My New Boss Pt. 24

I took a quick shower, and although I would have normally attended to my grooming needs prior to anyone seeing me naked, Amanda had removed all traces of hair from my body during the week I spent with her, so I was ready to go. I had an erection the entire time that I showered, while I got dressed, and while I waited for the girls to get comfortable. Part of my excitement was physical, epididymal hypertension, to be specific, but the other part was anticipation of how my orgasm was going to happen.

The realist in me understood that I was probably going to be subjected to a very humiliating ordeal, given the fact that there were two sadists, Suky and Amanda, in my audience. The optimist in me hoped that the girls would cut me some slack, maybe let me fuck Steph doggy-style, or blow my load on Amanda's tits. Just kidding, the best I could have hoped for was maybe to mount my pocket pussy, if I was lucky.

Amanda and Suky kept me waiting for way longer than necessary, my anticipation increasing my level of arousal with every passing minute. Finally, I heard my cue to enter the room, as Amanda called out for me.

"Crawl in here boy," she barked forcefully.

I had hoped to be able to walk into the living room like a man, but in a move of self-preservation, I got down on all fours, and crawled in there like a dog. As I entered the room, a wave of silence descended upon it, and I felt very self-conscious. Amanda was stood in the center of the room, and my service pillow was at her feet. I didn't even need to be given any instructions, I just crawled over to the pink, heart-shaped silk pillow and knelt on it.

Amanda rested her black leather glove on my head, and began to address the room.

"As you are all aware, my boy has endured forty-one days of forced chastity," she began. "Our original plan was ninety days, but due to an unforeseen medical condition, he will be getting a release today. I will turn you over to his medical professional, Marissa," she said, yielding the floor to none other than my nurse.

My anticipation of an orgasm was immediately replaced by acute embarrassment, as Marissa took the floor. I saw this young woman every fourteen days for a STI check, part of which involved a sperm sample. Marissa knew my sexual hot-buttons as well as anyone, the clinic having provided men's adult magazines to encourage a speedy release. I was there so frequently, that upon arrival Marissa would hand me my favorite issue of Penthouse, opened to the exact page I used to facilitate my orgasm.

After numerous times at her facility, Marissa suggested changing things up for variety, and after a quick consultation, I confessed to having a crush on Steph. Marissa, like many of her Millennial generation, was very proficient at Photoshop, and managed to attach a head-shot of Steph, to the body of a porn-star, dressed in a schoolgirl uniform. Marissa printed this alluring photograph for me and handed it to me right as I went into the designated room. When I emerged about three minutes later, with my sample cup almost full, and the picture of Steph the schoolgirl, defiled with traces of my ejaculate, Marissa knew that she was onto a winner.

Two weeks later, when I arrived for my sperm sample and STI battery, Marissa handed me a laminated, eleven by fourteen inch, copy of the schoolgirl photo, the inference being that I could jerk off directly onto the photo, and scoop my semen into the sample cup. This set into motion a routine that was as predictable as it was humiliating. I loved jerking off onto that picture, but hated the embarrassment I felt right after I came, and had to hand the defiled photo back to the young nurse.

Now as Marissa took the floor, holding an eight by eleven laminated piece of paper in her hand, my desire to orgasm was in direct conflict with my acute embarrassment. My hard-on, and the accompanying testicle pain wasn't going anywhere, but I did not want to do this in front of a large female audience.

Marissa walked slowly towards me, seemingly relishing her brief time in control of me. When she got to my service pillow, she placed the photo of Steph dressed as a schoolgirl, on the floor next to me. The second I glanced at it, my cock danced in my boxers.

"I need to give you a quick medical check-up," Marissa decreed. "Take your boxers off, please."

Even though Marissa was being professional, in my agitated state any female interaction was going to be difficult for me, and as I pulled the waistband of my silk boxers over the tip of my blood-engorged cock, a large strand of pre-cum hung from the tip of it. I heard the snap of her latex gloves, and then I stiffened as her fingers rubbed across my swollen cock-head. There was an immediate transfer of my seminal fluids to her gloved hand, and Marissa looked to the girls for direction.

"He eats anything he leaks," Amanda told the nurse dispassionately, and Marissa raised her fingertips to my lips.

I really didn't want to do this, as I knew it would forever alter the way Marissa viewed me, but I heard Amanda cough, and the non-verbal signal was sufficient to snap me back into focus. I tentatively extended my tongue, licking my semen from the latex gloves. A raucous cheer went up from the assembled crowd, as Marissa became my latest tormentor.

