Chapter 6: Samantha

“Ohhh ... shiiiiit...” Sam sighed as she shoved my head out of her crotch and curled up into a fetal position on her side. I’d been eating her out for more than half an hour, in no rush because for once I didn’t have any time constraints. I wasn’t trying to sneak in a quickie before school, like I’d done with Belle yesterday morning. There were no friends watching us and waiting for their turn, like this afternoon’s study session with Alice and Naimh. It was just me and Sam tonight, and I wouldn’t have it any other way.

It was Wednesday night, late enough in the evening that I’d been surprised when the doorbell rang and I found the platinum-blonde Aussie standing on my doorstep with her arms crossed beneath her big breasts, squishing them together to create amazing cleavage in her V-neck sweater. She’d asked if I was busy, admitted she was horny, and sweetly pleaded for me to go down on her. I didn’t need any further convincing.

“I think moving this into your bedroom was a BAD idea,” she panted, looking unbelievably sexy with tousled hair and her bare skin shimmering with sweat. “You have NO idea how tempted I am to have you come up here and just slide it into me.”

I picked my head up, blinked at her a few times, and let my eyes rove all over the busty blonde bombshell’s bodaciously beautiful body. “Um, yes please?” I said with a smirk, only half-joking. I then sat up and reached for the box of tissues on my nightstand to dry myself off. The entire lower half of my face was absolutely soaked in girlcum.

Sam giggled at my playful tone and sighed, shaking her head rather mournfully. “You know what I love most about you? I know you’ll never do anything I don’t want you to do. I feel safe. I trust you. I’ve never felt that way with other guys. The last time I let a boy eat me out, he barely made me cum before he was hovering on top of me, nudging his dickhead against the entrance to my pussy and begging me to let him push it in.”

The idea of some meathead in that position over Sam immediately killed any arousal I felt, and with narrowed eyes and a bit of a growl, I intoned, “You didn’t let him, did you?”

“You jealous?” Sam laughed and shook her head. “No, of course I didn’t let him. We’d only been on like three dates and after his pathetic rug-munching, I realized I didn’t want to sleep with him. I did give him a courtesy blowjob to get him to leave, but we never went on another date after that.” She shrugged like it was no big deal.

“I’m sorry,” I apologized. “I shouldn’t have asked.”

“No, it’s okay. You’re one of the BTC.” She gave me a brilliant smile. “We share everything.”

I arched an eyebrow and shook my head dismissively.

Sam levered herself up onto one elbow. “No, I’m serious. Ask me anything.”

I shook my head in the negative again. “I’m part of the BTC, but I’m not one of the girls. A gentleman doesn’t ask such things.”

“But you’re still curious, aren’t you?” Her eyes twinkled.

“Anyone would be, but I still would never ask you that stuff.” I shrugged. “I respect you too much for that, and I’m not the kind of guy who would devalue a girl based on her sexual history.”

“Easy for you to say with this crowd. Everyone but me and Neevie is still virginal and pure. Neevie’s only been with one guy her whole life, well ... up until she gave you those blowjobs last Friday. That makes me the resident slut with a number of ‘two’.”

I arched an eyebrow. “Still at ‘two’? I always wondered if you hooked up with Jake Pedson at Junior Prom.”

Now Sam arched an eyebrow at me. “Thought you just said you’d never ask me that stuff.”

I winced and sat up straight, holding out both hands defensively. “You’re right, you’re right. My sincere apologies, mademoiselle.”

Sam laughed musically, and her Aussie accent made her next words sound even more playful. “Don’t apologize. I already said you could ask me anything.” There was a world of innuendo in her voice.

“Anything?” I asked with a tease. I was pretty sure she wasn’t talking about asking questions anymore.

“Anything,” she assured me. “And no, Jake Pedson squirted his shorts in the limo when I put his face in-between these two beauties.” Sam hefted her big naked boobs for emphasis, mashing them together and rubbing one up and the other down before reversing course over and again, like a pair of cheerleader pom-poms. If she kept that up much longer, I’d squirt my shorts too, if I were wearing any. “You, on the other hand, will get a LOT farther than he ever did. All you have to do is ask.”

“Um, does that mean I can ask for a blowjob now?” I asked innocently, staring at those pom-pom boobs.

Sam giggled. “Why yes, sir, you may.”

