Not a Man Ch. 02

"Shhh, Henry, calm down. Everything's gonna be alright, okay?"

What had she said to Jay? Was Tess going to rescue me from my predicament? Maybe she yelled at him, and threatened to call the cops. If I had Tess on my side, they had to believe me, and then the cops would put Jay away. It would be just us again, then. Just Tess and me... except, what would be the point? I wasn't a man anymore, at least not to her. My tears stopped, at least, and I felt slightly better.

"Are you going to help me?" I whispered.

"Yes, Henry," she whispered back, and kissed the top of my head. "I'm going to help you become the prettiest girl you've ever seen."

Her words hit me like a shotgun shell. I wanted to cry again, but I didn't have the strength left in me anymore. With a clink, Jay set down another full glass of wine on the table.

"Babe, I'm gonna need you back in the bedroom," Jay grunted.

Tess let go of me, and I reluctantly let her get up. Jay tossed me a light gray blanket, which I managed to just barely catch. Tess took another look at my little, flaccid cock dangling between my legs, shook her head, and then left.

"You made me really horny back there, Henrietta. I'm gonna have to fuck Tess especially hard, but I'm sure you understand. Anyway, I've refilled your wine, and feel free to watch anything you want," he instructed, nodding at the TV remote.

After he disappeared in the bedroom, I was all by myself. I gathered myself, sat down on the couch, and wrapped the blanket around me. Jay had left the door to his bedroom open, but I couldn't see around the corner. Yet again, he was about to have sex with the woman of my dreams, and I couldn't do anything about it.

I decided that I had been humiliated enough, and finally took off my bra, tossing it on the ground next to the panties. The blanket was warm enough that I didn't need any clothes, and I just assumed that Jay would get upset if I put them back on.

Trying to take my mind off the situation, I grabbed the glass of wine off the table, and turned on the TV. Except, there was nothing good on. Commercials, commercials, news reports about a hurricane in the Philippines, sports, reruns... garbage, after garbage, after garbage. Although in my state of mind, I doubt anything would have caught my interest.

I got my phone out of my pants, and unlocked it after several failed attempts, caused by my hands shaking too much. I could have done anything, like call the cops. Except what would I tell them? Jay was trying to turn me into a girl? The cops would just laugh, undoubtedly. I couldn't tell them about the blackmailing without implicating myself, either. The situation was hopeless.

Somehow, the glass of wine had emptied itself, and I felt the effects of the alcohol setting in. Wrapping the blanket around myself like a robe, I headed towards the kitchen. The half empty bottle of wine stood on the counter, and I simply grabbed the entire thing, taking a long swig.

The kitchen itself didn't look like it got used much, except for the microwave. The glass stovetop looked untouched, and I missed the ordered chaos of my own kitchen. Out of curiosity, I opened the fridge. Half of it was filled with bottles of beer, and water, and the other half with a small assortment of fruits, meats, and bread.

Jay must not spend a lot of time at his apartment, I deducted, otherwise it would have been stocked better. From what little I knew of him, he was probably out at bars, picking up women. No, not women. Tess. That thought warranted another mouthful of wine.

On the way back to the living room, I heard loud moans coming from the bedroom, and stopped dead in my tracks. The door to the bedroom was open, and Jay did say that I could watch anything I wanted. I crept closer, and peeked around the corner.

Even though I knew what to expect, the sight of it didn't hurt any less. Tess rode Jay cowgirl, squeezing her own tits, and moaning like an animal. She had a tattoo on her shoulder blade that I had never seen before. It was some Egyptian symbol that I've definitely seen before, but couldn't recognize.

My eyes trailed lower, down to her spectacular, cute butt. Tess bounced up and down on Jay's massive cock with a fervor I've only seen in porn. Every time Jay's dick plunged deep into her, the wet shlicks were accompanied by Tess' moans.

