Happy Birthday, Beautiful Boy Ch. 02

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The Bennings' sexy daughter gives shy Jared some coaching.
15.9k words
4.88
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13

Part 2 of the 2 part series

Updated 06/10/2023
Created 09/10/2021
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This is, of course, a second installment to my 2021 Summer Lovin' contest entry "Happy Birthday, Beautiful Boy." If you've read that story, you will quickly find what appears to be a glaring inconsistency: The close friendship between Jared and the Bennings' youngest daughter Tabitha (the daughter who was away on a camping trip in chapter 1), which was not mentioned. This story is not a RetCon but the victim of an editing error. I originally had a brief paragraph in story #1 explaining their friendship; I didn't go into great detail because it wasn't relevant to that particular story. In my rush to get it edited down and submitted under deadline, I dropped that paragraph, forgetting that it was essential to setting up the next chapter. My bad. HB,BB was my first Literotica story and my first work of fiction in over 25 years, so it's a little rough. Mea culpa. I'm working on improving my writing. Now on with the story.

Happy Birthday, Beautiful Boy pt.02

JARED

I finished washing my hands and putting on my shoes to make the quick trip next door. I needed to tell Mr. Bennings - er, Jim (I still couldn't get used to the first-name basis; I'd been calling them Mr. and Mrs. B. for years) when I would be available to mow their lawn. My summer classes were over but I still had a week left at my part-time job and I wanted him to know my schedule for the week.

Oh, by the way, my name's Jared. I just graduated from high school at the end of May, and I was getting ready to go away to college in two weeks. I was excited but nervous as hell. I was taking some Advanced Placement classes over the summer to help me skip over some of the intro courses at university, and wondered if I hadn't bitten off more than I could chew. My grades were good in the summer classes, though, so I crossed my fingers and got ready to jump into the deep end.

The school had given me the contact info for my assigned dorm buddy, and much to my relief we'd hit it off... we liked the same video games, the same music, the same movies, and had similar senses of humor. I was a little worried at first, because he was more of a jock - real big on soccer and lacrosse - and with the exception of the swim team, I really wasn't all that much of an athlete. And athletes can be real pricks to non-athletes. I knew that from experience.

See, I'm not really a very masculine guy. I'm not gay, and I don't think I act effeminate, but nothing about me screams "macho." I'm 5 foot 10, but have always been slight of build. I swam competitively throughout high school, and I've always eaten right (my mom's a real health freak and cooks accordingly), so I actually have some definition and cuts where my muscles are, but they're frankly just not very big. I never got the wide shoulders and V-back that people associate with swimmers; I look more like a distance runner. But it's the long legs, long fingers, high cheekbones, and big eyes that screwed me. All attributes that are considered attractive in girls. Not guys.

Pretty-boy. That's what they called me. And that was from the respectful ones... of course there were those that were a little more blunt: Faggot. Tranny. Princess. Girly-man. He-She. Twink. The list goes on and on. The girls at school never called me handsome or hot; they said I was pretty. And when I protested they swore up and down that that wasn't an insult, but I sure as fuck felt insulted. I didn't want to meet girls who wanted to put me in a dress and have a tea party, I wanted a girl who wanted to get naked with me. But that was never to be found.

And so the years went by, with guys making fun of me and girls never letting me feel masculine, and my naturally shy nature grew to crushing proportions. As I got more and more socially awkward, I watched the girls preening for the jocks and the bad-boys and I just accepted it and despaired. In my interactions with others I just got more passive and shy, which - of course - just attracted more abuse from the Dude-Bro collective. I was happy to leave the high school where everyone knew me, but dreaded what might be awaiting me in college.

So anyway, back to the thread... sorry, I kind of go off track a lot... I contacted my assigned roommate, Blaise (yeah, seriously, that's really his name), and we emailed, and then talked on the phone, and then did a Zoom call on video, and we totally hit it off. The video call must have lasted an hour, and we were cracking each other up and sharing stories like we'd known each other for years. He was a sophomore, and had no problems with hosting a freshman. Not even a shy, skinny pretty-boy freshman like me. And that gave me a major feeling of relief.