“And can I ask you to let me fuck your tits again?”

She laughed and repeated, “Why yes, sir, you may.”

“And will you swallow every drop of sperm I give you?”

Sam thought about that and grinned, shaking her head ‘no’.

I arched an eyebrow, confused.

Sam’s eyes glittered. “I want you to cum on my face.”

Sam apparently had such a great time Wednesday night that she came back again Thursday. I was a little drained from my regular Thursday afternoon “study breaks” with Belle and Mari, although I couldn’t go down on Belle because she was on her period. But my mouth was in perfectly good working order, and this time Sam wanted me to start pushing my fingers inside her. I was more than happy to learn new tricks. The virgins of the group might be a little skittish about that sort of thing, but I would have bet my left nut Naimh would be thrilled the first time I tried it out on her.

Sam and I got quite a shock when we headed downstairs and found that Mother had come home a little earlier than usual. At least we were fully dressed. Sam blushed bright pink but made polite small talk. Mother had interacted with each of the BTC girls in passing several times each year, so they at least knew each other. Eventually, Sam gracefully made an exit, and after she was gone, Mother fixed me with a serious look.

“Did you use protection?” she asked rather bluntly.

I blinked twice. “Uh, we didn’t have sex.”

“Really?” Mother looked surprised. “It sure sounded like you two were having a good time.”

I frowned. “I’m still a virgin.”

Mother pointedly looked toward the front door where Sam had just left and then looked back at me. “Not for long.”

I arched an eyebrow. “What’s that supposed to mean?”

Mother smiled thinly. “Make sure Samantha is on birth control, and buy yourself some condoms just in case. I don’t want the two of you going through what your father and I had to go through.”

I sighed and shook my head, already walking out of the room. “Thanks for the reminder I’m nothing but an unwanted accident.”

“Matthew,” Mother called, but I was already heading for the stairs.

“Mari ... Angel ... I’m gonna cum...” I warned, gasping for air as I watched the lovely Latina bob her head up and down my prick, her lips stretched wide around my girth. It was a regular Friday BTC hangout, and at the moment I was seated on the couch with no one else around but me and her since the other girls had been satisfied and moved along. Naimh, Belle, and Mari were presently chatting around the kitchen island, and Sam and Zofi were in the office putting their clothes back on after our latest group expedition into exploring the uncharted territory recently made available after pushing The Rule’s boundaries further and further out.

See, for a long, long time, each of the girls had long spent her days using me as a crash test dummy to practice flirting: tossing her hair, batting her eyelashes, pretending to absentmindedly tug at the V-neck of her sweater and expose millimeter after millimeter of additional titflesh, etc. They’d been testing out their seductress skills on me for a while now, but over the past week, actual nudity had been added to the menu and happy endings were allowed for all. And knowing that all that teasing and flirting could ACTUALLY end up with an orgasm or two for both parties involved made a TON of difference.

Instead of almost exposing a nipple when playing with the buttons on her sweater and dry-humping my erection on Monday after school, Sam went ahead and gave me a few peeks while batting her eyelashes at me coquettishly, only to cover her tits up again. Minutes later, Naimh one-upped her by unbuttoning herself all the way and then pulling my mouth around her swollen teat. Minutes after that, Sam gave me a titfuck that ended with a wet and sloppy facial.

Zofi had always loved to sashay past me doing a model’s runway walk before glancing back to make sure I was checking out her high and tight ballerina butt. On Tuesday, she paused a few feet away, pulled her jeans down to mid-thigh, bent over, and waggled her toned tushie at me before giggling and scampering away. An hour later, when she repeated the maneuver, I leapt out of my chair and went after her. She issued a high-pitched squeal as I pounced, unable to retreat with her pulled-down jeans obstructing her legs’ freedom of movement. I caught her easily around the waist and spun her around once before putting her back on the ground and lightly spanking her bare butt. She looked back over her shoulder at me in surprise at the unexpectedly aggressive act (for me, at least). With a mischievous glint in her eye, she then shook her butt at me again in defiance. Taking the cue, I bent her over and fell to my knees so I could lick her succulent snatch from behind.

Alice was more direct. When she wanted a study break, she just dropped into my lap, pulled her shirt and bra up to her chin, and shoved a nipple into my mouth. Five minutes later, she sat back in the armchair with her legs thrown over my shoulders while I feasted on her.

