Submitting to Love Pt. 02

''Lick them clean. I want them to shine. How does it feel to worship your mistress's boots?"

"It is a pleasure and privilege to bow before you and clean your boots mistress," I said between lapses.

"On your elbows, ass up."

I got into the ass-up position as Jess walked around to inspect my ass. She gave several light tabs on the butt plug with her leather paddle.

"How does your ass feel slave?"

"It feels stretched and hungry for more mistress."

She pulled on the plug, beginning to stretch my whole open again. I calmed my breathing, trying to anticipate her next move.

"When was the last time that you came."

"Um, about two weeks ago, since running into your mom at the store, Mistress."

She began to squeeze my balls as she continued to tug on the butt plug, enjoying torturing me. She pulled harder on the plug as my ass opened and stretched around it. Removing it fully, my ass hole tried to close, but was left gaping slightly.

Jessica inserted three lubed fingers, beginning to massage my prostate. She released my balls and began to swat at my caged cock, watching it swing back and forth.

Every press to my prostate sent waves through my body, as per-cum flowed from my cock. I was on the verge of coming, but every swat to my dick pulled me back from the edge, leaving me sexually frustrated, and I fucking loved it.

"Is my pet actually enjoying this?"

I hadn't realized that while she fingered me I was rocking my hips into her, trying to press her fingers harder against my prostate.

"She, Mistress," I said, panting in frustration from her removing her fingers. "Please, Mistress, don't stop. I want to cum so bad."

"Begging already? I thought it would take longer to break you."

"No Mistress, I can go all night. Whatever pleases you."

She shoved the plug back in. "Alright, you say this is what you want," she walked over to her drawer of toys, pulling out her harness with a new dildo attached to it. Heels clicking loudly, she brought the harness to me. Sitting up on my knees, I held it open for her, placing each boot through, and slid it up her beautiful legs. I tightened the straps to the side and sat back on my knees, admiring my mistress's cock.

Dangling in front of my face was a white cock. This dildo looked life-like, with veins running down the sides. It appeared less firm than the purple dildo she used on me as it swayed side to side.

I bit my bottom lip, eager to show off my blowjob skills.

"Not so fast, little pet. I bought you something new to wear." She returned from her closet carrying an unopened box." I ordered it the morning after our first session. Didn't really have a chance to give it to you. Go ahead open it."

On my knees, she handed me the box. It was noticeably heavy. Opening the box I found some shiny, black material. Holding it up I realized what it was, my dick leaking more.

"It's amazing, Mistress, thank you. May I wear it?"

"Of course my pet, let me help you."

I handed Jess my new gift, she held it open in front of me, I slid my arms through the sleeve, hands encased in PVC with straps at each hand. Jess went around and zipped up the back, fitting it snugly. Reaching around, she grabbed the straps at the ends of the closed sleeves, with my arms crossed she secured the straps to each other at the back. She had successfully restrained me in a slick, black straight jacket.

"Stand," she commanded.

She reached between my legs, securing straps around each thigh, running front to back, so the jacket wouldn't side up. She turned me toward the mirror, kicking my legs apart.

In the mirror I saw myself standing with my legs shoulders width apart, arms pulled tightly around my chest in a PVC straight jacket. My legs were covered in white thigh-high socks and my member locked tight in its cage, a thin stream of pre-cum dripping off.

"Can you guess what Im gonna do next?"

"Are you going to fuck my ass, Mistress?"

She stood before me, just a few inches shorter than me in her spiked-heeled boots. Wrapping her arms around my neck she pulled me in for a kiss. Kissing me with such passion and lust, her tongue dancing with mine. Of all the fun we had tonight, this was a nice change of pace. This intimacy is what I missed.

She pressed her hips into mine, rubbing her cock against mine. My dick was the same length as hers, but with a little less girth. Of course, hers dwarfed mine as mine was tightly sealed away.

She pulled my hair as my tongue invaded her mouth. She began to suck on it like she was giving head.

"Does that give you a hint?"

"Im gonna suck your cock, Ma'am," I said, equal parts answer and question.

"Good boy, you were always so smart."

After leaving for the bathroom, she returned with eyeliner, applying it under my eyelids.

"May I ask why you're applying eyeliner, Mistress? Not that I object."

I looked up as she drew dark lines under my eyes.

