Mistress Jenny's First Dick

"Come on! It's getting late, and my place is nearby. You don't need to head back to the hotel."

Her green eyes narrowed, but Jenny let out a sigh. Her red hair settling about her shoulders 'Alright.. That does make more sense than running halfway across town."

She had been visiting from out of town, and finally met up with her friend from online. Her slave girl wasn't keen on flying and so the lesbian Mistress had left her back home in Switzerland. The evening was going well, but it was a long trip and the jet lag was catching up...

--

Turning on the lights as we stepped inside, the apartment was simple but well furnished. Having just moved in a couple weeks earlier it wasn't surprising. But given how late we'd been out, there was only one thing Jenny had in mind..

Her eyes were closed the instant her head hit the pillow. The feeling of down and soft blankets brought her into a dreamless sleep.

Her body still thick with the heaviness of sleep when she felt it, a familiar sensation of fibre across her wrists, and calves.. She opened her eyes and there was only blackness with a bit of light peeking through under the blindfold.

With a gasp she yelled "What the h-" when she felt the ropes tighten. Her wrists and ankles pulled tight down to the bed. She heard a click and the sound of rustling rope. No doubt something being tied off.

"Hell!" She finished. That was when she felt the sensation of metal against her leg. Freezing, for worry of an unexpected movement leading to something else.. She heard the familiar sound of shears cutting fabric.. Cutting away her clothes in a smooth line up one leg to her left hip. "Fuc-" Jenny started to scream, when something was shoved into her mouth. She felt rough hands securing what felt and smelt like leather behind her head - catching some stray hairs in the buckle. Her mouth was stuffed. Using her tongue to explore it, it wasn't quite a ball gag - but a penis gag.

"Mffmfmf!" It came out. Then the feeling of cool air and skin resumed. She felt the cool lines of metal snipping away what she was wearing, save for her panties. Having gone to sleep while wearing a comfortable top nothing was shielding her breasts from the open air..

His voice came, a soft baritone "Now now.. We both know you wanted this. After all with all our talks and your fantasies.."

A rough calloused hand ran up from her leg, fingertips trailing up to her breast.. Getting a good handful of it, squeezing hard enough to leave bruises "Mm.. I'm going to enjoy this. And we both know you will too.."

After struggling to fight the ropes she sighed and sank into the bed. The ropes were about her wrists, her shoulders, her waist, her thighs, and her calves.. The more she fought the tighter they became..

----

Grinning down at her.. Bound to the bed and gagged, his hands roaming over her body. He couldn't help but enjoy this sight.. Particularly the muffled scream as he closed the clamp over her nipples, with the chain trailing between them. She did so love to see tits clamped after all.. The black rope was a good offset to her pale skin. Though those panties would have to go..

Rather than cut them away he took the thin fabric in both hands..

--

It was a hard pinch on her nipples and Jenny let out of a muffled cry. Not as bad as what she's inflicted to be sure, but he must have adjusted the springs on these as they were pressing down hard.. The feeling of metal trailing between the valley of her breasts let her know that he would no doubt be tugging on these later.

Then a pair of rough hands gripped the last fabric, and with a smooth motion tore the panties at one side, then the other. Feeling cool air against her skin and her sex..

Still only getting glimpses of light beneath the blindfold. She tried to cry out. A half moment later there was a sound 'pffffft' and suddenly the cock gag in her mouth grew. "Oh shit" She thought. Then a few more pumps.

Cheeks starting to puff out, it wasn't the width that was the problem... The head of this cock started to brush the back of her throat..

----

Satisfied she wouldn't do much more mumbling.. He set to work pulling out his toys and accessories..

The sight of the bound redhead was something to enjoy..

Click Came the sound of a camera. "A nice momento" He spoke as Jenny squirmed upon hearing the familiar sound.

Looking over the toys and accessories laid out, one caught his eye..

----

Trying not to struggle was hard when Jenny heard the sound of a photo being taken. The ropes tightened slightly over her thighs and wrists. The cock-gag was tickling the back of her throat, threatening to trigger her gag reflex..

Then she felt it. Something small and cold press against her clit. It was rounded and smooth.. An egg vibrator she realized.. Then she felt something different. Another cold object, touching her inner thighs and just about her waist.. A strong hand under he back lifted her ass off the bed and the same feeling slid up "Oh no..".

----

With a smooth motion he closed the chastity belt in place, holding the vibrator against Jenny. A solid "Thunk" sounded as he closed the locks holding the belt in place. Letting one hand roam, fingertips trailing.. One at the edge of the belt, just enough so Jenny would know where it stopped.. And the other against her skin.

His fingers came to rest down between those cheeks.. It was open here.

Then he touched his phone.

----

Buzzzz

The egg started vibrating. He put it perfectly, just enough to touch Jenny's clit with one end. It was set to a low vibration, then would switch to a pulse.

Despite her predicament.. She had to admit this was a good setup. No matter how she felt about this, it was hitting her buttons and getting her wet..

