Dana & Holly Ch. 01

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Sub gets punished for cumming too many times.
7.3k words
4.41
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Part 1 of the 5 part series

Updated 10/26/2022
Created 02/03/2014
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THE WORKOUT

I'd been working out in my gym for about an hour, in the middle of some cool-down stretches, when I was interrupted by my sub, Holly. "I have a gift for you, Mistress Dana," she said playfully. She was right behind me. I opened my eyes and found myself looking straight up her skirt, her panty-covered pussy staring right back at me. Holly was a little minx... supremely naughty fuck pig was more like it... and she love to tease.

A little background on us... My name is Dana. I'm 32 yrs old, brunette, and a retired pro tennis player. I still take care of myself, so I've still got a pretty hard body. I was also very successful on the tour, having won several majors, so money-wise, I'm loaded. I can easily afford to support my little fuck toy, Holly. I can afford to do what I want, and what I wanted when I bought the place, was a play room just for fucking, aka the Romper Room.

Holly, meanwhile, is 23 years old, and is just ridiculously hot. Platinum blonde, long-legged, petite, limber as a gymnast. Her tits were firm and perky, a small C cup (which were big for her frame, but not overly big) with deliciously perfect nipples. Downstairs, she had a tiny little pussy, almost half-size looking, so tight and so delicious. In the back, her ass is meaty and firm, and she has the sweetest tasting asshole that just begs to be pounded. Seriously, it is so eager to be stuffed, whenever I stick a finger in there, I swear it feels like the muscles in her butthole latch on and pull my finger in deeper. So pretty and delicious, I can't get enough of her asshole, kissing, licking, probing, stretching, pounding like it's a new toy at Christmas.

Holly has a sex drive to match her looks. This girl loves to fuck, and loves to fuck nasty. I'm so glad I met her, so glad I can afford her, and so glad I'm in shape enough to keep up with her.

We met by chance while I was on tour. Holly was a massage therapist, had just started working at a local spa, when I stopped in one day on a break between tournaments. She did a good job, and was flirty/friendly, so I came in again the next week and requested her specifically. It didn't take long at all for the flirting to start. Holly is aggressive and hot, and I was feeling receptive and horny. I invited her to my place that weekend. It only took a couple glasses of wine and a couple of hours of small talk before I had this little vixen slurping my cunt like a dog with a bowl of Alpo. She stayed the weekend, we fucked like mad. I even invited over a couple of friends and we turned this girl inside out. At least, we tried to. No matter how many ways we plugged her holes, this little sex beast begged for more.

What's better, not only did she fuck like crazy, she loved to be dominated, and that fit perfectly with my take-charge personality. It wasn't long at all before Holly quit her job and moved in with me to be my own personal plaything, my little plastic fuck doll in the flesh. Our relationship wasn't a hard D/s thing, me guiding her every move like some people do. Rather, our relationship was kinda loose, her having a lot of autonomy to make her own decisions; she has such a wicked imagination, and I love for her to put it to use. When it came time for sex, though, she knew who was in charge – me. Mistress Dana.

So as I was saying, I was lying on the floor, doing some stretches, when Holly walked up and said she had a present for me. She was standing really close to me, on purpose, so that when I looked up at her, I was looking straight up her skirt, with her barely covered pussy right in my grill. She was wearing this bright, baby blue schoolgirl skirt, and a pink-and-white striped micro g-string that had a picture of an ice cream cone on the front. Made for licking, and I was licking my lips. I love it when she wears those micro panties. There's just enough there to barely cover her lips, and you know damn well that that pussy is shaved totally bare.

I looked up her and said, "Thank you, Holly," as she handed it to me with an excited smile. "I wonder what it could be?" As I opened the gift-wrapped box, the smell of juicy pussy hit my nostrils. Yum. Inside the box, there was a stack of photos on top, and something else underneath. I looked at the photos first. The first one showed Holly in bed, wearing the same outfit she had on right now; she must have taken these just a few minutes ago. The next photo was of her masturbating with a vibrator on her clit, and an orgasm on her face. The last photo was a close-up of her pulling a pair of panties out of her pussy. A panty-stuffing. My naughty little sub had just stuffed some panties in her pussy, jerked off all over them, and now she's bringing them to me as a gift. I love this girl.

Looking up, I told her, "I really like it so far, Holly. You always give me the best surprises." That's when I noticed she was wearing a cut-off halter top with plenty of underboob showing, nipples poking out, and little white pom-poms in her pigtail hair. Around her neck was a white spike dog collar, with a leash in her hand. On her feet were some lacey ankle socks and a pair of blue platform Mary Janes. "Oh, yes. School is in session. Naughty bitch is gonna get fucked hard today," I thought to myself with a slight smile. "But doesn't she always?"

