Lily’s Orgasms

Literotic asexstories – Lily’s Orgasms by UncleFester623,UncleFester623 Author’s note: All characters in this story engaging in sex are over 18.

This story is a work of fiction. All characters and events are fictional and any similarity to living persons is strictly coincidental.

This story is a fantasy that uses themes of cheating, lactation, and taboo / incest. If these themes are not your thing. please read another story.

Please rate this story and leave comments after you’ve read. Your comments will help me write better stories in the future for you to enjoy.

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“Really?? You’ve never had an orgasm?” I asked my niece, astonished.

“Nope, never.” she replied flatly

I was incredulous. My niece, Lily, who had just turned 37, told me she never has had an orgasm.

So, you’re wondering why I’m having this conversation with my niece, as it seems quite personal, and perhaps inappropriate coming from me, her uncle, who is 55 years old.

It’s a long story…

Lily is one of my favorite nieces, who I have known since she was a toddler. My sister-in-law’s third child, Lily is a beautiful girl, always has been.

I met her when my soon-to-be wife introduced me to her family at a holiday gathering. A very lovable, cute child, I spent many hours holding her, bouncing her on my knee when she was young.

Quite innocent throughout her life, growing up in suburban, bordering on rural, Michigan, not savvy in many aspects of life, she married her high school crush after she graduated from college with an accounting degree. They took their time, established themselves, and bought a house a few years after they wed.

It took them more than a few years to have their first child. They doted on the little boy, Ricky, but didn’t spoil him. It was another six years before they had their second, another boy, Jimmy.

Within a few months after Jimmy was born, Lily’s husband filed for divorce, claiming he felt “unappreciated” in their marriage.

We couldn’t understand this, as they always appeared to be a happy couple who loved their kids, did lots of family-oriented things together, and took many trips to Disneyworld as a family and with others in family.

My wife snooped around, and talked with her sister about why they split. It took a while to wheedle the information out of her, but it was a bit of a stunner.

Lily’s husband filed for divorce because she wouldn’t have sex after the second boy was born. “Unappreciated” really translated to “not getting any.”

Pressing for further details, my wife found out that Lily didn’t enjoy sex with him because she had never had any orgasm of any type when with her now ex-husband.

She tolerated sex because she wanted kids. She apparently tolerated a lot of unfulfilling sex because the ex-husband’s sperm count was low, so it took them many, many attempts to conceive two children.

So that’s the background as to why I’m having such an intimate conversation with one of my favorite nieces.

We were on one of our not-quite-annual trips to visit my wife’s family and I found myself alone with Lily one afternoon, just talking about general stuff, nothing out of the ordinary. Her kids were with their dad, the ex, so she was free to just chat in a relaxed atmosphere, not stressed out over having to watch over two active young boys.

“So, how are you adjusting to being a single parent, Lily?”

“I’m doing fine. Mom’s always a big help and so is Allison (her older sister, with three of her own) when she can. It’s just that on days like today, when Ricky and Jimmy aren’t around, I get a little restless.”

“Restless? I’d expect you to enjoy some time alone, without the hustle and bustle of being a mom.”

“Yeah, I understand how you, or anyone, would think that, but I haven’t been alone in twenty years, or more. We dated in high school and college, then got married and settled in together, so I’m not used to being alone.” Lily explained.

I thought for a few moments and then said, “I guess I didn’t really think about it that way, but I see what you’re saying. Before you had kids, you guys could do ‘whatever’, you know? But now, you have to figure out how to do ‘whatever’ on your own.” using air quotes on “whatever” to get my meaning across.

Lily smiled and blushed, indicating she understood my innuendo. Then, she became melancholy and said, “Yeah, well, ‘whatever’ was never much of a thing for me.” and she looked off into the distance.

Knowing what I knew, or thought I knew, I decided to pursue this a little to see where it might lead.

I said, “Hmmm, when I was your age, ‘whatever’ was always a big thing for your aunt and I because it was rare that we got time alone to be intimate.” I decided to get a little more specific to steer the conversation.

Lily smiled a little, and said, “Well, I guess you know your way around Aunt Jane’s anatomy better than my ex did around mine.” She sighed heavily.

I was inwardly pleased in that I had successfully steered the conversation to where I wanted it to go.

I looked at Lily pensively, then asked, “So, you two had some issues, I take it?”

Lily looked back off to the distance and said, “Yeah, you could say that, and then some.”

