Not a Man Ch. 02

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Tess finds out about Jay's plan.
9.8k words
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Part 2 of the 4 part series

Updated 06/08/2023
Created 05/28/2016
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rarmons
rarmons
2,430 Followers

Hello readers, hope you'll enjoy the second installment as much as I'm having fun writing it! I hope the pacing isn't too slow. Don't worry, things are going to heat up soon. If you have ideas what new name Henry should pick for himself, feel free to leave suggestions in the comments.

*********

I woke up the next morning, feeling like someone took a sledgehammer to my head. For just a few, glorious moments, I had no idea why I got so drunk the night before, or why I was lying on the couch instead of my own bed. Then the memories came rushing back, and I wondered briefly if I was still asleep, having a nightmare. Tess, oh beautiful Tess, defiled by that monster in ways I never even thought possible. Jay, the monster in question, who seemed to have me in his grasp.

A pretty, blonde anchorwoman on the TV screen droned on about a stabbing downtown last night, but I didn't care, unless by some miracle it turned out to be Jay. The clock on the bluray player read 8:09 am. That woke me up all the way. I only had about twenty minutes to get ready, and too much to do.

With a sigh, I got up, and turned off the TV. I gathered the empty cans of beer off the table, and threw them in the trash. Despite the fact that I showered the previous night, I still felt unclean. It would seriously cut into my prep time, but I needed to have another one. I didn't have time for a real breakfast AND a shower, but at the very least, I started the coffee maker. At least I didn't have to shave on top of it. I had shaved on Tuesday, and there still wasn't enough to even call it stubble.

In the bathroom, I stripped off my pyjamas, and was about to throw them into the laundry hamper, when I hesitated. Sitting at the top of the pile was the t-shirt I had worn on the drive home. The one that was still coated in Jay's cum. I reached in, and picked it up. The large, dark stain was unmistakable. It hadn't even fully dried, yet.

Disgusted, I threw it back in, and headed to the shower cabin. After three steps, I halted, and returned to the hamper. I reached in a second time, and pulled out the sullied garment. Why did it fascinate me so much? It was just a t-shirt with cum on it. No, it was more than that. It was a sign of masculinity. A representation of the virility of Jay's manhood. A reminder of the way Jay had so utterly dominated me.

My little cock twitched, and to my surprise, became erect. What the hell was wrong with me? Jay had blackmailed me, humiliated me, defiled me. It wasn't supposed to make me feel that way. But then again, Jay wasn't there. What I did in the comfort of my own house was nobody's business but my own, and it's not like Jay was there to see it. I was just tending to my body's natural reaction. It was completely fine as long as nobody found out about it, and I certainly wasn't going to tell anyone.

I put my hand inside the shirt, and the dark spot felt cold and damp against my skin. The moment it touched my throbbing dick, my skin tingled with anticipation. I began pumping away, every motion infused by the power of real masculinity. I imagined myself with Jay's massive cock. Tess was in front of me, on all fours, presenting me her pussy.

Tess would moan something along the lines of, "Oh, take me, Henry. I love your big cock, Henry. I've always loved you, and only you!"

With a shudder, I came, and my warm cum mingled with the remains of Jay's. After the burst of energy, reality set in again. There wasn't a huge, veiny, pulsating beast of a cock in my hands. There was only the usual small, pathetic little worm. Disgusted, I threw the shirt back in the hamper.

How many precious minutes did I waste? Stupid Henry, I chided myself. It was a stupid fantasy. The chance that my cock would suddenly grow was next to nil. No, I had to correct myself, it was exactly zero. Jay was right. I was pathetic. A failure of a man. No, what had Jay said? Not a man at all.

The cold water hit me in full force, but I didn't care. At least it covered up the steady stream of tears. The only thing that could have made me feel worse, would be Jay there to see my utter humiliation. Or Tess.

I cleaned myself mechanically, and the water eventually warmed up. Five minutes later, I stepped out of the cabin, and towelled myself off. I walked to my bedroom, refusing to so much as look at the hamper.

I was definitely not going to let that happen a second time. In fact, I was not going to let Jay keep blackmailing me, either. It was bad enough what he did to me already, but that was it. No more. It didn't matter which words came out of his stupid mouth, but I was a man. I had a cock, and I had two balls. Nobody could take that away from me. I promised to myself that I wouldn't let Jay control my life.

