Lily's Wish

"Awwwwww, cuckie. You're adorable." She put her hands on my cheeks and leaned into me looking right in my eyes.

"Did you buy yourself another pair of panties today?"

"Yes." I said sheepishly.

Janey laughed out loud, "You know she works on commission?"

I gave an embarrassed smile.

"Well let me see!"

I drowned in self-loathing and sexual fervor as I undressed in order to humiliate myself.

Janey kept laughing as she took me into the bedroom, "You really are a pussy, aren't you?"

She told me to get on the bed and came back with lotion from the bathroom. She cuddled up next to me and handed me her phone.

"These are from today." She showed me a number of pics and short videos of her being licked and fucked.

I couldn't control myself from getting hard which she noticed right away and instantly began teasing me.

I was watching another video of them and finally asked, "Your boyfriend?"

"Oh God no. An amusement. You got me so wet. I thought of you while we fucked. I even told Bobby I preferred you *but* with *his* magnificent cock. He fucked me so good today. He's so big and his cock turns up just perfectly. He got so cocky though that I didn't let him cum! He was in tears when I locked him back up."

Janey put lotion in her hand and began to stroke me. "You thought he came in me when you got on your knees, didn't you?"

I could only moan as her hand and my humiliation quickly brought me to the brink of orgasm.

"You did, you're going to be fun my little cuckie."

"Oh God!" I came hard all over my belly and her hand but she kept stroking my now overly sensitive cock. I instinctively moved my hand to push her away but she warned me not to dare. The next several minutes were torture as I forced myself to submit to her ministrations. All throughout she whispered in my ear how I was too small for a beautiful woman like her, that I was destined to be locked up for her. I came a second time when she told me that she was going to use my mouth and ass however she saw fit but my worthless cock would always be locked unless she wanted to show it off to her boyfriends to embarrass me. She continued to stroke me through orgasms three and four. I couldn't take anymore and finally begged her to lock me up at which point she laughed uproariously and stopped subbing my cock.

"Yay!"

A few minutes later my cock was ensconced in its new cage. It was a tight fit and Janey admitted, "You know you're bigger than I expected but you're still too small and pathetic to be more than my cuckie." Janey tweaked my nipples causing me to grimace as my cock tried to swell in its new confines.

The cage had a built-in locking mechanism; Janey showed me her key and how she could open and close it. I hated viewing myself as a cuckold -- I had always done well with women albeit not of Janey's caliber. However, it was comforting feeling connected to Janey in a physical manner after all that had happened. I had a million questions and was about to blurt them out when she touched herself and moaned, "I swear I have the libido of a 19 year old boy"

She kissed me, got up, and walked out with a "see you next week!"

...

The next week was torture. Janey would text me often with lurid details of her frequent dalliances. Just the beginning of an erection was horribly painful. I was constantly horny but could not release no matter how much I fiddled with my cage. I had to pee sitting down further cementing my emasculation. I formulated a million ultimatums that I would give Janey for us to have a 'normal' relationship but deep down I knew they were all futile. I wanted desperately to fuck her and taste her.

As part of an effort to create the 'normal' relationship, I went to some trouble to get box seats for the Knicks against the Lakers. Janey wasn't a sports aficionado but it was a big game and the glitterati would be out in full force. I was disappointed when Janey declined my invitation as she had already been invited by another friend and they were sitting court-side. My jealousy sprang into action and I started asking probing questions about who her escort was. Janey parried my interrogation deftly and advised me to take Colette, suggesting if I did so, we could all meet up after the game.

Her invitation partially assuaged my bruised ego and the next day I called Colette at the boutique. She wasn't working that day and I had to leave a message. I called again the following day after receiving no response. This time Colette picked up but said it was busy and to drop in at 8:00. The game started at 8:00 so I tried to handle matters over the phone as getting there would be a huge inconvenience but Colette gave a terse "goodbye" and hung up. I called back but Colette wouldn't talk and I resigned myself to missing the first quarter.

I arrived at the appointed hour to find her closing up. Colette was beautiful. She had dark features with startling light green eyes. She was petite with a bosom appropriate for her frame. Her pouty lips were colored a dark red and I couldn't help but imagine them around my cock; this reverie resulted in a sharp pain in my groin. She was young. I guessed early 20's and seemed naive but I had an inkling she was worldlier than she let on.