Not wanting to let this go, I continued to pursue her thoughts.

“Well, I don’t want to pry, but if you’d like to talk about it a little, I’m a great listener.” I smiled my best “caring and helpful Uncle” smile.

Lily sat silent for several minutes. I thought perhaps I’d pushed her too far outside her comfort zone.

Then she piped up, “OK, I think it would be good to just talk and maybe help myself get past where I am right now.

She started slowly, “I’m kinda stuck in a spot right now. I’m not dating, so I have no prospects for companionship. The reason I’m not dating is because in today’s world, men ultimately are….” She stammered… “…interested in getting into bed with a girl.”

I nodded sympathetically, saying, “Yeah, we tend to think below the belt a lot.” and smiled.

Lily smiled back a knowing smile, “Yeah, you all do. And that’s the problem for me. I just am not motivated by having sex. I don’t get why everyone is so obsessed with laying down and getting between someone’s legs. It’s never done anything for me.”

This piqued my interest. “Never? You’ve never enjoyed having sex? Even when you were a teen and had all those hormones running rampant around your body? I mean, I know it’s different for guys and girls, but it’s not THAT different.”

“Well, like I said, my ex was not the most caring lover, and he’s been my one and only, so I guess I’m conditioned to think that sex isn’t the do-all end-all.”

I thought a little about this and decided to probe a little deeper.

“Lily, when you say he wasn’t that caring, what exactly do you mean? And if you don’t want to talk about it, just tell me.”

“No, I want to talk! He just was not a terrific lover.”

She blushed before speaking again. “He was not that big, I mean, he was maybe four or so inches when he was hard.”

Lily was bright red now.

“And he never lasted very long, so I never got close to a climax.” She sighed.

I asked, “Did you ever ask him to use his tongue on you?”

She blushed, and then laughed out loud.

“Hah, yeah, and he told me he’d never put his tongue ‘down there’ because ‘it was gross'”

I must have raised my eyebrows because Lily smiled and laughed quite a bit.

“He just wasn’t interested in pleasing me. He’d feel my boobs, get hard, pump in me a few times, blew his load, and that was that.”

I muttered, “Holy shit.”

Lily continued, “So after we struggled to have two children, both of whom I adore, I decided I wasn’t going to keep up the charade, so I told him sex was off the table. He blew up at me and ultimately filed for divorce.”

All I could say was “Wow.”

Then I thought to ask, “Did you try to go to any counseling? Marriage counseling? Sex counseling?”

Lily chuckled, “Yeah, that was a shit show. He fought it all the way and when the counselor told him he was a large part of the problem, he blew up at her and walked out. That was that.”

I was dumbfounded.

“So, Lily, you’re saying in all the years you two were together, you never got yours?”

She shook her head silently.

“Really?? You’ve never had an orgasm?” I asked my niece, astonished.

“Nope, never.” she replied flatly

I sat silent for quite a while, digesting what she had just shared with me. She and her high school crush had sex for more than twenty years of dating and marriage, and she never had an orgasm. It was mindboggling!

The reason it was mindboggling is that Lily was a beautiful woman. I knew her as a child, then as a teen and then as a college coed. She was beautiful, at least in my eyes.

Lily was maybe 5’7″ or 5’8″, now about 140 pounds, after two kids, curvy in the right places, nice smooth skin, long legs, a nice curvy butt, and, when she was first married, C-cup boobs, now probably D cups after the kids. At this stage, she was a MILF. Back in her teen years, she was thin, a nice face, had nice boobs, and a curvy ass, so she was, as far as teenage boys were concerned, very boner-worthy.

Before she was married, she was a gorgeous Midwest girl who was well-proportioned. Not stick-thin, but not fat. The babies put a lot of weight on her frame, but the stress of the divorce had taken a lot of that weight off her as she dealt with an ex who turned out to be immature, even as he approached forty.

And despite all her outer and inner beauty, her spouse could not see his way clear to meeting her physical needs. I just could not believe this! Why had they married, I thought to myself.

“Lily, I’m so sorry to hear this, and sorry to put you through all this again. I had no clue your marriage was in this kind of shape.” I was almost in tears.

She smiled at me, and saw my emotions surfacing. “Oh, Uncle Bill, it’s OK! I actually feel better having spoken to you about it. It’s been kind of cathartic!”

Then Lily leaned up and kissed my cheek, which made me blush a little. But she also placed her hand on the inside of my thigh, which caused the reaction you’d expect.

