Miss Pamela Twelve

Mistress awakened me with a firm squeeze of my balls. She'd had me report to her after I took Gloria home the night before. When I stripped and presented, she explored my body carefully, particularly my genitals and anus. She quizzed me about what I'd experienced with Gloria. The ball flogging intrigued her, particularly the reason Gloria had relented. She fondled my balls thoroughly and painfully as she interrogated me.

"So you two have settled on a vanilla relationship going forward?"

"I think it's more like a fluid situation that can change according to current mood shifts."

"Interesting. Do you enjoy sex with her."

"Yes, Mistress."

"And what about Lisa?"

"I enjoy her very much, Mistress."

"I find the dynamic between you two fascinating. The way she came when you flogged her pussy was very exciting."

"It certainly was, Mistress."

"You enjoyed hurting her."

I nodded.

"My slave is a switch."

"Yes, Mistress, I guess I am."

"I spoke with her about your relationship."

"Yes, Mistress?"

"She is also very much a switch at heart, and I encouraged her to fully explore all aspects of your dynamic."

"Thank you, Mistress."

"She's madly in love with you."

I nodded again accompanying it with a shy smile.

"All I ask is that you treat her well and use her lovingly. Pretty much what I told her about you."

"Thank you very much, Mistress."

After I climbed out of bed and showered, I reported to Mistress for her morning worship, which as usual was very pleasurable for both of us. I so adore everything about eating Mistress perfect pussy.

"Do you need to work today?"

"Yes, Mistress. I'm beginning work on a new board for Lisa, as a matter of fact."

"Excellent, a labor of love."

I blushed and nodded.

"Make her a great board. I'll see you tonight."

She gave my balls a final squeeze.

"Yes, Mistress, thank you."

When I got to my shop, I was glad to see that Lisa was already there. She saw me drive up and hopped out of her car to greet me with a happy kiss. She wore a pink tank top and denim cutoffs that showed off her attributes alluringly in a casual, understated way. Her tousled blonde hair and gamine cuteness inspired a rising tumescence in my board shorts.

Once inside the shop she turned me to face her and thrust her hand inside the waistband of my shorts, taking my cock in hand and whispered huskily, "You're mine today."

"Okay."

"Okay what, slut?"

"Okay, Miss?"

"Better."

She squeezed my balls firmly and I yelped.

"Very tender, eh? Did Gloria hurt these babies last night?"

"Yes, Miss."

She squeezed a little harder wrenching a high-pitched cry from me.

"Go out to my car, you'll find a bag on the passenger seat, fetch it for me."

"Yes, Miss."

She released my jewels, removed her hand from my shorts and swatted my butt. I hastened to her car where I found a plain, white shopping bag. I returned to place it by her feet.

"Strip and present."

I obeyed snapping into the expected pose with my hands behind my head, legs spread to shoulder width, and my hips thrust forward to present my goodies.

"Good boy."

"Thank you, Miss."

"Are you ready to serve me today."

"Yes, Miss."

She grabbed my balls in a tight grasp, squeezing and giving them a twist.

"Did you peek in the bag?"

"No, Miss."

"Good. I visited Desiree's shop before I came here. She was amused that I was there to find implements to use on you today. She gave me some advice that will make this more fun, at least for me. She's deliciously wicked, isn't she?"

"Yes, Miss, she is that."

Lisa laughed and picked up the bag, reached into it, and withdrew a fierce looking flogger with a dildo handle. She swished the tresses with a dark evil smile.

I'm sure I winced at the sight.

"This looks like fun, don't you think?"

"Yes, Miss," I said with obvious lack of conviction.

She placed the glans of the realistic looking cock to my lips and raised an eyebrow until I opened my mouth to accept it.

"Hold on to that until we need it."

The next item to emerge from the bag was a strap on rig, replete with a very large realistic cock which she slipped on immediately.

"As I recall you love getting fucked, don't you bitch boy?"

"Yes, Miss."

"And I love fucking you, so today will be a win win."

"I selected a nice-looking dildo for this, but Desiree insisted that I take this one instead because it's a bit longer and thicker. She assured me it would be a better fit to break you in with."

"Gulp"

Next, she extracted a set of clover clamps connected by an eight-inch chain that she flexed open and shut provocatively in front of my face before hanging them around the back of my neck. She leaned close to tease my nipples, first flicking them with her fingernails, then squeezing them between her thumbs and index fingers, and finally pinching them harshly with her fingernails. I whimpered in response. She bent closer still taking first one then the other in her mouth to relieve some of the sting, suckling and licking them, but then biting down harshly. I cried out at these new indignities.

