It's Either Break Up Or Make Up

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Her fist was now buried deep inside my asshole, her fore arm surging pass my sphincter, rubbing harshly over the sensitive tissue of my asshole. She felt me squirming beneath her, her fist twisted and turning deep inside she really wanted me to feel the complete control she had over my body. My ass was now stretched wide accepting her fist forcing its way into my asshole.

"Please, no more, it hurts," my tear filled eyes pleading with her as she watched my asshole as it stretched open wider, my sphincter clutched tightly on her fist as they gripped it like a giant rubber band stretched to its limit, ready to snap from the strain.

"Yes, Ricky, you are so tight, but we both know you can take my fist even if it hurts a little much like when a woman is raped and not lubricated naturally for sex. There is so much more, I wanted to do to you before you die in shame.

'The Terminator', my new dildo with metal bumps all over the shaft the head awaits the opportunity to rip apart your asshole as I use it to fuck you to death. Laughing she fist fucked my asshole opening her hand and scratching the walls of my asshole with her finger nails drawing blood. She buried her fist as I buck beneath her, as she enthusiastically punished my asshole. Shoving, clawing the insides shredding the silky walls of the canal. I wanted to fight her every inch of the way but I couldn't, she controlled my body with a third subservient masochistic personality that she awoke a few weeks ago to both the surprise of sissy Ricky and I. Finally she had her fist pounded deep inside me; the opening of my ass was stretched wide and bleeding, the pink color of the inner canal now turning raw and red as it was forced to accommodate the thickness of her fist. She twisted her fist inside me, then spreading her fingers apart again while deep inside me, all to hear me scream and beg in pain. She tortured my ass for yet another night forcing me to accommodate her fist.

"It hurts too much, P-Pleaseeee take it out," I cried pitifully!

To my surprise and relief she withdrew her fist and forearm and I saw they were covered with baby oil and spots of blood. She sat up so she could apply Ben Gay extra strength on her hand, wrist and fore arm. Once satisfied a wicked smile came across her face and she plunged her fist back into my tortured ass.

My pleas fell on deaf ears, 'The Terminator', was going to rip apart my body, not caring about anything except her desire to fuck my pulsating asshole. With the coating of Ben Gay extra strength may ass was burning even more. She felt my body slump down as she pulled her fist out of my asshole with a loud pop, my anguish and embarrassment overcoming my senses. My relief was short-lived, her strap-on returned to where her fist had been, ready to replace her fist. I looked to the side in a mirror and I shivered as the hot head of her strap-on was pushed against my sore swollen asshole, despite being opened by her fisting me.

Tyra poured more baby oil and burning liniment on my ass, making sure it covered 'The Terminator', pushed against my swollen asshole. Although I had been speared by her fist, it was nothing compared to the size of the crown of her strap-on coated heavily with Ben Gay. She pushed her hands down to the side of my hips, grabbing me tightly, controlling the movements of my hips; ready to show me how she was going to fuck me with her strap-on. She slowly crawled up my back with her body, wanting to be able to fuck me as deep as possible, wanting me to feel the mastery of her strap-on in my asshole.

"No, don't, please don't it is too big," my last attempt at persuading her causing 'The Terminator', to plunge. "GGGGGGRRRHHHH," I cried as she began to push down on my hips while her hands held my hips up, never letting me escape the dildo that was forcing its way into my ass.

"AAAAAHHH, God, take it out, don't," feeling her strap-on slowly stretching back the skin of my asshole, forcing it to tear and bleed as her head, began to push inside my sphincter clenching the strap-on. Another shove and half of the head was now inside, my ripped sphincter trying to push it out, 'The Terminator', slowly penetrating my asshole, aided by the liberal amount of baby oil.

She could not hold out any longer, her hips shot forward sharply, forcing the head of her dildo to push inside my pulsating asshole, my sphincter grabbed it just under the ring, squeezing it like a pair of hands. I screamed in pain from the thrill her strap-on gave me, as I bucked underneath her strong hands the only thing that kept me from pushing her off. My mind was saying no but my body was reacting to being fucked. I was like a wild stallion, intent on throwing her off, her grip on my hips allowing her to tame the beast within me. "Relax, Ricky, it's in, time to take Ricky for a ride," feeling my body reacting to the intruder in me, my insides clenching on it, pushing out trying to expel it.

