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To my surprise, my first story was received quite well! So thank you to everyone who read and liked it, hopefully I can continue to make enjoyable stories.
As per a request in the comments on the last story, I am writing this. It’s a stand alone from the other story, but follows similar lines. It’s also going to have a long build up, but I’m hoping the ending will compensate for it. Hope you enjoy.
Stefan was in the midst of passionate self-love as he penetrated himself with his toy. Brushing up against his prostate, he moved his dildo in and out of his throbbing hole, chasing the pleasure that came with every thrust. Each thrust he felt every ounce of pleasure surge through his body. It was almost unbearable. After an hour of making love to himself, and cumming multiple times from anal alone, he was finally spent. Basking in his afterglow, he was sated but not satisfied. He felt like he was missing something. After cleaning up, Stefan took time to have smoke and went off to sleep wondering what he was missing.
Stefan is a 26 year old man with wavy blonde hair, bright green eyes and a gentle jaw line. He was always sexually curious, and often went out of his way to explore his body. His list of fetishes has grown and shrank as the years went on, but he has often come back to anal. He found sensations he never knew a man could find. He would often pair chastity with his anal play. He found it enhanced his experience by not allowing him pleasure, increasing his need for release. During his chastity stints he would often have erotic dreams of submission. His mistress would order him to do tasks and he would gladly oblige, as his mistress would grant him pleasure if he did. Stefan would often awake from these dreams sweating and panting like he had experienced these events in waking. As it happened, after having pleasured himself completely, he was having one of those dreams right now.
As Stefan awoke, sweaty and heaving, the realisation struck him. He got out of bed, got some coffee and had a morning smoke. The excitement surged through his body as he opened his computer. He heard about websites offering mistresses to connect with. Hoping to find someone to carry out his desires, he feverishly searched forums looking for someone accepting of his particular needs. Unable to find anything before he had to go to work he suspended his search.
Stefan worked at a small office building in the city. It was mainly busy work but he was content with it. He had some down time today, so checking around him making sure he wasn’t being watched, he decided to start searching for a mistress so sate his desires. Shortly after beginning his search he hears a breathing besides his head. He turns to see one of his coworkers standing behind him with her head close to his looking at his screen. Startled, he closes his search and shakily asks what she is doing. She lets out a short chuckle and returns to whatever she was doing previously.
The woman’s name was Alisha. She was an average looking 25 year old woman. Dull brown hair, hazel eyes, average build, nice curves. Over all, she was pretty ordinary and easily missed. Her personality left little to be desired, but had a certain air about it. Stefan had often thought about asking her out for coffee because he didn’t have much going for him as far as women went to begin with.
Bothered by the recent events with Alisha, Stefan promptly returned to work. Returning to his cubicle from being away doing a task for his boss, he was preparing to return home when he found a slip of paper on his desk marked from Alisha with a phone number on it. Curious as to what her intentions were he saved the number in his phone. After waiting a few days, not wanting to seem to interested to desperate, he texted Alisha’s number. After a brief conversation about what she saw and why she gave him her number, she asked if he was interested bahis firmaları in maybe letting her share in his fetishes. He was stunned that she asked him this. He took a few minutes to contemplate his situation and told her he would agree as long as they set a few ground rules. She agreed, and they decided to meet at a yet undecided date. So they met up, shared in conversation and decided on an agreement to enjoy each other’s company and share
in their sexual desires.
It’s been about a month and Stefan has slowly introduced Alisha to his fetishes. Alisha found one of his fetishes rather fascinating. She found male chastity to be extremely arousing. Being able to control a man in such a way intrigued her very much. “What do you think about giving me the key to your caged cock Stefan?” Alisha asked. Startled by this question but also aroused slightly from his erotic fantasies he had often, he thought
for a moment.
“As long as I can ask to be removed if I’m uncomfortable with it in anyway, I guess it would be alright,” Stefan said.
“Of course!” Alisha Agreed happily. Even though Stefan appeared to be hesitant, he knew this is what he wanted all along.
They started off slowly, with only having Stefan in chastity for a few days at a time, then a week, then a couple weeks. Alisha wasn’t quite into anal at this point, but Stefan was determined to make his fantasies a reality. After about a month and a half into their arrangement, they decided to go on a proper date. They enjoyed their meetings, but felt like they wanted to sit down and have a nice dinner. Stefan was, of course, in chastity tonight. And Alisha was well aware of his arousal from being caged in public. She couldn’t help but tease him under the table. She was rubbing up and down his thigh with her feet, sometimes bumping into his cage causing Stefan to jump a little. After the lavish dining experience they decided to head to Alisha’s house. Which was odd because they never met at her house as Stefan had all of the fetish toys they needed. After arriving to her house, Alisha stopped in front of her door.