Seeing it in front of my eyes was a hundred times worse than seeing it on Jay's tiny screen, but I couldn't look away. Instead, I took another deep draft from the bottle of wine, and leaned on the doorframe for support. Was that going to end up being my fate? Jay wanted to turn me into a girl, did that mean he was going to fuck me like that?

Tess let out a guttural moan. Her toes curled, and muscles flexed all over her body. She threw back her head, and screamed. It was the single most erotic thing I have ever seen, but all I could think about was the fact that I'd never make a woman that happy.

Disgusted, ashamed, and drunk, I stumbled back to the living room, and plopped down on the couch, wrapping the blanket tightly around me. I took another swig, and emptied the bottle.

"Here you go, Mr. Table," I muttered, set the bottle down, and giggled.

Not long after, Jay came out of the bedroom, completely naked. He walked to the kitchen, his thing flopping between his legs, and got a bottle of water out of the fridge. He twisted it open, and almost emptied it in one go. I was surprised how hairy he was under his clothes. I had always imagined that he'd be one of those bodybuilders who shaved his legs, but he had a sizeable patch of hair on his chest, with a trail running down his stomach. Only his pubic area was shaved.

"Did you like our little show?" he inquired, coming to a halt in front of me.

"No," I responded, but I couldn't make heads or tails of my own emotions. Especially not with Jay's cock right in front of my eyes. It was still wet, glistening with Tess' juices.

Tess came into the room, wearing one of Jay's shirts like a dress. Her hair was in disarray, and her face slightly red.

"Ugh, put one some clothes, you pig," she reprimanded Jay, and playfully swatted him on the arm.

Jay shrugged, and disappeared into the bedroom. Tess threw herself down on the couch, leaned back, and stretched her arms. She let out a long, drawn out sigh, turned to me, and said, "You have no idea how good it feels to get fucked like that after a stressful day."

Her hard nipples poked through the thin fabric, and I was pretty sure she wasn't wearing anything underneath.

"Hey, you know what would be fun?" she mused.

"No," I replied.

She leaned forward, grabbed her purse off of Mr. Table, and rummaged around in it. Triumphantly, she pulled out lipstick. Without any warning, she jumped up, and straddled me. Two days earlier, that would have been the stuff of my dreams. Just her, and me, but maybe without the blanket between us.

Tess sat down on my hip, and fortunately she didn't weigh too much. I instantly got an erection, realizing there maybe just two or three inches separating her pussy and my dick. And yet, it was a nearly insurmountable distance.

"Hold still," she commanded.

The realization that I was as physically close to her as it was possible to be, but about as far as possible from what I wanted made, me want to scream in frustration. I closed my eyes to keep the tears from flowing. Tess grabbed my chin, and I let her guide my head slightly up.

"You having fun playing with your doll?" asked Jay, and I felt him sitting down on the couch.

"I don't like the name Henrietta," she replied.

"Really? I thought it was pretty clever."

"It's not, and it's also too old fashioned," Tess explained. She dragged the lipstick across my bottom lip.

"So what do you suggest?" Jay asked, talking as if I wasn't even there.

"Honestly, I think we should let Henry decide. I mean, it's going to be her life from now on, right?" Tess suggested, and I realized it was the first time Tess had said "her." Was that really going to be my life? Tess dragged the lipstick across my upper lip.

"I guess," said Jay, who didn't sound too enthusiastic about it. "But until she's ready, I'm gonna call her Henrietta."

"There, it's done," announced Tess, and climbed off my lap.

I opened my eyes, but couldn't see the difference.

"Wow," marvelled Jay. "Amazing what just a little lipstick can do."

"It's not the perfect color for her, but it's the best I had on me."

"Can I see?" I asked.

"Yeah," Tess replied, and rummaged around in her purse again. She drew out a small, round case, and handed it to me.

