Chapter 16: Casual Sex

JUNE 2001, JUNIOR YEAR

"Unnnnnh! Ohhhhhh! Unnnnnh!" The hot brunette before me had been whining and whimpering constantly for the past fifteen minutes.

I held myself balls deep inside the tight, clenching pussy. With my hands gripping her slender hips, I ground my pelvic bone against her asscheeks and pivoted my cock inside her, stretching out her vaginal walls.

Her head hung down between her shoulder blades in this doggy-style position, her silky brown hair cascading down to the mattress and revealing the creamy skin of her neck. And since I wasn't presently pounding her body and throwing her off-balance, she was able to support herself on just her right arm while her left hand rubbed insistently at her own clit.

And from the combination of my thick cock rubbing her insides and her own manual manipulations, Stacey Whitehouse, wealthy and beautiful Senior babe, started her orgasm.

Her back bowed into a reversed arch, her belly heading towards the bed while her shoulders went rigid, and she thrust her ass up against me. She tossed her head back, sending that mane of dark hair flying into the air, and her scream was loud enough that the maids would have no doubt what was occurring inside their employer's daughter's bedroom.

I kept rotating my dick while she spasmed. And towards the tail end of her climax, I re-started pumping my shaft in and out of her. Stacey's hips bucked and heaved against me as her orgasm played out, and then she let her arms collapse as she dropped down to the bed, only her ass held upright by my cock currently skewering her cunt.

She managed to balance on her knees long enough for me to thrust my way up to the edge of my own climax, and as I felt the pressure building, I grunted out my warning. "I'm gonna cum, Stacey."

It was part of the routine. She was protected, but her parents had drilled into her the dangers of getting knocked up when she had such a high net worth, and so she never let a boy cum inside her pussy, period. If he did, that would be the last time he ever touched her. I didn't mind. There were plenty of other places to leave my deposits.

Stacey thrust against me twice more, not yet willing to give up the full sensations, but then she leaned away from me until my dick popped free and she flopped around onto her back. I hurriedly scooted forward on my knees until I was straddling her chest; and she quickly seized my cock in her left hand and began stroking me in earnest.

"Cum on me, Ben," Stacey urged in that alluring accent. "Cum all over my naked body." I LOVED the way she pronounced 'body' like 'bohd-dee'.

As the pleasure overwhelmed me, I looked down to see the pretty brunette with perfect makeup and grooming tilt her head back and open her mouth gaping wide. It was such an inviting target, and with a low grunt I let my first wad fly.

Her aim was slightly off from her jacking motions, and the first string of cum lanced across her nose and down across her upper lip. But the second shot went straight in, and the third. And then smiling broadly as she swallowed, Stacey let her head fall back against the mattress and she continued jerking me, letting the rest of my jism dribble out and splatter over her neck and tits while she bathed herself in my cream shower.

Five minutes and a couple of washcloths later, I was fully dressed and Stacey wrapped herself in a silky, sheer robe. She escorted me to the front doors of her personal suite, and when she opened them, a maid was already waiting in the hallway.

"Ma'am," the maid bowed to Stacey and then handed me a Gatorade. The maid had come prepared after the last few visits.

Then the maid turned to me. "Will there be anything else, sir?"

Stacey chuckled. "No, I think he got everything he came for."

I smiled in agreement.

Stacey sighed and leaned against the doorjamb. "When can you visit again?"

I thought over my schedule and Stacey's typical intervals. She usually wanted to get fucked every four or five days or so. It was a Saturday so I suggested, "How about Thursday?"

Stacey smiled and then leaned in to peck me on the lips. "See you then!"

The maid then escorted me out. Just another routine afternoon.

Brooke met me by the door when I came in. She took one look at me and then obviously sniffed the air. She was wearing just a thin cotton top and I swore I could see some dents forming above the mounds of her growing breasts. And then my little sister gave me a Cheshire grin. "You're certainly spending a lot of time out and about lately. You sure you're not dating anyone?"

I shrugged. "None of your business."

Brooke stepped forward and put her hands on my chest, leaning in and taking another long sniff. She closed her eyes and got a look of utter arousal on her face, and I had to admit, my little sister looked damn sexy at that moment. But then she stood up straight again and opened her eyes. "Fuck, now I'm going to have to go upstairs and masturbate."

