In the last chapter, my sub Peter helped me live out my medical fantasy. So wanted to help him live out one of his.
If you’ve read my other stories (and you should), you know that he loved all things anal, including strap-on sex. His fantasy was to blindfolded and fucked in the ass by a stranger. Eventually, he’d want to see the stranger’s face, but not until she’d cum.
He’d sessioned with most of the other dommes here at Rebecca’s Hidden Chamber, but there were some new girls he’d never been with. He suggested we use of them — I just shouldn’t tell him which one.
I had a better idea.
I’d been sitting in with another punk band — I played guitar in my main band, and was playing bass with these girls. One girl was straight, one was bi and the other gay, but they’d all fucked around with each other over the years. They were kind of crazy, but mostly in a good way.
I pitched the idea to them, and they liked it. Rachel, the straight girl, had never used a strap-on before and was the most excited. Kristen and Molly — the gay and the bi girls, respectively — had strap-on experiences but had never fucked a guy up the ass.
So now I had three new girls to ass-fuck Peter. See what I do for the boy?
I called Peter then and there and we set a date. I had the girls show up twenty minutes early and put them in one of the rooms. Kristen and Molly brought their own harnesses, and I loaned Rachel one from the dungeon. Then I distributed the dildos — vibrating Leos. They’re the big brother to the Mistress, about an inch longer and a half-inch wider. Peter had gotten too comfortable with the Mistress. I wanted to stretch out his asshole.
I left the girls alone and waited for Peter. I led him to the room across from where the girls were hidden. Peter paid me and I told him to get comfortable. I gave Dahlia, the phone girl, the money and returned.
He was naked and playing with himself.
“That’s enough of that, mister,” I said.
“I thought you liked watching me stroke my cock,” he said.
“I do, but you’ve got a big afternoon ahead of you. So no more touching yourself.”
He put his hand down.
“Did you do what I asked?”
“Yes,” he said. “I gave myself a thorough enema, and I put a butt plug up my ass an hour before I came here.”
“Good. I’m basically pimping your ass today, so I need you to be a good anal whore. Ready?”
He looked confused.
“No hugging?” he asked. “No nipple play warm-up?”
“This is your warm-up. Bend over.”
He looked flustered, but his dick was twitching. He was going to submit anally — much more than he knew — and it turned him on.
He bent himself over the side of the couch and I approached him. I put the Leo against his asshole and pushed gently. He took most of the head in before I felt resistance. He’d never taken a cock this big before. But he was going to today.
“Relax your anus and push back onto me. I know this is a bigger cock than you’re used to, but anal whores need to be able to take big cocks, right?”
“Yes, Mistress,” he moaned.
His anus slipped over the head of the dildo. I gave him a moment to get used to it, and then I slowly pushed the whole thing in. He groaned — the Leo was filling him up. He been fucked up the ass many, many times before — by me. But now he was getting fucked by a big cock.
In fairness, Peter’s cock was almost exactly the same size as the Leo — 7-1/8″ x 1-1/2″, for those of you playing at home. So I guess I have to say he has a big cock, too.
I slowly pulled the cock back. I felt the head catch on his anus, and then I slid it back it. Over time, I picked up the pace. He grunted each time the cock slid up his rectum. I could feel his anus relaxing, so I became more aggressive with my fucking. In fact, I took the little finger from my right hand and slowly slipped it in his ass along side the cock. He was opening up nicely.
“Grab your cheeks, whore.”
He obeyed, and I pulled my cock out.
He was gaping. Nice.
I slammed my cock back into him and pulled out. I did it again. I was fucking him like a whore.
“Time for your hood, bitch.”
I’ve said this before — I’m not a fan of words like ‘bitch’ and ‘cunt.’ But in these situations — deep, dark sexual situations — I’ll tolerate, and even enjoy. And fuck you, you cunt, if you disagree.
“No blindfold?” he asked.
“Blindfolds fall off, bitch. You get the gimp mask today.”
This was fun!
I put the hood on his head and zipped him in.
“I thought I might orgasm with you first …” he said.
I slapped him. He didn’t see it coming. He couldn’t, not with the hood.
“Whore! Don’t talk to your pimp like that. I own that asshole. It’s mine! I say when and where it gets filled. I say who gets to fill it. When I want you to cum, I’ll let you know. Got it?” ”Yes, mistress.”
“Stick out your tongue!”
He obeyed, and I pushed my ass against his face.
“Lick my asshole, slave. You want to get off? Then clean my fucking ass with your tongue!”
