Surprise Pegging

“Put this on,” I told Toby. I smiled wickedly at him to let him know that what I had planned was going to be something special. I’d been working on this for the months leading up to his birthday. I’d scoured sex sites and watched porn to get ideas. He had no idea what I was up to but if I had my way, he was going to have a birthday he wouldn’t soon forget.

“A mask? Why?” He looked perplexed as he fingered the soft black ski mask I had given him. I would cover it with a blindfold once I had him locked into place. I knew that he was the one for me. I knew it because I could control him and he loved having me in control. He shrugged and put the mask on.

“How do I look?” his voice was now slightly muffled but I could still understand him.

“You look like you’re about to have a really fucking good time,” I laughed. “Now take off all your clothes. Especially the underwear,” I added, knowing he would try to get away with keeping it on unless I directed him otherwise.

“Yes, Mistress,” he said, making his shift into character as the scene began. 

Now lay down here, with your ass in the air,” I gestured toward the bench I had bought specifically for this night. It put his ass up in the air and his head angled toward the floor. I worked quickly, strapping him down to the bench with the precision of a long-time dominatrix. 

I was younger than Toby by quite a bit, but it didn’t matter. I still had him by the dick and he was mine now, just like I always knew he would be. When we had first started dating he had been the one in control and I had let him think that he was, planting subtle hints that someday he would be my bitch if he kept on this path with me. Now he was completely my bitch and I loved it so much. He was about to love it too.

“You ready for your ass to get brutalized, baby?” I asked him, my voice dripping with sadism. I couldn’t wait to see him completely destroyed. “You want your birthday present?”

“Yes, Mistress.”

“That’s a good boy, Toby. You’re a good, good boy,” I said patronizingly. I grabbed a dildo and squirted it with lube. I coated the toy but first teased his asshole with my finger. He was already moaning with just one of my slim fingers so I added another to see what it would make him do. His howling got louder and I knew he was ready to take the dildo. It was a thick one, almost as thick as the next tool that was going to fuck him. I pushed the dildo into his asshole slowly and carefully. I wanted it to feel good and not hurt. The pain would come later. For now, I worked it slowly in and out, letting Toby enjoy the sensations. I was transfixed by the way his butt swallowed that toy.

“Oh God, Mistress! Faster! Please!”

“Not yet. You’ll wait for your surprise.”

“Yes, Mistress.”

“Good boy, Toby. Now I’m going to shove this whole dildo up your ass. I have to go get my strap on. I want you to try to hold it in while I’m gone. Can you do that?”

“I will try, Mistress.” 

“Good!” I shoved the dildo in all the way and he made a noise that really turned me on as it hit his depths. I tied a blindfold around the ski mask to cover his eyes.

“What are you doing, Mistress?”

“I’m just making sure you’re surprised. I’ll be right back.”

I ran out of the bedroom door and down the hall to the guest room. I let out a sigh of relief to see Ken was still there. I had met him on a BDSM website and asked him if he wouldn’t mind coming over to help me with my birthday present for Toby. To my shock, Ken was eager and excited. He was tall, with rippling muscles and a huge cock. I knew that Toby had never taken a cock this big. In fact, I knew that Toby had never taken any other cocks at all. This was going to be his first one and it was going to be a huge shock for him.

My pussy was so juicy.

“Lydia! Is it time?” Ken asked in a loud whisper.

“Yes. It’s time! Do you need a fluffer or are you ready? He’s tied down and waiting so if you need a little attention, I’ve got you.”

“Bend over then,” Ken said.

“Just don’t make a lot of noise,” I told Ken as I bent over and let him fuck my pussy. I’d fucked him plenty of times behind Toby’s back but I knew that Toby would understand once he got his present. I had only been doing what I needed to do to make his dreams come true.

Ken pounded my pussy hard and fast, relentlessly using me until I had cum several times, struggling to hold my screams back. I couldn’t believe how winded I was and I knew I was done. Ken’s cock was hard. It was time for him to do what he had come here to do. I stood up, pushing my hand back to indicate that I was finished being fucked.

