Lily's Wish

This is a story about female domination. Themes include cuckoldry, chastity, creampie cleanup, and humiliation. If this bothers you feel free not to read. Janey, the female protagonist in this story, is meant to be the same person as in the story, 'Janey'. The male protagonist in this tale is a different character from the male protagonist in that story.

I was startled to get Janey's text. She was checking up on me - it was a simple message asking me how I was doing. I appreciated her concern but didn't return the text. My wife, Lily had passed away from an aggressive cancer three months before and I was still oscillating between rage and anhedonia. Janey was a friend of Lily's and frankly she intimidated me. She was gorgeous but also brilliant, relentlessly honest, and matter of fact.

It was the third time she had reached out to me since the funeral and I had yet to respond. I felt guilty. Later that night I crafted several texts in response over day-old frozen pizza and a few beers but I never hit 'send'.

Two weeks later, Janey strode into my office around noon without an appointment. My assistant was frenzied behind her. I was impressed. I was the executive VP of Security for a Fortune 500 firm - getting into my office like that should have been impossible.

"It's ok, you can let her in."

I got up and embraced Janey. I apologized for my lack of communication and broke down as she told me she understood. We sat at my conference table for hours talking about Lily and the inequities of life. Lily and I met twenty years earlier when I was finishing up my MBA at Columbia and she was starting med school at NYU. We'd been married for 17 years and life without her seemed impossible. Lily had been so much fun - we travelled a lot and loved each other's company. We were never blessed with kids but that helped to keep our sex life creative and dynamic up until the end.

Janey surprised me when she confided that Lily had asked her to help me get through by taking me under her wing. Lily and Janey had become friends after Lily started taking yoga classes at the same studio as Janey. I wasn't sure how this young woman could "take me under her wing" but I was flattered to have Janey's attention and felt positive for the first time in months.

We started meeting weekly for drinks. Our conversations were fun and easy. Janey encouraged me to stay active and I started working out again. She had a way of directing me in a manner that felt natural and calming. I found myself reading books and watching movies she recommended. I enjoyed her satisfaction when I did so. I was 15 years older than Janey but often felt like a schoolboy trying to impress a favorite teacher.

She knew Lily better than I realized. It took months but gradually our conversations began to veer into personal arenas and I started letting my guard down more and more. Janey encouraged me to be more social and I started seeing friends more often. These outings frequently provided opportunities for brief romantic dalliances that I occasionally took advantage of. Janey encouraged and loved hearing about my trysts. She assured me Lily wanted me to enjoy life and that I would know when I was ready for a relationship. I found it embarrassing to speak in detail about sex with Janey but I pushed myself to suppress my inhibitions.

One warm spring evening I felt bolder than typical due to two martinis on an empty stomach.

"Want to hear something funny?"

"Sure!"

"Years ago I asked Lily if she would be interested in a threesome with you."

Janey smirked, "not exactly ha ha funny, is it?"

I regretted bringing it up and hesitated. I was transported back in time - that evening was still seared in my memory. I had asked Lily for the threesome in a half-joking manner for plausible deniability. Lily had never been with a woman and my infrequent requests annoyed her. However, to my great surprise, this time Lily responded enthusiastically. She was meeting Janey that night for a girl's night out and hinted she would try to bring Janey home. Lily was 13 years older than Janey and while she maintained a youthful vitality and beauty, frankly she wasn't in Janey's league. Nevertheless, Lily had a seductive sensuality and fierce determination. I spent the evening fantasizing about fucking Janey and Lily.

Lily came home late and seemed upset. She was drunk and nearly tripped on the coffee table as she sat on the sofa next to me. She was unaccompanied and started weeping quietly as she buried her head in my shoulder. It took a while before she would tell me what happened but eventually she shared that Janey had seemed interested but started asking questions about me. Lily said she talked me up to Janey but when pressed she had to admit I was on the smaller side and Janey lost interest. Lily's words weren't meant to be hurtful but when she said, "I couldn't exactly lie, could I? She was going to see that you're not big" it felt like she had punched me in the gut.