"Well, pet," she said a matter of factly, "I always wanted to see tears run down someone's face as I fucked their mouth. So I figured eyeliner would look real sexy running down your sissy face."

"Have you ever, uh, had a man suck your strapon."

Jess paused her work, feeling my insecurity.

Those beautiful blue eyes stared into mine, revealing intimacy and reassurance.

"No. No one has ever sucked my strapon before, and I'm really glad you'll be my first."

I couldn't hide my smile, knowing I would be fulfilling one of her fantasies for the first time. I was filled with pride and determination, ready to impress her.

"While we're on that topic. Have you been playing with anyone else? During your 'research'?"

She was asking if I had been seeing anyone else. How cute. "No, Ma'am. Just watched some videos. No one near as amazing as you though."

Once satisfied, she tossed her makeup to the side. Placing her hand on the top of my head, she guided me down to my knees. I loved how controlling she was.

On my search for femdom enlightenment, I stumbled upon several strap-on blowjob videos. One of the videos I found was called Brodie's Sub Does His Best to Deepthroat, where the man is bound on his knees and easily takes her strapon cock deep in his mouth. The old me would never watch something like that, but the new, submissive me found it very sexy. There was something about the woman giving a man a taste of his own medicine.

My strategy going in was simple, try to make as much saliva as possible, and reenact every blowjob scene I've ever seen. Also, I had practiced on some cucumbers.

On my knees, I eyed her cock as she ran her fingers through my hair, sending tingles down my spine.

"Kiss mommy's cock."

Hearing her refer to herself as 'mommy' made me writhe in my bonds. I needed to relieve myself, to unlock this damn cage. But it wasn't for me to unlock. I leaned in, placing kisses on the head of her white cock.

"Kiss mommy's dick like you mean it," she said while combing her fingers through my hair.

My kisses became more vigorous, lips moving along the shaft. Her breathing became deep as she fought to calm herself. I loved how her nails dragged against my scalp.

"Beg for mommy's cock."

She wanted to tease me, to break me. Not without me teasing her too. I knew she wanted this blowjob, might as well have my fun too.

Silently I continued to kiss and tease her cock with tiny pecks.

She raised her eyebrow at me to say, 'are you sure you want to play it like this?'

I failed to hold back a smirk as my pecking continued.

She leaned down, bringing her face to mine, like scolding a child. She stared me down, giving me the mom look. I stood, or kneeled, my ground, staring defiantly back at her.

She grabbed me by the jaw and turned my head. Whispering in my ear, she said, "If you ever want out of that cock cage, you will beg for MOMMY's cock. You better beg good and suck this cock as if your life fucking depends on it."

She released my face and stood up tall. Raising those sexy, dark eyebrows. I had no doubt that she would leave me caged up.

I gave in, already having my fun. Plus that scolding made my dick strain harder.

"Mistress, please let me suck your amazing cock. Please train my throat and use it. I want to gag on mommy's big, fat cock so bad. I want to be facefucked until I'm gasping for air and tears are running down my face. Please teach your pet to deepthroat mommy's cock."

"Damn pet, that was so fucking sexy. You got mommy so horny. Now open up that sissy mouth."

"Wait, could we, maybe, record this? Like on your phone."

She took a moment to contemplate, blushing at the idea. I loved how she was still that sweet Jessica underneath her dom outfit.

"Fine," she replied. Then spun on her heels in a cute twirl to fetch her phone. She strolled back into the room, will an extra kick in her step. Placing the phone on the dresser she turned back to me, resuming her dominant role. Step by slow step, she made her way back to me, strutting for the camera.

She held either side of my head and guided her strapon to my mouth. Now wanting to please Jess and the camera, I opened my mouth wide, ready to impress her. Keeping my eyes locked on hers she slowly pulled my head toward the tip. I could see her savoring this moment, wanting to remember it. The intimacy was intense as we instantly forgot that the phone was recording.

She drew me in and I took her cock into my mouth. Messaging her silicone head with my lips and tongue as she rocked my head back and forth. Getting into the groove, she started pumping her hips forward, inching more of her strapon into my mouth.

My head bobbed as I watch her tuck her hair behind her ear while biting her bottom lip. Then a switch flipped and she was back to business as she thrust forward.

