Emma - 11:15am
"I noticed a strap-on dildo in your amazing box of toys Joe. Still in the package. Have you ever been pegged?" she asked, still working her finger slowly deeper inside of me. I shook my head in denial, I hadn't. My eyes were a bit wide with fear. She started to stroke my cock and then stopped just before I would orgasm. And again. Again.
"Joe....beg me to fuck you. I want to hear you beg to be fucked..." she commanded....
I was panting with the way she was edging me. She had seemed to learn the signs that I was about to spill over and always stopped just before that happened, all the while working her finger deeper and deeper inside of me. My cock was leaking some seminal fluid, but orgasm was just out of reach. My brain felt like it was made entirely of mush, I couldn't think clearly and all I wanted to do was agree to anything that Emma wanted.
But...she wanted to actually fuck me with a strap-on. My own strap-on that I had bought but never opened. It terrified me. It was true I had bought it because I had fantasized about this very thing, but I never thought it would actually happen. It was more out of curiosity on what it looked like and felt like to hold. This particular strap-on was a 'Feeldoe', a double ended dildo that was designed for lesbian use, but the femdom community had adopted it as well. It had a smaller bulb section designed to be inserted inside the wearer and it would rub against her g-spot as she pulled out. And then there were ridges that were designed to rest right against the clitoris that would be stimulated during the thrusting in motion. The business end of the device was a realistic looking penis that was 7 inches long with respectable thickness. The entire thing was made of silicone and high quality. The skin of it was soft and squeezable over a very firm core. It was pretty realistic and would never go soft.
It was very intimidating to me, but beyond that, she wanted me to beg her to use it. I would have almost preferred she hadn't given me a choice. The primitive, conditioned male ego part of my brain was screaming that's not what a real man did. A man didn't get fucked in the ass, and a man certainly didn't ask for it, let alone beg for it. Would she think less of me after? Like...was I no longer a man worthy of respect?
But that primitive brain was being contradicted by my submissive desires, and a nearly overwhelming desire to submit all that I was to this beautiful girl. On top of that, she hadn't slowed down in extracting edge after edge from me, and I felt like I might actually lose my mind and go crazy if she did it for much longer. Rather than begging her to fuck me, I started begging and pleading her to stop edging me. I wasn't even begging to cum, I was begging for her to stop stimulating me. She shook her head though and said, "No Joe. If you won't beg me to fuck you, I think I am quite happy continuing to do this for the next hour..." she said sweetly.
I broke. Whimpering in absolute desperation and near despair, I begged in a hoarse voice, "Emma, please...please fuck me. Please Emma. Fuck me and....just.....please....."
She smiled warmly at me and let go of my cock to reach up and caress my cheek. "You are such a good boy. You will love it, I promise," she said, and her voice sounded affectionate.
She got off the bed then and went to the box opening the package containing the Feeldoe. She seemed very excited about it. She took it to the bathroom to give it a quick wash before coming back, looking at me with such hunger and desire. That look made me feel so weak. I watched in fascination and arousal as she took the Feeldoe and carefully inserted the bulb end into her amazing pussy. She had no issues doing it. "I don't think I have ever been this wet before," she marveled and then there she was, the most beautiful and sexy girl I could ever imagine with a 7 inch cock jutting out from her shaved pussy. She took a hand seductively stroked it and she looked like she was about to orgasm just from that. "Fuck I feel powerful..." she said before turning back to grab high quality lube that I had bought and never opened. I was relieved that she would be using lube, though I shouldn't have had any doubts.
She came back up onto the bed and was glowing with her desire. She seemed impatient as she took the packaging off the lube to get it open. She finally did and brought the nozzle right to my ass, squirting a generous amount inside of me. She then covered the Feeldoe with it and stroked it, looking down at me.
"Joe, I am going to fuck you and I have never wanted to do anything more. I...I might not be able to restrain myself and I don't have the patience to stretch you more. It...It might hurt..." she said, biting her lower lip as she started to rub the tip against my opening. If I had been able to think clearly, I would have seen that lip biting for what it really was. She wanted it to hurt, and that was the real reason she wasn't preparing me more.
But by this point, I was completely lost in desire for her and desire for her happiness above all else. "That's...that's okay Emma. Anything for you..." I whispered, as I trembled with fear.