“Come on. It’s time now. You ready?”

“I’m nervous,” Ken admitted. “But I’m ready.”

“Thank you for doing this.” I gave him a kiss on the cheek and pulled him down the hall, my finger to my lips to indicate that Ken should remain quiet. I opened the door to the bedroom and watched Ken’s face pull into an expression of shock. He couldn’t believe what he was seeing.

“Mistress? Are you back?” The dildo I had asked him to hold flopped out of Toby’s ass and onto the floor at that moment. I don’t know how Ken held it together but he managed to remain silent.

“Didn’t I tell you to hold this in your fucking ass?” I slapped him hard. “Disappointing. Maybe you’ll do better next time, honey. You will definitely be punished. I found my strap on. Are you ready to get fucked?”

“Yes, Mistress! My ass is hungry.” 

“Good! I hope you enjoy this then.” I pushed Ken toward Toby and I grabbed Ken’s cock and guided it inside of my boyfriend’s ass. I grabbed the lube and squirted it all over Ken’s cock. I felt so powerful as I watched Ken pump his cock in and out of Toby’s ass. I knew that it probably felt amazing for him and I knew that he was going to be so happy when he found out that he got fucked by a real dick. Toby was moaning and screaming like a little bitch.

“Your cock feels so different. Is that a new dildo?”

“Yes!” I called, but I realized my mistake. I was too far away from him to be fucking him in the ass.

“Lydia! Is there someone else fucking me in the ass right now?”

“Don’t be mad, baby. It’s just a friend of mine.”

“A girlfriend with a strap on?” he asked.

“No, a male friend. You’re taking your first cock! Happy birthday, baby!” I screamed. You want me to take the blindfold off now?”

“Lydia! What have you done?” Toby screamed.

“Should I stop?” Ken spoke up.

“No!” I screamed at him. “Fuck him harder. And you, shut the fuck up and look at the first man to ever fuck you!” I pulled the blindfold and the mask off of his face. The shock in his eyes was priceless. My pussy was so much wetter now that I could see the distress in his eyes. He needed to cum and so I situated myself in front of him, even though it was the most awkward of angles, opening my legs so he could eat my pussy. “Now eat my pussy and take it in the ass like a good boyfriend. And Ken, I said fuck him harder.” 

“Fuck! Fuck!” Toby screamed but I pushed his head into my pussy until I couldn’t hear his screams anymore. I was loving this, grinding my pussy into his face as Ken pounded his ass.

“I’m going to cum!” Ken screamed.

“Cum on my pussy!” I sprung up and bent over in front of Ken. Ken pulled out of Toby’s ass and squirted his load all over the outside of my pussy and asshole. “He came all over my pussy and ass. Guess who is cleaning it up?”

“Me, Mistress.”

“Yes, you, Toby.” I turned so my ass was in Toby’s face, getting on my hands and knees on the bench in front of him. He was still completely bound and he had no real choice. He licked and sucked the cum from my pussy and ass as Ken looked on, dumbfounded by the situation.

“You guys are…different…” he said. “I think I should go.”

“You don’t need to go,” Toby told him in his normal voice. His bitch voice was gone. “Stick around. Fuck my girlfriend. She has a sweet pussy. You can fuck her.”

“Oh, I’ve fucked her.”

“Dozens of times,” I added for emphasis.

“Lydia! You didn’t tell me that.”

“It was part of your birthday surprise!”

“Well, this is definitely some surprise.”

“I know what you like. Want to watch me fuck Ken while I tie you to the chair?” I pointed at a bondage chair we had bought together a few months before. “Can’t you stay a little longer, Ken?”

“I guess I can,” Ken admitted. “I just don’t want to get in the way.”

“You’re not in the way,” Toby told him and even I could hear the desire in his voice. He had gotten a taste of real dick. I had created a monster in Toby. From that day on, Toby took more dicks in his ass than most gay men. The best part was, I got to make him do it. I always knew he would be my little bitch. He still is and he always will be. Ken will probably always be my bitch too.