Not a Man Ch. 02

If I wanted to get to Jay's on time, I'd have to leave Lifelast at five. That wouldn't make Darla any happier, but to be honest, I had more important things on my mind. The happiness of Darla was very much at the bottom of my list of priorities.

At precisely five, I checked my e-mail one last time, to make sure I hadn't missed anything from Jay, logged out of the system, grabbed my things, and headed down the stairs. I didn't bother listening to what Darla yelled after me. It was probably something along the lines of, "Leaving so soon, Mr. Newman?" Fucking bitch.

I already knew where to go this time, but I had to beat rush hour traffic. Ten to six, I pulled into the parking garage at Lakeshire Blvd., not quite ready to face Jay. I wish I had had the time to make a stop at home, although there wasn't really anything I wanted to do there. I just didn't want to go to Jay's.

At five to six, I stepped into the elevator, and pressed the button for the sixth floor. Whatever Jay wanted, I hoped it wouldn't take long. Maybe he was just going to jerk off on my back again, and then I'd be out of there. That wouldn't be so bad. At least I could get out of the underwear. Considering that notion, I realized that I didn't even feel the bra anymore. Funny how it only took me half a day to adjust to wearing it. Except only Jay was the one laughing.

Two minutes to six, I rang the doorbell to apartment 6B. Jay opened the door, and beamed at me.

"Ah, Henry! So glad you could make it," he greeted me warmly, and let me inside.

"I'm here because you ordered me here, nothing more," I retorted. Jay closed the door behind me, and it felt like the door to my cell snapping shut.

"Come on, now. You had at least a little fun last time you were here, I cleaned up the proof of that myself." My eyes darted over the spot on the wall that had been stained with my cum the last time I was there, but couldn't detect a trace of it. "Besides, I never ORDERED you here today, I just asked you nicely, and like a good girl, you came. No pun intended."

"Don't pretend like there's any reason why I'm here, other than the fact that you're blackmailing me."

"Calm down, Henry, it was just a joke. I don't want you as upset as Tess was when she came to me today." Jay broke out in sudden laughter, and clapped me the shoulder. "Oh god, Henry, you should have been there, it was great. Anyway, sit down, I'm just catching up with a game."

I knew better than to argue, and sat down on the couch. The apartment looked exactly like it had the previous day, and I don't know why I expected it to be any different. I kept looking for some sign of Jay's cruel nature, but everything looked clean, and modern. There was no evidence a complete madman lived there.

"You watch football, Henry?" inquired Jay.

"No," I answered honestly.

"Figures," he chuckled. "You want something to drink?"

"Sure, beer's fine," I responded automatically.

"Oh, please, I save the beer for the guys," he laughed, and went off into the kitchen.

The screen was paused on a shot of a football game, although it appeared to be recorded by someone in the bleachers, not a professional game. Jay reappeared with a bottle of beer in one hand, and a glass of wine in the other. He handed me the glass, of course, and then plopped down on the other end of the couch. He resumed the video, and I took a sip of the wine.

I had no idea what was going on in the game, but it seemed like college game. The recording was shaky, and the buzz of the crowd drowned out the noise of the game itself.

"Who's playing?" I asked, after my glass was half empty. And it was definitely half empty, not half full.

"Oh, right. That's my brother's team playing. There," he pointed at the screen, "number fifteen, that's him."

The guy he pointed out was too far from the camera to make out any details, other than he was large, and muscular.

"You have a brother?" I asked, surprised. For some reason, I couldn't imagine that someone as big of a dick as he was could have a family. It seemed too... normal.

"Yeah, just one, but I have two sisters. I'm the oldest. That right there is Dave. You already know one of my sisters, I believe."

"I do?" I asked, confused.

"Olivia, duh."

"Oh, right," I remembered the whole e-mail fiasco. My face flushed with embarrassment, and I emptied my glass of wine, trying to cover.

"And then there's the youngest of the family, Dani. I think she'd really like you."

"Oh? Why's that?" Surely he couldn't mean to actually set me up with her, after what he did to me.

"She's a lesbian. She really likes pussies."

"Ha, ha, ha. Very funny."

"What about you?" Jay asked.

"Me what?"

"Siblings. Got any?"

"Oh. Yeah. Older brother. Clyde."

The two of us never really got along. Clyde seemed to succeed at everything he did, and he had moved out of the house when he hit eighteen. He was married now, and lived somewhere in New York. I only saw him, and his fancy, french wife, on Thanksgiving.

