First Time as a Bondage Slut

Angie treats Bob to a bondage session with a fucking machine. And she taunts him with thoughts of shemale sex while he's being fucked.

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Angie and I hugged while the strength returned to her legs. I used the time to ask her about her bondage experience and what she knew about bondage, safe words, and Top and Bottom.

She answered my questions openly, but we decided she didn't have enough experience for us to need safe words. She wasn't likely to push me anywhere near my limits.

Once her legs returned, I released her, and she went to the bathroom. I used her absence to move the gyno chair and fucking machine to the side of the Game room. We'd need to clean it before we put it away. Then grabbed a mop and cleaned the fluids from the concrete floor.

When Angie returned, we moved into the Furnace room, aka the toy store. I was enjoying myself, showing her all my fabulous equipment and paraphernalia. I'd pick up pieces and explain them to her: what I liked or disliked about them; what they were for; how to use them; etc. Over the years, I had picked up some items that I regretted purchasing - but I never threw them away - so some of the stuff in the room never got used.

I told her about my preferred positions - for self-bondage - and why I liked them. About toys I used and how they felt and caused me to orgasm. About my appetite for lingerie and latex and why they enhanced my enjoyment of my sessions. About pain and whether I enjoyed it and to what levels. And we even delved into some of my fantasy scenarios.

Angie was still parading around naked. She indicated that she liked being naked in front of me. She enjoyed the way I continued to look at her lustfully and the fact that she was making my cock hard.

All the equipment was now arranged and ready for my pending session. It was time to get started. I looked at Angie nervously - I'd never been a bondage slut in front of someone before. I was becoming anxious and wasn't sure I could do this. She seemed to understand.

She moved in and hugged me, just holding me for a minute. No talking, just her magnificent naked body press to my fully clothed body. Her strawberry-scented hair teased my nostrils. I inhaled and started to relax.

She released me. "Drop your gear, bitch. Time to get you dressed as my slut."

I looked at her with surprise.

"Hey, I watch porn, too. I know the dialog - now get naked, slut!"

I smiled. "Yes, ma'am."

"Mistress!" she barked.

"Yes, Mistress!"

I quickly pulled off my clothes and deposited them on the sofa. My back was turned, and the leather tip of a riding crop slapped my ass cheek, but as discussed, it was restrained and nowhere near my pain threshold.

"Fold your clothes nicely, bitch." Angie was apparently really getting into the part of Dominatrix.

"Yes, Mistress!" I quickly folded the clothes and deposited them on the sofa in a neat and orderly pile.

I turned and faced Angie, my hands in front of my cock. It had been a long time since I was naked before a beautiful woman with the lights on, and I was embarrassed. Angie didn't say anything; she used the tip of the riding crop to tap my hands and force me to drop them to my sides, exposing my raging hard-on.

"Very nice, pet," she mused. "Very nice indeed."

I smiled, but my entire body flushed a brilliant red from blushing. Angie stretched out her arm, palm up, and presented a pair of stockings she had apparently brought from the toy room. I took them and allowed them to expand - they were opaque white, with a row of large back polka-dots running down the back like a seam. They also had black Cuban heels and black tops with built-in elastic.

"Since we're gonna be fucking your ass like a slut, I want you to look the part. And since your legs aren't shaved, these should cover that unsightly hair." Angie explained. "Now put them on, and let's get you positioned."

I donned the stockings, giving her a show. Slowly sliding them up my legs. Spending time ensuring the dots ran down the back of my leg in a straight line. Then I caressed my leg, stretching it out in front of me like you see women do in the movies.

Angie laughed, a delighted little laugh, and smiled in appreciation.

I stood and moved to the bondage frame. It was a modified steel T-bar, to which I added a padded top and MagBound bases bolted to the ends. The padding made it comfortable, and the time-release restraints allowed for self-bondage. But today, we'd use the original built-in cuffs to restrain me.

I laid my chest and arms on the T-bar, and Angie fastened my wrists into the cuffs. I hadn't even thought about it. I was now restrained and at her mercy. A flash of panic flashed through my brain and must have registered on my face.

"Bob," Angie cooed in my ear, "please don't worry. You gave me one of the greatest gifts I've ever received, and now I hope I can return the favor."

She paused and moved to my other ear. "But that doesn't mean I won't torment and tease you - just like you did - you nasty little perv." Her words were playful and excited.

