Lily's Wish

Janey teased me further about swallowing my own cum while on my knees outdoors late at night like a dirty hooker. I let out a groan as my cock throbbed thinking about what happened in that warehouse doorway. I remembered looking up at her from my knees and tasting my own cum as her hand violated my mouth. I remembered gagging on her fingers as they hit the back of my throat. I could feel myself leaking, hopelessly intoxicated by her words.

As we headed back to our room Janey teased me relentlessly. In the elevator she took my belt off of me and wrapped it around my neck like a leash. A young couple stared, mouths agape, at us until they got off on their floor.

The woman said, "Have fun!" as they left and I could hear their laughter until the doors closed.

Janey led me by the leash back into our room, Janey told me to disrobe and wait for her on my knees. A few minutes later she approached me from behind and warned me she was going to take away whatever remained of my manhood. She pulled my head back roughly and I found myself looking straight up at her strap-on. She looked down at me and smirked as she warned that she was going to make me a dirty cocksucker. She came around to face me and told me to lick the cock slowly while looking up at her. I leaned forward and did so. My cock spasmed as I debased myself once again.

"God, you're pathetic. You love this." She grabbed my ears and directed me until I'd navigated her cock entirely with my tongue.

"Open up cuckie."

I placed my lips over the tip and slowly took the head into my mouth.

"Suck my cock, cuckie"

She wrapped her fingers in my hair and eased her dildo all the way down my throat. I choked and gagged but she didn't let up. She would take it out to let me catch my breath but would then shove it back in. She was rough with me. I felt the back of my throat bruising.

"Keep looking up at me."

My eyes watered. My face was covered in my own drool. Janey warned not to bite her cock or I'd be sucking a real one. She told me we would keep going until I had taken her whole cock in my throat. She kept pushing me. It felt like hours but I finally got her cock in the back of my throat without gagging for long enough to sate her desire.

Satisfied, she told me to get up on the bed on my back.

"Spread your legs and hold your knees to your chest."

She approached the bed stroking her cock, "I love how scared you look."

I felt utterly humiliated but at the same time had never desired anything more in life than surrendering my dignity to Janey at that moment.

She settled on the bed in between my legs, "I see your fear; wondering how hard I'm going to fuck you and worried that I will think less of you... I will, I will think less of you but you still can't and won't stop me."

I grimaced and moaned as she began to enter me. She kept taunting me, "Look at your ass, taking my cock. Swallowing it inch by inch."

My virgin asshole was tight, but she showed no mercy. She never hesitated and her constant pressure forced her past my sphincter. I felt lightheaded and a cold sweat covered me. I gritted my teeth and my jaw bulged. I let out the most pathetic moan.

"I'm going to fuck you so hard. I'm going to show you how real men fuck."

I felt powerless in a way I had never felt before. Janey fed off my emotions, my pathetic "ouches", and my involuntary moans. She loved it. I could feel her power.

She pulled her cock the way out of me and then slammed it back into my ass. She kept on until her sweat was dripping onto me. She put my legs over her shoulders and somehow found a higher gear -- ramming into me harder and faster. As she fucked me, she warned, "someday you will have to take a real cock."

She grinned as she saw fear and acceptance in my eyes.

"You look so weak and pathetic being ass fucked cuckie." She continued to slam into me. She was nearing orgasm but it felt as though she couldn't quite get over the top. My pain was unbearable but slowly it subsided and my moans slipped into a mix of pain and pleasure.

She pulled out suddenly and I felt strangely empty. She ripped off the dildo and jumped onto my face. She ground her soaked cunt on my face and had several violent orgasms in quick succession. Once sated, she collapsed off of me. I couldn't move. I was sore and my masculinity was gone.

...

Over the next several months my fate as Janey's cuckold solidified. We spent time together socially and to the world we appeared to be good friends. The truth was I was always in chastity and was faithful to Janey whereas she maintained several lovers. Janey and I never fucked but she used my mouth often for pleasure. She enjoyed using her strap-on to violate my mouth and ass. I rarely orgasmed - when I did it was at her command and often with my tongue in her ass or her dildo in mine.