Jay paused the game, took my glass, and without asking me if I wanted a refill, went to the kitchen. He came back, and handed me the full glass.

"By the way, did you happen to bring Tess' underwear? She actually does want it back."

"Yeah," I responded numbly.

"In the car?" he inquired, and I got a strong sense of deja vu from my conversation with Tess.

"No..."

"Oh jesus," he chuckled, "You're still wearing it?"

"Yeah," I admitted meekly.

"Damn, Henry, you're a natural little pussy, aren't you? I expected you to change the moment Tess humiliated you like that. Jesus... the whole day?"

"I didn't really think about it, and I didn't have the time to change before coming here," I explained.

"So, you like wearing a bra and panties?"

"No. I don't know. I don't really feel it anymore."

"Come on, let's see it, then."

His request didn't surprise me at all, but that didn't mean I liked it. "Do I have to?"

"Yes, Henry, you have to. If it makes you feel any better, I'll blackmail you, yadda, yadda, yadda. Now get on with it."

I stood up, and it wasn't as difficult as last time. This time, I was already prepared. I started with my pants, because it seemed less embarrassing to be seen in panties, than in a bra. Jay, the supreme asshole, whistled when the black silk came into view.

"Damn, Henry, that looks so smooth. How the hell do you manage to fit a dick in there?" he mocked.

"Fuck you, Jay."

"In your dreams."

I dropped the pants to the ground, and kicked them away. Next, I took off the sweatshirt, revealing the white t-shirt. Jay didn't tell me to stop, so I took that off as well. As soon as he saw the black straps of the bra, he started laughing.

"Oh jesus fucking christ, Henry, you look ridiculous."

"You told me to wear this," I defended myself. The cool air of the apartment slid across my naked skin, and raised goosebumps all over my body.

"I know, but still...," he wiped a tear from his eye. "We're gonna have to get you your own little bra, I think. One that fits."

"So can I take it off now?" I pleaded.

"No... no, I think I like you this way. Come on, let's keep watching the game."

I resumed my seat on the couch, finding it fortunately still warm. The air was a little bit too chilly to be comfortable, so I emptied half of the glass of wine, hoping it would help warm me up. It warmed up my insides, but the goosebumps on my arms and legs remained.

On the screen, the game kept going, and Jay cheered every time his brother's team got the ball. He booed when they lost possession, and cursed at the ref. None of the people I knew were that much into sports, but Jay seemed to be so into the game he didn't even seem to be aware that I was still there.

Fifteen minutes later, and the glass was empty again, but the chill air seemed even colder.

"Can I put my clothes back on?" I asked him.

"Why?" he asked, absentmindedly.

"I don't know if you've noticed, but it's really cold in here. I'm freezing."

"Come on, you don't need clothes for that."

With one smooth motion, he grabbed my shoulder, and slid me towards him across the couch. The leather sliding across my skin was even colder than my warmed seat, but it only took a second until I sat shoulder to shoulder with Jay, whose body radiated warmth.

His arm pulled me even closer, and I found myself nestled against his strong chest, with his arm wrapped around me like a lover. I shivered, and not just from the cold. I had expected many things, most of them involving his cock, but I hadn't expected that kind of... tenderness.

Mostly just to warm up, I didn't object. I couldn't believe just how warm he was, but then again, he was still wearing his clothes. He smelled of body spray, beer, and something I didn't recognize. Definitely not bad, though. Not that it made a difference, of course. I just wanted to be warm again, not smell him.

"You comfortable?" he asked.

"Yeah," I admitted, and leaned back, relaxing a little.

I've hugged guys, before, of course. Even had my arm around them, in a bar, singing merrily after getting hammered. Yet I knew this wasn't the same. Jay didn't put his arm around me like I was a guy. No, he drew me in, and held me like a girl. I wanted to do something, but it actually kind of felt good.

I've had dreams that were almost exactly the same. Well, the difference was that in my dreams, I was the one holding Tess, not Jay holding me.

"You want more wine?" Jay asked, while the team stood in a huddle.

"Sure," I answered. The alcohol, while it didn't exactly help, definitely didn't hurt.

Jay got up, and disappeared into the kitchen. As soon as he was gone, the cold seeped in again, and I realized that I actually wanted him to hurry back. As much as I hated his guts, he was warm, and I was cold.

