My New Boss Pt. 21

"Steph, that feels so good," I moaned as the teenage girl caressed me.

At one point, her lubed fingertip slipped between my ass-cheeks, tenderly brushing against my taint. I stiffened up involuntarily and Steph whispered in my ear again.

"You like that, baby?" she teased. "Do you want me to play with your ass?"

I swallowed hard, and moaned a quiet affirmation, excited to see how much play Steph was going to allow me. The young girl adjusted her position slightly, and her hand slipped under my buttocks.

"Here?" she asked innocently, as her fingertip brushed across my rosebud.

In an ideal world, I would have liked to have removed the condom and the numbing gel, got balls-deep inside Steph, and fucked her bareback to a very quick orgasm. However, with my twin tormentors, Suky and Amanda, competing for "sadist of the year" awards, my world had suddenly become less than ideal. My cock-head and shaft were numbed beyond comprehension, encased in a very thick, climax-control condom, and a million miles from orgasm.

My asshole, taint and nuts, free from the inhibitors of the gel and condom, felt hyper sensitive, and Steph realized that this was the key to my orgasm. She brushed her fingertip across my rosebud several times, coating the entrance to my anal passage with KY lubricant. Once my asshole was lubed up, she applied a little pressure, my sphincter gave way, and her finger slipped inside me.

"Feel good, baby?" she teased, as she wiggled her fingertip around inside me.

"Oh my god, Steph," I moaned, "That feels amazing."

We quickly settled into a routine, me fucking Steph with deep thrusting strokes, as I ground my nuts into the palm of her hand, and her knuckle-deep in my ass trying to reach my prostate. We kissed tenderly as we fucked, and I gazed into her youthful, innocent eyes, in search of release, but after several minutes I was no closer to orgasm, and I started to tire.

Maddeningly frustrated does not even begin to describe how I was feeling. I was overwhelmed with desire for Steph, and wanted nothing more than to bust a nut inside her. Amanda however, was an expert at tease and denial, and had other ideas. She sidled up behind me, and it was her lips that I felt brush against my earlobe.

"You look like you are getting tired," she began. "I want to offer you a way to orgasm, but it will require a little compromise on your part."

"Please let me come, Amanda," I begged. "My nuts are aching."

"Speak up," she instructed me, "this is going to be a group decision. The girls need to hear what you have to say."

"May I be allowed an orgasm, Amanda?" I asked, more forcefully. "My nuts are hurting from the prolonged stimulation, without release."

I heard a few titters from the girls, and Rim put her hand up, as if we were in a fucking classroom.

"Offer him the choice of staying inside Steph, or removing his condom and numbing gel, and allowing him to come inside his pocket pussy," she suggested.

"Great idea, Rim," Amanda said cheerfully. "What's it going to be Timmy?" she asked me with a smirk on her face.

I was over them fucking with me. My nuts hurt, I was getting tired, and I just wanted to get off. So, without even acknowledging Amanda, I reluctantly slipped out of Steph's tight teenage pussy. A pout returned to her face, and she let out a frustrated moan.

"Are you really going to choose your pocket pussy over me?" she asked in astonishment.

Steph appeared to hold no grudge towards me, because she helped me remove the climax-control condom and grabbed a wet-wipe. The young girl tenderly wiped all traces of the numbing gel from my cock, her feminine hands all over my junk, sweet talking me the whole time.

"Does that feel good, baby?" she asked, as the feeling returned to my cock. "Do you think you could bust a nut now, if they let you slip back inside me?" she teased.

"Well, that is not going to happen, Steph," Amanda said coldly. "It's pocket pussy time for this wimp."

Once Steph was finished cleaning me off, the sensitivity had returned to my cock, I was fully erect, and I had a large glob of pre-cum pooling at the tip of my cock. Steph looked at me, glanced at my cock-head, and licked her lips.

"Do you really have a recent clean STI battery?" she said softly.

I nodded silently, instantly regretting the lost opportunity of coming inside Steph. I stared into her eyes for a few moments, feeling the strong connection between us. She was just so angelic looking, so breathtakingly beautiful, so youthful and innocent. I guess she must have felt something too, because she smiled sweetly at me, lowered her lips to my cock, and enveloped the tip of it in her warm, moist mouth. She only sucked me for a few seconds, but the memory of her lips on my cock as she made eye contact with me and smiled, will stay with me forever. When she raised her head back up, the pre-cum was gone, replaced by traces of her Barbie Pink lipgloss.

