Janey

Janey told me to undress and I hurriedly obeyed until I saw that she was making no effort to undress herself. I hesitated but proceeded anyways under her mindful stare. She told me to stand before her once I was naked. She stared and fondled my cock within its frame.

"Does it hurt now?"

"Yes."

"Did you wear it last night?"

"Yes... I mean I took it off a few times to practice putting it on like you said but wore it the rest of the night."

"Did it hurt last night?"

"Yes."

"But you kept it on?"

"Yes."

"Kneel."

I did so.

"I like that you kept it on. It's sexy that you subordinate yourself to me and I love how excited you get pleasing me."

I blushed. Part of me wanted to argue. To point out that as a man and the older partner I should be in charge but the words didn't come out. I didn't really believe it or even want it and given that I was kneeling naked before her the words would have been surreal. To make her point, she reached down with her hand and then brought it to my lips. Her fingers were covered in my precum. She started to put her fingers in my mouth but I resisted by closing my mouth and turning my head.

"No... please. I... I... can't."

"It's OK baby. You'll get there. I like that you asked for permission to take your cage off -- it shows you think of me as an authority figure. You'll never meet anyone like me again and you already know it. Don't mistake me being someone to indulge your fantasies or who will put your desires before mine. If you want to be with me, you will always seek to please me and find your joy in doing so."

Her words were enticing and frightening. I felt myself sinking into her. She offered me her fingers again but I still couldn't do that. Janey seemed understanding and allowed me to take the cage off. She spread her legs and I moaned in gratitude to be allowed to bury my mouth in between her long legs.

After she was sated, she brought me into her bedroom. She pulled out silk scarves and tied my arms to the headboard. She poured oil on my cock and started rubbing me.

"I wanted to fuck tonight but I'm so sore from last night. He's big -- bigger than you."

I knew it was far too early for me to expect her to be exclusive with me. Moreso, Janey had the je ne sais quoi of a woman that easily juggled lovers. However, the boldness of her words lit my jealousy.

"You're lying right where he fucked me."

My cock continued to betray me as it spasmed in her hand. She expertly varied the pace and pressure keeping me just on the verge of orgasm but never getting there.

"Imagine if the world knew that Mr. bigshot partner esquire had his cock caged up last night and got all hot and bothered thinking of me with another man."

I groaned over and over as she kept stroking me and whispering in my ear, "I got off so many times thinking about you waiting for me all caged up. I came so hard and so many times."

My mouth was dry and I could feel the red in my cheeks. I desperately wanted not to climax while she was talking about another man but I hit the point of inevitability when suddenly Janey let go of my cock. It spasmed several times but I never came. My balls felt like they were about to explode.

"Please..." I begged.

"You're so pathetic."

I couldn't believe I was letting her treat me this way. My mind was in a fog and my protests stuck in my throat. I felt pathetic and humiliated but I'd never been so enraptured in my life.

She grabbed my balls and squeezed to the perfect intersection of pain and pleasure.

"Please... I... I'll do... I'll do anything..." I whispered.

Janey rubbed the head of my cock and brought her fingers to my lips. I tightened my lips and pleaded 'no' with my eyes.

"I thought you said 'anything'."

She had me and I nervously stuck out my tongue and licked. She stroked me further and again offered me more of myself. This time I sucked her fingers greedily as she fed me my precum. It was salty and the texture thicker than I expected. I gagged. At first from the taste and then from her finger hitting the back of my throat.

"I bet you prefer girls that swallow, don't you?"

"Yes."

"Now you're one of them, aren't you baby? You're a cum swallower."

I could feel my cheeks flush further. I felt so below her. Suddenly, I had an intense desire to debase myself further.

"Can I... may I lick you... back there."

"You're an enthusiastic ass licker and pussy licker... show me that sexy tongue of yours."

I stuck my tongue out and she fed me more precum.

"You're such a pussy with a pathetic little cock and now you swallow!"

She laughed derisively. "I do love that sexy little mouth of yours baby."

I asked again, "can I lick your asshole?"

"Soon baby, but first close your eyes and tell me what you imagined last night."