Finally, he returned with another beer, and another full glass. More importantly though, with a warm body. He sat down next to me, put his arm around me, and I let out a small sigh.

"This is nice, isn't it?" commented Jay, who must have heard it.

"I suppose," I grudgingly admitted. "But so is a blanket. Or my clothes."

With a score of 49-17 for Jay's brother's team, even I could tell the game was close to being over. Jay started paying less attention to the game, and more to me. It started with just a light brush of his hands across my hip, and I thought he was just repositioning his arm, but it didn't stop there. He seemed to be caressing my skin.

"He's really good, you know?" he commented.

"Who?" I asked, distracted by his hand.

"My brother. Dave. We think they're scouting him for the NFL." Jay seemed really excited by that.

His hand slid across my stomach, and I held my breath. My heart beat faster, and I tensed up. The fingers trailed across my belly button, and slowly moved upwards. Any thought about the game was driven out of my mind. Suddenly, I realized that for all the warmth it provided, his body might as well be a trap.

His fingers slipped underneath the band of the bra, and made contact with my nipple. Jay's eyes were still focused on the screen, as if he wasn't even aware of what he was doing. I was very much aware of the fact that another man was carefully, slowly caressing my nipple. Not even my girlfriends had played with them. Hell, not even I had ever really played with them.

Jay pinched it between his finger, and then traced the hard buds with the tip of his finger. It was weird, and it was erotic, and I realized I hadn't taken a breath in a long time. I forced myself to breathe, and as I did, Jay switched to the other nipple.

It had happened so quickly, I had no idea what to even think about it. The game officially ended, finally, and Jay removed his hand.

"Looks like someone decided to join the party," commented Jay.

I followed his gaze downwards, to the little dent between my legs. It wasn't much, but it was noticeable. In all the confusion, I hadn't even realized I got an erection.

Jay turned off the TV, and focused all of his attention on me. Suddenly, I wished the game were still going.

"You could be such a pretty girl, you know that?" Jay mused, but I had no idea how to even respond to that. "If you grow your hair out, I don't think anybody would even question you're a woman."

"I'm a man," I protested, finally finding the courage to speak.

Jay let out a bark of laughter. "Henry, Henry, Henry... you're as much of a man as this table here. Oh, wait, let me take that back. The table is actually quite big, and hard. This table is more of a man than you are."

"But—" I tried standing up, but Jay continued to firmly hold me.

"No arguments, we both know it's true. I think from now on you should call this table Mr. Table. Now, I want you tell Mr. Table that he's a better man than you."

"Are you insane?"

"No, you're the insane one for thinking you're a guy. Come on, it'll be fun."

"Whatever. If this gets me out of here quicker... Mr. Table, you're a better man than me. Happy?" It was humiliating, no matter how nonchalantly I tried to act. Worse than that, he was right. I was never, ever going to have a cock that women would call big.

"Good enough, for now. Now, let's start on the next lesson."

Jay unzipped his pants with his other hand, and fished out his flaccid cock. My breath caught in the back of my throat. Even limp, his prick was far bigger than my erection. I'd be happy if mine was just half as big as his.

As hard as I tried, I couldn't take my eyes off of it. I slowly reached out, and prodded it with my index finger. It was soft, and warm, both of which I should have expected, except in my entire life, I had never even considered what it would be like to touch another man's penis.

Jay stayed silent, and just watched me. I had no idea what he expected me to do, but I could guess. Under normal circumstances, I would never have done it, but considering he was blackmailing me, I thought it might be a good opportunity to find out what it felt like.

I wrapped my hand around his thick shaft, and lifted it up. It was amazing how I could actually get a good grip on his cock, unlike my own. When I jerked myself off, I only used three fingers. I needed my entire hand to actually encompass Jay's. I couldn't believe I was actually holding the cock of the man who humiliated me so much. The same cock that violated Tess in such a raw, primal fashion. The same cock that sunk deep inside of Tess' pussy, and shot its seed into her. Under my touch, it slowly grew, and grew, and I couldn't believe just how big it got.

"Having cute chicks touch my cock always gets me really hard," Jay whispered in my ear, and sent a shiver down my spine.

At full size, I was just barely not able to fit my hand around it. It seemed far bigger than it had in the video, and I wondered if it was even possible to fit that entire thing inside of someone. The shaft had several veins running along, and I ran my finger up the entire length, feeling the ripples and bumps.

