Trust Fund Baby Pt. 13

Any resistance was now gone, and as she extended her tongue and began to tenderly lick my cock-head, there was another tap on my door. Jessica peeked around the door, and with a huge smile on her face, spoke with the confidence of a girl who knew she was in the inner-circle.

"Do you want me to come back later, Papa?" she asked. "You look like you are in the middle of something."

"No, Jessica," I said amiably. "Come on in. Your timing is perfect."

The way Jessica sauntered into the room as if she owned the place, was actually quite arousing to me. She had demonstrated her resourcefulness by being the first to get me off on Judgment Day, and now, as she and Casey made eye-contact, Jessica showed her leadership potential. Arriving at Casey's side, she placed one hand under the young Asian's chin, and in an authoritative voice chastised her for interrupting my blow-job.

"Keep sucking Papa's cock," she said firmly. "He'll let you know when he is done."

Casey nodded agreeably and lowered her lips back to my cock-head, as I motioned for Jessica to sit next to me on the bed. As soon as she lowered her tight little ass-cheeks to the comforter, we began to kiss, tenderly at first, but then with more passion. She had apparently brushed, flossed and gargled with mouthwash, because her breath was minty-fresh, and as our tongues intertwined, I felt the beginning of a connection to her.

"Would you like me to show Casey exactly what you like, Papa?" Jessica asked sweetly, between kisses, as Casey continued to blow me.

After I nodded my affirmation, Jessica knelt next to Casey between my thighs, and they took turns sucking my cock, bringing me close to the boil several times, before Jessica instructed Casey to stop, just before the moment of truth.

"This is edging," she explained to the young Asian. "Even if a man begs you to let him come, the longer you delay it, the more enjoyable his orgasm will be."

Truth was, as they continued to toy with me, bringing me tantalizingly close to release on multiple occasions, I did consider begging Jessica for an orgasm. However, she seemed perfectly aware of the effect that they were having on me, and continued to tease me.

"Sit right on the edge of the bed, Papa," Jessica instructed. "Bend your knees, feet flat on the bed, spread your legs wide."

As I maneuvered into her desired position, I realized that by doing so, I had exposed my asshole to the pair of them. Jessica, in full tutorial mode, continued to offer instructions to Casey, both verbally and via practical demonstration. Before long, Casey's cute Asian face was under my nut-sack, her moist tongue fully extended, as she flicked the tip of it across my taint. It felt really good as the young girl worked to pleasure me, but as soon as she emerged and was replaced by Jessica, there was a palpable improvement in the sexual act.

Jessica really knew her way around a man's asshole, and despite her best efforts to tutor Casey, I finally broke down and asked them to get me off.

"Jessica, can you eat my ass while Casey blows me?" I asked shakily, the anticipation of release starting to wear me down, after their prolonged edging session.

"Whatever you want, Papa," Jessica said cheerfully, as they got into their respective positions. "Get up on your knees for us. On the edge of the bed."

It had been quite a while since I had taken any direction from one of my house-pets, but Jessica seemed so concerned with my pleasure and sexual well-being, that I followed her instructions, and got up on to my knees.

I knew that I had made the right decision the second Jessica maneuvered into position underneath my nut-sack, and directed Casey to remain on her knees by the side of my bed.

"Keep sucking Papa's cock," she instructed the young Asian.

As Casey resumed her oral attentions, Jessica extended her tongue and began to perform analingus on me. When performed correctly, getting rimmed is my favorite sexual activity. However, despite having received a rim-job from just about every woman that I had ever kissed, I knew that it was definitely an art that took time and practice to perfect.

Apparently Jessica had put the time in, because her rim-job was comparable to Madison's, and as she and Casey worked in tandem to get me off, I knew that I wouldn't last long.

Once I was well on the road to orgasm, Jessica issued her next instructions.

"Turn sideways and get on all fours, Papa," she said sweetly, patting the mattress just in front of me, to indicate to Casey where she needed the young Asian girl to be next.

"Lay on your stomach, Casey," Jessica instructed the young girl. "Lips slightly parted."

Once the two of them were in their respective positions, Casey raised her head to look up at me, forming her mouth into a perfect O as she did so.

"Now you can scoot forward a touch, Papa," Jessica said sweetly. "Spread your legs apart a little wider for me."

Moving my knees further apart lowered my crotch slightly, and combined with my forward motion had the effect of lining the tip of my cock up almost perfectly with Casey's open mouth, formed as it was into a perfect O shape, as if inviting me to enter its warm environs.

"Now you can just fuck her face like it's a pussy, Papa," Jessica said cheerfully. "I will be doing my part to help you over the edge," she assured me.

Apparently she had done this before, because the way that Jessica had positioned the three of us, made it very comfortable for me to fuck Casey's face. I simply thrusted my hips forward, using the same motion that I would've used had I been taking one of them doggy-style.

Jessica wedged her nose between my butt-cheeks, and then wrapped her arms around my thighs, which held her firmly in place and enabled her to move with me as I thrusted into Casey's mouth. The three of us remained locked in this position for several moments, Jessica's tongue buried inside my asshole, as I face-fucked Casey.

As I slowly approached my orgasm, Jessica removed one of her hands from my thigh, and I heard what appeared to be the sounds of her sucking on her own finger. Seconds later, I felt her smoothly-filed nail brush across my rosebud, the tip of her finger wet from her saliva. Jessica knelt behind me and slid her middle finger inside my asshole, penetrating me deep enough that I felt the ridges of her first two knuckles slip through my sphincter, before the third knuckle came to rest against my rosebud.

