Double or Nothing

by Paris Waterman

Copyright© 2018 by Paris Waterman

Erotica Sex Story: They've split up, but then he gets a late night call begging him to come over. She 'has this problem' and only he can help with it.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Anal Sex   Oral Sex   .

A Chastened, FL Tale

Call them star-crossed lovers if you will, but Steve and Gabby had this on again, off again romance that left their friends and even closer friends baffled. Steve had presented Gabby with a knock your eye out engagement ring that cost him the price of a Dodge Viper two years earlier only to see Gabby storm off in a huff a month later without giving him or anyone else a reason.

Six months later, at a Christmas party celebrating the holidays and the closing of Annie Get Your Gun in which Gabby had one of the principal parts, they hooked up again. This revival barely outlasted the musical’s run of two weeks before dissolving once again, without any discernible rational for its dissolution. Gabby did keep the engagement ring, but refused to take any of Steve’s calls.

Steve gave up on her and a full year passed before he heard from her again. It was Alexis Dubois, his best friend Charlie Daly’s fiancée, who texted him at eleven-thirty on a Wednesday night. The text was short and concise in Steve’s eyes: Alexis said that while she was aware of his estrangement with Gabby, she thought he would want to know that Gabby was almost desperate to see him again and would be calling him shortly. Alexis added that she thought it imperative that he take the call.

My estrangement! Steve thought, my fuckin’ estrangement! I’m not estranged ... I’ve been fucked over twice. I’m a two-time loser and not about to join the three time club wherever the hell that is!

Steve made himself a strong vodka martini and was pouring the remainder of the drink into his glass when at 12:01 his cell signal went off.

Who the hell... ? He asked himself as he looked at his phone but didn’t recognize the number. He answered it anyway.

“Hi Steve ... it’s Gabby.”

Steve spit the vodka from his mouth onto the carpeted floor.

“Don’t ... don’t hang up! Please don’t”

When he failed to respond but did not hang up, Gabby went on. “I hope you’ll hear me out...”

She heard him breathing into the phone and plunged ahead. “I want you to know that I still have feelings for you. I ... I want ... I hope we can be friends.”

“Stop right there,” Steve said after finding his voice. “You’ve fucked me over twice now. Never bothered to give me a reason why you dumped me. I spent a fortune on that so-called engagement ring. In fact, I’m still making payments on it. You didn’t bother returning it as most women would, especially when YOU broke it off.

“Now you call me up at midnight saying you want us to be friends? What the fuck is wrong with you? I don’t want to be your friend. I want that goddamn ring back! You can send it FedEx tomorrow ... I mean, today since it’s already tomorrow. Oh shit! I don’t know half of what I’m saying!”

“Steve—Steve—Steve! Please forgive me. I—I’ve had some issues, you know?”

“No, I don’t know, Gabby. Issues are something normal people ... people who are engaged to be married usually try to discuss. I don’t recall any discussion whatsoever.”

“Didn’t Alexis tell you why I was calling?”

“No she didn’t. All she told me—and that was in a text—was that you were ... you wanted to see or talk with me.”

“I do--Please hear me out!”

“Yeah—yeah, but hold on while I freshen my drink. I think I’m gonna need it.”

“Okay, I’ll hold...” There was a definite forlornness in her voice.

Gabby could hear that he was indeed making a drink for himself. The clinking of ice against a glass provided that important piece of information to her. Important because she was afraid he was just leaving her hanging on the phone and walking away.

“Okay, I’m back. You go and you better make it good or I’m hanging the damn phone up.”

“Okay ... thanks I really appreciate your listening to my side of the story.”

“Yeah, well, there’s only that side to hear as far as I’m concerned.”

“I understand, Steve. I really do. You see, I have what’s called Avoidant Personality Disorder. It’s, um, an affliction in which I um, become uneasy or anxious or lonely or unwanted and isolate myself from others.”

“Avoidant Personality Disorder?”

“Yeah ... it um, manifested itself during my early childhood, but I didn’t know it. I mean, I knew something was off base about me, but had no idea what it was. My parents didn’t see it either. As I understand it from my shrink, I um, consider myself to be personally unappealing and tend to avoid social interactions for fear of being ridiculed, humiliated, rejected, or disliked. Apparently, my parents had considerable difficulty with their own negative emotions.”

“And you never brought it up? I mean, we met, we broke up and then repeated the process again. Now you’re telling me this and all that’s good, but what is it you want? I mean, you can’t expect me to pick up where we left off back then.”