My phone displayed 8:25am. I dressed hurriedly in my usual work outfit, sipped half of the scalding hot coffee, burning my tongue in the process, and was almost out the door, when I spotted the underwear lying on the living room floor. Tess' black bra, and panties, given to me by Jay, with the explicit instructions to wear them, and the promise that he would check up. God damn that man.

It had only taken about three minutes for me to break the promise to myself. I hurriedly undressed again, and stripped off my briefs. Out of curiosity, I held up Tess' panties to my nose, and took a whiff. They hadn't been washed, and I smelled a trace of her aroma. It was wonderful, and if I hadn't been pressed for time, I might have buried my face in it, and jerked off again.

Instead, I sighed, and stepped into the holes. The fabric slid up my legs, and raised goosebumps on my thighs. They were much smoother than my own briefs, but they turned out to fit almost perfectly, owing to the fact that Tess and I were basically the same size. I took a few steps, and the smooth silk felt unfamiliar against my balls, but not in a bad way.

I suddenly remembered that they were used. The same fabric that was now touching my dick had once been in direct contact with Tess' pussy. Was that as close as I'd ever get to her? I got an erection again, and I almost couldn't help myself. The front of the panties stretched tight against my hard member, and I would have loved to jerk off for the second time that morning, if the clock hadn't been ticking.

I picked up the bra, and hesitated. Panties were one thing, but a bra? Fuck it, I was late for work, and in too deep already. I didn't have the luxury of time to debate whether or not to do it. I pulled the unfamiliar lingerie up my arms, and tried, but failed, to close the clasp in the back.

Cursing, I pulled it off again, and studied the little plastic hook. It had been years since the last time I actually had the opportunity to undo one of those, and I struggled to recall the memory. It was easy enough, and I managed to do it twice, before pulling the bra back on. Once I had to do it behind my back, though, I failed. It didn't help that my fingers trembled with suppressed anger.

Finally, I just gave up, closed the clasp while holding it, then pulled the bra on like a t-shirt. It was tight around the bottom, but the cups just flopped around loosely. Tess and I weren't that similar, after all. I wondered what I'd look like if I had tits like hers, but only for a second, before cursing myself for even thinking it. That wasn't helping my current predicament at all.

After pulling on my jeans and t-shirt, I checked the mirror in the bathroom, and to my dismay discovered that through my white top, the dark outline of the bra was very definitely visible. I sprinted back to my bedroom, got a black t-shirt out of the closet, and a sweatshirt on top of it, just to be sure.

The phone read 8:38am, and by the time I raced down the stairs to the ground floor, I had almost forgotten I was wearing Tess' panties. They felt as natural as my own underwear. I did feel the bra, though, sliding around due to my lack of natural support, and chafing my nipples with every step.

The engine of the Toyota roared to life, and I pulled out of the driveway fast enough to make any Formula 1 driver pale. The commute to Lifelast was about fifteen minutes, pending traffic, but if I hurried, I could make it just in time. I stepped on the gas pedal, and raced along 5th, and Main.

On Washington Ave., I blazed through an intersection where the signal just turned red, and I prayed nobody saw it. My prayers were, of course, not answered, and moments later I heard the blaring of a police siren. God fucking damn it. I wanted to cry.

I pulled into a Starbucks parking lot, and watched the cop car pull in behind me, and slowly come to a halt. The officer took his sweet time, before he got out of the car, and approached the driver's side of the vehicle. My fingers tapped nervously on the steering wheel, as the seconds on the clock ticked by. It was 8:56 am, and I would definitely be late. I tried to calm myself, and lowered the window when the officer tapped on it.

"Good morning, Officer," I greeted him, trying to put on a smile.

The man just harrumphed, and I sighed again. A pissed off cop was the last thing I needed, but at least I was white. Officer Hill, according to his nametag, appeared to be more than slightly overweight, and in his early forties, although the sour expression on his face easily made him look older.

"License and registration, please."

I leaned over, and dug the registration, and insurance info out of my glovebox, and then pulled my license out of my wallet. "Here you go, Officer," I stated politely, and handed him the papers.

"I'll be right back," he announced, and walked back to his car.

A minute passed, and Officer Hill made no indication he'd return soon. Another minute passed, and the clock read 9:00am. I caught myself tapping my foot nervously, and forced myself to relax. After taking a deep breath, I leaned back in my seat, and closed my eyes. When it rains it pours, and I forgot to bring an umbrella.