Janey loved teasing me about how I had to do all the 'work' of a boyfriend; taking her out to dinner, shows, listening and offering support but I never got the payoff. I never got to fuck her. After our dates I would often walk her to a lover's home where she would remind me I was her cuckie rather than her lover because I was too small for her.

Janey was dominant over all of her lovers. She kept all in chastity because it was a constant physical reminder of her superiority and also gave her control of the most defining aspect of manhood. Janey also had submissives that served her but with whom she was not sexually active. She was fiercely honest and didn't hide anything from her lovers or submissives. Her psychological control of people was incredible. I was devoted to her even though I struggled at times being treated as inferior to her lovers. My jealousy was always just below the surface but I also recognized that I felt peace serving her and her ability to humiliate me in a way that I found sexually exciting was profound. I craved it.

...

Janey had a secluded summer home on Montauk with a pool and beautiful ocean views. I was ecstatic when she invited me to spend the weekend with her. She typically reserved those weekends for one of her two primary lovers, Tony, a bigshot lawyer in NYC or Alejandro, an accomplished artist who spent most of his time in Europe but visited often. We drove out together on a beautiful Friday morning. We spent a few hours by the ocean sipping caipirinhas. Once back at her place I showered and she had me lay on the bed and quickly bound my wrists to my ankles. Janey removed my cage and placed a blindfold. I could still make out vague shapes with the blindfold on but not more than that.

"Don't go anywhere cuckie - I'll be back."

I heard her in the shower and then the clicking of her heels as she left. The clicking disappeared and I realized she had left. I tested my binds and found them secure. I must have dozed off as I woke up disoriented with my erect cock enjoying its rare freedom.

Hours later I heard a door open and the clicking of her heels again. She came up to the bedroom. I imagined her wearing a tight summer dress cut so low that her firm taut breasts constantly threatened to spill out.

Janey spoke, "I went back into town to treat myself to a few things. It's hot out there now. Much hotter than earlier. I'm sweaty, cuckie."

I felt something light drop on my face. The sweet smell could only have come from Janey's hot pussy. I inhaled obscenely.

"Did you miss me?"

"Yes."

"What did you think of during my absence?"

I decided to be truthful, aware it might lead things in the wrong direction.

"I dreamed of fucking you."

She laughed, "The ocean air is going to your head."

"Please, I'll do anything."

"I know." Her fingers lightly traced my chest towards my crotch. I raised my pelvis in order to get my throbbing cock into her hand. I groaned pitifully as her hand skipped my cock to trace my inner thighs. Her hand came back up to my nipples. I moaned as she pinched them.

My voice was desperate, "please let me fuck you."

She whispered in my ear, "Maybe? I am so horny. You can smell it in my panties." She gently bit my ear.

My heart leapt even as I told myself she was fucking with me.

"I wish Alejandro was here. He has such a great cock. He's gorgeous too. I would love to fuck him while you watched."

She moved on top of me; I gasped as I felt her soft wet cunt insanely near my cock. I strained against my binds to no avail. I lifted my ass again but she deftly avoided my lance.

"So close. Your little cock is so close to my tight pussy. If you were bigger you'd be in me."

"Aaaargh!!" It was too much. My body was shaking.

She moved up on my chest and tossed the panties aside. The fragrance of her arousal grew stronger. She was just out of my tongue's reach even as I strained my neck. She put her finger in my mouth. It was covered in her nectar. My cock strained. Her fingers hit the back of my throat and I was able to keep them there without gagging.

"Good cuckie. You're going to be such a good cocksucker. It makes me so wet when you deep throat my cock, my fingers... I think you're ready for a real cock."

I felt scared. Mostly because I knew I would obey her if push came to shove.

"Fuck, just the thought of it makes me soooo wet... see?" She shifted herself and my mouth was suddenly covered by her pussy. I opened up and put my tongue in her. Her fingers ran through my hair and held my head firmly in place as she used my mouth and face for her pleasure.

"Oh cuckie, if you ever went bald I'd have to get rid of you. I love having fistfuls of your hair in my hands as I ride your cute face. I love how pathetically excited you get licking my pussy and swallowing my cum."

Her words were almost enough to make my cock erupt but just before the moment when I might have been powerless to maintain my composure the bed shifted. I yelled into Janey's pussy as I felt someone climb up my body and spread Janey's legs apart. Janey shifted back a bit so my tongue was on her clit. Her moans became screams, frantic and uncontrolled. I realized someone was fucking her. I couldn't see beyond Janey though with the blindfold on and her body towering over me.

