside you. Say it."
"I want to take the whole thing down my throat. I want to feel every inch of you inside me, Miss Tara."
She backhanded me again, harder this time. My cheek was on fire.
"I didn't tell you to say my name. Pay attention, boy. Now, start sucking, and don't stop until you can get the whole thing down."
I held the huge purple cock in my hand, dripping with her saliva still, and started sucking. I got the first 4 inches down easily, but gagged a little when I tried to go further. I pulled back up to the head and started again, slowly working my way to the base. I got past 5 inches and looked up to see Tara's face. She was smiling wide, her hazel eyes seemingly on fire, and the moment I saw them, I had to get the rest down like she asked. I had to swallow her entire cock while we stared into each other. I gagged on the 7th inch and had to come up for air. I saw her eyes widen when my mouth left the head, and knew I'd made another mistake. She grabbed my chin, pointed my face up at hers, and spit on me.
"Until all 8 inches make it down your throat, you don't let it out of your mouth. Open wide!" I did as I was told, and she spit into my mouth this time.
"Swallow it." I did.
"Now let's try this again."
I took the head back in my mouth, and heard the click of a lighter as I went down the shaft. I looked up to see her exhale into my face. I had never seen anything so hot before, and I forced the last two inches into me, fighting the gag reflex, choking, barely keeping it down. I pulled back to the head and looked up for another exhale from her.
"Good boy! You're almost there!"
I got a sinking feeling as she pulled more of the other end out of herself, and gave me a look that said, 'Well what are you waiting for?'
I knew I had to find a way to take the 11" she had in front of me or that cigarette was getting put out on me, and I didn't like the thought of where she would do it.
I bobbed up and down on her cock, trying to relax my throat for the full length. I needed to see her exhale into my face again to make it to the hilt, so I stopped at 3" and looked up at her.
As if she had read my mind she teased in lilting syllables, "What is it boy? You need a little encouragement?" She held the cigarette less than an inch from her mouth and started to bite her lower lip. I started moving farther down her cock, slowly, and she finally drew a hit. I backed up to the head and drew my knees up onto the couch, angled my back to straighten out my throat. I looked up at her, and began sliding her entire length into my mouth. The last 2" hurt, a lot, in one of the best ways I've ever felt. I knew I couldn't hold it long, and I barely held back my climax when she exhaled in my face the second I got her cock down. Letting the cigarette dangle from her lips, she grabbed the back of my head and forced another inch of her cock into my throat from her pussy, spit in my face, then slowly removed her entire length from me, most of it returning to her tight crevice. She held the cigarette out for me to hit; she could tell I needed it.
"You're off to a good start, if you keep it up I might let you finish yourself off to the sight of me." Every word she said to me sounded sinister and seductive. The lust I felt for her was growing exponentially by the minute. I knew I couldn't take control of the situation, but I was certain she would enjoy it if I begged.
"Miss Tara, will you please fuck me? Please? I want to feel you bucking in and out of me, I want to feel the power of the thrusts as you climax. Please, Miss Tara?"
She saw right through it, was aware that I was trying to find a way to steer our little escapade.
But I had followed the rules, and she rewarded me for it
"Of course I will, little boy, what else could you possibly be good for?"
She smiled, leaning down to kiss me. The kiss broke quickly, as she grabbed me by the throat with one hand and my balls with the other, roughly forcing me onto the floor on all fours. I was grateful for the deepthroating treatment now, because without warning, she got on her knees behind me and thrust 4" in. If I hadn't gagged and spit so much, her dry cock would have ripped me. I cried out in pleasure and pain, my asshole feeling so full, knowing she had so much more to fit into me. I screamed and moaned with every thrust, finding it harder and harder to remember that her cock wasn't infinite in size. She kept putting more of it into me, until I stopped crying out because I was out of breath. She made one more thrust, keeping her thighs pressed against my ass instead of pulling back this time. My cock was throbbing, and bigger than I'd ever seen it before. I wanted to relieve myself so badly it felt impossible to resist.
I heard a click of some kind from behind me, and without pulling her thighs back I felt more of her enter me, it was unbearably orgasmic, feeling so full of her. Then I felt her thighs withdraw, but the fullness of her cock stayed. I heard her boots on the floor as she walked around in front of me. The strap-on was no longer attached, she had left it inside of me.
