Friday afternoon the phone at my desk rang. “Hello?” I answered, and then smiled.
“Hello my little pet,” Mistress Jacqui’s husky sultry voice came over the line. “Would you like to entertain me tonight?”
“Whatever you desire,” I replied quietly, hoping I couldn’t be heard outside my office door.
“Be here at the usual time,” she said, and then hung up.
At 7, I was pulling into her driveway. For those who have not read my earlier story about Mistress Jacqui, she lived in the suburbs, with her house set at the end of a very long driveway in isolated seclusion. I quickly exited the car and walked to the entry door. When I entered, there was a note on the table inside the entry hall. It read:
Pet, do not undress. I wish to speak to you
for a bit before we begin. Place my collar
around your neck, ring the bell, and then
await me on your knees -
I did as the note instructed. Shortly after ringing the doorbell, I could hear her heels clicking on the hardwood floor as she approached. The door swung open, and I was gazing down at her red leather stiletto heels. “I’m here to serve you Mistress,” I said ritually, then kissed the toe of each foot.
She raised my chin with her hand and she squatted down to gaze into my eyes, a friendly, warm smile on her bright red, full lips. She was wearing a simple mid-length red leather skirt and a white silk blouse. In her left hand she carried a leash, which she attached to my collar. “Come along, pet. I wish to talk with you a bit.”
I followed along obediently, my eyes watching the sway of her round ass under the skirt. We went down the hallway and into Mistress Jacqui’s playroom. In addition to the queen sized bed and St. Andrew’s cross, she had moved a large padded chair into the room. She made her way to it and sat down, indicating that she wished me to kneel before her.
“Look at me, pet,” she said softly. As I raised my gaze from the floor, Mistress Jacqui crossed her legs, and I was able to catch a quick glimpse of her neatly trimmed bush. “Do you trust me, David?” she asked.
“You know that I wouldn’t do anything to injure you, right?” she smiled, “I might hurt you, but you know what I mean?”
“Yes, Mistress. I know you don’t want to harm me. You know what I can take. Sometimes I don’t, but you seem to.”
She took a deep breath and seemed to collect her thoughts, “I think you are ready to move into a new…ahhhh…area,” she said, “First however, I want to make sure that you agree.”
She leaned forward and again she reached down and cupped my chin in her hand, “I’ve been training you to be a cocksucking whore, and tonight I’m going to try you out on a real cock. What do you think of that idea?”
I swallowed, took a deep breath, and then smiled at her, “I would love to be your real cocksucking slut, Mistress Jacqui.”
She laughed then, “Be careful what you wish for…” Mistress Jacqui leaned back in her chair. “Strip.”
I quickly shed my clothes, neatly folded them and placed them on the floor. My cock, as usual was rock hard. Mistress idly ran her shoe along it, “It seems as if you’re certainly ready,” she mused. She got up from her chair, “Follow me, pet,” she said, tugging on the leash. She led me out of the room and down the hall, into the bathroom. “Your playmate will be here soon. Since he knew what was going to happen tonight, he will be prepared. You, on the other hand, my dear, are not. Lean over the tub.”
As I did, Mistress Jacqui reached onto a shelf and retrieved a red latex 2-quart enema bag, which she proceeded to fill with warm water. Soon, I felt her slowly sliding the nozzle into my ass. With a “SNAP”, she released the clip, and the water flowed into my bowels.
“God! This ass is so white!” she said, bringing her hand down hard on my left cheek. “It seems no matter how long or how hard I work it over, it never stays red,” she observed as she continued raining blows upon my ass. “And you know how much I hate a pale ass.”
“Yes, Mistress, ” I groaned out, my discomfort partly from the spanking, and partly from the cramping the enema was causing.
Just then, the doorbell rang. “There he is,” she said gleefully. “You may release your enema, clean yourself up, and return back to the playroom.” She turned and strode out of the room. I slid over to the toilet and expelled the enema, along with the contents of my bowels. It took several more minutes to clean myself up, and then I headed back to the playroom.
As I approached, I could hear Mistress Jacqui softly talking…too softly for me to make out the words. Entering the room, I saw another man kneeling naked at her feet, his back toward me. Mistress looked up, “Ah, here he is now,” then pointed to the floor next to him, “Come kneel next to Robert, David.”
I took my place and Mistress formally introduced us. Robert looked to be about my age, with hair a lighter shade of brown than mine, and piercing green eyes, which were coolly appraising me. He was more muscular than me, and would probably be three or four inches taller when standing. His groin area was shaved clean, and his cock stood out ramrod straight, just like mine. I felt a small swelling of pride in that it wasn’t quite as long or as thick as mine.
