Looking back I guess I'd had a crush on my sister from grade school. She is a few years older and when I was just beginning to enter the turmoil of adolescence, she'd filled out (in every way) as an eighteen year old. She was tall and slim with long brown hair, big brown eyes and beautiful breasts -- not huge, but perky and eye-catching on her thin frame. By the time I was eighteen, she'd become even more alluring, her 21-year old body tight and tan with bulges in all the right places. She looked like a movie star and knew it, which is how this whole thing got started...
Jenny was finishing college, where she'd studied English and drama. She was keen to cash in on her acting skills and her knockout body, but was having a hard time lining up any start. She'd been talking with our parents about moving out of our midwest town.
"There are no opportunities in these backwoods. Here I am, 21 and still living at home!" Jenny complained one morning at breakfast. "I need to get to California to get into acting."
"And join about a million other wanna-be actresses waiting tables?" My dad commented. "What makes you think you'd be able to walk right into an acting position?"
"I know," Jenny said sadly. "If only I had some way to get right to the casting folks."
I'd been day-dreaming, furtively casting glances at her barely concealed breasts: Jenny always slept in a semi-transparent teddy and had been sufficiently depressed by her job prospects that she hadn't bothered to get dressed yet. On the pre-text of dropping a spoon I ducked under the table and was rewarded with a shot of her tight thighs and the edge of a scarlet thong barely covering the curve of her ass. I must have been down there a little too long, since she started squirming and when I sat back up she glared at me for a moment. By this stage I'd perfected the innocent disinterested look, so I got away with it.
My thoughts drifted to wondering whether I'd be able to get hold of that thong when she was in the shower later in the morning -- one of my favorite hobbies was to get hold of her panties as soon as possible after she shed them, while they were still warm. One memorable (but highly risky) day, I'd stood right by the curtain where Jenny was taking her shower, jacking off into a lacy fragrant pair she'd taken off moments before. I blew my load seconds before she turned the water off and I had to open the door silently and make a hasty exit, cum still dripping from my cock.
But as we cleared up from breakfast, I was left wondering about Jenny's comments about California. I had been taking a film and media class at college and that gave me this idea of a plan...
"Jenny", I said that afternoon, while our parents were out shopping. "You know you were mentioning Hollywood and all that this morning?"
"Yeah," she replied sulkily, figuring I was going to make fun of her. "So what."
"Well, there was a guy who graduated from our media program last year and is now working for a small studio out there. I wondered if you'd want me to put you in touch with him?"
Jenny did a double take. "You bet I would! What's his name, how can I contact him?" She was quite excited, bouncing in the chair (which made for a glorious sight when I furtively glanced at her bra-free T-shirt).
"Mike's kinda hard to get hold of normally, he doesn't give out his phone number, but I've emailed and skyped him a couple of times about a project I was working on -- next time I contact him should I mention I know someone interested in acting?"
I knew her answer but didn't guess at her reaction. Though we got on OK, I'd always been her annoying little brother, and we weren't a very physically affectionate family. Now though, she leaped up, came round the table, smothering me with a tight hug that brought her firm tits just below my chin. My pecker responded right away, and the surprise of this embrace left me unprepared. I think Jenny sensed the stirring in my pants because she abruptly let go and blushed a little, saying that she'd really appreciate me contacting Mike and to let her know what happens.
Mike in actual fact lived on the other side of town and was in my class at college. He looked older than he was, and with a pair of sunglasses could easily pass for a guy in his twenties. I'd mentioned Jenny to him a few times and even showed a picture of her (in her swimsuit) from our last family holiday. I knew he'd be game for this deception, but we had to play this carefully.
"Any word from Mike?" Jenny asked after dinner.
"Pretty early for him to respond I think -- he gets pretty busy."
"Oh, sure, I suppose," said Jenny looking sad. I didn't want her to lose interest in the plan though. So I thought quickly.
"I wonder if I should email some pictures of you to him?" I said reflectively. Jenny tensed up a little, smelling a rat. "I mean maybe some head shots so he gets an idea of how pretty...I mean just how you look." I ended up lamely.
Flattery worked, and Jenny agreed to let me take a few photos and email them to Mike. While our parents were making dinner, Jenny and I slipped into her room. I'd only been in there a few times (with her permission anyway) and I was excited that things were moving so nicely.
"OK, so let's make this good," said Jenny. I set up the lighting as best I could and brought up three of my best cameras, one set up on a tripod to make it look more professional.
"So, maybe some face shots straight on and some sideways." We took about 10 of each, and I sensed Jenny relaxing as she enjoyed posing for the camera. She really was amazingly pretty!
"Excellent. That should do it...unless you think you should have some full figure shots too?" I said, as I was toying with the tripod -- not quite taking it down, but trying to make it seem that this was no big deal to me.
