Lola Puts the “Fun” in Fundamental Fantasy

Lola Dreams of Gang Bangs

 

“Lola, by any chance did you watch Lily Phillip’s fucking a hundred cocks?” I asked over breakfast.

“Who do what?” she replied.

“Don’t be coy.”

We were sitting on the roof deck of a fancy five-star hotel in South Beach.  To my right was the famous Ocean Blvd. and then the Atlantic.  To my left was the roof deck pool, cabanas lining the side of it, and a bar at the far end.  In the pool and lying out in the early sun were topless women and their husbands sunning themselves and drinking cocktails.  It was only ten in the morning, and at that hour a Bloody Mary is basically breakfast.  Or, at least it is when you’re on vacation.

“Of course I watched it,” she finally blurted out.  “Why?”

“I was reading an article this morning that was quite enlightening about it.”

“I bet you were,” she said with jealous derision in her tone.

“Do you care to read it?”

“What’s it called and what do you find so fascinating about it?”

“It’s called ‘Lily Phillips: One Woman’s Dream of Don Juan’ or something like that. In a nutshell, it says that there is an archetypal sexual fantasy for men and another for women.”

“I’m curious.  What would those be?”

“For men, it’s the – well, it’s a little difficult to explain,” I stumbled over my words.  “But basically, every man fantasizes about being an Alpha Male on steroids.”

“What does that mean?”

“Just imagine Rocky, The Terminator, John McClane from Die Hard, all rolled into one.”

“I get it, like Tyler Durden is to what’s his name in Fight Club.”

“Exactly.  And, he doesn’t have a name.”

“The fantasy figure?”

“No, the narrator for Fight Club, played by Edward Norton.  He’s so castrated that he doesn’t even get a name.”

“Castrated?”

“Never mind.”

“And what is a woman’s fantasy?  Please, do tell,” she said sarcastically, underscoring that it is not a man’s place to tell a woman her fantasy.

“According to this article, Don Juan.”

“Don Juan?” she repeated, stunned.  “He’s a male fantasy, if anything.  I mean, he is the prototype for those movies you just mentioned.”

“That’s what’s interesting about this essay,” I said.  “It’s a little too convoluted for me to explain.  Why don’t you read it yourself.”

I texted it to her.  She finished her breakfast, stood up, removed her bikini top, and sat in one of the lounge chairs facing the pool, phone in hand, reading the article.

I ordered a mimosa and sat across the pool from her.  I watched her from behind my dark sunglasses as her left hand held the phone in its palm and her right hand moved lower and lower down her abdomen, to her bikini bottom, and then between her legs, where she pulled the thong to the side and revealed her long, meaty labia.  She slowly stroked them in full view of all to see – especially me.

The boys get a real thrill when Lo’s around

When she was done with the article, she looked up from her phone.  There, in the pool, were at least two men and a few boys who had been spying on her just as I had been.  Let me be clear, everything she did was unconscious.  When she’s engrossed in something – a movie, a book, an article – she is oblivious to the onanistic meanderings of her free hand.  But her audience was engrossed in her.  Each of them – including me – tried to pass it off as if they hadn’t noticed a thing, but it was abundantly evident – to me and everyone else, especially the wives and moms around the pool – what captivated their attention.

She glanced over the brim of her large and dark sunglasses, smiled, fixed her bikini bottom, and walked to the bar where she sat on one of the stools.  It was a small, tiki-style bar, only big enough for four patrons at a time.  She waited for the bartender who, at that moment, was delivering a tray of drinks to various patrons around the pool.

I met her over at the bar and said, “Well?  What did you think?”

“I like that the author doesn’t deny Lily Phillips her right to claim her own pleasure, her own fantasy.  I like that he doesn’t say, “She says this, but she must be wrong.”

“And?” I was expecting a critique.

“I also agree with the observation that no man, no matter how virile, can ever get it up enough.”

“I thought you’d like that.  I mean, that was the theme of our second book, More!, after all.”

