Coin-Toss Pegging

This is the fourth in the series of Margaret and Michael stories. If you like this one you'll like "Birthday Butt Play."

"Oh my god!" Margaret exclaimed. "My hand is all the way inside you."

Michael knew. He couldn't always tell how many fingers Margaret had stuffed up his ass but he could definitely feel the moment when the widest part of her fist made it through his outer ring and into his anal canal. He suddenly felt fuller, but slightly less stretched. It was an amazing feeling.

But we're getting ahead of ourselves here.

Margaret and Michael were a well matched couple. Sexually well matched. They both had strong appetites and their kinks were highly compatible. In particular they both loved anal sex, both giving and receiving. They both enjoyed the feeling of having their asses stretched open by the other person's fingers and they both loved thrusting a cock into the other person's butt - a silicone or flesh-and-blood cock, depending on who was doing the thrusting.

Therefore it was no surprise when they decided to flip a coin to decide who would sodomize whom. They'd been making out for about an hour and they were both floating on an endorphin high. Michael had ravished Margaret's tits for a while using his mouth and fingers and Margaret was sure she was going to have some bruises. Margaret had spent quite a while seeing how much of Michael's 7" cock she could fit into her mouth - not all of it, to her regret - while also taking time to fondle and lick his balls and occasionally tease his ass with her lubed fingers. And Michael had spent considerable time worshipping Margaret's pussy - he loved few things more than burying his head between her legs, licking her clit and labia while finger fucking her.

Michael's cock had stayed hard the entire time - the product of a healthy lifestyle with some assistance from a boner pill taken before they started. As was quite common with the couple, the first bit of "foreplay" that morning was when Margaret had walked up to Michael with a pill and asked if Michael was hungry. The ritual itself always made Michael hard and Margaret wet since it said - more clearly than words or other actions - that they were both Down. To. Fuck. And, it meant that they could fuck for a long time. Which they had done.

"I'm so horny right now," said Margaret. "I kinda want you to fuck my ass. I think I need that level of intensity to finish this marathon session."

"That sounds very tempting," responded Michael. "But the only problem is that I was just thinking that you should fuck my ass. It's been a while since you've given me a proper pegging."

"True," agreed Margaret. "But it's been a while since you've properly seen to my ass also. And it's not really practical to do both."

"I've got an idea,." said Michael. "Let's flip a coin to decide who gets their ass fucked. Does that sound like a good plan?"

Margaret agreed and Michael grabbed a coin. "You flip it, I'll call," he said. "Heads!"

The coin came up heads and Michael gave a smug smile. "I need this," he said. "I haven't had a good prostate massage in a while and I really want to come with a toy inside me."

It was a huge difference from when Margaret and Michael were first married. Back then all discussion of "butt stuff" had been very tentative and nervous because they were both worried about seeming "too" perverted and slutty. "Good girls" don't enjoy giving or receiving anal and these societal expectations held back their desires for a while. Those hesitant days were in the distant past now because they had long ago realized that they were kindred spirits who loved both the sensations and the taboo nature of buggery. When Michael was fucking Margaret's ass there was the extra enjoyment of the tightness on his cock, and for Margaret there was the stimulation of an often neglected area. When Margaret was fucking Michael's ass there was the prostate stimulation plus the excitement of the role reversal.

With the plan decided Margaret grabbed the harness and slid it up her legs. She grabbed the three compatible dildos from the well-stocked toy drawer and asked Michael, "Well? Which will it be?"

There was a large purple dildo that was 8" long, veiny, and improbably thick. There was a medium-sized black dildo that was a bit under 7" long, smooth, and a bit less girthy. The third choice probably should have been a small one but that wasn't really Michael's style. Instead the third one was the same size as the second one but made of glass instead of silicone.

Michael pointed at the large dildo. Margaret just rolled her eyes. It was almost always the choice. The glass dildo was chosen occasionally because of how cool it felt inside Michael's body - but it didn't vibrate. The other medium-sized dildo hadn't been chosen in years. "You're a size queen," Margaret said. Michael just grinned.

Margaret slid the large dildo into the harness and tightened the straps, but it was not yet time to peg Michael. There was much more to do before they got to that stage. The exact details varied from time to time but one constant was that whoever was wielding the penis made the rules. "Get your mouth over here!" Margaret ordered as she lay back on the bed, holding the base of her prosthetic dick. Michael obediently shuffled over.

For not the first time Margaret wished that she had nerve endings in the dildo. It was hella sexy watching Michael give her a blow job but she wished she knew what it felt like. He always looked like he was a good cocksucker and she hoped that somebody she'd get to see him demonstrating his skills on a bio-cock so that she could find out for sure.

