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The Bet

Category: Anal Sex, BDMS
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I took the bet certain that I would win. The stakes of the bet – the winner gets sex the way they want it. I knew he wanted it, but I didn’t know how he wanted it. I was so sure that I would win. If I won, I’d put on a two headed dildo and fuck him up the ass; all the while taunting him. At the centre of the dildo was a giant ball sack. The harness I wore held the dildo by the ball sack so that half the dildo was up my cunt and the other half stretched forward like a giant erect cock. The way I wanted it was me as the dominant and him my submissive.

I would stroke his giant cock with both hands as I fucked him up the ass from behind. He hasn’t had his dick inside me in months. Which is not to say that we haven’t had sex. We have had a lot – unfortunately for him, he always lost the bets. I would fuck him in the ass with my strap on dildo and I’d give him a hand job until just before he came and then I’d let him finish it himself as I power fucked him in the ass. I would pull back until just the tip of the dildo was in him and as I held his hips I’d ram it hard into him. I would ride him as hard as I could and the louder he grunted, the better I liked it. I would fuck him until he couldn’t take any more and pleaded with me to stop. The harder I rode him the more the dildo in my cunt stimulated me causing me to experience powerful orgasms. I would take particular satisfaction in the fact that often times the following day I could see him walking funny.

“Does the fag boy like it up the ass?”, I would gasp while I thrust into his ass and writhed in ecstasy. I would taunt him by telling him that he should seek out gay men to fuck his ass. He would grunt through clenched teeth as he struggled to take my unyielding dildo up his ass. As I came, I would be squealing and writhing as I kept thrusting deep in his ass.

The fact of the matter was that he won the bet and now he called the shots. For all of the times that I had won bets and ass fucked him – he was now going to pay me back in spades. He had instructed me to thoroughly lubricate all of my orifices. I paid particular attention to my asshole as I was certain that he would use his huge cock to pay special attention to my ass. His cock was about twice the thickness of my dildo and longer by half. I’d fuck him with an 6″ dildo, but he was going to fuck me with a 8″ cock. The thought of being ass fucked with a cock as huge as his filled me with fear – huge not because of the length, but because of the thickness. I’ve never been ass fucked before and I didn’t know if it would cause discomfort or pain. If it was painful, could I endure it with my pride intact, or would he break me and ass fuck me until I begged for mercy.

“Assume the position”, he commanded.

I took a low back chair and bent over the chair back. My ankles were tied to the rear legs of the chair and my wrists to the arms. I was so sure that I would win the bet that I had agreed to let him spank my bare ass 20 times if I lost. He picked up a thin leather strap and began to punish me. The first lash landed heavily across my ass cheeks. Although it hurt, I didn’t let on that it hurt – I was determined to keep my pride.

“I am going to make you scream”, he told me.

“No way”, I said in the most convincing nonchalant voice that I could muster.

After five heavy swats, I’d had enough and I couldn’t stay silent. Each stroke caused me to grunt through clenched teeth. By number ten I was crying out from the painful blows. By number 15 I was screaming and begging and there was five more to go. The remaining five made me squeal like a stuck pig. He left me tied up and sobbing as he caressed my burning ass.

“I told you that I’d make you scream.”

I now knew that one way or another he was going to break me. When he finally untied me and led me to the bedroom my ass hurt so much that I was walking funny.

“Assume a rear entry position,” he commanded.

I crawled to the centre of the bed and stopped. Legs spread wide, arms straight and head high in defiance.

“Legs together,” he commanded. “On your elbows and bring your ass down.”

The leather strap landed heavily on my ass with a loud crack. I squealed and quickly assumed his desired position. I had to submit – I just couldn’t take anymore whippings.

“Please don’t whip me any more. I’m submitting to you,” I begged.

