From Bro to Sissy Sub Pt. 04

They all waited in a line while I made my way through the basement door and down the stairs. We didn't have Magnus and Flora's "Domcave," but the previous owners had made den and there was decent head room, we just put in soundproofing and some hooks and quite few toys. In the middle of the 20' by 20' room we had placed a sturdy crate with some eyebolts for strapping strategically placed. Today bondage would be minimalist.

The binding would be quick and easy for flexibility so they could switch my position as needed. I led Paul and Larry by the hand to the crate. They quickly stripped me down to lacy panties and bra, while I massaged their hardening members through their pants. Meanwhile, Jayden and Big Mike, got undressed as if on fire. They clipped fuzzy cuffs on my ankles and wrists with carabiner clips for flexibility.

They started by clipping my wrists and ankles to each other behind my back and put me on my knees near the crate. Mike and Jayden came over naked holding their big cocks. I went right for Mike's monster, looked at Daddy with puppy eyes, and said, "he is our guest, Daddy."

I had to open my mouth to its utmost to just get the head in my mouth. I got him down as far as the entrance of throat, but no further. I was disappointed; the cuckslut in the video choked on it, but she got more of him down than I could. I contented myself with worshipping the head and licking up and down the shaft. It was a veiny beast with all kinds of bulges on the sides, I was again stimulated thinking about what it would do to my other hole.

Lost in that daydream, I played with the big beast; Jayden nudged our guest out of the way to push himself into me. I never thought I'd be going from a bigger dick to Jayden's, with some effort, I get him down my throat, and was thrilled to have him. Larry and Paul now came over too and were jostling for their own taste. I gave myself over completely and let in whoever proffered their cock. It felt so good to be fought over and pulled around from cock to cock.

Jayden suddenly pulled me up by my new choke collar and positioned me over the crate roughly, on my belly, clipped my wrists and the collar on one side of the crate and my ankles to the other. The collar was on a lead, giving me about of foot of leeway. I was strapped in and available on both ends. Larry set up behind me and began massaging my hole with his fat fingers. I could feel him worked lube into me, as Jayden and Paul fought over my mouth.

Big Mike went over to the tool cabinet where the toys were stored. He brought back a small heart-shaped crop. He struck the top of my buttocks with it, while Larry pushed a finger into me. Jayden and Paul were trying to get both their cocks in my mouth at the same time, without success. I opened wide as I could, but they were two too big. I couldn't even get heads in.

They placed themselves side-by-side and I went from one to the other with my limited reach. Paul pouched my cheek out with his cock and Big Mike smack it with the crop. It really stung, and they did it a few more times. Larry was up to three fingers in my ass, which took some of the sting out of being cropped in the face with a cock in my mouth.

Larry fondled my pre-cum leaking clitty. I came hard internally, but the most I ever squirted was a dribble of clear fluid with no relation to the intensity of my orgasms, even in the throes of intense ecstasy, I would produce the same teeny dribble of fluid bearing no resemblance to real man sperm. My limp little clitty was about half its original size and required no cage.

I felt Larry slip into my ass and cause more pressure than normal. I was very glad for the three days Daddy kept me from filling my hole. I was tighter and could experience Larry's straight meaty cock, as it slipped smoothly into me. He was about as long as Jay, but less girthy. He was stabbing into me with that cock and grunting and shouting in his baritone voice. In appreciation, I moaned loudly around Paul's big cock in mouth.

"You like that in your nasty fucking cunt, whore?!" Larry shouted at me.

"Mmmm, mmmmghh!" I moaned and nodded my head for more.

He didn't settle into a rhythm, but kept pulling all the way out and then stabbing back in, holding it in and repeating. I could feel his balls slapping against my limp dangling clitty. It no longer got hard because of the hormones, but the feeling of his big man balls bumping up against my teeny package was still devilishly arousing to me.

I was already headed for another orgasm, but wanted to wait. As Paul and Jayden changed places. I screamed out for help from Big Mike. I was moaning and groaning as I caught my breath before Daddy took over my throat. Mike saw what he had to do. Larry moved up and continued fucking from a higher angle; Mike cropped my clitty hard until my arousal slowed.