Holly giggled a little. "Thank you, Mistress Dana."

I reached in the box again and pulled out the freshly soiled panties. They were white cotton, with the words "I Love You" printed all over them, and they were straight out of her pussy. Moist, sticky, smelly, and straight out of her pussy. I loved it. I held them against my nose and breathed in her scent over and over. So sweet. Standing up and looking her in the eye, I stuffed them in my mouth and sucked on them, sucked on the seam right where her pussy hole would be, right at the source of her nectar. "I love the taste of your pussy, Holly, and they smell delicious, too. You're being very naughty this morning. I bet you need to get fucked. Tell me, how many times did you cum on these panties?"

"Yes, Mistress. I came on them twice." Holly turned around and bent down to pick up my towel, bending at the waist so her ass was in full display. She had a buttplug in her ass, and wanted to make sure that I saw it. Naughty little minx. "I'm feeling very horny today, like a nasty little slut pig. Would you please treat me like one?"

Those words made me shudder. "Oh, I think we can arrange that. The bad little school girl needs some detention." I smacked her ass good, attached the leash to her collar and led her towards the Romper Room.

The Romper Room was the first sex den I had built, and I've been adding to it for years. A giant room, it's got sexual devices and implements of all types – floggers, paddles, cuffs, and spreaders on the wall. Leashes and collars and gags. A giant mirror running the full length of one wall, with a versa-horse and stocks in front of it. A sybian. Rocking dildo. St Andrew's cross. Cage. Sex swing. A cabinet full of dildos, vibrators, buttplugs, and the like. A wardrobe filled with clothing. There were cameras galore, both video and still, because we loved to film ourselves, with three 60" tv's for viewing. With that camera setup, Holly or whomever can look at the screen and watch her asshole getting pounded, live in realtime, HD, and widescreen tv. It was sweet. And in the center of the room was a bed I had built. Circular, 8' in diameter, with restraint points everywhere, so I can tie my guests up and spread them out however I damn well please.

When we got to the Romper Room, I sat Holly on the bed, attached a loose leader from her collar to one of the restraint points, and told her to wait there while I go get ready. I turned on both the tv's, and loaded up some of our sex tapes for her to watch and get worked up by. Both televisions were hooked up to computers, and on one, I loaded up a few videos, and on the other, I loaded up a slideshow of still photos. She could watch tape of us fucking on one, and on the other, photos of her best gapes, and creampies, and every other filthy thing that we do. She was rapt with attention, her hands already roaming over her breasts and thighs. I didn't want her getting out of control while I was gone, so I stepped in front of the tv to get her attention. "I'm going to go clean up now. While I'm gone, you may use one hand, and one hand only, to touch yourself. Understand?"

"Yes, Mistress Dana," she nodded.

"Here," I said, and tossed her a vibrator. "You may use this if you like, but you can only cum one time. If you cum more than once, you will be punished. Understand?" It was a small, unsatisfying vibrator, but that was the point – she's supposed to get worked up, not worn out. "One orgasm only. Any other time you start getting close to orgasm, you have to stop and cool down for twenty seconds. Got it?"

"Yes, Ma'am. One hand only. One orgasm only. Otherwise, I'll be punished. Please hurry back." She was already trying to look around me at the tv, she was so greedy to get it on. I turned around and saw what was on tv: the photo showed her gaped-out ass with her smiling back at the camera, and the video was of me 69ing with a friend that we played with sometimes. There was no way Holly was only going to be able to cum just once. She was in serious heat today, and I loved it.

"Good girl, Holly. Mind your mistress" I told her. I stuck my finger in my dripping cunt for a second, and then wiped it off right under her nose, so she could breathe my scent while I was gone. "Mmm," she replied, tongue snaking out to get a taste as I headed upstairs to shower.

As I was headed upstairs, sniffing and licking her panties some more, I got an inspiration of what I could do with them. Still being really sweaty from my workout, I rubbed her panties all over me to wipe myself down and get my sweat mixed in with her juices. My pussy was soaking wet, too, with juices running down my legs, so that got wiped up, too. Thinking about her creamy, tiny, bare pussy and puckered little bunghole got me drooling a little bit. I made sure to wipe my spit on the panties, too. "She's gonna get it all," I thought, making my way across the house.

