Trust Fund Baby Pt. 01

"Let's go to your place," she said suggestively, "if I am not being too presumptuous."

I tried to play it cool, trying to remind myself that I was a catch, but Madison was just so incredibly sexy and so completely out of my league, that I heard myself stammering over my words.

"One drink," I said in a quivering voice, "then I will run you home."

When we pulled into my triple garage, I helped Madison out of the car, and I noticed that she took a quick inventory of my toys, assembled neatly in the cavernous space. I had a new Harley-Davidson Fat Boy, a Kawasaki Z1400ZZR, a jet-ski on a matching trailer, surfboards, snowboards, skateboards and various other accoutrements that you would expect a teenage boy to lust after. My Ford Raptor was also parked in the garage, the workhorse to transport my toys to the beach, lake or mountains.

I led Madison through the garage and into my spacious living room, with its wall of glass. This thirty-five foot wide, floor to ceiling wall of glass panels provided an unobstructed view of the Pacific Ocean, although at night it was just a large black expanse, that provided sufficient privacy that I didn't need window coverings.

If Madison was impressed, she never showed it. I imagine a woman of her caliber, only ever went home with multi-millionaires, so my place was probably fairly standard. She may have noticed that once we were alone, I was out of my element. She was by far the oldest, most sophisticated and most desirable woman I had ever been alone with. I had seen enough romantic movies, to know to dim the lighting and put on some cool music, but beyond that I was in uncharted territory.

I thank the millennial generation for changing women's attitudes to dating. As the character traits of millionaires evolved, and more and more dot.com geeks became wealthy, the dearth of take-charge Alpha males forced women to evolve. Madison had done that, and was very comfortable taking charge of our situation.

For some inexplicable reason, I put on Madness, which while it possesses some worthwhile musical attributes, is hardly music to make love to. Madison approached my vinyl collection, amassed as it was in several milk-crates, and selected Lionel Richie. Once the more appropriate mood music was playing, she dimmed the lights, and moved towards me.

I was captivated by this beautiful woman and would have done whatever she wanted, so when she asked me to kiss her, I responded immediately. Madison and I kissed for the duration of Lionel Richie's, Can't Slow Down, my cock throbbing in my jeans the entire time. She was a great kisser, and alternated between French-kissing me and caressing my ears and neck with her lips.

When the album ended, she moved seductively towards my vintage turntable, dropped to her knees in front of the milk crates, and looking back over her shoulder through her bangs, whispered.

"So, what are you in the mood for?"

A more experienced man would have taken her signal of availability for what it was, but I was eighteen, had few sexual encounters to speak of, and was totally intimidated by this gorgeous older woman. Madison had her own agenda, and, like a chameleon, adjusted to her surroundings. She put on some smooth jazz, and beckoned me over with one finger.

She remained on her knees as I approached her, my erection visible in my jeans, telegraphing my desire for her. My pre-cum was flowing freely, and I could feel a wet spot in my underwear. Once I reached Madison, she extended her perfectly manicured hand towards my crotch, and began to caress my cock with her nails. I looked down at her, desire written all over my face, put one hand on the side of her face, and gently caressed her cheek.

Madison turned her face towards my hand and opening her peach-glossed lips, began to suck my thumb. She looked up at me with her large blue eyes, and smiled as if to signal her availability. I still didn't respond in a take-charge manner, and after giving my cock a quick nibble through my jeans, Madison stood up, grabbed my hand, and led me into my master bedroom.

We made out with more urgency now, Madison becoming aroused enough to dry-hump my leg as we kissed. At one point she pushed me on to the bed, and as I sat on the edge of it, she straddled me and mounted me. We dry-humped for a couple more songs, the wet-spot in my underwear expanding and appearing in the front of my jeans.

Madison was getting increasingly turned on, as she ground into me while sitting astride me, and my confidence was growing as she appeared to approach orgasm. We kissed passionately, and fucked each other through our clothes until Madison erupted in a very vocal orgasm. I hadn't witnessed a girl getting off before, and I was surprised at how easy it was, and how communicative she was about her needs.

After she came in my lap, Madison rested her forehead against mine, locked eyes with me and spoke softly.