"I didn't feel like cumming yet. I'm going to have another smoke while you wait. Enjoy it, this is what you wanted. You wanted to be with me, and this is what that means." She lit her cigarette and knelt down to face me.
"When I start again, you will use that pathetic body of yours to make me cum. You will do the work, or I will have to find a more degrading way for you to get me there. Do you understand?"
"Yes, Miss Tara. I understand."
She kissed me deeply and passionately, and the fullness of her cock brought me to the edge. Thankfully she stopped in time.
"Then I think you're ready."
She spit in my face again, and the impact of it almost triggered my orgasm. She exhaled at me and sat the cigarette in the ashtray.
"You have until that goes out to work that ass and make me cum."
She knelt behind me, yanked more than half of her cock back out, and hooked it back into her harness. I could hear it sliding into her, she was dripping wet. I was determined to make her cum, and I knew just what to do.
She started thrusting into me hard and fast, more forceful than anything she had done yet. I waited for her to put herself deep into me, and clenched myself around her cock as hard as I could. She couldn't draw anymore of her cock back out of me. She began pumping and pounding me furiously, bringing almost all of the length of her in and out of her gloriously tight little box. I felt her start to shake and began thrusting back at her while she shuddered in the throes of a massive orgasm, moaning at the top of her lungs. I didn't stop bucking against her until she pulled out of me, collapsing against the couch behind us, out of breath and obviously satisfied. I turned around to check the ashtray and the cigarette was still burning. I picked it up and brought it to her. "You did much better than I would have expected. Being a good sub isn't a skill many people pick up so quickly. You didn't even touch yourself or blow your load. I'm impressed."
She hit the cigarette and passed it to me.
"I think it's very important in a Dom/sub relationship, for the Dom to make sure to bring the sub back to a safe state of mind afterward, and not to let them become confused about their value. You are not worthless, that talk is just for the act. That's why I didn't want you to cum, I would like to bring you back to baseline."
I handed the cigarette back to her, and she took a long draw, then blew it in my face again.
"Would you like to cum in my mouth, baby? Would you like me to take you down my throat? I think you've earned it."
"Yes, Miss Tara, I would love that."
She put the cigarette out and crawled on top of me, kissing me with furious passion, quickly working her mouth down my body, stopping just before my cock to lock eyes with me as she took my entire length down effortlessly. Cupping my balls, never breaking eye contact, she moved her mouth up and down my full shaft rhythmically and sensually, and I knew I wasn't going to last much longer.
"I'm gonna cum, Miss Tara, I'm gonna cum."
She quickly took all of me into her mouth, and let every rope of cum shoot straight down her throat, not coming back up until I was shaking bodily from the over-stimulation of her tongue working around me.
She smiled as she climbed up to kiss me.
She nestled against me, and we lay there entwined until morning.
We never spoke of that night again, which has made it so much more magical to me.
During the winter break from school I worked 14 of the 17 days we were out, covering for people's shifts or being available to come in when called, hoping that it would further improve my chances of staying. I was scheduled out at the same time our general manager was, one week before Christmas, and thought it would be a good opportunity to walk out together and try to suss out my standings. 8:00 PM arrived, I pretended not to notice because the boss wasn't clocking out yet. It finally happened, and we walked to the mall entrance where our cars are parked. We made small talk about how crazy work was all day, and joked around like everyone there always did, until we stepped outside into the fresh and still falling snow. I shivered, my jacket wasn't heavy enough for the weather. My manager lit a cigarette, took a hit, and looked at me in an unfamiliar way.
She abruptly asked, "So do you like it here?"
"I love it!" I spouted. A little heavy handed, given what my goal was, but I was new to all of this. I continued, "Even the worst parts of the job are still fun because of the crew here."
"I take it you would be interested in staying on after the season is over then?" She inquired with obnoxious dramatic pauses in the syllables, probably because she could tell how nervous I was.
"Of course!"
She chuckled at me and smiled, "Well, you can't mention it to anyone yet, but we're keeping you."
I don't know if it was the cold, the smoke, the excitement, or all of them combined; but I had tears on my cheeks as I thanked her profusely.