She chuckled and traced the riding crop along my back, over my ass checks, down the back of my stockings, and then up between my legs. There she stopped and tapped my dangling balls lightly with the leather tip. Tap, tap, tap. My cock bounced and throbbed, and I moaned my delight.

She paused for 15-20 seconds, then tapped again. Another pause. It was delightful torment. Crack! The tip of the riding crop whipped across both ass cheeks. I howled, more from surprise than from pain.

"You're supposed to thank me!" Angie snarled. "You've watched enough bondage to know that."

Shit! "Thank you, Mistress! I'm sorry for my lack of manners! I won't forget again." I cried quickly.

I considered providing the excuse that I'd never had a bondage session with another person but dismissed the idea. Mistresses aren't looking for justification - just compliance and subservience.

Angie made no further comment, and I heard her bare feet pad away from the T-bar.

She returned carrying something that rattled. I already had leather cuffs around my ankles, and I felt her clip the spreader bar to the cuff of my left ankle. She rested the spreader bar on my right foot, then used the riding crop to coax me to spread my legs. I moved my legs apart until the bar slid off my right foot. Angie fastened the bar to my right ankle.

My feet were about 3 feet apart, and my ass was slightly lower than my chest. My ass cheeks were spread wide apart, and I could feel the warm air caressing my exposed pucker hole. Heaven.

"Thank you, Mistress. This new position feels wonderful." I gushed, hoping to prevent another strike.

Angie didn't reply and remained behind me. I heard her struggling with the fucking machine. This time we'd pulled out the big gun. The ShockSpot. This bad boy had a 12-inch stroke and could seriously damage me if not used carefully.

I'd connected the laptop to the fucking machine, fired up the software, and shown Angie how to run it using the pre-programmed routines. I purposely left the remote control disconnected, so there couldn't be any accidents.

The Shockspot was great, except for its tendency to buck - it wasn't heavy enough. So I put a 50-pound fitness sandbag on its base to keep it from moving. Perhaps she was struggling to move it? Or maybe she couldn't release the arm tensioners? While I pondered her struggle, I felt the tip of the dildo touch my taint and move up to my asshole. Problem solved, I guess...

I'd chosen a small dildo for this session. 8 inches long but only about 1 and 1/2 inches in diameter - with big floppy balls dangling from its base. The filenames of the fucking machine routines indicated stroke length, so Angie wouldn't have any problem choosing a program compatible with the dildo.

"Shit!" She moved the dildo away from my ass.

The next feeling was lube being poured into my ass crack. Angie allowed it to run down my ass crack to my fuck hole, gathered it with her fingers, and pressed it into my waiting hole. Then she inserted a lube shooter and filled my bowels with my preferred long-session lube.

The tip of the dildo touched my ass again. Angie moved it around for a minute, setting the height and angle. The head of the dildo pressed into my goo-filled pucker hole, and she locked it in position. I was getting excited. My cock was at full-mast and throbbing between my legs.

I expected the TV to start and for her to play some videos. Instead, she walked to a place about two feet from my head and set a chair on the floor. Angie sat, spread her legs, and used her fingers to splay her pussy lips. Then sat there and watched my reaction.

I gulped and stared. God, she looked amazing. I wanted to bury my face in her pussy and worship her. To throw her over the arm of the sofa and ram my aching cock deep in her cunt, then fuck her till I exploded. But I was bound and helpless, and she was teasing me. Gently stroking her over-used pussy and caressing her breasts.

"You like what you see, slave." Angie cooed.

"Yes, Mistress! You're beautiful!"

"Just beautiful?" She teased. "Don't you like my pussy, my titties, my cute little piercings? Don't you want something?"

"Mistress! You're stunning. I want to drop to my knees and worship your magnificent pussy. To lick and tease your legs and lips - drinking in your juices and fragrance. To caress your sensitive titties and tweak your nipples with those dainty gold rings. Please, Mistress, free me, and let me show you!"

"Mmmmm. That sounds inviting, but my pussy is far too sensitive right now, so I'll have to say no. For now..."

She stood and walked toward me. Her belly touched my forehead, and my eyes stared down toward her pussy. Her little blonde landing strip pointed to her puffy pink well-used lips. They almost seemed to glow against the alabaster skin inside her tan lines.

"Can you smell me, Bob?" She asked huskily. "Can you smell my pussy? As hard as that machine fucked me earlier, I'm getting wet again. I'm getting wet at the thought of fucking you this time. Are you as excited as I am, slut? Are you ready? Ready to get fucked? Are you?"