But then he made things worse, fondling my clit and squeezing a finger between Larry and the rim of my ass. He put my whole package in his mouth while wriggling his finger along with Larry's cock. I was on the verge, when he stopped and cropped my clitty again. This was torture. I wanted to wait, but the stimulation was too much. He repeated the process a few more times.

But by then, I was too excited and the cropping didn't stop it anymore; I came again as he was striking me and had two fingers in along Larry's cock. I couldn't even beg Daddy, like I wanted because it just suddenly came upon me. Larry—who was being stimulated as much as I was by Big Mike's fingers exploring my hole—was about to be the first one to come inside me.

Not that what I wanted mattered, but I was torn between wanting him to pull out and come down my throat and just filling my guts with his cum. He chose the latter, and I felt his cream oozing out of me as Mike pulled his fingers out with Larry balls-deep in me. He brought his slimy fingers, dispossessed Jayden of my mouth, stuck the two cum-covered fingers in my mouth. I sucked on them delighted to taste Larry's spunk, while feeling him still deep in my ass.

Daddy thought it was a good time to change positions and unclipped and reclipped me, so that I was now on my back on the crate, my ankles clipped behind my head, and my ends hanging off either side. Paul and Jayden moved to my ass and Big Mike took my head. I tried again to swallow that beast, with a bit more success from this angle and my cum-lubed throat.

The fat head of his cock ease down my throat more, but took away all my air, so that I was near passing out when he took me deep. I was happy to have made progress in getting the monster down my throat, and could see why the gangbang cuckoldress choked so much on the video.

Daddy let Paul have access to my ass first, but they were alternated, so each one got five or six thrusts and the other would quickly pop in. Except for the change in size and Daddy's wonderful curvy cock, it might have felt like continuous fucking. But just the thought of being passed back and forth between two large cocks was making be very happy.

As I continued to struggle to get Big Mike's cock down my throat and alternately lick his ball and shaft like a desperate slut. He was slapping at my rudimentary titties and engorged nipples. I enjoyed the fact that I had something to offer now. After a hit, he would knead my little puffy titlets and pinch my engorged nipples. I was so excited that it was like electricity flowing through me. I had to concentrate on other things to keep from nonstop coming.

But I was on fire, I kept being brought back to the present, where I was experiencing such pleasures that pushed my thoughts right back to ecstasy. Daddy's twisted cock was giving my rectum a delicious ride, Paul's straight fat cock in his turns was hitting my p-spot just right, and I had this elephant cock choking me up front, and eager for what it would do to my other hole.

They had arranged themselves in size-place order, saving the behemoth for last, and I still hoped to get two in my ass at the same time, as in the video. These thoughts put me over the edge, again. This time I didn't even bother about begging to come. I just shuddered and moaned as another powerful orgasm took hold and my clitty spurted its weak fluid.

They all had to know I was coming hard as my legs were quaking against the restraints and my little ass shivering against Daddy's cock, then inside my hole. He pulled out and moved toward Larry, who was lounging with a drink in hand watching the show. Paul followed and Big Mike squeezed my titlets, pinched and twisted my nipples, as he moved to my other end.

"So... you think you ready for my big cock, slut?!"

I was still sputtering from the massive orgasm they had just given me, gasping after that colossal cock evacuate my mouth. I couldn't wait to feel it opening my hole further than it had ever been. I could feel the emptiness of my gaping hole having lost its recent occupants. In response, I pushed my ass up toward him by tensing my legs against the ankle clips.

"Oh, Yes! Please, Sir, I want your giant beast all the way in me. And... Sir?"

"Yes?"

"Don't be gentle, pleeease! Just fuck me hard! I want to feel it tear into me."

He fondled my little package with his thumb as he pushed three of his fingers in my hole and them pinched them together, like he holding a bowling ball. The pressure on my shrunken testes was intense, as he lifted my ass slightly off the crate with this bowling ball hold. I tried to lift myself further to ease the discomfort, but he pulled me back down.

He kept the position, but eased off on the thumb and began to twirl his fingers inside me. I moaned to let him know how much I liked it. He put the last finger in and twisted his hand around opening me up further. He then cleared his throat and spat a big wad into my hole and worked it in. Then, he brought the beast into position and placed on my clitty. I could feel the weight of that massive thing resting on my insignificant little clitty.