"Come to the back."

I was in a hurry and reluctant to waste time in the back. I blurted out the invitation to the game and potentially meeting up with Janey in an adolescent manner. She neither accepted nor declined.

"Will you come to the back?"

She didn't wait for an answer and I followed her meekly. Once in the back, Colette turned to me, "I loved the piece you bought me! Will you get me another? Please!?!?"

Her enthusiasm was charming and I couldn't help but smile as I agreed.

"Thank you!" She jumped up, hugged me, and kissed me on the cheek.

I sat on a leather bench on her direction.

"Which do you like better?"

Colette proceeded to undress and modelled a negligee for me. Her derriere was perfectly heart shaped and I grimaced as she pirouetted slowly to afford me a view of her barely covered ass. The second outfit she tried on was a white open gusset thong and white leather straps that wrapped around her chest without covering her modest but firm breasts. The white contrasted her skin tone and created an angelic mood whereas the leather straps created a bondage feel. She pulled up a chair and sat in front of me with her legs spread wide and nary a trace of modesty. My gaze was fixed on her lewdly displayed cunt. She had a thin line of hair above her pubis. Her labia were so small as to be barely visible. I had an insatiable desire to taste her and found myself on my knees.

I let out an audible groan as Colette crossed her legs, "you like?"

My mouth was so dry I could barely talk. I let out a weak, "love."

"You'll get them for me?"

"Of course."

"Yay, you're the best!"

She instructed me to turn around on my knees and put my chest on the bench with my hands behind my back. I did not protest as she pulled my trousers to my ankles. I felt certain this was all Janey's machinations. The wall behind the bench was mirrored affording me a perfect view of Colette as she gripped my balls and steadily increased the pressure until I begged her to stop. She stopped and lightly traced my ass and outer thighs. She spread my cheeks and I felt her saliva drip onto my asshole. It felt ominous as it landed and then drifted slowly down my scrotum. Colette repeated this cycle several times, ramping up the pressure on my testicles iteratively.

I had no sense of time but might have guessed I had been there for more than an hour before Colette retrieved a bamboo cane from a large vase in a corner. The game was a distant memory. As she approached me I noted that Janey had snuck into the room. She watched as Colette traced my backside with the cane. I felt goosebumps all over.

Janey approached, "I have a fun little game if you'd like to play..."

I nervously nodded my head yes. "If you can take 10 strikes from sweet little Colette I'll unlock you and watch you have your way with the little slut. Even if you can't take 10, you need only take one more from her than she can take from you and you win."

Colette seemed unfazed.

"You must have 80 pounds on her. It's a stacked deck."

It did seem markedly in my favor but I had a suspicion that there might be more to the story.

"If I lose?"

"I imagine being humiliated by a 110 pound girl in front of me would be punishment enough."

"Fair enough." I was confident and readied myself.

Thwack!!

The first strike seared far more than I could have ever anticipated. I refrained from yelling but when the second landed in the exact same spot I howled, "AAAAHHHH!!" I was sure my skin was torn and I reached back to see if I was bleeding. As a result her third stroke landed mostly on my hand which hurt like hell but spared my backside.

"No fair!" cried Colette.

Janey warned me to keep my hands behind my back but gave me a break, "this is number four."

I had given up on getting to ten but thought I might make it to six and could win - I couldn't imagine Colette taking more than one or two. However, Colette put the next two in rapid fire in the exact same spot. I felt lightheaded and nauseous. I was covered in a cold sweat and felt my eyes watering.

"Enough!"

I needed several minutes to regain the strength to stand up. Once back on my feet, Colette handed me the cane and took her place on the bench. She opened her thighs and a pungent aroma rose from her. She hid her face in the bench in a manner that made me feel she was embarrassed by how powerfully her fragrance permeated the room. Rivulets of her excitement dropped from her pussy and her inner thighs glistened.

I hit her at half strength expecting her to cry and scream but to my surprise she moaned. I noted her fingers were folded into her introitus. Her moaning grew louder as she began to fuck herself with her fingers. I hit her three more times progressively harder with no apparent effect. I arrived at defeat at the seventh stroke as it became clear she was nearing climax. She begged me to continue. I felt red hot anger and humiliation and nearly ripped my arm off with her last few strokes. She came on stroke ten.