He stood in front of me stroking his very thick, 8″ long cock with both hands slathering it with lubricant. I knew that he would soon be buried up my ass and I would be struggling to take that enormous man meat up my asshole. If my much smaller, yet big nonetheless, dildo caused him to struggle, I could only imagine how I would feel with his huge cock reaming me out. I assumed a more submissive position and he moved around behind me. I felt a twinge of fear as I pictured that huge cock penetrating my tight, virginal, star shaped asshole. Its one thing to be ass fucked for the first time, but to be ass fucked for the first time with a huge cock would be a struggle. His cock was bigger than huge and definitely not the size of cock with which to be ass fucked let alone take my anal virginity. He was at least twice the thickness of my strap on dildo and half again as long. He was hung like a fucking horse and my asshole was going to be stretched around his huge cock very soon. After he was finished with me, my asshole would not be same. My body stiffened when I finally felt the cock head press against my asshole.

“Please don’t. You’re too big.” I mumbled under my breath.

“I know, but its pay back time. I’m going to make you into an anal blonde so that anytime I want it, you will surrender your ass to me.”

I knew he meant it. He was going to really work me over. With gentle jabs, he slowly worked his way into my ass. Slowly, ever so slowly the giant mushroom head stretched me open. Despite the fear of being sodomised with such a massive cock, I was getting so turned on by his dominance. The cock head was so big that I started whimpering with each forward thrust. I was getting stretched to the max. Finally when I felt that I couldn’t take any more, the cock head popped into my asshole. He was fucking huge – horse cock huge – and I was really feeling it in my now not so virgin asshole.


I was now, technically speaking, no longer an anal virgin. He paused briefly and let me adjust. The cock head felt really big in my tight ass. I liked it when he began to wiggle his cock in slow circles. Every so often he would gently thrust forward and sink deeper into my ass. After seeing the massive size of his cock – 8″ long and thick like my wrist – you would think that it would hurt up my tight, round, little ass. In actual fact, he was so gentle and slow that I didn’t even realise it when he was fully seated up my ass. I now had a cock so huge, thick, and throbbing buried so deep in my ass that I felt like I was being fucked by a horse, but it didn’t hurt me. He moulded his body to mine, grabbed my firm tits and began to ride me slowly with short strokes – it felt so good that I was soon pumping my ass to his slow rhythm and whimpering. Slowly he increased the length of the stroke and before long he was pulling back until only the head was in me and slowly sliding it in me – right to the hilt and balls deep. I was so turned on.

“Fuck meee!! Oh please fuck me!! I need you in my pussy. I’m so fucking hot for you.” I begged.

He now held me by my hips and as he entered me, he would pull me back towards him – with his thumbs he would pull my ass cheeks apart. As he pulled out he would squeeze them together. His paced picked up and I could tell that he was going to come. I hoped that he would soon have me on my back, huge cock in my pussy and me with my legs in the air squealing as I approached orgasm. His thrusts became harder as he began slamming his cock into me. He was soon riding me so hard that I would squeal with each thrust – I knew that I’d feel it tomorrow. It seemed like an eternity that he power fucked my ass. I squealed and writhed uncontrollably as I struggled to endure his powerful anal thrusting. He would pull out and ram his huge cock deep into me. I didn’t know how much more I could take. He kept riding me hard and pushed me over the brink.


Suddenly he grabbed my tits and with his giant cock fully seated up my asshole, his body stiffened. His cock exploded up my ass – a veritable river of semen was injected into my ass. I gasped in disbelief as come was injected in powerful jets.

“Please fuck my cunt,” I whimpered.

Now in all aspects I was no longer an anal virgin. When he finished, he remained mounted, but his cock softened quite substantially.

“So what did you think of that?”, he asked smugly.

“Fuckin’ A! Do me in the ass some more. You are so fucking huge, but it doesn’t hurt. It feels so good. My cunt is dripping wet. You fucking me in the ass is such a fucking turn on.”

“If I keep ass fucking you, you might be walking funny tomorrow.”

“I know that I will be because your cock is so big; especially if you keep banging me in the ass so hard, but I don’t care. It feels so good when you ass fuck me.”

“Did you like the spanking?”

