Miss Pamela Eleven

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Mistress hosts an orgy, Tommy is used hard and surprised.
3.5k words
4.43
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Part 9 of the 15 part series

Updated 01/17/2024
Created 08/18/2023
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When Gloria and I entered Mistress' apartment we encountered a wild scene. Mistress and Desiree were seated on the sofa with Genevieve's two subs eagerly feeding on their pussies. Genevieve was similarly hosting Lisa's voracious attention.

"Join the fun," Mistress called out and beckoned us with the crook of her index finger. She handed Gloria the thong tressed flogger.

"I think you'll find he responds well to this delightful implement."

Gloria cast me a questioning look. I shrugged with a sheepish grin and subtle nod.

Her smile was puzzled, but she trailed the tresses across my cock, and it turned broader as she watched it harden appreciably under the leather's caress. that emboldened her to flick me with it. I responded by thrusting my hips forward to meet the lash and she delivered another, firmer stroke.

"See," Mistress winked at her.

Gloria reached down with her free hand to stroke me, balls first then sliding her fingers up across the underside of my cock.

"He enjoys a strong hand and firm use. Don't you, slave?"

"Yes, Mistress."

"Would you like your friend Gloria to use you more?"

"Yes, please, Mistress."

"Have at it, sweetie. You have permission to use him however you'd like whenever he's available. No scat or permanent damage, otherwise have fun."

"Thank you very much."

"Feel free to use the bedroom over there," she gestured to the door.

Empowered by Mistress' invitation, Gloria grabbed my rigid cock and led me toward the bedroom. Desiree winked at me when we passed her.

Inside the bedroom Gloria adapted to the Domme role immediately, lying on the bed, spreading her legs and gesturing to her pussy.

"Eat me, Tommy."

I was happy to oblige and crawled between her legs, quickly bringing my lips to her gorgeous pussy. As my tongue began to separate her folds the first slashing stroke of the flogger bit into my ass. Gloria was definitely getting into it as slashing strokes rained onto my buttocks with the tips of the thong tresses biting into my scrotum.

"Get your tongue in there, deep."

I stiffened my tongue and drove it into her as strongly as I could. She gave me plenty of honey for my efforts and increased her flogging. The stinging pain was inspiring both of us. I was surprised by how much inflicting pain on me seemed to arouse her, making her pussy flow copiously, and that increased my enjoyment of what was always a joy for me.

I shifted my attention to her now extremely swollen clit and she responded with appreciative moans and furious slashes with the flogger. The tips were now biting fiercely into my scrotum regularly.

"That's it, work my clit."

I sucked it into my mouth hard and worked it with my tongue while I cupped her butt to raise her to my mouth. She pulled my head into her aggressively and flogged harder still while I dry humped the bedding. Her arousal was working up to a crescendo encouraging me to work her clit more intently. She clutched my head hard, her thighs clenched and her orgasm swept through her.

The relentless flogging eased as she came forcefully. Her whole body shook as she bucked against me and I thrust my engorged cock into the bedding. I could feel my cum boiling in my balls, ready to fire. Her aftershock spasms continued for over a minute and my last thrust brought my release. I pumped multiple shots of cum that pooled on the bed swallowing my cock in warm wetness and her nectar flowed sweetly from her welling hole for me to drink delightedly.

I indulged gratefully at the fountain of her feminine bounty as long as she allowed before pushing my head away.

"You are very talented, slave."

"Thank you, Ma'am."

"I think I prefer Miss Gloria when we are alone. Of course, never in front of Travis."

"Of course, Miss Gloria."

"I'm getting to like this Domme business. You do respond well to the flogger, as your Mistress said you would. Does it hurt."

"Yes, Miss Gloria."

"Does it excite you when I hurt you?"

"Yes, Miss Gloria."

"It excites me, too."

"I could tell."

"I'd like to explore that more."

"As you wish, Miss Gloria. My job is to serve your pleasure."

"Mmm. Roll onto your back."

I did as instructed presenting my cum slick cock and balls for her view.

"You really enjoyed that a lot it seems."

She drew her fingers through the pool of my cum that was seeping into the bedding and brought them first to her lips for a small taste, then to mine where she inserted them between my lips.

"Clean your mess, slave."

"Yes, Miss Gloria, thank you."

She stroked my cum coated cock, collecting a palm full of semen and brought that to my face where she smeared it across my mouth.

"Thank you, Miss Gloria."