She cupped my balls and squeezed as she punished my nipples with her teeth. I struggled to remain still despite the pain she was inflicting. To amplify my discomfort, she tugged my balls down hard and twisted. Tears welled in my eyes. She smiled wickedly, obviously enjoying her power and my subservience.

Letting go of my balls, she grasped my chin, forcing my lips to purse and she kissed me fiercely.

"You know I love you, Tommy."

I nodded as tears rolled down my cheeks.

She pinched my left nipple forcing it out so she could snap on a clover clamp making me whimper, then repeated the process on the right one. My knees buckled momentarily. A hard yank on the connecting chain drew a scream, forcing her to catch the dildo flogger handle as it slipped from my mouth.

"Are you okay, baby?"

"Yes, Miss, I love you too."

She pulled down on the clover chain until I was kneeling before her, the fat vinyl cock almost touching my lips, so I kissed the glans.

"You can do better than that, can't you?"

I took the phallus into my mouth and began to suck it. She stroked my head, gradually pressing me forward to take the entire cock, gagging me.

"Take it all, bitch."

I backed off enough to regather myself and then opened wider and repositioned a bit to accept the entire cock.

"You look really hot down there."

I fondled the realistic looking pair of balls dangling beneath her cock.

She grabbed a handful of my hair, pulled and tilted my head back so she could stare into my eyes.

"You like sucking my cock, don't you?'

"Yes, Miss.

Lisa reached into the bag and found a tube of lube which she handed to me.

"I bet you know what to do with this."

I opened the tube and dribbled a generous stream onto the cock jutting from her harness, then added some to my fingers, reached behind myself and smeared it into my crack.

"Get plenty in there this cock is bigger."

I could tell when I lubed it that would be the biggest I had ever been fucked with.

"You want me to fuck you, don't you?"

"Yes, Miss, but please be gentle, that thing's huge."

"Desi picked it out specially for you. She knew where it was going."

"Yes, Miss, I know."

"We'll both be proud of you when you take it."

She took hold of the clovers' chain to lead me to the mattress I kept in the corner. It felt like twin lightning bolts striking my chest.

"All fours."

I obeyed and positioned myself as she directed.

Lisa reminded me she had the flogger by initiating a figure eight stroke stinging fiercely on my upraised butt. The leather bit sharply into my buttocks, then she switched axis for a few strokes making the tresses bite wickedly into my balls and cock.

"Do you think you could cum from that like I did? Shall we find out?"

"No please, Miss."

"No?"

"Please, they're already so sore."

"Because you let that Gloria woman beat them. I bet you didn't tell her no, did you?"

"No, Miss."

"So, you can take it for her but not for me. That's disappointing."

I sighed resignedly, "Just please be merciful, they already ache so bad."

She laughed, "I guess I'm tougher than you are."

"Yes, Miss, you are."

She gave me three more excruciating strokes before laying the flogger down on the mattress in front of me, presumably taunting me with its ongoing promise of pain.

I felt her kneel behind me on the mattress, sliding her knees between my calves, pressing them farther apart. Her cock brushed my aching balls as she settled in to position. She moved the realistic glans into my cleft and pressed it against my anus.

"Tell me what you want, baby."

"I want you to fuck me, Miss."

"Do you need it?"

"Yes, Miss, I need your big dick in my ass, please fuck me."

The pressure increased as she began to push harder. I pushed back, knowing it would help her to get in and make it less painful for me."

She clasped my hips in a powerful grip and thrust forcefully. I howled as the massive knob burst past my sphincter and drove deep into my rectum. Lisa continued pressing until it was fully embedded in me. The fiery explosion of pain felt as though I had been torn apart. She held off for a bit, staying still and letting me recover from the searing pain before she began thrusting in and out.

My breathing was labored. I tried not to move yet, knowing that the pain would pass.

"Are you okay?"

"Yes, Miss."

She stroked my buttock.

"The pain is fading."

"Is it only pain?"

"No, Miss, it feels good being so full with your cock, possessed by you."

"I like that. I felt like that when you fucked both of my holes."

"I'm glad."