“Spanking? You didn’t spank me – you whipped me and it really fucking hurt, but it gives an edge to the fucking that I’m taking in my ass. I’m so horny and my pussy is dripping wet. Will you please fuck my pussy.”

“Nope. Ass fucking only. I’m going to fuck you in the ass until you can’t walk properly. I’m going to whip your ass, fuck your ass, come in your ass, rest in your ass and fuck your ass some more. I’m not going to let you touch your pussy and I’m not going to let you come.”

Now I knew how he was going to break me. He knew that he could fuck my ass as much as he wanted without ever bringing me to orgasm. He was going to ass fuck me and make me so horny. He was going to break me.

He started to rub my clit in firm circular motions which caused my body to twitch involuntarily.

“Oh fuck,” I gasped. Then I felt it. His cock began to grow. After his powerful orgasm, his huge, thick cock shrunk quite a lot. It became soft and relieved the strain which allowed my asshole to shrink and relax. Now I could feel his cock getting thicker, harder and longer. Without even moving it, I could feel the head moving deeper and deeper into my asshole. The increasing thickness was stretching me. His clitoral assault increased in intensity – he was rubbing harder and faster which caused me to writhe involuntarily. The more that I writhed and quivered the bigger and harder he got. I was on the brink – gasping, squealing, grunting, writhing and squirming. Suddenly he stopped.

“Oh God please. Please I’m so close. Please bring me to orgasm. I’m begging you – please make me come.”


“PLEEEEASE”, I begged.

With the leather strap, he slapped my ass really hard about five times and then began to ride me again. I screamed with each heavy whipping. His huge throbbing cock buried so deep into my vitals was slowly pulled out. Inch after throbbing inch of thick, woman taming man meat was pulled out of my ass until only the huge head remained up my ass. He then began to slowly wiggle it a tight circle. I don’t know why but this was driving me through the roof. I was panting and grunting uncontrollably as my body trembled and quivered. He held my tits and twiddled my erect nipples as he began the long journey to bury his cock in me. Over and over again he stroked me – slowly at first and then faster and faster until he was riding me hard. He was slamming his huge cock into my ass so hard that I was being knocked forward with each thrust. I had to hold onto the headboard so as to weather the anal assault. My cunt was so wet from arousal that I was screaming and begging to be fucked in my pussy. Suddenly he again exploded in my asshole. Powerful jets of semen were injected deep into my helpless asshole. Again his cock shrivelled. He remained mounted and after a brief spell he began to caress my cunt. He would run his fingers along my slit – never touching my clit. He would slip his finger into my dripping cunt and then back along my slit. I was so horny that I was trembling and in tears begging him to let me come.

“Please fuck my cunt. I need your cock in my cunt. I’ll do anything for you if you please fuck my cunt.”

“Can I tie you and spank your bare ass?”

“Yes please. You can spank me, but please bring me first.”

“Can I tie you and whip you?”

“Goddamn it. Please I’m begging you. Whip me, beat me, do what ever, but please make me come.”

Hi s cock was once again a huge, raging hard-on buried deep in my ass.

“No, I will not let you come. I will however beat your ass as punishment for trying to bribe me.”

He began to ride me slowly at first and then faster and faster making me scream and plead for mercy. I was so desperate for an orgasm. With each orgasm, he was taking longer and longer to come. He was riding my ass longer and longer which made me hornier and hornier. My ass was so tight with his huge cock inside me that every time he came, his cock exploded even though with each orgasm less and less semen was injected into me. By now my innards were filled with so much come that I had an overpowering need to eject it. Once again he exploded in my ass, his cock softened, but this time he dismounted me

“I have to take a leak,” he informed me.

I was thrilled as I thought that I would have the opportunity to masturbate myself to orgasm. My thrill was short lived when he commanded me to stand at the end of our canopy bed and then proceeded to tie one arm to each of the bed posts. When he was finished, my arms were spread and tied to the tops of the bed posts and my legs were spread and tied to the base of the bed posts. He began to stroke my clit again ever so gently; driving me wild.