I was trying to look down to see it; he helped me by pulling my hair until my collar choked me, but I could see down my belly to were that enormous cock lay from my taint to my belly button. That! was going to be in me. It would tear up my insides and likely rend asshole, but I couldn't wait to have it, to feel the burn as he stretched my anus and pounded on my prostate.

My hole was nice and open and well-lubricated from lube, spit and cum, but nothing could really prepare it for what was about to happen. That massive log would destroy my little hole. And... it would open me up, so I could realize yet another fantasy of having two cocks in there at once. He was teasing me, just rubbing the head against my entrance without any real forward pressure. I was pleading, begging, pushing my ass up to make it penetrate me.

"Oh, you really fucking want it! You sure? It's going to hurt; and I won't take it easy on you?"

"Please, Sir. I don't care if it hurts! Hurt me with that fat fucking cock, please, Big Mike, Sir!!"

He nudged just the head forward, and I felt the walls of my asshole resist his entrance. I wished to just open up to him, but it was still tight, even after being fucked by three guys. I opened my ass cheeks with my hands to give him the widest berth possible.

He pushed in some more. The insistence of huge hard cock against my anal wall is, to me, one of the most delicious parts of getting ass-fucked. It was a microcosm of what was happening between Big Mike and me. This huge he-man easily dominated sissy little me; and his big forceful cock pushing, my pliant flesh would resist futilely, but be easily overcome by his power, just as I was. I waited expectantly for the moment when he would rip into me.

He was in me in a flash of pain, my resistance quickly overcome; he was all the way in, and stilled deep inside me. The burning sensation went through me, from inside my belly to the tip of my dangling toes. I knew it was pain, but it didn't quite feel like pain. It felt wonderful, luxurious. It was tight for him in there, and I could feel him pulsing as if a monster was breathing deep inside me.

Holding himself full in me, he reminded me to breath; when I did, the feelings flooded in. I felt the pain, but then the pleasure as he slowly withdrew. He moved slowly and deliberately inside me. I was ridiculously shouting for him to do it harder and deeper, but luckily for me he knew better. He fucked me at a moderate pace and wasn't always hitting bottom.

"Oooh, oh, aaaah, oooh, fuuck, fuck. Fuck! Fuck my fucking ass, Big Mike, Sir. Fuck me hard! I'm ready, please."

He pulled out of me and unclipped my ankles and neck. He dragged me off the crate by the collar and positioned me so I was prone on my back about two feet from the crate. He had me put my legs up as if was going to do leg raises, grabbed my ankles and clipped them to the side of the crate so my legs were wide apart and my ass was up in the air. I was now looking up at him, as he reintroduced his gargantuan penis into my gaping hole.

Watching it go in from this angle, started me on another build up to orgasm. His giant cock was uncircumcised and had a bullet shape to the head, but the very pointy end had such and obtuse angle that the rest of the head was radically wider. It was just so big it seemed to take forever to get all the way inside me. I was watching voyeuristically, as if it happened to someone else.

I again began to beg for harder deeper fucking with the beast. I couldn't even believe myself as I asked to be pummeled with it. He was finally ready to really give it to me and began to pound me into the ground with that monster. As soon as he started, I was coming and screaming about it, for all to know. And... I kept coming all the while he built up to his massive orgasm.

He filled my hole with cum, the huge beast was prolific; I watched it burble out of my ass and begin dripping onto my face, where I desperately tried to taste it. We both just kept coming as more and more oozed out of me. He pulled out and used his cock to scoop his cum out of me and drip on my face. I was happy to catch as much as I could. I'm such a nasty cumslut!

When he was done ladling cum out of my ass with his big cock. He joined the other men, who had all been watching from our little bar. Again, I was left tied up, my asshole destroyed, still shuddering and quivering from coming so hard and having the biggest cock ever give me a colonoscopy. I loved and hated this feeling. I felt so used, which I enjoyed, but I was lonely too.

I lay there in restraints, with my legs over my head staring at my dripping clitty and the spunk on my belly. I felt so dirty, so slutty. I felt like all these recent fantasies were coming true, and I was about to have another. My hole felt so sore, but suddenly so empty and desolate. I wanted them in me, but they were drinking and hooting. Talking about how Big Mike had thoroughly owned my pussy. Yes! he had, but I hoped they would come and play with it some more.