I could feel hips colliding and imagined a cock deep in Janey's pussy. To my chagrin, my cock remained rock hard. I focused on Janey's clit, alternately licking it and then sucking it. It swelled with her excitement and felt like a tiny cock in my mouth. I could sense from their movements that his cock was big and long.

"He's fucking me so good, cuckie... oh, fuck."

Janey removed the blindfold. The room was dark but I could make out broad shoulders behind her. Her firm breasts bounced and she repeated a loud, "fuck!" with every thrust. I looked down and was shocked by the size of the cock penetrating Janey as well as how disturbingly close it was to my tongue.

"Tell him to fuck me harder."

I felt mindfucked as I directed the stranger. My voice was partially muffled by Janey's pussy but nevertheless, the stranger reacted to my words by bucking harder.

"Fuck her. Fuck her harder. Fuck her tight pussy with that monster cock."

Janey squealed in delight. She was nearing climax.

"Fuck her tight cunt. Make her cum on your big cock."

"Oh God, he's so big cuckie. So much bigger than you..."

The stranger remained silent other than his breathing which was becoming heavier and ragged. I feared his climax might be nearing as well.

She was leaking all over my chin and neck. Her climax began to ramp up. "Jesus fucking Christ!" Janey's grip on my hair tightened to the point I was certain she was ripping it out.

I strained to keep her clit in my mouth. I hoped Janey wouldn't make me egg him on further. My eyes had adjusted to the dark by now and I could see Janey's eyes in the back of her head and the stranger's huge cock pumping in and out of her cunt.

She screamed, "oh God, oh God, oh God, oh God, oh God, oh God..." as she hit nirvana. I felt her body collapse. She whimpered as he ripped into her like a man possessed. His pounding pushed her forward until her pussy was right above my eyes, allowing me the perfect vantage point to see his scrotum spasm. He violated his vow of silence with a deafening, "aaaargh!!" I felt nauseous and closed my eyes as the inevitable began to happen with their fluids leaking onto my eyes and nose. He removed his cock from Janey with a loud 'plop' and a large load landed on my mouth. I kept my lips tightly closed. My eyes were stinging and my vision blurry as I felt him leave the bed and then the front door close. I was alone with Janey again.

Janey undid my binds and grabbed my cock as she straddled me. She impaled herself on me without teasing. She sat straight up and remained still. I couldn't believe I was inside her after all this time. I nearly erupted. She leaned forward. I could feel her nipples stabbing my chest, "Alejandro's cum tastes so good." She licked my face and then brought her lips to mine. I let out a weak, "no" as her tongue easily passed my lips and fed me.

"I love it from a big cock. It tastes better."

She took another big lick and fed me more of Alejandro. In spite of Janey's pounding with a massive cock, her pussy was tight and enveloped my cock. She fucked me as she continued to feed me another man's cum with her mouth and fingers. I pinched her nipples and put a fingertip in her asshole. The way she was grinding herself onto me allowed her to achieve multiple small orgasms whereas I remained on the precipice but unable to get to the zenith. I grabbed her hips to create the leverage I needed but she told me to keep my hands over my heads and then grabbed my wrists to keep them there.

"Do you feel his cum on your little cock? He made me cum so hard. I thought how pathetic you must feel watching us... tasting us... it put me over the top."

I moaned in frustration.

Her mischievous smile came back, "don't you want to cum cuckie? You've been such a pathetically obedient cuck - you deserve it."

I moaned again.

"You can fuck me to your heart's content this weekend! I'm going to show pity to your tiny cock."

"Please!" I bit her nipple the way she liked.

"But..."

"Fuck... there's always a 'but.'"

"Once you cum you go back in your cage."

"Oh God... no."

"And for every time we fuck, your cage stays on for a day... no, a week..., no, a month! Yes, you'll be locked one month for every time we fuck this weekend but only if you cum!"

It was so fucking cruel. My head spun. I couldn't help but laugh, "God, you're a sadistic bitch."

She laughed, "I know."

"I love it."

"I know."

"I'd do anything for you."

"I know."

"I love you."

"I know."