“But,” she began.

“Ah-ha!  I knew there was a but.”

The bartender returned to his post and asked Lo what she’d like.  Lo got excited.  She stood up from the stool and was now bending over, leaning on the bar, showing her thong-clad butt off to her loyal fans in the pool.

A.I. of Lola by the pool

“Hmmm,” she said, licking her lips, “you have all these specialty cocktails.  I love their whimsical names!”

“I think she’ll need a minute,” I said to the bartender, with a wink.

She was wiggling her butt in anticipation of the fun drinks, like a puppy excited to play.

“So,” I said, bringing her back to the conversation.  “What is the but?”

“Well, I think there are a lot of fantasies – not just two.”

“Fair, but I think he’s talking about a fundamental fantasy.”

“You know,” she said, looking at me now, “even Don Juan wasn’t so simple as people make him out to be.”

“Your point?”

“Well, when he was a young man – I mean, really just a boy – he was sold into slavery and then, when spied by the sex-starved sultana, Gulbeyaz, she had her eunuch buy him for her, dress him up as a harem girl, and sneak him into the sultan’s seraglio for him to please her on the sly.”

“You mean, in Byron’s telling of the tale,” I said.

“Of course Byron!” she responded.

“And your point?” I asked again.

She turned her head over her shoulder and looked at her admirers in the pool.

“Well, maybe Don Juan is a woman’s fantasy, just not the Don Juan who beds all the women.  Maybe the Don Juan who. . .”

“Lo, I think I know where you’re going with this.  You weren’t dreaming of Lily Phillips while reading that article over there,” I nodded to where she had been lying down.  “You were dreaming of MILF Meri’s son.”

“Por qué no los dos?”

“Madam?” asked the bartender.

“I’ll have the Red Headed Slut shot,” said Lo, licking her lips.

“Very good.  And you sir?”

“The Blue Balls shot.”

Meri and son with a bull

Stiff Competition

Lola didn’t know if she was in trouble, but she was on her way to meet the director of the sperm bank.  She walked down the long hallway, lined with the framed color posters of David Hamilton’s work, and at the end of the hallway she knocked.  “Come in,” she heard a man’s voice say from behind the door.

Art by David Hamilton

Art of making art by David Hamilton

Art by David Hamilton

We shall save for later what transpired behind the director’s closed door after Lola entered it, but for now, let us pick our story up when Lola arrived at the clinic for a third appointment with Terence.

They met in the parking lot, as usual, and Lola was wearing her long white coat, but this time she had a surprise for Terence under it.  Or rather, she had nothing to surprise Terence with under her coat.

Inside the clinic the receptionist again directed them to room #3.  Upon entering, it was Lola who was surprised, for on the walls, in place of the framed posters of Lola’s cream pies, were framed posters of Ellie, the night-shift receptionist who had helped Terence by coaxing his cum out of him (before Lola fulfilled that job) and by reading to him from Match, Cinder & Spark.  Apparently, she found out about the Lola poster substitute and that Terence was “two-timing” her with Lo during the day.  She took liberties and removed Lo’s framed photos, replacing them with her own.

Ellie Mowbray

Ellie cumcovered

One poster was a black-and-white of Ellie, nude, spread eagle with cum covering her hairy pussy.  The other was of her on her knees taking one cock in her mouth and two cocks on either side of her as she stroked them off.  You couldn’t see her face in either of those posters, but, just to make sure there was no mistake, there was a framed photo of Ellie in a salmon colored outfit of shorts and an oversized blouse wearing glasses and smiling or almost laughing.

Ellie Mowbray

Ellie knows how to please three guys at once

Lola thought, “It’s on.”

“Whoa!” said Terence upon seeing the framed photos.

Ellen Mowbray

“You know her?”

“Um, yeah.  She’s the one who used to help me out.  She works the evening shift.”

Lola began to walk out of the room.

“Hey!  Where are you going?” asked Terence, confused.