With that, my sister turned around and headed up the stairs ahead of me. I fought the impulse to stare at her jeans-clad ass on the way up, sighing in defeat when I failed.

"Dude, where were you on Friday?" Kenny asked as he sat down next to me at lunch on Monday morning.

"What?"

"I called you. Your sister said you were out."

I thought back ... Friday ... oh, yeah. Stacey had set me up with her friend, Mandy Lin, who went to a private school and whose dad owned some Taiwanese Electronics company. I shrugged, "I was out."

Kenny arched his eyebrow at me. "You on a date or something?"

I shook my head. It wasn't much of a date; we never left Mandy's house. Stacey knew exactly what I was good for and Mandy had gone through a big dry spell. The tall, beautiful, older teen just needed to get laid without any of her friends or others in her social circle knowing about it. I'd pretty much been recruited to be an unpaid gigolo, which was fine by me. Mandy had a tight pussy and was an excellent cocksucker.

Romance wasn't on the agenda; but discretion was. I may not have been capable of being loyal to a girlfriend, but I certainly could keep my mouth shut and not blab about my conquests. Hell, I was pretty sure no one knew I'd been schtupping Stacey for the past few weeks, not even my best friends.

"Told you, Kenny. I'm not talking about it." I focused in on my food and then joined in on the table's conversation. By now, the rest of my old crew was assimilating me back into their good graces. Abigail and Allison Sanders were sitting right across from me, flirting innocently along with their giggling and chatterbox comments. Recent couple Stephanie Vo and Sung Joon was on my right. And even Elaine Fukuhara was starting to talk to me again.

Megan and Cassidy, while they didn't sit next to me or anything, at least would talk with me. We'd seemed to settle into a non-hostile exes-type of relationship, although Cassidy still gave me puppy-dog eyes of longing every once in a while and Megan would occasionally stare into my eyes as if searching inside for someone she recognized.

Even Adrienne didn't seem overly angry with me. If we passed each other in the hallway, she would merely nod in greeting and then continue on her way. She would get a look in her eye similar to Cassidy's on occasion, but for the most part she was handling things pretty well. If she was hurting inside, Adrienne was doing a very good job covering it up with her usual perky-friendly-flirty demeanor.

And taking their cue from Adrienne, the rest of the cheerleaders and jocks similarly accepted me. Break-ups and cheating and drama were a way of life for them, and they rebounded much more quickly. Summer MacIntosh and I shared second period and our third period classes were next door to each other, so we'd actually walk between classes together and chat about whatever. And whenever Trevor Hansen or Jae Choi would pass me in the hall they'd offer their verbal "What up?" Even though I no longer took lunches with them, we all remained acquaintances or even casual friends.

And then there was Donna. After lunch she literally bumped herself into me and then smiling, asked, "We on for this afternoon?"

"Sure," I replied breezily.

"Hope you've stocked up on fluids. 'Cuz I'm feelin' extra frisky today," the curly blonde babe giggled.

I LOVED Mondays.

On Thursday, while walking from second to third period with Summer, we passed Stacey going in the opposite direction. The willowy brunette flashed me a knowing smile, her soft brown eyes twinkling, and then continued on her way. I grinned, knowing that I was scheduled to visit her for our usual romp around the mansion.

"Did Stacey Whitehouse just wink at you?" Summer asked with an amused expression on her face.

I looked at Summer with surprise and shrugged. "I dunno. Ever since I broke up with Adrienne there're a lot of girls throwing winks my way."

Summer chuckled. "You're turning into a regular Playboy, Ben. With no girlfriend now, I wouldn't be surprised if you were banging a bunch of different girls around the school."

I smiled and shook my head in the negative. "Wouldn't that be nice? Right now I'm just trying to finish out the school year in peace. My grades this quarter are going to be REALLY important for college apps. Speaking of which, do you want to study together for the Modern Lit final?" I asked, referring to our second period class together. Finals week was next week.

Summer nodded, sticking out her jaw thoughtfully. She brushed her fine blonde hair behind an ear and twinkled her blue eyes at me. "Sure. Gimme a call. Saturday, maybe?"