Her brief physical examination of me was without drama. She squeezed and separated my testicles to gauge my level of discomfort, and then examined the head of my cock,

"No excessive swelling," she decreed, "well nothing worse then you would expect from a guy who hasn't got his rocks off in six weeks," she added cheerfully.

Marissa examined my anus next, seemingly for no reason other than because she could.

"Lean forward," she instructed, as she stuck two fingers into a jar of Vaseline, that was on the floor.

A year ago, if I had been naked on my knees in front of a group of young females, and one of them tried to stick two fingers up my ass, I would have fought back. However, they had subjected me to so many indignities over the last few months, that I had no fight left in me. My eyes widened a little, and I tensed up until she penetrated my sphincter, but other than that, I remained passive as Nurse Marissa probed my anal passage. She lightly brushed my prostate, causing an involuntary stiffening of my cock, followed by another glob of pre-cum being expelled.

Marissa knew the drill now, and fed me my seminal fluid using the fingertips of her other hand.

"Good to go," she said pleasantly, as she withdrew her fingers from my anus, and removed her latex gloves.

I looked down at the floor to hide my embarrassment, focusing on the beautiful photo of Steph, dressed as a schoolgirl.

Amanda resumed control of the floor, handing me a small bottle of KY lubricant.

"Knock yourself out," she said with a smile, "we want to watch you bust a nut."

I didn't need a second invitation, and flipped open the lube. I poured a liberal dose into the palm of my hand, and then inverted the bottle and gave it a healthy squeeze, coating my cock with the silky liquid. Once I had lubed myself up sufficiently, I adjusted the position of the laminated photo, and began to jerk off. I knew I wouldn't last long as it had been over forty days since my last release. However, I didn't realize that Amanda had one more surprise for me.

I smelled Steph first, that intoxicating mixture of designer perfume and teenage pussy, that drove me insane whenever I was near her. I was kneeling on my pillow, cock in hand, jerking myself off slowly as I fixated on her picture. She approached me from behind, kneeling beside me on the living room floor. I felt one hand on my ass first, then her lips nibbling my earlobe.

"Are you going to come on my face?" she teased. "I have been looking forward to that for a long time."

Steph was obviously referring to me blowing my load across the laminated photo of her, but nonetheless her words struck a chord within me, bringing me closer to orgasm. She continued to whisper words of encouragement in my ear, as her nails raked across my butt-cheeks.

"Maybe one day I will dress up as a schoolgirl and let you fuck me," she cooed. "No condom, of course, baby. You can come inside my teenage pussy, too."

Steph really knew how to get inside my head, and chose her words carefully, in order to maximize my pleasure. I focused on the picture on the ground before me, a full page laminated shot of my dream girl dressed in a sexy schoolgirl uniform, her long blonde hair in pigtails, which accentuated her youthful looks. I continued to jerk myself off, trying to block out the increasingly raucous encouragement and taunts, from my female audience.

Steph scooted closer to me, and slipped her manicured hand under my ass-cheeks, so that she could tease my taint. Her lips remained glued to my ear, as she continued to whisper sweet nothings to me.

"When do you think we will finally fuck, baby?" she asked sweetly. "It's all I ever think about," she lied, trying to get me to blow my load.

It was inevitable that she was going to break me with her words, and the extreme verbal provocation, coupled with my six weeks chastity, was enough to take me over the edge. My stomach muscles stiffened, my swollen nuts constricted and l let out a whimper as Steph's fingertip brushed across the entrance to my asshole.

"Does that feel good, baby?" Steph teased. "Imagine if it was my tongue pleasuring you back there, instead of my finger. Do you like rimjobs?"

I stared intently at her photograph, laying as it was in the direct path of my impending eruption. Steph's angelic face looked up at me, through the laminate designed to protect it from my seminal fluid. Her beautiful symmetrical features made me want her so badly, and the thought of such an innocent looking face being buried between my ass-cheeks caused my heart to beat much faster. She was way too cute to be eating any guy's ass, and yet the thought consumed me. As I refocused on her photo, her baby blue eyes were inviting me to come on her perfectly sculpted nose.

I felt her fingertip slip inside me, my sphincter allowing her entry before tightening around her dainty middle digit. Marissa had used a generous helping of Vaseline during her "examination" of my anus, and this enabled Steph to slip a second finger inside me.