So, back to the present... I mentioned washing my hands before heading next door, and it's embarrassing to explain why, but here it is: Mrs. Bennings is the hottest, sexiest, most gorgeous woman on planet earth, and for the past three weeks, I've had to jerk off before I visit to ward off the massive hard-on I would otherwise get. Why the past three weeks? Because three weeks ago, on my eighteenth birthday, Mrs. B. sucked my dick. Yeah. She did that, swear to God. And she wasn't cheating on her husband; he was right there, videoing the whole thing. Not that I noticed at the time.

See, for the last nine or ten years, I've gone over to see Jim and Marie and Marie would give me a birthday present, a fresh-baked apple pie. She makes a pie that nations would go to war over, trust me. They're that good. Anyway, I went there that day for my pie and birthday greetings and she comes out of the pool in this teeny-tiny gold bikini that would get you arrested for wearing it in public. And then she has me rub suntan oil all over her body... and I mean All. Over. Her Body. ALL over. And she's acting all seductive and teasing me and I'm freaking out and having an out-of-body experience because I've been stupid in love with her since I was eight and she's a freaking sex goddess. And then... I know you won't believe me, but I don't care because I've got the video to prove it... she pulls out my dick and sucks me off.

It was quick... embarrassingly, I didn't last long at all... 93.4 seconds, to be exact, according to the counter on my video player... but considering how intensely she'd worked me up I'm surprised I held out that long. During that long, drawn out teasing session from the moment she'd risen from the pool, she was working me hard. Her body movement, her seductive talk, her playful voice... she was playing the part of seductress, it was obvious. She was putting on a show to make my eighteenth birthday the most memorable ever. And she succeeded, in spades.

And so I've taken to whacking off before going next door so as to avoid the embarrassment of popping a raging woody at first sight of Marie. And so it was with a sense of relaxed confidence that I fingered the latch on their backyard gate and slipped in.

"Helloooo... Jim? Marie?"

"Yo, Jared!" came the answering call. I smiled broadly.

"Hey, Tab!" as I peeked around the privacy screen. The little strawberry-blonde hottie in the bikini stretched out on the chaise lounge welcomed me with her trademark wide, open-mouthed Cheshire grin. She reached her arm out, fingers splayed, and opened and closed her hand, ending in an open palm inviting a high-five.

Tabby is Jim and Marie's younger daughter, and she's totally cool. She's two years older than me, but we'd teamed up as soon as my family moved here and we've remained good friends ever since. We played together almost daily for a while, and never once did she try to dress me up for a tea party - no, she was a tomboy and wanted to do all the things a young boy would do. We climbed trees, had snowball fights, stomped in puddles and wrestled in the mud after a rain. All the things that make for a solid childhood friendship.

As years... and puberty... took their toll, Tabby outgrew the tomboy thing and became more girly. And increasingly prettier. But she never ghosted me or dismissed me as a geek. We remained friends always, even though we saw less of each other. We hung out, played lots of video games, watched a lot of movies, ate fast food, fought, made up, swam, shared (and kept) secrets, got in trouble... all the things that make for a solid teenage friendship.

And because she was so pretty, she always had a boyfriend and I never had the guts to ask her out.

But that was cool because she was still my friend and would stay my friend, and that's something money can't buy.

Our palms met with a resounding smack. "Dude... the summer's almost over and I've barely seen you," she pouted. "We haven't hung out hardly at all. And you're leaving in a couple weeks."

"Yeah," I agreed, disappointed. "Hasn't been a normal summer at all. With me taking classes and working all the time, our schedules just never line up. And your camping trip..."

"Oh, God, dude, I am so sorry about that... the group set up the date and I couldn't pass up that mountain hike. I mean... I missed your graduation because of that stupid extra credit project at school, and then I ditched your birthday for the trip. I am so sorry. I feel like I haven't been much of a friend this summer."

"Hey, enough of that crap. Tab, you're the best friend any guy could want. Schedules just suck sometimes. Life happens, reality, all that happy horseshit... we're cool. We'll always be cool."

She beamed at me, her mouth twisting into a wry smile, and she reached out for a fist-bump.

"Oh, hey, I forgot why I was here... your folks home?"

"No, they're out, not supposed to be home 'til around 4. Why?" She pulled her sunglasses down and grinned slyly up at me. "You wanna see my mom?"

I felt my face get hot. "No! I mean, I just want to talk to your dad about getting the lawn mowed for the next couple weeks. You know, since I'm leaving soon."