She moaned upon hearing that, briefly closing her eyes before I felt the pressure against my tight hole. And pain as it started to be forced to stretch wider. She had locked eyes with me and I couldn't look away as she kept pushing. The distress of it clearly showed on my face but she didn't let up. The head popped in and I whined at the feeling and pain of it. She bit her lower lip but caressed my cheek and called me her good boy.
She kept pushing and the Feeldoe got a bit wider down towards the base, stretching me wider and wider. My groans of pain and discomfort got louder and higher pitched, but she didn't stop. The lube was letting it pass without much friction, but it was forcibly stretching me and I felt the pain deep in my body as it went deeper and deeper.
"Please....Please....oh it hurts....it hurts....please...." I started begging, but she only replied, "Shh....its okay....I've got you and it feels amazing..." and didn't stop. I was near tears as I felt her hips come to rest against my ass and she held there while I continued to beg incoherently from the pain and violating feeling of it. "Oh fuck...." she whispered in pleasure, completely buried inside of me, gazing down at me almost in rapture.
And it was that look that started to really break me. She was enjoying this SO much and was so beautifully dominant. The fact that she hadn't stopped when I complained and begged about the pain, that she had warned me about, aroused me more now. I felt like I truly belonged to her in this moment and would do anything for that look of ecstasy on her face. I accepted the pain. I even welcomed it so long as she looked at me like that.
I still showed the pain and discomfort on my face, but I now looked up at her with adoration. She let out a growl and started to pull out as I whimpered. She slammed it back in hard and I cried out from it while she shuddered in pleasure. She couldn't contain herself any longer and started to fuck me hard. The buildup was done and she just could not hold herself back, fucking me with abandon. Every noise I made seemed to spur her on. She thrust in hard once and held, her whole body trembling in orgasm as she ground against me. But then she resumed, wrapping her hands around my throat and starting to choke me. I didn't resist, not that it would have done me any good, as my face turned red. My look of adoration remained.
It hurt. It hurt so much. But that pain emphasized just how much I belonged to her. I was willingly taking it, embracing it. My cries of pain made her happy. The tears rolling down my cheeks made her happy and at one point, she bent down and licked them off. She continued to fuck and choke me, occasionally letting me gasp for air, and fucking me to several of her own orgasms. I completely gave myself to her, mind and body and the pain lessoned. I did not orgasm myself, but I felt like I should have. My entire body started to tingle at one point and I felt like I might orgasm, but it went away.
She finally thrust one final time in a powerful orgasm, looking like an angel from heaven and then collapsed on top of me.
After she caught her breath she said, "Fuck that was amazing. You've made me so happy today Joe. Would you like to be my full time sub?"
Jake - 1:10pm
"Fuck, listening to your cries of pain has made me hard again. So fucking hot. But we need to take care of this erection. I think...yes. I am going to fuck that tight little hole you have. I know you want me to, its why you tied yourself like this," he said and it terrified me.
But then he started whipping me again. Everywhere. Chest, stomach, asshole, and genitals, and extremely hard.
He yelled, "Beg me to fuck you boy. Fucking beg me and sound like you are desperate for it. I know you want to be a slut. Beg me to fuck you boy..."
The pain and humiliation were unreal. He took great delight in it and seemed content to do it for hours. I held out as long as I could. It was such a stark contrast to how Emma had wanted me to ask her to fuck me, but I knew it would be no less effective. He decided then to concentrate on my balls with the flogger, whipping them over and over while laughing about it.
"All you got to do, slave, is admit what you truly want. I am fucking you regardless, but you need to beg for it. Beg for what you need. Once I fuck you and breed you, you will totally belong to me. I will fucking own you. I know it's your deepest desire, just beg for it, and the whipping will stop and you can complete your transition into my personal slut," he said.
I tried to shake my head 'no'. I tried to hold out and deny his claims as he whipped my poor balls. I didn't want to be fucked by another man. My ass was still sore from what Emma had done, and Jake was larger than the Feeldoe was. But beyond the physical, it was a real fucking cock. I was about to be fucked by a real cock and he was going to cum deep inside me. There would be no recovering from that. No going back after being fucked and bred by another man. I would never recover.
And it was going to happen regardless. I broke.
