Blackmailing Gina Ch. 01 – Anal

“A Blackmail Attempt”

I met Gina when I took my mom out to eat. She was our waitress, and she was beautiful.

Think of a cross between Demi Moore and Salma Hayek. She had the most gorgeous big brown eyes, haunted and damaged, but still cautiously hopeful. And something about her full lips and mouth, even with a space between her two front teeth, made hers the sexiest mouth I had ever seen.

We hit it off immediately, joking and talking non-stop to each other. My mom even made a opinion that we should just exchange numbers so she could relax and enjoy her meal in peace.

I didn’t ask for her number. Instead, I started hanging out in the bar attached to the restaurant where she worked.

We played pool, hung out and really got to know each other. Every guy in that restaurant and bar made passes at Gina, but she wasn’t interested in anyone, it seemed, so I played it cool.

Then, about a month later, Gina confided in me that she was trying to break up with her daughter’s father. He was a crack addict, and their daughter was only two years old.

That’s when I confessed how attracted I was to her. I told her I’d like to remain friends even if she wasn’t interested romantically, but I was all in if she was.

At closing that night, she invited me to a friend’s house for drinks. We ended up kissing in her friend’s bedroom.

After that, we had a very hot two or three week affair, and really couldn’t get enough of each other.

It was 1992. So, I was 28 and Gina was 25.

Around two or three weeks in, having Gina sleep over my house every night, a very bad thing happened that last night in my house.

Gina confessed to me that she was also hooked on smoking crack, and had been for more than a year.

She told me that after not having a hit for so long, that she had to leave so she could go get high. She also said that she would have to have sex with her sugar daddy to get enough money for the crack, and she needed to smoke it with her ex at his house, so she might have sex with him, too.

I was devastated. She said she’d find out if I never wanted to see her again.

My first reaction was to beg her to go to rehab. She flatly rejected the idea.

Then, knowing I was fucked because I was already hopelessly in love, I told her I would let her go, but I wanted her to come back to me.

She thanked me, and cried as she left.

Letting her go that night was one of the most painful things I have ever done, but she was so honest about it I didn’t resent her for it.

She came back to me two nights later, admitted that she had sex with her sugar daddy, and gave her ex a blowjob.

I forgave her and made love to her that night. We had another great week or two together, and she told me she had to relapse again.

This happened half a dozen times over the course of three or four months. I forgave her and took her back every time.

She didn’t all the time have sex with her ex, but Gina all the time had sex with her mysterious sugar daddy.

She talked all about her ex, but would never divulge the identity of her sugar daddy. One time, as I was asking about the guy, Gina shut me down by saying, “Nobody can ever know who he is, and he will never tell anyone who I am. We will take that secret to our graves.”

The only thing I knew was that he was an older white guy, and had accidentally gotten her pregnant a year before I met her, but he paid for an abortion.

His identity gnawed at me. Gina had been fucking this one guy to support her habit to avoid working the streets or fucking drug dealers, but she wouldn’t tell anyone who he was.

Well, one fateful night, after Gina informed me she had to leave to get high, I followed her with my car and my video camera.

I wanted to see who she was meeting. I pictured someone popular, a politician or a news anchor.

Gina drove to the parking lot behind Kent County Hospital. She backed in to a parking space way out near the woods. Another car was parked there, too. She had pulled in beside it.

I couldn’t approach them with my car. They would see me coming from a hundred yards away, so I pulled up next to the woods on the far side of the lot from their cars.

I got out of my car and hiked on the edge of those woods until I was within twenty feet of them.

Gina was fucking a man in the back seat of her car. I turned the video camera on, and luckily, they had parked under a streetlamp.

You could make both their faces out as they fucked.

The man who was fucking her, to my shock and surprise, was Gina’s stepfather. I had met him and her mom several times before.

I kept filming.

It was obvious they were fucking, even at night and from a distance. I zoomed in and also noticed that Gina wasn’t exactly distraught or crying about it.

Actually, she looked quite into it.

They finished up and I saw Bobby handing Gina cash. She French kissed him goodbye and drove off to go buy her drugs.

I left and never said another word about it.

Gina got clean soon after that and we had a rocky eight year, on and off again, relationship. This was not due to drugs. 

She had stuck with the program the whole eight years, but she cheated on me five times.

She would be completely honest about cheating, but all the time break up with me after she cheated.