“Please,” I sobbed. “Please let me come.”


With that he tied a blind fold across my eyes and walked away.

I stood there all tied up spread-eagle helpless and fully exposed to his every whim. I felt disorientated and at the same time horny as fuck.

“Please come back to me”, I begged.

Finally I heard him return.

“I will now punish you for your attempted bribery,” he said. “After the punishment I may be nice to you, but then I may not.”

I then felt his huge cock head nosing between my ass cheeks. When I felt it touch my stretched asshole I flinched involuntarily.

“Oh I see. Still a little rebellious and not readily willing to submit to my every whim. I guess more punishment is in order. I’m not going to use the strap this time, now I’m going to use the riding crop. I’m going to give you five, but I want you to ask for each of them. You will tell me in a convincing tone of voice that your behaviour is unacceptable and that you should be punished.”

“No, please. I’m not rebellious. Your cock is so big and thick that I can’t help but flinch when I think of my tight little ass and your huge cock. Please don’t whip me again. My ass is yours. Please sodomise me.”

He whipped me four times right across the base of my ass where my ass meets my thighs – two on the right, two on the left and one right across my ass. I squealed and writhed with each blow and between blows I begged him to sodomise me. Luckily he did not hit me very hard – just enough to make me squeal and writhe. He then untied me and I quickly assumed a submissive position on the bed.

“On your back with pillows under your ass,” he commanded.

I was sure that he was now going to fuck my pussy. He then proceeded to tie my wrists to the bed posts at the foot of the bed so that I was unable to move closer to the head board. At this point I could not fathom what his plans were. He then proceeded to tie my ankles to the head board. I was now securely tied with my knees to my chest and legs splayed open and since I was still blindfolded, I had no idea what was happening. The position that I was in was not uncomfortable, but it occurred to me that my ass was perfectly positioned for additional spankings. I soon felt a finger penetrate my dripping pussy and my asshole. A tongue begin to gently lick my slit. In no time I was writhing and gasping as I approached what I was certain to be a colossal orgasm, when suddenly all the stimulation stopped except for the anal stimulation. A second finger and then a third were introduced into my gaping, stretched asshole.

“Oh please let me come. You’ve been torturing me enough. Please let me come. I’m begging you please let me come.”

I was so hot that I began to sob as I begged for mercy. I then felt a thick phallus penetrate my cunt. I knew that it wasn’t a real, flesh and blood cock, but rather a really big dildo. It felt so good that I whimpered and gasped as it was slowly pushed deeper and deeper into my cunt. Once it was fully inserted it was slowly removed. The fingers were still teasing my asshole.

“Oh God that feels so good” I gasped. I was barely able to speak. The treatment was so gentle that I was not getting any closer to orgasm, but the sensations were delicious and wicked. Soon, I was unable to speak coherently – only grunts, groans and squeals. The dildo was so big that my cunt was stretched tightly around it. Suddenly the fingers were removed from my ass.

“Oh please don’t stop,” I whimpered. The dildo began a rapid in and out motion that was rapidly driving me to orgasm. I started screaming and writhing when suddenly it all stopped. The dildo was slowly moved in and out – I knew that he was not going to let me come.

“Make me come you fucking asshole,” I screamed.

“I’m not the fucking asshole. Today you have the fucking asshole and I’m going to fuck you in your fucking asshole.”

The giant dildo was fully inserted in my quivering cunt. I then felt his giant cock head pressing against my asshole. Because of the huge size of the dildo in my cunt, he needed to apply a lot of pressure to penetrate my asshole. Suddenly the head penetrated me and the shaft was slowly buried into me. I was going crazy from the stimulation caused by the huge cocks buried in me. As he fucked my ass, I sobbed and begged for him to let me come. I pleaded with him to make me come. I begged him to fuck my pussy.

“Will you make another woman come by eating her pussy,” he asked?

Being very much against lesbian sex, I was surprised to find myself agreeing to it and interestingly not being repulsed by it.

“Will you put on a dildo and fuck another woman to orgasm,” he asked?