"Tight!" she whispered, as she wiggled her fingers around inside me. "Just like my virgin ass."

Steph's fingertip brushed my prostate right before I felt my balls tingle, and I let out a loud moan of ecstasy as I ejected my first rope of cum, which landed on the center of the laminated photo, with an emphatic splat.

"Bullseye, baby!" Steph whispered in my ear, "blow your whole load on me."

My second shot was just as powerful, my body seemingly determined to empty every trace of my six week load from my aching nuts. Steph had located my prostate now, and was brushing against it as I came all over the picture of her.

"You like that, baby?" she teased, as I continued to erupt onto her picture.

Steph massaged my prostate until my orgasm was complete, and I was kneeling there in front of her photo, panting and leaking onto the floor in front of it. I had completely defiled the photo, my semen having splattered across the rear of her schoolgirl uniform, as she posed seductively in the doggy-style position. In the picture, she was looking back over her shoulder at me, and I had coated the back of her neck, both of her pigtails, and the pink silk ribbons tied in them. Traces of my semen were all over the side of her face, and her cute upturned nose was covered in my ejaculate too.

"Fuck, that was hot!" Steph whispered. "Kiss me baby."

I turned my head towards the young girl, and for a split-second she looked startled. I realized my mistake right as she corrected me.

"Well, not the real me, silly," she said with a giggle, pointing at her photographic image.

My face reddened at the miscommunication, and I lowered my head slowly to the jizz-soaked laminated photo. My semen had cooled rapidly, spread as it was across the plastic film, and I tentatively kissed Steph on the lips, transferring some of my ejaculate to my own lips, in the process.

I know most men react in a similar manner, right after they blow their load, and I was done with our fun and games. Amanda, however, was just getting started, and used this moment as a photo opportunity, whipping out her iPhone to document my debasement. After a few poses of me kissing and licking the photo, Steph joined in our impromptu session, and Amanda posed us for her amusement.

In most of the pictures, Steph simulated a look of shock at my disrespect, her hand partially obscuring her mouth, which was open in disbelief. These photos made her look her even more innocent, and made my cock twitch with desire for her. At some point, Marissa stepped up with a semen-sample cup, and scooped the remains of my load from the laminated picture into it, for later testing. This seemed like a total waste of time, as my cock had been completely sidelined for the last six weeks.

Just as it seemed like I was off the hook, Steph asked for a souvenir picture.

"One for the road?" she said cheerfully, her angelic face hiding her devilish intent.

This picture would later come to haunt me, ending up as it did as the screensaver for my iPhone, iPad and computer. In it, I am kneeling at Steph's feet, completely naked, holding my photo up proudly, as if I had just met my celebrity crush. My semi-erect cock hung between my thighs, the tip red and irritated, from the six week long period of enforced celibacy and sexual torment. There was a small puddle of seminal fluid on the floor between my legs, my body's attempt to empty my nuts of any remaining semen.

Steph is smiling broadly, her blue eyes sparkling under the flash of the camera, her makeup flawless, having taken the time to refresh it before the final photos. She is resting one hand on top of my head possessively, as if I am her newest toy. I am looking directly at the camera, holding my photo under my chin, the laminated surface appearing extra shiny, having just been ejaculated on. I also have a broad smile pasted across my face, but it is obviously forced, and upon closer inspection you can see abject shame in my eyes, and traces of semen still on my lips.

I am confronted with that picture on a daily basis, a constant reminder of the love that I have for Steph, and the disdain that she feels for me. My one regret is that she didn't allow me to pose in a more equitable position, to at least create the illusion that we were lovers. Marissa received a copy of this photo shortly after it was taken, a beautifully laminated eleven by fourteen inch glossy reprint, that is my new jerk-off photo, for my bi-monthly semen sample. She keeps it at the medical facility, but it is in with the all of the other jerk-off materials and girly magazines, so anyone is free to use it to bust a nut, if they so desire.

I have developed a true love-hate relationship with that picture. On the one hand, I hate the way that it encapsulates the true dynamic between Steph and I, that of smitten older man, and disinterested teenager. On the other hand, between my bi-monthly medical checkups, and my weekly scheduled orgasms, I only get to bust a nut about six times a month. Truth be told, I get the hardest and come the quickest, when I am holding that fucking photo.