This drove me insane. She would blame her cheating on how I treated her or claim we weren’t really together as a real couple when she cheated, anyway.

There was all the time some excuse that excused her infidelities.

Then she would date the turd she had cheated on me with, and all the time come back a few weeks or months later, telling me she was sorry and begging for me to forgive her.

These were the only times she would ever say how much she loved me.

I loved her too much to withstand.

On top of that she was so frigging beautiful, and we had such amazing sex that I could never turn her away.

Gina was never squeamish in bed. She loved every hole filled, and enjoyed drinking cum.

Girls that gorgeous are rarely that wild in bed.

She had a fetish for brutally rough anal sex that was so off the hook I probably would have been obsessed with her for that alone.

More on that later.

First, you must find out this, I have a cum swallowing fetish. No. Not me swallowing.

When a girl drinks my cum I am thrilled. It probably stems from an experience I had when I got my first blowjob. (See *Two Lonely Women: Ch. 1, on Literotica, by me, Hofeeder.)

Gina, according to her, hated the idea of swallowing cum and had never done it before we met.

Well, after Gina would leave me to get high and have sex with her sugar daddy and her ex, when she returned she would try to make it up to me by learning to swallow my cum.

This was massive. I could tell it was difficult for her to do, but she would power through it and swallow anyway.

It was so exciting for me, especially because of how much I ejaculated. Most girls who had no issue swallowing cum had problems with mine. It was just too much for them to handle.

Having Gina devote herself to learning how to cope with swallowing my copious amounts of semen helped make me obsessed with her.

Also, I adored her personality, and really enjoyed spending time with her.

Lastly, she was the most brutally honest girl I ever met, and I appreciated that. Her excuses for cheating were complete bullshit, but she all the time confessed that she cheated without me prompting her, and would convey every detail if I asked.

In the end of our eight year run, however, after Gina got her bachelor’s degree, she cheated on me with a doctor and it finally stuck.

She dumped me in the summer of 1998, and I was heartbroken.

A few months later, I heard through a friend that they were very much in love, buying a house and getting married.

I called Gina that night. When she answered I congratulated her and told her I needed her to come to my house for a few hours to talk about something so crucial that it could change her life.

She refused to see me in person.

“Gina,” I said, “It’s about your secret sugar daddy.”

The phone went silent.

“What about him?” she asked.

“I know who he was.”

“Harry, nobody knows who he was, and nobody ever will.”

I said, “It was Bobby, your own stepfather.”

She laughed a little too loudly, and said, “Don’t be ridiculous.”

“It was Bobby. I have a video tape of you two fucking.”

“You are fucking insane and disgusting. I can’t believe you would make up this elaborate–“

“I followed you, way back when, right after we started dating.”


“So, I taped you fucking him in Kent County Hospital parking lot.”

The phone went silent again.

“I have the tape. You can come and watch it at my house… while you blow me, of course, and drink all my cum.”

She screamed, “What? Excuse me? I am not fucking coming to your house or ever fucking blowing you again, you sick, twisted, motherfucking bastard! If you think I would ever–“

“Then I mail a copy to everyone you know, and I have about twenty copies.” I hung up the phone and waited, staring at it.

Several minutes elapsed, and I got more and more chagrined.

I walked to the fridge for a beer, completely puzzled. “She’s got to call,” I muttered.

Popping the cap, I took a long swig. Then I sat down by the phone, watching that video tape on TV, and I waited for her call.

About ten minutes later, a car sped into my driveway and screeched to a halt. I heard stomping footsteps and then it sounded like someone was trying to beat my door down with their fists.

“Open this fucking door you sick fuck! Open it!”

Gina lived almost twenty minutes away. She had made the drive in about twelve.

I went to the door as she continued to pound on it and scream for me to open it. I shouted, “Only if you calm down!”

She must have kicked it. My heavy wooden door cracked. Knowing it wouldn’t break, I said, “If you don’t fucking calm down I am calling the cops.”

She stopped beating on the door. Out of breath, Gina shouted, “Open up, you filthy fucking liar. You don’t have any tapes. It’s just a pathetic and stupid bluff. I don’t even know why I got so mad.”

“It’s playing on a loop in my VCR right now.”

“Then open up and prove it.”

“Do you promise not to hit me?”

She laughed, “What are you afraid of a fucking girl, you fucking pussy?”


