Trust Fund Baby Pt. 15

Lowering my lips to the base of her spine, I began to kiss her softly on her lower back. After a few moments Jessie stirred, rolled onto her stomach, and emitted a quiet moan of pleasure, as I traced my tongue across the top of her buttocks. I kissed and nibbled her perfect ass-cheeks for several minutes, elevating her level of arousal until I noticed that she had started to self-lubricate.

When I slid my tongue between her firm buttocks, she let out a whimper, and after raising her hips from the bed, she wiggled her ass seductively, thereby inviting me to enter her vagina from behind. Jessie maintained her elevated position as I scooted slightly lower and started to lick her pussy. As she moaned softly, she lifted her head from her pillow and slid it under her hips, so that she could remain accessible to me, without the effort of supporting herself.

The pillow elevated her in such a way to facilitate my entry into her teenage pussy, but I chose to remain with my tongue on her sex, as she started on her path to release. A few moments later, with her ass in the air, and my soft tongue lapping gently at her clitoris, Jessie had another explosive orgasm, crying out my name as she creamed all over the pillow.

I got Jessie off three times in very quick succession, before I removed my lips from her sex, and using both hands, parted her perfect ass-cheeks. She was trembling as I hovered above her rosebud, my warm breath giving her some indication of my close proximity to her third orifice. As I blew softly against her tight little asshole, she moaned in anticipation, and goosebumps appeared all over her buttocks and lower back.

After several moments of teasing her, I extended my tongue and began to lap away at the entrance to her ass. I knew from personal experience how pleasurable rim-jobs were, the myriad of nerve endings that terminate in this area making for an otherworldly experience when properly stimulated. I had enjoyed thousands of ass-eating sessions, and they were by far my favorite way to orgasm.

It was no surprise then when Jessie began to whimper contentedly, as I ate her perfect ass. As she began to breathe more heavily, I slid one hand under her and lightly caressed her clitoris. Between the combined efforts of my tongue and fingers, Jessie enjoyed three more orgasms on her stomach, before she exhaled deeply and told me that she was completely satisfied.

A few minutes later, as I gently massaged her lower back, I heard her heavy breathing, and realized that she had gone back to sleep. Again, I wouldn't have tolerated one of my house-pets drifting off to sleep before some kind of reciprocity, but Jessie looked so peaceful as she lay there in silence, so I got out of bed, and went down to the hotel lobby to get a cup of coffee.

It was still early in the morning, so I checked my emails, and caught up with the daily news, before deciding to go to the fitness center to work out. I have a daily exercise routine to keep in shape, but the Ritz-Carlton had such an impressive array of work-out equipment, that I put in a full hour, working up quite a sweat in the process.

Returning to Jessie's room, my plan was to take a quick shower, and then head back to my house. I had a completely unscheduled day, but wanted to give the young girl some privacy, so that she could absorb our impromptu sexual encounter. I was twenty five years older than her, after all, and wasn't sure if she had just got caught up in the alcohol-infused moment, or if she really found me remotely attractive.

Jessie had seemed to thoroughly enjoy our morning encounter, although she was fast asleep when I started, thereby unable to give her full consent. When I got back to her hotel suite, I was happy to see that she was awake, although she was still in bed, with a contented look on her face.

"Good morning, Papa," she said cheerfully, as I moved over to where she was reclining against a pile of pillows.

"Morning Jessie," I whispered, as I planted one tender kiss on her forehead. "Did you sleep well?"

"I think you know the answer to that question, Papa," she responded playfully.

"I am going to take a quick shower," I informed her. "I won't be long, and then we can grab a quick bite in the hotel before I leave."

"Ok, Papa," Jessie responded. "Whatever you want."

I kissed her once more on the top of her head, before excusing myself to shower. I was fully erect when I entered the large shower enclosure, having gone almost fifteen hours without release, despite the extreme sexual provocation of being in close proximity to this beautiful young blonde. I figured I would bust a nut the second I got home, using one of my house-pets as a cum-receptacle.

As the dual-headed rain shower unleashed a torrent of warm water onto my sweaty body, I heard the glass door of the enclosure open, and a naked Jessie Baldwin joined me.