Up in my bedroom, I called my friend, Teri, to come get in on the action. Teri was a couple years younger than me, a redhead with massive EE tits, aggressive, and she had a sweet spot for Holly. Lucky for me (and Teri, and Holly), she had just finished some errands, and would be over in an hour. "Can't wait," I responded. "Just let yourself in. We'll be down in the Romper Room."

I hung up the phone, and climbed on the bed to prepare the next part of my plan for Holly's panties. Since my pussy was already soaking wet with anticipation, I did a panty-stuffing of my own. I stuffed Holly's soiled panties in my pussy and rubbed a quick one out for myself, and came all over them. I used those panties to sop up every bit of sweat and cum my body produced. I wanted Holly to taste it all. Besides, I really needed to get off a quick one, just to break the tension.

After a quick shower, I toweled off and went downstairs, still naked, to go check on Holly. She was sitting on the edge of the bed when I entered. Her clothes tossed aside, nothing on but her socks, she was rubbing the vibe on the under-curve of her left breast, giving her clit a cool-down. "Are you back, Mistress?" she asked excitedly.

"Yes, pet, but Mistress still has to get dressed." I grabbed a serving cart and walked to the cabinet loaded with all my dildos and stuff. Sorting through the drawers, I started laying things out on the cart for us to play with. A soft rubber prostate massager with a long shaft and bulb tip on one end, and a sword handle on the other. A glass plug with a ball-shaped head. A 15" purple double dildo. A bullet vibe. A string of pink, one-inch diameter beads. A hand-held clit pump. Nipple suckers. A black leather paddle. Two separate strap-ons, one for me and one for Teri. The one I liked to use was 8" long, two inches thick, and yellow with ruler marks so I could see how deep I had it stuffed in Holly's hole. Teri's was a replica of some black pornstar, all long and thick (I told you she was aggressive). And then of course, I put Holly's soiled panties on the tray.

,I wheeled the cart out so Holly could see what we were going to play with (the better to tease her with). I massaged her tits for a moment, ran my fingers across the nipples, and then applied the nipple suckers to get them puckered up. I then went over to the wardrobe to get dressed. While putting on a black corset and black stockings, I could hear Holly moving around behind me. "What is she up to?" I wondered.

As I got the stockings pulled up, I turned around and saw Holly on her knees, face down, with two fingers in her ass up to the knuckle. I could hear the vibrator, but couldn't see it. Walking around in front of her, I asked her where the vibe was. She turned her ass to me, pointed to her pussy, and said, "In there." I spread her lips and saw the white end peeking out. The little beast had stuffed that vibrator all the way inside her pussy! And was finger-banging the hell out of her ass. "Gawd," I thought in amazement. "The girl knows how to make the most of what she's got." I was a proud mistress. Still, though, I needed to be stern.

"Give me that!" I exclaimed, plunging my fingers in her cunt and yanking out the slimy, buzzing vibrator. "How many times have you cum?" I asked forcibly, waving the vibrator in her face. She was sitting up now. "Twice, Mistress. I'm sorry. I tried really hard to not to cum that second time, but I just couldn't hold it." I stuck the vibe in her mouth for her to suck clean, and then I tossed it aside. "You're in trouble now," I said, undoing her leash. "A simple instruction like that and you just can't listen." I pushed Holly onto her back in the middle of the bed, stretched her arms out to either side, and tied them down. Then I rolled her ass up into the air over her head. A piledriver, they call it, her ass straight up in the air, legs back over her head, and both her sweet holes displayed for my use. I put ankle cuffs on her, and then tied those off, too. This bitch was going nowhere.

I switch the input on the tv from playback to live feed. The image switched to Holly tied to the bed, legs and arms pinned back, ass straight up in the air. I hit the record button. Our every move was being played back in real time for us to watch now, and also recorded for us to watch again later. I had to turn the volume down, though, so we wouldn't get feedback. These videos were our entertainment, so everything had to be just right.

"Now then. Time for School Girl to get fucked!" I climbed up behind her and spread her cheeks. She wiggled her hips in anticipation. I gave her pink butthole a few good licks and slurps. "You're all tied up right now. I can do what I please, can't I?"

"Yes, Ma'am."

"And what are you going to do about it?"

"Lie here and take it."

"That's right, whore," I said aggressivley, with a smack on her ass, followed by a lick. "Who's slutty asshole is this?" I gave it a tug.

"Your slutty asshole, Mistress."

I spread her pussy lips a little with one hand, and ran my index finger of the other hand across her moist, pink slit. Her pretty pink pearl was swollen and staring back at me. "And who's slutty pussy is this?"