“To request another room.”

“Why?”

“I find it rude.”

“Rude?”

“Desperate.”

“Desperate?”

“Thirsty.”

“Thirsty?”

“Is there an echo in here?  Look, she’s clearly still salty about what happened with Steve.”

“Steve?”

“Her ex-boyfriend.”

“What happened?”

“Ah, you can read all about it on the blog.  She’s just being petty.”

“Maybe she wanted you to see it.  Maybe it’s for your pleasure?”

“You like?”

“Honestly?”

“Yeah.”

“I do.”

“Fine,” said Lo.  “Pull out your pud.”  She was very matter-of-fact.  No seduction, no sensuality, no affection.

Terence, who had been looking forward to this for days, was eager to comply.

Lo then opened her overcoat to reveal she was wearing absolutely nothing under it!

“Ellie ever help you like this?” she asked.

“No,” he said.

Lo put on the latex gloves, lubricated, reached down between his legs and began stroking him.  She leaned forward so that her breasts were dangling tantalizingly in front of his face.  She exaggerated her hand motion so that her heavy breasts wobbled and banged up against one-another.  He couldn’t take his eyes off her heaving mounds.  Lo slowly slid her hand down below the shaft of his cock to his large balls.  She massaged them and fondled them, gently playing with them with her fingertips.  He clearly liked it.  Lo didn’t speak this time.  She just watched his facial expressions.  Her focus went from his face to his crotch and back again.  And again.

She then surreptitiously slid her index finger down below his balls to his perineum.  She used a feather-light touch on it for a while and then cautiously, furtively slid her index finger further south to his anus.

“Are you a top or a bottom when you’re with men?” she asked.

“Switch,” he said in a tense whisper.

“Stand up,” she commanded.

He got up out of the chair.

“Turn around,” she ordered.

He complied.

“Bend over,” she said, “and let’s have a full rectal exam.”

He bent over.  She inserted one, then two, then three fingers of her right hand as her left hand reached around and stroked his cock.  He was looking up at the large poster of Ellie on the wall.  Lola was too.  Lo continued her erotic massage, but it wasn’t long before he said, “The cup!  The cup!”

Lo passed him the specimen cup and stroked him as he held the jar in front of his cock and filled it with more of his donation than he ever had before.  His knees buckled and his entire body went tense and spasmed.  He could hardly stand.  He let out multiple calls of Lola’s name.  Then he collapsed back in the chair, his cock still twitching.

He passed the collection cup to Lo who screwed on the lid tightly.

Lo smiled at him as she stood before his depleted body.  The contrast between her tall, strong, lusty, flush and full body standing naked over his weak and limp body couldn’t have been more pronounced.  She removed her gloves and threw them in the special trash bin for contaminated waste.

After he regained some of his vigor, she said, “Now you stand up and let me have the chair.”

He complied.

Lo sat in the chair, put her feet up on it, spreading her legs, and she began making small circular motions over her clit with her right hand.  He watched her intently.  Her movements increased in speed and intensity until she was now rubbing up-and-down in small, rapid strokes.  This technique got more intense still until she was patting and then slapping her wet pussy.  She progressed to inserting one and then two fingers deep in her pussy.  She fingered herself for about a minute until SPLOOSH!  She squirted straight ahead, sprinkling Terence with her holy water.  It was a long, strong, and voluminous stream that soaked him and his clothes.  He didn’t seem to mind.

Ellen Mowbray

Ellie leaving work after a hard day

Ellie Mowbray

Ellie getting off after a hard day at the masturbatorium

Elln Mowbray

Ellie third from right

Fat Fetishizing

 

Painting of Lola by Erics Figure Art

[Continued from Feedie for a Night]

It was the Saturday before Halloween.  The night of the party.  Lo had tried on, adjusted, removed, retried, readjusted the Princess Leia costume at least ten times.  She tried manipulating a sash to go across her tum, but that didn’t work.  Not only would it not stay up, it also disguised the costume to the extent that she just looked like a woman from 1001 Nights.  She tried a cape that, if she felt she needed it, she could drape it around her.  She thought that would be a good compromise and she tucked the cape into the collar of the costume.  But it kept falling out.  She tried using a binder clip to affix it, but that was uncomfortable.  In the end she said, “Fine.  Fuck it!”