Now it was Friday, and the girls decided to have a little “nude in high heels bootcamp” to further their education in becoming good and proper sex kittens and learn the art of seduction sans clothes. In the past, when the girls would flaunt themselves before me, I was expected to keep my hands to myself. Today, they’d demanded that -I- be the first to strip. Not for any solidarity with the girls or sense of fairness mind you, but simply so they could have easy access. So while in theory I too would be getting used to being nude around the girls, in practice, for most of the afternoon my nudity was obscured by the head of a budding fellatrix.

Long story short, it wasn’t long before I was most definitely comfortable in my own skin.

For the better part of two hours, Sam, Zofi, Naimh, Alice, and Mari took turns parading around my house without a stitch of clothing save for high heels - practicing their runway walks, testing out optimal angles for presenting me with their naked asses while simultaneously twisting their torsos to put their big bosoms in profile, things like that. Belle also paraded around, but since she was still on her period she was the only one who kept her panties on the whole time.

The girls would go up one at a time, with the rest of us sitting on the family room furniture we’d pushed back to give them the runway space to practice their moves. Sam took the honors of calling out and demonstrating many of the moves, though most of the girls came up with at least one pose they wanted to try out with the group watching.

What followed was vintage BTC. My friends cheered and supported each other from the audience, giving tips without judgment and giving encouragement when they got the move just “right” (in my opinion, they never got it wrong).

Shy Mari faltered during her opening strip tease, momentarily reverting to the nightmare of being a scared girl standing in the middle of a room wearing nothing but her underwear and everyone staring at her. I don’t know who started it, but soon we had a chant going, “Ma-ri! Ma-ri! Ma-ri!” while we all slapped the cushions on each syllable. Naimh called out from the loveseat in a hybrid Irish/Cajun accent, “You can do it!”

It would probably be an exaggeration to say that Mari finished the strip tease like a pro, but off came her bra, with her panties following soon after while everyone encouraged her with catcalls and whistles. Most importantly, when the lush, curvaceous Latina finished her final pose, her back to us, one foot on a coffee table as she swung her hips back and forth with her panties still dangling from her fingertips, Mari turned to us and her smile lit up the room as Belle ran to hug her BFF clad only in her panties, squishing their big boobs between them.

Then there was that moment when blonde bombshell Sam attempted to lean back against the doorframe to the downstairs office. She’d meant to use it for leverage as she wiggled her body down and back up again like a pole dancer as Neevie had demonstrated for us, but she misjudged where she was and almost completely missed the doorframe. Her eyes went wide as the expected support didn’t arrive and she fell backwards right through door, completely eating it right in front of us. Several of the girls yelped in surprise as we all scrambled to see if she was okay.

Sam looked up at our anxious faces and answered our voiced concern for her with a chagrined, “I fell on my butt,” drawing a laugh from each of us. Alice suggested I kiss the boo-boo, which I was only too happy to do.

Sam tried again and pulled it off, the incident passing into legend amongst the BTC.

While those moments of comradery were memorable, the parade of flesh was exquisite. Willowy Zofi, of course, excelled with her natural dancer’s grace. Extroverted Sam, Naimh, and Belle vamped it up and took great glee in shaking their goodies for me. Even Mari warmed up as the afternoon went on.

One benefit of always having either Belle, Naimh, Sam, or Mari slurping away on my dick was that I felt no need for ejaculatory control. And so it was that when the most gorgeous thing I’d ever seen paused to lick two of her fingers before swiping them through her red-furred landing strip and across her clit after a turn on our little catwalk, my hips jerked and Sam happily swallowed my first of three loads that afternoon. Naimh seemed particularly proud of herself for that one.

Then there was Alice. Like Mari, Alice was a more hesitant participant and would cover herself up with bathrobes between sessions. She’d never frozen as Mari had, and she wasn’t the only one to cover up when not performing (Mari retreated into a bathrobe as well, and Zofi had taken to wearing her panties like Belle, not for modesty’s sake but rather because she liked the way I’d started staring at her panty-clad ass, even with all the other naked tushies around). But regardless, my best friend was clearly feeling awkward. I was beginning to consider asking if she wanted to sit the rest of the day out.