Lily felt bad about hurting my feelings. She put her hand in my shorts and began to stroke my cock. She assured me she loved me and my cock. I was upset though and couldn't get hard. I started to get up to go to bed but Lily grabbed my hair and pulled me into her lap. Lily was assertive with a few drinks in her and told me she was horny and expected me to go down on her if I couldn't fuck her. I wasn't in the mood, but I couldn't refuse either feeling as inadequate as I did. I tried making myself hard but couldn't with her watching me. She told me she was tired of waiting, spread her legs, and I moved to my knees. She lifted her dress and pulled me in. As I licked her she told me I was way too small for Janey. That Janey had literally laughed at her. I looked up at her and apologized. I couldn't stop myself from asking if Josh, her former boyfriend, was bigger than me. She confirmed and then closed her eyes; I imagined that she was thinking of him. Lily came powerfully and her cries of pleasure made me ready for action. I climbed on the couch and started fucking her. I felt as though I was on the precipice of reclaiming my manhood when Lily stuck a finger in my ass and told me to make my little cock cum. It was too much and I came hard.

...

I was startled back into reality when Janey grabbed my hand.

"Where did you go?"

"Oh, I don't know," I wanted to disappear, "down an emotional rabbit hole I guess."

"You know, Lily told me about your request at the time. She wanted me badly -- more than you know but she loved you dearly and never strayed or deceived you."

I made myself stop thinking about that night.

"I considered it - Lily told me you were a generous and attentive lover. And that you tried earnestly to make up for what you lacked in the penis department with your tongue, lips, and willingness to follow instruction."

My face was beet red and I felt shaky. I was so discombobulated I didn't notice Janey's hand in my lap until she was stroking me through my pants.

"Are you erect?"

I grabbed my water and drank the full glass in one gulp. I nodded yes.

Janey smirked, "I couldn't really tell."

I prayed for lightning to hit me.

"You know after Lily discovered that she was dying, she took me into her confidence about her sex life with you and some of her previous romantic exploits."

I was taken aback but not shocked.

"Did she tell you about my dominant relationship with men?"

"No... what does that even mean?"

"A simple way to put it is that while I don't necessarily think all men are inferior to all women, I do believe all men should believe they are inferior to the woman they are committed to and act accordingly."

I was perplexed, "I don't get it."

"Do you think I'm interested in you sexually?"

"No, I guess not? Maybe...?"

"You know I'm not, don't you? You know that I find you... inadequate to be delicate."

I looked down. I felt humiliated.

"You know that don't you? Lily told you, didn't she?"

I nodded 'yes'.

"You are attracted to me though."

I nodded again.

"We both know that you would go to great lengths to get in my pants."

"What's the point of all this?"

"It's that imbalance that I find intoxicating. One person is superior, the other inferior. All the men in my life are inferior to me even though they are better looking, fitter, and much more endowed than you."

"But what does that mean?"

"You can find out if you want to. When Lily learned of my dominance she confided in me about your submissiveness."

"I'm not submissive!"

Janey smiled as she rolled her eyes.

"I make a shit-ton of money. I have 80 reports and kill it at work. There's no way I'm submissive! I work in security for fuck-sake!"

Janey looked at her phone and I could feel her thinking, "I don't have much time but follow me."

We walked a couple of blocks to a small boutique. Janey apparently knew the salesgirl as she whisked us into the back to a room filled with lingerie. Janey looked around for a few moments before grabbing a pink pair of silk panties. They were far more modest than anything Janey had worn during her appearances in my fantasies.

"Buy these."

I handed my credit card to the salesgirl and Janey handed the panties to me.

Janey announced, "The submissive gentleman will be wearing his new purchase out."

The salesgirl giggled and pointed to the changing room.

"That won't be necessary, he'll change here in the back as we watch."

It took me a while to register what was happening.

The salesgirl let out a happy, "yay!" and ran to the front to lock the door. This clearly wasn't the first time this had happened.

I protested, "I'm not going to wear these."

Janey stepped closer to me. She was an inch taller than me in her stilettos and narrowing the distance between us forced me to look up at her.

She used an even tone as she said, "I want to watch you put them on."

I felt awkward and pleaded, "Why?"

Janey repeated herself, "I want to watch you put them on."

I wanted to leave but I couldn't. I felt glued to the ground. I whispered, "Please don't make me."

