Submission in the Algarve

She stood behind me, her hands caressed my arse, the recent whipping made it both sensual and painful, she held the lube bottle high above me and began to squeeze, it dripped out onto my back and her hand slowly worked it down the crack in my cheeks, she swirled it around the entrance to my virgin hole, then popped a finger inside, I gasped.

"Your arse has a good grasp on my finger slut, you're going to be an excellent fuck." Her finger started to move slowly in and out, she poured more lube on it, and soon a second finger joined in, I began to moan under her, soon a third finger was squeezed inside, she wasn't pushing them fully in, only about half way, but it was more than enough.

I heard her laugh behind me, "Such a slutty little slut, aren't you? Your cock is hard for Mistress all the time." She pulled her finger out and in one smooth motion picked up the butt plug, positioned it, and slipped it into my lubed up hole.

"Take your time to get used to the feel, you will keep this inside you, there are straps that can fix it in place, and I might use them later, but part of your punishment is to concentrate on keeping your tight arse squeezed on this plug for the next twelve hours, if it falls out, I will whip the shit out of you, do you understand?"

"Yes, Mistress," I mumbled, the butt plug was a little uncomfortable, it wasn't too long, but it felt wide, and I knew my ring was stretching around it.

"Bring me the white silk robe, after you make me a Martini, join me on the veranda."

I was soon kneeling in a position that would become too familiar over the next two weeks, she had spread her legs and let the robe ride up so I had an eye level view of her pussy, my cock was still hard and she laughed lightly, "Yes, you are allowed to enjoy the sight of your Mistresses body slut."

She had a second then a third Martini, "While you are currently under punishment slut, I am generally happy with your performance, bring me your bowl and one beer."

She poured the beer into the dog bowl, and set it at her feet, I positioned myself on all fours over it, and gently lapped it up, my Mistress was happy with me, I didn't think my cock would ever be soft again.

I was allowed to masturbate into my bed again before sleep, "Doggy position slut." Mistress said as stood over me. Her toe soon started to lightly kick the end of the butt plug, waves of pleasure shot through my body and I soon lost control and spunked into the bed again.

"I don't want your bed getting too stained slut, lick that up." With my mouth tasting of my own spunk, I curled up in the bed and sought sleep at the end of an eventful first day.

Day 2

The next morning I helped my Mistress into a very skimpy bikini and packed a bag with all the things she would need for a day at the beach. Before she left she took a clear plastic chastity device and locked it onto my cock. "It's not that I don't trust you, but sluts will be sluts, after all, this will prevent you from getting a hard on or coming illicitly while I am away."

She pointed to a spot beside the door, "Kneel, there." Once I was properly positioned, she pointed to a webcam she had set up, "You will kneel, hopeful for your Mistresses return, you will not move, you will not fidget, I will be watching from time to time, you will not know when, and you will be severely punished for any failures."

With that, she slammed the door and went out to a morning's sun bathing on the beach. I obviously would not be picking up a tan on this holiday, although for a moment I had been worried that she would drag me naked and collared down to the beach, to kneel beside her applying sun tan lotion and pouring drinks.

The morning passed slowly, the strain of keeping the butt plug in was beginning to tell, but I kept my self as rigidly still as I could. It felt as if my arsehole had been widened to the size of a tunnel, and the plug had shifted up to press painfully against my insides, but the fear of her belt landing over my welted arse again was sufficient motivation.

She returned for lunch, which I served her on the veranda with a nice white wine, "Stand up facing the beach, bend over, both arms on the wall."

I did as I was told, naked, staring down at the sunbathers enjoying themselves with my hard cock barely hidden from them. She leaned in and removed the butt plug, I've never felt such relief, and I could feel my hole slowly begin to contract, "You did well slut, assuming you behave, you will only need to wear the next size, for two hours tonight."

"Thank you, Mistress."

"Return to your position by the door, I'm going back to the beach," as she was leaving she lowered the thermostat so that the AC was blowing on max.

I was kneeling by the door again, there was a certain strain on my legs, it wasn't as painful or awkward to maintain my position now that the butt plug was out, but the chill from the AC was making me shiver.