“That’s what everyone will be saying to you at the party,” I reassured her, “Very fine.  I’ll fuck it.”

“I’m not an it,” she reminded me.

“I know, but I get poetic license for the sake of a pun.”

“Whatever.”

She was in a grouchy mood because, no matter what she did, her round rolls of her tum were prominent.  “It’s like I have three sets of tits,” she complained.

“What?” I asked.

“Here, here, and here,” she said, running her hands over her breasts and then her first roll round the middle of her tum and then her second roll just above her black triangle.

“Lo, but that’s what Mr. Biggs (and I, if I say so myself) find so fucking attractive about you!”

“Fat fetishizing.”

“Darling, if you weren’t fat, I’d fetishize on something else about you.”

“So you’re saying I’m fat!”

“You said it!”

“Grrrrrr.”

BBMPDG Lola

Lo’s phone rang.  It was Mr. Biggs.

“I gotta run!” Lo said to me, darting towards the door.

“No kiss?”

She scuttled back in her brown, strappy heels to give me a peck on the cheek.

“I wish I could go with you,” I said.

“I’ll tell you all about it,” she said with a wink.

“You’ll have fun at your party,” she said.

As it turned out, I had been invited to a party down the street.  Lo said that if the party she was going to with Mr. Biggs was a bust, then she’d join me.  In order to keep with her costume theme, I had bought a Boba Fett outfit, just in case.

Lo was off.  I heard the car pull away from the curb.  For an account of the Hutt’s mistreatment of the Princess, I had to wait until later that night when Lo returned home.  She never did make it to join me at my humdrum Halloween party.

A.I. of Lola and Leia with Darth Vader

It was past three in the morning when I heard the clickity-clop of my princess’s heels on the wooden floor in the hallway.  She took her shoes off there and then silently slipped into the bedroom and into the master bath.  She turned on the light and left the door slightly ajar.  I saw her from the darkness of the bed as she brushed her teeth, still dressed in her costume.  She then sat on the toilet, peed, and came to bed.

“Daddy, are you awake?”

I feigned sleep.  I didn’t want her to think I was so eager.

“Daddy,” she whispered again, closer to my ear.

I grunted.

She reached for my cock under the covers.

“You’re hard,” she whispered with joy in her voice.  She wanted to get laid, I could tell.

I grunted again.

“Stay asleep,” she coaxed, “roll on your back.  Let me use your cock.  I’ll be quick, I promise.”

I rolled on my back.  She pulled my pj bottoms down.  She lowered herself down on my erect shaft slowly.  She was soaking wet.  I slid in easy as could be.

She began bopping up and down, using her index and middle fingers of her right hand to rub circles around her clit.  She was cumming within seconds.  Her moans, groans, and prayers to God were not quiet.  I opened my eyes.  I saw she was still in her princess getup.

“Lola?” I said, as if startled from a dream.

“Shhh, Daddy, I’m almost done.”

“How was your night?” I asked.  I didn’t want her to be done.

“It was good.”

“Good?” I asked.  I was looking for something a bit more descriptive than “good.”

She was posting up-and-down on my cock, revving up for her second orgasm.  Her front teeth were biting down on her lower lip.

“Tell me more,” I implored.

“Grab my tum,” she said.

I did.  It was bouncing up and down and jiggling, just how I like it.

“Am I fat, Daddy?”

Trick question.  Was she in the mood to be fat?  Would saying yes ruin the mood?  I rolled the dice.

“Yes.”

“Fuckable fat?”

“Yes.”

“Freaky fat?”

“Yes.”