"Er, well, sure I guess that would be good too." Jenny said uncertainly.
"Do you want me to take shots of you in those clothes?" I asked innocently.
Jenny looked down at the jeans and t-shirt she wore and bit her lip, thinking. She suddenly got a steely look in her eyes -- "I think these will be just fine, thanks." She must have guessed I was trying to coax her into showing some skin, but I didn't push it.
"Fine," I said, all but yawning. "These aren't MY first publicity photos."
I knew I'd hit the mark. "Well, take a few like this, and then I'll put on a dress."
I quickly snapped a few shots of Jenny in her outfit. She shooed me out of her bedroom to change. What she hadn't noticed was the small digital camera I'd set up on her dresser at the beginning of the session. As I'd see later when I retrieved the camera, I'd caught a fine video of Jenny stripping down to her underwear (black bra, another red thong) and trying out various dresses. Eventually she came to the door wearing a sexy black outfit.
"Wow," I said, "That looks awesome". Jenny looked at me for sarcasm, then realized I was serious. She smiled as she spun around.
"Yeah, I wore it when Tony took me to a dance last year."
Tony was Jenny's ex boyfriend. The loser had been caught dipping his cookies in someone else's milk and Jenny was better off without him, to my mind. She was still a little sad about the breakup though. I figured she was also sad about the lack of sex, since I knew for a fact that Tony boned her on a very regular basis. How did I know? My bedroom was right next door, and neither Tony or Jenny were very good at keeping their orgasms silent. One time I was determined to see more of Jenny during their love making and hid in her closet when they were making out downstairs after a party. They were both a little drunk and were oblivious of anything but each other when they finally staggered to the bedroom. Still, I was pretty nervous about being caught so I kept the closet door open to just a crack. That was enough to see a glorious sight! Jenny soon lost her clothing and lay on the bed on all fours, looking back at Tony (and, without knowing it at me) with a huge inviting smile on her face. Tony was struggling to get out of his belted pants, giving me time to see her unshaved pussy gloriously on display, as she swayed her hips seductively.
"I need you in me," Jenny said, and I nearly blew my load right then, since it seemed she was talking right to me!
Eventually Tony joined her on the bed and they hammered away while I whacked off in time with Tony's thrusts. Among Tony's other faults, he was pretty lame in the sack and shot his load into Jenny's writhing pussy after only about 2 minutes. I wasn't even half-way done and had to stop jerking off while they settled down to sleep, since I didn't want them to hear me. After I was sure their deep breathing was regular, I crept out of the closet and was rewarded by spotting Jenny's panties right there on the floor. Not wanting to pass up an opportunity, I wrapped her panties around my re-stiffening dick and jacked off crouching on the floor at the foot of her bed, enjoying the fresh smell of sex that perfumed the room. Tony rolled over on the bed, dragging the sheets a little away from Jenny's sleeping body. I had to take a look and was rewarded with a sight of one firm breast, nipples stiff from the air conditioning and a perfect shot of her pussy. As I watched, still pounding my meat, an impressive stream of sperm leaked out of her tight pussy (I guess Tony had some qualities as a lover after all). That was it for me and I couldn't have stopped if I'd wanted to. I shot string after string of cum right where I stood, only half aware that most of it was landing on my sisters legs, tummy and the bush of her pussy. As I realized she wasn't going to wake up, I moved up besides her so the last two spurts landed on her exposed breast, sliding down her tits obscenely with each breath she took. I wondered about trying to mop up my cum, but figured a little extra sperm would hardly be noticed even if she did wake up.
All of this came back to me, since Jenny wore the same black dress on that night. I tried mightily to control my stiffening rod and get back to business.
I took about 20 more photos, asking her to pose in various fairly tame ways.
"How about holding your hands up in the air, like you're celebrating something?" I suggested. Jenny hesitated -- that would bring her breasts squeezing forward in the tight material (something I well knew), but she liked the idea and really got into it as we took shots, winking at the camera, bending her knees and even bending over one time, Marilyn Monroe style, which gave a great shot of her cleavage. I stayed cool throughout this (though I can't say the same for my cock, which meant I had to keep moving behind the tripod for some coverage).
"OK, that's a wrap," I said. Jenny looked a little disappointed, which was exactly what I wanted. "I'll send this to Mike and see what he says."
I waited two days to move to the next stage of the plan.
"Hey, um Jenny," I said casually one day we were lagging behind our folks in the park. "Mike sent me an email back this morning."
"What'd he say!" She exclaimed.
"He'd like to set up a skype call over the next couple of weeks. Wants to know our availability."
""Our availability? Will you still be involved in this?" Jenny asked suspiciously.