After two hours I was very very cold, I sort of drifted off and wasn't paying attention when the door opened.

"Good evening, Mistress," I managed to shout out in time.

She laid a hand on my chest, "Chilly my pet."

"Yes, Mistress."

She removed the chastity device from around my cock, "If you want to warm up, you may stand on the veranda, left-hand side, outside corner."

The veranda wall wasn't high, but I was pretty sure my cock and balls would not be visible from below, so I gladly thanked her and made my way outside.

After a few minutes, she joined me, "How do you feel my pet, better?"

"Much warmer, thank you, Mistress."

"Turn around." I turned to see her standing in a short red kimono with another butt plug in her hand, it looked a little wider than the last one and was at least an inch longer.

"I forgot to bring my lube slut, open your mouth and prepare this for insertion."

I did as I was told, and she started to move the butt plug in and out of my mouth, I was giving a plastic cock a blow job, along with having the butt plug in my arse for half a day, it all felt dreadfully close to the line of our agreement to me, but I didn't complain, my arse didn't need to be raging fire again tonight.

"Enough bend over," she commanded.

I assumed the position I had at lunch time and she took her time to insert the plug, it certainly felt as if it reached further inside me, and I felt my hole stretch around its width.

"Good slut," she sat on her chair and I quickly assumed a kneeling position in front of her, her robe opened to display her breasts and pussy and my cock hardened a little more at the sight. She crossed her legs and raised a foot up towards me, "Oh dear, my toes appear to be a little sandy, be a good slut and clean them."

I licked the bottom clean first, then the top, slowly I took each toe into my mouth and sucked on them, she was smiling down at me as she pulled a vibrator from her purse and applied it to her pussy, she came before I had finished the second foot. She stood and gave me a look, I knew what she wanted, I moved to her chair and licked it clean of the traces of her juices.

I served her a three-course meal at the dining table inside, "You know slut, I could get you a French maids outfit for serving dinner if you want some clothes."

"This slut prefers to be naked in front of his Mistress," I lied. I wouldn't mind some clothes, but girly outfits were not on the agenda, and I wasn't one hundred percent certain I had covered that in our deal.

She laughed at me, "Liar, I'll keep you naked, for now."

An alarm went on her watch, and I was bent over her knee to have my butt plugged removed, two hours with the thing inside me didn't feel great, but it was much better than twelve damn hours.

She caressed my cheeks, "The swelling and redness are going down slut, I like your arse glowing in the dark." I stayed perfectly still, "But not tonight, tonight I have a new game for you."

She commanded me to the spare bed room, we had not even opened the door so far, inside the room was almost empty, no bed, a chair and a couple of cupboards was all I could see except for the two ropes with leather cuffs hanging from the ceiling.

"Tonight we are going to work on your self-control," she cuffed me in, then using a remote control slowly lifted me up until I was standing on tip toe.

"You came without permission last night, that can't happen again, you must always warn me at least five seconds before you cum, always."

I was trussed up as she stood in front of me, she let the red kimono fall to the ground, she was completely naked, her red hair fell down her shoulders and parted to either side of her swollen breasts, the small runway of red hair above her pubic mound pointed to her pussy and screamed, "Fuck here." My cock hardened once more.

"Good slut, I need a good hard cock for tonight's instructions."

She then surprised the hell out of me by falling on her knees, she looked at my swollen cock, opened her mouth, and took it to the root in one smooth motion. As my wife, she always had a hand on the shaft between my balls and the head to stop her from taking too much length when blowing me, as my Mistress she swallowed the whole thing with ease.

She moved her head back, licked around my cock head, under the ridge between the head and the shaft, her hand pulled on my skin and she rolled my foreskin playfully back, my cock began to swell a little more if that was possible.

She then gave me the best blow job I'd ever had, her mouth easily accepted my cock as she slid up and down its shaft, her tongue worked me while I was inside her, her hand worked my balls, and then she was fingering my arsehole, I felt the familiar tingling deep down in my sacks, "Mistress," I called.

Her mouth came off and her hand wrapped itself around the base of my cock squeezing it very roughly, "Good slut, just a little pre cum leaking out, that's exactly what I wanted to see."