Janey stroked my cock painfully slowly as I recounted how I felt the night before. My jealousy and humiliation and profound excitement from feeling like I had wettened her for another man, I admitted that I had suffered in pain as my cock spasmed imagining she was being fucked by him. She prodded me to admit I'd imagined him to have a bigger cock than my own. I volunteered that I thought of him fucking her earlier that night as I worshiped her pussy and that had mindfucked me.

She giggled, "you're such a pussy... aren't you?"

I didn't reply.

She kept bringing me to the brink of orgasm and then stopping. I felt like I was going to explode if I didn't come soon.

"Please..." I begged, "I'll lick your ass... I'll lick your pussy..."

"You'll do that regardless," Janey giggled. "Beg me to put the cage back on. Beg not to cum."

I couldn't. Every cell in my body needed release.

"Please let me cum... I'll do anything!"

"Awwwwww, do you want to cum baby?"

"So badly. I need it."

"Tell me you have a little cock."

I hated it when she played that game but I knew resistance would be futile.

"I have a little cock. Please let my little cock cum."

"I want you to not want to cum. I want you to beg me not to cum. Your little cock is too small to cum."

"Please let me cum... I'll... I'll do... do anything!"

"Then do as you're told."

I remembered her words from the club and began to regain my composure. She was stroking me faster and I was near the point of no return. My mind raced. I felt like I couldn't possibly forego orgasm. Janey had invaded my psyche though. I felt out of body as the words came out of my mouth.

"Please... stop... please stop... please put me back in..."

I couldn't believe I was saying it. Janey grinned broadly at my submission.

She kept stroking me. I was struggling NOT to cum.

"Please Janey. Please stop. I don't want to... cum... I don't want to cum."

She slowed her stroking, "tell me to put your little cock back in it's little cage."

As always my anger briefly flared at "little cock". She'd already won the game and now she was rubbing it in but I swallowed my pride.

"Please put my little cock back in it's little cage."

Janey gasped in excitement and I could feel her wetness running onto my leg.

"You want me to put your tiny little cock back in it's tiny little cage?"

"Yes." I was defeated.

"But you were so close! And now I'm going to cage you for so long...."

Janey squeezed my balls tight and I whimpered in submission.

Janey grabbed the cage and squeezed my well lubed cock back into it. She used my mouth over and over that night. My neck and tongue were aching from her riding my face. My lips were numb and my face coated in her juices. My nose drowned in her fragrance. My balls ached and my cock seared as it fought to escape its confines. I knew I was permanently imprinted.

After that night we spent a lot of time together, meeting nearly every night. We began to meet each other's friends and outwardly were a typical couple. Underneath the veneer I was often in chastity. Janey was demanding but never haughty. She made her expectations clear and held me accountable for meeting them. With a wink of her eye I would drop to my knees. I knew, my tongue knew, every nanometer of her pussy and ass.

After three months together I had yet to fuck her. That fact drove me crazy. She loved teasing me and after she was done with my mouth she would often stroke my cock. At times I begged not to cum to please her but occasionally she brought me to release. I learned well the agony of a ruined orgasm. She would stroke me to the point of no return and then stop. The orgasm that followed afterwards was painful and unsatisfying. Sometimes she would tease that if I begged her to feed me my cum she might be less likely to ruin my orgasm but I just couldn't do it. Janey had gotten me used to licking my precum off her fingers but I couldn't go further. After an orgasm, even a ruined one, my head space was different and I just couldn't take my own load.

As we grew closer, Janey told me stories of her sexual development. She grew up in Palos Verdes with four older brothers so she understood the male intellect instinctively. As a sophomore in high school she had caught one of her brother's friends trying on a pair of her panties. It had intrigued her and they began to date. Janey discovered the eroticism of humiliation as she made her boyfriend model for her.

In college she had several vanilla relationships that all eventually bored her. She experimented with women a bit and found it easier to express her natural dominance with them. She took a graduate seminar her senior year on the psychology of sexuality that broadened her knowledge and led to a brief but explosive relationship with the professor of the class.