The sound of heavy boots on the pavement heralded his return, and I opened my eyes again. Five past nine.

"Do you know how fast you were going, back there, Mr. Newman?" he inquired, handing me back my documents.

"I'm really sorry, Officer. I'm really late for work, and I guess I didn't really pay attention," I apologized.

"That so, huh?"

"Yes, sir." I don't know why, but at that moment it hit me just how absurd the whole scene was. I was sitting there in women's underwear, and he had no idea. I wanted to laugh.

"Guess you didn't see the red light, then, either?"

"No," I lied. Fuck.

"You were going almost seventy in a fifty-five zone," he elaborated.

"I'm sorry, like I said, I'm late for work, and—"

"I understand, Mr. Newman, but you also ran a red light. Can't let you off with a warning."

"Okay," I gulped.

Officer Hill handed me two slips of paper, and I didn't even bother looking at them. I didn't want to look at them.

"You need to be more careful in the future. Lotta accidents happen on this intersection."

"I will, Officer."

"Alright," he concluded, but he sounded like he didn't believe me. "I won't keep you any longer."

"Thank you," I blurted out.

Officer Hill tapped on the roof of my car, and then retreated to his. Moments later, he was gone. I was left with two tickets, and increasingly frayed nerves. I took a glance at the tickets, and got a sinking feeling in my stomach. A hundred bucks for running a red light, and hundred-fifty for going fifteen miles over the speed limit.

What's done, is done, I told myself, and held back the tears. Instead, I turned the key in the ignition, and drove the last mile to Lifelast on autopilot. On the upside, if I got fired from Lifelast, I'd be rid of Jay. Hell, that might almost be worth it.

I pulled into the parking lot fifteen minutes late, but I was beyond caring. Or, at least, I thought I was.

"Late again, Henry?" came Darla's shrill cry the second I opened the door to the IT department, and I flinched.

"Yes, Darla," I replied lamely, and sat down at my desk. It wasn't even nine thirty, but I already wanted the day to be over. Fortunately, the weekend was just around the corner. I really needed it.

Darla McIntyre, my direct superior, shambled over to my cubicle, and leaned against the divider. The overpowering stench of ashes and nicotine filled the small space, and I almost gagged. She was a perfectly ordinary fifty year old woman, except for her leathery smoker face, and an attitude harsher than the tar in her lungs.

"That's the third time this month," she reminded me.

"I know."

"I'm gonna have to write you up this time," she threatened.

"Whatever makes you happy, Darla."

"Do you think this is some kind of joke, Mr. Newman?" she barked. Darla always went back to calling me Mr. Newman when something offended her, which happened all too frequently.

"No, of course not," I protested. "Sorry, I just got a lot on my mind. I got pulled over on my way to work, that's why I'm late."

"I don't see how that is Lifelast's fault—"

"I never said it was," I tried interrupting, but she just kept lecturing.

"—and we certainly won't make excuses for criminal behavior." Criminal? "Don't think you can weasel your way out of the rules."

"I'm not trying to."

"Good. I'll be watching you, Mr. Newman."

Darla turned on her heel, and departed in a puff of foul odor. She had been the result of Lifelast's minority outreach program, which encompassed the goal to increase the ratio of female to male employees in IT. Unfortunately, they overlooked the qualifications for the job, and hired her. What she lacked in technical knowhow, she made up in smoke breaks, and tattling on her coworkers. It didn't take long for her to get promoted, just so she would cause less damage trying to do the job.

At that moment, I would rather have spent another evening with Jay, than another five minutes with her.

I sighed for the umpteenth time that day, and started working. There were plenty of tickets, and I spent the morning crawling under desks, plugging in cables, and installing software. Every time I stretched, or bent, I was reminded of the fact I wore a poorly fitting bra. Fortunately, nobody else seemed to notice, although a few people did ask me if I'm not too hot, wearing a sweatshirt on such a warm day.

By the time lunch rolled around, I actually ran out tickets, and, for just a brief moment, felt good about myself again. I took pride in my job. It was the one thing I was good at.

My solitude was interrupted by the person I least expected to show up: Tess. She knocked on my cubicle wall, and I turned to look at her in her full glory. Fuck, everything about her was perfect, from her cute sandals, over her tits, and up to her immaculate face.

"I—oh, hey, uh, Tess," I stammered, all too aware at that moment of the fact I wore her used underwear.

