Betting On My FamilyChapter 5: Ben's Big Day free porn video

I stayed quiet for most of the ride home. I had plenty of questions to ask but I wasn't sure if I should be too candid with Riley. She was obviously loyal to Dana, and after effectively being conscripted into prostitution and having my life and family threatened, I was a little pissed off at Dana. I wasn't sure how friendly I felt toward Riley. Sure, I had fucked her mouth, twice, but a conversation required a level of intimacy that I was unwilling to grant. I saved my questions for a time when I could ask them to someone I trusted.

Most of the way home, I felt terrible. My penis was still buzzing from all the attention, but mentally, I was a bit of a wreck. I felt very conflicted about what had happened to me. A blowjob might have meant nothing to Riley, and it certainly meant nothing to Dana, but it was my first, and so it meant quite a lot to me. I couldn't deny that it felt amazing as it was happening, but as soon as we were back in the car, I was hit by a massive wave of guilt, and then shame. I didn't know where the emotions were coming from, but I knew this wasn't a healthy way to be introduced to sex.

I couldn't identify what value I was judging myself against - purity? normalcy? - but I knew that my father would be disappointed in me if he knew, and that hurt. I had done nothing wrong, and yet felt like I'd let everyone down. Should I have refused Riley? Said "No thanks?" Stoically pushed her away from my dick? I couldn't imagine what I should have done. I only knew that I should have done it.

I knew that my old friends would have been thrilled, had this happened to them. Why did I feel this way? I was staring out the window, puzzling through this ethical quandary, when we arrived back at the Wawa. I was so absorbed in thought that it took me a second to realize that we had arrived. Riley stopped the car.

"I'm getting the feeling that you're a little messed up about what went down tonight," she said. I didn't answer. I just looked at her and unbuckled my seat belt. I reached for the door but she grabbed my wrist at the last second. "Ben, you're just overthinking this. I get that tonight was weird but I promise you'll feel a lot better about it tomorrow." I wanted to trust her, but I didn't.

"Let go of me," I said. She didn't.

"Ben, you've done nothing wrong." I pulled my arm free of her grip and jumped down from the vehicle, slamming the door and walking quickly away. I wasn't angry at her. I just didn't want her to see how choked up her remark made me. What was wrong with me? I'd gotten everything I had wanted only a day ago, but I didn't feel happy. I felt confused and I felt afraid.

To make matters worse, my dad and Babs were making out on the couch when I got home. It didn't bother me too much, but catching one's parents in the act tends to rattle the nerves. Some movie was on the TV and Babs was lying on top of my dad, using him as a kissable pillow. She quickly composed herself at the sound of the door but I was already walking toward the stairs. I felt shitty and didn't want to be cheered up.

"Hey buddy." My father, as ever, was nonchalant. "Have fun at your friend's?"

"I had fun," I answered. Babs slid down his frame to rest her head on his chest and he idly stroked her hair. I reached the stairs.

"Hey Ben?" he called. "I forgot to mention it earlier but I was able to get the afternoon off tomorrow for that movie you two wanted to see." The movie he referred to was the oh-so-quotable "The Princess Bride," a movie that Katie and I had loved since babyhood. It was a tradition of ours to watch it every year on our birthday, but a local movie theatre was playing a bunch of old classic 80's and 90's films for a single day only, trying to stir up profits. "I know I've been working a lot lately with the move So I asked the guys to cover for me. Thought we could check out bikes afterwards." I had been asking for one for months.

"Awesome," I thought, then "ahh ... shit."

"That sounds great dad, but I can't." He paused whatever they were watching and craned his head around to look at me.

"You can't?" he said. "You asked me to take the day off weeks ago."

"I know ... I'm sorry. But some people are on vacation and I really can't let Derek do all of the houses himself." Plus, if I didn't show up at the neighbor's' house tomorrow to let a strange woman fuck me, then you'll be ruined and I'll be killed.

He nodded. "Well alright," he said. He looked upset, but I knew my dad would forgive me as long as it was work-related. "You can't let your coworkers down. Some other time, then." I started up the stairs again, then thought of something.

"Take Katie though," I said. "She's been really bored lately and it'd do her good to get out of the house." My dad smiled at me and Babs did too, looking in my direction. "What?"