"That was incredible baby, you really turn me on. I want you inside me."

With that she kissed me gently on the tip of my nose, dismounted me, and pulled her dress off over her head. This was the first opportunity I had to check out her body, and it was every bit as phenomenal-looking out of her dress, as she had appeared in it. She was wearing a peach half-cup bra, that was doing a great job of showcasing her perky breasts, a silk peach garter-belt and matching panties, and some expensive looking peach stockings.

As she stood before me in just her lingerie and her Louboutins, I couldn't help but admire her lean, toned form. She really looked like a lingerie model. I had gone shopping once with a old girlfriend and we had stopped into Victoria's Secret, to buy her some flannel pajamas. The sales assistant had given my girlfriend a catalog, and she had discarded it when we got back to her mom's house. I dug it out of the trash when she took a shower, took it home with me, and jerked off several times over the following week, to pictures of women that looked and dressed almost identically to the way Madison appeared in front of me.

Once Madison was half-naked, she turned her attention towards me. She leaned over me as I sat on the bed, her perky boobs trying to bust out of the half-cup bra. She placed her dainty hands on my upper-thighs and slowly moved my legs further apart. Once I spread them, she knelt between my thighs, and reached for my zipper. I was powerless to stop her, enraptured as I was by this beautiful woman. Madison undid the top button of my jeans, and slid the zipper down.

"Lift your butt up," she said, flashing me a broad smile.

I shifted my weight off of the bed, and she removed my jeans in one continuous motion, tossing them playfully over her shoulder.

"Again," she instructed, as she stuck her thumbs into the waistband of my undies.

As I lifted my ass up from the bed a second time, she deftly removed my briefs. She held them up in front of her face, as if to examine the wet spot.

"Someone is excited," she exclaimed with a giggle, stating the obvious.

I had been in this situation a couple of times before, in a partial state of undress, with a raging boner, hormones dictating the flow of events. However, in my prior encounters, the girl had remained in her underwear, choosing to satisfy my desire with a handjob. I had exploded all over her wrist a few moments later, inhaling her cheap perfume and trying to avoid any eye-contact with the eighteen year old virgin.

This re-enactment with Madison, was how I had hoped it would really happen. She had no intention of finishing me off with her hand, was wearing decidedly expensive perfume and was maintaining eye-contact with me, to keep me fully engaged. Fully engaged I was too, having never wanted to be intimate with a woman more than I wanted Madison.

She knew it too. Not from the obvious physical signs in front of her, my leaking teenage cock, my ragged breathing or the desire in my eyes. She could see beyond that. I had never kissed an older woman before, and more than anything else in the world, I wanted more.

"Madison," I whispered desperately, "You are so sexy."

"Let's make love, baby," she responded, helping me to my feet.

Once I was standing, I felt a little self-conscious. I had a huge erection and I was leaking profusely, acting every bit like the eighteen year old boy that I was. Madison seemed amused at my adolescence, and taking control of the situation grabbed the tip of my cock and pulled me towards her. We kissed tenderly and she pulled me in tight towards her. Her silk garter-belt brushed my cock-head as we embraced, and I left a trail of pre-cum across the expensive lingerie.

"You seem like you are ready to come, baby," Madison teased. "How do you want me?"

My mind was spinning as I tried to visualize Madison in different sexual positions, but once again my youth and inexperience got the better of me, and being slightly intimidated by the older, and clearly more experienced woman, I clammed up. Madison was already removing her tiny thong panties, and when I didn't make my selection, she got up on my bed, and adopted the doggy-style position.

"Arch my back?" she offered, as she looked over her shoulder at me with her baby blue eyes.

I nodded my approval without actually saying anything, and Madison faced forward, shook the kinks out of her hair, arched her back and waited patiently for me to enter her. She looked absolutely phenomenal, every bit the lingerie model from the catalog that I had jerked off to. My cock danced around between my legs as I scooted up behind her, the anticipation of getting inside her tight pussy driving me crazy.

At the last moment, I remembered my uncle's words, and despite being fixed, I asked Madison the all-important question.

"Are you on birth-control, Madison, or do I need to grab a condom?"

