No binding

“Oh, sissy, you look so cute. I just can’t wait to eat you up. But I feel like there was something that I had to do first '' She stood there contemplating in a state of undress as she looked up and down Jack's naked body with hungry eyes. “Ah, I rember now, mama said something about being careful when I first bind my sissy. So I guess for now you won’t get to taste my creamy cum. And I was so excited that I haven't cleaned my dick since I came here”.

Jack watched nervously as she walked towards her piled up clothing with her member swinging back and forth. He was terrified of this situation and couldn’t talk or move as he stared at her looking around in the heap with wide eyes. She came sauntering back over now holding a long line of condoms as she unwrapped one and placed it in Jack’s frozen hand.

“Now I’m gonna have you put this condom on for me sissy. We gotta get you used to this cause this is gonna be one of your new jobs from now on”

“Yes, Miss Amy,” Jack said in a hesitant voice. Most of his will to break free and get away having melted away with the monstrous cock looming over him. Amy was now directly in front of him with her massive cock inches from his face. He could feel the heat of her dick making his skin crawl as he reached out with the condom. The thick musk and stench of her cock was overflowing onto Jack. The smell filled Jack's lungs and settled in his mouth so that he could almost taste her sweaty filth as his mouth started to water. The stench traveled and got stuck in his head giving him vision of what he believed to be his near future. Visions of him eagerly lapping at the engorged cock and being split by it entering his sissy hole.

Jack gripped on her cock as he slid the condom over it. He felt the layer of greasy cum and sweat that covered her rod and slowly coated his hands in the filth. Finally the cock was wrapped up in the rubber layer and the thick musk was partially blocked. Amy went over to a seat and sat down with her erection still standing upright.

“Now sissy, it's best if you come over here and get to sucking. You’ll want there to be some lube when I enter your tight hole for the first time”.

Jack slunk over and knelt before the massive cock and was staring at it lustfully and in contemplation of how to get started on the monstrosity. Nervously he ran his tongue up its length, feeling its rough texture as a hint of musky scent filled his nose. Amy moaned lightly as she eagerly watched him get to work.

Feeling more ready and confident in his actions Jack moved upward toward the tip of her dick. Opening his mouth wide Jack tries to engulf the cock head with much difficulty. After a few moments he finally fits the tip of her dick in mouth awkwardly as he tries to run his tongue around the edges. Jack kept trying to move and suck on the cock like he had been taught in intro to blowjob class but this thing was way bigger than the dildo he had practiced on. After a while of small moans Amy finally calls out.

“Sorry about this sweety, I wanted to start slow and let you go at your own pace, but unfortunately you’re only teasing my head. I’m gonna need you to work the shaft all nice as well hon”

Jack was shocked when Amy grabbed tightly on his head and with surprising strength **** her massive schlong down his throat. He begins to gag ceaselessly as the monstrous pulsing cock **** its way past his tongue. His feeble attempts at cries are muffled as he watches the dick go deeper and deeper down his throat.

After what seemed like minutes to Jack of his throat stretching to fit the behemoth he finally hits the base. As he feels the heavy swollen testicles against his chin, covered in hair and filled with thick creamy cum. He also starts to taste her sweaty musky shaft down at the base where the condom doesn’t cover. Time seemed to have stopped for him as he adjusted to the large intrusion sheathed in his mouth. After a while his body starts to move unconsciously and he attempts to run his tongue over the cock and taste its juicy flavor.

“Well it looks like you're more used to my size now, but we’ll need to train you some more in the future. Now let's make sure it’s all lubed up”

She continues to grip onto Jack's head as she begins to pull him off of her cock. When his mouth is only filled with the head once more she thrusts and shoves him back down to the base. For the next few minutes she continues to pump Jack back and forth on her cock, using his mouth as an onahole. Eventually she pulls Jack completely off her cock now lathered in his saliva as it drips onto the ground. Jack seems to go a bit limp as he is removed and tries to gasp for non cock filled air.

“Oh that was close, I almost finished in your cute little tummy, but we can’t have that. I need to properly test out that cute little sissy butthole first to really make you my genuine special little sissy. Now Imma need you to get nice and comfy on all fours and point that little sissy hole in my direction cause I don’t think I can hold back and be gentle no more”.

Jack moved stiffly as he crawled into a doggy position before her. His ass held up high and giving her an excellent view of his tight awaiting hole. He tensed up his body as he heard her getting up and approaching him. After mere moments he could feel the heat coming off her on his backside.