She brought herself to an orgasm.  She lifted her pussy up off of my rod to rain her cum down on me and then turn around, reverse cowgirl, and slip right back into the saddle.  I noticed as she did so that she was clean shaven.  When she left the house a few hours ago, she had a hairy bush.

She rode me as I watched her ass rise and fall with stronger and stronger strides down on my cock.  It was as if she needed more, deeper, longer, harder, thicker, fatter.

I could hear her sloppy, wet pussy slapping down and splashing on my hips.  She groaned and growled in rhythm with her own beat.  The sound grew more insistent.  She was reaching, striving for that second (or third?) orgasm, but not quite reaching it.  She pulled forward and turned around on all fours.

“Get behind me!” she insisted, as if there was no time to lose.  “Get in me and fuck me.  Fuck me hard!”

I was on my knees pounding my pelvis into her, slamming her with every ounce of energy I had.  Her head was bouncing forward into the headboard of the bed.  She didn’t care.  The new position wasn’t doing it for her.  She pulled off of me.  She got on her back and slid to the side of the bed with her legs in the air.  The sheets and blankets were soaked by now.

I stood on the side of the bed and held her ankles as I entered her pussy.

“Grab my tits,” she said.  “Pull.”  I pulled her nipples.

“Grab my tum,” she said.  “Slap it.”  I did.  I held it with my fingers like it was dough for kneading.  I slapped it.  I slapped her tits.  She grabbed my right hand and moved it to her cheek.  I knew what she wanted.  I don’t like to do it.  She slowly moved my hand in the motion of what she wanted me to do.  I followed through.  I slapped her, gently at first, across the face.

“Again!” she said.

I slapped her again.

“Harder!”

I slapped her harder.

I did this around ten times.

“Now my pussy,” she said.

I pulled out and slapped her pussy with my palm.

“Harder, faster.”

I gave her pussy about ten hard slaps.

She was frustrated.  She pushed me away.  With her legs in the air, she slapped her own pussy as if punishing it severely.  WHACK!  WHACK!  WHACK!  Until she was squirting all over the floor.  She fell backwards and collapsed in the sopping wet bed.  She passed out, leaving me standing over her, hard-up.

I walked away, went to the bathroom, washed up, dried off, and then walked to the living room couch where I went to sleep.

In the next installment – Leia and the Hutt

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Stoya’s Secret Sexual Rival

Slate Stoya Lola

Dear Readers:

Perhaps you know that Jessica Stoya, most famously known simply as Stoya, has a new sex and relationships column called “How To Do It.” A while ago Lola submitted to Stoya, that is, she sent in the following query but never received a response. Perhaps you have some suggestions for Lo.

Dear How To Do It:

Not sure if you can answer this question because it might be a conflict of interest for Stoya. You see, my man loves having sex with Stoya. That is, he loves to have sex with the Stoya Fleshlight I bought him as a gift. He and I have an otherwise excellent relationship. He is older than I by about two decades. We have a 1/2 open relationship.  With his enthusiastic consent, I’m allowed to have fun with others – men, women, with or without his presence – but he is not. He is content with that arrangement and he also knows that the reason for the lack of symmetry is because I get jealous and insecure. As a consolation prize, I got him a Stoya Fleshlight, knowing that Stoya is one of his favorite porn stars. But now he frequently asks me to hold the Fleshlight while he goes at it, kissing me but having intercourse with her. This was fine as a novelty once in a while, even if it did make me jealous, but now it’s a more frequent request and I find I’m growing insecure of her/your prosthetic pussy. But I feel conflicted because I will frequently bring myself to orgasm using my Hitachi Magic Wand (next to him or alone) and he has no problem with that. A double-standard? Yes! Can you help me sort out these feelings?

Signed,

Stoya’s Secret Sexual Rival

Lola fingering Stoya

Stoya and Synthetic Stoya

Stoya for Lola

Stoya fingering Stoya

Lola and Mr. Hitachi

He made her cum!

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