"Yes, I am enjoying this a lot, slave. Genevieve was right. How about you?"

"Very much, Miss Gloria, you're a natural."

She giggled, smiling happily and trailed the flogger across my genitals. She gave me a wicked look, arching an eyebrow and admiring the caress of leather against my flesh.

"May I whip you there?"

"You don't need to ask, Miss Gloria. Mistress gave you permission. You have license to use me any way you please."

"That would hurt a lot, wouldn't it?"

"Very much, Miss Gloria."

Her expression told me that the idea was exciting her and I shivered in response. She stroked her fingernails across my scrotum and along the underside of my stiffening cock.

"Such a lovely cock."

"Thank you, Miss Gloria."

She cupped my balls, wrapped her fingertips underneath digging her nails into my shaft and squeezed hard. I yelped, my wide eyes staring fearfully into hers. She studied my eyes as I whimpered under her cruel grasp.

"Mmm, so lovely, such a turn on."

She shifted her grip to dig her nails into my scrotum and lifted my balls, stretching them painfully away and letting her nails dig in harshly. Bright glints of excitation fired in her lovely eyes. I yelped. She relented and let my balls sag back so she could resume beating me with the flogger.

The first flick of her wrist startled me with sharp stinging pain as the tresses cut into my junk. She began spinning the cruel thongs delivering a rapid series of impacts. I cried out at the newly harsh pain. Her eyes sparkled with excitement and delight at my suffering.

The clear delight on her face heightened the agony I was feeling at her harsh abuse of my tender jewels. Tears began to well in my eyes and she began to giggle. The dynamic was intense between us as the true Domme blossomed in Gloria.

She increased the force of her strikes. The pain in my balls exploded and I cried out in agony. For a few strokes this fed her fury and she beat me harder still making me howl in pain before she suddenly stopped. Her expression changed abruptly to concern,

"Oh my God, I'm sorry. I didn't mean to hurt you that much."

She tossed the flogger away and bent over me, threw her arms around me and kissed my face.

"God Tommy, I'm sorry."

I returned her hug.

"It's okay."

"No, it's not, that's not me, I never meant to..."

"It's really alright, that's what I signed up for."

I kissed her softly as she began to weep. She began kissing her way down my torso, paused for a moment to suckle both nipples and then proceeded down to my genitals. She kissed my cock reverently then shifted to my scrotum, kissing my balls as soft as a feather and murmuring apologies.

"I love your beautiful cock and your wonderful balls. I'm ashamed that I was enjoying hurting them. You've given me so much pleasure and I hurt you happily. I don't know what got into me, I'm so sorry."

I raised her face to mine and kissed her, tenderly at first, then deeply and with growing passion as she responded with her own heat. I cupped her soaked pussy, slipping a finger into her. She ground against my hand, oozing sweet nectar into my palm and devouring my tongue. She reached for my cock, gripped it tightly and tried to guide me toward her opening. I removed my finger and let her guide me toward her steamy snatch. She straddled me, sheathing my cock with her sex and began pumping up and down, posting on me, clenching and unclenching her muscles around me. It was a magnificent milking she was giving me as she kissed my face and professed her sorrow for hurting me and her devotion to my 'amazing' cock.

Her wonderful, womanly breasts bounced as she pumped up and down on me. I took them in my hands, manipulating her thick nipples with my thumb and squeezing the firm full globes in my fingers and palms. I squeezed them very firmly and she pressed them into my grasp. For a mature woman with a kid they were delightfully firm and perky. She reached out to pull one from my hand bent over and held it to my face, pressing the nipple into my mouth. I sucked it aggressively while teasing it with my tongue. It swelled delightfully at my attention. I took it in my teeth, nipping lightly. She moaned.

"Bite me."

I gave her a harder bite.

"Aahh, yes that's good. harder."

I increased the pressure, and she yelped.

"Harder, Tommy, really bite me hard."

I clamped down seriously and she cried out from the serious pain although she continued pressing it into my mouth.

She finally pulled away, panting and rubbing the tortured flesh, but leaned forward offering her other nipple.

"Bite this one like that."

I clamped down.

"Harder, really hurt me."

So i did until she screamed, "ENOUGH."

I released her immediately and kissed the tormented flesh tenderly.

"That feels better, thank you."

"You're welcome. Are we even now?"

I laughed and she scoffed.

"Did you enjoy hurting me?"

"Yeah, kinda did. Did you enjoy hurting me?"

"For a while, but then it felt mean and got ugly."

