"Absolutely not," I said, arms folded over my chest. "There's no way in hell I'm doing that."

Gloria's mouth settled into a pout while her eyes turned pleading. "Come on, Peter, at least consider it! I've put a lot of thought into this." She held up a flesh-colored dildo with a mushroom head. "I made sure to buy a smaller size so it wouldn't be intimidating!"

Despite myself, I studied the sex toy a little more closely. It was about six inches long, and not quite as thick as my cock.

"It's not much larger than my finger," Gloria insisted.

"Bullshit. And I'm not going to let you film us while you're fucking me in the ass."

I could tell she was struggling to be patient. Her sigh was full of disappointment.

"But that's how we make our money," she explained as if I were a simpleton. "You wouldn't believe how many guys have a fantasy of being pegged. Some would pay for the privilege, while I'm offering to pay you!"

The mention of money reminded me how much I'd made from pretending to be Gloria's cuckold. My bank account was no longer being steadily depleted as a result of my unemployment. Now, I could sleep easier at night knowing I was earning some kind of income.

With my stare still fixed on the dildo, I grudgingly asked, "How much are you willing to pay?"

Though she pretended to ponder my question, I knew she'd already decided. Gloria had quickly proven to be a savvy businesswoman.

"Well," she said, drawing out the word, "I made a grand from fucking one of my fans and letting him come in my pussy. So I figure that's a fair amount."

I tried and failed to hide my surprise. "You'll give me a thousand dollars if I let you peg me?" When she nodded, I said, "That's a shitload of money, Gloria. Why would you do that?"

She tossed her hair over her shoulders and then trailed the dildo's tip along her visible cleavage. "I believe you're a wise investment. Since you and I have started working together, I've gained a ton of new subscribers, and the money's flooding in. I'm actually getting interview requests from adult entertainment streamers!" Her smile was almost giddy. "I'm making a name for myself, and you're bringing a lot of attention my way. I'm willing to make a financial sacrifice now in order to reap the benefits in the future."

I lifted an eyebrow at this revelation. If anyone had told me a few weeks ago that I'd be making money from performing sex acts on camera, I would have laughed. But now that I understood Gloria needed me in order to become more successful, I worked up the nerve to play some hardball of my own.

"I want a thousand," I said, "and twenty percent of the proceeds. After all, you're using my home for your studio." Waving a hand, I gestured around the guest room. She'd transformed it entirely, with the furniture moved all around and the lighting just as she wanted. Various cameras were set up from different vantage points.

It was Gloria's turn to be surprised. "Huh." A laugh bubbled up from her chest. "I didn't know you had it in you, Peter." Her expression was one of reluctant admiration. "Fine. A thousand dollars and twenty percent. Just remember, you're taking food out of a poor college girl's mouth."

I snorted at that. "I think you'll survive. And it's a fair price for giving you my anal cherry."

Gloria erupted into giggles, and I couldn't help joining in. It was strange yet pleasant, laughing with her as though we were friends.

But all too soon, her face grew serious and she reverted back to being my boss. I listened with more than a little trepidation as she explained how I should prepare for anal sex.

"We don't want any accidents, so you need to douche," she said before going into explicit detail about what that involved.

"Christ," I muttered, wiping a hand across my brow.

"Also, you'll need to wear this before we do the deed." She retrieved a butt plug from her purse. To my relief, it was black and sleek, with no jewel or faux-animal tail as a decoration. I certainly didn't need any more humiliation.

"And you'll be sucking my fake dick while I'm wearing a harness," Gloria rushed on. "Just for a few minutes."

"For God's sake!" I shouted. "Can you think of any other ways to degrade me?"

She merely closed the distance between us and gave my cheek a soft pat. "Who knows?" Her smile was deceptively sweet. "You might enjoy it."

And that was how I ended up in the spare bedroom a few nights later, naked and on my knees in front of Gloria. Though I realized my eye mask was all but pointless, I stubbornly refused to relinquish it.