I was getting into it. My regular readers may remember that I didn’t have a lot of experience with anal play — at least receiving. But Peter’s tongue felt good on my ass. And, since he was a good boy, he did more than lick. He started sticking his tongue into my anus.
This I liked. This felt good.
I pushed my ass against him, smothering him. I reached down and turned the vibe on in the Leo. I pushed the dildo hard up against my clit.
God, this felt good.
“Fuck my ass with your tongue, whore. Make me cum.”
He put his hands on my ass and spread them wide. He was burrowing his tongue into my asshole as far as it would go. I loved the effort he was putting into it, and I loved the vibrations on my clit. I felt my asshole begin to open up, and his tongue slipped further inside me.
I came, and fell on the floor.
“Jesus Christ,” I said. “That was great.”
“Thank you, mistress.”
“I’m going to have to have you eat my ass again,” I said.
“I’m happy to please you anally, mistress,” he said. “I adore your ass.”
“As well you should, my slut. You should adore all of me.”
“I do, mistress. I do.”
“Are you ready?” I asked. “Ready to get fucked up the ass by a stranger?”
“You do want to get fucked up the ass by a stranger, right? This is you fantasy, right? Something you jerk off to?”
“Good. Hold that thought, and give me your hand.”
I led Peter out of the room. I knocked on the door across the hallway, and slowly opened it. Standing in front of me were three nudes girls sporting strap-ons. They looked hot. For a moment, I wished that I was the one getting gang-banged.
The girls had placed a mat on the floor, and I had Peter stand in the center. The girls seemed to think Peter was cute, and gave me the thumbs-up. “Peter, we’re ready to fuck you. Please tell us what you told me in the other room.”
“This is my fantasy — to get fucked up the ass by a stranger.”
He seemed a little nervous, something I’d never seen before. Apparently, being nude and talking about getting fucked up the ass in front of a stranger — or three! — was not something he was used to. And he couldn’t see the strangers, so he couldn’t see their reactions.
“What else, Peter?”
“I masturbate to this fantasy.”
I looked at Kristen.
“A lot?” she asked.
“Yes. I masturbate to this fantasy a lot.”
“So would you like me to fuck you up the ass?” she asked.
“Please. Please fuck my ass.”
I looked at Rachel.
“What about me?” asked Rachel. “Or me?” asked Molly.
Peter was confused.
“I have three friends in this room, and they each want to fuck your ass. To my mind, that’s a gang-bang.”
“Have you ever been gang-banged, Peter?” asked Rachel.
“Anally gang-banged?” added Molly.
“No,” said Peter, “never.”
“Your cock is getting hard,” said Kristen. “Does the thought of it turn you on?”
“Yes, it does. Very much so.”
“Then bend over, you fucking whore. We’re gonna take you down.”
I led Peter over to the couch and bent him over. Kristen stepped behind him and slapped her cock against his asshole.
“Ready for me, big boy?”
She didn’t wait for an answer — she just plunged her cock into.
Peter tensed and rose up.
“Relax your anus and breathe, my anal whore. There’s going to be a lot more of that,” I said. He laid back down on the couch and took his fucking. Kristen was getting into it. She’d turned on her vibe and she was fucking for her pleasure. It was all about her getting off — she didn’t care about Peter. He was just a hole to her.
That’s what he wanted. To be used. To be an anal fuck toy. And he was doing a great job.
Kirsten paused and pulled Peter’s hips further up on the arm of the couch to get better leverage. She pounded away on him, beads of sweat forming on her brow.
Now she was moaning, too. She thrust forward and fell on top of Peter. She’d cum. Peter was twitching under her, so I knew he’d cum as well.
“Peter, you should thank Kristen,” I said.
“Thank you, Kristen,” he said, “for fucking my ass and making me cum.”
Molly was up next. She stood behind Peter and pushed her cock into his ass. She took a few practice strokes and she was off to the races. She grabbed Peter’s hips so she could thrust into him harder. Peter’s moans grew louder, and he came. Molly adjusted the vibe in the Leo, and pounded away. She moaned and stepped back. She’d cum, too.
“Manners, Peter,” I said.
“Thank for fucking my ass. Thank you for making me — Oh!”
Rachel couldn’t wait. She practically threw Molly to the side and rammed her cock up Peter’s ass. She went at him with a vengeance. Rachel was straight, and I suspect someone had not been nice to her asshole at some point. She was really laying into him.
I was worried this might be too much for Peter, but didn’t use his safe word. He was moaning like a banshee, though, and making some odd gurgling noises, too.
Then Rachel reached over, put her fingers in his mouth and pulled back. She was fish-hooking him now, something I’d only seen in extreme porn videos. She was destroying him, and she was loving it. Fuck, even I was getting wet again.
