Jerkboy Life Ch 08

"How did it go with Suzy the other night?"

My vivacious blonde wife Sarah was interrogating me while I did some morning worship strokes before her bald, plump pussy.

"I came, and it wasn't ruined. I'm sorry."

"That's okay. You've still got a hard-on for me, babe. No squirting for while, though, until I decide. I'm supposed to be supervising you." Sarah smirked at me and moved one hand down to slightly pull one side of her labia. Just a little, just enough to flash me her cute pink clitoral bud.

"It must have been special. Suzy's pretty strict. What happened?"

I sat cross-legged on our bed and tugged myself while Sarah spread before me, propped up on pillows. Other couples chat over morning coffee, I suppose. "She ordered me around and lectured me and we watched a movie and oh, guess what? Your big sister showed me her rack."

Sarah leaned forward and planted her chin on her little fist. "Oh really? Her Highness finally flashed you some boob, huh? And this incredible vision made you squirt allllll overrrrr?"

I loved it and hated it when my Sarah teased me about masturbating. She had been such a trouper when she pretended to 'make' me expose myself and beat off in front her mother. I was never sure when she was acting, playing the indignant wife of a pathetic jerkboy. Or when she was being a happy hotwife preparing to meet her side dick and humiliating me.

"Are you OK with - what's been happening?" I asked her.

Sarah sat back and looked down at her breasts. "I'm learning some things..." she began and then shot me a sly look. "Not like that! I mean, it's a crazy sex life we have. That has to be good, right? I just..."

"What."

"Honey, at first it was all an incredible turn-on because - because everything was so wrong and naughty. Me having sex with a man who wasn't my husband felt really, um, slutty."

"In a good way or a bad way?"

"Um, it felt good, to be bad. The sex was just sex, you know? But it was hot because it was, you know, bad-girl sex."

My cock surged as I listened to her. It was always a struggle when she talked to me while she was spreading. I wanted to look at her pretty, animated face and stare at her gorgeous vulva at the same time.

"But that changed," she went on, still examining her boobs, hefting them and checking how firm they were. "When Carl was doing me - sorry - I imagined that you were, like, making me have sex with him. Like I had to, because you wanted that."

Uh oh. I had a shoebox full of pictures of Sarah's mother doing things because her husband wanted that. Sarah's sister had pulled up her pajama top and bared her chest while she imagined that I wanted her to do that. I hoped it was for me, anyway.

"So I'm learning about myself. Like this. What we're doing. At first it was super naughty, you know, just baring the ol' beav and seeing you masturbate. I can't believe I'm even talking about this. I didn't understand the feelings I had. Now I do. I like being like this for you."

Sarah let go of her breasts and used both hands to pull her labia wide open. It was just plainly lewd. Her once-pretty pink funhole had become a torn and gaping cunt. I had to let go of my dick or it was going to spurt.

"See? Get a good look. This is so slutty. And it works great for me if I'm a slut. For you."

"I love you, sweetheart."

"I know. Are you done? You can stick it in for a few minutes before I have to get ready for work."

Pulling her by the legs toward me on the bed, I positioned her and plowed into her looseness. Another, much-bigger cock had changed my wife's vagina into something my penis no longer recognized. It was just another whorish meat wallet now. She smiled at me comfortably as I did my pumping and in short order heaved her chest, closed her eyes and blew out of her mouth.

My sweet Sarah faked her first orgasm with me.

Remembering I wasn't allowed to come, I rolled off of her and buried my face in a pillow so she couldn't tell that I knew. A little hand slapped me on the butt as she hopped up from the bed. "Thanks, I needed that!" she told me on her way to the bathroom for her shower before work. Regret and destitution clamped right down on my balls as I got myself dressed and prepped something for us to toss down before we were late.

"There's something I want you to do for me," Sarah said while she did her makeup in the dresser mirror. I walked over and set down the cup of french-pressed coffee I had brewed for her. "Your task is to show your panties to a man, and send me a picture to prove it. You figure out how."

This came out of nowhere. I stood next to her, transfixed, mind and heart racing.

"Come on, babe. We both know how *you* want to be a slut for me."

Talk about pushing boundaries. "Today?" I managed to croak.

"If possible. Every day you wait will be a week without any sex. No Mom. No Suzy. No jerky-jerk." I cringed a little when she made that dreadful hand gesture, pretending to jack off. That always disturbed me when a woman did it.

