WBDP - Going Nude for Homeless

"Fuck, I'm going to cum. Mistress, let me cum!" She cried out and Bella gave her permission.

Her body wriggled delightfully as her spasms of pleasure swept through her body. When her shivers ended, Bella pulled her face against her cunt and told her that she'd remove the nipple clamps after Emily made her cum and not a moment before. She kept one hand on the chain with which she tugged on her distended nipples while Emily eagerly licked at the dripping pussy before her face. It was apparent that Emily had limited practice pleasuring a woman, but again her enthusiasm was remarkable. Bella quit holding Emily's head and only controlled her with the nipple chain.

"Master, my slave is going to make me cum. Please let me cum?" Bella asked.

"You may cum, dear," I replied and her moans filled the room as she tugged the clamps from Emily's nipples, grabbed her head again and ground her hips against the lips and tongue of her friend. When her orgasm was finished, she stepped back and Emily's face was damp from her nose to her chin with a couple drops of orgasmic fluid dripping onto her breasts. Her face was flushed, but she smiled up at us.

I had Brianna lie down on one of the padded benches and directed Bella to position Emily over her in a 69 position. The bench was positioned at a height where I could easily penetrate Brianna. Emily was instructed to satisfy Brianna while I fucked her. Bella was instructed to use a riding crop on Emily's ass if at any time she seemed to be flagging in her duties. From the moans I heard from Emily, it was apparent to me that Brianna was partaking of the fresh, smooth nookie in front of her face. Occasionally as I fucked Brianna, I would grab Emily by the hair and lift her head and thrust my cock into her mouth. If her face didn't immediately proceed to Brianna's pussy as soon as I removed it from her mouth, Bella would swat her ass to stir her to action. Emily's mouth received no rest, either lapping at Brianna's cunt or my prick constantly. Brianna reached her peak first and was granted permission to cum. I moved my cock back to Emily's mouth and I felt her gurgle as she tried to speak. My cock gagged her as she spasmed to another climax, but I kept my rod firmly in her throat and fully impaled her throat as she quivered under the pleasure of Brianna's talented and experienced tongue. Before she could gasp for breath, my cock was back in Brianna's cunt pounding toward my own climax.

Bella delivered five fast cracks to Emily's ass as she failed to immediately pleasure Brianna while her own orgasm was still cresting, but she finally applied herself back to Brianna's clit while I pounded the sopping hole below it.

"Fuck, I'm going to cum again, Master. You fuck me so good, Master. Please let your slave cum," Brianna cried.

"Wait, cum with me," I panted. "It won't be long."

"Please hurry, Master," Brianna moaned.

Five more deep thrusts and my cock began to spew my load into her creamy cunt and I shouted, "Cum with me, slave!"

"Fuck me, fuck me hard! Ram your cock into my steaming cunt. Lick my clit, slave. Nibble on that nubbin. Oh, fuck me!"

When my sack was drained and I began to shrink, I pulled out my cock and thrust it into Emily's mouth again, ordering her to clean me thoroughly. She was still engaged in this task as Marcia entered the room with two other slaves, all carrying trays of assorted goodies from the kitchen.

"What did I miss?" Marcia asked, setting down her tray and directing the others to do the same.

"Bella was demonstrating her talents as a Dom with Emily by trussing her up and having her lick her cunt. Then Emily licked Brianna in a 69 as I fucked Brianna, occasionally sticking my cock in Emily's mouth while Brianna licked Emily's cunt and Bella swatted Emily's ass if she wasn't working diligently at either task. In other words, not too much."

"Not too much? It sounds like everyone climaxed except me. Next time we should go to the dining room together so I don't miss anything."

"I'll make sure you get your fair share before we're done, little slave."

"Make sure you do, Master. You know how much your little slave likes to cum."

We made our two guests sit on their butt plugs while we fed them. Marcia had delivered a selection of crackers, meats, cheeses and fruits. I don't think they got a single morsel of food that wasn't first applied to a tit, a cunt, a cock or balls before it passed their lips, or ours for that matter. We were all hungry as their wasn't much left on the tray when we were sated.

"I think it's time that our guests be punished for climaxing without permission. Emily, you climaxed twice without permission. I'm going to have to think of something appropriate for the double infraction."