In law school, Janey became involved with the married Dean of the university. It was her first true Ds relationship. He was a sadist and dominated her roughly. He would whip her often and Janey prided herself on never flinching or crying out. She learned she could take a beating easily. Being used sexually was exciting for her at first. The masked sex parties where he would watch her debase herself with men and women gradually became less enthralling. Additionally, her enchantment with the Dean turned to disappointment as she saw his continued dishonesty with his family.

The Dean became despondent after Janey ended things. He divorced and re-approached her a year later at which point the affair reignited but with the roles reversed. Janey loved humiliating him for sobbing in pain after taking beatings far less severe than Janey had endured noiselessly. She loved going back to the same sex parties, with him on the other end of the leash and watching him debase himself as she had done before. She discovered her passion for chastity and kept him locked up virtually always. She would take him out occasionally and stroke his cock to the edge of orgasm over and over. She rarely let him orgasm and one day told him frankly that she would leave him if he ever orgasmed again. She loved the new dynamic this created. As she stroked him she would tell him his tiny cock was useless and paint imagery of him fluffing future lovers and cleaning her up after. Instead of begging to orgasm, the Dean had to beg not to cum and for Janey to lock him up again as he feared losing her more than anything. The Dean finally orgasmed after 17 consecutive weeks in chastity. He had been so excited that he came as soon as the cage was removed. Janey didn't even touch him. Janey fed him his cum as she said goodbye. He sobbed but never tried to contact her again.

Her stories fascinated me and scared me. I read more about Ds and chastity. For her 28th birthday I bought her a custom lock with a beautiful gold key on a matching gold chain. She loved the gift and when we came back to my place we fucked her for the first time. She teased me as was our custom but then surprised me by straddling me. The image of her looking down and grabbing my cock as I entered her was seared into my cortex. It was sublime being inside of her and I struggled to maintain control as she taunted me with my cage being locked from now on. It was so hot. We fucked animalistically and for the first time ever it felt like I was in control of Janey. I came explosively and within moments was ready for more. We fucked three times before I collapsed on sheets covered in our sweat and cum. I closed my eyes for a moment and drifted into a dream state.

I woke up to Janey kneeling over my chest. She smelled of sex.

"I need to go baby."

"Where are you going?"

"Late night bday celebration with friends."

I was hurt I wasn't invited but she needed freedom and I knew better than to become resentful.

"Will you kiss me goodbye?"

I tried to sit up to kiss her but fell short with her sitting on my chest. I expected her to lean down to meet me but instead she moved forward so that her pussy was directly above my face. It was still beautiful but red rather than pink. Her clit and labia were swollen. Her entrance open wide with my cum and hers dripping out.

"Kiss me."

It was no longer a question. I rapidly felt whatever small momentum I had just gained receding. I knew I could say no. Drinking my seed directly from her well fucked pussy seemed beyond the pale but I had developed a real need to please Janey. I looked up into Janey's eyes as our juices began to drip on my face. Janey used a finger to wipe up some of my cum that had landed on my cheek. I opened my mouth and she put her finger in.

"Kiss me."

I lifted my head and kissed her clit passionately. Janey moaned in delight. She sat forward and began grinding her pussy on my face. I could taste her and myself. I followed her directive to put my tongue inside of her. She grabbed the headboard for leverage, stared intently down on me and ground her clit on my nose. She was dripping streams of excitement as well as my recent orgasms and I found myself struggling to both breathe and swallow. She taunted me as I swallowed everything she gave me. A large glob of my cum fell into my mouth and Janey laughed as I gagged while swallowing it. She made it clear that if and when we ever fucked again I would enthusiastically clean her up. She laughed again as she moved forward and my cum got into my eyes. It burned and I was blinded. Her words rang in my ears, "you really are a dirty cum swallowing slut."

She rode my face roughly. She came once but kept going and had two more orgasms before she caged me, locked me up, and left. Being locked for the first time had a powerful psychological impact.

She came over late that night. She was tipsy and in a great mood. She thanked me again for the lock and key and said it made her ecstatic to know I was locked for her. However, her next words floored me. She was flying to Rome the next day for work. She felt the short break would be good for me so that I could become accustomed to being locked up and obeying her even in her absence.