She beckoned the salesgirl.

"See if he is erect."

I closed my eyes out of shame as she put her hand in my pants and grabbed my throbbing cock.

"He is! OMG, gross - he's totally leaking." She pulled her hand out quickly and wiped it on my shirt.

"So, your little cock is hard as you plead with me not to make you put these panties on. That feels pretty damn submissive to me."

She turned to the salesgirl, "what do you think Colette?"

Colette laughed and blushed, "Totally!"

Janey stepped even closer.

"Now."

I knew I had lost and undid my belt and took my shoes and pants off. Soon I was half-naked in front of them and they laughed at my expense. Janey placed her hand on my cheeks gently and brought me in for the briefest of kisses once I was dressed again with the panties on.

"I take it you understand the point I made?"

"Yes." I replied softly.

"Great! I'll see you next week!"

I walked out behind Janey and watched her perfect ass sashay downtown before I grabbed a cab home. It struck me that my mind was fantasizing about licking her ass, not fucking her ass.

...

I wrestled with what had happened all week. Part of me dreaded seeing her again but I also knew I would walk over hot coals to make our next date. Every day I thought of reaching out to her but I opted not to do so out of concern I might come off as needy.

In spite of my anxiety, I was delighted to see Janey again. She greeted me warmly which soothed me greatly. We chatted for a while but eventually Janey got down to brass tacks.

"As I mentioned last time, when Lily learned of my dominance she confided in me about your submissiveness."

Janey paused, "doth the lady protest?"

I was annoyed by the moniker 'lady' but thought better of complaining.

"No, you have me pegged," I admitted.

"Pegged? Interesting choice of words..."

I laughed in a manner that belied any ignorance of the term.

"After Lily knew she wasn't going to make it she asked me to take you on as one of my submissives. She told me she would tease you about not being big enough for me and how excited it made you. She thought it would be good for you. To be honest, I struggled with the decision. I made it clear I would not let you interfere with my primary relationships or with my desire to have multiple submissives in my world. She, of course, agreed and so I accepted."

I took it all in; I was incredulous! At the same time it was impossible to ignore that my cock was rock hard thinking about what she said, "so you two negotiated my future without my input?!?"

Janey replied, "Yes" as she deliberately knocked her fork off the table. "Be a darling, and retrieve that for me."

I looked under the tablecloth to locate it and felt my cock throb. My internal debate was short. As I succumbed and moved under the table I marveled at how she made me feel powerless. I felt utterly seduced by her strength.

Janey told me to hand her the fork back to her from my knees. As I did, Janey told me to stay on my knees. It felt like hours and that the whole restaurant must be staring at me but I waited obediently until a few seconds later when she signaled me to get up.

Janey looked pleased as I sat back in my seat. She put her hand on mine and said, "Tell me about Lily teasing you."

I was reluctant to share and stared at our hands before I finally started to speak. Janey had to tell me to speak louder as I confessed what happened that fateful night. I could tell she already knew the gist of the story but enjoyed hearing more detail and my perspective. I proceeded to volunteer how that night had impacted us. I told her how a few weeks later we came back home from a house party where Lily had run into an old college boyfriend. We both got a little tipsy which led to us kissing and fondling each other in the cab on the way home. As we neared our building I asked Lily if he was bigger than me. It wasn't premeditated - we were both surprised I asked. Lily seemed annoyed at first but I noted an impish smile as I opened our door. Once inside we undressed hurriedly and rushed into the bedroom. Lily sat on the edge of the bed and told me to lick her. I got down on my knees as Lily told me that her ex was bigger than me. Much bigger. She reminded me of Janey laughing and refusing me. It continued all weekend - me on my knees licking her as she teased me.

A few weeks later Lily had tied me up in bed, sat on my chest, and fucked herself with a huge dildo before making me lick her cum off of it. We began to play with the idea of her taking a bigger lover but it never materialized and then she took ill. Looking back I began to wonder if Janey had influenced Lily.

Janey listened attentively. As I finished she shifted in her chair and then brought a hand into and out of her lap. She offered her fingers to me - they glistened with her excitement. I let out an involuntary moan as I cleaned her fingers with my mouth.