I grinned. "I'll see if I can fit it into my busy calendar," I joked while miming a fucking motion with my hands.

Summer laughed in amusement and turned towards her classroom. If only she knew I was serious.

After lunch, when the meal was finished but well before the bells rang, the Sanders twins were packing up their lunches and Abigail leaned forward, grabbing my attention. "Hey Ben?"

"Yep?"

Abigail looked at me intently while Allison's expression mirrored her sister's, who was older by two minutes. Abigail nodded her head off towards a more private space. "Can we ... talk to you?"

"Sure." I stood up and so did the twins. Kenny gave me a weird look and I shrugged, not knowing what it was all about either.

Coincidentally, we ended up the same alcove where Cassidy told me she didn't want to get back together with me, and I leaned back against the concrete wall while facing the two cute, slightly underdeveloped 16-year-olds. Abigail and Allison were identical twins who usually wore identical outfits, today being baby T-shirts and jeans. Their dark brown hair was pulled into pigtails and they wore just a small amount of makeup. They stood 5'3" and looked very young from the way they both stared at the floor nervously. Heck, Brooke looked older than they did right now.

I glanced back and forth between the two of them, waiting for one of the girls to speak up. After all, THEY had been the ones to ask for this little conference. But Abigail just looked nervous and scared and Allison finally had to prod her slightly- older sister with a finger to the ribs.

"Hey!" Abigail protested and then looked back at me. "Well, Ben. Uh, we were kind of wondering ... and I mean ... we already asked Megan and Cassidy if it was okay ... but we were kind of hoping ... I mean, uh, are you busy on Friday?"

I blinked twice. "Friday? As in ... tomorrow?"

Abigail's face fell, absolutely certain that I had already made plans.

"Wait, no, no, I'm not really busy." I waved her off. I didn't have anything set. True, I'd tentatively figured I'd give Donna a call and then I'd give her a few injections of sperm, but those weren't firm plans. I arched an eyebrow and looked more intently at Abigail. "Are you asking me out on a date?"

Abigail glanced at Allison for a moment before turning back to me. "Well, uh, yeah, Ben. Actually, we both are."

I blinked twice. The girls had dated sporadically. I wasn't privy to the details, but while they'd double-dated together, I'd never heard of them going on a date together with just one guy. "Both of you?"

Allison finally piped up. "C'mon, Ben. It's not like you haven't been on a date with two girls before."

"And we DID talk to Megan and Cassidy about this first," Abigail reiterated. "We wanted to make sure they would be okay with us asking you out."

"So ... uh..." Allison began nervously. "Will you go out with us?"

My eyebrows furrowed. The LAST thing I needed was two more girls in love with me. And both girls paled at my hesitation. Gently, I said, "Girls, we're friends..."

Now they looked like they were going to start hyperventilating. So I decided to slightly change my approach. "I'd be happy to go out with you," I said quickly.

Their panic seemed to lessen but there were still nervous expressions on their faces. We all sensed the "but" coming. So I started, "But, I don't want to lead you on. I'm not looking for any serious relationships right now. I'm not ready to jump into anything like that just yet."

Relieved, Abigail sighed, "Oh, don't worry about that. We're not looking for anything serious, either, Ben. We just want to go out on a date and relax before Finals. We know you. We like you. Going out with you won't be as awkward as trying to go on a date with some other guy."

"Yeah, we're friends. We just want to go out together and have some fun!" Allison chimed in, feeling encouraged.

I shrugged. Why not? "Okay, what do you guys want to do? Just dinner and a movie? Or-"

Abigail cut me off with a mysterious smile. "Just come pick us up at 6pm. We'll make all the plans."

I glanced at Allison, who nodded in agreement. "We'll take care of everything."

So taking a deep breath, I nodded and smiled. "It's a date."

Stacey had a little surprise for me that Thursday afternoon. I walked into the bedroom to find both her and Mandy Lin waiting for me, wearing slinky, expensive lingerie.