That’s when Sam had the bright idea to have each girl take a turn sitting in my lap wriggling her naked heinie in my lap. For this, Sam asked that I put my boxers back on. No need to tempt fate (or Naimh) that things would line up just right and cost someone their virginity. It wasn’t a far cry from the dry humping Sam had begun last summer, but now there was less clothing in the way and I was also allowed to touch and grab to my heart’s content. First went Sam, who ground out an orgasm for herself before her dismount. Mari and Zofi followed after.

Once their turns were over, my best friend took her place. Now, while Sam had ground herself against my erection, Mari and Zofi had mostly been content to cuddle, with Mari taking the extra step of feeding me her nipple. As such, I’d actually had less direct physical stimulus in the last few minutes than I’d had for most of the afternoon and was nowhere near losing my load.

Alice, however, wasn’t one for cuddling. And while she wasn’t a big fan of walking around naked, either, she did enjoy getting herself off and began imitating Sam’s ride. It took her a moment to figure out what worked, but eventually she was riding me like she’d been doing it for months. “Suck my titties,” she commanded, and I happily complied, leaning forward to take in the luscious love melons.

Beside us, Sam was calling time, but Alice didn’t want to stop. “Please, I’m almost there,” she whined. No one stopped her as her hips moved faster, seeking just the little bit more she’d need to go over the edge. Ignored was the effect she was having on me. I might not have been close before, but a solid five minutes of Alice undulating on my lap was bringing my balls to a boil.

Then I felt her hand between us, Alice taking matters into her own fingers as her rapid diddling of her clit also rubbed across my cock. Finally, she screeched out the orgasm she’d been chasing, wailing while her body ground down on me one last time, and I grunted as I followed her over the edge.

Alice’s eyes refocused as the wave passed. Still breathing hard, she apparently felt the moisture between our loins and looked down. “Did you...?”

I chuckled. “I certainly did.”

“For me?”

I looked back at her confused until it hit me. Alice hadn’t been awkward out of shyness; she’d been intimidated by the other girls. Sometimes I forgot the BTC were teenage girls with their own set of body issues, and we did have very beautiful friends. So I assured her with warm sincerity, “Yes, for you.”

Alice contemplated that for a moment until she looked down again and realized what was smeared between us. My erection had long been poking upwards between our two bodies, giving the girls something to grind on. But Alice’s undulations had worked the waistband of my boxers lower and lower so that the top several inches of my dick were exposed, and I’d ultimately belched my load across both of our bellies.

“Eww!” Alice abruptly complained and leapt off my lap to run into the kitchen. We could see her grabbing paper towels to first blot up my icky sperm, and then run a few more paper towels through the sink to make wet wipes. And she kept up a constant stream of complaints from the kitchen through most of Belle’s turn on my lap.

But when Alice came back, she was a lot freer and confident for the rest of the afternoon, imitating Zofi’s preference for wearing panties, but ditching the bathrobe.

Sensing that the whole “naked bootcamp” thing was winding down, Naimh was the first to break, flopping onto her back in the seat beside me and yanking me around until my face was in her crotch. I was only too happy to start feasting away.

Alice promptly pulled her panties back off and then parked herself on the couch right next to us. “I call ‘next’!”

Spending all afternoon exposing themselves to my hungry gaze had primed all of the girls, and they each climaxed quite quickly. Sam and Zofi also screeched their satisfaction in short order after Naimh and Alice. Mari held back, letting herself be last. After she finished squealing her pleasure to the ceiling, my adorable angel reached out and fondled my final erection of the afternoon between her thumb and forefinger. She patted the seat cushion and said sweetly, “Let me take care of that for you.”

Naimh, Alice, and Belle were all fully-dressed by now and chatting around the kitchen island. Sam remained naked, chilling out on the armchair a few feet away while Zofi sprawled next to us on the couch, also still naked and still a little delirious from her recent orgasm. Accepting Mari’s generous offer, I took my place on the seat, my rock-hard shaft pointing straight up to the ceiling. And I groaned in exquisite relief as my luscious Latina started lowering her warm and wet mouth around my rampant prick.

I wasn’t in any hurry to cum. I was already down two ejaculations this afternoon, and I wanted to relax and enjoy Mari’s blowjob as if it were a well-earned cigar at the end of a long day. At first, Sam watched Mari working me, and it almost looked like she was studying the other girl’s technique. But then Zofi started to stir from her stupor, and Sam went to help collect her best friend and took her back to the office to get dressed.