"Master, your cock was in my mouth. I tried to get permission but it's hard to talk around your prick."

"Then you should have held out or made arrangements for a hand signal. I'm sorry, but you'll have to pay. I have to get something from our room first, why don't you all get better acquainted while I'm gone. Brianna is in charge of all orgasms while I'm away."

I went back to Brianna's room and found the two We/Vibes that my slaves had been wearing to the auction. They had been removed hastily and not washed before we retired, so I washed them both in soap and water. The remotes were in the pockets of the tuxedo pants that I'd worn last night. The whole process took no more than ten or fifteen minutes and when I returned, Marcia and Brianna were lying on padded benches while Emily and Bella had their faces buried in the cunts of each respectively. Emily's fingers were rubbing at her own clit as her tongue worked Marcia's. Bella was being more professional and her fingers were working Brianna's sheath and g-spot. Marcia's eyes were closed in ecstasy. I walked up to her and placed my hands on her breasts, kneading them and tugging at her hardened points. She opened her eyes and smiled at me.

"I'm going to cum, Master," she said. "Brianna gave me permission to cum when I wanted."

"Good girl. You deserved to cum. You were behind."

I found a nice double dildo and returned to the quartet. Brianna was screaming out her climax as I returned. I told Emily and Bella to return to their chairs and I had Brianna lie down on the floor where I fastened her down spread-eagle. I inserted one end of the large double dildo in Brianna. I had Marcia lie down cunt to cunt and inserted the other end of the dildo in her damp folds. I had them get closer until at least six inches of the monster dildo was penetrating them both, then bound her down as well, her legs over Brianna's.

"I thought it was the new slaves being punished, Master."

"You're not being punished, you're being pleasured."

"Yes, Master."

I tossed suspension boots to the Emily and Bella and told them to put them on, asking for my assistance if they needed it. Bella was familiar with suspension equipment and had hers on first, then helped Emily fasten hers. I directed them to lie next to the others, attached spreader bars to their ankles, and raised them with the ceiling tackle until they were dangling just above Brianna and Marcia, back to back. I strapped their waists together and lubed up the two vibes before inserting them in their still frothy cunts.

"We're going to have a little contest here," I said. "You two will be assigned to lick or otherwise satisfy the cunt of the slave below your heads while you are being whipped. The slave will keep track of how many times that she cums. Whoever has satisfied her slave the most when the punishment has ended will win and the other will lose. Bella, you are to receive 50 strokes to the front of your body; Emily will get 60. The loser will be fucked in the ass. There is just one other caveat to our contest. We will deduct your orgasms from the total of the slave you've been servicing. You have each been given a We/Vibe which your slaves will assure you is quite effective in giving orgasms to the wearer. It may be possible that you both are in negative territory when the contest ends, but the higher number still wins. A smaller negative number is higher than a bigger negative number. Any questions thus far?"

No one had any questions, Marcia and Brianna were practically quivering to start. Their hips were rocking back and forth towards each other as much as their ties allowed to achieve more penetration from the double headed dildo.

"No one is required to ask for permission to cum, but our two new slaves will have to signal me when they are having an orgasm as I may not otherwise be able to tell, no matter how experienced I am at detecting the pleasure of a woman. I would suggest holding out a finger so that you can keep pleasuring your partner with your mouth. There is only one other piece of information that you may wish to have before we start. Both of your partners are quite orgasmic, so I'm sure they will both cum many times during the contest, but Marcia has won a contest for her orgasmic prowess. The other factors you may wish to take into consideration are how effective you are at giving your partner an orgasm and how orgasmic are you. Will you cum more or less than the other contestant. You can talk over who you want to be partnered with or we can flip a coin to determine if you can't reach a decision."

Both Emily and Bella remained deep in thought for a moment, had a whispered conversation together which only the two spread-eagled women could hear.

Finally, Emily said, "I will take Marcia. She may be more orgasmic, but I'm less skilled in pleasuring a woman. I've used the We/Vibe before and it is very effective on me. Bella hasn't used one but we seem to get off about the same time if we finger one another. I think the most honest contest is one where I take Marcia."

I turned them so they were facing the moist lips of their respective partner, then fastened their cuffs together with a leather strap running below the legs of that person. I lowered their heads until their lips and tongue could reach the spread folds of their partner.