"Use a wet-wipe to clean him up, for fuck's sake," Amanda barked.

Steph lowered her eyes to avert my gaze and reached for another wet-wipe. She used the damp towelette to wipe my cock-head clean, her lipgloss marks being removed in the process. Then, in an unsolicited move, that was clearly intended to enhance my orgasm, she wiped the entrance and interior of the pocket pussy clean of the numbing gel. Once she had removed most of the gel, she picked up the KY lubricant and applied a very generous helping to the inside of my pocket pussy.

"Now you should be able to bust a nut, baby," she said sweetly.

Steph grabbed the tip of my cock, lined me up with the bright pink pocket pussy, and helped me slide right in. Under normal circumstances, I would have been able to blow my wad inside that thing in just a few moments, but Amanda had other ideas. She knelt down behind me, and rested her hand possessively on my ass.

"Fuck it baby," she ordered, "get balls deep in your new puss."

Experience around dominant women like Suky and Amanda, has taught me to blow my load as quickly as possible, whenever I am offered the opportunity. For this reason, I started to pound into my pocket pussy as hard as I could, trying to get my rocks off. I did notice Amanda started to get closer behind me, which didn't bother me at first, until I felt a sharp prick on my ass-cheeks. I turned around immediately to see what it was, and I was shocked to see Amanda was wearing a spiked belt.

The spikes probably weren't sharp enough to draw blood, but they really made me recognize where she was, in relation to my position, and I had to start to fuck the pocket pussy much slower, more controlled, and with more shallow strokes. The adjustments made for a much less fulfilling fuck, but every time I tried to pound a little deeper, I got rewarded with a sharp prick on my ass. It was enough to get my attention, and I slowed my penetration down again.

Amanda nestled in really close behind me enjoying the inhibiting effect that she had on my lovemaking. She slapped my ass occasionally too, and called me a bitch. My movement was restricted to a slight grinding of my pelvis, and my nuts ached even more now, as I was no closer to my release.

At some point, Amanda leaned forward, the spikes forcing me deep into the sex toy, my pelvis jammed against the opening trying to avoid being pricked. She bit my earlobe more aggressively this time, and offered me an alternative.

"Would you like to exchange the spikes for something softer?" Amanda whispered.

"Please, Amanda," I begged, "just let me come."

Amanda removed her lips from my ear, and I heard her unbuckle her leather, spiked belt. She tossed it on the sofa in front of me, and I saw some blood spots on the tips of the spikes, evidence that she had indeed pierced my skin. I felt her shuffling around behind me, and then I heard the ominous click of a dildo attachment, being inserted into her harness.

I was beside myself with embarrassment and humiliation that she was going to sodomize me in front of the assembled women. Amanda slapped the dildo against my ass-cheeks and I surmised that it was a soft, flexible shaft, probably made of latex. As Amanda lined up the phallus with my rosebud, it made sense why Steph had lubed my asshole up earlier. This event was obviously pre-planned by the girls, which made it even more emasculating.

Amanda slipped right inside my anal passage, and started to fuck my ass. My leash, which had laid down the side of my body for the entire time that Steph had fucked with me, was now wrapped around Amanda's fist, and used as a way to control my movements. As Amanda began to really fuck my ass, I wished that I had been lubed with the numbing gel, instead of the KY lubricant.

Amanda's deep, penetrating strokes, forced me all the way inside my Hello Kitty sex toy, and prevented any backward movement on my part. It quickly became apparent that I was not going to be able to come, until after she was done fucking my ass. Amanda fumbled around with a remote control that was lying on the sofa, and I felt a vibration on the back of my nuts. I assumed that she had restarted my cock-ring, but as it happened she had inserted a clitoral vibrator, and was stimulating her own genitals.

I knelt there, a passive recipient of a protracted butt-fucking, as Amanda approached her first orgasm. The girls were fully engaged now, egging Amanda on as she dominated me.

"I am close," Amanda announced, shortening my leash with a sharp tug of her wrist.