Janey laughed, "What a pain slut."

Colette crawled to Janey and kissed her feet. "Thank you Ms. Joubert. May I?"

"Yes."

Colette fetched a disgracefully large dildo and began to fellate it. Janey admonished her, "make him do it."

She put the dildo to my lips. I kept my lips tight and looked at Janey hoping for her to excuse me from another humiliation. There was only sadistic pleasure in her eyes and I felt my lips slowly part as she called me a dirty cocksucker. My blood boiled. I felt anger and disbelief at how easily Janey could bend me to her whims. Suddenly I was transported back to that night when Lily had me lick her cum off a similar instrument. All of the shame and intimacy and eroticism of that moment came rushing into me. A powerful wave of devotion for Janey swept over me as I accepted she knew me in a way only Lily had before.

I felt eager to show her my devotion was greater than my shame and steadily developed a rhythm bobbing my head up and down on the phallus. Colette spread my cheeks and then shocked me by licking my asshole. She forced her tongue inside me and gently fondled my balls. Between the humiliation of fellating the rubber cock as I stared into Janey's eyes and the undeniable pleasure coming from Colette's efforts my cock strained inconsolably. I could feel myself leaking. Janey's delight in my pain was obvious.

Once Janey was satisfied with my work she snapped her fingers and a clearly practiced Colette backed up against the bench and put her head back, Janey sat on her face. From the strain I saw in Colette's neck I surmised that Colette was putting her tongue in Janey.

"Now."

Colette shifted and put the dildo inside of Janey. Janey looked back at me as Colette began to move the cock in and out.

"Lick me."

I was confused - Colette seemed to have that covered. Janey leaned forward and pointed to the small of her back and it dawned on me that she expected me to humble myself once more. I had never rimmed anyone even though a few past lovers had done so to me. I'd always felt it was beneath me. Janey felt my hesitation and commanded, "lick me."

I began to refuse but couldn't get the words out of my mouth. Her pull was magnetic. I found myself on my knees, probing her rosebud with my tongue. The taste was tangy; much sweeter than I could have imagined. Janey's cries began to crescendo as I worked my tongue in and out of her asshole while Colette was furiously fucking her with the dildo and using her mouth to tend to her clit.

"Fucking Jesus!"

Janey came explosively. Her sphincter grabbed my tongue as she rubbed her cunt vigorously on Colette's face. I feared her orgasm would rip my tongue out of my mouth and break Colette's thin neck but Janey collapsed onto the bench prior to any dismemberment and started laughing from pleasure. I felt I might pass out from the pain in my groin.

Janey got up after regaining her composure. She grabbed my hand and we walked back to her place. At her door she thanked me for the night but said it was time for me to go home as her boyfriend was coming over. She kissed me on the cheek and laughed as she told me I'd missed a great game. That night Janey sent me several pics of her hands around an enormous cock and of a man licking her pussy and ass.

...

A few weeks later Janey offered to spend the weekend together. I managed to get reservations at I Sodi and at Janey's direction I booked a suite at the Greenwich Hotel. I went back to our little boutique and picked out a beautiful teddy and had it sent to her office along with flowers. Dinner was great. We both got a little tipsy and had so much fun. We went to a quiet speakeasy after for a cocktail. We picked a quiet table and were soon kissing passionately. My cock ached as Janey's tongue danced in my mouth and she rubbed my upper thighs. I eventually suggested we go back to the hotel and I was ecstatic at her agreement.

Once in the room she had me undress. She played with my cage as we talked about my chastity and how it was affecting me. Eventually, she had me kneel in front of her as she sat on the sofa. I felt a powerful desire and whispered, "Please" as I stared at the line where her short dress revealed her long bare legs.

She spread her legs subtly as I leaned forward.

"Tell me you're sorry... Tell me you're sorry for having to have your tiny cock locked up because you don't measure up."

Her words angered me but also caused my cock to strain and Janey smirked as she sensed my humiliation was exciting me.

I said, "I'm sorry for my tiny cock" more bitterly than I meant to. I worried I would anger her but her smile made it clear my reluctance was feeding her emotional sadism.