She began to move her cock inside me, small moves still, but the movement stirred my arousal immediately. The gentle pressure from the huge cock on my prostate was exquisite.

With superb patience she made each stroke minutely longer. The slow build expanded my arousal exponentially and soon I felt thrilling sensations like mini climaxes with each stroke. She cupped my balls with one hand and gripped my cock with her other working them in unison with the cock she was now beginning to thrust with purpose inside my rectum. I began pressing back to amplify the effect of her ramrod reaming me.

"That's it, fuck me, baby. Make me your bitch."

That inspired Lisa to increase the speed, power, and length of her strokes as she pounded my ass ruthlessly with her massive cock.

"Damn it's hot fucking you like this. I love you, baby."

She was working my glans with her thumb and rolling my balls in her other hand as she pumped my aching hole. The combination of stimuli was making my head swim. I knew the mother of all orgasms was building and about to explode.

"Please, Miss, may I cum?"

"Yes, baby cum for me."

And did I ever, powerfully ejaculating thick ropes of cum six times, then oozing slowly, forever it seemed, while a marvelous shuddering body high shook me. Lisa's gentle touch helped prolong that delicious sensation.

She rolled me over so she could kiss me. Our mouths locked together in a blistering meeting of hearts and souls. I pushed her onto her back, unhooked her harness and dove face first between her legs.

Her pussy was sopping wet and welling up a generous supply of her spectacular secretions. Her instant reaction as my tongue separated her curtains and dove into her hot tunnel told me that she was right on the edge of her own massive pleasure bomb. The first firm tongue stroke on her swollen fuck button was the trigger and she came screaming in ecstasy, shaking, almost convulsing.

I drank greedily of her woman wine, savoring her delicious passion as she drifted happily in her sea of sweet sensation. She got to the hypersensitive post-orgasmic place and pushed me away. Her hand brushed a clover, sending a shock through my chest.

"I forgot you still had those on."

"Yeah."

She fumbled with them trying to get them off. That hurt a lot, but when she opened and removed them, the agonizing return of blood flow made me scream. She leaned over to tenderly suckle my throbbing nipples in an effort to ameliorate my suffering. I stroked her hair and kissed the top of her head.

"That was amazing, Lisa."

"I really love fucking you, it's so hot turning the tables. We sure fill all of each other's needs."

I kissed her deeply and she responded in kind. I leaned down to take a swollen nipple in my mouth, sucked it to feel it harden even more in my mouth. I teased it with my teeth, nipping it, pulling it. She whimpered at the small pain and clutched my head to her.

I switched nipples and repeated the attention, delighting in the needy sounds she was making. I gave her one harder bite, switched back to the other nipple, then leaned back to flash a wicked smile.

""My turn."

"Please don't hurt me."

I laughed wickedly as I picked the clovers up from the mattress. Her eyes widened as I brandished them near her face.

"Please, Master, those things hurt so much."

"Gee, I didn't know that."

We shared a laugh, hers rueful and mine wicked. I brushed her rock-hard nipples with them, making her shiver fearfully.

I opened both of the clovers wide and held them surrounding her nipples while I stared into her wide open, fearful eyes. I smiled. She trembled. I released the left one suddenly. She howled. Her breath came quickly, panting in anticipation of the next clover's imminent closure. Instead, I took that nipple in my mouth, suckling it seductively before kissing my way down her taut athlete's belly until I came to her lovely labia. Her pouting pussy curtains glistened with her juices. I licked the pink flesh, tasting her arousal and savoring her heat.

I spread her folds with my left hand, to reveal her beautifully exposed and swollen pearl. I teased it with my tongue tip. She moaned and thrust herself up to meet my mouth, but when I brought the open clover up to surround her clit, she shrank back trying to protect herself from this new threat of agony. I teased her as she squirmed by opening and closing the jaws of the clamp around her clit. With each opening and closing cycle I let the closures be a little more aggressive.

I could smell her fear. Despite having cum so recently my cock was fully erect. Blood lust inspired by her terror. The dynamic between us with its quickly shifting nature was exquisite.

I backed off the clover from her clit and leaned in to lick her again. This time I worked her more intensely. As her arousal built, I cultivated it carefully. She was pushing and rocking her hips. When it felt like she was about to cum I brought the clover back into position and let it snap closed on her swollen fuck button.

"Aaiiiiyyeh."

Her scream was nearly musical, traversing two octaves.