"If you feel the need to use your safe word during your punishment, the punishment on that person will immediately stop but they will suffer some further indignity at a later time. I don't anticipate issues, but you're both new to me. I won't be striking either one of you harder than the other, so if they don't have to use a safe word, you probably don't either, although I know Emily is taking more strokes."

I turned on their vibes and said, "You may begin." I picked up the wide lashed whip that I'd previously used on Brianna and Marcia and began the strokes against the fronts of Bella and Emily. The first few strokes were testing their tolerance to the whip and were of low intensity and against their stomach and legs. They initially flinched, but upon realizing that the pain was easily tolerable, even the flinching ceased as they concentrated on the bare mounds in front of them. As I began to move the strokes up against a mons or down to a breast, I would hear an occasional moan, quickly smothered in the soft folds their lips were buried in.

Not surprisingly to me given Bella's previous experience with women, Brianna climaxed first, but Marcia wasn't far behind and their hips rocked and rolled on the floor as they took their pleasure. Emily flashed a finger first to show her first climax, being used to the Vibe, but Bella followed fairly quickly. By the time I'd reached thirty strokes on each of them, both young women had rivulets of cum running down their flat, tight bellies. The first inch or two of the dildo protruding from each slave on the floor was thick with white cream from their orgasms and a small puddle of their releases was forming on the outdoor carpeting beneath each cleft. I began to concentrate my strokes more on their lovely breasts and nipples and bare mons. Their moans of pleasure and pain both were muffled in the slick folds of their partners.

It was an incredible experience. To think that Bella Hadid and Emily Ratajkowski were both hanging naked before me, tonguing the twats of my other slaves, the pale pink stripes from the whip crisscrossing their thighs, mons, stomach and breasts was almost more than I could bear and my cock was rock hard. When I finally put it in something, it wasn't going to take long before I exploded again. I wasn't trying to keep up with the orgasms of Marcia or Brianna, but I could tell they were both enjoying their partners tongues immensely, their hips in an almost constant motion back and forth on the thick dildo. Emily had flashed her fingers to me 13 times and Bella 12 by the time both had received 50 strokes. I left off Bella and gave Emily her last 10 lashes, all upon her magnificent breasts. She gave me one more finger flash on the 59th stroke.

"Time!" I called as I turned off the Vibes. The two new slaves faces were covered in orgasmic fluids, as were their stomachs. Emily had some dripping off her right breast. I untied the strap around their waists and lowered them to the ground where they gratefully collapsed in both exhaustion and from hanging upside down. I untied Marcia and Brianna, and we all helped them remove their suspension boots. Brianna lapped at their cunts to clean the fluids flowing there as she removed the Vibes. Brianna sure loved her women.

"I have 12 orgasms for Bella and 14 for Emily. Does that agree with your own tallies?"

Bella nodded and Emily said, "I think the last one was almost as much from having my tits lashed as it was the Vibe. I never expected my punishment to feel so good. Thank you, Marcia."

"What's Marcia got to do with it?" I asked.

"She told me that you wanted to punish me and would make sure that I wouldn't last without your permission, so just to go ahead and enjoy it instead of trying to hold back."

I glanced at Marcia who nodded in affirmation. "You know me so well, little slave."

"I do, Master," she said, smiling.

"How many orgasms did you have Marcia?"

"12, Master. I think most of them were after the first 30 strokes. Emily got better and better at satisfying me with practice."

Emily blushed.

"Brianna, how many did you have?"

"Ten, Master. Bella did a wonderful job, but we both know your little slave is a orgasm slut."

"She is, isn't she. It's part of what makes her such a wonderful slave. Let's see; 10-12 is a negative two and 12-14 is also a negative two. You both won, or maybe I should say that you both lost, because now I intend to fuck you both in the ass. Before I do that, I have to release in you, Brianna, because I won't be able to hold out."

She climbed aboard a padded bench and I sank my cock into her hot, tight hole. A half dozen strokes and Brianna claimed another load of sperm for her baby project. I shrank after surrendering my cream and I had Bella, Emily and Marcia clean me with their tongues. Marcia went last because she was so good, she could have me in a state of erection even shortly after cumming.