"Oh, we are good," she said dismissively, "come on, just slip it in."

Our agendas had collided by this point, my desire to fuck her brains out with little concern for impregnating her, due to my recent vasectomy, and her desire to trick me into impregnating her, by pretending to be on birth-control. She had no clue that I had her number, and even though I felt a strong attraction to her, I resented her game, and just wanted to fuck the crap out of her.

I scooted closer to her ass, and grabbed the tip of my cock. In my defense, I was eighteen years old, sexually inexperienced and suddenly thrown into the deep end of the dating pool, by virtue of my massive trust-fund and my bright orange Lamborghini. This was never going to be a protracted seeing-to, and we both knew it. I just wanted to get my rocks off, and Madison just wanted my semen inside of her, hopefully impregnating her in the process.

I fumbled around behind her trying to ease my way in, my inexperience evident with every errant stab. I think at one point, my cock-head might have touched her rosebud, because she reacted with surprise, but seemed more than happy to accommodate me.

"Fuck my pussy first, baby," she implored me, as she looked back at me over her shoulder, smiling broadly. "After you come inside me, you can relax a while, and then fuck my ass if you want."

With that promise of future delights, she reached underneath us, grabbed the tip of my cock, and eased me into the entrance of her tight, wet pussy. I couldn't believe how tight she was. I didn't have too many other women to compare her to, but Madison felt just as tight as the two eighteen year olds I had fucked, one of whom was a virgin before I had sex with her. I couldn't understand how a twenty-eight year old woman, who spent her nights trolling the bars of Newport Beach, could possess such a tight snatch, and I was ecstatic about the prospect of getting balls-deep inside it.

Madison allowed me to enter her slowly, so that I could savor the moment. She knew exactly the affect she was having on me, and wanted me to enjoy every second of it. Her tight love-canal slowly adjusted to my invasion of it, but it felt like she was doing her Kegel exercises as we fucked. We both knew I wasn't going to last long, but neither of us cared. Even though our agendas appeared to be in direct conflict, they had converged and aligned at this point, with both of us wanting me to ejaculate inside her, albeit for very different reasons.

I only fucked her for about three minutes, before I cried out and blew my load inside her. To my complete surprise, Madison experienced another orgasm as we rocked back and forth together, the significance of which was lost on me, until I debriefed with my uncle.

"I love it that we came together," she exclaimed excitedly. "I feel like I have a really strong connection with you, baby."

Whether or not we were soulmates remained open for discussion, but I did feel connected to her, although not in any deep spiritual, philosophical or metaphysical sense. No, I just wanted to fuck her again. Being eighteen years of age, blessed with quite possibly the world's shortest refractory-period, and being in the company of such a desirable woman, got me hard again within a few moments.

Madison was apparently ready to go again, my inexperienced fumbling evidently having been more than enough to get her off twice already, and wet her appetite for more.

"Baby, you make me so hot for you," she enthused. "Let's go again. Work your magic and make me have another orgasm."

Even though I wanted to take Madison up on her generous offer, and fuck her in the ass, I was also encouraged by the fact that I was apparently an excellent lover. I wanted to get back inside Madison's tight pussy, lay the pipe to her, and watch that bitch squeal with delight.

For this reason, I put my own selfish needs aside, and decided to accommodate Madison's desire to have another orgasm.

"What position do you want to try next?" I asked, my confidence growing by the minute.

"I don't care baby," she said enthusiastically, "I just want you back inside me."

As the words left her mouth, Madison reclined on her back in the middle of my bed, stuck two of her impeccably manicured fingers inside herself, and began to masturbate. I had never seen a woman pleasure herself, and was transfixed by the eroticism of it. Madison started to stimulate her clitoris, and as she gazed into my eyes, she quickly approached orgasm.

As she got closer to the point of no return, she moved her fingers from her vaginal canal to her clitoris, rubbing it furiously with one hand, as she caressed her taut stomach with her other hand. I saw her stomach flex and tense as she approached her release, her abs visible, under her lean abdomen. She closed her eyes briefly as if she was lost in the moment, but then, as if to remember that she was performing for an audience, she opened them and stared lovingly into my eyes, as she orgasmed on her hand. Unbelievably, this latest orgasm seemed even more intense than the first two, and I wondered if female orgasms got stronger with each passing release.