The sudden assault to the back of my throat led to a loud gag. Good thing I had been storing up spit because she was pounding my mouth. I had teased Jess back and now I was paying the price. This was the response I was waiting for. I didn't want her to hold back. I needed to show her that not only could I take what she threw at me, but that I wanted it. No one would ever call me boring after this.

Jess held the back of my head, forcing my head to bob on her dick. I struggled to keep my eyes open as the dildo tickled my tonsils. The more she thrust, the more accepting my throat became. Then she released me to catch my breath.

"Come on slut, it's not gonna suck itself," she said, placing her hands on her hips, looking like a goth supergirl while I finished my coughing fit.

Unable to use my hands, I used my tongue to bring her head into my mouth. Sucking her cock into my mouth. I stared up at Jess, making eye contact just like the best pornstars do.

I bobbed my head in a steady rhythm, back and forth, back and forth. coating the life-like dildo in my spit, reminding myself not to swallow and waste it. I was able to take in 4 inches relatively easily, I was halfway there. As I took her deeper, I started hitting my gag reflex.

After a few minutes of pushing myself, I was able to get 6 of the 7 inches into my mouth. Holding my breath as long as I could. Tears began to run down my face, smearing the eyeliner, and leaving two dark trails along my cheeks.

Moans escaped Jess as she began to grind her hips against the base of the dildo, inching closer to climax. I struggled to keep eye contact as her cock worked my gag reflex. Tears ran down my face mixing with the copious amount of saliva that flowed from my mouth. Her tempo increased as her climax flooded her.

Wet sounds escaped my mouth. Her dick like a plunger to my throat.

Forcing the entire strapon into my throat, my lips came flush with her pelvis. She gyrated her pelvis against my face. Veins bulged from my forehead as my face turned red, and tears blurred my vision.

Trembling and moaning, Jessica held my head tight against her crotch, as she finished cumming. Releasing my head, I gasped for air.

She retrieved a towel to wipe her thighs, then my face, leaving the smeared eyeliner.

"Ready for the grand final?" she asked while recovering from her climax.

"Im ready to take that cock, Mistress."

"Oh, you are so cute my little pet. I won't be using this tiny cock, I got something bigger waiting for you."

Tiny? No one would call her current dildo 'tiny'. I wanted a challenge and she was giving me one. From the closet, she dragged out a wooded sex bench, with leather bands and various straps.

"Up boy," she said, patting the middle of the bench.

I rose to my feet, still bound in my straight jacket. Making my way to the bench I placed either knee on the lower platforms while Jess helped me as I lowered my chest onto the top, center pad. She cinched down several straps, securing my calves, and upper and lower back to the sex bench.

She gave my ass a hard smack with her hand, watching my body jerk, showing how secure I was. Standing in front of me she removed her white dildo, exchanging it for a new cock. This cock was black, with even more veins. It had to be at least 12 inches long.

Seductively, she applied lube to her massive cock, as she jerked it off in front of me. She walked around to my rear, where she rubbed her hands against my ass cheeks and over my sock-covered legs. Placing the massive black cock between my cheeks she slid it back and forth.

"Beg!"

As intimidated as I was to take her new cock, I was equally excited. "Please, Mommy, fuck me with your fat cock and make me your little slut. Do as you wish with my sissy ass."

Jess tugged on my butt plug, removing it slowly, releasing it just before the thickest portion was out, watching my ass suck it back in. She did this several times to stretch out my ass to prepare it before removing it. Jess brought the head of her black cock to my ass and began to apply pressure. I studied my breathing and force my ass to relax. Reenacting the videos I watched, I puckered my rosebud out, allowing her t easier access.

The head of the black dildo progressed further, stretching my sphincter. Slowly my ass hole stretched around the object, swallowing the head. Jess paused her progression, caressing my ass cheeks as she let me acclimate to her size. And after studying my breath she began to push the head in and out, to help my rosebud stay open. Removing the head from my ass she reached out underneath the bench and pulled out a turkey baster. Inserting it into my ass, she filled it with Lube. The cold fluid sent chills through my body.

Once again she walked in front of me, this time applying a gag hardest over my head. I willingly accept the ball gag into my mouth, biting down as she secured the harness to the back of my head. Returning to my ass, she tore open a condom and stretched it over my caged cock.

Alright, my little pet. You're all ready to go. I'm going to fuck you so hard and I'm not gonna stop until you come. Do you understand?"