She waited a few moments then returned her mouth to its task, over and over she brought me close to orgasm, and over and over she stopped me when I called out, my balls were blue with the pain of refused release, especially when she squeezed them, she mouthed me for close to two hours until finally, she stood.

"Enough, run my bath." The remote opened the cuffs, the strain on my legs gave way and I crashed to the floor, "very well she said, if you like the floor so much, crawl to the bathroom." I began to crawl, her foot came down on the back of my neck, "Crawl I said," I lowered my body as close to the floor as I could get and crawled away from her.

After her bath I ate her pussy on the veranda, she had a six sided dice with her, she rolled it, it came up three, that's how many times I would have to make her cum before being released for the night. My tongue was swollen and my jaw was aching by the time I was finished, I had repaid her, more than repaid her for those two hours of cock sucking.

It was close to midnight when I finally was allowed to wank into my dog bed, the stream of spunk that came was probably the biggest and thickest I had ever had, it puddled on the bed, and I felt my stomach turn a little as I lay down on it and hardened against my skin.

Day 5

The next few days were more of the same pattern, my Mistress stretched my arse further by adding slightly larger butt plugs each day, I serviced her orally, and she used my cock as a live dildo at will. I was allowed to cum, once, at the end of the day, into what was becoming a very grungy dog bed.

I was spanked for her pleasure and as a punishment, she wanted my arse red at all times, she used different instruments, a paddle, a tawse, her hair brush, a whip made up of hundreds of strands of fine hair.

She had decided I would soon be ready to accept a cock beating, and I was now on a regime of Viagra which kept me almost constantly erect, even without the promised beating, my cock was painfully sore.

She was constantly performing new acts of degradation and humiliation, last night she had given me an enema laughing as it took its effects on me. I now slept with the day's butt plug in my mouth like a child's pacifier, sometimes she cleaned it before giving it to me, sometimes.

I knelt by the door shivering under the AC, "I think we are ready to progress with your training my pet, set two places for lunch," and then she went back to the beach.

I heard her lightly laughing as she turned the key in the lock of and opened the door, another woman stood beside her, she was in her late thirties, very tanned, slightly overweight but not obese, she had short blonde hair and was wearing a robe under which I could see a one piece bathing suit, at least one size too small IMO as it strained around her voluptuous figure.

"Oh he's perfect Lorna," she thrilled, she stood in front of me, "greet me."

"Welcome, Mistress," I stammered.

"You'll have to forgive him, Melanie, he's only very recently in training, slut, you greet a Mistress properly by kissing her feet."

I knelt in front of her and kissed both sandals, "Better," she said.

I was constantly up and down from my kneeling position during lunch, fetch a clean knife and fork, another napkin, more wine, all the time the two talked about how hard it was to break a new slut into service. Melanie gave my Mistress some ideas that I wasn't too happy to hear, but I kept my head down and instantly obeyed their instructions.

After lunch was cleared the two stood up and held hands, "Coming slut?" Melanie said to me, and I followed them to the bed room.

The two were very eager, they hurriedly dropped their clothes as they rushed to the bed, soon lying naked beside each other.

"Slut, come, stand here," I did as my Mistress instructed, "Melanie and I are going to fuck, you will play with your cock while we do so, you will not come, you will not close your eyes at any time, you will watch the two of us enjoy ourselves with the joy a good slut has for her Mistresses pleasure, am I clear."

"Yes, Mistress," I moved my hand to my cock and slowly started to move it up and down the shaft.

Melanie looked at me, "He's very dry, why don't I give him a hand?" She leaned over and took my cock in her mouth she worked it for a few minutes, spitting on it, then more mouth work, and finally some more spit, "There now, you're all lubed up, that should last you for a few hours."

She dismissed me from her attention, and with a leer of pure leachy grabbed my Mistress by the shoulders and pulled her down into a long kiss. I was stunned again, I knew my wife was straight, but her tongue moved into Melanie's mouth with gusto, their hands explored each other bodies as they lay there.

Melanie's hand had been playing with my Mistresses clit for at least five minutes, my Mistress was now lying under her, her legs spread wide open allowing Melanie's fingers access to her pussy.

