Trust Fund Baby Pt. 15

"Were you really President of the Celibacy Club?" I asked. "Or was that a joke, too?"

"Towards the end of the semester it was a bit of a joke, Papa," she responded with a smile, alluding to the fact that she had lost her purity during this time.

At some point it became obvious that Jessie was here to seduce me, and while I didn't know exactly why she had chosen me, her intent didn't seem at all nefarious. As we both relaxed, the conversation became much more candid, and she spilled the beans on why she was here.

"I turned eighteen, a few months before graduation," she began. "I was a very inexperienced young woman, having attended an all-girls private school. As an adult, my parents gave me a little more freedom, and I started attending parties at the local college frat house. One night, after too many beers, I had sex with a college junior, which was a very dissatisfying experience."

"How so?" I asked. "Did he force you?"

"No, nothing like that, Papa," she assured me. "He just blew his load as soon as he entered me, before I had a chance to really even get wet."

"That happens a lot with young guys, Jessie," I said quietly.

"We exchanged numbers but he never called me," she continued. "Then about two weeks later I ran into him at another party. He was with another young blonde, and didn't give me the time of day. I know it wasn't the best decision of my life, but I had a few beers and I let his best friend fuck me in one of the dorm rooms."

"Was that any better?" I asked, trying not to pass judgment on the young girl.

"Worse," she whispered. "He blew his load inside me twice in twenty minutes, before hopping off to get another beer."

"Asshole," I muttered. "Did you at least get to orgasm?"

"I am not sure, Papa," Jessie admitted candidly. "I was wet the second time, but I don't know if I came."

As I processed her naivety, it occurred to me that despite her bravado, and sexual innuendo, Jessie Baldwin was an incredibly innocent young woman. Evidently, she had never experienced an orgasm, which was interesting for a woman of her age.

"You would know if you had an orgasm, Jessie," I assured her. "Trust me on that one. And you were wet because your partner ejaculated inside of you."

"I have never been able to talk to my parents about sex, and it was a taboo subject at my school," she admitted. "Going to an all-girls school, I never had any male friends, and the Celibacy Club had a hard-core policy when it came to being alone with guys. After my two random hook-ups, I went to the sexual health clinic, and as an adult, I was able to get birth-control without parental consent. Several days ago, my Dad found my pills hidden under my dresser and all hell broke loose."

"What did your mom say, Jessie?" I asked. "Did she stick up for you?"

"She is a hypocrite," Jessie said quietly. "She got passed around Newport Beach like a joint before she and my Dad got married. In her quest for a wealthy husband she sucked and fucked half of Newport Beach's eligible millionaires. My mom and dad argue about her promiscuous youth whenever they fight. Your name always comes up, too, Papa," she said with a smile.

"So, why are you here Jessie?" I asked, sensing that we had both lowered our barriers and were being truthful.

"Honestly, Papa," she began, tears forming in her eyes. "My parents kicked me out of the house. I am an authorized user on my Dad's credit card so I booked into a cheap motel over by Disneyland, and have been staying there for the last week or so. It is in a rough area, and I am scared to go out at night. I need to work and I know erotic dancers make good money. If you give me the opportunity to work, I can get myself back on my feet and upgrade my living arrangements."

"Are you still at the motel?" I asked, fearful for her safety.

Twenty years prior, I had employed Olivia to procure me fresh, young pussy from the streets of Southern California. I knew from first hand experience how quickly young runaways could exhaust their options, before resorting to exchanging sex for a warm place to land. As much as I hated Steve Baldwin, I didn't want any actual harm to come to his daughter, particularly as I still harbored hopes of one day being with Jody.

"I spent last night in my car," Jessie admitted. "I didn't sleep a wink though, I was so scared."

"Surely the motel was a safer option, Jessie?" I said, as I felt myself moving into a more paternal role with the frightened teenager.

"I did feel safer in the motel," she admitted, on the verge of tears. "However, after I made the decision to beg you for work, I called Olivia to ask her how to make an impression on you. She shared your preferences with me and I drove to Trashy Lingerie on La Cienega Boulevard and bought the cheerleader and schoolgirl uniforms. My dad must have freaked out when he saw the eight hundred dollar charge on his Visa, because when I stopped to get gas for my car, the credit card was declined. On my return to the motel, I was informed that I needed to find an alternate method of payment, because the Visa was declined. I have sixty five dollars to my name, so I came here looking for a life-line. I am desperate, Papa."