I tried to control my breathing while I silently prepared to leave. One day to get this done? On a work day? Sarah came to me and tipped her mouth up for a kiss. "Whatever happens is okay," she whispered. "Understand?"

"I have no idea what you're talking about."

"Right, Mr. Panty Man. See you, and I do mean *see* you, later!"

Driving to work, I could barely conjure scenarios where some guy looked at the ridiculously small pair of women's bikini briefs I was wearing. Sarah of course had selected some girlish white ones with little daisies on them. I heard her sister Suzette in my head lecturing me about exposing myself, and then I remembered a similar lecture from Barbara, the lawyer whom I had clerked for. The woman who had turned me into a jerkboy.

I was Barbara's Boy Friday at her law firm. I worked at a firm now, like her. And I had a Boy Friday! A red-headed gay kid who ran copies and answered phones. Randy. Sure, he was only 22 or so, but he must be hip to guys experimenting or dressing like women or whatever gay people do.

"Close the door," I told Randy after I had called him to my office. "Sit down for minute."

"Is everything okay?" The kid looked at me curiously. I wasn't exactly his boss as he was part of the secretarial pool.

"Everything's great. Look, what I'm about to talk about is close to straight-up sexual harassment."

"I don't understand. I haven't sexually harassed anyone . . ."

"No. Jeez, Randy. I'm just going to tell you, okay? My wife is playing a game with me, kind of like Scavenger Hunt. I have a task to perform." When I let the word "perform" slip out I felt my dickhead throb.

"What's your task?"

"Don't laugh, okay? I'm, uh, wearing women's panties right now."

Randy's eyebrows shot straight up and a look of flirtatious adventure lit up his face. I wanted to crawl under my desk. He probably spotted the flush in my cheeks, because he instantly shifted gears from Boy Friday to mischievous gay guy tormenting a straight guy. We had played this game a little around the office. It amused some of the women.

"So what task are you supposed to 'perform' - in your panties?" Randy was clearly enjoying the situation.

"Oh, man. Just twist the knife. I have to show them to a guy and send her a pic somehow proving I did it."

"Boo! That's it? Don't I get to show you my underwear? Oh, I forgot. I'm not wearing any . . ."

"No! I mean - look. Will you help a brother out?" I was getting exasperated. My dick kept telling me it wanted to get exhilarated.

"I don't know. Will you - help a brother out?" Randy could barely suppress his glee.

Then I just spewed words. I don't know why. I guess I had been playing scenes in my head where I lowered my pants and then things started spinning out of control and then I would stop the fantasy. And then I would start over again. I submissively told Randy, "I'll do whatever you want."

That stopped the repartee. There was a pause and a scary silence. I said, quietly, "Please. Help me take some pictures for my wife."

Randy stood up. He turned away from me and I watched him lock my office door. "Sarah, right?" he said. "That's your wife? I remember her from the Christmas party. She's really nice." He was walking toward me, around my desk, while he talked. "You know what she really wants to see, right? Undo your pants."

I listened and looked at him and saw the erection in his tightly tailored slacks when I was feeling for my belt buckle. Randy kept talking to me, rhythmically, saying, "Have you ever looked at girl-on-girl porn? Did it turn you on? Pull them all the way down."

When I lifted my butt off my chair to get my trousers off it caused my hard penis to pop out of the top of the tiny white panties. I felt it happen and instinctively, after hours of doing it for Suzette and Sarah's mom, spread my knees as wide as I could.

"That's hot. Women get the same kick out of the same kind of porn," Randy was saying as his eyes feasted on my pantied penis. "Only the opposite type."

I knew what he meant. Suzette had forced me to confess the various kinds of porn I looked at, ruefully spilling it all out in front of Sarah's mom. I'll never forget her incredulous look when I said the words, "Husbands sucking cock." My eyes didn't leave Randy's groin. I just reverted to my training and opened my mouth, let my tongue hang like a doggie and panted. Deep breathing helped me to avoid blacking out.

"Wow. We really don't have much time. They're going to notice I'm missing soon. Do you want to see mine?"