I opened it, and found the top half to be a picture of a woman. I blinked, and realized that it wasn't a picture at all. It was a mirror, and I had been looking at my own reflection. Jay was right. I had never realized it before, but the bright lipstick on my lips made me look at my face in a different way. I knew I was never the kind of person with a chiseled jaw like Jay, but now I looked downright feminine, with soft cheekbones, and slender face, and short, dark, curly hair. On top of it all, my eyes were as red as my lips from all the crying.

I snapped the mirror shut again, and what strength I had left deserted me.

"I want to go home," I pleaded. I was more than ready for the day to be over. I just wanted to be in my own bed, in my own room, in my own apartment.

"I don't think you're in any condition to drive," declared Jay, sounding like he was about to suggest I sleep in his bed for the night.

"I can take her home, I need to check up on Mom, anyway," volunteered Tess.

"You sure?" Jay sounded disappointed. "Alright. Go get dressed, Henrietta."

Tess walked back to the bedroom, and Jay followed her. I threw open the blanket, and stumbled to the pile of clothes on the ground. It seemed like a lifetime since I had worn them, and the jeans felt rough on my skin.

From the bedroom came the unmistakable sounds of a second round of fucking. I headed to the kitchen, and searched around for more wine, coming up empty. I grabbed one of the bottles of beer out of the fridge, and opened it. Moaning, grunting, and screams rang through the apartment, although it didn't last nearly as long as last time. By the time they were done, the bottle was empty. It had been surprisingly good, and I made a mental note to get some of my own.

"You ready?" asked Tess, several minutes later, and fully dressed.

"Yeah."

"Let's go, then."

Tess headed out the door, and I followed. Well, I tried to follow, anyway, because I ran into the doorframe with my shoulder.

"Jeez, how much did you have to drink?" asked Tess.

"Not much," I lied.

"Come on, let me help you."

Tess put her arm around me, and steadied me. The elevator doors dinged open, and Tess guided me inside, pushing the button for the parking garage. On the fourth floor, the elevator stopped, and a young woman in her early twenties got on. I thought I recognized her from somewhere, but couldn't remember where. She had long, blonde hair, and looked like she was about to go to a party. She looked at me curiously the whole way down, and I couldn't figure out why, until I remembered I still had lipstick on.

The elevator dinged again, and we got out in the parking garage. The young woman went a separate way with a parting smile. I dug around in my pocket for the car keys, and handed them to Tess, before collapsing in the passenger seat. The engine roared on, and we started driving. Everything seemed to be going in slow motion, and sped up at the same time.

"Where do you live, anyway?" inquired Tess.

"Acacia Drive, over in Middleton," I answered.

"Oh, that's pretty far."

"Sorry," I apologized.

"It's ok, it's not a problem."

"Why are you doing this to me?" I blurted out.

"Because you're drunk, and can't drive."

"No, I mean with Jay, and me," I clarified, not wanting to actually say the words "turn me into a girl" out loud.

"Jay told me how you tried to blackmail him. Really, what were you thinking?"

"I wasn't... I—"

"And then, when I saw your little dick, oh god, it was so pathetic. Jay told me what he's planning on doing to you, and it just sounded so fucking hot. I get wet just thinking about it, you know. The thought of slowly taking your manhood away, and turning you into a little, cock loving slut is so fucking hot."

I couldn't believe the words coming out of her mouth. She had been so nice to me, holding me when I was crying, that I didn't really believe she wanted to go along with Jay's plan.

"But... you can't," I protested, weakly.

"Oh believe me, we can. I can't wait for the moment when you're finally ready, and Jay is going to slide his entire cock in your little boy-pussy, and you're gonna moan, and beg for more."

We drove the rest of the way in silence. Tess' words bounced around in my head, until I thought I was going to be sick. If you had asked me a few hours earlier if I thought Tess could be in any less than perfect, I would have said no, but now I wasn't so sure anymore. I regretted drinking so much.

The last things I remembered, were Tess asking me if that's the building, and her opening the front door, but nothing else.