"Fine lines abound when you're doing S&m with people you like."

"I think I get it."

"Cruel can be really hot, but mean changes it to something that's not lovemaking."

"When I was beating your balls it didn't feel like love at all after a bit. I think I might have been channeling feelings for my ex."

"There was a guy named Jack Jackson who used to be the President of the Eulenspiegel Society. He said something really true, "If ain't sensual and mutual, it ain't S&m."

"Wow, I get that. If you keep it loving, it's not what most people think is wrong about it."

"Yeah."

"I have to tell Genevieve that one, I think she'll really like it."

I began to rock my hips and thrust up into her with my still mostly erect cock. She responded immediately and soon we were fucking in a frenzy. She circled her hips on every downstroke, grinding her clit against my pelvis. Her passion built as our union filled the room with slurping sounds as she bounced on my cock like she was riding a pogo stick.

When at last she came, crying out and clutching me through a series of convulsive spasms, before collapsing in my arms. I stroked her tenderly as she wept in exhaustion.

I stroked her hair and she turned her face up to me showing exhaustion and utter vulnerability. She exuded a beatific childlike quality that rent my heart.

It was impossible in that moment not to kiss her with loving tenderness.

"I love you, Tommy."

"Sweet Gloria, this has been some day."

"I'm so glad we really found each other."

"So am I."

A soft knock came at the door.

"Come in."

The door opened and Genevieve stepped in. Her tousled brown curls framed her lovely face and her graceful athletic body compelled admiration.

"How are you kids doing?"

"Fine Gwen, amazing really. You were so right."

"I'm glad you had fun, you needed it. Anyway I'm heading out with my sluts, do you need a ride?"

"I told Harold he could have Travis for an extra night. He was too happy to ask why."

"So, you're good to get home?"

She looked to me and I nodded.

"Sure."

"Nice to meet you, Tommy."

"Likewise, Miss Genevieve, later."

"Hope so."

There was wicked promise in her eyes.

"Me too."

She winked at me with a knowing smile.

"Have fun Glory."

She left and Gloria snuggled into my embrace. She let her hand drift down to my crotch, softly taking hold of my cock and beginning to stroke me.

"You have such a beautiful cock."

I began responding to her attention, hardening in steps, until I was soon rock hard again in her hand. She leaned over and began nuzzling my proud meat, kissing and stroking. She took my glans in her lips and teased the rosy flesh with her tongue, tickling the slit and swirling around my corona. With a feather like touch of her fingertips she stroked my tender balls. They were still quite sore, but her gentleness worked and added to the pleasure she was giving me.

"Please, Master, fuck my ass."

"Master?"

That feels right to me. The other way was wrong, I didn't like that version of myself, it scared me. Hurting you was exciting, but it scared me.

"Wouldn't it scare you being hurt?"

"The dynamic is interesting though, that excites me."

"We could have sex without pain."

"Not with your big cock in my tight ass we couldn't."

That broke me up and she joined in for a delightful, shared laugh. When she' gathered herself she slipped her mouth back over my cock and began sucking and tonguing me intently. I slipped a finger into her crack and teased her puckered rosebud. She wriggled excitedly in response.

I reached out to the bedside table to grab the lube. she rolled onto her hands and knees, presenting her butt eagerly. I leaned in to tongue her. I licked the length of her crack from perineum to coccyx, then pointed my tongue to tease her opening. I gripped her hips and began thrusting into her funky hole. She groaned happily and pressed back to meet me. We kept at it for a couple of minutes before she spoke.

"Please fuck me now.."

I moved close, squirted a glob of lube on her brown eye, slipped my finger in, to distribute some inside, and coated my cock with more.

When I touched my glans to her anus she pushed back, and I began to slip inside her. She was wonderfully tight around me when I pressed deeper, and she screamed at the pain when I violated her sphincter. I hesitated momentarily.

"Don't stop, Tommy, fuck me."

She pushed back to force me deeper, so I drove all the way inside her fiercely gripping tunnel. Her deep groans inspired me to fuck her hard and deep. I reached around her to search out her clit and begin working it in synch with the thrusting.

"Oh, yes, yes."

"Do you want to cum?"

"Oh God, yes, please."

I worked her clit, right next to the pearl itself enjoying the feeling of her squirming and clenching her anus around my cock and her frenzied attempts to get my fingers in the perfect spot to push her clit over the edge. I maintained position, just out of reach for her.

"Shall I let you cum?"

"Please, Master, I need it."