"Don't move, it hurts" I screamed. The pain of withdrawal was the same as the pain of entry; I was willing to allow its presence to prevent any further pain.

I involuntarily began to move my hips slowly from side to side; my asshole massaged 'The Terminator', as it moved around inside my clutching asshole. "Relax, Ricky, "She whispered into my ear, "get used to 'The Terminator', and enjoy the pain inside your asshole." She was happy; I was feminized helpless, on my knees with my ass spread before her, with her dick held tightly by my asshole as she fucked me. I was hers and had to do as she wanted.

"She pushed down on my back, and began to slowly sink further into my body. She lurched forward, then pulled back, then forward again. Each time she was forcing my asshole to take more of her dick. She entered my rectum the hot confines sucking her deeper into my body. My clenching asshole forced her to use greater force each time. She began to rapidly fuck me, using short, hard thrusts into my asshole. She would enter me a ½ inch deeper, pull out and then plunge in again, reaching deeper into my sore ass.

I was screaming in pain as she fucked me. It was music to her ears. Each scream of pain brought about another rapid thrust into my asshole, her strap-on tearing into my body, plundering my asshole. My asshole was only hers and she wanted me to remember these nights since the first night that her strap-on took my ass. Her hands held my hips tightly, forcing them right to left, as she pumped her dick deeper into my asshole. She had over half of it in me now; my hole looking like it would tear and bleed once more if it stretched any further. She did not care, that her dick was intent on fucking me as deep as possible.

For the most part I was no longer controlled my body, I was a spectator.

"OOOOWWWW, t-take it out, it is to b-big," I screamed in pain, my hands grabbing the headboard tightly, my face frowned in pain as she tore into my ass with 'The Terminator',.

"More, Ricky, you have to take more, I only have ¾ of 'The Terminator', inside you and you are already bleeding pints. That's over 10 inches of dick that is being devoured by you greedy ass. But I intend for you to take more, you are going to take every damn inch!" she said.

With that she drove forward again, this time wanting to bury all of her dick in me. She shoved hard down on my hips, pulling up on my hips as all 14.5 inches of her ass ripping strap-on slowly slid along my tight clinching asshole. She felt my body jerking in pain, as my colon was forced to straighten out to accept her dick.

My screams, "Please stop, P-pleaseeee stop you are killing me, somebody help me please!" reverberated through out the house, it was a bad thing the house was isolated no one would hear my cries. Her Strap-on felt like a red hot iron bar was being forced up my ass. She had achieved her goal of burying it to the hilt. She stayed still, barely moving as my body wiggled like a bug on a pin.

I did not know how long she could remain motionless, knowing her desire was to make my ass burn as she fucked me.

Her hand reached over and pulled the wet hair from my face, my unmanly tears ran down my face in a continuous stream now. "You have my entire dick in you now, Ricky, how does it feel?"

She then moved stirring her strap-on inside of me she wanted me to know that she completely in controlled my life. Again she moved her dick, causing me jump in pain when she did.

"Take it out, finish with me quickly, it hurt so much, OOOWW," I cried, her strap-on inside me jolting my body in pain. No I am going to take my time because I know with each stroke the tissue inside your ass is being ripped away which is why you bleeding. You are going to die being fucked, the papers will love the story of the macho womanizing soul singer who dies with silicone breasts glued to your body, and on your feet in 6 inch clear heeled fuck me pumps and 'The Terminator', all the way up your ass. The tabloids will pay millions for the photo I am going to take before calling the police.

"Soon, but first I want to make you cum, take strap-on deep in your asshole." I moaned in pain as she bent over my body, one hand reaching under to grab my dick with her hand, her fingers stroking my dick.

"It may hurt to have my strap-on in your asshole, but your dick is wet with pre cum." Her other hand reached one of my dangling silicone breasts and began to pull the nipple hard, twisting and turning the hard nub, feeling my body squirming beneath her. She began to abuse my body with her hands, stroking my dick and nipple with her fingers. She gripped my dick between her fingers, twisting and turning me in rhythm with the one on my breast. I arched my body up, forcing her dick in deeper into my asshole, the pain forcing me to pull back which allowed her dick to slip from my ass.

Her hips became a blur as she fucked me harder and harder. She knew that I was in extreme pain, my face contorted, sobbing loudly, but my asshole continued to fuck her strap-on in and out. It pulled back until only my sphincter trapped the head, then I uncontrollably pushed my hips back, forcing my asshole to suck 'The Terminator', back into the depths despite the pain.