I inhaled deeply, her scent burning my nostrils. "Yes, Mistress! Your fragrance is superb. I can't wait for you to start fucking me!" I clamored.

She stood there unmoving for a few seconds, allowing me to bask in her essence, then moved away. I heard her tap the laptop touchpad, and the dildo started moving.

All the routines I've created were designed to be used in self-bondage. So they all start with a slow inward thrust to full depth, followed by a 3-second pause at full extension. This allows me to decide if the dildo needs depth adjustment. In this case, the dildo halted longer than 3 seconds; Angie must have paused the program.

I felt her release the arm of the fucking machine, and the dildo adjusted deeper, and the angle changed.

"How's that, slut?" Angie queried. "Deeper? Angle change? More lube? This is your only chance."

"It's perfect. Thank you, Mistress!" I gushed. "Are you happy, Mistress?"

"Such a compliant slave. How darling." She mocked. "Okay, let's fuck this pig." And she slapped my ass.

The dildo started moving again, the routine continuing. I didn't know which program she'd chosen, but they all started alike.

The dildo retracted to its full outward position and again paused to allow me to gauge if everything was good. Angie had selected well. The stroke was about 5 inches. This meant 2 inches would remain inserted on retraction, and 7 inches would be buried in my hole at full extension.

The fake cock moved again, 3 complete strokes, slow in, rapid out. This was to test that it didn't pull out on fast retraction. Next was a single swift in-and-out thrust. This ensured that the quick inward trust didn't cause pain or discomfort. When you're locked in self-bondage, prolonged discomfort is a bad thing.

The prelude was finished; the fucking started. The dildo began a slow full insertion, at which point it paused, then 3 quick short thrusts occurred. This little trick made it seem like a person was wiggling a cock in your ass, and I loved it. The dildo retracted. And the motion repeated.

"You little prick!" Angie cried. "Why didn't you let me play with this incredible machine!"

The shaft of the riding crop cracked across both of my ass cheeks - more forcefully than I would have liked.

"Mistress! This machine can be overwhelming for first-time use." I panted, already feeling giddy from the dildo massaging my ass. "The machine we used on you nearly made you stop early. I didn't want to overdo it and hook you up to this monster for your first session."

"So you assumed I couldn't take it." The crop stung my ass again, with far less energy. "And you assumed there would be more than one session." Another swack. "That's pretty bold, slut." A third but pleasant sting from the crop.

Angie's words were condemning, but her tone indicated that she was teasing.

"I'm sorry, Mistress. I should have consulted you. I shouldn't have assumed."

"You were probably right, pet. But don't do it again." The tip of the riding crop slapped lightly against my ass cheeks.

The TV came to life, and after a few seconds, a video started to play. Music blared from the soundbar and filled the room. On-screen, women began fucking bound slaves with strap-ons. It was a wondrous sight.

"Well, slave. That should keep you entertained for a while. I'm going to go and clean the house. I do, after all, still have a job to perform." Angie chuckled to herself.

"You don't need to do that, Mistress." I cried. I didn't want her to leave. I wanted her to stay and play with me.

Angie walked back into my view and squatted in front of me. She looked me in the eye as Angie, not my Mistress.

"Yes... I do, Bob." She spoke quietly and calmly. "I take my job seriously, and I need this job. And I'm not letting you pay me without doing the work. I'd feel like a hooker or escort if you did that. So I'm going to go clean while you get fucked."

She looked at me. Waiting for a challenge or argument.

"I understand, Angie. I'd never want you to feel like that."

"Good. I'm glad we're on the same page." She patted my face. "Now, I'm gonna go clean. You enjoy your fucking."

She stood. "I'll check in on you from time to time, pet. But with the volume of the music, you'll never know when I'm here. Watching your cute little ass railed by that wonderful cock. Perhaps I'll sneak up and touch you. Run a fingernail or the crop along your engorged cock - I'm sure it'll be leaking before long. Maybe I'll watch while you have an anal orgasm. Moaning and gasping as that long hard dick drives into your ass. Does it excite you, slut? Your Mistress watching you pleasured by a big cock? Do NOT answer that! Just think about it." She laughed.

"Ta, ta, slave." And I watched her legs move out of sight.