I shifted position to cover her mouth with mine, plunging my tongue into her. It let me swallow her agony and feed off her amazing reaction to the pain she must be suffering. Tears flowed from her eyes. I kissed them, tasting their salt.

"I do love you, Lisa."

She struggled to control her sobs and choked out, "I love you Master."

I teased the clover biting into her clit, subtly, gently. She whimpered at the motion.

All the movements were infinitesimal, but each got a reaction.

"Do you think you could cum from this?"

Her eyes flashed horror at the suggestion and she shook her head violently.

"God, no, please stop moving it, please."

"I think you're selling yourself short."

"Please, Master."

I leaned down, inches from her trapped clit and blew gently on it.

"There, doesn't that feel good?"

"Oooh, yes, Master."

I continued the stream of breath a tiny bit firmer and added the gentlest possible tweaks, eliciting a growing blend of whimpers coupled with shudders and moans. Her face was beginning to flush. She touched my arm delicately with her trembling fingertips. Her breathing changed from gasps to long inhales followed by shuddering exhalations. The gradual build was working.

When I increased the amplitude and pace of the clover movements, oscillating and twisting it, her arousal grew more obvious.

"That's it, baby. You can do it."

"Oh my God, Master."

Her thighs began drawing together and her buttocks clenched. I smiled happily as I watched her beginning to cum from the manipulations as the pain began to fully morph into ecstasy.

"Master, may I cum?"

"Yes, baby, cum for me."

And did she ever? screaming out delirious with delight. Her body quivered, her hands clenched, and her abs rippled while three distinct spasms shook through her core.

I released the clover and let her relax. Watching her face was delightful. The post orgasmic peace that brought a peaceful glow to her lovely features was transcendent.

I leaned over her and gave her a gentle kiss before whispering in her ear, "I love you, my beautiful Lisa."

I'm not sure she heard me. I realized that she had slipped into a deep sub space endorphin high, so I simply lay next to her and softly put a protective arm over her.

It was nearly five minutes before she came down and returned to full awareness.

"Did you have a nice flight?"

"It wasn't black velvet. It was bright red."

"Is that unusual?"

"First time."

"Did it feel different?"

"Usually sub space is like being surrounded by black velvet for me, a couple of times it's been green and super peaceful. This was red and angry, a violent feeling. I think maybe because there was so much pain that triggered it."

"Was it bad?"

"It was intense, but I liked it, I guess."

"Not sure?"

"It was incredible, but my clit still aches so much."

"My ass still aches a lot."

"But you liked me fucking you, you came."

"Oh yeah."

"We're quite a pair, aren't we?"

"I like that."

"What?"

"Being a pair with you."

A warm smile bloomed on my face as I leaned in to kiss her softly. She stroked my cheek and returned my gentle kiss.

We lay there holding each other for a while. The peaceful affection was wonderful aftercare for both of us. She felt perfect in my arms, curled against me, soft and trusting.

"We should think about working on your board."

"This feels too good to stop."

"I know."

"A few more minutes, please."

"Okay," and I hugged her closer as she snuggled into my embrace.

We must have shared a short nap, because I noticed the sun was no longer streaming through the windows and Lisa was asleep in my arms. I kissed her cheek and disentangled myself carefully on my way to the refrigerator. Ice cold red Gatorade nearly jumped into my hand. I uncapped it, took a long drink and returned to the mattress. Lisa looked too lovely to disturb, so I capped the bottle and left it on the floor next to her.

My drafting table stands against the far wall. I organized a fresh sheet of paper and tools so we could begin sketching. I also grabbed a catalog of my commercial designs from the shelf to use as a starting point.

When I started moving fiberglass blanks in the storage area, I must have made enough noise to wake her.

"Is this for me?"

She held up the Gatorade bottle.

"Yep."

"What are you up to?"

"Getting stuff organized for us to work on your board."

"Oh yeah, that's why we're here, isn't it?'

"In theory."

We shared a laugh. She got up and wandered over to meet me at the blanks stock.

"You want a shortboard, right."

"Yeah, I think so, nice and maneuverable."

"That's your main concern?"

"I've been trying to learn some flashy tricks."

"About six feet?"

"The one I have is five-ten."

"You handled it really well the other day."

"Thanks."

"Tiny bit more length might help in bigger surf."

"You're the expert. I'll put myself in your hands."

She accompanied the double entendre with an innocent bat of her eyelashes.