The head was a work of art of its own. Big, and bulbous, with well defined ridge. I ran my index finger across it, and a tiny drop of liquid appeared out of the urethra. I dabbed it away, and used it as lubrication to make little circles.

"Oh god, you're a natural, Henry," Jay moaned, and his mouth was so close to my ear that I felt every word in hot breath on my skin. "Doesn't seem right to call you Henry anymore, does it? I'm gonna call you Henrietta from now on. You're such a good girl, Henrietta."

I ignored him, mesmerized by his massive dick. Through the zippers, I could just about make out his balls, shaved smooth, hanging between his legs like a medal awarded for manliness. It wasn't fair that a jerk like him was rewarded with such a magnificent cock, while I was left with nothing.

I grabbed the shaft again, and slowly started pumping. Every second I was in contact with that thing, I felt my own manhood just draining away, but I couldn't help myself.

"You're so pretty, Henrietta, keep going."

The doorbell rang, and ripped me out of my trance. I immediately let go of his cock, and jumped so hard, not even Jay managed to keep hold of me. What the hell was wrong with me? Disgust, and shame washed over me, threatening to drown me out. I was Henry, not Henrietta, and I was a man, and what Jay did was wrong.

Jay got up, tried squeezing his erection back into his pants, and failed. He walked towards the door, and opened it, hiding his lower body behind the wood.

"Oh, I've missed you, Jay," chirped Tess, and I tried sinking deeper into the leather couch. Under no circumstances did I want Tess to see me half naked on Jay's couch, still wearing her used underwear. She wasn't wearing her usual work clothes, instead wearing a very short skirt, tight shirt, and jacket.

"Hey, Tess, thanks for coming." Jay managed to tuck his cock back in his pants, and swung open the door.

"Oh man, you wouldn't believe what a creep my Uber driver was. He kept staring at my tits in the mirror the entire drive, and almost got into an accident. You should have seen his face when I flashed him my—Hey, what's Henry doing here?"

"Henry? Who's that?" mocked Jay, playing it up. I would have given anything to disappear at that moment. "I don't know any Henry. If you're talking about the slut on the couch, that's Henrietta. Say hello to our guest, Henrietta."

My throat closed up, and I couldn't bring out a single word.

"What's going on here?" demanded Tess, looking at me in confusion.

"Tess came here to get her lingerie back," explained Jay. "Don't you think it's the perfect time to return her things?"

"No," I cried out, finding my voice. "Please... no, not like this."

Jay swiftly moved over the couch, grabbed me by the arm, and pulled me up. "Come on, Henrietta, be a good girl, and return Tess' panties." His fingers dug into my flesh, and held me tight.

"Not in front of her, please," I begged. I would rather have died than have Tess witness my humiliation.

Jay didn't wait for me to act, but instead reached down with his free arm, hooked his thumb into the waistband of the panties, and yanked them down. I couldn't take my eyes off of Tess' face. The moment I felt the cool air brush against my exposed dick, her eyes went wide. She clapped her hand in front of her mouth to unsuccessfully suppress her giggles. The entire room was completely silent, save for Tess' muted laughter.

"Oh. My. God. Henry..." she snorted, and my heart shattered into a thousand little pieces.

"It's so small, isn't it?" added Jay.

Tears welled up in my eyes. I've known Tess for just about two years. She was funny, smart, and incredibly beautiful. I've had an enormous crush on her for over a year. I thought that maybe she felt the same way about me.

All of that was gone the instant Jay had pulled down my panties. I saw the expression in Tess' eyes. The same expression my first girlfriend had, when she saw me naked for the first time. The expression that told me that Tess stopped thinking of me as a guy at all.

Despite that, there was hope. Tess' initial amusement had faded, and she looked at me with concern, then at Jay, and then back at me. "Jay, we need to have a word. In private."

Jay let go of me, and all the strength I had left faded. My knees slammed into the floor, only slightly softened by the carpet. Tess and Jay disappeared into his bedroom, and I couldn't hold back the tears anymore. My whole body shook with sobs, while tears flowed down my cheeks freely.

I don't know how long the two of them were gone, but it seemed like an eternity. Tess found me still kneeling on the ground, crying, and shivering. She knelt down next to me, and gently wrapped her arms around me. She cradled my head, pulled me up against her shoulder, and slowly stroked my hair.