"Nothing," he said. "It just makes me happy to see what a decent young man you've become." My throat caught. It was the kind of thing my dad was always telling me but I didn't deserve it. I hated lying to him. He had sat me down when our mom left and told me everything would always be alright as long as we were honest with each other. He promised me that he'd never lie to me and I'd promised him the same. "I want you to know that I'm really proud of the way you've been handling this job." I turned away from him.

"Thanks, dad."

I wanted nothing more after that than to lay my head down and go to sleep. It had been a long day and tomorrow was shaping up to be a doozy. I was actually relieved when I opened the door to the attic and found the lights turned off. Figuring Katie was asleep, I crept up the stairs quietly. Just as I reached the top though, I heard a curious noise from Katie's side of the room that made me pause. It was a small whimper and initially, I thought "Great. She's crying again." But then I heard it again, more clearly, and I realized that it was no such thing.

The stairs opened onto my half of the room, so I quietly got down on my hands and knees in the near total darkness and crawled over to our makeshift sheet partition. There was a very small slit between two sheets that I could peek through, and even after everything that had happened that day, what I saw through that slit near stopped my heart.

Katie was masturbating, which was surprising enough, but that wasn't what was most surprising. She was lying on top of her comforter, legs bent and spread, and she was frigging herself with her right hand while her left held her iPad, which bathed the rest of her nakedness in a soft blue light. I was instantly inflamed at seeing her naked for the first time, seeing her completely bald pussy and puffy lips, and her small firm breasts with pointy excited nipples. What was even more erotic to me was the way her body moved. As she rubbed herself, she squirmed and writhed atop her comforter, her athletic abs clenching and releasing, her bare thighs and hips thrusting against her hand. It was, shamefully, incredibly hot to me, but that wasn't what was most surprising.

The really surprising part was what she was masturbating to. On her iPad was a single picture, blown up to full screen. It was of a tanned topless boy wearing trunks at the beach. I knew the picture well because I'd uploaded it to my facebook profile the previous summer. It was me. My sister was masturbating to a picture of me. God help me, but for some fucked up reason, it was the sexiest thing I'd ever witnessed.

Sure, I'd seen Derek pounding a woman senseless earlier, and Riley blowing me had also been a pretty stimulating sight. But seeing my sister there, my twin sister, frantically rubbing her pussy lips to a picture of me fucked with my head. It was just so wrong, so improper, so unbelievably, inconceivably HOT! She was moaning very softly in that cute, surprised, innocent voice all girls seem to know, and she arched her back off the bed as her eyes closed and her head rolled back. "Yes, yes," she whispered, approaching release. "Ohh Ben!"

Hearing Katie moan my name was too much for my fifteen-year-old brain to handle. I clenched my teeth to stop myself from crying out too, and then summarily came all over the insides of my jeans. Katie's little peep show had taken me from flaccid to cumming in about a minute flat. To this day, it remains the shortest and most unexpected sexual experience of my life.

Even having made a mess of myself, I couldn't tear my eyes away. I knew it was wrong - so terribly wrong - to sexualize my sister, but she was everything I found attractive. I can admit that now. I loved that she was so petite, probably 90 lbs. soaking wet. I loved her cute little bangs that reminded me of Carly Rae Jepsen. I loved her braces, as it was one of my fetishes. I loved her tight muscular waist and "outy" belly-button. And I especially loved her perky little tits and muscular runner's ass. I could stare at that ass for days.

Katie was panting, her abs undulating, creating a sexy rippling effect up her entire front. Her hand was a blur between her legs and she let the iPad drop to the mattress forgotten. Her moans became a little bit louder and then her back arched so sharply that she almost bent completely over backwards. She came shaking and whispering my name, and it took all the self control I had left to not burst through the curtain and do unspeakable things to her. After only a few seconds, her tensed body became pliant once more, and as she relaxed into her nest of pillows, I tore my eyes away and crept back to the stairs. I gave her a moment to compose herself and then tiptoed downstairs to the door, which I then opened and closed loudly enough for her to hear. I then walked up the stairs and collapsed on my bed, emotionally ravaged anew by what I had seen. I held my head in my hands and groaned.

"Ben?" Katie said from behind the sheets.