Eventually, though, my angel’s talented mouth started bringing me up to the edge. Pleasure shot through my brain like lightning bolts as I groaned and let my head loll against the backrest. And when I felt the pressure in my balls come to a boil, I stiffened my spine and looked down to warn her of my impending eruption.

“Mari ... Angel ... I’m gonna cum...” I warned, gasping for air as I watched the lovely Latina bob her head up and down my prick, her lips stretched wide around my girth.

Mari held up a finger, telling me to wait. She stopped her bobbing at the top, inhaled deeply through her nose, and sloooowwwlllly sank her face all the way down my dick.

I mean ALL the way down. Mari’s lips were around the very base of my cock, and the tight constriction of her throat was almost too much for me to bear.

“Holy CRAP!” I exclaimed, throwing my head back and desperately trying to hold my orgasm at bay lest I drown her in this vulnerable position. Mari stayed down there, breathing shallowly through her nose, trying to hold the deep-throat for as long as she possibly could.

“Holy CRAP!” Belle exclaimed from the direction of the kitchen. A moment later, she announced in a louder voice, “Mari’s deep-throating Matty!”

“What?!?” Sam exclaimed as she returned down the hallway. Zofi squeaked something as well. But I didn’t bother turning to look. All my attention was on the angel before me with a throat full of cock.

Mari suddenly choked and backed off quickly, thumping her chest with her fist as tears appeared in her eyes. She tried to get over it a little too quickly, putting me back into her mouth and sucking once more, but she hadn’t yet cleared her airways and she pulled off to start coughing again.

Belle quickly settled to her knees beside me and crammed me into her mouth. She didn’t bother trying to deep-throat me, she simply hummed and pumped and did that thing I loved so much with both her hands twisting around the base, and in less than a minute I grunted and began spewing semen into my “little sister’s” stomach.

With a satisfied sigh, I collapsed against the couch and smiled serenely while Belle nuzzled and nibbled at my cockhead lovingly. When I had enough energy, I raised a hand to caress her cheek, and she turned to kiss my palm and flash me an impish grin.

“Thanks, B.”

“Yeah, thanks, B,” Mari added, still tapping her chest and breathing heavily. She gave me an apologetic look and said, “Sorry to leave you hanging.”

I shook my head. “Don’t be, Angel. I loved what you did.”

“But I choked instead of making you cum.”

“Girlie,” Belle chimed in, “you got all the way down! That’s amazing! And I had your back this time. Next time, you’ll be able to say you made him cum straight into your belly.”

“IF that’s what you want,” I added. “You know I’ll be fine if you don’t.”

“Of course I know.” Mari beamed at me. “That’s why I loved doing it for you.”

With a wide, satisfied grin, I gestured for Mari to climb up and cuddle alongside me, which she did happily. I loved the feel of her lush naked curves beneath my arms. In the meantime, Belle hadn’t let go of my prick, continuing to stroke my semi-hard shaft. Having cum three times today, it wasn’t in any hurry to rise back up to full mast, not that she seemed to mind. At the moment, the petite strawberry-blonde simply wanted to play with it.

Mari had gone to get dressed and Belle was still playing with my prick when Zofi came around and held up the DVD we’d rented from Blockbuster to be tonight’s entertainment. I nodded and Zofi hollered, “We’re starting the movie!” And the rest of the girls assembled around.

Belle finally put my penis away and sat on the other cushion beside me. Alice and Naimh took the two-cushion loveseat, and Zofi was quick to call dibs on the armchair, leaving Sam out in our impromptu musical chairs game.

But Sam wasn’t interested in sitting down just yet. She stood in front of the TV, waiting until she had everyone’s attention. And then in a slightly nervous voice that was supremely out of character for the typically ultra-confident young woman, she said, “I need to ask a favor from all of you: I’d like Matty to go with me to this wedding tomorrow night.”

Zofi frowned. “You mean, like a date?”

“No, no, that’s just it. I mean, technically, yes he would be ‘my date’.” Sam did the air quotes. “But we wouldn’t be going ‘on a date’. I’m perfectly aware of The Rule. Rather, one of my dad’s business partners is getting married and I’ve already been to a half-dozen functions with these people and I’m ALWAYS getting hit on by older men who won’t take a hint even if I tell them to bugger off. I have to be nice to them because they work with my dad, but having Matty escort me would help a lot in keeping those wankers away from me, you know?”

