Trust Fund BabybyJamesSD©
When I first heard about the Paris Hilton sex tape scandal my thoughts drifted immediately to an unmarked VHS tape that sits hidden deeply in the back of my closet. A tape that contains similar activities between myself and the daughter of wealthy parents, although admittedly of a far less recognizable name than Hilton. Although she's no heavy partying socialite like Paris, my co-star does stand to inherit her own sizable fortune. In many ways the tape chronicles a strange four month period in my life.
I was a few months out of a serious relationship, and ready to start dating again. Lacking any immediate prospects from more conventional outlets, I decided to try my luck at internet dating. I had a series of mediocre dates and a few painful encounters that aren't worth relating. However, Robyn was a different story.
From her profile Robyn was 5'3" with green eyes and long dark curly hair. She was extremely cute, with a petite nose and round cheeks. Her smile was lovely, two rows of perfectly straight white teeth. She described her body with the amazingly vague term "average" that I've found can mean anything between "buff but I don't want to sound stuck-up" to "quite overweight" and even actually "average".
The contents of her profile were rather sparse and lacking detail. She described herself as politically moderate, enjoying movies and dining out, and as a non-smoker. She was twenty-two, a year younger than me, and a college student. I didn't feel I knew much about her from it, but her picture was cute enough to see if there were aspects of her personality that didn't come through online. I sent her a quick message introducing myself, pointing out a couple things I liked about her profile. I invited her to check out my profile and write back if she was interested.
Such messages have a low response rate, but in Robyn's case she wrote back a couple days later. Her e-mail was brief, explaining she wasn't really into e-mail or instant messaging but gave me her phone number if I wanted to call her. I called her that night, and we shared a pleasant conversation that was less awkward than I expected. She laughed at my jokes and seemed like a sweet young woman. I detected a hint of an East Coast accent on her, but she said she was born and raised in California, though her parents were from the East Coast. I asked if she wanted to get together for drinks that Thursday night, and she agreed.
Robyn looked even more appealing in the flesh than in her picture. Her smile was just as pleasant, and her body was nicely feminine, with medium sized breasts, an average sized ass, perhaps a few pounds heavier than her "ideal" but still very attractive. I'm in decent shape but no model myself, so I find such minor flaws attractive. Her outfit was nice, jeans that clung to her nicely without looking uncomfortable and a feminine top that wasn't too revealing. She wore a bit more make-up than I prefer but I was willing to look past that.
The conversation flowed easily, and she obviously enjoyed my sense of humor. She casually touched my hand or leg when talking to me, which I occasionally reciprocated. Essentially it was proceeding like an ideal stereotypical first date. I found it a bit odd when she mentioned that she'd never had a serious boyfriend, but that is sort of understandable considering that college often has more of a "hook-up" atmosphere. I also have a good deal of respect for women who are capable of being on their own for a while.
She admitted to having an early class the next morning and I told her I had to work the next day. We decided to call it a night. I excused myself to take a leak, and Robyn was still in the women's room when I finished. I asked the server for the check but she informed me my friend had already paid the bill. It was probably only thirty dollars of drinks at most, but it was still a bit odd for me to have a woman treat on a first date.
"Thanks for paying for our drinks," I mentioned to Robyn while driving her home, trying to sound casual.
"No problem," she replied nonchalantly. "My parents give me some "emergency money" every month and I'm happy to pay. I hope I didn't offend your sense of masculine pride or anything, I just know you probably don't make a lot as a teaching assistant."
"Right on," I responded. It was a little weird, but I figured I was a progressive enough guy not to complain about my date picking up the bill. I've heard more than one woman talk about not wanting to "owe" a guy anything by letting him pay.
We chatted a bit more in front of her house. Admiring her for a moment, I leaned in and kissed her. I was relieved when she reciprocated eagerly. After a few minutes of lip-locking I asked, "Can I see your place?" hoping to continue our session on her couch and perhaps let things get a bit heavier.
She hesitated and told me, "My roommate is probably already asleep, and we both have early days tomorrow. But maybe we can hang out again this weekend if you're not busy."