The girls weren't bisexual or anything. But they certainly masturbated and got themselves off watching me fuck the other's brains out. After screwing them individually to screaming orgasms, I set them on all fours side-by-side and doggy-drilled them, swapping back and forth every few minutes before turning them around and cumming all over both their faces.

The two of them both went to work orally reviving me after that. And if they accidentally touched each other while doing so? Well, they could live with it.

Thursday afternoon turned out to be good practice for the following night.

"Ben, can I talk to you for a minute?"

I looked over from where I was idly chatting with Emily Anderson before our fourth period class. My little sister Brooke and Emily's little brother Perry were having some relationship problems with their impending separation for the summer, and we big siblings were having a little laugh at their expense.

But Megan raised both eyebrows at me and almost nervously I excused myself from Emily. Megan and I stepped to the side and put just a little distance between us and the other students milling about and I asked, "What's up?"

Megan took a deep breath and stated, "You're going out with the Sanders twins tonight."

"Yeah. Why? Is that a problem? They said they talked to you first."

"They did. It's okay. It's just..." Megan took another deep breath. "I thought you should know what they're planning for tonight."

My eyebrows pinched inward. "Huh?"

Megan sighed and glanced around. And in a secretive voice, she leaned in and said, "Look, there's no easy way to put this. The girls want you to take their virginities."

My eyes flew wide open. "WHAT?"

"Shh! Not so loud!" Megan hissed as she stepped forward and clamped a hand over my mouth. Several people stopped to glance over at us and Megan sort of grinned nervously at them while turning beet red. After a few seconds, she pulled her hand away and then shuffled us another few feet away from any bystanders.

"They always liked you, Ben," Megan said quietly. "Even when you were dating me and Cassidy, they would pepper us with questions about what you were like and all. And she and I told them all the stories about how wonderful you were and what sex was like."

So that's how my "reputation" got out. Again, I would never understand the double-standard where guys weren't allowed to talk about their conquests but girls could spread the rumor mill like wildfire. I suppose it had something to do with guys "bragging" and girls just excited to inform their friends, but whatever the motives, people's personal lives were made public knowledge.

Megan saw me scowl and smirked. "C'mon Ben, it was all good and you know it. Besides, haven't you noticed how the Sanders twins have been actively flirting with you since Prom?"

"Well..." I hedged. A LOT of girls had been flirting with me. "I just thought they were having some fun. They're cute and they know I'd never take it the wrong way."

"Nuh-uh," Megan shook her head. "You'd have been taking it the right way. You do make them horny. Anyways, the girls are convinced that you won't be single and available for long. It's taken them months to convince themselves that they're ready for sex, and they finally worked themselves up to asking me and Cassidy just on Wednesday."

I frowned. This was a delicate situation. I knew just how precious a girl's virginity was to her, and how it was always mentally built into this momentous occasion. I'd only had two virgins in my life: Dawn and Megan. Both girls were very important to me and my emotional feelings for them were part of what made those two occasions very special. "I'm not sure I can do that, Megan. I mean, I'm friends with the girls and all, but not like that. Don't you think they should wait until they find the right guys?"

Megan exhaled. "I thought so. But from the way Abbie and Allie were talking about it, you might do them more harm than good if you turn them down. You've got a reputation Ben, a reputation for sleeping with any girl that offers."

"I don't!"

"They think you do," Megan shook her head. "And if you reject them, they'll feel they're the only ones you rejected and it'll destroy their self-confidence. They know they're not the tallest or prettiest or have the biggest boobs. Their self- esteem isn't that hot to begin with."

I buried my face in my palm and groaned. "Then what do I do?"

Megan smiled and put her hand on my chest. "Just be gentle with them, Ben. You were MY first and I'll never regret that."

I bit my lip. And in a worried voice, I moaned, "But this is their virginity, Megan."

Megan smiled and moved her hand up to my cheek. "You're sweet, you know that, Ben? Underneath that dick-for-brain's playboy exterior, there's a good guy's conscience somewhere."

I rolled my eyes. "Somewhere..."

"Just be good to them, Ben." Megan nodded.

I sighed. "Do you know what their plans are?"

Megan shook her head. "No, they didn't tell us. Just that they wanted to have sex with you and they wanted to clear it with us. For all I know they've lined up a motel somewhere."