Once it was evident that she was all the way inside me, she expertly located my prostate, rubbing it softly in a gentle circular motion, immediately confirming my suspicion that she had performed this particular sex-act numerous times. Even though her attempts at analingus had felt phenomenal, once she began to stimulate my prostate it felt otherworldly.

I began to fuck Casey's face in a much more aggressive manner, sliding in and out of her perfectly formed lips in an effort to achieve release down her throat. With Jessica's expert attention on my prostate, it didn't take me long to blow my load, and once again, as she continued to caress the walnut-sized gland inside my ass, I experienced a far longer and more fulfilling orgasm than I am used to.

As Jessica skillfully milked me, I had the sensation that I was coming for about ninety seconds, and it felt like my nuts were completely drained. At last, when it felt like she was done, I went to raise myself back onto my knees. Jessica arrested my movement by placing her other hand on my shoulder blades, thereby holding me in position.

"Stay where you are Papa," she teased. "We are not done with you yet."

I have never experienced anything quite like what happened next. My cock didn't really soften, remaining in a semi-hard state as Jessica continued to caress my prostate. It felt like I was having an extended, albeit lower-intensity orgasm for several minutes as I continued to expel semen into Casey's mouth. After what seemed like an eternity, my cock finally went flaccid, and Casey released me from between her lips. My penis hung limply between my legs, still dripping semen as Jessica continued to milk me.

"Now you may get up on your knees, Papa," she whispered, as she withdrew her middle finger from between my butt-cheeks.

Once I was on my knees, Jessica knelt beside me, and extended her finger towards Casey's mouth.

"Suck this, Casey," she ordered the young Asian, as she forced the soiled digit between the bewildered girl's lips.

Even though both girls were brand-new to my house, they had arrived separately, with Jessica showing up three hours before the young Asian. Casey had no way of knowing this of course, and presumably under the assumption that Jessica had seniority over her, and deferring to Jessica's more dominant approach, Casey obediently sucked the finger that had just been inside my asshole. I could tell that she found the whole notion disgusting, but she complied none the less. Once Jessica was satisfied that her middle finger was sufficiently clean, she dismissed the Asian girl.

"I will come and find you if we need anything else from you," she said assertively, as Casey obediently excused herself.

Once we were alone, Jessica laid on her back, her lips positioned right at the tip of my cock-head. Looking up at me with her beautiful green eyes, she smiled and offered herself to me again.

"You probably need to pee again, Papa," she said with a giggle, her eyes twinkling mischievously.

As I processed her words, she slipped her lips over the end of my cock, and lay there motionless, inviting me to empty my bladder inside her warm mouth. As it turned out, I did need to take a piss, and I ended up urinating in Jessica's mouth for several seconds, until my bladder was empty. After she swallowed the last few drops, she cheerfully rose from her prone position.

"I know," she said with a smile. "Go and brush my teeth. Let me know whenever you get the urge to pee again. See you later, Papa."

Chemistry is a funny thing, because despite Jessica being fairly average in the looks department, and certainly not resembling my stereotypical blonde hair, blue-eyed bimbo, I found myself thinking about that green-eyed redhead, for most of the day.

Being Judgement Day, it was an exceptionally satisfying and sex-filled period for me, as the girls pretty much laid everything out in an attempt to avoid being culled. At some point I kind of lost track, but I think I ended up blowing my load nine times that day.

Inexplicably, after each orgasm as I lay panting in my post-orgasmic glow, Jessica showed up to see if I needed to use the restroom. At this point, considering that she had brushed and flossed her teeth, and gargled some fresh peppermint mouthwash after each use, I pondered the fact that she was probably cleaner than my own toilet, and so subsequently decided to take her up on her offer, pissing down her throat five times during the course of the day.

We fucked again that afternoon, although when I was ready to climax, Jessica called Casey back in to my bedroom, and I finished inside the young Asian's anal passage, doggy-style, as Jessica massaged my prostate.

Apparently now aware of her place in the hierarchy, Casey waited until I removed my cock from her tight asshole, and then without any further prompting, willingly performed ass to mouth, sucking my cock clean. She had apparently given herself an enema shortly after entering my house, as an anal-cleanser and the accompanying instructions were part of the welcome package that the girls received.

After ensuring that my cock was completely clean, Casey waited patiently on her knees and Jessica slipped the soiled middle finger that she had used to stimulate my prostate, into the young Asian's mouth.

I, of course, hadn't even remotely considered cleansing my anal passage, and as Casey wrinkled up her nose at the foul taste, Jessica and I shared a laugh at her expense.

"You won't make it Casey if you telegraph your feelings that way," Jessica said quietly. "This very generous man saved you from the streets. When you get to taste his ass you should act like it is an absolute honor to do so. Why don't you put a smile on that cute little face of yours?"

After absorbing and following Jessica's directive, Casey's face lit up in a broad smile as she continued to suck the soiled finger.

After the three of us had showered, I found Olivia, eager to share my thoughts about Jessica with her. Within just a few hours of her entry into my house, she had made quite an impression, showcasing her resourcefulness, leadership and insane prostate massage skills. As Olivia and I huddled, my trusted friend revealed more about Jessica.

"In her intake photo she had long red nails," Olivia informed me. "They were a little ratty from being on the streets, but they were definitely much longer than they are now."

"You mean she cut them after she got here?" I asked. "I wonder why?"

"She asked me a lot of questions about your sexual preferences," Olivia began, putting two and two together. "I told her that your favorite activity was rim-jobs, and she asked me if you had ever been milked before. I responded that I didn't think so, which presumably emboldened her to cut and file her fingernails, to ensure that your prostate massage was comfortable."

"Impressive," I said with a smile. "Jessica is fast becoming one of my favorite girls."