A Bully Caged Pt. 04

She returns my nod and grabs a ballgag off the shelf to hand to me. It's black, and I roll it in my hands before reaching around to push the ball into Wes' mouth.

I stand to latch it tight. His cheeks bulge around the gag, and a drop of spit falls to the floor already. His mouth is just an accessory today.

I grab a fistful of his hair and pull him to standing position. His cock is already turning purple in his cage, and I wonder if his recent release has only made the torture worse. When you have hope for an orgasm, the next denial intensifies.

Sasha, just as we planned, takes off her robe on the other side of the room. My breath catches in my throat. Although I've recently been experimenting, to say the least, I remain resolutely bisexual. Sasha's breasts are large, and her dark brown nipples are erect. She has a trimmed bush framed by wide, stretch-mark-kissed hips. Her skin looks supple and soft. This is the woman that has had Wes pining over her only weeks ago.

I wave to Ms. Simmons to take care of Wes as I move towards Sasha and join her on the other side of the table. She grabs my hand in silence and puts it around her hip. She's softer then Wes, but in many ways I miss the lithe musculature of his waist. If Sasha is water, Wes is wood.

Together, Sasha and I watch Ms. Simmons with Wes.

First, she positions him on the other side of the table, facing us. We are only a few feet away, and I swear I can feel the heat radiating off of him. His cheeks are flush, and the prior drop of drool is joined by another that lands on the table.

Ms. Simmons grabs a set of three glass dildos, each bigger than the next, and after putting them next to Wes, it only takes a bit of teasing with her fingers before Ms. Simmons is able to ease the tip of the smallest into him. It's only five inches, and it's narrow. As it pushes into his ass, Wes moans around his gag. It's the same deep, guttural moan that he lets out when his brain is turning to mush.

Sasha reaches down and touches my cock through my robe. It's hard, and she silently palms the head and begins to rub in circles, gliding the satiny fabric across my dick.

Fuck.

Ms. Simmons quickly switches to the next dildo, and although the first was small, this one is larger, clocking in at six inches. It's somewhat cone-shaped, forcing the entrance of his ass to accommodate more and more with every inch.

Sasha removes her hand from my member, leaning forward to pull off Wes' blindfold as the medium dildo bottoms out. Wes blinks as his eyes adjust, but when he recognizes Sasha, he stares, fixated on her. His cheeks redden.

He tries to speak through his gag between pants, but it comes out as muffled nothing.

Sasha smiles and winks at him. "Hey, Wes," she says, her voice dripping honey.

Ms. Simmons pulls the dildo a few inches out before sinking it into Wes again. He groans, and his face is bright pink from arousal and embarrassment.

"I haven't seen you the past few weekends," Sasha says. "Is this what you've been busy with?" As she speaks, Sasha pushes past the folds of my robe and pulls out my dick. It's erect, and the veins that run up my shaft are swollen. She holds it with a firm grip, waving it at Wes.

He blinks, his eyes darting between my cock and Sasha's steady gaze. Ms. Simmons picks up the pace and is now gently fucking Wes, aiming down to hit his prostate.

"You know, I really was going to give you a chance some day," Sasha says, continuing to massage the length of my shaft. "You had been such a good boy, standing guard outside of that closet."

Wes' eyes are full of emotion, fluttering when Ms. Simmons gives an especially hard thrust.

"At first I thought about just giving you a handjob or something one day as a reward for being so obedient," she says, " and then I thought maybe you'd be able to be my cleanup crew. I *do* love having my pussy eaten after being filled."

Wes looks up at her, a glimmer of hope crossing his face.

"Then I finally decided that it was all too cruel," Sasha says, lowering her voice and nodding. "You saved my ass so many times, turning people away and making sure me and my boyfriends were never interrupted. A real lifesaver."

Wes nods back, another string of drool falling.

"I was going to fuck you Wes," she says. "Really. As a huge thank you. Do you want this pussy, Wes?"

Sasha begins to finger herself.

Wes nods again, this time faster, and he tries to talk again.

Sasha cuts him off. "But this confirms a couple things for me," she says. She sinks to her knees, and she eases my robe off. Ms. Simmons is the only one not completely naked now, but as she fucks Wes, the knot holding her robe closed is slowly slipping.

My dick is at full mast, and it sways when my robe falls.

"I don't think you want to lose your virginity to me," Sasha whispers, as if she's confiding in Wes.

Wes tries to speak again, but fails.

"No, no," Sasha says, fondling my cock. "I think you want to be a slut *yourself*."

Wes shakes his head, but with a dildo pumping in and out of his ass, he isn't very convincing.

Ms. Simmons pulls the medium dildo out of Wes, and replaces it with the largest. This one clocks in at eight inches, and it's cone shaped as well, meant to train Wes up to any girth. He squeals at first, but it's clear from his expression that the pain disappears after only a moment.