"Aww, buddy come here." She hugged me and I hugged her back, it was exactly what I needed. I wasn't thinking too clearly in the moment, because after the first few seconds, I moved my hand from her shoulder to the back of her head and pulled her closer. She didn't resist it, but something made me feel like I shouldn't have done it. We both awkwardly pulled away at the same time and laughed a little. She took another hit of the cigarette, and got a look in her eyes that made it seem like she was about to say something.
I was frozen, panicking about what I had just done, and wondering why. I tried rationalizing why to myself, and couldn't. I saw her differently, and couldn't understand how I didn't find her attractive before. It was all I could think about while I waited for her to speak.
I could see her deep hazel eyes through the smoke, and the flawlessly maintained dreadlocks framing her face as it cleared. Most of them brown, her natural color, with a few colored blonde, tan, black, red, purple, blue, grey; all in a pattern that seemed to pull your eyes to hers. It was having an intoxicating effect on me. Her usual work attire was unflattering, but today under that coat she had on a thin tank top and matching bra, making her 36D breasts impossible to miss, hugging the curves of her torso. Her jeans looked a size too small, taut against her plump ass and nicely shaped calves, tucked into her boots. I wanted her, badly, and couldn't do a thing but stand there waiting for her to speak.
She hit her cigarette then tossed it and looked me in the eye, "Well, I'll see you again tomorrow, good night."
"Good night," I returned, reeling from the excitement and confusion I walked toward my car.
I was relieved that she decided to ignore it at first, but I never stopped wondering what she stopped herself from saying.
*
A year and a half later
Tara was throwing a party for the staff. I hadn't tried anything since that awkward hug we had, mostly to avoid causing problems at work. I still had a strong attraction to her, and was a little worried about being in her house. Most of our people were already there when I showed up; drinking, smoking, and watching terrible movies. As the night went on people were coming and going, eventually Tara, myself, and 2 others were the only ones left. We all stepped outside to smoke, and the other two both said they needed to get going.
As they pulled away I realized we were alone just like that night, and began to feel very anxious
I took a hit of my cigarette and looked right at Tara, seeing her eyes through the smoke, just like before.
"I guess I should get going after this, let you bring this party to a close," I said, a little uncomfortably
"Yeah it's getting pretty late." She tossed her cigarette and I did the same. When she exhaled her hit it was more than I could handle, the adrenaline was overwhelming.
I stepped toward her to give her a hug, and she returned it.
'You can't back out now, just go for it' I kept screaming at myself.
I moved my hand to her head to pull her in close, and she leaned into me. I could feel her breasts pressing against me, her head against my chest, her arms around me, my fingers entwined in her locks. I was going mad. I had never been so aroused in all my life.
I started running my hand through her hair, fearing it would make her pull away, knowing I had to take the risk. I had to, at the least, get a real rejection so I could let the attraction go. She shifted her arms, and I knew that meant the window was closing. She pulled back slightly, turning to face me as she did.
'Now or never' I thought.
As she began moving her arms back to her sides I went for it. I looked into her gorgeous hypnotic eyes, and leaned in to kiss her.
With my hand still on her head I felt her pull back at first, and let go, feeling defeated. As I lifted my hand away, she didn't break away from the kiss. We stood motionless, our closed lips lightly touching each other, for almost a full minute before she tilted her head away, looking into my eyes. I wasn't afraid anymore, and she hasn't tried to stop me once.
I met her gaze for a moment, slowly wrapping my arms around her again. She smiled as my hand rose to her head and I kissed her again. This time our lips parted immediately, our tongues ravishing each other, her moaning when I pulled at her hair, my moans mixing with hers when I felt her tits against me, her nipples poking me through the fabric.
We went on for 10 minutes without exploring each other's bodies, just running our hands through each other's hair, practically swallowing each other's tongues, we were both so forceful. Tara broke the kiss and stepped back from me.
I was fully erect and there was no hiding it. Her hair was a mess, and we were both breathing heavily.
"Do you want this?" she asked
"Yes I do. I want it more than you can imagine," I declared.