“Well, yeah ... kinda.”

“What’s that supposed to mean, Gabby?”

“Um, I’ve been working on this ... problem for some time now.”


“Please, Steve, this isn’t easy for me.”

“Sorry, go on, tell me. Take as long as you need.”

“Thanks, I appreciate that. As the name suggests, the main coping mechanism for those with my personality disorder is the avoidance of feared stimuli. I um, didn’t notice this disorder until we got engaged. I mean, within hours of putting your ring on my finger I was wallowing in despair. I just knew you were going to reject me. I know—I know, you’d proven your love for me by giving me this gorgeous engagement ring and I went off the deep end, well at least as far as you’re concerned. Have I got that right?”

“The deep end? Yeah, it was as if you’d pole-axed me.”

“I’m not sure what that means, exactly, but I get the gist of it. At any rate, after extensive analysis, I’ve learned that I harbor thoughts that ... well in our case I started feeling unworthy of our relationship, and I distanced myself from you. You could say that I just took flight, which on reflection is exactly what I did.”

“Gabby, if you felt that way, I mean, unworthy and all, why did you make up with me at the Christmas party? I mean, Jesus, you had broken up with me and then out of the blue you show up and act like nothing’s happened between us. And I, sap that I am, welcomed you back with open arms for all of two weeks, and then you were gone again---and no reason given.”

“I am so sorry, Steve.”

“And then I’m bothered by the fact that you can get up on the stage and perform one of the leading roles in a musical and still be mentally crippled by this Avoidant Disorder. I don’t understand. Even your friends, Alexis and Holly couldn’t, or wouldn’t give me a reason. They both claimed they didn’t know why you broke it off with me.”

“They didn’t know, Steve, I swear to God they didn’t.”

“Do they know now?”

“Alexis knows some of it. Holly and I ... well, we haven’t talked in months.”

“Why now, Gabby? I think that’s a reasonable question. Will you answer it?”

“I’ll try to Steve. I’ve learned that I ... that I’m preoccupied with my own shortcomings and am able to form relationships with others only if I’m convinced that I won’t be rejected. My problem has been and to some extent still is that I’d choose being alone rather than forcing myself to reconnect with you. Let me assure you I’ve held myself in contempt all this time for treating you the way I did. That’s why I tried to reconnect at the Christmas party. But I couldn’t handle it. I wasn’t ready to fight the battle with all the unresolved angst at that time.”

“Sounds like you’ve been through hell,” he said and for the first time felt a pang of sympathy for her.

“Yes, well ... my guess is that you have too, and for that I’m so very sorry,” Gabby replied.

“My doctor,” Gabby paused and Steve felt that she was smiling over the phone, “tells me that I’m very much in love with you. Um, that’s why ... well that’s one reason for this call. I agree with her. My feelings for you are as strong as they were when we got engaged. But I understand how you must feel about this too and if you want to call it off I’ll understand.”

“Just a second, Gabby. I don’t know how I feel about ... us. But I’m willing to think about it.”

“Do you want the ring back? It must have cost you a fortune.”

“Had it appraised did you?”

“I did. I was shocked at its value.”

“I’ll take it back, but I want to meet with you first.”


“Yes I do.”

“I could come over now if you want me, Steve.”

Steve glanced at his watch. “Its 12:45 Gabby.”

“I know,” she said, and he heard the hope in her voice and was deeply moved.

If what she’s telling me is true then she’s gone through a worse time than I have. I think I owe her the chance to redeem herself. Hell if I can help her recover, or even grow to accept her ‘condition’ it would mean a better life for her.

“But I can be there in fifteen minutes, give or take.”

There was urgency in her voice that he hadn’t heard from her before.

“Fifteen minutes?”

“I promise I’ll hurry!”

“No—no, take your time, but do come over. We need to say some things face to face.”

“Yes, we do ... I do. I love you and I’m on my way!”

Seventeen minutes later, yes, Steve counted them, Gabby arrived. She seemed thinner now than she had the last time he’d seen her. The weight loss made her C-cup breasts appear even bigger to him and her dancer’s legs were still world class compared to anyone else’s. Gabby’s brown eyes were definitely deeper and perhaps brighter than he remembered, but her shy smile still lit up the room; only now he knew why it was shy and not gregarious like most women he was acquainted with.