"Please Ja....Master! Please fuck me! Please....I....I need your cock inside me! Pleeeeeeeease!" I wailed in despair, almost forgetting to call him 'Master' with how emotional I was.
The whipping continued and I cried out desperately before he finally threw the flogger in the general direction of the toy box and climbed onto the bed.
His huge cock was fully hard again. My throat was still sore from being face fucked by it. He grinned down at me as he slowly got into position, his cock inches from my poor asshole. He looked down at his cock and let spittle from his mouth fall onto it, and again, before spreading it over his cock with his hand. It did not appear that Jake cared one bit about using proper lubrication. He seemed to loom over me as the head of his cock touched my hole.
"Beg again slave. Beg me to impale you..." he demanded and slapped my face.
"Pl-please impale me wi-with your c-cock, Master," I said miserably, shaking in fear.
He pushed and the head of his cock suddenly forced its way inside of me and I screamed. But he didn't stop. He slammed all the way inside of me while he laughed at how I screamed. He held there for a moment, looking a little confused.
"There is lube inside of you already!" he exclaimed in realization. "That slid in way too easily. You dirty, dirty slut. You really were hoping that I found and fucked you and prepared yourself for it ahead of time! But fuck, you are tight anyway. I know you fucking love it. I am about to make all of your dreams come true slave."
There were already fresh tears flowing as I felt the pain and humiliation of being completely filled by Jake. By another man's cock. Much of it was from the pain. The same, but different from the Feeldoe. Worse. But there was also the psychological and emotional pain of it. I was so helpless to it. I couldn't work up the nerve to say anything about the lube still inside of me from Emma. Jake would believe what he wanted.
He started to fuck me then and it was the most pain I had ever been in, but I didn't struggle. I was just a hole to be used. I was worthless as a person. What had happened with Emma seemed like a distant pleasant dream of domination and that this was the reality of it. He pumped into me with no regard for me, just fucking me hard, and only concerned with his own pleasure. The smacking sound of his hips slamming into my ass filling the room as his strong body loomed over me. Utterly dominating me in every sense of the word.
I felt myself completely breaking down mentally. He violated my body, but with every thrust, he violated my mind too. My body relaxed as I accepted that I was nothing more than a piece of meat. A sleeve for his cock. It was what I was meant to be.
He noticed me becoming more detached and started to choke me, reaching his strong hands up and cutting off my air. I didn't struggle, but my body started to as it strained to breathe. That appeared to please Jake and as my vision went blurry, he would let me take a few breaths and then cut it off again, toying with me. I prayed that he would go too long and that I would just lose consciousness.
Occasionally when he let go of my throat and I was gasping for air, he would slap me across the face and yell at me to take it like a good bitch. That he was owning me with his 'bitch breaker'. I couldn't deny any of it. I believed him. I was his bitch and forever would be. Who I had been was gone. I was sad for the loss of myself, But replacing it was acceptance. Acceptance of who and what I was now.
The way he was just using and abusing me while I was bound and so helpless to do anything about it started to arouse me. I didn't want it to, but I had learned that what I wanted didn't matter in the slightest. With Jake already cumming once not that long ago, he probably had stamina for days. It at least seemed so as he relentlessly pounded into me. I continued to break on his cock, there was no other choice, and my helplessness to it returned to arouse me more and more.
I moaned.
And how Jake laughed, praising me for finally accepting what a slut I was.
He doubled his efforts then, slamming into me violently, the entire bed shifting with his thrusts, and I continued to moan feeling physical pleasure from being used. "Fuck!" he yelled out and slammed into me one final time. I cried out at the same time as I felt my cock suddenly explode in orgasm, shooting semen across my chest and stomach.
His cock engorged inside of me and I felt it pulsing as he emptied his seed. Claiming my ass and claiming me. Owning me completely. He laughed as he looked down at my cock shooting. Laughed in victory.
He pulled out without fanfare and got off the bed and went to the toy box, pulling out a little box. It was a chastity cage I had bought and tried out, but never wore for very long. Without a word, he roughly manipulated my rapidly softening cock and balls, still sore from the whipping, and stuffed them inside of the cage. He inserted the lock and closed it, locking away my genitals. He took both keys and started to dress.
"Before I go," he said, "tell me what you are and who you belong to...."
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