"Hey, Henry," she greeted me warmly, and I pretended I hadn't seen her beg Jay to fuck her cunt less than half a day earlier. Or her ass. Jay really had ruined everything.

"What's up? You wanna go to lunch together?" I proposed.

"Uh, um, not exactly," she began. What in the world did she have to be squeamish about?

"What, then?"

"Sorry, this is kind of embarrassing," she admitted, and actually blushed, "but, uh, Jay said that—well, he said he gave you my underwear?" She blurted out the last bit, and my heart sank down into my stomach.

"Uhhhhhh... he did?" I inquired, trying to buy time.

"Yeah. I kinda left them over at—no, it's personal, and... well, do you have them?"

"Yeah," I admitted, not knowing what else to say.

The silence that followed was palpable, and lasted half an eternity.

"So... can I have them?" she broke the silence, looking as mortified as I felt.

"No," I blurted out without thinking.

"You have them at home?" she continued, her awkwardness changing into confusion.

"Not exactly."

"In your car?"

"No."

"So what's the problem, then?"

I tried to think of something, anything, I could say that wouldn't reveal I actually wore them at that moment. "I, uh, can give them to you, but, uh, I need to use the bathroom first."

"Why do you need to... oh god..." Her eyes went wide, just as my heart stopped beating. "You're not... wearing them, are you?" she pleaded.

My silence was enough of a confirmation for her. She squeezed her eyes shut, and raised her hands in utter disgust, as if she was trying to ward off evil.

"Oh god, ew, ew, ew!"

"Tess, wait!" I called after her, but she was already out of the door, and around the corner.

I didn't have the energy to go after her, and explain myself. What was the point? My life was basically over at that point, anyway. There was nothing I could say to her that wouldn't make me look like the freak I knew I was.

Tess, the one good thing in my life, the one person I wanted the most, the one person I loved, now thought I was a pervert. It felt like my last hold on life slipped away, and it was all because of Jay. I felt incredibly sick, and knew I had to get the hell out of there.

"Leaving early, Mr. Newman?" remarked Darla acidly, but I ignored her.

I made it as far as the bottom of the stairs, before I had to dash off into the bathroom. I raced to the first empty stall, dropped to my knees, and puked. The bitter acid tasted foul in my mouth, as I puked out the coffee I drank that morning. The cold tiles pressed hard against my knees, and the foul odor of the bathroom made me heave a second time.

I definitely felt better afterwards, though. After splashing a bit of water on my face, and rinsing out my mouth, I continued to the parking lot, savoring the fresh air. Once my stomach settled enough, I got in the car, and started driving.

For half an hour, I drove around aimlessly, not really caring where I'd end up. Eventually, my stomach rumbled loud enough that I couldn't ignore it any longer, and I pulled in at a fast food joint. A cheeseburger, fries, and a coke later, and I felt almost like a human being again.

Definitely not like a man, though.

I arrived back in the office to silence, despite being gone for over an hour. Darla, as much as she loved deriding others for every single mistake, never really cared too much about her own work ethic, and always stayed out for at least ninety minutes. None of us cared too much, because she actually did us all a favor by being gone.

Apart from a handful of new tickets, I was greeted by an unread email from Jay, titled "LOL." I thought about just deleting it without reading it, but then double clicked on it.

"Oh my god Henry you won't believe who was just here! Tess came crying to me, telling me all sorts of really interesting things about how her friend Henry told her he was wearing her underwear. She was so upset, the only thing that calmed her down was me pumping her cunt full of my cum. She's so glad that her boyfriend is a real man, and not a freak like that Henry guy.

"Anyway, that's enough proof for me that you went along with it. Come to my apartment again, 6 o'clock this time. Don't be late. -Jay"

I had been expecting it, or at least something like it, so I wasn't too surprised. That didn't make me feel any better, though. At least I wouldn't have to look at him... not until six, anyway. For the rest of the day, I kept wondering what Jay had in store for me this time, and whether or not I'd ever speak another word with Tess again. Darla came back from her extended lunch eventually, shot me a nasty glare, and then disappeared in her office, leaving behind the smell of cigarettes.

It had only been roughly forty-eight hours, but it felt like a lifetime since I had spotted the Jay and Tess in the copy room. My entire world had been turned upside down in a surprisingly short amount of time, and there wasn't an end in sight.

rarmons
rarmons
2,430 Followers