I felt my head nodding. Asking for gay cock. If Sarah could only see me now. Randy's hands moved in front of my vision and expertly pulled his thickness and tight ginger balls through the fly of his pants. He really wasn't wearing underwear. His fat glans looked like a ripe little apple. My eyes wanted to avert, and I didn't want to turn away for fear of offending him. So I looked up, and into the lens of the smartphone.

A flash blinded and captured me, slack jawed and spread open in my leather office chair with an erection poking out of my little girl panties.

"You have to prove you're with a man," Randy said. I blinked, not comprehending. "Just put it in your mouth, just for a second, while I get a picture for your wife." The insane fantasy I had been running and stopping all day was actually happening. And Sarah was going to see it. I ordered myself to suck it. For her enjoyment.

Randy's young cock felt incredibly warm and smooth on my tongue. Sure, I had spent time mouthing a cock-shaped dildo for entertainment purposes and yeah, pretending it was a real one made it easier to overcome the shame. This was craziness, swirling my tongue around my Boy Friday's knob, in my own office. He was going to remember this, too. Would he tell someone? Fuck. Of course he would. I recalled the awful pic Suzette had of me gagging on that pink dildo, and my head started to bob. Just a little. The vision released a flood of fantasies of me blowing Randy in front of women in the office. Of course he could make me, now.

"Um, this sure doesn't feel like your first time," said the copy boy, snapping me back to semi-reality. He palmed my chin so my mouth stayed on his cock and pulled me toward him as he stepped away slowly. It caused me to lean forward in the chair, almost to the point of falling.

"Perfect. Look up at me with your eyes." The flash blinded me again. "Got it," Randy said as he peered at the smartphone. He turned the device around. I didn't let that warm dick out of my mouth while looked at myself sucking it and my pantied backside on the screen, perched on the edge of the chair.

"I'm loving this, you know, but I really have to get back." Randy's hands took the cock away and put it back in his auburn houndstooth trousers. I watched it disappear. "Now, now. You can have it another time, if you want," he was saying as he pressed things on the phone's screen. "There! Two pics of proof for Sarah. We did it! Gotta go now."

With that Randy slipped out my office door, only opening it enough to get out and not show anyone that I was still sitting there, mouth wet from gay cock and a screaming erection poking at my belly. Pulling up at my pants on the way, I rushed to lock the door before someone caught me. As much as I was dying to rub one out, the need to get back into my clothes and back to feeling normal was greater. None of the bizarre degradations I had performed for women in my strange Jerkboy career had shaken me like what had just happened.

Zipped up, belted and suited behind my desk, I looked at emails but all I saw was that hi-resolution photo of Randy's fat knob in my mouth and the look of sissy subjugation in my eyes. A hollowing emptiness struck me when I admitted to myself that I would be performing fellatio for real next time. To completion. And there *would* be a next time. I owed Randy for helping me out, I explained to the part of me that was screaming I wasn't gay.

Desperately I snatched my smartphone to look at the nude pics it held of Mrs. Landtree. It soon tooted the ludicrous royal ringtone that Sarah had installed to announce her texts. With dread my eyes rested upon her pulsing hearts and ecstatic smiley emojis with the words:

GoddessSarah: AMAZING!! I'm so proud of my brave cock smoker!!

What do you text back to something like that? From your wife? The stupid royal announcement sounded again:

GoddessSarah: Was it hard? I'm mean doing it bwaahahaaa!!

Me: well it was different. have to get to work talk tonite

GodessSarah: Loooove You!!

Staring at the smartphone, I scrolled back to see if Randy had said anything in his message with the dirty pics. There was nothing. I checked my email sent box, already getting angry. I was on the company's email server and he knew it, because he had set it up for me. Nothing there, thank god. What the fuck? Then I realized Randy must have used his own phone. He did! I never saw him pick up or set down my phone on the desk!

How the hell did he have Sarah's digits? A smile cracked all over my face. That vixen! She had to have set up the whole medieval passion play with Randy. Had to! I dialed his extension.

"This is Randy."

"Oh, bullshit. You can see it's me by the number on the board."

"Did you need me?"

"I figured it out. You and Sarah set me up." I wasn't angry any more. I was relieved.

"Mmmmaybe. Are you okay?"

"Fuck, man."

"Hmmm. Is that a Freudian Slip?"

I busted out laughing. We were back to stupid gay jokes and I felt like my feet were back on the ground.