We put Bella on another padded bench, her ass just resting on the edge and attaching her ankle cuffs to straps that raised her legs up towards her head. I pulled a condom from the box purchased that morning and slid it over my erection.

"Have you ever had an orgasm while being fucked anally, Bella?"

"No, Master. I've had them while penetrated anally with a plug, but never while being fucked."

"I want you to have one while I'm fucking your ass, so I'm going to ask one of the other slaves to pleasure you orally while I'm fucking you. Do you want to do it, little slave?"

"I don't think that I'm quite ready for that, Master."

"You've done everything but, came awful close to it a few times. Are you sure?"

"Not quite ready, Master. I'm not sure I ever will be, but I'm trying to keep an open mind."

"Emily, hop up here and take care of Bella. Just wait until I'm ready."

"Yes, Master." She climbed on top of Bella, her face still sticky from pleasing Marcia.

I removed the plug from Bella's ass and it came out with a soft plop and a whisper of air. I spread a lot of lube on my condom covered cock and around the edge of her anus, still slightly distended from the plug.

"Push it in me, Master. Fuck my ass. Make me cum."

She hissed through her teeth as I followed her instructions and slowly sank my shaft into her dark hole.

"Master, you feel so big back there. Go gently please."

"Of course. Emily, now, lick your friend."

I slid slowly up her ass until my balls nudged against her cheeks, all the while Emily lapped and sucked at her feminine folds and her hard little clit.

I began stroking slowly the length of my prick, back and forth from the tip to the base of my stalk, giving a little extra shove as I reached the base.

"Fuck, that feels better than I remember. You can go harder now."

I increased the pace of my penetration and Bella moaned each time I slammed against her ass.

"It feels like it's in my stomach, it's so deep in me. Fuck me harder, please. Make me cum, Master."

"Your wish is my command," I said slamming harder and faster.

Emily's had two fingers pushed into Bella's cunt and was sucking her clit like there was no tomorrow. Bella's nipples swelled and her breasts flushed and her stomach was fluttering under Emily's breasts.

"I'm going to cum. I'm going to cum while you're fucking me in the ass. This feels incredible, don't stop anything that you're doing, anyone. I'm going to cum. Master, may I cum."

"Cum for me, Bella. Cum with my cock buried in your ass."

"God, yes, I'm cumming."

I could feel her rectum flexing over my cock as Emily could feel her cunt spasming on her fingers. She moaned and thrashed on the table, thrusting her hips upward so much, she almost threw Emily off of her.

She grabbed Emily's head and pulled it from her clit. "Too much, too much, I'm so sensitive right now. Just stop for a minute."

I had slowed down substantially as she climaxed, but I was still pushing my way deep into her bowels with each stroke, letting her come down gradually from her orgasm.

"My God, that was incredible. I'm so sore now, but that was wonderful. I can't believe it," Bella exclaimed.

Emily jumped off her friend, saying, "Me now, it's my turn. I want to feel it too."

"Greedy little slave. You'll get your turn. Brianna's moved off her bench. Lie down over there so that Bella can rest for a minute."

Brianna helped Emily position herself and fastened her legs up as Bella's had been. I looked at Marcia and motioned toward Emily but she silently shook her head no. I nodded. I wasn't going to push her into something that she wasn't ready to do. She'd already done more things this trip than I had expected. Baby steps.

"If you would assist Emily, Brianna, the way that Bella was helped, we can get started."

"Yes, Master." I knew Brianna would revel in showing Emily all the sapphic pleasures she was so good at.

I removed the plug from Emily's pert perfect little ass and put another condom on. I spread lube around thoroughly as this was going to be her first go at anal intercourse. When I was ready, I positioned my cock at her little rosebud and pushed. I got the head part of the way in, and Brianna started working on Emily's clit while she fingered her hungry cunt, gapped open from the long series of orgasms she'd had. Gradually, the sphincter started to part under the steady pressure of my prick and the distracting pleasure Brianna exerted on her clit and the head popped in. I rubbed a little more lube on the stalk and pushed farther into that tight hole.

"Oh, my God. It's so big, I can't believe that something so big is going in there."

"It's not as wide as the plug at it's widest, but it doesn't get smaller as it goes in," I gasped as more and more of my cock was swallowed by her delectable ass. When my balls were resting against those classic ass cheeks, I checked her status.