The second that I saw her appreciative smile, I knew that she was planning to reciprocate. She looked so beautiful, her angelic youthful appearance evoking a tightening in my nuts, even as I was already fully erect.

"Last night was amazing, Papa," she gushed, as she immersed herself under the powerful shower heads.

Once she was wet, Jessie grabbed the plastic bottle of body-wash that was sitting on the shower shelf, and squeezing a large dollop into the palm of her hand, began to soap up my chest. The moisturizing body-wash lathered quickly as she rubbed it into my upper body, and repeating her motions she began to wash my abdomen. I made no attempt to hide my erection, and as she raked her nails across my lower stomach, we both knew where this was heading.

Despite her apparent sexual inexperience, Jessie had a very sensual touch, and having seemingly learned a thing or two from last night's slow, unhurried, teasing encounter, she really took her time. Once the front of my upper body was covered in the soapy suds of the body-wash, Jessie lowered herself onto her knees, and began to wash my legs.

I use the word wash loosely, as it does nothing to convey the sensual way that Jessie soaped up my legs and feet. It was more of a combination of a light massage, and a sustained raking of her nails, over the entire length of my legs, including the top of my feet. Occasionally, Jessie looked up at me from her kneeling position, to gauge my level of interest, her bright blue eyes twinkling with delight as she recognized that I was enraptured by her.

"Lift your foot, Papa," she said softly, as I placed one foot upon her lower thigh, and she began to tenderly wash it.

Jessie attended to both of my feet, soaping up between each toe as I stood over her, my erection jutting lewdly in front of my body, telegraphing my desire for her. My nuts ached in anticipation of my impending release, although I had no clue whether it was going to happen within the confines of that shower enclosure, or the second I got back to my Newport Coast mansion.

Once Jessie was satisfied that I was sufficiently lathered, she arose from her knees and washed the suds from my body. She still hadn't made contact with my considerable erection, although as her hands roamed freely around my inner-thighs and my stomach, she had come tantalizingly close numerous times.

"Turn around, Papa," she whispered, once the soap suds were removed. "Let me wash your back."

Jessie was a very inexperienced young woman, but as our encounter was unfurling at such a relaxed pace, she seemed to be gaining confidence with every passing moment. After I turned my back on her, Jessie rested her head on my shoulder, placed her lips against my earlobe and nibbled it gently.

"You are going to have to teach me everything, Papa," she whispered softly. "I have never pleasured a man before, but I am willing to try anything you desire."

I let out a moan as I processed her words, and I started to breathe more heavily in anticipation of what my release would entail. With her intentions clearly stated, Jessie applied some more body-wash to my shoulders and began to lather them up. She repeated the sensual combination of massage and nail raking to the entire back of my body, ending up on her knees with her face right behind my ass-cheeks.

I tensed up the second I felt her dainty hand slip between my buttocks, and as she began to lather up my undercarriage, I widened my stance slightly to give her more room to work on me. Using a perfectly light touch, Jessie thoroughly soaped up my nether regions, her hand gliding sensually over my asshole and taint, until her fingertips emerged from between my legs, and tenderly massaged my aching nuts.

I was leaking profusely now, something that just didn't happen to me any more. I used to leak pre-cum in copious amounts when I first dated Madison, as my youth and lack of sexual experience combined to ensure a steady flow of seminal fluids. However, now that I was in my forties, and had enjoyed several hundred different partners, I no longer tortured myself with the prospect of release. If I was horny, I found one of my house-pets or one of my erotic dancers, and used them as I saw fit. I never went a day without busting a nut, and often enjoyed several orgasms in a twenty-four hour period.

By contrast, I had spent nearly the last twenty four hours in the company of Jessie Baldwin, and while I had brought her to numerous climaxes through oral-sex and a tender rim-job, she had yet to offer me any reciprocation. To say I was ready, was a total understatement, and we were both acutely aware of it.

As Jessie massaged and caressed my nut-sack, I let out another whimper, and she responded by soaping up the shaft of my cock. After my cock was covered in the suds of the moisturizing body-wash, Jessie began to give me a very slow and sensual hand-job, one of her dainty hands moving up and down my shaft, as her other hand tickled my asshole.