"Uh-huh. I believe you. No, seriously, I do," she said with a smirk that implied that no, she did not. She knew my infatuation with her mother and loved to tease me about it. "Oh, hey... you busy for the next couple hours?"

"No. Got some ideas?"

"Go get your suit on! Dunno if we're gonna get any more chances before you leave for school. We gotta make up for lost time."

"Diggit! I'll be back in a minute."

I trotted back to my house and headed upstairs to my room. I was happy to finally get some pool time in with Tabby since we hadn't had much success hanging out over the busy summer. As I put on my trunks I thought about all the hours we'd spent splashing around in that pool over the last ten years. We'd always had fun, but over the last few years I'd gained a whole new level of enjoyment from our swim time. Tabitha Bennings in a bikini is a sight every male should see before he dies.

While she didn't inherit her mom's outrageously curvy body, she definitely wasn't lacking. Not very tall - she stood about 5 foot 2 - and she rocked a pair of some of the most perfect titties I'd ever seen. While not huge, they were round and firm and plenty big enough, standing out from her chest proudly, had the perfect amount of jiggle when she moved, and if she was wearing the right clothing, presented some truly mouth-watering cleavage.

She'd catch me looking, as I was inclined to do - hey, I can't help it - and tease me about it, but it was all in good fun and she never got angry about it. What she didn't see so much is how mesmerized I was by her perfect ass, which Marie clearly had some genetic influence on. Full, round, and oh so squeezable and spankable.

But she was my friend, who I grew up with, so I knew I wouldn't be squeezing or spanking that tasty ass, or fondling and caressing those perfect tits. She was almost my older sister, for fuck's sake. And yeah, she was only 2 years older than me, but she was just a few months shy of 21 and ran with a different crowd and had boyfriends. So no, those fantasies about my best friend that started bubbling up over the last few years would remain just that - fantasies - and I had no problem with continuing to view her as a good friend. The images that perked up in my mind of her imagined nakedness and all the hot and naughty things we could do together would remain my dirty little secret.

I put on my sandals, grabbed a towel, went down the stairs and headed for the back door. "I'm going swimming next door, Mom."

"We eat at five," came her reply from the kitchen, "just get back before then. Have fun."

As I reached the gate to the backyard of Chez B., instead of announcing my presence as usual I gently undid the latch and slipped inside, gingerly closing the gate. I quietly made my way around the trellis and privacy wall and peeked around, hoping to catch Tabby unawares. And boy did I call it... she was standing up, slicking herself down with suntan lotion. Her back was to me, and she was working the lotion into her lower back as high as she could reach. Once well covered, she squirted another generous bloop into her hand, set the bottle down and rubbed her hands together before - oh, glory hallelujah - putting her hands to the cheeks of her ass and rubbing it in.

As the sun gleamed off of the slick flesh being kneaded and massaged, my mind went simultaneously to two places - the edge of the hot tub, weeks ago, when the devious Marie had me massage tanning oil into her luscious booty, and poolside right now, where, in my mind, I was the one rubbing lotion into Tabitha's beautiful ass. It started to feel increasingly crowded in my swim trunks as I drank in the vision of her supple, sexy body in sensual motion while she was completely, innocently unaware of my presence.

"I know you're watching me, you fuckin' perv, I heard you creep through the gate... now get over here and do my back for me!"

She turned toward me, reaching out with bottle in hand, smirking. "Creeper!"

I laughed, blushing. "Hey, I'm eighteen. It's part of the job description." I tossed down my towel and squirted some lotion into my hand as she faced away, gathering up her long, wavy strawberry blonde locks in a ponytail and lifting them over her head. I slicked my hands together and laid them on her shoulder blades. As I worked the lotion into her shoulders and down her back, I drank in the beautiful golden-brown hue of her soft skin. I didn't see any evidence of tan lines, and I pictured her lying naked in the sun. I pushed the image out of my head to avoid the inevitable boner that was starting to wake up. "You get a lot more tan than your mom does."

"Yeah, it sucks. I feel sorry for her. She can get a little color but has to be really careful or she freckles. I think freckles are cute but she hates them. My dad's side of the family gets really dark though, so I lucked out.

As I massaged the lotion up and down the sides of her ribs I copped a little bilateral side-boobage. Just a glancing touch, easy to brush off as an accident.

"Gettin' a little handsy there, tiger!"

"I didn't mean it! It was an accident," I protested.