"Great," I moaned sarcastically.

Megan smirked. "Look on the bright side, Ben. Two cute, 16-year-old girls want you to fuck them. I'm sure you can handle that."

I'm not usually one to dawdle, but I was five minutes late to the Sanders' front door. That's because I spent an extra five minutes sitting in my car parked on their sidewalk, contemplating what I was getting myself into.

If I went through with this, there would be some consequences. There were always consequences. Before, I just didn't care. Donna, Stacey, and Mandy were just hot chicks to me. There were no friendships to ruin and all were Seniors, destined to be gone in another few months. Any consequences wouldn't last long.

But this was Abigail and Allison Sanders. Perhaps this was just two girls wanting to rid themselves of their cherries with a guy they trusted on some level. Perhaps we'd all be able to stay friends afterwards like nothing had ever happened. But as I'd already figured out before, you can't have sex with someone and NOT have it irrevocably change your relationship.

But hey, I was just a male slut. And Megan did have a point. If I drew the line with them, the girls would forever wonder if they just weren't good enough for me. No amount of argument would convince them it was truly because I valued their friendship over the sex.

So with my dick already hard in my pants and ready for action, I walked up to the house and rang the doorbell. One of the twins opened it immediately. "You're late! I started freaking out that you weren't coming!"

My eyes popped out of my sockets as I stared at the young woman before me. The girl had styled her hair and put on makeup that enhanced the edges of her baby face, aging her into her late teens. Her outfit was suitably grown up, a little black cocktail dress that clung to her body like her baggy jeans and T-shirts never did before. Some sort of push-up bra made her tits pop out and I blinked in amazement at the sight of the pretty girl before me. "Whoa..." I grunted.

The girl started giggling as she watched me obviously ogling her, and she smiled and said, "You're forgiven."

The other twin showed up a second later, dressed IDENTICALLY. Usually I could tell the girls apart, but with the makeup and clothing, I had yet to pick out the identifying marks. I was saved when the second twin grinned at her sister. "You were right, Abbie. He does like the outfits."

I glanced at the girl who I now figured to be Allison and stammered, "You two look amazing."

"Thank you!" The twins said in stereo, and then the two girls went to collect their purses and make themselves ready to leave.

I glanced around, looking for parental evidence, only to find that there was none. "Uh, shouldn't I say hello or something to your parents?"

"Oh, they're not here," Abigail waved me off. "They're out of town visiting our Uncle. His wife just had a baby and they won't be back until tomorrow."

I felt a lump settle into my throat. "They're not here at all? Uh, do they even know you're going out on a date?"

Allison giggled. "Nope. We have the place ALL to ourselves tonight," she grinned and then hooked an arm through my elbow. "Lucky timing, huh?"

Well, that explained the location in the twins' plan to lose their virginities. Moments later, Abigail hooked her arm through my opposite elbow. I shrugged and decided to just go with the flow. "So? Where to?" I asked.

"You drive. We'll give you all the directions you need."

We wound up at a nice seafood restaurant. Nothing too outlandish, but someplace where both my jeans and the girls' black cocktail dresses were acceptable. And I made quite the impression with my matching twins on each arm.

Our waiter wasn't much older than us and he winked at me while taking our orders. Abigail caught the wink and slyly asked for a glass of wine while batting her eyelashes at the waiter, but the guy just shook his head fractionally at her, and she decided to go for a Shirley Temple instead.

I did my best to be charming and flirtatious, and the girls soaked up all my bad one-liners and too-obvious compliments like sponges, clearly happy for the attention. We all barely touched our food, and instead spent more time just enjoying being out at a nice restaurant together.

When the check came, I paid it easily over the girls' protests that THEY had asked ME out on a date. To be honest, I'd spent the last couple of months banging chicks but not going out on any dates, so I'd built up enough savings to not flinch at the expensive dinner.

After all, it was a small price to pay for two teenage virginities.

But after that momentary haggle over the check, both Abigail and Allison became increasingly anxious. And before we left the restaurant, the girls went into the restroom to "freshen up".

