Masturbation Month 2023 May 9th - (Link to Part One)
There was a pattern Cynthia wanted to try out with Frank; pleasure, craving, and calm. As her tongue played with his ass, she considered her timing. Relaxation was essential, and she didn’t want to get him excited in a tense way, more in a relaxed way. She rubbed his taint gently as she slowly rimmed his hole.
Then she climbed off the table and massaged his neck and scalp again. She ran her fingers through his hair over and over again, bringing him back to calm.
Frank felt a bit like he was floating, especially with his eyes closed. He was in sensory heaven. His ass yearned for more, but he was so relaxed that he simply trusted Cynthia would get there eventually. Seemed like she was in no hurry to fuck him, so he was in no hurry to get fucked.
Working her way down Frank’s back one more time, she finally arrived at his ass. She picked up the small dildo from the bed and coated it with lube. Then she took a hand full of Frank’s hair and pulled it ever so gently while her other hand pressed the dildo slowly and firmly into his ass.
“Be a good boy and take this for me, Frank.” She murmured.
“Oh! Yes, Ma’am! Oh, yes!” The dildo she held claimed a home in his ass.
“Well done.” She commented, and Frank smiled. He loved to please her and heard the approval in her voice.
Cynthia began stroking into Frank very, very slowly. She tilted the dildo a little this way and that, until she got the loudest moan from Frank. Then she kept that angle, continuing his slow fucking. When his body showed signs of getting tense, she stopped the motion of the toy and ran her fingers through his hair until he settled. She continued this cycle repeatedly for what felt to Frank like an eternity.
The endless pattern was pleasure, craving, and calm. Pleasure, craving, and calm. Now he was most definitely floating, must be at least a foot off the table, Frank thought. He was in this amazing zone where he wasn’t frantic to feel more, because what he was feeling was so delicious. Different. Slower. Yummy. Then the toy was gone, and so was Cynthia, but not for long.
Cynthia pulled the toy out gently and set it on the towel on their bed. She grabbed the larger purple dildo and coated it with lube. Moving back to the table, she grasped Frank’s hair again, this time a little more tightly.
“Now be a good boy and take this one for me, my love.” She pressed the toy into him.
Frank was so relaxed that his ass opened easily for this new, and larger, penetration. It felt like their big purple toy, but his eyes were still closed so he really didn’t know. He felt the fullness of the girthy toy and thrilled to the sensations. Then Cynthia began the same, very slow stroking in and out, just like with the smaller toy.
Frank’s level of pleasure increased significantly. This larger toy gave him a warmth and a tingle in his belly and pelvic area. He completely forgot about his cock. Later he would marvel at that. His world became the slow invasion of the toy, and then its withdrawal, over and over. Then the pause, her hand in his hair, and finally, longer than he wanted to wait, the stroking began again. Pleasure, craving, and calm.
Frank was astonished at how intensely good it felt. It was practically the same level of pleasure as just before an orgasm. He could stay here forever. Oh, yes!
Cynthia decided this was the moment. She left the purple toy in Frank’s ass and picked up the short fat toy from the bed. This was a gamble. Frank had never taken a toy this wide before. She'd just gotten it today. Coating it with lube, she gently removed the other toy from his ass, tossing it on the towel.
Cynthia pulled his head back a bit this time with her hand full of his hair. She touched the toy against his ass and leaned down to speak her words warm and rough into his ear.
“You will take this toy for me, Frank. Understand?” Her voice sounded calm and full of power. He melted inside. His ass melted. Everything melted with the sound of her words. Her tone said he did not have a choice, and that excited the fuck out of him.
“Yes, Ma’am. I understand. For you.” Frank relaxed his whole body and mentally invited in whatever toy Cynthia wanted him to take. He trusted her.
She took it slow this time. Quite slow. So slow that progress was almost imperceptible. He waited, breathed, and concentrated on opening. It felt huge!
All in a moment Frank felt overwhelmed with emotion. He felt so fucking open and vulnerable. So completely and without question, hers. He would take this toy for her. Fuck yes, he would! A little more stretching and finally the feeling of his sphincter closing behind the head of the toy. Yes.
“Frank! You are the best boy in the world. Well done, my love. Well done!” Cynthia gave him a moment to relax into the toy’s girth before she moved it any further.
Frank’s heart swelled and he got the warm fuzzies. He did it! For her. He was hers. His body was buzzing with pleasure. His ass was stretched and full. And Cynthia was kissing his neck and saying sweet soft words into his ear about what a good boy he was. Heaven.
Frank was soon to discover that heaven could get better. Cynthia gently slid the toy all the way in. It was not long, but very wide, and the widest part was the head. The effort and pride of stretching to get the head of it inside him turned into exquisite pleasure as it filled his ass completely. It felt so fucking big!
Cynthia was still murmuring in his ear as she gently turned the toy just a little. Intense sensations of pleasure took his breath away. He’d never felt this much pleasure from something in his ass.
Cynthia’s hunch that a wide toy would send Frank into previously unexplored territories of ass bliss had been correct. She began a very slow stroke and Frank started moaning loudly every time it went inside him. Pleasure, check. Craving, check. She started to pause for the calm, like she’d been doing with the other toys, but Frank had other ideas. The pleasure, craving and calm pattern wasn't what his body was screaming for. In other words, his craving took over.
“Please, Ma’am! Please don’t stop! Cynthia, please!” Those were the only words Frank could get out as he felt a kind of gathering inside him, like there was a precipice he would soon be falling from, in the most incredible of ways, as long as she kept fucking him. There was something waiting and needing more, simply more. He began arching his ass up into the toy, reaching for it as Cynthia pushed it inside him.
She sped up just a little and held that pace steady for less than a minute before Frank fell off that precipice.
“Oh my GOD! Oh my GOD!” Frank yelled, as he felt it build. Then words became impossible as he trembled and shook. His entire lower body tingled and felt warm. Waves of joy and intense pleasure traveled over his entire body and his muscles spasmed uncontrollably. The waves just kept coming and coming, seemingly spurred on by Cynthia’s continued toy action. There was a bright shining light of pleasure in his ass, and nothing else existed. Finally, she slowed down and stopped altogether. He lay there helpless, unable to speak, trembling.
Cynthia rejoiced inside and did a mental fist pump. This had been her plan all along! They had never been able to get Frank to a prostate orgasm before, and if she wasn’t mistaken, that’s what just happened. He’d never been disciplined enough about the abstaining and edging part. Well, that’s all they’d been doing since that cage got locked onto Frank's cock three nights ago. Then she saw the small puddle of come that had oozed out of him and smiled. Yes! Pleasure, craving, and calm had worked!
She withdrew the toy carefully. He finally opened his eyes to look; he had to see the toy that sent him to the moon with pleasure, as well as the woman who wielded it so well. It was a new toy! And just as wide as it felt. The woman in pink was even sexier than before his ass adventure, if that were possible.
Frank closed his eyes and sank back into the cushion. While waiting for him to return to Earth, she took off his cuffs, untied the scarf and took away the spreader bar. She smoothed his hair and kissed his cheek.
“Good boy.” She said, simply.
Masturbation Month is celebrated every year in May. Let yourself sink into self-pleasuring and join the fun! Some of us keep an orgasm count. Ruby: 8