And Gloria? She wore nothing but a strap-on. The harness was made of black leather, and despite my anxiety, I had to admit she made it look sexy. The dildo, however, now appeared formidable as it loomed out from her.

"I know you've been wanting this, baby." Gloria's tone dripped with a lust that made my dick pulse. I watched, transfixed, while she stroked the dildo as if it were a real cock. "Go on, give it a kiss."

Leaning forward, I planted a quick kiss on the dildo's tip. My reluctance made Gloria laugh.

"Come on, you can do better than that!" she teased. "Don't be shy."

I let her weave her fingers through my hair and guide me. With my tongue extended, I gave the silicone cock a lick. My saliva left a sheen along its length. 

"Mmm, yes, you like that, don't you?" Gloria's grip on my hair tightened. "Be a good boy and suck my dick."

I dared to wrap my lips around the cockhead. As Gloria encouraged me, I began sucking the dildo and taking more of it into my mouth. All the while, I sensed the camera recording me. I never lost sight of the fact that others would later witness my humiliation.

Gloria moaned and then gave a subtle thrust. To her credit, she didn't try to gag me with the cock. Once I realized I could trust her, I hollowed my cheeks and began bobbing my head back and forth.

"Fuck, yeah!" she cried. "You're a natural cocksucker, sweetheart!"

I knew I was shamefully hard. My erection wouldn't escape the camera's lens. Though I tried to tell myself it was because Gloria was naked before me, with those beautiful tits on display, I'd already begun to suspect that my arousal had more to do with her praise. Even as the woman emasculated me, I craved her approval. I wanted to put on a good performance not just for the money I'd earn, but to please her.

As promised, she made me fellate her fake cock for just a few minutes. The dildo was now shiny with my spit. Studying the toy, I was surprised at how large it had felt in my mouth. Of course, that did nothing to put me at ease when I was about to take it up the ass.

As if sensing my apprehension, Gloria smoothed my hair and then stroked my cheek. "I'll be gentle with you, pet," she told me. "Now get on the bed."

Feeling like a lowly animal, I obeyed her command, and she positioned me so one of the cameras had a clear view of my ass. After joining me on the bed, she spread my buttocks apart to reveal the plug's base.

"Such a good boy!" she said. "You've done a wonderful job preparing."

That was true. I'd made sure I was clean, inside and out, and I'd even shaved off the hair that circled my anus.

Gloria gave my butt cheeks a squeeze. "It's time to take this out," she said while grasping the plug's base. "I know you're aching for something bigger."

That was not true, but despite my anxiety, my dick remained hard. Gloria was gentle, taking her time until my ass surrendered the plug. I felt stretched open. The sensation led me to wonder how my hole looked on camera.

"That's so fucking sexy!" Gloria massaged my anus with a fingertip. I didn't have to look behind me to know she had lube at the ready.

"Just relax," she said. "I'm gonna make you feel so good."

And by God, she did! I let out a faint cry when her tongue swept over my hole. With her hands, she kept me spread wide, and I moved my legs even farther apart to help. Her warm breath and eager licking made me so aroused that I actually shivered. I never dreamed she'd be willing to do such a thing!

Gloria's tongue worked deeper inside me. As she fucked me in such a filthy way, her fingers traveled to my taint to deliver a blissful massage.

"Ah, fuck!" I groaned. Lowering my head, I noticed a strand of precum dangling from the tip of my cock.

After withdrawing her tongue, Gloria eased a finger into my ass. The plug had done its job, for I was able to easily tolerate the intrusion.

I heard the grin in Gloria's voice as she said, "I can't wait to fuck your tight little hole! Turn over, baby. I want to see your face when you take my cock."

Nervousness caused my dick to soften a little. Lying on my back, I watched Gloria apply ample lube to her index and middle fingers. She didn't have to instruct me to lift my legs and open myself wide; I used my hands, just as she had used hers, to spread my butt cheeks.

"That's perfect!" Gloria said. Her eyes glowed like burnished gold, and I noticed the flush of arousal had spread from her face and neck to the tops of her breasts. When she eased two fingers inside me, I gasped and tensed up.