I nodded my head vigorously as I let out a muffled reply. Once again she pressed the tip of her cock to my ass, this time entering smoother from the stretching.

Once my ass close around the head, she was ready to fuck. Without any more stretching, she began to fill my ass, starting with just a few inches at a time.

Jess had placed the bench in front of her changing mirror, allowing me the privilege to watch myself get fucked. She started off with slow, rhythmic rocking. The pain had subsided, leading to a buildup of intense pleasure. The last time was the first time that I tried anal. I was reluctant, not wanting to enjoy the experience. But this time, I was willing and ready.

Her rhythm increased as I watched her in the mirror, moving her hips like she was belly dancing. Her moans started off low and quiet as her climax was solely built. Grabbing hold of either side of my hips she called me back and rammed her cock forward, driving more of her cock into my hungry ass.

Her cock was stimulating my prostate as her thrusting became faster and harder. My moans were muffled by the gag ball. Jess grabbed the back of my gag harness, wrenching my head back, and forcing me to face myself in the mirror. Drool ran down my chin as my eyes started to roll to the back of my head.

"You better not come without permission you little slut" she said through panted breaths.

I was about to explode. I struggled to hold my climax back, knowing I couldn't last much longer.

"Please mommy, please can I cum. Please let your little ass slut cum," I tried to say through the gag, but it came out all muffled.

Jess placed her feet on either side of my ankles. Pausing her assault she climbed onto the bench, getting into a squatting position. She placed her hands around my neck, craning my head up and giving her support.

We made eye contact in the mirror, and she said, "You have 10 seconds to cum, and you better keep eye contact as a pound your ass."

Before I could reply, she began the most brutal assault on my ass. As instructed, I kept my eyes locked on hers as she fucked me in a squatty position, hands tightly around my neck. I couldn't help but notice how she rode me like a horse jockey. The room quickly filled, with the sounds of my loud moans mixed with the rhythmic clapping of her thighs against my ass. With her strap on now fully bottoming out, cum erupted from my cage, collecting in the condom she put around my secured member. I began to see spots as my balls were emptied. All the stored semen shot out of my restrained cock. Jess continued her pounding my ass as I screamed in pleasure. My moans slowly died out as my orgasm subsided, balls drained of all cum. Jessicas thrusts slow down as she made sure to milk all the cum out of me.

I couldn't help but notice the triumphant smirk Jessica wore as she climbed off the bench, and pull the strap-on out of me with an audible plop. I watched in a daze as she admired her work, spreading my cheeks apart, and gazing at my gaping ass.

She left me restrained as she went to the bathroom. Still tied to the bench, I work to slow down my breathing, feeling completely drained and high off pure pleasure. Even though my ass was sore, and my balls were drained, I could still feel my cock yearning for release.

Jessica returned, still dress stop with her strap-on and boots removed. Using a towel she wiped down the back of my legs. Removing the condom, she held it up for me to see. It looked like a small water balloon filled with a cloudy white liquid. She twisted the top and tossed it onto the bed. I had a feeling she would make me eat it later. She found the key to my chastity cage and released my manhood, unfastened the straps securing me to the bench, then removed the gag harness.

After using the towel to wipe up the drool from my face, she asked, "So, did my little sub have fun?"

"Oh yes, mistress. That was the best night of my life."

Clipping the leash onto my collar, she said, " Oh, but the night is not over yet. You get one last reward."

She pulled me by the leash as I climbed off the bench, stretching out my legs. She pulled me in for a deep kiss. Grabbing my cock, it instantly shot back to life. Still kissing she pulled me by my cock, leading me to the edge of the bed.

Releasing my cock, she climbed back onto the bed. She spread her legs and unzipped the crotch of her latex teddy, revealing her dripping wet pussy.

After rubbing herself for several seconds, she said, "Well, I released you for a reason."

Still restrained by the leather straight jacket, I climbed onto the bed. I couldn't believe she was going to let me fuck her. I just hope that she didn't have any more surprises in store for me. As I walked on my knees toward her, she wrapped her legs around my waist, pulling me in.

Sensing my nervousness, she grabbed my cock, saying, "It's OK, baby. I want you to fuck me."

I was hesitant to fuck Jessica because I knew that her ex had sexually abused her. But sensing my hesitation, she reassured me.