I looked at the TV and enjoyed the show. The cock in my ass paused - part of the programming - torment and denial. A new clip was playing. Angie must have selected a playlist of some kind. This video had Trans-women fucking bound slaves. I marveled at the size of their cocks. My dick bounced between my legs from desire and lust. I shuddered at the thought of one of them fucking me. I imagined the cock in my ass belonged to one of them. I moaned with desire and shivered.

I wondered if Angie was still watching. If she'd seen my reaction to the Shemales and heard my moan. God, what would she think? Then I laughed to myself quietly. She'd already seen me fucking myself in lingerie; why would my reaction to Shemales surprise her.

The cock started moving again. This time it was long deep strokes. Fast in, agonizingly slow as it retracted. Over and over, the dildo slammed into my ass. The big dangly balls slapped the upper edge of my scrotum. Teasing me. Taunting me. I inhaled deeply, quavered, and gyrated my hips around the cock as it pulled out. Fucking sublime.

The cock stopped again - FUCK! I loved and hated the pauses I built into the routines. They would allow me to fuck myself for hours, but they also drove me fucking insane. And worse, they were almost always at full retraction. Bound to the T-bar, I couldn't move to fuck myself on the stationary cock.

The assault on my ass continued for 20-30 minutes. The fucking machine was cycling through its random programming. It had taken me to the edge of orgasm several times but never allowed release. I was sweating from exertion and crazed from desire.

A new clip started playing. A Mistress approached a slave in a pillory. Other than the dark magenta latex stockings, and black 4-inch stiletto heels, she was fabulously naked. Her gigantic tits and shaved pussy were on full display. Her right hand held a long flogger of leather or suede. She approached him from behind and trailed the tresses up his back.

As I watched, I felt long soft fingers of leather touch the top of my ass and trail up my back. I arched into them and trembled with fear, delight, and anticipation. Angie was back, and it appeared she was mimicking the scene on the TV. Or perhaps she never left. The thought made me giddy.

On-screen, the Mistress walked before her slave and allowed him to admire her body. At the same time, Angie came into view, her toned, taught ass blocking the TV. I gasped. She was now wearing a pair of my lace-up stockings. I didn't own any that matched those of the Mistress on screen, but the ones Angie had donned were opaque black with shimmering crimson satin laces. She'd obviously spent time putting them together because the original laces were just flat black.

She bent at the waist - her stocking-clad feet about 2 feet apart - and peered up at me between her legs. I couldn't help myself; I struggled to free myself - pulling at my bonds. I wanted her. I wanted her, NOW!

Angie grinned from ear to ear, "you like; my little anal slut? I noticed your rolls of colored satin and these delicious lace-up stockings; and knew they'd be spectacular when paired."

"They're fucking remarkable, Mistress. Thank you for sharing them. May I..." My words caught in my throat.

The fucking machine had gone into what I like to call berserker mode. It moved at top speed, over 1000 strokes per minute, using a stroke distance of less than 1/4 inch. It made it feel like it was vibrating and thrusting simultaneously. It was massively intense and always took my breath away.

Angie cocked her head, still peering at me between her legs. My mouth was open, and my eyes were wide. No sound came from my mouth, and I was holding my breath. A big shit-eating grin crossed Angie's face, and she stood. The flogger started swishing through the air as she moved out of my sight.

The flogger started to swish across my back, the tresses teasing and tickling. I shivered and fluttered from their sensual caress, my fingers wiggling above the T-bar, seeking release from their restraints. It was rapturous.

I finally noticed the TV again, and the Mistress was now spinning the flogger in a circle over the slave's back. As I watched the scene, the flogger in Angie's hand began to follow the same pattern. Spinning over my back. The tips of the flogger danced across my skin. From my hips to my shoulders and back. Over and over. My entire back was now warm from their stinging caress.

The Mistress moved to her slave's ass. Oh, god, I thought. Here it comes. As I watched, the stinging caress of the tresses began to flail my ass cheeks. A figure eight pattern. Diagonally down across my left cheek, circling up through the air, then diagonally down and across my right ass cheek, then circling up to repeat the pattern and complete the figure eight.

My ass was pink and burning. The flogger moved closer, and the meat of the tresses started to thump against my ass, just like the Mistress on TV. Angie either played with floggers before or was a quick study - she was masterful. The glorious beating continued for minutes. The fucking machine changed to a fast medium-length stroke pattern while Angie continued her assault on my ass.