"You made me so hot."

She got on her phone and sent a couple of texts. Her phone dinged and she called someone. "My new cuck just got me so wet. Are you home?"

She grinned and said, "I'll be there in 20."

She kissed me on the cheek and told me to go back to the boutique and to ask Colette to help me.

"I'll be coming over to your place tonight."

I was stunned. So much had happened. I felt like I had lost free will. What did she mean by 'cuck'? A million thoughts raced through my head as I walked back to the boutique.

Colette smiled when I came in and reached under the counter for a small box, "good timing, it just came in. Don't open it until Ms. Joubert tells you to!"

The box was small but ornate and weighty. I handed her my credit card but she refused, "it's been taken care of... would the gentleman care to purchase more lingerie?"

I bristled at her question - I didn't need some 20 year old kid mocking me. I turned to face her and was about to yell at her but just before the words spilled out I regained my composure and thought better of it. I knew Janey wouldn't appreciate an outburst on my part.

I took a few deep breaths and calmed myself, "what would you recommend?"

I followed Colette into the back, "I think you should get something for yourself to show you know who you are and a gift for Ms. Joubert to thank her for showing you who you are."

I nearly lost my temper again but stayed quiet.

Colette sensed my mood but remained lighthearted, "I can help if you like."

I nodded and Colette thought for a moment and then quickly grabbed a few pieces.

"Ms. Joubert likes these negligees and she tells me one of her boys always ruins them while ripping them off of her."

She held up a similar piece over her chest, "I lovelovelove this. Will you get it for me?"

"Of course."

She handed a pair of panties to me. "Put these on in the changing room but give me your card first and I'll ring everything up. Thank you!!"

I couldn't believe I was doing this again. Colette walked in without knocking as I was disrobing to hand me my card and a bag, "here you go."

She stayed in to watch me and told me to take everything off and then to put on the panties, "you look so pretty! Turn around. Yay! I love it!!"

Her phone dinged and she let out a high pitched yelp, "OMG, look at this."

She showed me a pic of a small hand on a large cock, "Ms. Joubert's amuse-bouche."

Colette reached down and began to stroke my cock. I quickly hardened. She grabbed her phone and asked, "May I?" I looked away as she shot her hand on my cock and sent it to Janey.

She doubled over in laughter at Janey's response but didn't share it with me.

...

I waited at home anxiously hoping to see Janey. I felt ridiculous in the panties and angry at myself for being so easily manipulated yet I couldn't ignore my raging hard-on and non-stop thoughts of Janey being fucked by another man. I tried to extinguish thoughts of me kneeling before Janey licking her as she recounted the afternoon with her lover but the scenario kept returning. I often fantasized about licking Janey and could not get the image out of my head. My cock would spasm uncontrollably with perverse thoughts of her fucking another and then me attending to her post-coitally.

When Janey arrived she looked great and hugged me tightly after handing me a bottle of wine.

"I had such a fantastic day! Let's toast."

I opened the bottle and we moved to the couch to drink to her day. Janey was a lawyer and she caught me up on a couple of her cases. I'd asked around and knew she was considered a superstar in her space. It was fascinating to listen to her describe how she thought about her cases. Eventually, the talk turned to us and Janey told me she was enjoying my company much more than she anticipated. She asked me to get the box and open it. I also retrieved her gift. Janey loved the negligee and smiled broadly as she told me her boyfriend would be so happy.

I felt deflated hearing the word 'boyfriend' but put on a brave face as I opened my box. The color drained from my face as I pulled out a chastity cage. It was gold and heavy enough that I reckoned it was gold through and through. I'd never seen one in real life but I knew what it was. I hid my disappointment and thanked Janey but she picked up on my conflicted feelings.

"It's custom made in Rome. I had it engraved. I hope it fits, I made an educated guess on how small your little cock could be."

I inspected the cage and saw it was engraved "cuckie". She showed me how it worked and told me she would put it on as soon as I begged her too. I felt relieved as that seemed unlikely, nevertheless, everything hit me suddenly and I was overcome with emotion. Janey held me as I regained my composure. Once I came back to earth, I moved to my knees and looked up at her, "I want to make you feel good."