Peter went silent and tensed up. His hips started bucking, but Rachel wasn’t done with him yet. She drove her cock into him faster, until she came. She pulled out of him and stepped away. Then Peter’s body started twitching, and he let out a low moan.
This was one intense orgasm.
“That was fun,” Rachel said. “Can we fuck his face? I want to fuck his face.”
Peter tried to respond, but he was basically incoherent. He tried to get on his knees, but Rachel pushed him back on the couch, in the middle. She made him lie on his back, with his feet in the air and his head lying off the couch.
Kristen went first, and she got Peter to deep throat her. Molly was next, and was more aggressive. Peter gagged some, and a sheet of drool rolled out of his mouth and down over her face. Rachel, though went crazy. After she got in his mouth, she grabbed his head and began slamming it up and down on her cock. Then she’d stop to let Peter take a breath. Then she’d start fucking his face again, treating his head like it was some kind of sex toy.
She stopped again, and pinched his nose. Now he couldn’t breath at all, not with that cock in his throat. I thought this might be taking it too far, but when I looked at Peter’s cock, it was rock hard, with a rivulet of pre-cum dripping off of it.
He was liking this.
I pulled him off the couch and placed him on his knees on the mat. It was time for the grand unveiling. I unzipped the gimp mask and slid it off his head. This was the first time Peter saw the people who’d fucked his ass and face.
Peter drunk in the sight. Three sexy girls, nude except their strap-ons. And he had had each of those cocks down his throat and in his ass. He’d been used and abused, ridden hard and put away wet. Except that I wasn’t done with him yet.
Molly and Kristin got Peter on his back and held his legs. Rachel sat down behind him and cradled his head in her lap. I got the lube — a lot of lube.
Three fingers went in his ass with no problem. The fourth slipped in smoothly, and I felt my thumb enter his anus, too. Now all I needed was the knuckles.
Peter closed his eyes and moaned.
I slowly corkscrewed my fist in and out of his ass. A couple of knuckles made their way in. I put some lube on Peter’s cock.
“Play with yourself Peter,” I said, “and breathe.”
“This is what you want, right,?” Rachel asked, sweeping the hair from eyes. “To jerk off and cum in front of a bunch of girls? With a whole fucking fist up your ass?”
Peter whimpered “yes.”
The last few knuckles slid in. But I wanted to go wrist-deep. I pulled out and applied more lube to my fist. Then I corkscrewed it back in. I kept pushing gently, and felt his anus stretch up over my hand. I pushed up into his rectum. My hand had completely disappeared.
“How does it feel, Peter?” I asked.
“So full, so full,” he said.
He could barely speak.
Then I began fucking his ass with my fist, pumping away at him. He tried to squirm, but the girls kept him in place. I kept fucking him, watching his face contort with pleasure. I kept up my pace, waiting for his cock to explode.
His hips rose up off the ground, and he shot his load on his chest. He laid back down, and twitched. He may have stopped ejaculating, but he was still coming. I stopped fucking him. After the last twitch, I slowly pulled my hand out of him. “Oh, my God,” he said. “Oh, my God.”
I held up my fist.
“This was in you,” I said. “This was in your ass.”
He just stared.
I looked around at us. We were all covered in lube, sweat and Peter’s drool — the face-fucking had been especially messy.
I handed Peter a roll of paper towels.
“No,” said Rachel. “I have a better idea. Let’s hit the showers.”
We were too messy to wrap ourselves up in towels, so the five of us simply walked out into the hallway and down to the bathroom. Dahlia, the phone girl, came out to go to the front door and her jaw dropped. She didn’t know what we had done, but she could see the damage.
“I’m going to shower him down with my pee,” said Rachel. “Would you like that? To drink my piss?”
Peter didn’t say anything, but he knelt down in the shower and opened his mouth. Then she spread her pussy lips and squatted down, spraying him with her piss.
It filled his mouth, and he swallowed. But Rachel really wanted to give him a shower, and soon he was drenched in urine. Then it was Molly’s turn, and then Kristin’s. Streams of piss flowed down Peter, into the tub and down the drain. Then it was my turn.
“Who owns your ass?” I asked.
“You do, Mistress Kathi,” he said.
“And who opens your mouth?”
“Then open wide.”
This was our first time engaging in piss play. But looking down at Peter and watching as my liquid splashed in his mouth was a huge turn-on. It was like I was giving him a huge piss facial.
Thank you, Rachel.
And thank you, Peter. I know you loved your anal gang-bang. You deserved it.