Sasha turns and wraps her lips around my dick in one smooth motion. Wes gasps around his gag as she swallows inch after inch of my length, her hot throat widening to accommodate my size. She looks up at me. Her eyes water, and tears stream down her cheeks as she begins to bounce, burying me again and again in her tight throat.

Ms. Simmons speeds up the dildo to match Sasha's pace, and Wes shakes with each thrust.

Sasha gags, but she doesn't pull back. She licks my balls, letting each time her throat spasms stimulate me. It's my turn to groan.

She pulls back, and her tears are falling as she smiles. "This cock is a good choice, Wes," she says, "I can see why you're choosing this over pussy."

Wes shakes his head, clearly humiliated, trying and failing to make one last assertion of his straightness.

Ms. Simmons, in response, spanks his ass again. He mewls. "I think he's ready for you, David," she smiles, pulling out the dildo stretching his hole.

Sasha spits on my dick one last time before I walk around the table. Wes watches me, and there's a moment that we make eye contact. His eyes flutter again. He's ready.

"All this time you spent listening to me through the door--gagging on dick, yelling about how humongous some of those guys were--you never were going to be one of them," Sasha says, "you were meant to be... you were *born* to be a slut like me."

Wes breathes heavily. He has no response. Ms. Simmons steps back to allow me access to Wes, and I see his ass in all of its glory. His hole, so pink and tight the last time I saw it, is gaping and dripping with lube. His legs are spread and quaking, capped off with bright red cheeks. A bead of sweat rolls down his right thigh.

Sasha is kneeling in front of him, and is holding his hands in hers. "You're doing great, Wes," she's telling him.

Ms. Simmons nods. "Are you ready to be fucked for the first time, sweetie? She takes off and discards her robe, walking around and kneeling to join Sasha in front of Wes.

Wes hesitates, and then he nods.

I see his hole, open and soft, waiting for me.

Then I hesitate myself.

"Take off his ballgag," I say.

Confusion flashes across Ms. Simmons' face, but she does so, unbuckling the latch and placing the gag to the side.

Wes moves his jaw as it's freed. He wipes the spit from his lips on his shoulder. "Thank you, sir," he says.

"I'm not going to fuck you until I hear you say please," I say.

I love to hear him beg, but even more, I need him to do this in front of Sasha and Ms. Simmons, the two women who he's been most enamored with in his whole life.

Even his shoulders and ears turn crimson.

"Please do it, sir," he says, looking down.

"No," I say, "ask me to take your virginity. Ask me to fuck you until you lose your mind. Ask me to fill you with cum."

Wes stops. For a moment, I'm not sure if he's going to say it. But he needs to get over this hill.

"Please, sir," he says, "please fuck me. Please fuck my brains out. Please fill me up."

I grab his hip with one hand, and I guide my cock to his hole. The head of my dick fits in him smoothly.

Fuck. He's tight, and the lube and spit make for a magical combination as I push centimeter after centimeter inside him. I'm halfway now.

"More," I say.

"Please fuck me like a whore," Wes moans. He's getting into it. "show me I'm yours. Make me take every inch, and then make me take more."

My dick feels like it's being engulfed by a cloud. "You're a good boy," I say. "Show these women how good you are."

Wes pushes back, taking another inch. "Please show me I'm a good faggot--fuck!" He exclaims. A piddle of precum is flowing from his cage. "Show me how I'm made for this..."

He's turned his eyes away from the women now.

I reach a hand around his throat and choke him, simultaneously turning him to face Sasha directly. She's smiling.

"*This* is the reward you deserve, Wes," she says. "You would have been completely lost with a pussy. You needed someone else to do the fucking for you."

Wes whines in response, partially due to Sasha, and partially due to the constant pressure I'm applying. Every time he is more humiliated, he becomes more aroused. I'd find it funny if it didn't turn me on so much.

Finally, he takes my cock to its hilt, and I can feel his blazing hot ass cheeks on my lap. He shakes, and his no-longer-virgin hole clamps down a few times on the base of my rod.

Then I begin to pull out and carefully thrust back in. Each time I'm almost out, it feels like his ass is pulling, sucking me back in, crying out for more. I start slowly, making sure that Wes loses his virginity in a way that cements his love for cock. I don't just want a tepid response; I want Wes to be excited--ecstatic--the next time he gets the privilege of having a dick in him. So far, he's responding better than I could hope for. He's loosened up, and I begin to put more force into my hips. Holy shit, he feels amazing.

Meanwhile, Ms. Simmons walks to her wall of sex toys, and grabs a bundle off the lower shelf--a strap-on. She steps into it, one leg after another, and as she lifts each leg, I can see the shine of arousal on her pussy. She might be doing this for me, but Ms. Simmons gets off on it just as much as me and Wes. The strap-on fits her perfectly, and its cushioned nylon straps are tightened until they are secure.

Sasha peers back at her, and as Ms. Simmons begins to approach again, Sasha gets up from kneeling to step to the side and instead lean on the table, her breasts resting on its surface. She and Wes are shoulder to shoulder, next to one another but facing opposite ways.