Gina cleared her throat, and snickered. In a calmer tone, she said, “Just open up, Harry. I won’t beat you up. I wanted to, but I’m calm now.”

I unlocked and opened the door.

She glared at me. “Why would you make something like that up?”

I moved apart, giving her a clear line of sight to my TV. “I wouldn’t.”

Gina spotted the video playing. It was a clear shot of her and her stepfather’s profiles as they fucked in the back seat of her car.

Her mouth dropped open and her eyes nearly popped out of her head. She walked quickly past me toward the TV.

“Fuck. Fuck. No. Fuck.” She stopped and stared at the screen with both hands on the top of her head.

It was getting to the part where both were about to orgasm, or at least each appeared to climax.

Bobby went first, his face contorting and his body shuddering as he thrust his hips upward.

Gina, who was riding him, was pushed up, the back of her head and shoulders pressed against the roof of her car. Then, her mouth opened and her body quivered.

I had watched it a thousand times.

The Gina in my house spun around to face me. Her mouth moved, but nothing came out. Then she shrieked, burst into tears and covered her face with both hands.

She fell to her knees like that and wailed, almost incoherently, “Please, Harry! You have to burn it! Burn it, now!” Her whole body shook as she sobbed violently into her hands.

I felt horrible. Walking over to her and rubbing her shoulder, I said, “Do you need some water, Baby?”

She shook her head, and removed her hands. Tears streaked her face and a tear droplet hung from her nose. She looked up at me, took a few shaky breaths and said, “You knew this whole time?”

I nodded.

She almost lost it again, but maintained control. “You must… You must think I’m disgusting.”

“No. I love you, Gina. I think you are amazing.”

She sniffled, wiped her tears away with her hands and shook her head. She blinked a few times, looked up at me and said, “If you really loved me you would destroy every fucking copy of that tape.”

I smiled and said, “That would be very unselfish love, wouldn’t it?”

She nodded, a hopeful look in her eyes. “Yes!” she said, “Yes, it would.”

“Do you think cheating on me with five men, that I know of, and then dumping me for a doctor was unselfish love, or selfish love?”

She looked up at me, a snarl forming on her pretty upper lip and her brow knitting in anger.

“I almost mailed it to your fucking mother without even calling you.”

Eyes widening, she inhaled sharply and held her breath. The anger gone, Gina’s face turned to stone. 

“What? No, thank you?”

She blinked her eyes and exhaled, shaking her head as if at a loss on how to respond.

“Well, I think not sending it out to anyone for a week deserves a nice, sloppy blowjob.”

I unbuttoned and unzipped my jeans, yanking them down to my knees, along with my boxers.

My dick was already hard in anticipation. I had been wanting to do this to her since she fell, blubbering to her knees.

My dick popped up and wagged in front of her face.

Her eyes opened wider. She looked up at me in disbelief, and said, “You cannot be fucking serious?”

I nodded and gave her a rueful chuckle. “You are going to give me one blowjob every week for life, until one of us fucking croaks… or I will start mailing those tapes out. You can get this week’s blow job done right now… since you’re already down there.”

“Really?” She laughed and shook her head. “You really thought this insane and ridiculous fucking blackmail plan could work?”

I shrugged. “It was a long shot, but I figured it wouldn’t hurt to ask… before just mailing them all out.”

“You are serious! You really thought I would cheat on my fiancé on a weekly fucking basis just to stop you from embarrassing me? You are truly a stupid fucking man. Truly stupid.”

Gina stood up, pointed her finger in my face, and said, “If you send anyone I know a single one of those fucking tapes I will fucking shoot you. Do you understand?”

I half chuckled. “You think dying scares me?” I nodded at my desk and my.45 sitting on it. “Go grab my gun. It’s loaded. The safety’s not even on. You can shoot me right now. I try almost every night. Haven’t had the balls to shoot.”

“Okay,” Gina said, “I’ll do you that favor.” She pushed past me and lifted the pistol.

Here it was, my true plan all along. I exhaled and said, “Better aim for the head. You already ripped out the heart.”

Gina turned, lifted the gun and pointed it directly at my head. I truly expected to die. This was no joke. It was the perfect way to go, shot by the woman who broke me.

Gina had a terrible temper, and a very scary violent streak. She had beaten me with a lamp once and ended the beating by breaking it over my head.