"Yeah, it's me."

"Great," she said. "Mind keeping it down? Some of us are trying to sleep."

"Sorry Katie," I said softly, exhaling heavily and smiling. As I kicked off my shoes, I added "Whatever you want," and meant it. I loved my sister. I never before had seen her in the particular light that I did that night, but she was my twin, and I would do whatever I had to to keep her happy, and felt obliged to get her everything that she needed or wanted, even if it turned out to be me.

I was happy and quite flattered that Katie found me attractive, but frankly, the revelations of the previous night could not have come at a worse time. I was already nervous about having to fuck Triss later, and knowing that my own sister and best friend wanted a piece of me as well dumped another bucketfull of anxiety on my lap. I had avoided her all morning because the moment I saw her strolling through the partition, pajama-clad and yawning, I grew a massive chubby that could not be abated.

Breakfast was awkward and mostly silent as we read our respective sections of the paper, but I couldn't focus on the funnies because I was too focused on Katie, leering at her out of the corner of my eye, unbuttoning her pajama top in my mind. I needed to get the hell out of there and so left for work early.

Derek was waiting for me when I got there, and from his body language, I knew he was pissed. He crossed his arms as I drew closer to the van and approached me.

"I go out of my way to be nice to you and you fucking go over my head like this? Are you for real?" His confrontational posture surprised me and I held up my hands in peace.

"I don't know what you mean, man." I took a cautionary step back.

"No?" he said. "So you don't know what you're supposed to do today? You don't know why Dana called me last night and threatened to cut me out if I didn't go along with it?"

"She threatened to kill me, man." Derek paused.

"What?"

"Yeah," I said. "I don't know what she said to you but this wasn't my fucking call. It was not my idea." At that moment, Drew hopped out of the back of the van holding a foil-wrapped half-eaten burrito and wearing ear buds. He walked over to us and removed his headphones, taking a big bite and smiling pleasantly.

"Dana threatened to kill you?" Derek asked. Drew started to choke and I nodded.

"Only after disgracing my family, destroying my rep, and getting me kicked out of school." Derek kept his eyes on me but walked behind Drew and punched him on the back. He kept choking. "There was a whole speech," I said. "That woman is terrifying." Derek wrapped his arms around Drew's waist and began to apply the Heimlich maneuver. After several heaves, Drew spit out a hunk of meat and fell to his knees, gasping.

"Was this the "Do not cross me" speech?"

I furrowed my brow. "That was mentioned, yes..."

"Be straight with me, Ben. You didn't ask for this?"

"No!" I said desperately. "I mean ... I may have wanted it a little bit, but Dana called me." Drew stood back up, coughed, and took another bite of his burrito. I held up my right hand "I swear, man. Riley came and picked me up and then took me to a storage yard, and then she blew me while..."

"What?"

Drew started choking again and Derek once more assumed the position. "Damn it, Drew. Stop eating!"

I told them the rest, about the weird interview, and the weird questions, and the tube of cream that she'd given me. I learned that most of it was routine. Dana had videos of Derek and Drew answering the same kind of damning questions. But their ears perked up at the mention of Riley. Apparently blowjobs from the personal assistant hadn't been a part of their initiation, but they were older and non-virgins so Dana probably assumed they knew what they were doing. In a weird way, it made me feel better knowing that I was the only one that got head, like that blowjob might have actually meant something. Maybe Riley wasn't as cold as I imagined.

The other part that surprised them was the $1000 up front that I had received, and later hid in my socks drawer. It was much higher than their standard rate of $100 a session and Drew would have started choking again at the mention of a grand had Derek not taken the burrito away from him. "You can have it back when Ben's done speaking." When I told him that the exorbitant amount was because I was a virgin, Derek frowned.

"That sucks, dude. I'm sorry." I didn't understand what he was sorry for. When I asked about it, he merely shrugged. "I don't know," he said. I just kinda feel like your first time ought to be with someone special, you know?" At least on that point, I thought he was crazy. What could be more special than fucking a pornstar?

We loaded up the van and headed to our first house. Derek had an appointment inside with "Mrs. Donaldson" so he left to go bang her socks off while Drew told me more about Dana and "The Business." He, for one, was glad that I finally knew about it because he had been sick of skirting the issue for two weeks. Keeping it a secret was driving him mad.