"Uh-huh," she said as she shot me a knowing smirk over her shoulder. She reached for the bottle of lotion. "Shall I do you now?" The double-entendre was accented by her arched eyebrow and I felt a faint tingle downstairs.

"Tab, you can do me anytime, anywhere." I turned my back to her in time to receive a playful slap on my shoulder. I chuckled.

"Yeah, I handed you that one on a platter." Her soft hands felt like heaven on my back as she worked the warm, slippery goo into my skin. I purred like a kitten. I felt her hold me by my shoulders as she stood on tiptoe and whispered in my ear, "Try not to enjoy it too much... remember you're wearing swim trunks." I felt my face heat up.

When we were both sufficiently SPF'ed she threw a volleyball into the pool and we did two simultaneous cannonballs into the rippling water. Laughing as we came up for air, we commenced to batting the ball back and forth, chattering on about anything and everything. We splashed each other and played and joked and just enjoyed each others company. At some point we stopped for a breather, hanging onto the edge of the pool, side by side. We hung there in silence, enjoying the sun and cool water. Tabby was watching me, not saying anything, just seeming to study my face with the faintest of smiles playing on her pretty pink lips.

"What?"

"What what?"

"Why do you keep looking at me like that?"

"Maybe I just like looking at you?"

I just stared out at nothing in particular and sighed. "Because I'm so pretty, right?"

"Hey, don't knock it. You've seen how swoony and stupid girls get over those boy-bands, and none of those guys are exactly macho men. They're all pretty-boys, and they could leave with the panties of every chick in the audience if they wanted. You've got a big advantage with girls over a lot of other guys if you just use it right."

"What do you mean, 'use it right?'"

"I mean your looks can set the hook but there's some other things you need to get down in order to reel them in."

"Like what?"

"Well..." she pursed her lips and gazed out momentarily as she arranged her thoughts, "The most important one I guess is the introduction and conversation part, 'cuz that's where it all starts. I mean, if there's no beginning, there's not gonna be a middle or an end, right?"

"Makes sense. And that's where I'm doomed. I'm just nervous around girls and... I don't know where to start. How to start. I can't get past that."

"Bullshit." Her voice was firm and final. "You can, and you will." It softened again. "Never say 'can't.' You're just reinforcing it if you tell yourself that. Think of all the pluses you have and think about those instead and... just let that boost your confidence. You're gorgeous, you've got a fun sense of humor, and a super sweet personality with a beautiful smile and a big dick - what girl could ask for more?"

"Wait, what? How would you know anything about my dick? You've never seen it."

She flushed bright red and hastily looked away, with a wide-eyed "I fucked up" expression on her face.

"Oh, that's a guilty look if I ever saw one! Spill it, Tab!"

She sheepishly turned back to face me. "I saw your movie," she replied in a small voice.

I felt a knot form in my stomach.

"What movie?"

"With Mom. Your, um, birthday present."

Now it was my turn to go beet red. "Oh my God! Tabby!" My head was still reeling from the events by this very pool just a few weeks ago. I was confident that the video I'd been stroking off to lately was only seen by me, Jim, and Marie. But now I discover that it's been seen by an outsider; my childhood friend and Marie's very own daughter, no less. I was mortified, just staring at her with what had to be a look of pure helplessness and embarrassment. "I... I..."

Tabby pushed forward through the water and wrapped her arms around me in a bear hug. "Hey, dude, it's cool. Relax." Her right hand stroked up and down my back. "I know my mom is like this crazy sex machine... I guess she just figured that a blowie would make your eighteenth birthday extra special. No big deal. And it's not like she was cheating on Dad; he was obviously in on it. I mean he was the cameraman, for fuck's sake."

"But they're your parents! That's gotta be disturbing to see. And I've never heard anybody else call their own mom a 'crazy sex machine.'"

She released me and backed away to look up at me, much to my relief because those beautiful boobs mashing up against my chest were getting things stirring downstairs, if you catch my drift. She rolled her eyes. "Dude, you have no idea what it's like living with those two. It's like they have to physically restrain themselves to keep their hands off each other. And they're fucking all the time... they think they're being quiet but they're really not, not enough to hide it, anyway. That's one of the reasons Sarah moved out as soon as she could; she's kind of a tight-ass and it was just TMI for her to stick around any longer than she had to. And Mom is definitely the wilder and crazier one of the two. They've been making homemade pornos for years."