To be honest, I wish she had beat me up like that more than just once. It had led to the best make-up sex of my life.

I held my breath, waiting for her to end my misery.

Her face turned to stone, as her finger fidgeted on the trigger.

“Well? What are you waiting for? I’m going to mail those fucking tapes and show everyone how you fucked your own stepfather.”

She took in a sharp breath, blinked and aimed the gun lower, at my chest.

I scoffed and shook my head. “Of course. That’s where you get me every time. Right in the heart. Finish the job.”

She lowered the gun a little, shook her head, and took several breaths. “I will,” she said. “I will do it, Harry.”

She raised the gun up to point it at my head again.

I shuffled forward, my pants still down around my legs, and slowly leaned in, pressing my forehead against the barrel.

Her eyes widened. She took several short, sharp breaths, and held in the air.

She set her jaw, grimaced and began squeezing the trigger.

I sighed in surrender, and closed my eyes. The last thing I would feel was a single hot tear running down my left cheek. I don’t even know why it fell.

I had wanted this for so long.

“God damn you!” Gina said, throwing the gun across the room.

I opened my eyes, let out a breath I didn’t know I’d been holding and blinked at her. “I don’t get it?” I said. “Why didn’t you shoot me? I’m fucking blackmailing you.”

“I just… I just can’t,” she said, shrugging. “Mail them out… if that makes you feel better.”

“Dying… dying is the only thing that would make me feel better. Without you… I just want to die.”

“You wanted me to shoot you,” she said, exasperated.

I nodded.


“I can’t live without you, Gina.”

Gina shook her head. She frowned and shrugged. “Sorry. I’m with Mike.”

I growled in frustration, tears falling. “You should have pulled that fucking trigger. Why do you always… always… just want me to suffer?”

She put her hand on my cheek. “I don’t want you to suffer. I never wanted you to suffer, Harry.” New tears welled up in her eyes. “But I know how much I made you suffer.” She nodded. “I really do. And it was a lot… a fucking lot… over these past eight years.”

She wiped her own tears away with her other hand, sniffled and shook her head. “Whew,” she said,  flashing a smile. “We’re both doing a lot of crying today.”

Gina cleared her throat, stood straighter and shook her head again. “Let’s get back to the business about these tapes.”

I shrugged and shook my head, ready now to just let her go. “I’ll do the unselfish thing, of course, Gina. I’ll destroy them all.”

“No,” she said, “That’s unacceptable.”

Confused, I grimaced and said, “Unacceptable?”

“Mike has classes every Saturday morning, but I’m off Saturdays. I can be here around 9 AM. Is that okay for you?”

“For what?”

She smirked, raised a brow and tilted her head, waiting for the light to dawn.

I asked in complete disbelief, “You mean for the… the weekly blowjob thing?”

“That was the terms for my blackmail, wasn’t it?”

“Are you… are you fucking with me, Gina? Or are you actually being serious right now?”

She took a deep breath, and sighed in resignation. “I cheated on you for years. Maybe it’s time I cheated with you.”

With a mischievous smile and a shrug, Gina stared into my eyes as she dropped slowly to her knees. “I can get the first blowjob out of the way right now… since I’m down here.”

She opened her mouth wide, and turned her attention to my penis, hanging only a few inches in front of her face. With a quick lunge forward, she greedily took it all into her mouth and suckled it.

I gasped loudly at the warmth and bliss of Gina’s mouth around my cock.

My soft member immediately responded to its favorite place to be. She moved her head in a bobbing and nodding fashion, coaxing my cock to get harder and harder.

As it reached its full length and girth within seconds, Gina said, “Mmm-mm,” so loudly that it vibrated my penis.

She pulled her mouth off, looking up at me as she slowly stroked my cock with her hand, and said, “I’m required to swallow all your cum, right?” Pursing her lips and squinting inquisitively, she asked, “So, what’s the penalty… if I miss a drop?” She shrugged and smiled. “I mean there has to be a penalty, right?”

“I guess,” I said, enjoying where this was going.

“May I make a suggestion?” She looked back to my cock, quickly engulfed it with her mouth again and sucked on it, delivering half shaft strokes with several bobs of her head.

I gasped, and breathlessly said, “Sure… what’s your… what do you suggest?”

She went deep, nearly taking in the whole length of my cock, her nose almost touching my pelvis.

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