"Yes, the scorched Earth speech is familiar to both of us," he said. "But to my knowledge she's never threatened to kill anyone before. Maybe she likes you," he suggested.

"She likes the money I can make her." I said.

Drew nodded, smiling. "That does seem more likely."

I felt oddly better that Dana threatened everyone who worked for her, but Drew warned me not to test her. "I've never heard of her actually going through with her threats, but rumors abound. I wouldn't risk it if I were you." I wasn't afraid anymore of getting whacked but that didn't mean I wasn't still stuck in this job for the moment. Drew was right. It wasn't worth the risk.

When the magic hour finally arrived, I was more excited than anything else. I was prepared to forfeit my V-Card, and I was going to do it with a smile on my face, goddamn it. I walked through the side-yard gate with my chest puffed up and my head held high, and then, I promptly began to panic.

I had been nervous all morning, but when I say panic, I mean that I effectively lost my mind. The last two weeks had been so strange and so surreal that my situation hadn't really registered with me yet. I was aware of everything happening around me, but I felt more like a witness to events rather than an active participant. As I walked through Triss's gate though, something triggered in my mind. I became lucid and calm and was able to appreciate the gravitas of my circumstances.

I realized that if I went through with this, then Triss was right: I'd be a prostitute, a sex-worker. Was I OK with that? I wasn't sure how I felt, but I was positive that my father would feel angry and upset that I'd agreed to do such a thing. But did I agree? Looking back, Dana never really gave me a choice in the matter. She just paralyzed me with Riley's tongue and gave me orders.

Additionally, what I was about to do was VERY illegal. Could I go to juvie for this? And what would Katie say? Would she stop speaking to me? I didn't care much about what my step-family thought, but I loved Katie. I couldn't bear losing her friendship. And about Katie, why THE FUCK was she masturbating to my picture last night?

I stopped dead in my tracks and Drew ran into me from behind, muttering a curse. I spun around, wild-eyed. "I can't do this, man," I said. "I'm freaking out!" Drew chuckled before realizing that I wasn't joking. He put a hand on my shoulder.

"Calm down, Ben. You're gonna give yourself a stroke."

"I can't calm down. Are you hearing me? I can't do this!"

"Dude, please do this. You need to release some tension. All your anxious bullshit is fucking up my chi."

"This isn't a joke!" I snapped. "I could go to prison."

"No you couldn't. You're fifteen."

"Well I could go to juvenile hall!"

"You're really overreacting, dude."

"Don't you get it? I! Can't! Do! This! Derek walked through the gate behind us and approached me. He set down the bucket he carried, and then slapped me across the face. He hit me pretty hard, causing me to stumble.

"Get your shit together," he said. "I think this is a horrible idea but it's done. It's happening." I rubbed my face and stood back up. I'd gotten into fights in the past over far less, but I wasn't angry. I actually felt a little better. "Now quit whining like a little bitch and go become a man." He grabbed my shoulders and physically turned me back around before pushing me down the pathway. I walked forward tentatively, but at least I was moving forward again.

We finally made it to the backyard and dropped the equipment. Off came the shirts, and Drew started remarking about the landscaping and yard-work. It was truly unique, like having a botanical gardens for a backyard. I took a deep breath. It was time. Derek nodded at me.

"Get it done," he said. I walked toward the house, but before I got there, Triss pulled open the glass sliding door and emerged, clad in a cream terrycloth robe and a wide giddy smile that made her look like a kid on Christmas. Derek rolled his eyes.

"You're supposed to stay inside until..." Triss fixed him with an icy stare. "Ahh, fuck it. I'll just clean the pool. Do whatever you want." Her smile quickly returned and she took my hand.

"Come with me, Ben," she said, and then led me to the house. I took one last look at my comrades before going in to face the music, and Drew mouthed the words "you lucky bastard" as Derek shook his head. I wasn't sure which one had the right view of things, but it didn't matter anymore. Triss giggled as she pulled me through the door. It was time to take care of business.

Triss thought so too. I wasn't a second through the door before she shoved me against the wall, her hands pressing, palpating, rubbing up and down my chest and stomach. She kissed me fiercely, mashing her lips to mine, forcing my lips apart with her tongue.