“Close your eyes and do not open your eyes until I tell you to, understand?” she asked sternly. Stefan agreed, albeit slightly worried. She led him inside into a room, sat him down, and told him to wait. He heard her light footfalls wander off into the distance. After what seemed like an eternity, he heard her footsteps return.
She whispered into his ear, “stand up and follow me. Eyes closed,” nibbling at his ear as she withdrew her mouth from his ear. He eagerly got up and followed her into the adjacent room. She sat him on a couch and tied his hands and feet with rope. They often indulged in bondage activities, so this wasn’t surprising to him. She nibbled up and down his body and teased his caged cock, making him squirm.He was very aroused at this point because he has been locked up for two months already. She suddenly stopped and withdrew from his body and told him to open his eyes. As he opened his eyes he spotted that there were candles lit all over the room, lights dim and Alisha standing there… and she was certainly stealing the attention from the surrounding ambience of the room. She was dressed in just a black lace bra and matching panties and a pair of heels long enough to accentuate her legs, but short enough to add
elegance to the outfit. Stefan was stunned.
“I’m going to tease your caged cock with this massager till you can’t stand it, then I’m going to give you something even better,” she said with a slight chuckle.
“But first, I need you to change into something I picked out for you.” Stefan was surprised, they never did something like this.
“Change into what?” he asked. Alisha pulled out a very short black dress and a black wavy wig she had bought a few days prior. Stefan slowly felt his cock swell inside his cage to the point it was uncomfortable.
Alisha kaçak iddaa noticed this and said, “I see that dressing in women’s clothes excites you.”
Stefan looked embarrassed, “I had never thought about it till now.”
Alisha looked at him with a devilish grin, “Well here is what’s going to happen. You are going to change into this outfit, I will tease you as long as I desire, and only until I’m satisfied will I allow you to cum. But you will not be let out of your cage to cum, understood?”
“Yes Alisha,” Stefan replied.
“Oh and one other thing,” Alisha continued,”You will call me mistress and your name for tonight will be Stefanie or sissy, understood?”
“Yes mistress,” Stefan agreed with but a slight hesitation in his voice.
Alisha untied Stefan from the ropes and told him to put on the outfit and wig, which he did so. After dressing himself he sat back down expecting to be tied back back up, only to be told to go on his hands and knees. He hesitated at first but did as he was told. Alisha bound his hands and feet down to the couch so that she had complete control of Stefan’s body. Alisha slapped Stefan’s ass and Stefan let out a soft moan. “Do you like having your ass slapped by your mistress sissy?” Alisha said slapping his other cheek.
“Yes mistress,” Stefan managed to moan as Alisha slapped his ass again. After a few more slaps, Alisha got her vibrating massager out and put it on the lowest setting. She rubbed the massager down his spine, sending tingling waves all over Stefan’s body. She ran it across his lower back and over each ass cheek. Stefan twitched a little as she brushed his taint with the massager. She eventually Moved the massager to Stefan’s nipples, slowly circling each till she would brush the nipple itself very softly causing Stefan to moan with pleasure. Alisha, after being satisfied he was aroused enough, moved the massager to Stefan’s cage. Stefan bucked his hips as the sudden pleasure matched with his arousal sent waves through his entire body.
“Tell me when you are getting close Stefanie. If you cum I will punish you. Though I won’t mind it will be fun for me, but I cant say it will be enjoyable for you,” Stefanie said while turning the massager up to medium. Stefan couldn’t reply. After having his cock caged for so long this amount of stimulation was going to make him cum very fast.
Within only a few minutes Stefan managed to moan out, “I-I’m going to cum mistress.” Alisha promptly turned up the massager to full, and Stefan let out a stream of cum. His cock danced in its cage and stream after stream hit the couch and emptied his balls.
“I told you not to cum sissy. Where is your self control?” Alisha demanded with no remorse as she slapped his already red ass cheeks.
“I’m sorry mistress.” Stefan replied.