His enthusiasm was apparent as he licked up and down the sides of the shaft, kissing her hand at the bottom. Occasionally he would lower his head enough to be able to reach her labia with his extended tongue but he mostly focused on the large toy. "Don't just lick my cock." Margaret said. "I want to see my cock in your mouth and down your throat!" she ordered.

Michael hadn't really mastered the art of deep throat, and the large-and-girthy dildo probably wouldn't fit in his throat anyway, but he was happy to try. He lowered his mouth over the head of the cock and descended until it was pressing against the back of his mouth. He coughed and sputtered a bit as he tried to force it deeper, and then came up for air. Michael then wrapped one hand around the dildo, lining up his hand with a familiar vein. He knew that he'd taken the dildo that far before and he wanted to try to go deeper. Once again he lowered his mouth over the silicone cock and pushed down. His eyes watered and the pressure on his throat felt uncomfortable but he persisted and he felt the cock go part way into his throat. His lips pushed his hand down and he smiled inwardly with the satisfaction of achieving a new personal best.

He came up for air and gave Margaret a cock-drunk smile as he stroked her silicone cock, before his mouth descended down her shaft again. He would occasionally reach up and squeeze her perfect C-cup breasts while sucking her cock, but mostly he leaned on one hand while stroking her phallus with the other hand.

This continued for a while until Margaret pulled his head from her drool-soaked penis and ordered, "On your knees, butt slut!"

The name calling increased the intensity of the scene that they were creating and Michael groaned quietly. And, of course, he obeyed. He assumed the position, on his hands and knees in front of his sexy lover.

Margaret grabbed an industrial-sized bottle of water-based lube and squirted a huge blob on Michael's exposed anus. "This might feel a bit cold," she said, intentionally giving the warning too late to be useful. Michael was hardly going to complain though, especially since Margaret immediately started rubbing the lube around his anus, taint, and balls. These areas were all sensitive, didn't receive enough attention, and felt marvelous as Margaret's lube-slick fingers pressed and rubbed along them.

Margaret's fingers didn't stay outside for long. One finger slid in effortlessly and Michael groaned as it happened. Margaret didn't waste any time and almost immediately slid in a second finger. That finger also went in easily, although Margaret could feel Michael's sphincter muscle squeezing her fingers.

The last time Margaret had finger fucked Michael she had taken a long time to work her way up to, eventually, four fingers inside him. This time she was speed running the process, confident that he could handle it. Within a minute of starting she was pushing a third finger inside him. Now the difficulty started ramping up noticeably. The tips of three fingers went in easily but the digital tripod got much thicker towards the base. It was a perfect dilator.

Margaret slid her fingers in and out as she knelt behind Michael, with her other hand resting on his back. She was applying enough force that she could see her fingers going in slightly farther with every push. In remarkably short order she found that her three fingers were going in all the way. "It's time to try four fingers," Margaret said, her smirk audible in her voice. She looked in the mirror and saw Michael's face. His eyes were mostly closed, he was clearly deep in subspace, but they would occasionally open and when he caught her eyes in the mirror he smiled blissfully.

Margaret squirted more lube on her hand and on Michael's ass, withdrew her three fingers and then slowly slid in four. Once again it was easy to get the tips in but the four fingers got a lot thicker at the base. However Margaret was confident. She'd seen Michael's greedy ass swallow most of her four fingers before and she suspected that he could take more.

Margaret was patient. She'd really hoped to get her ass fucked but she was also happy to be violating Michael's ass. And given that she was doing that she was going to take the opportunity to try something she'd always wanted to do. She'd come close to fisting him once before and she wanted to see if she could do it this time. Margaret had never had her entire hand inside somebody's body (although she'd come close in the vagina of one of her previous lovers) and she really wanted the sight and feeling of doing that.

Michael had never been so full. He could feel the stretching and the rubbing as Margaret moved her hand gently in and out, rotating it slowly when it was at its deepest insertion. Progress was slow but Margaret could see her hand gradually pushing in a bit further as time went on. At this point Margaret had been fingering Michael for about twenty minutes but neither of them were getting bored. Margaret was enthralled with seeing her progress, and Michael was quietly moaning and keening as his eyes repeatedly rolled back into his head.

Margaret tucked her thumb inside her fingers and continued pushing in and out. Michael's asshole continued to stretch, gradually taking more and more of her hand, and Margaret could see the widest part of her hand getting closer and closer to sliding inside.

Suddenly it happened.

"Oh my god!" Margaret exclaimed. "My hand is all the way inside you."

Michael knew. He couldn't always tell how many fingers Margaret had stuffed up his ass but he could definitely feel the moment when the widest part of her fist made it through his outer ring and into his anal canal. He suddenly felt fuller, but slightly less stretched. It was an amazing feeling.

It was similar to the feeling when a butt plug gets past its widest point and smoothly slips inside, except this time the dimensions were so much bigger.