SMACK

The sound rang out and Jack shuddered in built up panic as Amy slapped his butt with her throbbing erection.

SMACK SMACK SMACK

Amy continued to slap his ass with her massive cock until Jack was accustomed to it and no longer as tense all over. She then set her cock down on his back as she rubbed his shoulder in a comforting manner. Jack could feel her heavy and hot dick resting on him as it throbbed in waiting.

“Now sissy, don’t be so tense. You’ll come to love this just as much as I will. So just relax this cute little hole of yours and let your mistress explore your body with my eager little cock.”

She said as she had one hand rubbing his shoulder in what was supposed to be a reassuring gesture. While her other hand was running along his ass and feeling up his ass cheeks. She then used that hand and shoved two fingers right into his puckered hole. Despite training his ass with dildos and butt plugs Jack is shocked by the feeling of her cold fingers playing with his hole.

After playing with his asshole a few moments Amy pulls her fingers back and licks them tasting Jack’s inside. While she does this she pulls her cock off of Jack's backside and ready’s the tip at Jack's entrance.

“3,2,1” Amy counted down before shoving her cock the first few inches of Jack’s hole. Despite only being part way inside Jack moans out surprised at the pleasure as his ass is dominated and spread wide open by her girth. He felt like he was being torn in half despite it just entering him yet he also felt like he had somehow been made whole. Amy too was surprised by the heavenly feeling of his ass compared to the toys she normally used.

She let him get used to her thick cock inside of him before she slowly started to thrust forward pushing deeper inside. He felt his hole expanding as he was filled up more and more. His cock twinged and grew even harder as he felt her rub past his prostate. Jack felt on the edge of blowing his own load without even touching his quivering sissy cock.

Eventually Amy bottomed out after fitting her entire 11 inches all the way inside. Jack was surprised that the entire thing could fit inside of him. He felt strange as the girth stretched him open and filled his entire body with a foreign intrusion. His gut was having a constant dull throb as his innards stretched to fit and become used to this state. Through the pain Jack was also getting a sense of fulfillment and even some new sensations. He could feel both the tip poking at the inside of his stomach as well as her balls resting and slapping against his ass.

Amy watched Jack tremble and shake as he grew accustomed to being filled. She waited and sensually rubbed his back until the movement had died down and Jack was now used to her size. She then started to move, pumping and thrusting back and forth inside of him. She started slowly, careful of the small squeaks of pain that he let out despite how erotic she found them. But as his squeals turned into moans she started to pick up the pace and reached a rhythm of humping him.

Jack was surprised at how much he enjoyed her thrusting of her cock. Of course it was natural for a sissy male like him to be a futa fuck toy, but the constant sensation on his prostate had his cock leaking precum at a steady pace. His little sissy dick was in a super state of arousal that he had never experienced before. The musky scent of her sweat, cum, and other fluids was still filling his head and lungs, making him light headed. All of this stimulation was putting Jack in a state of sexual bliss at being used as an onahole. This pleasure increased further when Amy did something he never expected.

“Well, well, sweety, seems you're finally starting to get used to me. That's good, I want this first time to be special for both of us. So here is an extra special reward. Don’t expect it often, but you're a good boy and I want to see what really brings you pleasure” She said as she reached her arms down below and gripped Jack’s cock. While she was methodically thrusting into him from behind, she was also playing with his tiny dick. Kneading it, and pulling on it, she stroked him off in a clumsy fashion as though she was knowledgeable about what she was doing, but unused to this predicament.

She continued to play with Jack until he felt himself erupting in the largest orgasm he had ever experienced. If he wasn’t being held up by her cock he would have slumped in exhaustion from that orgasm. Instead he leaned into her as his cum splattered on the ground and covered her hand.

Curious she slowed her thrusting and brought her cum covered hand up to her face, tasting his jizz.

“Wow, male cum is so watery and thin, and you let out so little. Guess it's no surprise why futa’s are the superior breeders. Now that you’ve had your release it’s my turn”.

Her pace picked up and she began to jack hammer her cock into his body. Her pace was wild and Jack was helpless as she pistoned and pushed into him. This was nothing like the steady pace that had been set before. This was a rough fucking as she used his body to pleasure her cock. After a few moments of this crazy pace he could feel her cock bloating inside of him. He could feel the cum moving up the length of her dick inside of him until the hot liquid gushed out filling the tip of the condom that resided near his stomach.