We'd never talked of monogamy. She never brought it up and I never asked but I felt empty even prior to her absence. The words spilled out, "are you going to Rome with anyone? Are you meeting anyone? Are you fucking anyone?" I felt dumb but also relieved. She leaned in and held me. There was a long pause before she spoke. I was worried she would be annoyed but there was kindness in her voice.

"I'm not baby. I'm going on my own. I have friends in Rome -- lovers even but... I haven't slept with anyone but you in months. It's good we're talking about this."

I was relieved and hugged her tight. "I'll be ok... I mean if... it would be hard but I want you to be happy." I couldn't believe I had just said it.

Janey kissed me. She smiled.

"You're sweet. It could be fun. Imagine sitting at a bar watching me on a date with someone hotter than you."

"Good luck finding him!" I joked.

Janey laughed.

"You would go to Kiki and pick out the lingerie you think he'd like. You would book the dinner and the hotel suite -- rose petals on the bed. You'd make it so romantic and sexy for us while your little cock is all locked up. You would come to me and imagine his big cock in me after you licked me before I went to meet him. You'd be up all night thinking of us fucking. After he left I might even have you lick me clean..."

I groaned. In excitement, in horror, in disbelief. My cock was straining to get out and my cheeks flushed.

"Someday baby, but not this trip. I'll know when you're ready."

I missed Janey tons but we talked frequently. I thought of her cucking me often and couldn't decide if I was more excited or horrified by the thought. She started telling me fantasies she had of me watching her with another man during our long phone calls. I would be aching in my cage as I watched her get herself off on facetime while imaging someone else fucking her.

I planned an extravagant evening for her return. We went back to D'Amico's and had an amazing time. She kept hinting that she had a surprise for me. It had me on edge given everything we'd been talking about but I was so happy to have her back.

We grabbed a drink at the King Cole bar after dinner. We were chatting and joking when Janey caught me off guard.

"Are you a virgin?"

"Huh? No." I was confused. Forty year old virgins don't really exist.

"I mean in your ass. Are you a virgin?"

"Oh! Yes, I guess.... A tongue or finger here and there."

"No cocks? No high school experimentation?" She teased.

"No."

"No trips to your local dominatrix?"

I laughed, "No, never done that."

Janey's eyes lit up. She grabbed the bartender's attention and ordered us two martinis.

"Drink up STUUUUD because your little cherry is getting popped tonight!"

I coughed up my drink and nearly sprayed it all over her.

"What?"

Janey adopted a masculine voice, "I'm going to fuck you, you dirty little slut. I'm going to pound you until your eyes roll up in the back of your head. This is going to be a fucking prison movie."

Janey laughed. She couldn't keep the voice going.

I thought she was joking but when she threw money on the bar and grabbed my hand excitedly I knew definitively I was about to be sodomized.

We got in a car and Janey started kissing me. She was hot and managed to undo my belt with one hand. Her other hand was in my mouth.

I sucked on her fingers as Janey cooed, "get them wet baby."

I could tell the driver was trying to figure out what was going on as Janey pushed her hand into my pants. She miraculously somehow arrived in my neverland and roughly shoved a finger in me.

I winced as another finger entered me.

We arrived before a third finger could join the effort.

We raced out of the elevator and Janey ordered me to strip as soon as we got inside. Janey led me to a full length mirror and stood me in front of it. She left the room and when she came back she was wearing a harness and strap on. It looked menacingly large. She told me to grab the mirror with my hands and arch my back so that my ass stuck out. She spread my legs with her knees and traced my body with a finger as we stared intently into each other's eyes through the mirror.

Janey got in place behind me and laughed as I looked over my shoulder and said, "be gentle."

She slapped me hard on my ass and said, "deep breath and relax." I groaned as she entered me. It hurt at first but became less painful and I found my erection returning as I marvelled at the depravity of Janey sodomizing me in the mirror. Janey leaned into me and grabbed my balls for leverage as she started thrusting into me harder and faster. Her motion moved me steadily forward and soon I was essentially flush with the mirror. Momentarily my mind wandered to the women I'd fucked and the triggers that most excited me. I wanted so badly to please Janey. I gave up any sense of my dignity and submitted fully.

"Fuck Janey, your cock is so big!!! You own my ass... Oh fuck Daddy..."