As tears began to flow down her angelic face, I arose from my chair and went to comfort her. I guess it was a testament to my maturity, that my focus changed from the subjugation of Jessie, to her protection. As the only daughter of my nemesis, it would have given me immense satisfaction to have stuck that eighteen year old goddess under my pleasure chair, and filmed her as she ate my ass. However, as she sobbed in my arms, all of my lewd intentions evaporated, along with my erection.

"Would you like me to take you home, and patch things up with your parents?" I offered. "Your mom and I go back a long way."

"Maybe in a few days, Papa," she whispered. "My dad is really hot about my most recent purchase," she said, as she gestured towards the Japanese schoolgirl uniform she was wearing. "He sent me some pretty hateful texts."

"Well you came to the right place," I said warmly. "I really loved your mom, at one point," I said ruefully, Jessie's uncanny resemblance to her mom, causing me to reminisce fondly.

Jessie Baldwin never danced for me that day, nor did we step foot in the VIP room. I had the feeling that I was going to regret my decision for the rest of my life, as it would have been the perfect opportunity to do everything that I ever wanted to do to Jody, to her clone of a teenage daughter. However, it just didn't feel right, so I gave Jessie some privacy, and she changed back into her expensive designer clothes, which felt like a step backwards, after what she had just been wearing.

I decided to put Jessie up at the Ritz-Carlton in Laguna Niguel, a private five-star resort about a fifteen minute drive south of Newport Beach. I could have taken her back to my house, but I didn't want to create any sense of impropriety, and I felt like the house-pets would be a bad influence on this innocent young girl. After checking her in to a nice suite, I left as I had two meetings that I didn't want to cancel at short notice. I promised Jessie I would return in the late afternoon, and we ended up having dinner together, on her secluded balcony.

It was actually nice to be in the company of a beautiful young girl, without the expectations of sex. Any time I spent more than ten minutes with one of my house-pets, I would end up busting a nut, in them or on them, but Jessie and I just chatted freely, and got to know each other.

Growing up economically advantaged, Jessie was comfortable in the luxurious hotel, and when we went to take a stroll through the magnificent hotel grounds at sunset, our time together felt very natural and relaxed.

In the early evening, we drove over to South Coast Plaza, and I treated her to some essentials, as her Dad had kicked her out with just the clothes on her back.

"I did have this in my car, too," she said sheepishly, as she brandished a light blue t-shirt with the words "Celibacy Club" embroidered across the front.

Despite showing up to my strip-club in designer clothes, Jessie had very simple tastes for the daughter of a wealthy man, and I bought her some jeans, some casual t-shirts, some toiletries and make-up, and a bathing suit, so that she could enjoy the hotel pool the following day.

"I need some underwear, too, Papa," Jessie told me as we walked around the huge shopping mall. "Some pervert stole mine from the laundromat when I went to get some more quarters from the change machine."

Her request was followed by a brief uncomfortable moment as I considered the logistics of buying her intimate apparel, but I suggested that she go inside and buy the panties, and I would simply pay for them when she had made her selection. I did feel like a bit of a voyeur waiting outside Victoria's Secret as she shopped, particularly as she came to the door several times holding a garter-belt, or a silky camisole up for my approval. Of course, being a man, I gave the thumbs up to everything, and by the time Jessie had finished shopping, she had three huge bags full of Victoria's Secret intimates. The whole bill cost about what Madison used to spend on one La Perla ensemble, and I was grateful that Jessie seemed to be low maintenance.

I must admit, the five hours that we spent together were totally enjoyable for me, as I felt like we were connecting on a deeper level, and I had completely suppressed the notion of having sex with her. My plan was to keep her safe in the hotel for a few days until Steve Baldwin cooled off, and then take her home and try and broker a peace deal.

Of course, as they say, the best laid plans of mice and men. When we returned to the hotel, I tried to say goodbye to Jessie in the parking lot, but she asked me to help carry her bags to her suite. I obliged, and the second we got to her door, she invited me in.

"One drink, Papa," she said sweetly. "And then you can go home to your house full of strays."