"You won't be getting what you're expecting." She strode toward me as she said it, grasping my hard cock through my pants when she reached me. I kissed my way to her neck, biting and nibbling at her ear. I moaned with desire right into her ear as she squeezed my cock harder. I bit into her neck again as I reached her breast with one hand and tugged at her hair with the other, all the while we were moving closer to her door. As we got to the door I moved to feel her tongue in my mouth again, and she grabbed my hair and stopped me from leaning in to kiss her.
She held me still like that, staring into my eyes, stroking my cock through my pants. She unzipped them and freed my cock without letting me move, rubbing the head slowly with nothing but her thumb and forefinger until I couldn't keep from crying out in pleasure and agony.
The second I made the sound she gripped my shaft so hard I thought she might tear it off.
"This won't be going inside me." Still crushing my cock in her palm, stroking me in sync with every word, it was torture.
"You won't feel my tight wetness enveloping it, not that filthy thing."
Tara put more pressure on my shaft, I began to feel lightheaded.
"You'll be lucky if I touch it again after we go inside. This worthless thing protruding from you is disgusting to me. Your orgasm is not important to me."
Releasing the shaft, she moved to my balls, cupping them. She slowly crushed them as she asked, "Do you understand?"
I barely managed to whisper, "Yes Tara."
"Good boy. Once we get inside you are not to touch your cock. If you do, I will tie your hands and gag you. If you are going to cum tonight, it will happen while I am fucking you. It will happen when my strap-on is pounding relentlessly against your prostate. It will happen while you're gagging on it. Understand?"
I couldn't believe any of what I was hearing, or how good the pain she was inflicting on my member felt. It wasn't at all what I expected, but the thought of it was turning me on so much that all I managed to say was, "Yes Tara."
"Good boy. Are you ready to feel what you'll be missing? So you can imagine what it might be like? So you can use those thoughts when you and your stupid meat stick are all alone?"
She took my hand up her skirt and forced three of my fingers into her. It was the tightest pussy I have ever felt. "But you aren't getting in here. This is off limits to you." She put my fourth finger into her slit, and locked eyes with me as she fucked herself with my hand, knowing it was almost enough to make me cum just watching her.
"Keep your hand still, I'm going to make myself cum while I punish your cock. It's the closest your cock will ever get to actually pleasing me."
She let go of my hand and started gyrating on it, getting herself off as she resumed torturing my member with her hands. I was in so much pain I couldn't think, all I could do was focus on her through the tears, watching the elation dance across her face as she approached her climax.
She suddenly applied insane pressure with both hands and I let out of shriek of pain, at which she giggled.
"Turn to the side, keep your hand in place." She released my throbbing organ as I did what she commanded. She paused her gyrations.
"Look at me. Drop your pants. Don't make a sound until you hear me finish and feel it on your hand, or it will get worse."
Leaning her shoulders against the door she angled my fingers to hit her g-spot as a very evil grin reached her lips. She began riding my fingers and sliding her middle finger into my ass without warning. The nail hurt, I couldn't help myself; I screamed out in pain.
Her smile somehow grew wider as she pulled out, and slammed two fingers home even harder, curling them inside me, scraping at my insides. I screamed again, even louder, and she pulled out. Tara's eyes seemed beyond gleeful, and she began laughing and riding my hand harder. Still cackling at me, she forced three fingers into me, I bit into my cheek, hard, and managed to hold it in this time. This upset her, and she began fucking my ass with her hand more vigorously than she was working her own pussy. I couldn't take it, it was too much
"Please, Tara, it hurts! I can't, please, Tara!"
Her body was shivering as I begged, her hand slid out of my ass, and by the time I finished pleading, her eyes were rolling back in ecstasy and my hand was being drenched in her sweet release.
I leaned against the door, unable to hold myself up any longer. Tara straightened her skirt, pushed her locks out of her eyes, and looked at me with what I knew to be tremendous desire.
"I have to get ready, why don't you take your clothes off and rest on the couch while I do. You're going to need it, I haven't even gotten started yet."
*
I sat there waiting for her to come out, excited and terrified of what was about to happen. It felt like an eternity before I heard the door open and she entered the room.
I was stunned. The red and black leather corset that barely contained her breasts was what I noticed first, I was rock hard in seconds. She had changed her skirt to a longer one matching the corset, made entirely of leather belts. She still had the same boots on, and by the time my eyes made it that far down her body, I was drooling.