As she gripped my thigh, I turned to kiss her back, and caught her square on the lips.

She didn’t turn away; she opened her lips slightly and probed with her tongue.

My reaction was instinctive, rather than thought-out. I opened my lips and probed back. And then I did something I truly should not have. I moved her hand on to my bulge.

To my surprise, Lily gripped my stiffening manhood harder, and kissed me deeper.

Lily broke the kiss just enough to breathe, “I’ll bet you’d know how to make me climax.” before she sealed her lips to mine again.

My cock got much harder quickly as we continued to fondle each other.

I said to her, “We probably shouldn’t, but I’m sure I could bring you to orgasm many different ways, Lily.”

I began to fondle her lovely breasts through her blouse and bra.

Lily moaned softly and quickly unbuttoned her blouse and undid the front closure to her bra and placed my hand on her fleshy breasts.

I found her nipples and began to tease them, flicking them and twisting them, causing her soft moans to become much louder.

By this time, Lily was stroking my fully hard cock, and was unbuckling my shorts. She worked her hand into my boxers and found my turgid member and the precum that was coating the head. She wiped it around, which caused me to leak more.

“Lily, would you like me to show you how a loving man makes proper love to a beautiful woman?” I breathed to her.

“Absolutely, Uncle Bill. Make me scream.” she breathed in my ear as she nibbled my earlobe.

“OK, I have one condition, Lily.”

She looked startled. “What?” she asked innocently.

“Call me Bill, and keep this between us.” I smiled.

“OK, Bill, but that’s two conditions.”

I smiled. “You’re right. I guess I’ll have to give you twice as many orgasms as I planned on.”

Lily cooed, “Ooooh, Bill, that sounds like a deal to me.”

We continued to fondle, grope, kiss, and tease each other. Lily grabbed my stiff cock and stroked me with purpose. I slipped my hand into her panties and found her slit, dripping wet and very hot.

For a woman who said she was not motivated by physical sex, her body was reacting quite the opposite.

We moved to a bedroom.

I gradually stripped off Lily’s clothing, and she did the same to me.

Her boobs were beautiful, and given that she had an 18-month-old, I was hoping she might have a little milk left in those gorgeous breasts. I had a thing – a big thing – for lactating women.

I latched on and began to suckle, working to coax any milk out of her that I could.

Lily gasped and yelped, “Oh, Bill, you’re gonna start my letdown!”

I smiled as she said this. I broke free and told her, “That was my goal. I’m going to suckle you for a while. I love mommy’s milk!”

“Well, Mommy is gonna fill your tummy full!” she said huskily.

Lily moaned and pressed me against her breasts as I suckled and began to taste her milk. I felt her other breast begin to leak against my chin. My cock got harder.

I’ve always had a kink for lactating moms, and Lily was satisfying my kink. I was nursing from her, swallowing her nectar.

She was enjoying the sensations, her head thrown back as I squeezed her nipple between my lips and sucked her life-giving milk into my mouth, swallowing every few suckles.

After about fifteen minutes, she motioned for me to switch nipples, which I did in a smooth motion. I immediately latched and began to suckle.

Again, Lily gave me every sign that she was enjoying my attention to her breasts. She moaned softly as I suckled, cooing into my ear, “That’s it baby, drink up momma’s milk.” as she ran her fingers through my hair.

It was incredibly intimate and erotic.

I felt the flow of her sweet, warm milk slow. I let go of her nipple with a loud pop. Looking up at her face, she was in ecstasy.

I slithered down towards her crotch, kissing the whole way there. I continued to play with her nipples, but changed my focus to her neglected pussy.

Lily was drenched. For someone who claimed to have never enjoyed sex, her body was sending signals that what I was doing was making her happy. I licked up and down the insides of her thighs, eliciting sharp gasps and moans from her.

She thrusted her mons towards my face, trying to get my tongue and lips to dig into her long-neglected pussy.

I was taking my time, being very deliberate in my attentions. I wanted Lily to be thoroughly stimulated, and wound tightly before I went in for the final act.

I licked up and down her labia, not touching her clitoris, not driving in to her inner lips.

Her involuntary thrusts and clenches around my head told me I was doing all the right things for her to bring her off. I gently dipped my tongue between her lips, causing her to inhale sharply, yelp, and squeeze her thighs harder around my head.

