Not a Man Ch. 04

His finger traced circles around my sphincter. He stopped once to apply more lube, and I just sat there, frozen in terror.

"You gotta relax, Henrietta," said Jay.

"I don't think I'm ready for... that," I told him.

"Oh, I know you're not ready for my cock, as much as you want it. We'll need a lot more practice before that. It's going to be a finger today, alright?"

A big weight lifted off my shoulders. I released my breath, and the tension faded from my body. Immediately, Jay's finger popped into my asshole. I let out a yelp, but it was too late. His finger was in my hole. It felt weird. He pulled his finger out halfway, and then pushed it back in. Weird, unusual, but... exciting.

He pulled me in for another kiss, sliding his finger in and out of me a little faster. It was hard trying to concentrate on both things at the same time, and I just let the sensations wash over me. Suddenly, a third hand made an appearance, grabbing my dick. Tess started stroking, instantly rekindling the denied orgasm from earlier.

White hot energy burned through my body, and I came hard. My cock twitched, and shot a jet of cum. The muscles in my ass tried to squeeze shut, and I felt Jay's finger more pronounced than before. It actually started to kind of hurt, until my muscles were back under my control, and I relaxed.

Jay pulled out, and released me from his embrace. I slumped onto the couch, out of breath. The puddle on Jay's shirt was bigger than I would have imagined. Aftershocks of my orgasm still pulsated outward from my balls. My sphincter burned slightly, but it wasn't too bad.

"Damn, Henrietta, you're gorgeous," remarked Jay.

I felt gorgeous, for once.

"Damn, I'm really horny now," said Tess.

"Come over here, then."

Jay pulled her up on his lap, in the same position I had been in just moments before. Had I looked as graceful as Tess? Probably not.

"I bet Henrietta is eager for a demonstration of what she's in for," Tess giggled.

I considered it, but realized that I had had enough for the day. I needed to be by myself for a while, and process the entire tumultuous day.

"Actually, I'd like to go home, if that's ok."

"Sure. I don't think I'm going to need your help to fuck the shit out of this slut."

He pulled Tess' shirt over her head, and started squeezing her fabulous breasts. He wasn't even looking at her while he did it. He was looking at me, and no doubt getting off on my anguish.

"She's gonna need her goodie bag," said Tess, and her breasts bounced slightly.

"Oh yeah. You take care of it, while I throw this shirt into the laundry."

"What goodie bag?" I asked, staring at Tess' fabulous tits.

Tess grabbed the bottle of lube off the coffee table, and I followed Tess back into the bathroom. My legs were weaker than expected, and I braced myself on the walls to keep from stumbling more than once. She thrust a purse at me. I looked inside, and saw it was full of dildos. Four of them. I was beyond caring. I just wanted to get out of there.

"They're for you to practice with," she explained, and stuffed the lube in there. "They're different sizes. Start practicing with the small one, and work your way up to the biggest."

"Practice for..." I realized what for before I finished the sentence.

"For Jay's cock," finished Tess, anyway. "I'd do it myself, but you're going to be alone for the weekend."

"Alone? How?"

"We're going on a trip until Monday."

"Where?"

"None of your business, actually. A romantic getaway. We've already had it planned for weeks."

"Oh." I didn't exactly want to spend more time with Jay, but I somehow felt disappointed nonetheless.

"It's going to be great. We're gonna spend the entire weekend fucking, I think. You better make sure to practice, so Jay can fuck you once we get back, okay?"

"Okay," I responded meekly. "Should I put my old clothes back on?"

"What do you think?" she smirked.

"Guess not," I sighed.

I picked up my old pants, and transferred my wallet and keys from my pockets to the purse. I stuffed the clothes into the bag, and headed back into the living room. Jay was standing in the middle of the room, buck naked, his cock fully erect. His massive, beautiful cock. He pumped it a couple of times.

"Why don't you kiss it goodbye?" demanded Jay. He had gotten rid of the lipstick smudges in the meantime.

I felt helplessly drawn to it, like a moth to a flame. It was so big, I didn't even have to bend over that much to be able to place a quick peck on tip of his cock. A drop of salty precum touched my lips. For just a moment, I thought about opening my mouth, and... no, I already had done enough for one day. No, I meant that I didn't want to suck a guy's cock, I reprimanded myself, but even in my head the argument sounded weak.

"We'll see you Monday," he said.

Tess went down on her knees, and started sucking his dick, the moment I stepped away. Noisily, she slurped on it. Jay grunted in satisfaction, and looked at me, gloating. He didn't even have to mention that the love of my life was vicariously fellating him. Spit dribbled down Tess' throat, as she deepthroated a significant length of his cock. She was better, and more eager, than any pornstar I've ever seen.

With my heart broken just a little bit further, I left the apartment. Walking on heels didn't seem to that big of a problem anymore, in the face of everything else.

On the fourth floor, the elevator stopped, and a young woman in her early twenties got on. I definitely recognized her. How did she manage to always catch the elevator at the same time as me? She had long, blonde hair, and looked like she was about to go to a party.

She considered me, head askew. A flicker of recognition flickered on her face, and she smiled at me. The elevator doors closed behind her. I wondered what she was thinking about me, dressed in women's clothing, in full makeup, carrying a purse full of dildos in one hand, and a bag of clothing in the other.

"You're the cum guy, right?" she said.

"The what?" I asked, confused.

"The guy with the big stain on his back that smelled like cum."

"Oh. Yeah." Fucking perfect. Even Henrietta was better than "cum guy."

"Nice clothes." She looked down at my shirt.

"Thanks." I didn't even have to look to see the damn teddy bear, emblazoned with the words "Little Love Muffin." Maybe there was something worse than "cum guy" after all. "You should see the panties."

The woman raised an eyebrow. I had no idea why I even said it. With her index finger, she lifted the hem of my skirt, leaning sideways to look underneath it. A grin spread on her face. Except, it wasn't a malicious grin, like Jay's. Or a wicked grin, like Tess'. She just looked vaguely amused.

"What's your name?"

"I'm He—"

I cut off. I had been about to say Henry, but that wasn't really true anymore, was it? It didn't feel right giving her my old name, while looking so much like a woman. But I didn't want her to know me as Henrietta either. That was a stupid name.

"I don't know," I answered instead.

"I'm Vee," she introduced herself, and held out her hand.

I set down the bag, and shook it. "That's a weird name."

"Yeah well, at least I have one," she countered.

I had no response to that.

The doors of the elevator dinged, and a group of men and women in their late fifties entered. It felt like they were intruding on some special moment. Vee spun around quickly, as if we'd been caught doing something illegal. Quite a few of them regarded looked at me with disdain. They probably thought I was a hooker, and I didn't blame them.

The elevator reached the garage, and the doors opened. Vee turned around, and flashed me a brief smile, before disappearing around the corner.

Sitting down behind the wheel, the burning sensation of my ass made itself noticeable again, but it was bearable. It did make the trip back home seem a little longer than it should, though.

Once I was back in my safe space, I took off the shoes, deposited the bag and purse on the floor, and threw myself on the couch.

What a fucking day of ups and downs it had been. Thank god it was finally over.