Gabby wasn’t dressed to kill as she usually did when going out on a date. She wore jeans that accentuated her rear and a light sweater that did the same for her breasts along with her heels.

“Can I have a hug?” she said after entering the apartment.

“Oh, yeah ... sure,” Steve replied and quickly embraced her, luxuriating in the pressure of her breasts against his chest.

As soon as their embrace ended, Gabby fumbled in her purse before producing the engagement ring. “Here, I promised it to you. Please take it!”

“Gabby, you don’t...” But he accepted the boxed ring and placed it on a nearby table.

“Thanks, I guess. You—um, you look good.”

“You too,” Gabby said looking him directly in the eye.

“Another hug?” Steve said so hungrily that Gabby backed away from him and into the wall behind her.

“I don’t know,” she said as her back hit the wall and she stared at him wide eyed. Steve moved with her, his hands splayed on either side of her head, framing her face and her hair as she looked back at him, breath quickening in her throat. He leaned closer, looming there for a long moment before slowly backing away enough to let her breathing slowly return to normal.

“I want to, Steve, at least a part of me wants too. Do you understand?”

“Fuck no! I’m confused. I thought you came over at this hour for one thing.” He grabbed his crotch to signify just what he had in mind.

“Can’t we be friends first, Steve? Friends with benefits?”

He was obviously confused. Why had she backed away from him if she wanted to fool around?

“Steve...” there was no mistaking the quake in her voice. “I haven’t been laid since the last time we did it.” Then she saw the need to add: “I’m one horny bitch. I know I’m a fucked up weirdo, but I need you in me, Steve. I mean, why else would I be calling you up at this hour?”

“That was a while ago, Gabby,” he replied softly, recalling that night and how they’d fucked.

“I know” she whispered helplessly, coming back into his arms and kissing then nibbled at his jaw and ear before and exhaling moistly into his neck.

“I know...” she whispered again and sighed, letting her head rest on his chest for a moment.

Steve caught her hair and pulled her face up to meet his lips, his hungry lips. Ending the kiss, he looked into her eyes.

“Gabby—Gabby—Gabby, he sighed then shook his head once before shrugging and mashing his mouth down upon her plum colored lips. He put everything he had into a series of long French kisses that generated a cloud of steamy lust throughout the room.

Gabby responded by raking her nails over his t-shirt covered back, pulling it out of his jeans, and then lowering her hands to fumble with his fly while moaning impatiently into his mouth.

Steve’s hand went between her legs and using the edge of it rubbed hard against her genitals.

“CHRIST THAT FEELS GOOD!” She moaned, and opened his belt then pulled his jeans down to his knees.

He squeezed her labia and she nearly bit his tongue in her excited state.

“Too many barriers ... let’s just get naked, Steve!” She mewled with frustrated need and want.

His cock was out and pointed upward.

He stepped out of the jeans and nodded at her.

“Show me your tits, Gabby,” he said lewdly, driving her keyed up state ten degrees higher.

Off came the sweater. Off came the bra. Gabby quickly wriggled out of her jeans then removed her thong.

There stood her twin peaks, glorious in their splendor, quivering in their unspoken need to be bitten and sucked and squeezed. Steve didn’t touch them. But after a long wanton look he reached down and picked her up just like that. She wrapped her legs around him and there he was halfway inside her just like that.

I could hold her ass in my hands and fuck like crazy, he told himself. He paused for a long moment to savor her silken warmth and to allow her to adjust to his girth before walking her back against the apartment wall while edging fully into her; smiling as she gasped at the feel of him inside her again.


“Ready, Gabby?”

“Yes, Steve!”

He paused a moment to let her welcome his girth once more and as he did he recalled previous times with her and how she’d reacted to it. Gabby’s always had a thing my how thick my dick is ... other women like it but tell me to go slow. Gabby loves it when I slam the meat to her ... I wonder?

He repositioned her against the wall and then braced himself to keep her there and sent his dancing tongue into her mouth while his cock pounded away at her pussy.

And as he did, the pent up anger and frustration at her dumping him seemed to lift away and he felt lighter somehow. Then there was just a sexual bliss. Gabby felt it too, and it was good. It was better than it had ever been before.

She grunted, “HUH”

He fucked harder.

She met him with equal force and they both saw stars when Steve lifted her up, spun away from the wall, and walked them both to the couch where he set her on her feet.

“Jesus, Steve!” Gabby managed to blurt before he covered her mouth again and kissed her for the longest time.