Her fingers stroked my dick and it became stiffer, rubbing over the swollen head, feeling me surrendering to her, my hips rotating as she pushed her dick up my asshole. "Tighten this ass bitch as I pull it out of your ass." She slapped my buttocks, and I could feel my asshole clinch on her strap-on. "Like that, do that again, Ricky," her hand slapped me again.

"Ok, please just don't hit me again," I clinched her strap-on tickling her clit as my well fucked asshole as she dragged it from my body.

"You have my permission to cum for me now, Ricky? I am not going to stop fucking you until you cum again. I can go all day, can you?"

"Yes, make me cum, make the pain stop, please," I shouted in pain, my fingers stroking my dick furiously.

Tyra felt my weakening body shuddering, recognizing the signs that my second orgasm was near. Gurgling sounds came from my mouth, unrecognizable noises from the combination of pain and pleasure that I was enduring. My body clenched onto Tyra's strap-on, my orgasm rippling through my body and my asshole.

"You have my permission to cum for me now before you die," she said as she thrusted 'The Terminator', deep inside my ass. I felt my body jerk in pain as the dildo tore up my asshole. I began to spurt my hot salty sperm all over the bed spread. "GGGGODDD, it h-hurts," I said my body unable to contain all of the conflicting emotions bubbling within me. It felt my cum every where as the bruised tissue of my asshole aching from the pounding Tyra had inflicted me for over a week. Repeatedly I spewed copious amounts of cum as I experienced multiple orgasms as I was nearing death.

The multiple orgasms, and the pain were too much and I fainted from the heavy strap-on resting on my back and the blood gushing out of my ass.

My ass was sore beyond belief, Tyra had fucked me for over two weeks, I thought she would never stop I looked forward to my house work despite the heels because I could no longer sit down. Tyra was sitting in the living room looking at me, a big grin on her face.

"Last night was great, it has been months that we have had sex every night straight," she said. "You looked so helpless as I fucked you. I am getting good at pounding your ass, aren't I?"

"Please Tyra, please stop you are killing me my ass is burning it is like raw hamburger you are going to do permanent damage.

"

"Precisely," she said smiling slightly.

The next night after my bubble bath I reported to her in the cherry picking room as required.

"I think I'm done, you wanted to know when I was finished cleaning," I said fearful of what she had planned."

"How does your ass feel?" she asked sarcastically.

"My ass is a really sore," I answered fearing the worst, my ass was so sore I could barely walk.

"That's too bad," Tyra said as she moved closer to me, "I am looking forward to fucking you tonight. Assume your position on the floor and lube your ass for me with my special oil."

I opened my eyes fully and looked down my legs trembling in my shimmery stockings, 6 ½ inch heels. My ass was sore from the abuse it had received. I felt dirty and used, slutty, humiliated, and became very nervous realizing that she was going to fuck me to death.

My anal tissue was ripped away and several capillaries and a vein ruptured and the trickle of blood increased to a constant flow out of my ass. My head started to spin, I could feel myself getting weaker my tears welled in my eyes as she placed the head of 'The Terminator', at the tip of my burning ass hole she was really going to kill me

"AAAAAhhhhhhhhhhhhhhhaaaaaaaaaaaaaaaa, Nooooooooooooooooo, Pleaseeeeeeeee, Nooooooooooooooooo, I woke up crying screaming like a baby, my body soaking in sweat, "No please you are going to kill me. Please I am sorry I don't want to die, please Tyra have mercy I screamed to the top of my lungs with tears gushing from my eyes as my body shook. I balled my self up and just cried like a baby in my empty bedroom.

The light came on and Tyra entered my bedroom.

"What's wrong Ricky why are you're crying, are you in pain? She asked.

"Your going to kill me I know it! I said I am sorry I have done everything you asked to try and make it up to you but you are intent of fucking me every night until my ass bleeds out and I die."

"No Ricky you are having a night mare, I only wanted to punished you for what you put me through, but I never wanted to hurt you," she said sitting down in the bed and pulling my trembling body into her comforting arms.

"It's all right Ricky, it's all right I would never kill you, I didn't know you were in pain."

"But I told you a week ago that my ass was sore and I was waking up in a pool of blood each morning," I whimpered.