Mistress Jacqui had been perched on the edge of the chair. She now leaned back and smiled wickedly. “Now, I asked both of you over here to entertain me. I want the two of you to compete,” pausing, she spread her legs, and ran a finger through her glistening pussy, “for this. The rules are really very simple. The two of you will lie down, side by side, in a 69 position and start sucking each other off. The first one to cum, loses.” She continued fingering herself, “The loser gets a whipping and then gets to watch as the winner has his way with me.” She laughed throatily, “Well, really I should say ‘Has my way with me,’ because I’ll be telling you what I want.” She sighed then, “God, just thinking about it is making me sooooo hot. Lie down and start sucking, faggots!” she sneered.
I knew I was in trouble when Robert fastened his mouth around my cock before I had even started to lie down. I covered my moan by stuffing his cock in my mouth. I tried to remember what Mistress Jacqui had taught me with her dildo over the past several months. I ran my tongue around the head of Robert’s cock, and tasted his salty pre-cum. Working his shaft with one hand, I caressed and kneaded his balls with my other. I tried to take as much of his meat in my mouth as I could, but found myself gagging, and had to back off a bit.
Robert seemed to have no problem with deep throating my longer, thicker dick. It was obvious he was out to win. No teasing and heightening of my arousal, he simply wanted me to cum. He was running his fingers along the skin between my sac and asshole, tickling the sensitive flesh. My head was near Mistress Jacqui, and she had slipped off her heels and was running her bare foot through my hair. “Look at my two little cocksuckers. I love watching guys do each other. MMMMmmmm,” she sighed, “just think, one of you is going to get me, while the other gets….well, dick,” she laughed hard at her own joke.
I knew I was losing. Robert was working my cock like a high class call girl. I was trying everything I could think of to hold off – batting averages, Tony Soprano’s mother in lingerie, Joe Pesce in lingerie, anything, but it wasn’t working. I was moaning, humming around Robert’s cock, and I didn’t seem to be getting any reaction from him at all.
“Look at you, you bitch,” Mistress Jacqui whispered in my ear. I hadn’t even realized she gotten off the chair and was crouching down next to me, “You’re humping your hips like that little slut Katherine. You’re going to cum, and you’re going to lose,” I whined around the cock in my mouth. “Robert’s going to eat me and fuck me…all while you watch, your ass burning from the whipping you’re going to get.” I whined again, as my balls started twitching, punctuating the battle I was losing. “Don’t you dare cum. I swear you’ll be sorry. I’ll make you Robert’s bitch…”
“Oh, fuck! I’m cummmmminnnnnggggg!” I yelled, no longer able to hold it back. I caught a quick smile from Jacqui, before she slid down, and began whispering in Robert’s ear. He continued working on my cock, sucking to get every last drop of cum, milking my balls, as jets of spunk flowed into his mouth. I must have cum for a two minutes straight.
I collapsed onto my back, spent, exhausted and defeated. Before I knew it, Robert’s mouth was fastened over mine, and he was using his tongue to force my own seed into my mouth. My eyes flew open in surprise, Mistress’ staring deeply into them. “You didn’t think I was going to make Robert swallow your cum, did you bitch?” she smiled wickedly. “I hope it doesn’t fill you up, because it’s not the only thing you’ll be swallowing.”
I swallowed, my cum leaving a salty, bitter aftertaste. I was ordered onto the spanking bench. Mistress Jacqui secured my legs, while she had Robert secure my wrists. Standing up, his cock was right at the mouth. “Go ahead, pet,” Jacqui said to Robert, “He’s your bitch, use him.” I could hear her behind me, retrieving the implements of my punishment. “Make sure he blows you good. I want you to last a long time while you’re fucking me.”
Robert grabbed the back of my head and thrust his dick deep into my open mouth, choking me. I started to gag, as he held it there. As he pulled out, Mistress Jacqui brought her cat-o-nine tails down across my back and ass. My scream of pain was muffled as Robert drove his cock back in, his balls slamming up against my lips.
Robert continued to rape my mouth while Jacqui’s whip striped my ass and back. “You better get him off soon, you fucking whore! Your whipping doesn’t stop until he cums.” Robert had his hand wrapped in my hair and was using my mouth like a pussy. Mistress Jacqui started laughing, “Well, at least I finally found a way to keep this ass nice and red. I’ll bet you don’t sit for a week.”
Tears were streaming down my face, both from the whipping and the utter humiliation. Yet, my cock was again rock hard, showing my two tormentors just how much of a slut I was. I was being totally used for someone else’s pleasure, and I was in heaven.
Robert began speeding up his thrusts, and Mistress Jacqui matched his speed with the whipping. He buried his cock deep in my mouth, and I felt it swelling, until it suddenly erupted. “Fuck, yeah,” he moaned, as I swallowed, trying to keep up so I wouldn’t drown.