"Your slutty pussy, Mistress. All yours, forever and ever."

"You're just a little blow-up fuck doll, aren't you?"

"Yes, Mistress. I'm your little fuck doll. Please abuse me."

My pussy pulsed, just hearing her, the nasty slut. "Yes, I will," I greedily said to myself. I slipped a finger from both hands into her asshole and gave it a little stretch. I love playing with this asshole. "And I haven't forgotten your disobedience," I said angrily, giving her ass three good smacks with the paddle. Her ass turned a nice little red. Getting up, I fetched the sword-handled ass toy and lubed it up. "Here we go," I said, pressing the bulb tip against her bung. Holly took a sharp breath and a smile as the tip stretched her butthole and was forced inside. I worked the tip in and out a few times, watching as her tight, little asshole stretched around it, then snapped shut again. Then I worked it in a little deeper. There was some pussy cream leaking out and coating her thigh. "I wonder how far I can shove this in there," I asked, shoving it in deeper until Holly gave a grunt. "Oooh. Almost to the end." It was in there nearly seven inches.

"Thank you, Mistress Dana." She wiggled her butt in appreciation.

It was time for some pussy play. I slipped a finger from each hand into her dripping cunt and stretched that pussy w-i-d-e. "Nngh," was all I heard. I looked at that stretched hole and shoved my tongue deep inside, licking up, down, and all around. I lapped up her delicious juices as she cooed. From the serving tray, I grabbed the clit pump and the bullet vibe. When I came back to the bed, I climbed around to her front, so I could get better access to her pussy. First, I put the pump on her clit and gave it a few squeezes, watching it swell. Then I took the pump off her clit and replaced it with the bullet, vibrating the sensitive thing. "You disobeyed me earlier. You came twice, when I told you only once, didn't you, slut?"

"Yes, Mistress."

"Well, no more. You only cum when I allow you, understand?"

"Yes, Mistress."

"Whenever you want to cum, you're going to ask me proper."

"Yes, Ma'am."

"And you're gonna hold it until I say so. Is that clear?"

"Yes, Ma'am."

"Is that clear?" I said angrily, swatting her pussy.

"Yes, Mistress Dana," she exclaimed.

"Good," I told her, and went back to alternating between the clit pump and the vibe. After a couple minutes, she started getting really close. "Please, Mistress, may I come now?" she asked. "No," I told her loudly. "You hold it. You be a big girl and you hold it."

Her whole pussy was getting puffed up. I had to have a taste. I put the toys down, spread those lips wide, and slurped those juices up, making loud noises as I did so. The juices were flowing like a river, going uphill and straight into my mouth. I stuck my tongue repeatedly into her hole, scooping out all the deliciousness I could get. I pursed my lips and sucked on her clit. It was so large and red now. "Pleeeaase, Mistress," she pleaded. "It's getting so hard. I need to cum for you."

"Ten seconds," I instructed her. "Count to ten, and then you can cum." I vacuum-locked my mouth on her hole, slurping and licking, waiting for my prize, and gave that buttplug a few tugs back and forth. Ten quick seconds later, I heard her grunt and shiver as she released, the juices flowing straight into my mouth. So delicious! One day, I'm gonna bottle it up, freeze it, and make me a pussy popsicle.

After her orgasm subsided, I got down and kissed her, my mouth sloppy with her cum. I held my tongue in her mouth for a long time, letting her swirl hers around it to suck up as much of her flavor as she could. "Good slut," I praised her, and kissed her again. "You made your mistress proud." She was beaming.

"Thank you, Mistress." She loved to please me.

"Would you like to lick my pussy now?" I asked her.

"Yes, please, Mistress. I've been waiting all day."

I pulled the dildo out of her ass and looked on the tray for a new toy. I started to reach for the double header, because I loved the way Holly looked with half of it up her ass, and the other half hanging out like a tail. But instead, I grabbed the bullet vibe. This was a vibrator day. Settling down to straddle her face, I stuck the vibe in her stinkhole, and then pushed in deeper with my finger. Holly grunted in approval. "Thank you, Mistress Dana."

With a handheld camera in my hand, I looked her in the eye to record her every reaction. One of my favorite parts of our movies is when I watch her eyes while she licks my holes. "You wanna lick my pussy, little girl?" I asked, holding my pussy just a couple inches from her face. She could smell it. A drop of my cum dripped onto her lip, and her tongue whipped out in a flash to lap it up. "Very much, Mistress Dana. I love your pussy. May I please have it?"

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