"I gotta go," Randy said and went back to his usual runaround job. I grabbed my smartphone.

Me: You sneaky little shit.

GoddessSarah: Wha?

Me: You set me up with Randy

GoddessSarah: SUCKER!! and I do mean that literally

GoddessSarah: here's your reward hope it still makes you hard lolzzzz

My wife had attached a selfie of her hand pulling her panties aside to show me a closeup of her fantastic pink vulva. I sighed and thought about how much I loved her.

GoddessSarah: Guess what's for dinner, chump

Me: love you so much

GoddessSara: cya tonite

My paralegal buzzed to remind me that I had a several important calls to return. "Thanks, Carly," I said, adding, "Would you come here for a minute?"

"Whitworth is blowing up," my right-hand blonde told me as she strode in and closed the door. She had been my work wife almost as long as I had been married to Sarah. We knew each other from way back to my law internship with Barbara Wilson, the woman who guided me into the jerkboy life. One look at my face and Carly could tell something was up. She had seen all my faces, many times.

"Good lord, you look like the first day I saw you in Barbara's office." Carly spun right back to the door and locked it. Into her 30's now, my best woman friend was holding her own against the secretarial spread and had recently changed her hair to the utilitarian bob a single soccer mom.

The belt of my trousers was already loosed by the time Carly had released two buttons on her blouse. It was a familiar, wordless ritual for us. I had a hand on my surging dick when she fished one breast out of her white brassiere. My eyes latched on to a strawberry nipple and I beat my meat.

I never got over masturbating in front of Carly. One Tit Out was her non-verbal signal that I should do it. I stopped asking her when I married Sarah and Carly made it clear that she wasn't going to tolerate sexual activity with a married man. We had a long, hot history though and One Tit Out, totally at her discretion, had managed to leak back into our friendship over the years. I adored her for knowing when I needed it, and making me do it when she needed it.

"C'mon, stroke it fast for me," Carly said passively as she checked her smartphone.

"I'm, ah, not allowed to come."

"We don't have time for begging. You've got calls. Stand up and pound it hard."

On my feet, never taking my gaze from Carly's delicious, hardening nipple, I told her, "Sarah is supervising me now." It felt oddly embarrassing to tell Carly I had revealed my shameful tendencies to my wife.

"Well, hallelujah! I'm bringing my new boyfriend along, slowly. I'm so used to you I forget sometimes how normal guys freak out. You should have seen his face the first time."

My hands slammed onto the desktop and I struggled not to squirt from the sound of her voice and my imagination showing me a nude Carly with a masturbating man.

"Something has you ready shoot, and you've seen this old boob a hundred times. What's happened?"

The only thing that saved me from shame-coming was the fear of what I was about to tell her. I took several deep breaths to try to calm myself before I said the words: "I sucked Randy's cock."

"Shit! Really? What the hell are you doing? You're married!"

I carefully and lightly worked my straining penis, at eye level to Carly in the chair across from my desk, breathlessly explaining that Sarah had set it up and wanted a picture. And then the image of Randy's wet cock knob when it came out of my mouth took the place of Carly's womanly nipple.

"There's an effing picture?" Carly reached toward the desk for my smartphone.

"It's, ah, on Randy's phone." The words made my testicles generate an extra ounce of semen. The pressure and the guilt spread into my abdomen.

"Oh my god, you lunatic," Carly snapped. Hearing her scold me froze my diaphragm. I couldn't breathe and I was overheating in my clothes. "Barbara told me she always wanted to make you suck one, but she never found a way. Hey, speaking of that. Guess who is the arbitrator on Harrington? I'm sure she'll be glad to see you again."

With a mention of Barbara, beautiful black Barbara, with her contralto voice and incredibly soft, full lips that she let me kiss sometimes as I ejaculated for her - it was too much. I melted down and cried as I orgasmed all over the office desktop, making sure Carly could look at the desolation and stupefaction in my face. We knew that was the best part for her.

The boob was back in her blouse before was I finished. "You're in trouble, and not just for making a mess without your wife's permission. I'm going to go talk to Randy," Carly said as she buttoned up and stood. While she checked her blouse and skirt for cum stains she muttered, "Time to save your ass again." I fell back into my chair with my pants around my ankles.

"Call Whitworth when you get yourself together," she told me firmly as she left my office.