There was nothing for a good few minutes. That was when she became aware that the intensity of the vibrator had increased and she had started letting out little whimpers..

She felt warm skin touch hers, a hand brushing her left breast. Then the clamp on her nipple tightened "Oh! He must have put a screw clamp on.." and it kept tightening, slowly.. Feeling her nipple becoming a little flatter she let out a squeak..

Pffftt

The cock-gag grew larger, the head now slipping more fully into her throat.. She had to control her breathing to keep from gagging.. Jenny could feel her her lips stretched wide around this gag now and knew this would be a good visual.

Then came the pressure on the other nipple, the same number of slow turns of the screw.. One.. Two..

After four turns she felt like her nipples must be the size of a nickel..

He gave a quick tug on the chain, making another moan from Jenny. A mix of pain and pleasure with the constant pulsing of the vibrator..

----

Watching this redhead squirm, bound and clamped was a delight. But she had another hole that needed filling..

----

Wet fingers touched Jenny's only open hole. She could feel something thick and gooey spread around it.. "At least I get a little lube.."

Then she felt it, something cold and smooth press between her cheeks. Slipping in slowly.. Oh so slowly, he was dragging this out.. Her hole gradually opened up for what must be a plug.. The vibrator sped up another notch.. Click. Another sound of a photo being taken..

She kept feeling her ass stretch, a few centimetres..Then another couple.. "Surely it must be getting to the end of the taper soon?! " She thought as the pain of her as being stretched started to match the pleasure at her clit..

----

But it didn't.

The plug wouldn't finish stretching her ass until the widest part, all 7cm of it was inside.. The Her ass closed around the end of the plug and held it tight..

Buzzzzzzzzzzzz!

----

The vibrator went higher as he finished shoving the plug into her. "Gods! This is a wide plug! I wish he gave me more lube" Jenny thought.

Unnhhhhggrrrr She started to moan around the cock-gag, struggling to breathe around it as it hit her tonsils..

A sharp tug on the chain holding her clamped nipples brought her attention back.

This was when she realized that she was moving.

----

Unlocking a couple of clasps from the bed frame, he took hold of the mattress and swiveled it.

A while ago, it seemed a good idea to be able to change position at whim - so a lazy susan was installed under the bed for just such an occasion..

After turning her around, so her head was facing him he grinned down at her and started to unbuckle his pants..

----

Ziiiiiiiiiiiiiip!

Came the sound of a zipper once she stopped moving. Not quite sure what happened, Jenny was quite sure of what was coming next - even before the strong hand gripped her gagged face, a finger tracing her stretched lips. He whispered "Now.. I'm going to let the gag off, and you're going to do what I want."

The Bzzzzz of the toy slowed down.. Jenny's started to feel her aching and stuffed ass more than her soaking pussy now..

"Understood" his voice came, and it had the note of a question..

The redhead still couldn't see beneath the blindfold, but she could see light peeking under and she tried to reply around the gag "Mphfff!"

"Ah yes.." With a swooshing sound, the gag deflated suddenly.. Then the buckle at the back of her head was undone. The cock-gag made a wet popping sound as it was pulled from her lips, saliva trailing from them to the gag along with that stray hair..

Cough! Cough! She gasped for a couple of breaths. "This was just a fantasy! You know th--" She started to shout, her voice rough - Was cut off, as her mouth was stuffed with something else. Strong hand forcing her mouth open, she could feel pieces of rubber shoved in, tugging a the corners of her mouth. Her eyes beneath the gag widened in recognition - 'A Dental Gag!?!' She thought.. Then a sinking feeling in her stomach.. "That means.."

-- --

He didn't let her finish the thought. Once the dental gag was on and strapped in, he started ratcheting the bound redhead's mouth open wider. Rrrk. Rrrrk. Rrrk.

-- --

"Wide enough" He said.

Jenny felt his cock slip inside her forced-open mouth. Felt the hard smooth skin of him slide past her stretched lips and glide along her tongue. She could taste his pre-cum.

"This won't ge gentle... " The thought came to her, as the tip of his cock touched the back of her throat..

A hand gripped her, thumb resting on her chin and fingers lightly holding her throat.

Then slowly, centimetre, by slow centimetre his cock pressed forward. Pushing into her throat.. Jenny started to gag.

That was when the vibrator's pulsing pattern changed, and sped up..

-- --

Watching the thick cock slide past Jenny's lips, he felt himself grow even firmer and let out a moan that was half growl.. "Mmm.. I've wanted to do this to you for years.." And with that last syllable, he felt his cock hit the bound redhead's throat.. And he pushed forward.. Feeling her throat stretch as she gagged Glrrrk!

Taking hold of the chain connecting her tortured tits, he pulled it tight - tugging her nipples toward him - using it as a handle as he shoved his cock further in..

-- --

Glurrrrk!!!