"There, there it was a nightmare, It has only been a three days and I have only fucked you one time, try and remember, you are safe Ricky, I will not harm you. I love you, I don't love your ways."

"Take my hand and come with me," she said.

"Where are we going?"

"To my bedroom," she said.

"No, no you said."

"Hush now, I said to my bed room not the cherry picking room I told you that I would protect you, come with me I want you to sleep in my bed so you can feel safe. If you prefer you can stay here in you room in the dark. I got the impression you didn't need to be alone tonight.

I reached up and took her hand and followed her into the master bedroom where we slipped under the covers. "You never need to be afraid of me, I have forgiven you. I will always take care of you, even when there is another man in my life," she said holding me until I fell asleep in her arms for the last time.

The nightmares stopped after a few nights had passed and I was able to sleep alone in my bed again. In these weeks she has fucked me with Goliath and I got over my fear that she was going to kill me. The strange thing is that I focused so much on her not trying to fuck me to death that I didn't realize that I was moving my ass around and pushing back fucking myself as she plowed me. I am sure she noticed because she use to just stop thrusting when her strap-on was in my ass and before long I would be moving back and forth on her dick.

Chapter 6 CHASTITY:

The next week:

"Ricky do you know what this is I searched for months until I found it and I ordered it a few weeks ago?" she asked.

"No I have no idea," staring at the strange stainless steel device with apprehension.

"But you will know it well it is your

Houdini x-22 Chastity Device which is designed to prevent your erections. With this chastity device I can lock your dick into place and know you have no choice but to behave. It is 100% stainless steel and has a firm, but comfortable grip on your dick since you won't have any use for it now. I am putting you in this chastity belt so that you can't get to your dick and steal a little pleasure.

"I am going to enjoy watching you squirm in pain when ever you try to obtain a full erection. This Houdini x-22 Chastity Device is made from a single steel handcuff, welded to a steel tube. The cuff double-locks for extra security the cuff locks around your dick and balls. The inside diameter of the tube is 1 3/8". The tube length is just 3.5" in length, so when that one eyed monster 10 inch tries to spring into action you are going to be in for a lot of pain. Since you haven't cum for nearly a year you should be in a lot of agony.

"But why are you doing this you already made it so I can't cum with out your permission. I won't wear..."

I stopped in mid sentence as I lost control of my body. When she said a trigger word took 'Sissy rickie' took control of my body and picked up the chastity device that Tyra was holding. My 10 inch dick my pride and joy was being imprisoned in a cold stainless steel artificial cage, growing smaller as I was consumed by fear.

'Sissy rickie' adjusted the Houdini x-22 Chastity Device as my body stood naked in front of Tyra, put the lock in position and pushed it shut. I handed the key over to Tyra and she casually put it in the back pocket of her jeans. The device was made in such a way that I could piss but that was it. And I had to sit down to do it! 'Sissy rickie' managed to lock the small padlock through the hasp around my flaccid dick and pulled my panties up.

I was led from the room, tittering on perilously high heels, taking tiny mincing steps because of the leather ankle cuffs, my tightly pantied ass wiggling with a helpless, feminine desperation. I started to realize just how difficult it was to walk in the heels with out Sissy Ricky's help much less with and hobble chains, a leather harness that held a fat butt plug rammed so deeply into my tender ass foreshadowing, my future as a sissy.

CHAPTER 7- BUBBLING TO THE SURFACE:

A few nights and a several fuckings later I didn't know what I was going to blurt out next or how I was going to get out of this. When Tyra gets me this horny I will do anything she asks I think. Now I'm not so sure she reached down and pulled out a bottle of lube from the night stand and started to coat her finger never taking her eyes off me.

"So what is it going to be sissies?" she teased.

I swear I didn't say anything but I heard my voice say "fuck my ass."

She smiled and started to laugh ever so gently. "I knew one of you would answer me. But I'm not so sure you both really mean it.

"You'll need to do a better job of convincing me you really want your ass fucked by my big strap-on dick."

I had lost control of my body as I was witnessing what was going on and hearing what 'Sissy rickie' was making me say and how Tyra was repeating it I had lost all control. My voice began to beg in a weak, breathless voice "please fuck me. Please fuck my ass. I want your dick deep in my ass and please let me cum. Let me explode with stream after stream of hot sticky cum it has been so long since I came."

1...34567...14