I never got the chance to find out. Madison, opened her legs invitingly, and motioned for me to mount her in the missionary position. She was very wet the second time I slid inside her, although she had maintained her elasticity, and was still extremely tight.

"Fuck, yeah," I cried out, as I slowly entered her, "you feel so tight, Madison."

"Oh my god," she responded, "you have a large cock, you are completely filling me up."

I had never thought of myself as being particularly well-endowed, but as I considered her assessment of my penis-size, two things occurred to me. Firstly, Madison was probably the best judge of cock-size that I had met in my life, given the level of inexperience in my first two lovers. Secondly, I had only ever seen flaccid cocks on other men before, in the shower after gym-class or nestled in a pair of Speedos during swimming lessons. If Madison said I was hung like a horse, I had no reason to disbelieve her.

With that confidence-inspiring knowledge, I started to lay the pipe to Madison. I lasted a little longer the second time, during which Madison experienced several very vocal orgasms, shouting out my name with each crescendo. She seemed to know exactly when I was getting close, and she hugged me close, and began whispering in my ear.

"Fuck me, baby. You feel so good, I am close again. Let's come together again."

We did enjoy a shared orgasm one more time, Madison erupting seconds after I started to unload inside her. After I came, she started to kiss me and we stayed coupled for several more moments. She was a very tender kisser and I felt my cock twitch again, within the warm embrace of her pussy.

Madison ended up spending the night with me, and we both slept naked in my bed. I was erect most of the night, as might be expected from an eighteen year old boy who was lying inches from this incredible source of pleasure. My inexperience and general politeness prevented me from taking her again during the night, even though she was naked in my bed, available for whatever I desired.

However, first thing in the morning, as she felt my boner brush the back of her ass, Madison invited me to hop on top of her.

"Fancy a quickie before I have to go to work?" she asked, grabbing the end of my cock and positioning it at the entrance to her vagina, in an assumptive close.

"Quickie" was an accurate description of our morning encounter, as I emptied my nuts within a few moments of getting balls-deep in the sexy woman. Inexplicably, Madison enjoyed two more orgasms during our morning session, despite receiving zero foreplay and the whole thing feeling decidedly rushed.

"Oh, wow, baby," she exclaimed, after I had come inside her, "you really rocked my world. You are quite the lover!"

Madison had to leave for work shortly after I came inside her. I asked if she wanted to shower at my place and I offered her a ride home, but she declined both, opting to take a taxi home, and clean up there. I didn't think much about future plans with Madison, after her taxi pulled out of my driveway, although I did give her a crisp one hundred dollar bill, for her cab fare.

After she left, I made some coffee and chilled in my living room. I had a clear mind and an empty nutsack, and even dozed off a little in my relaxed state. Of course, being eighteen, it wasn't long before my little-head emerged from his slumber, and I had an erection again. My thoughts returned to Madison, and I wondered when I would see her again.

I busied myself around the house, trying to take my mind off of my erection. When I went to make my bed, I found Madison's silky peach thong-panties, discarded in my bed sheets. They were heavily scented, both with her expensive designer perfume and her vaginal secretions. As soon as I put them to my nose, I was overwhelmed with the urge to masturbate. I closed my eyes, visualized the gorgeous blonde in the doggy-style position, and jerked off thinking about her. Right before I came, I removed the intoxicatingly scented underwear from my nose, and blew my load all over them.

Madison had created quite an impression, and I ended up masturbating using her scented panties several times that day. By the time I turned in for the night, she was all I could think about, and her panties were pretty much ruined, soiled as they were with my semen. I considered washing them, but was cognizant of the fact that her scent would be eliminated in doing so. For this reason, I tossed them under my bed covers, hoping to keep them infused with her perfumed aroma.

The following day, less than forty-eight hours after I set eyes on Madison in the bar, she was all I could think about. I decided to hit the same bar again that night, in the hope of running into her. I was out of my mind with desire for most of the afternoon, and jerked off twice more using her scented panties.