"Mmm, you smell like Bubblicious," she moaned. She released my lips and visually inspected me, forming claws with her fingers and dragging her nails across my ribs. I was hard almost instantly.

"Hi Triss."

"Hi," she exhaled, while leaning her body against mine. I went rigid in more ways than one as I felt a small hand cupping my large bulge. "This is gonna be fun," she whispered. "I'm excited. Are you excited?"

"Oh, I'm very excited," I said. Her fingers sought out the outline of my cock and squeezed it, making me shiver.

She laughed at my reaction. "I can tell," she said, releasing me. She pushed off me, taking a step back. Her robe had loosened a smidgen, and displayed a lower neckline than before. I was tantalized. "C'mon," she said. "I have some surprises for you, it being a special day and all." She walked toward the kitchen. "What do you want to drink? Beer? Wine? Juice?"

"Nothing thanks, I'm not thirsty."

She took a jar of apple juice out of the fridge and poured me a glass. "Trust me," she said, handing it to me. "You will be." She jerked her head toward the hallway. "Follow me." She turned and sidled away and even through the thick robe, I could see the shapeliness of her tight little butt, and the sensual arch of her back. I followed.

There were two open doors in the hallway, and I glanced into the first as we passed to see Diana lounging on a pile of pillows atop a lavender king-size bed. I merely smiled and passed her by, drawn as I was by Triss's backside, but I heard her say "Ben, hold on a second," and Triss turned around, giving me a moment. Diana walked to the doorway. She was wearing pajama pants and a T-shirt again, and had cute little reading glasses perched upon her nose. She held a hardcover book the approximate size of a cinder block. She looked at Triss and then at me.

"Are you sure you want to do this?" she asked. I quickly nodded. Derek had slapped away most of my hesitation and the rest had been sucked out of my mouth by Triss. I was sure; nervous as hell, but sure. "you only lose your virginity once," she said. "Wouldn't you rather it be with someone you love?" She glowered at Triss. " ... or even someone your own age?"

"I don't know any girls my age," I said, looking at Triss, who was waiting patiently, twirling circles in the carpet with her toes. "Besides, you girls just..." Both of them looked into my soul, batting their eyelashes. " ... you guys know you're gorgeous..." They both grinned prettily.

"C'mon, Diana. He's so adorable. Let me corrupt him." Diana never looked away from me. Her eyes looked a little sad.

"You know what you're getting yourself into, right? This girl is a freak. Most grown men can't handle her." Triss reached for my hand and started pulling on my arm.

"Ben can handle me just fine, Diana, as long as he handles me hard and repeatedly." Well, I couldn't get any harder and I was prepared to do her as many times as humanly possible, so at least I had that covered.

"It's OK," I told her. "I want this." Triss's tugging on my arm opened her robe a little more and I could see the rounded peaks of her heavenly breasts. "I really really want this." Dana looked from Triss and then back to me.

"I don't know," she said finally. "I guess I better come along too. For safety's sake."

"Fine," Triss said, letting go of my hand. "I need you to hold the camera anyway."

"Camera?" I said, looking at Diana. I'd had quite my fill of cameras lately. Diana winked at me in return.

"You only lose your virginity once," she said.

Diana put the book on the ground and followed Triss and I to the other open door in the hallway. The bedroom was the same size as Diana's and also had a king-size bed, but the comforter and pillows were removed, leaving nothing but white satin sheets. On the mattress were a number of outfits. Triss stepped behind me and wrapped her arms around my waist, resting her head against my shoulder. "Choose what you'd like me to wear, lover boy," she said. I grinned like a kid on his first trip to Toys R Us. She frowned at Diana's pajamas. Pick something for Diana, too."

There were six outfits on the bed, each with matching lingerie and several with stockings. Having no experience with lingerie at all, I took my time examining each piece. Diana provided the nomenclature: teddy, chemise, baby-doll. I couldn't really tell the difference. I chose two old staples that I had seen before in films. For Triss, it was the naughty schoolgirl outfit. My previous school had a uniform and I'd never really gotten the chance to exercise the fantasies that those skirts had conjured for me. The getup included a green and grey plaid micro-skirt, thigh high white stockings with frills, and a tiny white blouse with a striped tie and jacket. The lingerie was a light pink, furthering the "innocence" theme and I found it amusing to picture Triss as anything but the crazed sex demon I knew her to be.