"I'd like that," I replied. "Is Saturday night ok with you?" She nodded, kissed me once more, and went to her door, waving before stepping inside. I felt almost giddy after our successful first date.
Saturday's date went well. Continuing our almost stereotypical dating pattern, we had a rather conventional dinner date. We talked about our families, and I learned that her mother didn't work and her father ran a business. She was evasive when I tried to probe further. I dropped it and switched to talking about my own family.
I also learned that she was Jewish although non-practicing, which didn't surprise me in hindsight. Given my Midwest upbringing I don't tend to recognize the usual traits. She had no brothers or sisters, and was rather jealous that I had one of each.
When the topic of sex came up I discovered her attitudes were a bit more liberal than I'd imagined. She felt that people should be able to do whatever they please behind closed doors, as long as everyone involved enjoys it. She elaborated to say that partners should be willing to try something just to please their partner unless it really causes them pain or distress.
"After all, I hope he'd be willing to do the same for me, and plus you never know what you like until you try it."
Before we ordered I said, "I insist that you let me treat you, after you were so generous to pay for drinks the other night."
"Ok, you can pay for dinner, but why don't you let me cover the drinks again?"
I agreed that was fair, and she picked out a bottle of wine that ended up being quite tasty. When the bill arrived, I saw the wine was $80, more than the cost of both our meals. She didn't bat an eye, casually taking a hundred dollar bill out of her purse and placing it on top of my credit card. I considered saying something, but chose to let it slide once more.
Money peculiarities aside, between the wine and looking at the pretty girl across from me I was feeling rather horny and hungry for at least a make-out session.
"Want to come see my place and watch a movie or something?" I asked her.
"Sure, that sounds good," she replied.
I don't remember what movie she picked from my collection, only that we were making out on the couch five minutes into it. She was as much the aggressor as I, grinding her clothed body against mine as our tongues and mouths intertwined.
"I think your bed would be more comfortable" she said after almost twenty minutes of blissful kissing. I agreed silently and led the way to my queen sized bed.
On the bed the clothes started coming off, and soon she was down to her matching stylish bra and thong panties and I was still in my jeans and boxer shorts. In a heated moment I reached to remove her bra, but she stopped me, and suddenly tensed up and moved away.
"What's the matter?" I asked. "Is this too much? We don't have to do anything you don't want to."
"No… its ok. It's me," she almost whispered.
"Ok," I said, just holding her for a moment.
"I'm sorry my boobs are so small," she said, which shocked me. I'm pretty good at guessing cup sizes, and put her at a medium B cup. They were certainly enough to play with and find attractive, not to mention show through a shirt.
"They're lovely," I said reassuringly.
"That's sweet of you to say," she replied, not convinced. "I wanted to get them done when I had my nose job, but my dad wouldn't pay for it. My mom argued with him, and they got in a fight. I mean, she had hers done shortly after they got married!"
I was a bit confused. I supposed her nose was a little too "perfect". But I knew she didn't need fake tits, and was glad she hadn't ruined her lovely real ones. The idea of her rhinoplasty did put me off a little. I decided it wasn't really fair to judge someone on the basis of them wanting to look good. I just hoped her reasons for having a nose job didn't step from any sort of deep insecurity issues.
"Let me show you what I think," I said.
"What you think of what?" she asked softly.
"How lovely I think your boobs are," I replied. I guess my statement sounded sincere to her, because she slowly removed her bra, facing away from me. I reached around her, pressing against her bare back and kissing her neck. I cupped her breasts gently, caressing them and feeling their softness. After a few minutes I rolled her onto her back and took in the sight of her bare breasts. She really did look sexy topless, and I let her know how good she looked to me.
My compliments had a very positive effect on her. After licking and sucking her tits for a good while she pushed me onto my back and kissed down my chest. She undid my pants and pulled them off along with my boxers. As my sizable erection sprung into view she smiled slyly and asked "Are you sure you're not Jewish?" before eagerly crawling between my legs and taking it in her mouth.
Her blowjob skills were amazing. Her mouth was perfectly wet and accommodating to my cock. She treated my dick like a treasure, worshipping it with her mouth, and maintaining a lot of eye contact while doing so. She alternated between sucking and licking, and even managed to take most of my length into her mouth and partway down her throat.