"Relax," she urged. "I won't hurt you."

To my relief, there was no pain as she thrust those fingers in and out of my hole. Instead of withering, my erection returned, and I couldn't resist the urge to masturbate.

"Someone's getting excited!" Gloria said in a sing-song voice. "Now I'm sure you're ready."

I knew a camera was focused on my face, capturing my reactions. Another would record my pegging in intimate detail. Gloria brought the tip of the dildo to my dilated hole. Immediately, I felt the unyielding pressure.

"Don't forget to breathe." Her tone was low and soothing. "I'll take it slow, I promise."

I did my best to relax. The cockhead felt massive entering me, and I fought back a whimper. Gloria's eyes met mine; she waited until I gave a quick nod.

Then she pushed in a little deeper. Once the tip was all the way in my ass, the more slender shaft was easier to bear.

"We're halfway there!" Gloria said. She was focused so intently on being careful and not hurting me that a layer of sweat had formed on her cheeks. Again, I was overwhelmed by that strange need for her, along with immense gratitude. It all mingled together within my mind until it felt like love.

My nod was firmer this time, encouraging her to continue. With painstaking restraint, she finally bottomed out. We both laughed, unable to hide our relief.

"How does it feel?" she asked.

"Uh..." I struggled for the right word. "Different."

"And how does this feel?" She began moving her hips so she was fucking me with the dildo. I soon felt the toy applying pressure to my prostate. 

"Oh my God!" Suddenly, I experienced what I believed was the need to urinate. I'd read up on pegging beforehand, so I knew the sensation would subside. And I also knew Gloria was penetrating me at the perfect angle. 

With each thrust, she released a moan. I stared up at her, helpless and still completely hard. Her tits swayed as she pumped her hips. Those long, gorgeous locks tumbled past her shoulders. Seeing her this way, in complete control, I paid no mind to any lingering pain.

She reached to take hold of my cock. By this point, I was practically panting. "Fuck me!" I begged.

Gloria stroked my dick while claiming my hole at a faster pace. My cries grew high-pitched, almost girlish. A heavy warmth settled beneath my skin, radiating from my scalp all the way to the soles of my feet. Despite the heat, I shook as if I were freezing.

"I'm... oh fuck, I'm gonna..."

"Be a good boy and come!" Gloria drove the dildo into me, again and again, until my mind reeled from the pain and pleasure. Her hand was relentless on my cock. "Show me how much you love being fucked in the ass!"

Our eyes locked, and with my stare, I pleaded for release. I seemed incapable of bringing it about on my own. 

She shifted her hips, ever so slightly, and homed right in on that magic spot a couple inches inside me. I shouted from the intensity of my orgasm, while Gloria giggled at the sight of my cum spurting forth to dot my torso.

Even as I came down from the climax, I continued groaning and gasping for breath. She kept the dildo buried in my ass for a few moments longer, then carefully withdrew. I winced when the tip popped free.

"Holy shit!" she exclaimed while sliding her hand along my thigh. "You came so fucking hard!"

I couldn't help but laugh. "I did, didn't I?" My stare dropped to the cock which had just claimed my anal virginity. It was shiny with lube, and again, I marveled at the way the toy felt much larger than it looked.

"This is going to make us a fortune." She climbed from the bed and went to deal with the cameras. "You were smart to insist on twenty percent."

I lay there while my breathing returned to normal and the ache in my ass faded. "So what's next?" I asked.

Gloria looked over at me, still sporting that cock as though she were proud of it. Maybe she was.

"Oh, you're going to love what's next, Peter."

I raised my eyebrows, unsure of whether I should believe her.

"Our fans love watching me control an older man, of course." She gave the dildo a cursory glance. "But more than a few have started to request something different, and I'm willing to oblige them."

"Something different?" I propped myself up on my arms. "What do you mean?"

For the first time, Gloria's smile turned sheepish. The girl seemed almost shy, as if she were about to make a confession.

"What I mean is..." She took a dramatic breath, keeping me in suspense a few seconds longer. "The fans want to see you dominate me."