Again I was surprised to find myself not just agreeing to do it, but actually wanting to do it. He began to ride me harder and harder. He also wiggled his cock in circles further stretching my enlarged asshole until he again exploded up my ass.

“I’ve arranged for your cousin Suzy to join us. She wants you to eat her and fuck her before she fucks you and makes you come.”

I was again surprised that I was very agreeable. Suzy, a gorgeous red head, wasn’t really my cousin, but having grown up together, she may as well be my cousn. I was untied, and the blindfold removed, but the dildo was left in my cunt as a means of tormenting me further. There was Suzy dressed in stockings, and garters and nothing else. In one hand she held a big, fat dildo and harness. The other hand held a whip.

“Eat me well and I won’t whip you. Fuck me well and I won’t need to whip you.”

She dropped the harness and laid down in the middle of the bed with a pillow under her ass. She spread her legs and pulled her knees to her chest.

“Start eating bitch.”

As I bent over the edge of the bed, the irony of the situation was not lost on me. I always taunt him by telling him that he should get a fag to fuck his ass and now he was making me fuck a woman. As I licked her clit, I fingered her pussy and her asshole. Before long I had her panting and writhing. I then felt his huge cock pressing against my asshole and began to wonder how many times I would be ass fucked. My cunt was still filled with a dildo. I was so horny. Suddenly Suzy screamed and I felt her cunt and asshole pulsate around my fingers. I kept at it until she finished. Just before Suzy came, he exploded in my ass again, but remained mounted until I finished her.

“Get that dildo on and fuck me,” she ordered in a husky voice.

She remained with legs spread and waited for me to mount her. I climbed between her legs, positioned the fat dildo against her little cunt hole and pressed forward sinking all eight, fat inches up her cunt.

“God that feels so good. Fuck me hard you anal slut.”

I pumped her hard and slow deep and shallow and made her scream and writhe. I soon had her coming hard.

“FUCK ME HARD!!” she screamed and began to use the whip on my ass to get me to ride her harder and faster. The stinging whip was encouragement enough. I banged her hard and fast. Each stinging whipping caused me to cry out and writhe. As I writhed she screamed louder whipped me harder. My ass was on fire, my cunt was on fire.

“Please stop whipping me,” I begged.

“Fuck me doggie style,” she gasped.

I withdrew and she turned over on her stomach and waited until I mounted her. I again felt the huge cock head against my asshole. I was so stretched that he popped right in and sank balls deep without much effort. I then mounted Suzy and as I fucked her, I was fucked in the ass. As I fucked Suzy, she gasped and writhed as she had orgasm after orgasm. I too gasped and writhed from being ass fucked yet again.

“Fuck my cunt! Please fuck my cunt!” I begged over and over.

I suddenly had a wicked idea. When Suzy was about to come, I withdrew from her cunt and impaled her ass. The thick dildo made her scream. The dildo popped in and I slid it all the way in. As I sodomised her, she screamed and writhed trying to dismount me.

“Fuck you bitch,” I said. “If I get ass fucked then you do to.” The difference was that by now my asshole was stretched enough that his huge cock didn’t hurt any more and I was enjoying being sodomised – the huge dildo in her asshole was obviously causing her discomfort. Soon after I impaled her ass, his cock again exploded up my ass. He withdrew and allowed me to power hump Suzy’s ass. A short while later, he pulled me off of Suzy and mounted her with his huge cock. She really squealed and writhed as he rode her to another orgasm. I was thankful that it was her because my ass had been used so much that the come up my ass was running out of my huge asshole. I watched him slam bang her ass in amazement. I could not believe how much his cock stretched her asshole and I thought about how that was my asshole not to long ago. Her body writhed and she pumped her ass. She reached back and started to rub her cunt to bring herself to orgasm. She came hard – her body went stiff and she screamed so loud that it would wake the dead. She took forever to finish coming and when she did, she collapsed in a heap. He kept banging her tight little ass until he came. When he dismounted she was whimpering.

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