For Diana, I went a different direction. Because she struck me as a super hot nerd to begin with, I thought it would be fun to see her act authoritatively. I chose for her the sexy officer costume that consisted of aviator sunglasses, a tight-fitting blue patrolman shirt, and a skimpy pair of blue booty shorts. It was ridiculous, but I doubt the creators were going for realism. In addition to a utility belt with furry handcuffs, the outfit also came with a very intricate black set of expensive-looking lacy underwear, complete with fishnet stockings, garter belt, and partially transparent bra and panties. Choosing their outfits was a lot of fun and I was much more relaxed when done, as well as more aroused. The girls disappeared into the ensuite bathroom and left me sitting on the bed with a massive erection.

My anxiety slowly returned as the women readied themselves. I could hear them speaking to each other in hushed voices behind the doors but it was too soft to make out. I paced around the room, examining the top of dressers and night-tables. There was the usual collection of bedroom necessities, as well as two expensive-looking cameras. One was a standard digital camcorder and the other was a GoPro cam that could be worn like a headlamp. I had seen a few POV vids myself and found them very enticing. There was also a tripod set up in a corner and my glass of apple juice. I had become a bit thirsty, so I tipped it back and drained it. Juice rocks.

And then, the door opened...

Triss emerged and quickly shut the door behind her. My mouth dropped. She'd been wearing light makeup the first time I'd seen her, but I never saw her in full-on porno glory before. Her eyelashes were thick and curly, and her eyes were darkly-lined and smokey. Her eyebrows were defined and expressive, and her lips were covered in a wet glistening shade of pink. Her contact-enhanced irises seemed to glow a curious green, and her hair was done up in typical school girl fashion: pigtails.

"Oh my God," I said aloud, physically and mentally stunned. I'd thought pornstars were hot in film but up-close, they were paralyzingly attractive. Her outfit admittedly helped. Her teachers would have been very upset with her. Her white blouse was far too tight, her tie was loose and haphazard, and that skirt was definitely not regulation length. It was probably only twelve inches long, about as long as my dick currently felt.

Without saying a word, she walked to the nightstand and slowly bent over to pick up the camera, granting me an exquisite view of two tanned round buns in the process. She then placed the camera on the tripod and set it up to capture the bed. And then she fixed her face with a pouty expression, and started stepping toward me. "I know I haven't been doing well in your class, Mr. Fairchild," she said in a mock-schoolgirl voice, "But I just haven't been able to concentrate lately." She brought a finger to her lip in an odd and enticing gesture and hooked her other thumb under the top of her skirt, drawing attention to the G-string visible on her hips. "Is there any way I can raise my grade? Extra credit perhaps?"

"I'm sure we can work something out," I said, deciding it might be fun to play along. "But your grades have really suffered. It's going to take a lot of hard work."

"I see," she pouted. "I'm willing to do anything. How hard will it be?"

"Extremely hard," I said. The pun battle was on. I stepped forward so that I looked down upon her. "You're in pretty deep. It may take all afternoon to beat out a solution." She moaned almost imperceptibly and her eyes flashed.

"But I only have an hour," she said. "Can you manage to shove that big fat afternoon of work into my teeny tiny amount of time?"

"I think we can make it fit. But we must begin immediately if we plan on cramming everything in." This was getting ridiculous.

"It's going to be tight," she said. "Agonizingly tight." She reached out a finger and very gently scratched the bulge in my jeans. "What do you need me to do?"

"First things first," I replied. You're wearing too much clothing for hard work. We need you out of that uniform immediately." As amazing as that outfit looked on her, I thought it would look better on the floor.

"All of it?" she asked, dutifully shrugging out of the blazer. I noticed the crest on the lapel for the first time. It was a picture of a checkerboard shield depicting alternating boobs and penises with the name "Fuck U" overtop. Classy. She dropped the jacket to the floor and yanked the tie off in swift order, but feigned difficulty with her blouse. "I can't seem to work these buttons, professor. Can you help me?" I smiled deliriously and closed the final distance between us.