And still they fucked; although at a much slower pace before he decided to push her backwards onto the couch.

Gabby moaned into his mouth when her clitoris rubbed across the nubs of his pubic hair. She spasmed and screamed joyfully when his cock grazed her g-spot and brought her to the first of her orgasms that night.

Steve felt himself clench and willed his pending orgasm away in order to give Gabby another one before he went dry. She laughed and stroked his head, saying: “You made me cum! You made me cum!”

“Want another?” he asked.

“YES! YES! And YES!”

Steve’s mind ran wild conjuring up perverted possibilities he could have with her dynamite body. “Suck me off first.”

Gabby pushed her hair back over her right ear and lowered her head down to accept his rigid member into her mouth. Steve felt a strange sense of surrendering his power over her as her mouth sealed itself around his shaft. She had always given good, if not excellent head, and this time was no exception. No sooner had his phallus entered her mouth, Gabby managed to gobble most of his thick manhood without gagging.

“Mmffph!” she gulped, swallowing some of the excess saliva that had built up while she sucked him.

He tried to suppress a moan but failed. The corners of her mouth pointed up a bit, and her eyes met his as she smiled as best she could with a mouthful of cock. Then she slowly pulled her head up, causing his dick to slide round her mouth, tongue and teeth until it left her mouth completely. Gabby took a deep breath and took him back down her throat again.

Knowing full well Steve was close, Gabby’s head bobbed up and down on him; her lips and tongue expertly applying pressure against his shaft as she fellated him.

Steve gripped the sheets and managed to keep it together, simply moaning while his ex-fiancée sucked him off. Gabby kept one hand at the base of his dick, rubbing his pliable testicles while coating his shaft with her saliva with the other. Her hair shifted back and forth as her head moved up and down, on the upper portion of his cock; jerking him off with the hand that had been wrapped around the base moments before. Every few seconds, Gabby slowed down to lick the tip while looking up to meet his eyes and then going back to town on his glistening cock.

Steve lasted another two minutes before Gabby pulled away and straightened her back. She sat up, licked her lips a bit as she looked down at his reddened twitching manhood, and then smiled. In that moment, at least for that time, Steve forgot about all the pain and worries she had caused him since their shattered engagement and exploded sending rope after rope of his boiling cum at her. Most of it landed exactly where she wanted it too—on and between her formidable breasts, with a goodly amount also winding up on her hands and right wrist.

“I’m still mad at you” Steve growled as he allowed her to take his deflating cock back into her mouth and cleanse him properly.

“Are you allowed to have any alcohol?” he inquired after having her sit down on the couch.

“Sure, why do you even ask?”

“I thought with all the doctors you’ve been seeing...”

“Oh ... well no, no one’s told me I can’t. I mean, I don’t drink all that much.”

She laughed self-consciously. “That isn’t my problem, or even part of it. So if you’re offering, I’d love a drink. Anything you’re having is fine by me.”

As Steve mixed them both a drink, Gaby watched him, actually she devoured him with hungry eyes, and then said, “Remember the showers we used to take together?”

He turned and smiled at her. “Yes, I do.”

“Mmmm, I used to love the intimacy the cramped quarters provided. Christ I would get crazy horny looking at your cock. You have the loveliest cock, you know? I love the way it bends to the left and its girth---Jeez, it must be about 6 inches ... I think I compared it to an old Nehi soda bottle once. They were almost the same circumference. I mean, you’re cock is as thick as most guys are long.”

“You think?” He said, somewhat amused and definitely flattered. Most female partners he’d had didn’t comment on his cock size one way or the other.

“Oh you better believe it. And I loved kneeling in the hot spray, gulping down your cock and swallowing your load, nearly drowning in the cascade of water over my head as you shoved that whopper into my mouth. Christ, Steve, I’m getting wet just talking about it.”

“You always pretended you weren’t interested,” Steve said.

“I did, didn’t I?”

“Yeah, you’d say something like: ‘We can’t, not now. I need to finish rinsing my hair,’ or some other bullshit lie.”

Gabby laughed lewdly and said, “Then you’s ask me so nicely if you could just jerk off against my ass.”

“I always called it your lovely Irish ass,” he laughed.

“You did, didn’t you?”

Steve wondered for a moment if she hadn’t actually recalled those moments of their past until he brought them up. Or was she just going along with him and not really recalling them at all?

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