"Tell me you're sorry you get me so wet wearing your pretty panties."

"I'm sorry."

"Tell me you're sorry you're not hot enough or big enough or man enough to be anything more than my little cuckie."

"I'm sorry."

Janey savored my capitulation. I could smell her excitement and took advantage, gently spreading her legs and then pulling her bare pussy to me. Janey brooked no protest and moaned as I placed soft kisses all over her sex, from her clit to her labia to her perineum. Her skin was silky. Her labia resembled pink rose petals. As I spread them I was greeted with streams of her excitement. I pressed my tongue forward and greedily lapped up all I could reach. The pain in my cock was excruciating but it only spurred me forward. I put a finger in her and pressed on her upper ridge while sucking and lightly biting her clit. Janey's moans were becoming desperate so I added a second finger and started licking her clit - softly at first then slowly ramped up the speed and pressure. Her clit began to swell and her thighs squeezed my face as she wrapped her fingers tightly in my hair and pulled me into her. Her orgasm was explosive. I put my tongue in her to swallow all of her cum. Janey's breathing gradually slowed as she savored the decrescendo.

"My God, such a shame the Good Lord blessed you not with a cock to match your tongue."

I began to stand up but Janey squeezed my head tightly with her legs and suddenly flipped over so that I was sitting on the floor with my back against the sofa. She grabbed my hair and pushed my head roughly so that my neck was bent back ninety degrees. She sat on my face and started to rub herself. She had her right hand on the back of the sofa and the other pushing my head back for leverage. She glared down at me through glazed eyes as she rubbed herself on my face faster and rougher, faster and rougher, faster and rougher. Her excitement was flowing into my eyes, nose, and mouth. My vision blurred as I drowned in her. I felt as though my cock would burst - her debased treatment of me was exciting me to levels I'd never known. As she swung herself more violently her asshole began to pass over my mouth. I repeatedly pressed my tongue past her sphincter. It opened easily as it was soaked in her cum. My tongue in her ass was pushing her over the edge - she stopped swaying and instead stayed in place with her ass over my mouth grinding my tongue ever deeper into her and rubbing her clit on my nose. She collapsed as she came, alternately sobbing and giggling.

Once she regained her composure I sat up on the couch next to her and pleaded with her to let me out. I was beyond desperate for release. She laughed at me. I begged. I said I would do anything but all my pleading only made her laugh further.

"The only thing I need is a big cock."

It dawned on me that I needed to embrace my fate.

"I'm sorry I have such a tiny cock."

Janey grinned broadly, "Oh cuckie, I'm going to have so much fun with you!"

There was a spark in her eyes and she grabbed her phone. After a few texts she said, "Walk me to Dominic's place. He's in Tribeca not far from here."

I should have been upset but my head was in a fog from lust. As we left the hotel Janey spoke fondly of Dom and how much she liked fucking him. Along the way to Dom's apartment Janey pushed me into a deeply inset warehouse doorway. "Take down your pants." She grabbed my key from around her neck and I marveled at how easily she unlocked my cage in the dark. She had me turn around to face away from her and shoved her hand in my throat until I gagged. She grabbed my cock with her wet fingers as she told me I'd been good tonight. I was so desperate I orgasmed a minute later as she told me she would make me gag on something bigger soon. I gasped loudly as I came and Janey told me to turn back around and kneel. Her hand was covered in my cum. She curved her fingers together and put her hand in front of her crotch turning it into a faux-penis. I had never tasted my cum; the thought of doing so had always been abhorrent to me. I shook my head 'no' but resisted little as she forced her way into my mouth and then into the back of my throat. She made me gag several times and then wiped her hand clean on my face. My eyes stung as we walked two more blocks to Dom's building. She handed my cage back to me and told me to put it back on at the hotel. I tried to kiss her good night but she laughed and pulled away saying I smelled like cum.

...

I put my cage on as soon as I got back. I had the suite for the weekend and slept in after the late night. Janey texted me in the evening to meet her for dinner at the hotel. She was dressed comfortably in a t-shirt and jeans. Throughout dinner she teased me about how amazing last night had been with Dom. My cock ached as she described fucking him until early in the morning and cumming repeatedly while thinking of me and my pathetic little cock locked up.