I could see how wet she was, I could hear her panting and encouraging Melanie, all the time I played with my cock, I was in a high state of excitement, but I managed to control myself. I didn't want Melanie's hand to be the one wielding the whip across my arse if I came by accident.

Melanie's head was now between my Mistress' legs, she was screaming with pleasure and her words drove Melanie's on, her hand reached up, and she played with My Mistress tits, she nipped them, squeezed them, pinched the nipple, it was obviously painful as my Mistresses back arched, but she only screamed, "Yes," more loudly.

I could see her eyes darken, I knew that look, she was on the cusp, Melanie drove her tongue deeper into her pinkness, "Fuck yes, you're going to make me cum," it felt like the entire apartment shuddered as it joined her in the fury of her orgasm.

Melanie worked her mouth slowly up My Mistress panting body until their mouth and tongues once again joined, after a few minutes my Mistress made her way down Melanie's body, to end up with her mouth around the others woman's pussy then she fiercely drove the other woman to her own orgasm.

In my slut state I was watching my Mistress give another woman pleasure, but in part of my mind I was watching my wife eat another woman's cunt and by the sounds, she was making thoroughly enjoying the experience.

She put the tips of her finger over Melanie's mouth, "Wait a moment."

She opened the gray suitcase, and pulled on a strange set of black pantyhose, she slipped a plastic cock into them, and it soon peeked out of an opening close to her pubis.

"Strapless strap on, it's the newest thing." She climbed onto the bed and turned Melanie over, she spent a few minutes tonguing her from behind, both her pussy and her arse, then she guided herself between her legs, I watched as Melanie's hand came up from below and guided the massive rubber cock into her gaping opening.

Their fucking was earnest, they took turns, fucker and fuckee changing as each came.

All the time I was standing there struggling with passion and pain as I pulled constantly on my engorged cock, my only participation was to have my mouth used to clean the dildo between fuck sessions.

After what seemed like a life time the two lay sated in each other arms. "I Could use a drink," Melanie said, she then looked at me, "you will come for me slut, on ten," her head dropped down the length of my cock and she started to suck me off.

My Mistress counted down, "Ten, nine, eight..." at one, on command, I shot out a river of thick cum, the blood rushed to my head, after hours of standing and wanking I was weak, I was lightheaded, and in the background I heard my Mistress giggle then she said, "lift off."

The two showered off, I was not invited into the bathroom and waited at the open door, listening to the sounds of passion until they had once again satisfied their needs.

They came out fully dressed, my Mistress kissed Melanie at the door, "Thanks for a great day, it was truly wonderful."

"You too love," Melanie looked at me, "good night Slut."

"Good night, Mistress," I responded.

She walked over to me, took her shoe and ground it slowly into my cock and balls, "A little something to remember me by," she said as I cried out in pain.

It was after Midnight and I was kneeling by my Mistresses bed as I should, as I had come in Melanie's mouth, I was not sure if I would have to perform the wanking ritual before being allowed to sleep.

My Mistress had not said anything for quite a while and I was left wondering what was going on, I knew I couldn't lie down without permission. She looked at me, took off her nighty and threw it to the floor, her panties soon followed, she patted the bed beside her, "Come up here Joe, I could do with a real fuck tonight."

The second week

Mistress removed the butt plug from my arse and cleaned it, she removed the dildo which went along with the strapless strap on from her purse and put them beside each other on the table. Causally measuring them, they looked awfully close to the same size to me. I found it amazing that for the last two hours I had been sashaying around the apartment with that huge thing seated in my arse, and it hadn't been uncomfortable, Mistress smiled at me, "I think you are about ready my pet."

My stomach turned, I knew what was coming, and I couldn't stop it, I had demanded no guys, and she had kept that promise, but that didn't mean she wasn't looking forward to fucking my now stretched arsehole, I wasn't even sure if I was technically a virgin or not.

"May this slut ask his Mistress a question?"

"Of course."

"Am I still a virgin, after all the butt plugs and things, I'm not really sure."

"Yes, slut, technically you are still a virgin, a status I look forward to abusing you of very soon."