“Sorry? No you aren’t sorry, but you will be.” Alisha then left the room and Stefan was there on his hands and knees not knowing what was going to happen. Even though he had just cum, he was aroused by the thought of being punished for cumming when he wasn’t supposed to, even though he had no control over what happened. Alisha returned, but Stefan could not see here because he was still facing away from her.
She moves her mouth next to his ear, “You better get ready Stefanie, I’m going to fuck your ass all night till you are just a limp pile on my couch.” These words made Stefan shiver with excitement as Alisha slapped his ass once more. He felt a cold liquid drip down his ass hole down his taint coming to rest on his balls.
Alisha slowly worked the lube around his hole, making sure to tease him to allow his ass to accept her finger without resistance. Alisha had been reading up on anal play and how to make it as comfortable as possible. As she worked her finger around she started pushing it inside. Slowly she managed to get it all the way into his throbbing entrance. Alisha had also been reading up on male kaçak bahis pleasure from anal, when she came across the prostate. She knew she could use this to her advantage. Alisha found his prostate with her finger and began to softly press it. As she did Stefan let out a pretty sizeable moan. “I found your sissy cum button Stefanie,” Alisha teased.
“I’m going to make you drip cum from your cock, while not allowing you to orgasm. Does that make you hard?” She glanced down at his cage and noticed his cock swelling with every press of his prostate.
“Yes mistress,” Stefan managed to reply. After a session of prostate milking Stefan had felt like he had been cumming like a leaky faucet, even though it was only about a tablespoon or two of precum. His cock was burning and he needed release so badly at this point he was shaking.
“Aww, you got precum on your new dress just from me playing with your ass. You really are just a sissy, dripping from just your ass being fingered,” Alisha teased as she withdrew her finger, his hole twitching still from the pleasure.
Alisha then forcefully pressed her strap on she had bought previously against his hole. As she inserted the 6 inch dildo, Stefan moaned with extreme pleasure. As Stefan’s fantasies came true Alisha continued to move her length inside of him. With each thrust he felt pleasure he never knew existed; more pleasure than he ever got fucking himself. Alisha adjusted her angle to better rub his prostate, and as she did Stefan responded with even louder more sensual moans. As time went on and Alisha fucked him even harder and faster, Stefan felt a warming sensation in his cock. He knew he was about to cum from his ass. As Alisha noticed him bucking against her fake cock, she kept fucking him even faster responding to his need for release.
“If you cum Stefanie, I will never unlock your cock because you wont need to use it to cum ever again,” Alisha said, knowing it would arouse him even further. And she was right, as she said those words, Stefan came harder than he ever had before. His ass and cock twitched and spasmed. His cock dribbling cum as Alisha continued to fuck him through his orgasm. Stefan felt the waves keep coming for about 5 minutes, then even after his body had calmed down Alisha kept fucking him, albeit slower.
“I knew you wouldn’t need your cock after I was done with you tonight,” she remarked. Shortly after saying that she noticed Stefan begin to moan louder and louder and starting pushing against her fake member again.
“For each time you cum, I will add a year to your chastity time. Do your best to hold back sissy slut.” As Alisha said that Stefan came again. Stefan realised the situation he was in and he loved every minute of it. After hours of passionate love making, and about 5 orgasms later, Stefan could no longer hold himself up. As Alisha stopped assault on his body, she nibbled parts of him and kissed all over. Stefan felt her dildo leave his spent hole as she left to clean herself up and get a cloth to wipe him down. After cleaning both him and herself up, she helped Stefan to bed where he quietly drifted off into a deep sleep.
As Stefan awoke the next day, Alisha by his side, he got up to have a smoke. As he walked outside and pulled the cigarette into his mouth, he inhaled deeply as he reminisced in the afterglow of what had happened last night. He then returned to the bedroom to find Alisha missing. Thinking nothing of it, he made his way to the bathroom to relieve himself. As he looked down he noticed something odd about his lock on his chastity. Alisha had glued closed the keyhole on the small brass padlock. She walked up behind him in the bathroom leaning her head gently on his shoulder.
“By my count, you’re never going to be taking that off anyway. So I decided to make it a little more permanent.” Stefan didn’t even hesitate, and turned over his shoulder to give her a deep kiss. Surprised, Alisha gave in and kissed him back, for this is the first kiss they shared outside of the bedroom. Stefan’s cock would be locked for a very long time, but he knew it didn’t matter because he could get release in more fulfilling ways.
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