"You will call me Miss Tara from now until I have finished. Calling me anything else will be painful for you. You will do exactly what I say, when I say it. Hesitation will be painful for you. You will not let yourself cum until I have finished. If you do, it will be painful for you. Are you ready, boy?"
Shocked by her appearance and what she was saying, I made my first mistake.
"Yes Tara." Instantly I realized what I had done wrong, but it was too late. That grin lit her face again, and she crossed the room to where I was sitting. Pointing to the belt at the top of her skirt she said, "Unfasten it with your teeth quickly, and I will forgive you this once."
I but down on the metal and tried to open it three times before she backhanded me so hard I fell off of the couch. Undoing the belt herself she said, "So much for forgiveness. Get back in your seat."
I righted myself on the couch just in time to see her skirt fall from her waist to the floor. I gasped as a massive purple strap-on popped out and hit my cheek. I knew she wanted me to suck it, but I was waiting for instruction this time. She put a hand around my throat and used the other to open my mouth. Still holding my throat, she spit on her other hand and started stroking her strap-on, pushing the other end in and out of herself.
"It's beautiful isn't it? Nothing like that filthy piece of meat sitting up like a pathetic puppy dog in your lap right now. You want to take the whole thing down your throat don't you? You want to feel every inch of me inside you. Say it."
"I want to take the whole thing down my throat. I want to feel every inch of you inside me, Miss Tara."
She backhanded me again, harder this time. My cheek was on fire.
"I didn't tell you to say my name. Pay attention, boy. Now, start sucking, and don't stop until you can get the whole thing down."
I held the huge purple cock in my hand, dripping with her saliva still, and started sucking. I got the first 4 inches down easily, but gagged a little when I tried to go further. I pulled back up to the head and started again, slowly working my way to the base. I got past 5 inches and looked up to see Tara's face. She was smiling wide, her hazel eyes seemingly on fire, and the moment I saw them, I had to get the rest down like she asked. I had to swallow her entire cock while we stared into each other. I gagged on the 7th inch and had to come up for air. I saw her eyes widen when my mouth left the head, and knew I'd made another mistake. She grabbed my chin, pointed my face up at hers, and spit on me.
"Until all 8 inches make it down your throat, you don't let it out of your mouth. Open wide!" I did as I was told, and she spit into my mouth this time.
"Swallow it." I did.
"Now let's try this again."
I took the head back in my mouth, and heard the click of a lighter as I went down the shaft. I looked up to see her exhale into my face. I had never seen anything so hot before, and I forced the last two inches into me, fighting the gag reflex, choking, barely keeping it down. I pulled back to the head and looked up for another exhale from her.
"Good boy! You're almost there!"
I got a sinking feeling as she pulled more of the other end out of herself, and gave me a look that said, 'Well what are you waiting for?'
I knew I had to find a way to take the 11" she had in front of me or that cigarette was getting put out on me, and I didn't like the thought of where she would do it.
I bobbed up and down on her cock, trying to relax my throat for the full length. I needed to see her exhale into my face again to make it to the hilt, so I stopped at 3" and looked up at her.
As if she had read my mind she teased in lilting syllables, "What is it boy? You need a little encouragement?" She held the cigarette less than an inch from her mouth and started to bite her lower lip. I started moving farther down her cock, slowly, and she finally drew a hit. I backed up to the head and drew my knees up onto the couch, angled my back to straighten out my throat. I looked up at her, and began sliding her entire length into my mouth. The last 2" hurt, a lot, in one of the best ways I've ever felt. I knew I couldn't hold it long, and I barely held back my climax when she exhaled in my face the second I got her cock down. Letting the cigarette dangle from her lips, she grabbed the back of my head and forced another inch of her cock into my throat from her pussy, spit in my face, then slowly removed her entire length from me, most of it returning to her tight crevice. She held the cigarette out for me to hit; she could tell I needed it.
"You're off to a good start, if you keep it up I might let you finish yourself off to the sight of me." Every word she said to me sounded sinister and seductive. The lust I felt for her was growing exponentially by the minute. I knew I couldn't take control of the situation, but I was certain she would enjoy it if I begged.
"Miss Tara, will you please fuck me? Please? I want to feel you bucking in and out of me, I want to feel the power of the thrusts as you climax. Please, Miss Tara?"