Her cadence was perfect, not quite fast enough that I was in danger of ejaculating, but coupled with the attentions of her fingertips on my asshole, it was enough stimulation to keep me on the boil. I figured that my first cum-shot with this young goddess would be a hand-job, and I was fine with that. I didn't want to force her into anything or even rush her, due to her sexual inexperience, even though I routinely took the anal-cherries of any runaway that entered my home with that particular orifice still virginal. It just felt different with Jessie, and I wanted things to unfurl naturally, and at her pace.

After a few moments of a very sensual hand-job, Jessie removed both hands from my genital area, and slowly stood up. Remaining behind me, she grabbed the hand-held shower attachment, and rinsed my back off before inserting the attachment between my legs and washing off my asshole and taint. Once my back was free of the lather, she reached around to my front with the hand-held shower head, and washed the suds from my cock.

A few seconds later, as she remained standing behind me, she turned the water off, and for a split-second I thought we were done. I was breathing heavily now, and as the water flow slowed to a halt, the sound was quite noticeable. Jessie rested her head back on my shoulder and I felt her warm breath against my earlobe as she moved her lips to my ear.

"You are squeaky clean now, Papa," she whispered. "Would you like to teach me how to play the trombone?"

I felt my knees weaken at her provocative words, and I stammered my reply, as the anticipation was getting the better of me.

"Everything you just did was perfect, Jessie," I said quietly. "I like a slow, sensual touch. Please, take your time."

"Whatever you say, Papa," she whispered, as her lips left my ear.

My legs began to tremble as Jessie slowly traced her tongue from my ear down to the side of my neck, causing the hairs on the back of my neck to stand up. Over a period of several minutes, that little temptress teased the hell out of me, licking, nibbling and kissing all over my back and my shoulders.

When I felt her kneel down behind me, I assumed that she was ready to eat my ass, but Jessie had taken my pleas for an unhurried session to heart, and began to lick me behind my knees. She ran her tongue up and down the back of my legs, inching closer and closer to my ass-crack with each pass. Finally, as I felt her breath on my buttocks, she placed her manicured hands on my ass, and pulled my cheeks apart.

Analingus is definitely an acquired skill, and while I had experienced mechanically superior rim-jobs, the fact that it was Baldwin's daughter on her knees with her nose between my butt-cheeks, definitely added to the experience. Jessie had presumably done some research, because during her twenty minutes of ass-eating, she covered all of the bases. To begin with, she focused her attention on the underside of my nuts, extending her tongue fully so that she could lap away at them, as they throbbed and pulsated with every touch. Moving slowly to my taint, she peppered this sensitive area with light kisses, before changing things up with a nibble here and there.

By the time I felt her tongue circling the entrance to my ass, I was shivering with desire, the majority of my body completely on edge. Finally, after what seemed like an eternity of teasing, Jessie extended her tongue and slipped it through my sphincter, and I felt her nose come to rest just above my asshole. Once she was inside my anal-cavity, she reached around and began to caress the tip of my cock, using the palm of her hand to coat my pre-cum around my glans. I had expelled a significant amount of pre-cum from my cock-head over the course of her extended teasing session, and a long string hung lewdly from the top of my cock.

Reaching down, I scooped the thin rope of seminal fluid up in the palm of my hand, and coated my glans with it for additional lubrication.

Jessie removed her tongue from my ass, and spoke quietly.

"Am I doing it right, Papa?" she asked innocently. "Is there anything that I can do to make it more pleasurable for you?"

"Wiggle your tongue once you are inside me," I gasped, shocked at her desire to accommodate me.

"Ok, Papa," she responded. "Anything else I can do? Olivia said that this is your favorite way to come. Are you almost ready?"

As I weighed maximizing the enjoyment of my release, against respecting Jessie as a woman, I decided to speak up.

"I want to watch you rimming me," I said quietly. "Can we move in front of the bathroom mirror?"

"Whatever you want, Papa," Jessie said sweetly, as she got up from her knees.

We were both pretty much dry by this time, and the bathroom heater had created a warm and comfortable environment in which to enjoy each other. Exiting the shower enclosure, we moved to the large bathroom counter with its double sinks. Beautifully lit from above, the large wall was mirrored from the countertop to the ceiling, and there were two large mirrors on each side of the sinks, creating a three-sided mirrored enclosure, albeit only two feet deep.