Because she was only eighteen, which is below the legal drinking age in California, she suggested that we order a bottle of wine from room service. I am not much of a wine drinker, preferring vodka on ice, so Jessie selected an inexpensive Chardonnay and room service delivered it to her suite.

I must clarify that my intentions were pure at this point, but one glass of wine turned into two, and before I knew it Jessie had called room service and ordered another bottle. The wine took effect almost immediately, lowering my inhibitions and heightening my libido. However, at some point in the evening, I decided it was time for me to leave.

"I am going to call an Uber, Jessie," I told the beautiful young girl. "I will get my car in the morning."

"Will you just wait until I shower, Papa?" she asked sweetly. "I won't take long."

It seemed like an innocent request, so I went out onto the balcony with the remainder of my wine, to enjoy the cool ocean breezes. I had a healthy buzz going, and was starting to feel sleepy, even though it was still only nine o'clock. Several minutes later, I heard Jessie singing inside the hotel bathroom, and was pleased to hear the change in her mood.

I must have dozed off because when I opened my eyes, I noticed that the lights were dimmed and Jessie had lit some candles. She had changed the music too, Ariana Grande having been replaced by Marvin Gaye. I got up carefully from my chair, fully aware that I was intoxicated. As I entered the dimly lit room, I noticed that Jessie was sitting on the edge of the King Size bed, and she was wearing some of her new lingerie and a pair of high heels.

"Come, Papa," she said, patting the bed right next to where she was sitting. "Sit with me, and we can call you an Uber."

I knew it was a bad idea the second I walked towards her, but the alcohol had diminished my judgment, and my cock had assumed all of the decision-making responsibilities. The second I sat next to her, Jessie leaned in and kissed me tenderly on the cheek.

"Thanks for a wonderful day, Papa," she whispered, as I took in her intoxicating scent.

I turned to face her directly, and our lips touched softly as we began to kiss. Despite her relative lack of experience, Jessie Baldwin was a very tender kisser, and her minty fresh breath invited me to ease my tongue between her lips. We french-kissed for nearly half an hour, the slow pace of our encounter seeming to ignite a fire within both of us, despite the twenty five year age gap.

Truth be told, I felt the exact same chemistry that I had experienced two decades ago with her mom, and it felt like I was making out with a younger version of the love of my life. I was erect the entire time that we kissed, and I could feel my pre-cum dampening my underwear. At some point, Jessie laid back on the bed, and invited me to get on top of her. We were still fully clothed, although Jessie was just wearing lingerie and her high heels.

We dry-humped in the missionary position for several minutes, and she brought me to the edge of climax a couple of times, before I rolled onto my side next to her. I started to kiss the side of her face, before moving my attention to her neck. As I licked and kissed her neck and shoulders, her level of arousal elevated significantly, and she began to moan softly. I teased her upper body for a few moments before lowering my lips to one of her erect nipples. Initially teasing her through the silky fabric of her peach colored camisole, Jessie wanted more and whispered to me as she arched her back in pleasure.

"Take my top off, Papa," she moaned, as she raised her arms up to facilitate its removal.

As I slid the silky garment up her outstretched arms, I admired her lean, taut abdomen. Possessing the same genetic traits as her mom, Jessie had a phenomenal mid-section, her abs visible beneath her tight, teenage skin. As I let her camisole slide to the floor, she raised her feet up onto her bed, and I heard her high heels hit the plush carpet of the bedroom. Jessie spread her legs slightly further apart, and I lowered my lips to her breast.

It had been years, possibly decades, since I last made an effort to pleasure a woman. I knew my way around the female anatomy, and possessed the skill to make a woman feel good, it's just that I didn't need too. Between the strip-club and my house-pets, I had more young pussy than I could handle, and the huge financial gulf between my lovers and I, ensured that I never hard to work too hard in any sexual encounter. Olivia would typically tell the young women that I enjoyed anal sex and rim-jobs, and they would accommodate my every desire, without expectation of reciprocity.

With Jessie it was different. I had been madly in love with her mom, a virtual addiction that took at least a decade to kick. Given the missed opportunity with her mom, Jody, I wanted this to be a prolonged encounter, from which Jessie emerged completely satisfied.