"Master again, are you my slut, Gloria?"

"I'm whatever you want me to be."

"Do you want to be my owned slut?"

"If you'll have me, Master, yes."

Her anus grasped my cock desperately as she pushed back seeking deeper penetration while squirming to get more pressure for her swollen fuck button.

I thrust forcefully into her tight hole but moderated my pace to hold her right on the edge, desperately seeking the release I was holding just out of her reach.

"Why should I let you cum?"

"I need it so badly, I'll do anything you want, just please let me cum. You can use me anyway you want."

"That's a dangerous offer."

"I mean it. My body is yours."

I moved my hand from her vulva and grasped her breast aggressively, moved my other hand so I had a tight grip on both.

"Are these my tits?"

"Yes."

I squeezed them hard, digging my fingers deep into her flesh. She yelped and shook as I continued intensifying the cruel pressure. Her whimpers were a mixture of pain and need.

I brought my hand back between her legs and resumed working her clit.

"Oh, thank you, yes, please may I cum for you."

"Do you want me to own your orgasms?"

"Yes, Master. I think I do."

I fucked her hard and fast, making crisp slapping sounds against her womanly butt cheeks with each full stroke until she came loudly and collapsed onto the bed under me.

"I doubt this is what your friend Genevieve had in mind for you."

"Tough, this feels right for me."

"Was that your first time doing anal?"

"I tried it once with my ex. I didn't think much of it. He's much smaller than you and he didn't make me cum."

"How was it for you tonight?"

"I loved it. Your big cock hurt, but it hurt good. I came like crazy from your hand too."

"Good. I liked it earlier when you did me."

"I guess we're both anal sluts."

We shared a laugh, and she rolled over to face me.

"Are your balls okay?"

"A little sore but they'll be fine."

She scrambled down to kiss them with whisper soft care. Softly teasing my cock, she gradually inspired tumescence despite the soreness and my recent orgasms. She stroked my thighs and slipped her hands around my hips as she slowly wrapped her lips around my corona and teased my frenum with her tongue.

I began to respond to the lovely sensations. She gradually worked my whole cock into her mouth and sucked it gently as it grew in her hot mouth. I'd never been sucked quite like this, slowly and calmly like she was sucking a hard candy despite how funky my cock must have been. She made no attempt to create friction other than the mini caresses in slow motion with gentle suction. She sipped me, seeming to be enjoying herself immensely, and I enjoyed every blissful moment of it.

Gradually passion grew out of the gentle caress from her tongue and lips. I felt myself building to an amazing climax that belied the softness that produced it.

I shuddered and groaned as my sore balls fired streams of hot cum into her passive mouth. She sipped every drop through her straw, my cock and swallowed every drop contentedly.

"That was wonderful."

"I liked it a lot too. I love your cock. the taste, the feel, the shape, the texture, and your cum is delicious, Master."

"You're sure you want that?"

"Yes, sir. I want to belong to you. If you will have me."

"It's complicated you know. I belong to Mistress Pamela."

"Yes," she gnawed her lip.

"She may think that you would need to be hers too then, since she owns me."

Her conflict over that was evident.

"Have you ever been with a woman?"

"Once with Genevieve."

"How was that for you?"

"We were drunk."

"And?"

"I enjoyed it, but it was complicated."

"Just the once?"

"Yes, but she seems interested in an encore."

"How do you feel about that?"

"I'm not sure, conflicted I guess."

"How would you feel about being with Mistress, or Desiree?"

"I don't know, a little weird probably."

"Well that would surely come up if she considered you to be her slave by extension."

"I guess that's for you and her to work out, if you really want me to own you."

She rested her cheek against my thigh, and I ran my fingers through her curls while we fell silent, deep in our own thoughts.

"I'm not sure that sort of relationship is right for us."

"Why not?"

"It could get awkward for you around Travis. I wouldn't want it to affect him."

"We can't let that happen."

"I know. We can be friends with benefits. When he's with his dad we could have time together."

She fell silent for a bit.

"That actually makes sense. It would be simpler all around, for everyone, wouldn't it?"

I nodded and kissed her forehead.

"So, fuckbuddies?"

She returned a wan smile and nodded.

"We still friends?"

I nodded before kissing her affectionately.

"With benefits."

She slowly allowed her smile to blossom from wan to warm and threw her arms around me.

"Lots of benefits?"

"Whenever possible."

"Whatever benefits?"

"Anything goes."

"Perfect."

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