They were somewhat calmed down when they emerged, I assume from some form of reassuring conversation. And as we approached my car I swept my arm out and asked, "So what's next on the agenda? Would you ladies like to go for a nice walk around the lake?"

"No," Abigail cut me off. "Take us home."

I blinked in surprise. "Did I do something wrong?"

"Not at all," Abigail shook her head, raising her eyebrows and giving me an intense look. "But we'd like to be at home for what comes next." The weight in her voice left no doubt as to what she meant.

I took a deep breath and returned the intensity of Abigail's gaze. And very softly, I said, "You girls don't need to do anything tonight. We're friends and I enjoy just being in your company."

Abigail didn't say another word. Instead, she simply moved right up into my personal space, wrapped her arms around my neck, and elevated up on her tiptoes so that her face could reach mine. And then she planted a very firm, very insistent kiss on my lips.

She still had the cherry flavor of her Shirley Temple on her lips and in addition to the sweet taste, I felt a surge of hormones flood through me as this nubile young woman pressed her entire body against me. Her tongue briefly darted into my mouth, and then she pulled away with a big smile and sparkling eyes.

I only had a moment to breathe before Allison was suddenly upon me, her kiss feeling just like Abigail's and yet just slightly different. And by the time she pulled her tongue out of my mouth and licked my lips a final time, my knees had become rather wobbly.

"Take us home, Ben," Allison insisted.

I fished my keys out of my pocket.

Things were quiet on the drive back to the Sanders home. Since Abigail had sat up front with me on the way to the restaurant, Allison got to sit up front on the return home. The younger twin kept her hand on my thigh for the entire drive, but both girls were silent the whole drive back, lost in their thoughts.

The silence continued upon arrival. Allison let herself out the passenger side but Abigail let me open her door and take her hand when she exited the rear seat behind me. And then Abigail quickly led me into the house.

Once inside, I was ushered into the girls' bedroom, a space that was dominated by the side-by-side twin beds separated only by a nightstand. The bed on the left was dressed in pastel blue linens and the one on the right was in pastel green. And four hands pushed me into a sitting position on the blue bed.

Allison attacked me then, throwing herself at my face with enough force to topple me onto my back while she leaned over me and kisses me with a ferocity I never would have guessed in the petite brunette.

Abigail, on the other hand, seemed to have a more direct mind as I felt her hands frantically tugging at my jeans, attempting to figure out how to work the clasp and zipper before she started yanking downwards on the waistband.

I lifted my hips to help Abigail's disrobing efforts while wrapping my hands behind Allison's head as I showed her everything I knew about french kissing. But a minute later, my neck suddenly went stiff and I was unable to kiss Allison any further when I felt my cock being swallowed by a hot little mouth.

My sudden inertness and moan got Allison's attention, and the slightly younger twin turned around and barked, "Abbie! No cheating! We were going to do that together!"

"Mmph!" Abigail grunted before lifting herself free of my cock. "Couldn't wait, Allie." And then the older twin looked over at me. "Am I doing it right?"

I groaned. "You're doing great. Your first time?"

Abbie (I found myself thinking of the twins by the nicknames they loved using) nodded and then resumed her experimental cocksucking. Allie went to go and challenge her sister for a moment, but I grabbed the younger twin and turned her head to me. "Let her. I've got something else for you to try first."

"What?" Allie asked with a smile.

I grinned. "Take off your panties."

The petite brunette smiled, her brown eyes seeming to get lighter and brighter as she stepped off the bed and then snaked her panties down to her ankles from beneath her dress. Her shoes followed and then at my direction, the 16-year-old cutie was straddling my head and lowering her neatly-trimmed crotch to my face.

"You're going to love this," I told her. And then I dove in.

I was right. Allie loved it.

In fact, Allie was so vocal in her appreciation of my cunnilingus that when she shrieked and came, Abbie left my cock and demanded a turn of her own. So like a wobbly newborn deer, Allie moved herself over so that she was half-seated on the bed next to my shoulder, with her legs dangling over the side.

Abbie had similarly removed her panties and shoes, but when she went to lower herself onto my face, Allie told her to take off the rest of her dress so that she could see. Earlier, the hem of the cocktail dress had been draped over my head and effectively blocked the sexual act from outside view.