I drove my tongue deeper and deeper into her no-longer neglected pussy, driving her to buck wildly. I kept at it, making her moan and gasp loudly until she finally cried, “Bill, just shove your tongue deep in me, make me cum!”

I had her close, so I kept driving my tongue into her pussy, and then I licked up toward the top of her slit and found her hooded and well-hidden clitoris.

Lily cried out as I brushed her clit with my tongue, “Oh my god, oh my god, oh my god, Bill — right there! RIGHT THERE! Do it right THERE!”

Well, it was time for me to give Lily, a 37-year-old mother of two, her very first orgasm. I slid my tongue into her pussy just below her clit, coaxed her clit out of its hood, and sucked it into my mouth.

Lily gasped and gurgled as I did this. She was on the edge, and I was about to push her over that edge.

I used my tongue to press her clit to the roof of my mouth and then sucked it into my mouth, pressing hard against the roof.

Lily bucked hard, nearly causing me to lose my grip on her clit. She shrieked, shuddered, shook, and squeezed my head with her thighs so hard I thought I might die.

I’d delivered to Lily her very first orgasm.

After convulsing for what seemed like minutes, Lily calmed and relaxed her thighs, allowing my head to move again

I gently released her clit, but slowly sucked it to prolong her orgasm. She shuddered throughout my ministrations until she was no longer able to move.

I lifted my head and slowly moved back up her body, kissing and sucking her nipples along the way.

“Oh my god, Bill! That was exquisite! I’ve never experienced anything like that before. Are all orgasms like this? This intense? This mind-blowing?”

I chuckled and said, with love in my voice, “They can be, so long as your lover pays attention to your body’s signals. But, because this was your first orgasm from a lover, I’d bet that was a big contributor as well.”

She smiled and laughed, “Well, you’ve set the bar pretty high, and you’re going to have to show me what I should expect in the norm!”

I smiled and said, “I’ll show you whatever you’d like. But, is it safe for us to continue? Are you on birth control?”

Lily giggled, “Yes, I went on the pill right after Jimmy was born. I didn’t want to risk any more kids with the ex, regardless of how little chance there might be.

I smiled and said, “OK, but do you want to use a condom anyway? Just to prevent STDs?”

Lily laughed heartily. “Well, I know I’m clean. I haven’t had sex in nearly two years. I’m assuming you’re clean.”

I sighed, and said, “Yes, I’m clean. Jane and I don’t really do it anymore and I’ve been strictly monogamous forever.”

Lily smiled and then purred, “Well, we’re going to change that, aren’t we, Bill?”

I smiled back and said, “If you’re willing.” with more than a little bit of a smirk.

Lily quipped, “I’m more than willing. I’m demanding it!”

With that, Lily rolled over on top of me and began kissing me. We passionately French-kissed, our tongues nearly knotting as we probed deep into each other.

Lily’s kisses worked around to my ear, where she slipped the tip of her tongue inside for just a second before she nibbled my earlobe.

She worked her way down the side of my neck, to my shoulder, and then my nipple. Lily invested quite a bit of time licking, kissing, and sucking my nipple. She was doing excellent work getting me aroused.

“Lily,” I murmured, “for someone who claims to not have enjoyed sex, you seem to be quite good at turning me on.”

“I may not have enjoyed sex, but I know what I like to have done to me, and that’s what I’m doing to you, so pay attention!” she said through a lewd smile.

She certainly had my attention. And she had my manhood at full attention again.

Lily continued down my body, arriving at my crotch. She breathed her hot breath all around my hardened cock and tightening balls, but she moved past, kissing and licking down the insides my thighs, then behind my knees and finally to my feet.

To my surprise, Lily began kissing and sucking my toes as if fellating them. It felt wonderful to me, and kept my hard cock very hard.

Once she finished my feet, she came back to my crotch and began to first caress my cock and balls gently with her small, soft hands until I was quietly moaning.

“Lily, that feel so good, keep going.”

She giggled and then began to lick my stiff manhood up on side and down the other, pausing at the head and spending some time using her tongue all around and over it, cleaning the precum off as it oozed out.

“So delicious!” I heard her whisper.

Lily paused momentarily, then took my veiny pole into her mouth, swirling her tongue around it and corkscrewing the bottom half with her hand.

She was very skilled handling my cock, as her ministrations left me feeling euphoric. But she had held back, for at this moment, Lily swallowed my fat, stiff cock all the way down to the base without so much as a blink of her eye.