Phone Sex Series: Client #4 Obsessive Ass Man

This is the fourth real client-inspired smut piece in the Phone Sex Series. This one is inspired by a man who has been my client for nearly 10 years. His love of ass is unsurpassed.

Christopher had just graduated from high school. He found it both exciting and humiliating that he couldn’t get through a day without draining off three or four times; if he saw the seam of a tight pair of pants or shorts wedged up a girl’s ass, sometimes five times. It was an uncontrollable compulsion. His dick felt like a jug that would fill to overflowing every few hours. Denying the drainage would simply lead to uncomfortable frustration.

He and a good friend had tried to have sex once. Christopher had stayed over late at the friend’s house, and though he imagined his first time would be with a girl, he was horny. They decided a coin toss was the most fair way to decide who would fuck whom. This landed him on top. Though they used some lube, the fucking barely began when Christopher’s friend told him he was too big. He was embarrassed. So, they hadn’t tried again.

He coped with the unsuccessful attempt my swearing off people his age. He started to wonder what it would be like to be with some of his mom’s friends. He wondered if it was true that older women liked young guys with big dicks. He was curious about his mom’s friend Elisa. Her ass set him off every time. It was really big, and she loved to show it off. In the shower, he’d lather up the soap so it was just a handful of white froth. He’d get on his knees, pumping his soapy fist. When he’d first started thinking about her, he would just imagine standing behind her and watching her walk with a short little white summer dress on. Thinking about little glimpses of her ass and some black, tight ass-hugging panties shoved deep into it would make him cum really hard. Even just mouthing the words that described her ass “ juicy, plump, dimpled, fat “ could do it.

Nowadays, he couldn’t help his mind from wandering onto dirtier terrain: her mercilessly fucking his tongue with her asshole and then peeing in his mouth, getting to watch the piss trickle between her ass cheeks as he came.

Christopher’s mother had decided to leave him for the weekend. She told him that Elisa had the key to the house and that she was going to check in just to make sure that Christopher wasn’t surviving on ramen and cheetos. Christopher did not protest. He really, really hoped that Elisa would come over with one of her prick-teasingly tight pairs of workout shorts on. He imagined that she’d catch him masturbating in the shower and blackmail him into fucking her ass.

On Saturday night Elisa phoned to give a “heads up that she was planning a visit. Her voice on the phone gave him nauseating, chilly sensations. He heard a car pull up an hour later. He decided he’d stay in his room upstairs since he knew he couldn’t pull off anything impressive or successfully seductive. The possibility that she might walk up the stairs to talk to him was keeping his dick rock hard underneath his blankets.

It felt like she was downstairs forever when she finally called up to him. When she got to his door, he saw that she had come straight from the gym: white tank top, sports bra and a tiny pair of biker shorts. She came right in. He could see her ass in the mirrored closet door in front of his bed. He watched the movement right where each cheek met the back of her legs. The curvature of that bubble made his mouth water. She sat next to him on his bed and began asking him politely mundane questions about his graduation and his summer plans. During one of his responses she just pulled the blankets down and uncovered his huge erection through his pajama pants. His inclination was to grab the blanket back, but he couldn’t move.

“What is that? she asked accusatorily.

He shook his head.

“Christopher, is that an erection? Again it felt like an accusation. He knew that he was going to get in a lot of trouble, that Elisa was going to tell his mom, that he was going to have to explain to her that he was a terrible person with an unruly pervert cock.

She grabbed his dick roughly through his pajama bottoms. His mouth opened in shock, horror, arousal, amazement, disbelief. “Did I give you this big erection, Christopher? I need you to tell me right now or I’m calling your mom.

“Yes.

“Yes what?

He didn’t know what she wanted.

“Tell me what I did to you, Chris.

“You gave me a big erection.

With one hand still on his cock, she reached down and grabbed his journal. It had been sitting on the floor. It was filled with all of the dirty shit that he wanted Elisa to do to him. She made him pull his dick out and show it to her as she read it. She made him confess all his fantasies while he stroked his pre-cum covered dick up and down.

“I can do whatever I want to you can’t I, Chris?

He nodded. “You can do whatever you want to me, Elisa.

“And if you don’t do what I say, I’m going to tell your mom that you misbehaved. Do you want to know a secret? A long, long pause while she looked at Christopher’s eyes. Your mom knows about this. She said I could do whatever I wanted with you.

He imagined his mom and Elisa negotiating all this, Elisa telling his mom that she’d wanted him for a while and was just waiting until he was old enough.

She told him to stand up, and take her clothes off. First her tank top, then her sports bra. He peeled off each thing. They were clinging to her skin with the sweat from her workout. Once she was topless, she pushed him down on the floor and straddled his head. Her pussy was right in his face. She wasn’t wearing panties. He could smell her pussy and see some of her pussy hair through the stretched baby blue fabric of her shorts. He wanted to touch his dick so badly.

“Stick your tongue out and rub it all over my cunt. Get my shorts really wet. If you do a really good job, I’ll make more of your nasty fantasies come true.

She did. She sat on his face. She force fed him her ass hole and made him tongue fuck her, flexing and releasing her ass hole, sucking his tongue in and then pushing it out. She took pictures on her phone of him stroking his cock and serving her ass hole. He loved the idea of being used in this way. He loved the idea that she might use these photos to blackmail him into doing more and dirtier things. She pissed in his mouth. She held him down and finger fucked his asshole. He was so turned on he was gasping and begging, nearly unconscious with arousal. Finally, she got on her elbows and knees on top of his bed, her ass up in the air. She turned and looked at him sternly, “Fuck my ass hole. I want your virgin dick in my ass. Do what I say. She slid down, cheek to mattress, reached her hands back and spread her ass. Her ass cheeks filled each of her hands, leaving gorgeous hand prints on her fleshy butt. The sight of her cheeks spread with her hot asshole exposed made his dick drip and ache. She let go of one of her cheeks to grab his dick and push it against her asshole, guiding it in, looking at him with her lips parted.

Once his big dick was in her ass, he thrust deep and hard. He grabbed her wrists and lifted her tits off the bed, filling her ass to the hilt. She made him do everything so that she could cum over and over and over.

After that night, Elisa invited another friend and then another until Christopher was serving the asses of the entire MILF population of his little town. Elisa would often guide his dick into the eager ass holes of her girlfriends, but at the end of the night it was always her asshole that got the most eager servicing and the biggest load.

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Virgie Tovar

Virgie Tovar is the author/editor of the upcoming fat positive anthology Hot &Heavy: Fierce Fat Girls on Life, Love and Fashion (Seal Press, November 2012). She holds an MA in Human Sexuality, is certified as a sex educator, and was voted Best Sex Writer by the Bay Area Guardian in 2008 for her first book, Destination DD: Adventures of a Brest Fetishist with 40DDs. After teaching Female Sexuality at UC Berkeley she went onto host The Virgie Show (CBS Radio) from 2007-2008. When she’s not teaching sexuality seminars or shimmying as her burlesque alter ego, Dulce de Lecherous, she is creating content for her video blog: Virgie Tovar’s Guide to Fat Girl Living. Virgie has been featured on Playboy Radio and Women’s Entertainment Television. She lives in San Francisco.

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