They finally came back. Big Mike was a one and done guy—I suppose it takes a lot of energy to get thing like that up—so he stayed in the background. Daddy unclipped my ankles and stood me up on unstable legs, while Paul sat on the crate. Larry and Daddy stood to either and pointed to spot on the floor between them. I got on my knees between them, knowing what I was to do.

I blew them going from cock to cock round and round until they were hard. Daddy and Larry lifted be bodily and placed me on Paul's cock, as he laid back. His cock slithered in, and I was happy to note that despite the huge beast I still got goosebumps as his cock happily filled my hole. I had to contain myself, being unbound, as I began to bounce on his cock, I felt so free. But Paul pulled me down by the collar. He slapped my face to get me to settle and then kissed me hard squeezing the collar with his big hands choking me.

His tongue explored my mouth and throat and his cock deep inside, I felt what must have been Larry fingering my ass. I was so close to getting what I most wanted, soon that finger would be replaced by a cock; I would be skewered by two cocks at once. I focused on kissing Paul, while getting reamed by a cock and two fingers. Daddy pulled back my collar and put his cock in my mouth. Paul didn't mind; he and I tongued Daddy's big curly cock as it hardened.

Meanwhile behind me, Larry had stretched out my hole to the point where he was about to try to replace his fingers with his cock. It was about to happen. I wanted to concentrate on it, but the cock and lips were distracting, suddenly I knew it wasn't just fingers in there. I had two cocks fucking my ass just like the gangbang cuckslut in the video.

I don't know if my ass was more open for Big Mike or these two cocks, but this was even more exciting. They wouldn't necessarily go at the same time. So, one could be going in when the other was pulling out or both together. It was pure heaven. I loved everything about it from the physical feeling of two big cocks "owning" me, to the pleasure I could tell I was bringing them and how insignificant and vulnerable I felt and at the same time powerful and sensual.

Paul moaned into my mouth and Jayden's cock, and I felt him juddering under me. Oh, fuck, he was going to come. I might have been closer on the same road, but I was exhausted from all the coming, but it got me excited all over again. I was going to make him come with another cock in there with him. He pushed in hard one last time, but Larry kept fucking fast and hard from behind. The feeling of Paul coming, while still being pummeled by Larry was incredible.

I could feel as Paul's meaty dick spasm inside me and how slippery Larry's path became as he continued his fucking. Paul was done, and Larry pulled me off, his cock buried in my ass. He held me up, legs in the air, and Daddy came over, propped my legs on his shoulder and pushed in alongside Larry. It was tight; tighter than Big Mike, but my ass gave in and let the intruders in.

I couldn't believe it. I had not even dreamed of this. I thought it impossible. It was so tight though and they were both about ready to finish, so they went wild fucking up into me, without mercy and I was ready to come again.

"Daddy, please...?"

"Just wait for me, sissy. I'm coming too."

He fucked me furiously hard as Larry held his position. Soon, he was shouting and grunting he was coming, and I came too. Daddy pulled away leaving me impaled on Larry's cock. Larry couldn't hold me up any more so he lay back on the crate. He put his cock to my mouth, and I let him finish there as he came down my throat, while I worshipped his cock still shuddering through the last monster orgasm.

He collapsed on top of me, and we lay there a moment, until we all got up and cleaned up. I could not be happier with my first gangbang. It was better than I imagined. We had one last drink; I kissed the men goodbye and thanked them for showing me such a wonderful time. After they left Jayden and I took a nap, a bit later, I woke up still aroused from the festivities, I confessed I had come five times without permission and made him punish and fuck me one more time. I was so raw; it was pure gluttony. I fell asleep exhausted, sore, and contented.

It has been two years since. Jayden and I have a wonderful relationship. We decided to have an open-relationship. Which has meant much more freedom for Jayden than me. But I'm not complaining. I am perfectly happy with just one man fucking me almost nightly. If he does one of his movies or brings home a man or two, or three, to join us, I'm okay with that.

He's my Dom in the bedroom, but out in the world, I am much more in charge. I went ahead with gender affirming treatments. I had the facial surgeries and continued hormone therapy. I developed puffy, but significant breasts; I saw no reason for implants and neither did Jay, who is my very happy with my perky little titties. I had the orchie surgery, to remove my pea-sized testicles. I didn't have the vagina surgery or cut off my clitty. Jayden likes it dangling there reminding him I'm a sissy.