When he was done, I licked his cock clean. Mistress Jacqui leaned down next to me. “Are you okay?” she quietly whispered in my ear. “Do you want to stop?” I shook my head. “I didn’t think so. You’re such a slut. But, you’re my slut.”
As I lay there, recovering, Mistress had Robert lay on the floor. She straddled his chest, and then lowered her bare pussy to his mouth. “Eat me, pet, make me cum hard. Watching the two of you made me so fucking wet.” She looked over at me, her eyes half-lidded, “Oh, God, he’s so fucking good. His tongue’s right there on my clit….lick it Robert….ummmmmmmmmmmm…..I’m…gonna’….CCCCCCCCCCCUUUUUUUUUUUUMMMMMMMMMMMMMM!” she screamed, collapsing onto his chest, shuddering, as the aftershocks shook her body. She slid a bit farther down, slid over Robert’s hard again cock, and, with a low moan, impaled herself upon it. They fucked for over an hour. Robert had incredible stamina. She rode him for awhile, bringing herself to several orgasms, and then Mistress Jacqui got on her hands and knees, facing me, while Robert took her doggy-style. She made me look into her eyes, while Robert pounded her. I could see the absolute pleasure he was giving her, as her eyes dilated and glazed over.
“Shit, Mistress, I’m gonna’ cum,” Robert said after an hour.
“Yeah…cum with me pet…fill my pussy,” Robert buried his cock balls-deep in her, “Oh Christ…yeah…I can feel it…uhhhhnnnnn.”
They both rested there on the floor for a few minutes, drenched in sweat, the smell of sex heavy in the air. “Have the slut clean your cock off, Robert,” she ordered, as Robert withdrew from her. He presented his cock to my mouth, and I began cleaning it with my lips and tongue. I noticed Mistress Jacqui getting a stool from the corner of the room out of the corner of my eye. Not only did Robert have amazing stamina, but he was starting to get hard yet again. Mistress Jacqui had moved nearer my head. “Okay, Robert. I don’t want you cumming in his mouth again. Go stand over there.” She moved the stool closer to my head. When she sat upon it, it brought her well fucked, cum-filled pussy right to my mouth. “Clean me, bitch.” She put her legs over my shoulders, her feet resting on my back.
I hungrily devoured her, tasting the mix of her juices and Robert’s cum. “Yeah, that’s it, suck all that cum out of there.” Mistress Jacqui was running her hand through my hair, directing my mouth. I suddenly felt a cold sensation on my asshole. I started to buck my hips as I felt a well lubricated finger enter me. “Shhhh,” Mistress Jacqui soothed, as she wrapped her legs tightly around my head. “Don’t fight. I told you that if you came I was going to make you Robert’s bitch. Bitches don’t just suck…they get fucked too,” and with that, Robert rammed his cock into my ass, my scream muffled this time by Mistress’ pussy.
“He’s tight, isn’t he, pet?” Jacqui asked him.
“Oh, yeah. I’m not going to be able to hold out very long, Mistress.”
“Oh, neither am I. Can you reach David’s cock?”
“He’s been such a good little slut. Why don’t you give him a reach around? Jerk his cock.”
My ass-fucking, which had started out painfully, was now becoming pleasurable. Robert jerked my cock in rhythm to his thrusts. Mistress Jacqui had let up the leg pressure on my head, as I had stopped fighting. She was directing my head again with her hand wrapped in my hair. “That’s it, slut, lick right there, right on my clit. Ohhhhh, you’re going to make me cum again. Are you ready to cum, Robert?” He answered with a grunt. “What about you, my virgin little bitch, is Robert jerking your cock good?” I moaned into her pussy. “Yeah…good…I’m so fucking close…everybody cum NOW!”
Mistress jammed my head hard into her pussy and flooded me with her juices, while Robert buried his cock in my ass. I felt it spasm as he filled me with cum. This sent me over the edge and spunk erupted from my cock. Everything went white, and I felt like I was falling down a deep hole.
I don’t know how long I floated for. The next thing I remembered, I was lying on my back on the bed, with Mistress Jacqui lying next to me. She was lying on her side, her head propped up on her arm, smiling at me. “Are you okay?”
“Yes, Mistress,” I answered dreamily.
“Robert’s gone. It’s just you and me, pet.” She was quiet for a few moments, “You know I set you up, right?”
“Robert’s one of my oldest slaves. He’s broken in many of my little sluts, just like you. You did so well, David. I’m very proud of you.” I swelled with pride. “I’m going to let you rest for a little while, but I’m going to keep you for the weekend.” The evil grin returned, “And I’m going to fuck you silly.