A few seconds later, as the clitoral vibrator worked its magic, Amanda had a very vocal orgasm behind me, her phallus buried deep in my anal passage. Amanda enjoyed four or five tremendous orgasms, nearly choking me with the leash each time she came. After her last release, she slowed the pace of her anal assault, and dropped the leash to the floor.

"I have a little surprise for you, Timmy," she said, to the delight of the audience who were obviously in on it.

Amanda reached under her strap-on, and grabbed hold of the large testicles that hung beneath it.

"I am going to come in his ass, girls," she said coldly, "Teach the little bitch a lesson in humility."

Right after Amanda's proclamation of her imminent orgasm, she gave her fake nuts a squeeze, and I felt some warm fluid spurting into my anal passage. It was a very alien feeling, unlike anything I had experienced before. At Suky's behest, I had given myself numerous anal cleanses. However, even though this invasive procedure necessitated squirting liquid into my anal cavity, it paled in comparison to Amanda's release. The liquid that Amanda spurted inside me, was not only warmed to body temperature, but the streams were much more powerful, much more focused, much more voluminous even.

After about the sixth or seventh rope of cum, I realized that Amanda must have picked up a new sex-toy from her place of employment. Presumably an ejaculating dildo, that I had seen occasionally in lesbian porno movies. I wasn't sure if she had loaded the fake nuts of that penetrating latex device with real semen, but it certainly felt to be the same consistency and temperature of a man's ejaculate. It was a copious load, by the time she finished unloading inside of me, and even before she withdrew the latex dildo, it began to leak from my ass.

Having my anal cavity pumped full of semen did nothing to increase my sexual excitement, so I think it was the humiliation of the whole ordeal, that finally pushed me over the edge and helped me evacuate my own nuts. As I felt Amanda's load leak from my ass onto the back of my nuts, I came with a roar in the Hello Kitty pocket pussy, the girls erupting into a spontaneous round of applause.

Amanda withdrew her latex, ejaculating dildo from my anal cavity, and stood up behind me. I remained coupled to my sex toy, on my knees, trying to gather myself after a stupendous orgasm. Amanda, emboldened by the round of applause, and because she is a sadistic man-hater, gave her fake nuts one last squeeze, and to everyone's astonishment, launched a huge rope of semen that landed with a splat across my lower back and ass-cheeks. It was so totally unnecessary, a final "fuck-you" to me, as I knelt before her.

She didn't allow me anytime to bask in my post-orgasmic bliss either, ordering me to withdraw my cock, right after she came on the back of me. Amanda pulled the Hello Kitty fuck-toy from its resting place between the sofa cushions and frame, and held it skyward.

"Let's see how his load compares to Tim's," Suky said with a giggle, referring to my boss, and the copious loads he always releases.

This wasn't really fair, as half of my load was still inside the pocket pussy. However, to the delight of the girls, Amanda rotated the bright pink sex-toy one hundred and eighty degrees, thus turning it upside down. She placed her dainty hand underneath the opening, and the entire room watched expectantly.

It was truly a pathetic sight, as my cum dribbled out of the entrance of the pocket pussy, and after waiting several moments, barely filled the palm of Amanda's hand. She walked around the room, showcasing the pitiful load to everybody, before raising the palm of her hand to my lips.

"Eat, bitch," she commanded.

A raucous cheer went up around the room as I slowly lowered my tongue to the rapidly cooling mess, and began to lap it up.

"Let's get some pictures," Suky said cheerfully, as she approached me holding her cell phone. "Amanda first."

Suky snapped a couple of photos of me eating my jizz from Amanda's hand, instructing me to smile for the camera. Amanda grabbed Steph's pink panties from the sofa, and hung them around my neck, as Suky continued to document my subjugation. A few minutes later, with the scene having been duly recorded for posterity, and Amanda's palm licked clean, Suky dismissed me.

I scurried out of the room with Steph's panties hanging from my neck, my lips glossed with my own semen, Amanda's load splattered all over my rear and leaking from my ass, feeling like a total bitch. I hid in my room for what seemed like an eternity, listening to the laughter and cheers from the front room, as they relived my nightmare. I was praying they wouldn't call me back in there, and I didn't relax until much later, when I heard the departure of our guests.