"That feels soooo good. You may have to stop, unless you want me to… finish," I told her rather awkwardly.
"It's ok. I want to make you feel good. You can come in my mouth." It was pretty blunt, and very sexy to hear her say. I moaned when she placed her mouth back on my dick. After a few bobbing sucks, I groaned loudly and spurted into her mouth. She was caught a bit by surprise at the suddenness but didn't stop, taking all my seed in her mouth. She looked up at me and swallowed my load, cradling my dick and licking it clean before sliding her body back up mine and cuddling up against my side.
"You taste nice," She said. "Much better than most. And you cum a lot. I like that." I was in a state of bliss and a bit in shock at how this girl who had seemed somewhat proper had turned out to have a wonderful naughty side to her. I couldn't help wondering where she had learned to give such good head.
"That was amazing," I said.
"Thanks. I've practiced," she replied, and I chuckled.
"What was with the Jewish question earlier?" I asked her.
"Oh. Well, you know, Jewish guys, they stereotypically have big…" she trailed off, blushing attractively.
"Ah. The stereotypes you don't learn when you grow up in the Midwest," I replied.
When I'd recovered a bit I made a move to return the favor by rubbing my hand against her pussy through her slightly damp panties. She stopped me, kissing my lips gently.
"I'm glad you enjoyed tonight. I had fun. You can take care of my needs next time," she told me. I tried to protest but she wasn't listening.
"I'm going to go home now. It was fun sucking your cock, but I'm not ready to have sex just yet. And I know if I stay I'll be tempted. Because yeah, that's a really nice schlong you have, and if you fuck as well as you kiss I'm sure I'd be in for a real treat."
I was astounded. This girl was certainly pushing all my buttons to make me want her more.
"Call me the next time you want to hang out. I hope it's soon," she said once she'd reclaimed her clothing and redressed herself. She kissed me one last time, gave my still semi-hard dick a fond pat and showed herself to the door, leaving me slightly dazed but very content.
I called her cell that Tuesday night. Three days seemed the right amount of time to neither seem too eager nor disinterested. She sounded happy to hear from me.
"Would you like to get together sometime this week?" I asked.
"This week is really going to be a tough one, I have a paper due Friday morning. But after that I'm free. Oh wait, I told my parents I'd house sit for them this weekend. Hey, do you want to come along? I mean, it's ok if you don't want to."
"I definitely want to hang out more, and it's cool you'd do that for your parents. Should I meet you there?"
"They live up near L.A. actually. So maybe we should carpool. But I'll be there all weekend. It's up to you, but you're welcome to crash if you have nothing else going on."
"Yeah, I'd be happy to keep you company." It was a bit unusual to spend a weekend together at her parents' house so early in the relationship, but I figured this was an obvious invitation for sex. After our make-out session and her blowjob I was extremely eager to take things to the next level.
She drove, and picked me up in what appeared to be a practically new crimson SUV. The seats were brown leather and the interior looked loaded with options. I glanced at the odometer which said the car had 15,000 miles on it.
"Graduation present," she said in answer to my silent question. I remembered how my graduation present had been a five hundred dollar check, which was rather generous for my parents. I felt a bit of jealousy, and wondered what sort of company her father ran.
The conversation on the drive up was fun and light. The topic of sex didn't come up at all. There was a bit of traffic on the I-5 freeway going north, as there always is, but we made the best of it discussing movies and literature. She had worn a short frilly skirt that exposed a wide expanse of thigh, the view of which made the drive both more enjoyable and teasing for me.
Her parents' house was a good distance away from the freeway. It involved taking a number of winding roads up and down hills that quickly threw of my sense of direction. We drove through a neighborhood dominated by large fences that obstructed seeing into the lots except through the front gates. She pulled up to a keypad at one gate, entered a code, and the gate swung open.
From the car and how easily she threw around cash, I had already started to suspect that she'd understated the kind of money her dad made. However, seeing their house in person was still a shock. Calling it a mansion would be an overstatement, but it certainly was large and while tasteful, the telltale signs of disposable income were everywhere from the landscaping to the multi-car garage. Robyn pulled into the space third from the house and I helped her carry our bags inside.