As I sucked her erect nipples and kissed her gently all around her areolas, she began to softly whimper, and it felt like I was really getting her excited, which felt incredibly flattering. Jessie had arched her back completely now, and her breathing was heavy and labored, as she writhed under my soft caresses. After I had teased her breasts for several minutes, I traced my tongue slowly across her abdomen, and watched as she tensed under the stimulation.

I licked and nibbled all over her stomach, stopping at one point to tease her inside her belly button, with the very tip of my moist tongue. I traced my tongue all the way down to the waistband of her silky panties, before stopping abruptly and repositioning myself on my stomach with my face between her upper thighs.

I could have removed her panties at that point, such was her obvious desire for me to go down on her. However, I continued to tease her, by licking and nibbling her inner thighs, stopping right when my tongue made contact with the silky underwear. Jessie was visibly wet by this point, the crotch of her peach colored panties noticeably darker than the front, and the scent of female arousal emanating from her pussy.

Jessie was in an elevated state of arousal, and I was determined to keep her on the boil. I began to lick her vagina through the material of her silk panties, which elicited soft moans of pleasure from her, and prompted her to put her hands on the back of my head. As Jessie ran her fingers through my hair, I pressed my lips firmly against her sex, and she finally broke down.

"Papa, please," she begged, "take my panties off."

The desperation was palpable in her voice, and I was aware that she was breathing heavily as I slid her panties down her slender, toned legs. I couldn't help notice that the crotch of her underwear was slick with her vaginal secretions, and after I tossed her intimates onto the floor, I lowered my face to her pussy, stopping just before I made contact.

"Papa, please," she whispered. "Go down on me."

It had been a while since I last ate pussy, but Jessie's reaction to my touch was so strong that it made me want to continue to pleasure her. As she grabbed a fistful of my hair, I hovered just above her vagina, and gently parted her labia with my hands, exposing her clitoris in the process. Breathing gently onto her clit, as she continued to moan softly, I waited several moments before slowly lowering the tip of my tongue, until it brushed against her sex. Jessie let out a whimper of pleasure, and feeling that I had teased her sufficiently, I slipped my tongue between the folds of her labia, and softly caressed her clitoris.

A few moments later, as Jessie arched her back, and cried out my name, she had a stupendous orgasm on my face, which, judging by her reaction, may have been her first. Jessie's orgasm lasted for almost a minute, and during the entire episode she thrashed around on the bed, tensing and flexing, her fingernails embedded in the comforter, as she discovered the pleasure associated with the female release.

After she came, Jessie exhaled sharply, and lay motionless on top of the comforter. A few seconds later she began to giggle and then she spoke.

"Oh my," she whispered softly. "I had no idea. That was fucking incredible, Papa. I have never experienced anything like that before. Thank you."

Once my suspicions were confirmed that this was her first ever orgasm, I realized that Jessie probably had no clue that women, not constrained by a refractory period, were capable of multiple releases. As she basked in her post-orgasmic bliss, I lowered my tongue to her clitoris and began to gently nibble it. In her elevated state of arousal, Jessie approached her second orgasm with alarming alacrity, crying out with pleasure as she climaxed on my face, less than three minutes later.

Jessie was even more appreciative after her second orgasm, but as my tongue flicked against her clit and she realized that she could go again, she began to verbalize her admiration.

"Are you serious, Papa?" she whispered. "I had no idea."

I ended up bringing Jessie Baldwin to climax five times that night, and after her last orgasm she whispered that she loved me, right before she drifted off to sleep. As I watched her sleeping peacefully, I was overwhelmed with emotion, and I tossed and turned in our hotel bed before I finally fell asleep.

I slept like a baby that night. As I listened to Jessie's heavy, contented breathing, my paternal instinct returned, and I spooned her as she slept.

Embarrassing as it was, when I awoke very early in the morning I was sporting an erection, and my hard-on was pressed against Jessie's back, my pre-cum having leaked all over her butt-cheeks. She was still asleep, breathing deeply, her pert ass defying gravity, as she was lying on her side. Had I awoken next to one of my house-pets in such an alluring and available pose, I would have applied a healthy dose of Anal-Ease to my morning wood, and butt-fucked the sleeping girl. However, as I watched Jessie sleep, I was filled with a strong urge to continue to pleasure her.