She saw right through it, was aware that I was trying to find a way to steer our little escapade.
But I had followed the rules, and she rewarded me for it
"Of course I will, little boy, what else could you possibly be good for?"
She smiled, leaning down to kiss me. The kiss broke quickly, as she grabbed me by the throat with one hand and my balls with the other, roughly forcing me onto the floor on all fours. I was grateful for the deepthroating treatment now, because without warning, she got on her knees behind me and thrust 4" in. If I hadn't gagged and spit so much, her dry cock would have ripped me. I cried out in pleasure and pain, my asshole feeling so full, knowing she had so much more to fit into me. I screamed and moaned with every thrust, finding it harder and harder to remember that her cock wasn't infinite in size. She kept putting more of it into me, until I stopped crying out because I was out of breath. She made one more thrust, keeping her thighs pressed against my ass instead of pulling back this time. My cock was throbbing, and bigger than I'd ever seen it before. I wanted to relieve myself so badly it felt impossible to resist.
I heard a click of some kind from behind me, and without pulling her thighs back I felt more of her enter me, it was unbearably orgasmic, feeling so full of her. Then I felt her thighs withdraw, but the fullness of her cock stayed. I heard her boots on the floor as she walked around in front of me. The strap-on was no longer attached, she had left it inside of me.
"I didn't feel like cumming yet. I'm going to have another smoke while you wait. Enjoy it, this is what you wanted. You wanted to be with me, and this is what that means." She lit her cigarette and knelt down to face me.
"When I start again, you will use that pathetic body of yours to make me cum. You will do the work, or I will have to find a more degrading way for you to get me there. Do you understand?"
"Yes, Miss Tara. I understand."
She kissed me deeply and passionately, and the fullness of her cock brought me to the edge. Thankfully she stopped in time.
"Then I think you're ready."
She spit in my face again, and the impact of it almost triggered my orgasm. She exhaled at me and sat the cigarette in the ashtray.
"You have until that goes out to work that ass and make me cum."
She knelt behind me, yanked more than half of her cock back out, and hooked it back into her harness. I could hear it sliding into her, she was dripping wet. I was determined to make her cum, and I knew just what to do.
She started thrusting into me hard and fast, more forceful than anything she had done yet. I waited for her to put herself deep into me, and clenched myself around her cock as hard as I could. She couldn't draw anymore of her cock back out of me. She began pumping and pounding me furiously, bringing almost all of the length of her in and out of her gloriously tight little box. I felt her start to shake and began thrusting back at her while she shuddered in the throes of a massive orgasm, moaning at the top of her lungs. I didn't stop bucking against her until she pulled out of me, collapsing against the couch behind us, out of breath and obviously satisfied. I turned around to check the ashtray and the cigarette was still burning. I picked it up and brought it to her. "You did much better than I would have expected. Being a good sub isn't a skill many people pick up so quickly. You didn't even touch yourself or blow your load. I'm impressed."
She hit the cigarette and passed it to me.
"I think it's very important in a Dom/sub relationship, for the Dom to make sure to bring the sub back to a safe state of mind afterward, and not to let them become confused about their value. You are not worthless, that talk is just for the act. That's why I didn't want you to cum, I would like to bring you back to baseline."
I handed the cigarette back to her, and she took a long draw, then blew it in my face again.
"Would you like to cum in my mouth, baby? Would you like me to take you down my throat? I think you've earned it."
"Yes, Miss Tara, I would love that."
She put the cigarette out and crawled on top of me, kissing me with furious passion, quickly working her mouth down my body, stopping just before my cock to lock eyes with me as she took my entire length down effortlessly. Cupping my balls, never breaking eye contact, she moved her mouth up and down my full shaft rhythmically and sensually, and I knew I wasn't going to last much longer.
"I'm gonna cum, Miss Tara, I'm gonna cum."
She quickly took all of me into her mouth, and let every rope of cum shoot straight down her throat, not coming back up until I was shaking bodily from the over-stimulation of her tongue working around me.
She smiled as she climbed up to kiss me.
She nestled against me, and we lay there entwined until morning.
We never spoke of that night again, which has made it so much more magical to me.
Barbie
- 26.02.2021
- 20
- 0
- Category:
- BDSM