There's no time for Wes to react before Ms. Simmons is behind Sasha, guiding the dildo into her with one hand. She wastes no time. Sasha whines, her folds being pushed apart to accept Ms. Simmons' plastic beast.

"Oh, fuck," Sasha gasps, her eyes widening. "Your dildo is huge."

"Thank you, sweets," says Ms. Simmons. "I bought it custom for Wes, but I think he's found a new toy."

Wes locks eyes with Ms. Simmons and moans as I fuck him. My balls are bouncing against his smooth skin, and his hole is tightening around me in rhythm as if it's trying to wring me dry. One of these days, I'll make sure to pound Wes as he's facing me--I'll grind against his prostate as he stares into my eyes--but for now, it's perfect that I'm fucking him doggystyle. I'm not sure if I could hold back if he looked at me as he said all the dirty things and made all the lewd noises spewing from his mouth.

"Breed my asshole!" He shouts, finding his voice again as if on cue. "Please, please fill me up with your cum. Please fill me..."

With the willpower of a monk, I hold myself back from cumming. I need this to last just a bit longer.

I've been distracted by Wes, but now that I look over, Sasha is getting full service as well. Ms. Simmons is holding her arms as leverage, and driving the huge plastic dick to its limit. Sasha's eyes are rolling, and a soft, sensual noise escapes her. She was meant to do two things today: solidify Wes' descent into being a bonafide faggot, and to give him a partner to be fucked alongside. However, I think she's getting lost in the moment, and she is now almost as cockdrunk as Wes. Her eyes are unfocused, and her hair is unkempt.

"Thank you..." she groans.

Ms. Simmons speeds up in response. Her own tits are bouncing as she plunges the dildo into Sasha again and again, and we make eye contact as a drop of sweat falls from her jaw. She's filled with lust, and I see that she would devour anything--anyone--put in front of her right now. I have a good teacher.

"I'm going to--oh, God, I'm going to cum," says Sasha.

Wes practically screams. "Fuck! Fuck! Me too!" He exclaims.

It's Wes' voice that puts me over the edge. I let out a moan of my own without thinking--I realize that I've been vocalizing my own pleasure through the whole session without thinking. "I'm--I'm going to finish too," I manage to say.

"Thank you, sir," Wes moans. "Give me your cum..."

The first spurt of cum that I deposit in Wes is gentle--but I quickly realize that the first pulse is simply the tremor before the earthquake. My knees almost fold in on themselves as a something shifts in my core with the second surge of semen. I feel blood flow faster, and without ceasing, wave after wave after wave of cum escapes me, each trying to push past the one before it. I feel shivers and tingles of euphoria up and down my body, as if I'm being turned inside out with pleasure, and I can't contain myself from letting out another sound of pleasure.

As I orgasm, I feel Wes' entrance constricting my dick, and he begins to shake. He releases a shapeless, wordless moan that originates from deep in his belly, growing until it tears its way out of his mouth. I hear the splatter of his cum below him--this is the first time he has cum with just his ass as far as I know, and it's consuming him, gripping him by his throat and pulling him deeper. I don't touch his cage. I don't want him associating this feeling with anything other than the sensation of his ass being filled.

When Sasha cums, she breathes through her teeth with a low, throaty groan. Ms. Simmons does not slow down, and it seems to me that Sasha's own pleasure is only growing, an orgasm on top of an orgasm. She's plastered in sweat, and her curls bounce against her temples and forehead before dancing away again. I can hear her wetness as she melts back against Ms. Simmons.

We slow, but it's not until many minutes later that we completely stop--steeped in post-orgasmic bliss, we simply continue in slow, gentle motions, as if we were all pantomiming what it would be like to make love, but cannot reach full capacity or speed.

Wes has emptied me, and Sasha is drifting in and out of a fugue state, acting as if reality is only a temporary state.

***********************

Now that Wes has taken me, and I've taken him, the next morning is strange. He's been nicer recently, but now he is actually polite. He makes hashbrowns, and he serves them to me with avocado. *Avocado*.

Only weeks prior, Wes would have called an avocado a gay fruit, and now he's letting me cum in his ass and serving that gay fruit to me on a silver platter--no pun intended.

Sasha and Ms. Simmons are eating toast with tangerine jelly, spreading it with margarine. They seem content, sitting across the table and doing a crossword. After Sasha has stayed the night, I briefly wonder if she plans on staying longer, but that's not a concern for now--for now, I have to plan for Wes' next step--I have to make sure Wes reaches his potential as the greatest gay slut ever to grace God's green Earth.

***********************

Sorry for the long delay--I took a long break from social media and erotica, but I'm back and better than ever!

Let me know in the comments what you think Wes' next step should be! Should he start hypnosis, gloryhole training, or be made to visit a gay sauna? Drop your thoughts alongside any other ideas in the comments.

CandleLitTrail