“You both have to dress up, right?” Naimh queried.

“Of course. It’s a wedding.”

“And there’s going to be a fancy dinner,” Alice stated, rather than asked.

“Of course,” Sam sighed, recognizing where this was going.

Mari giggled. “Sounds like a date.”

Naimh added, “And I’m pretty sure The Rule clearly states that--”

“I get it, I get it,” Sam wheezed. “That’s why I’m asking permission from you instead of him.”

“Did you ask him?” Belle sat up straight before turning to me, adding, “Did she ask you?”

“Yesterday.” I shrugged. “But we knew we had to run it by you all first. Seriously, she just needs a shield, and I told her I’d be happy to do it, but only if you all were okay with it.”

Zofi leaned forward and raised both eyebrows at Sam. “You realize this’ll set a precedent for other situations where one of us will want to ‘borrow’ Matty to be an escort at some function or another. I’m not complaining - just confirming for my own selfish purposes.”

Sam rolled her eyes. “Yes.”

Zofi grinned. “I’m okay with it.”

Belle laughed. “You’re penciling him in for next Saturday or something, aren’t you?”

“I call the Saturday after that!” Naimh announced.

“Can we divvy up weekdays, too?” Mari asked.

Sam started waving her hands. “Oh no-no-no. This is NOT going to turn into some kind of rotating schedule where Mari gets him on Mondays, Neevie gets him on Tuesdays, Alice gets him on Wednesdays, etcetera. If you’re going to try and pull that shit then you can all get stuffed and hang the wedding.”

“Relax, relax, we’re just teasing,” Belle assured her. “I mean, as long as Matty’s fine with it, I say let him go with Sam. It’s not like they’re going off on some romantic escapade.”

Alice shrugged. “Yeah, no biggie.”

Naimh briefly waved both hands in a what-the-heck gesture and said, “No worries. But like Zofi, I reserve the right to borrow him if something comes up where I need a boyfriend on my arm.”

Mari nodded and said, “Sure.”

I smiled and said, “Looks like it’s unanimous.”

Zofi grinned. “But you still lost musical chairs.” She tossed a big pillow for Sam to use as seat cushion on the floor.

Sam beamed at me and said sincerely, “Totally worth it.”

“Wow ... This is pretty nice,” I commented as Sam and I walked through the front doors of the San Francisco Merchants Exchange building arm-in-arm. The wedding ceremony would take place right there in the barrel-vaulted lobby, which was decorated to the nines with golden trees topped with white flowers that accented the distinct décor. Sam looked somewhat less enthralled, so I arched an eyebrow. “Been here before already?”

She shrugged. “Second wedding. Third event overall. The company likes this place.”

“I can see why. It’s impressive.”

“Samantha!” A male voice called from somewhere to our left.

Sam winced and closed her eyes for a moment. “So it begins.” She schooled her face, put on a pleasant façade, and turned with me to face our new visitor.

“Mr. Sanderson, so nice to see you again,” Sam said politely as the early 30s man with a trim goatee strode over to us.

“How many times have I told you to call me ‘Tim’?” he said, eyes gravitating down to Sam’s upthrust cleavage. They lingered there a little longer than would be polite, but he finally brought his gaze back up. I couldn’t necessarily blame him. Sam was impeccably dressed in a satiny black dress that put “the girls” on display, black lace stockings, and fancy skyscraper high heels. Her dark roots and heavy eye makeup accented her severe appearance to go with the dress, but her platinum-blonde hair, piled high in a fancy up-do, and dangling silver earrings completed the look. Teenaged near-jailbait or not, Sam was gorgeous enough to attract the attention of everyone from twelve to a hundred and twenty.

“Perhaps one more time, Mr. Sanderson,” Sam replied primly. Turning to me, she released one of her arms from mine and gestured, “This is my boyfriend, Matthew.” She immediately wrapped both arms around my left elbow afterwards.

“Pleased to meet you,” I stated evenly, offering my hand. For whatever reason, it never occurred to me that Sam would introduce me to people as her boyfriend. I mean, I knew I was going to be her escort, but I honestly thought I would just be her “date for the evening” or something.