Jenny was sputtering, saliva trying to cough out around his thickness. Her throat widening as he shoved centimetre, by slow centimetre in. It would have been easier had he just shoved it forcefully.. He wanted her to Feel every moment of this..

That was when her nipples felt like they were on fire and they were stretched. She could feel her breasts being lifted toward her face as the chain was pulled completely tight. 'Aaagnhurgkla!' She tried to scream around the cock in her throat. The vibrations in her cunt were making her soaked.. And the cock down her throat was almost making her forget about her plugged ass stretched wide..

The fingertips on her throat, she realized were for his enjoyment.. She could feel when his cock would go far enough down that it would bulge her throat.. Knowing he always liked that view..

-- --

He started a rhythm, slowly - ever so slowly drawing his cock out of the bound redhead's throat.. Just enough that the tip tickled the back of her throat.. She would gasp a breath in.

And that's when he would thrust it in deep. His hand squeezing around her throat, just tight enough she could feel the strength in it - and she knew he could feel his cock making her throat bulge as much as see it..

A sharp tug on the chain brough Jenny's attention back to her nipples. Her breasts were hoisted skywards as he throat-fucked her, heavy balls slapping against her blindolded face.

It was hard to focus on anything, between the now mild buzzing against her clit, the huge plug in her ass.. The thick cock being rammed down her throat and now Now! It felt like her nipples were being pulled off! Shouldn't the clamps have popped off by n-- Then she remembered. These ones were ones he had either crafted, or modified. They were so tight that they weren't going anywhere unless he wanted it..

Only hoping this would be over soon.. But that hope faded as quick as it came, remembering how long he said he can last..

And on it went.

Glrrrk!

Mphfhfh!

Ghulrk!

Glrack!

With the wetness of her own throat and his pre-cum the only lube for his ruthless pounding.

She could taste the precum coating her throat and could feel her saliva trailing from his cock whenever he pulled out - giving her a chance to gulp for air only for it to be rammed down again. If she didn't time it right, when she took a breath in some of that pre-cum and saliva wound up in her lungs.. This went on..

All the while he was using that chain on her nipples as a handle he would pull on as he fucked her face.

----

After several minutes of using her mouth as his own fleshlight, he pulled his cock out of her throat in one sweep.

Slick with pre-cum and saliva, he saw how much of a mess she was. Letting the thickness of him rest on her face as she panted and gasped for air..

He relaxed the grip on the chain, letting it fall onto her skin.

As much as he enjoyed using her mouth.. He had something else in mind and reached over.

--

Jenny suddenly had air again, and braced for the next thrust.. But instead she felt his heavy cock rest on her face. She could only imagine how it looked..

When suddenly she was aware of two things. Another 'Click' as she heard a phone camera used.

And that she was moving again. She whirled to her left quickly, and suddenly stopped.. He used the lazy suzan bed again.

Gasping for air, she kept expecting something to stuff her mouth again..

Then she heard it. The sound of something crinkling. Like a wrapper tearing.

What is he? Then her eyes widened behind the blindfold. Oh no.. He wouldn-

Then she felt the plug at her ass being drawn out. Slow centimetre by centimetre.

----------

"Now... I could gag you again.. But then I wouldn't hear your moans properly.. "

With a smooth motion, the extra large condom slipped onto him. It would work, even if it was a little tight for comfort.

Using his other hand he pulled out the plug from the bound Jenny's ass.. And then pressed his cock against the hole..

"I'd say.. You're just about stretched out enough for me"

And he shoved it in.

----

Her ass was only 'technically' virgin. In fact Jenny was no stranger to anal penetration. She had first tried it in her mid-teens and practiced it for the last twenty years. First by her own, later with her girlfriends.

And she loved anal. Her ass was used to dildos, plugs, strap-ons and even the small fist of her girlfriend. The big plug, he had violated her ass with before, kind of prepared her for what was about to come.

Years of anal play had trained her sphincter to relax and open up when pushed against.

Those years, the giant plug and the special low resistance condom made sure that there was no resistance, when Jenny lost her anal virginity.

Tied down to a rotating bed, in a foreign city, by a virtual stranger she met years ago on the internet.

Blindfolded, mouth forced wide open by a dental gag, face all drooled up, nipples locked and stretched by vicious clamps, a vibro egg in her pussy and a chastity belt to hold it in place.

Humiliating.

Jenny gasped in surprise when the head entered her back door and held her breath until his balls slapped against her butt cheeks. She moaned in distressed pleasure, when he pulled back again.

She felt betrayed by her own ass. 'GIRL! You are NOT going to enjoy this! You had no choice, when he fucked your face. When he rammed that giant THING down your throat.' She HAD seen it in pictures, it was about arms length and had quite some girth. She was confused to feel some kind of pride that she managed to take it down her throat without puking. His balls had rested on her face!

'You almost suffocated. Without that stupid steel gag, he would be in the emergency room by now. So, stop him from fucking your ass! That's girls only!'

Jenny tightened her ass. He wouldn't have an easy fuck.