My senses were overwhelmed upon entering the house. The garage led into the living room, which had a projection TV and a large, comfy looking leather wrap-around couch. There was a fireplace as well. To the left was a dining area and a very modern looking kitchen. The house was decorated very tastefully, but didn't look tremendously "lived in".
Robyn opened the fridge and peeked inside. "It's slim pickings, but usually mom buys me some frozen pizzas when I house sit. We'll have to go to the store tomorrow. I should give you the tour!" she said, excitedly.
The ground floor had a workout room and a home office for her dad that she never went into. In the backyard there was a decent sized in-ground pool with a connected hot tub that probably could seat four people comfortably. I finally asked what company her dad ran. She told me a name I didn't recognize. "They're mostly in distribution of raw materials. It's pretty boring actually, but Daddy founded the company himself and now it's one of the biggest in the sector." Robyn's tone was neutral as she discussed her father's job.
The upstairs was just bedrooms and bathrooms, and the tour culminated at her bedroom. "Don't laugh" she requested before opening the door. Robyn's room was quite girly, dominated by the color pink. She had a lot of stuffed animals and pillows on the bed. I also noticed a large number of plaques and certificates on the wall and trophies on her dresser.
"My mom puts all those up," she said somewhat dismissively.
"You obviously are quite the bright young woman, but I knew that already. Very accomplished too." She flashed me a dirty look before realizing I wasn't teasing her and then beamed at the compliment.
Robyn lay down on her large bed and I took off my shoes and joined her.
"So… what do you want to do now?" Robyn asked.
"I have a few ideas," I replied, climbing on top of her, shoving a few pillows aside to make room.
We kissed passionately, grinding our bodies against each other through our clothes. I cupped her breasts through her shirt, gently squeezing the nipple through the fabric, eliciting a gasp of pleasure. She wrapped her legs around me and pulled my hips more firmly against her crotch.
All too soon she interrupted me, gently pushing me off her. I allowed her to squirm out from under me. She looked terribly cute in her disheveled state.
"Come here," Robyn said, reaching for my hand. "I want to show you something." I accepted it and stood, following her out the door and down the hallway. She smiled at me excitedly and opened another door revealing another bedroom of sorts.
Robyn flipped a switch and suddenly the room was very bright. Four large reflective lights, similar to those I'd seen used for movies and photo shoots stood a few feet away from the king size bed in the center of the room. The bed had a bunch of overstuffed pillows on it and what looked like deep purple satin or velvet sheets.
There was a video camera on a tripod pointing at the bed. It was much newer than the one my father bought to videotape graduations and other events, but he'd purchased that back when I was in high school.
"Do you like it?" Robyn asked looking at me excitedly. "My dad gave me his old camcorder when he bought a digital one. Why don't you take a look at it?"
I was indeed curious and inspected the camera at her suggestion. Robyn hopped up onto the bed. "Turn it on!" she said with a giggle.
"Do your parents know about this room?" I asked her.
"My mom might, but she doesn't ask questions if she might not want to know the answer. I doubt my Dad has set foot in the upstairs of this house for a while," she answered.
I turned the camera on and she began striking model like poses for me to film. At first she was very silly, giggling as I stood still, mostly silent. Then I began directing her and getting into the spirit of the "modeling".
"Great, that's beautiful," I told her. "Ok, now lie on your stomach. Good. So, what's this room for?" I asked, the camera still recording.
"Well," she said with some hesitation, "this is sort of my own little movie studio."
"I see. And what sort of movies have you made here?" I asked, my cock hardening in my pants.
"To be honest I haven't really made any yet, except for a couple test shoots on my own. Honestly, I hadn't found the right co-star before now."
"Oh? And you think you've found him?"
"Oh yes. You see, deep down this daddy's girl wants to be bad. And while she never would actually star in a porn film, there's no reason she can't make her own." She struck a provocative pose, licking her lips slowly.
"Well you certainly have a pretty face, but I'll have to see if you have the right attitude for adult entertainment," I said, getting into the spirit of the fantasy. I kept the camera focused on her face as I interviewed her. "So what makes you think you can be the next great porn star?"