"How do you want me, Papa?" Jessie asked innocently. "What will give you the best visual?"

As eager as she was to accommodate me, we ended up trying several different positions for the rim-job, settling on one in which I actually got up onto the huge marble countertop, and squatted over one of the deep sinks, with my back to the large mirrored wall. As I rested my hands against the wall to maintain my balance, Jessie scooted underneath me, head first. In this position, her naked torso was in front of me, her lean abdomen stretched taut as she arched her back.

Her long platinum hair hung into the deep sink, and once her tongue was at the entrance to my asshole, I lowered myself slightly, and squatted on her face. Using the side mirrors, I could now see the side-profile of her face, as she ate my ass. The additional visual stimulation was provocative to say the least, a girl less than half my age, barely legal in fact, draped backwards over the countertop, butt-naked as I squatted on her face. Jessie followed my directive perfectly, and as soon as her moist tongue slipped through my sphincter, she began to wiggle it around deep inside my ass.

With mirrors now surrounding me on three sides, and the naked teenager's limber body stretched out in front of me, I was assaulted by lewd visuals whichever way I turned, and I knew my release wouldn't take much longer. As Jessie tongued my asshole, I reached over and grabbed a bottle of baby oil, pouring a healthy amount of it along the shaft of my cock. Giving the bottle another squeeze for good measure, the excess baby oil dripped from my cock, and landed on Jessie's phenomenal pert tits.

She let out a giggle as the makeshift lubricant rolled down between her tits, before sliding down her tight abs.

"Can you please jerk me off, Jessie?" I asked her, as the combined physical and visual stimulation was getting the best of me.

I tried to last as long as I could, in case this ended up being the only time that Jessie ever got me off. However, the whole encounter was so lewd, so visually appealing, so exactly what floats my boat, that I felt my nuts constrict as soon as Jessie wrapped her dainty teenage hand around my cock, and closed it tightly into a fist. As she began to slowly jerk me off, I moved my head every few seconds, taking in the next, equally exciting visual.

"Right there, Jessie," I moaned, as she stumbled upon the perfect combination of grip and hand speed. "That is perfect. When I come, keep your tongue inside of my ass. You may feel some pressure on it."

Jessie mumbled some inaudible response, although judging by the fact that it was three syllables, and her most frequently uttered phrase, I can only assume she said, "Yes, Papa."

A few moments later, as I watched her perfectly manicured, peach-colored fingertips work their magic, I blew my load. I felt my nuts tighten first and then my sphincter, and as Jessie followed my instructions to the letter, the first rope of ejaculate was expelled with considerable force, landing all over her pert tits.

The resultant splat of my semen landing on her breasts caused Jessie to jump slightly, before she began to giggle. She kept wiggling her tongue around inside my anal cavity as she jerked me off, and a split-second later, I expelled my second rope of semen onto her naked body. Jessie tried her hardest to give me a fulfilling orgasm, and while I greatly appreciated her efforts, her inexperience was evident as she continued to jerk my cock even as it got sensitive. Resting one of my hands upon hers, I slowed her cadence to a much less frenetic pace.

"Release your grip slightly," I instructed her, as she relaxed her fist. "Men experience heightened sensitivity after they orgasm."

Jessie followed my instructions perfectly, and as I squatted above her with her tongue still inside me, she gently stroked my softening cock. Traces of semen continued to leak from the tip of my cock for several moments, dripping on to Jessie's breasts until they were glistening with my seed. She remained passively beneath me, tongue deep in my anus, as I recovered from the mind-blowing release.

I was expecting a period of awkward silence after I dismounted her face, but Jessie's reaction was anything but. As I helped her up from the countertop, she was beaming with what appeared to be pride.

"How did I do, Papa?" she squealed excitedly. "Any tips for improvement?"

"That was amazing, Jessie," I told her. "Was that your first time?"

Nodding her head appreciatively, she assured me that she had never done anything remotely like that before, and as I processed the fact that Steve Baldwin's baby girl had just eaten my ass, I broke into a huge grin. Grabbing a blue t-shirt that was hanging on the heated towel rail, I started to wipe my ejaculate from her tits, before she burst into laughter.