After a few moments of stillness Margaret started moving her hand. "Holy crap," Michael whispered. "What the fuck are you doing?"

Margaret grinned. It had been a few weeks ago when Margaret had been finger fucking Michael and had realized that she might be able to fist him. She had stopped that time because she realized she didn't know what she was doing. Since then she had done some research, so she was prepared. She had shorter fingernails than before and she had some ideas. Some of the ideas were to rotate her hand inside of Michael's body, change the shape of her hand from extended to an actual fist, and spread her fingers. She was slowly and gently trying all of these, watching to see which gave the best reactions. Stretching out her fingers to make her hand bigger while slowly rotating it seemed to be appreciated. Who knew?

"I'm just trying a few ideas I found on the internet," Margaret coyly said. "Do you want me to stop?" As she said that she reached down to his so-far neglected cock and started lightly stroking it. Michael's moaning increased in volume.

"Please don't stop. Don't stop anything. This is all amazing. I feel so full and so vulnerable and so pleasured and I want it to keep going."

Between moans of ecstasy Michael would occasionally glance over at the mirrors and spy Margaret kneeling behind him, with one hand on his cock and the other hand disappearing into his body. And he also saw the strapon dildo protruding from the harness. The harness itself looked sexy, the way its leather straps cupped her buttocks, and the dildo also looked enticing. After a few of these glances Michael remembered the original plan. That dildo was supposed to be fucking him. All this intense fisting with a side of handjob was just supposed to be foreplay.

Michael considered for a minute the possibility of finishing like this. Margaret's slippery hand on his cock felt great and he was sure that if she kept it up he would come, but he decided that that wasn't what he wanted. Fisting was great but sometimes a boy really just wants to get fucked.

"Margaret," he croaked, trying to find his words.

"Yes," she replied. "What does my greedy butt slut want?"

Michael hesitated. But then he decided for sure what he really wanted. "Your greedy butt slut wants his greedy butt fucked," he said. "I want you to fuck me with the strapon."

"Oh," teased Margaret. "Aren't you enjoying having my entire hand inside you?" - she twisted her hand more vigorously as she said it.

"Unnnnh... It's amazing," moaned Michael, "but it's different when you fuck me. I need to feel your hips slapping against my butt and driving that dildo deep inside me. I need that intense motion. I need to get fucked. Please."

Margaret decided to stop teasing and started to slowly - very slowly - pull her hand out of Michael's ass. It was a tight fit but she managed to extricate herself. She then wasted no time. She rubbed a generous portion of the lube all over her large purple silicone cock and pressed it against Michael's asshole. With her hands on his hips she gently but firmly pushed forward and the artificial penis effortlessly slid all the way into Michael. The large toy was usually a tight fit that took a while to squeeze in but after being fisted his asshole took it immediately and with no difficulty.

She turned on the built-in vibrator and started smoothly fucking his ass.

"Oh my god," said Michael. "It's... it's... it's so good. It's not better, or worse, but it's different, and it's really fucking great. The vibrations on my prostate... and it's going so deep... and the..." Michael's voice faded into a gurgle but the point was made. Fisting very good. Pegging also very good.

As was his usual habit when getting pegged Michael reached for his favourite stroker toy. He lubed it up and started sliding it along his cock with one hand while leaning on his other elbow. The sleeve was his preferred masturbation toy and he almost always used it during pegging. Maybe sometime they'd invite a third person to join them and he could put his dick somewhere else while getting fucked, but until then the stroker toy was an excellent substitute.

Often he stroked himself while getting pegged but this time Margaret decided to take over. It was a coordination challenge for her to reach around and stroke his cock, using the stroker toy, while still maintaining a steady fucking rhythm but she did it. And, not surprisingly, the sensations of being touched by somebody else - including occasional fondling of his balls with the stroking hand and his buttocks with the other hand - were better than anything he could do himself.

Michael loved being pegged and usually wanted it to last a long time, but by now he'd had something in his ass for the better part of an hour. He wasn't exactly getting sore, but he was ready for some release. When he felt the sensations strengthening and heading towards orgasmic inevitability he did not resist. Michael tensed his muscles and his cock grew even harder

It didn't take long. Michael's whole body went rigid. Margaret held her hips still, pressed all the way in, and squeezed her hand around the stroker toy as Michael shot his load all over the bed. "Don't move your hand please," he said as he slowly collapsed to the bed, with Margaret coming down with him. They lay there for a while with Margaret's trapped hand lightly squeezing his softening dick and her hips subtly swaying with the vibrating strapon dildo still deep inside Michael.

"How was it?" said Margaret.

"That was the best pegging I've ever experienced, and one of the best moments of my life. Truly amazing," groaned Michael.

"I'm glad you enjoyed." said Margaret with a grin, "But tell me, did you think I wouldn't notice that that was a two-headed coin?"