Roy's Conquests: Perky Jessie

*** Disclaimer ***

The following story is a work of fiction. It contains themes of cheating, cuckoldry, voyeurism, and NTR. If this isn't the fetish for you, don't waste your time flooding my inbox with hate mail-- it'll only make me want to write and post MORE cuck stuff (unless, of course, that's your goal...).

Otherwise, I love hearing from fans, and welcome any suggestions, thoughts, criticisms, or fantasy ideas. Enjoy!

***

ROY'S CONQUESTS: PERKY JESSIE

***

I can't take all the credit for the marriages that I've destroyed. Sure, I've taken plenty of happy ones, inserted my cock, and lavished in the spoils. But some of them... some of them were a powder keg ready to go off, all on their own. I merely provided the match.

Take Jessie and Michael's marriage. They were doomed to fail, the first moment I laid eyes on them. Hell, I didn't even set out to wreck that one. The opportunity sort of just fell into my lap.

Michael and Jessie were young newly weds. They owned the place next door to me, long before Courtney and Steve.

Michael was a sales rep for a pharmaceutical company. Good financial stability, good education, and good looks. Classic and tall, dark hair, groomed but perpetual five-o'clock shadow. Hell of a nice guy, with everything going for him. The type of guy that you'd feel intimidated to compete with. But the one chink in his armor was that he traveled for work... a lot. Men, why do you think that's a good idea? Are women impressed by a man who makes money? Sure they are. But why do you assume that when the cat's away, the mice won't play? Believe me, they will. And they'll make it *your* fault that they did.

Jessica. Quite the fitting name-- like the cartoon sex icon "Jessica Rabbit". All that comes to mind when you see this girl is "Va-voom, va-voom, va-voom." She was a sweet kid-- maybe 22. Married young. One of those wanna-be Disney Princesses who thought that the finish line in life was marriage, and once you did that, you spent the rest of your days coasting through montages of sharing root beer floats, and dancing in gardens with blue birds.

The first thing any sane man would notice about her-- her tits. Boy howdy, did she have some knockers on her. At least a double, possibly even a triple D-cup bra. The tits she was rocking were almost as big as her head, and all natural. Otherwise, her frame was slim, and her butt was tight, making them all the more impressive.

But you know how busty chicks tend to be a bit lack-luster in the face department? She wasn't. Oh god, was she cute! Even if she was totally flat-chested, her face was as cute as a button. Big blue eyes, turned up bunny-rabbit nose, pink rosy cheeks, pink lips, and a bright smile. She was a brunette (if that matters), but her hair was always styled a bit different each time I saw her. Sometimes she'd have highlights, sometimes she'd curl it, other times she'd throw it into a perky ponytail (like Sandy from Grease), or a tight little bouncy style that'd look like a feather duster tickling the air. Once, she'd even gotten a perm (I thought it made her look like a poodle, but she was trying, therefore it was cute enough).

Here's the clincher that really set her apart. She must have had braces when she was young, and they didn't quite finish the job, because she had this ever-so-slight overbite that made her look like a chipmunk... or a rabbit. It came complete with a little endearing speech impediment. She struggled with her R's, which came out sounding like W's. That Wascally Wabbit! Some men might disagree with me-- what's sexy about a girl who talks like Elmer Fudd? But I can tell you, each time she'd call me "Woy", my heart would melt a little inside. It was too fuckin' adorable. And to hear her scream it during an orgasm... my goodness. It was almost enough to give this old swinger a heart attack.

So how did I end up with this busty little bunny rabbit bouncing on my carrot, screaming "Fuck me, Woy! Hawder! Hawder!"?

Let me take you back to one of my hobbies that doesn't involve stealing your wives...

***

...I love being outside! I don't just mean swimming in my pool, lounging in my hottub, or laying out beneath the sun to let my packed muscles bronze to a triumphant color.

I just mean I like nature (sex is 'nature', so that makes sense). I keep quite the extensive garden that I look after and maintain. My flowers are perfectly pruned, my lawn is evenly trimmed. Yes-- I'm one of those psychos with the meticulous lawn. Sue me. I'm retired, therefore I'm allowed to be fastidious. Besides, outdoor work keeps my skin tanned, my blonde hair naturally light, and body fit.

I've said before that I always draw inspiration from Jack Lalanne. Well outdoor work helps with that, in between weights and cardio. My biceps are as large as my head, my chest is broad and hairless, my abs are washboard, and my thighs are thick, with a pair of upside V's in the right places, and what's swinging between them could certainly count as a muscle.

In my 60's, I'm more fit than the average twenty year old, so is it any wonder that I have such success with women? My hard body and unassuming demeanor versus the doughy bodies and youthful insecurities of their husbands and boyfriends. No contest.

On this particular day, I was tiptoing through my backyard, camera in hand. My target? No-- not what you think. I don't need to peep through windows to see tits, you pervs.

Nope. The gorgeous little humming bird who's been buzzing around my feeders all week was back, and I wanted some action shots!

I crept as close as I dared before steadying myself and... CLICKCLICKCLICK. I am quite the photographer, when I care to be. I repositioned myself, hoping to cut out the feeder entirely, and snap this little lady with a backdrop of my rose bushes.

CLICKCLICKCLICK. Nailed it! I squinted against the sun and smiled to myself as my new friend departed.

"Wow, that was awesome!" A cheerful little voice called over the fence.

I lowered my camera and regarded Jessie's bunny-rabbit smile. "You saw that, did ya?"

"I never saw a humming bird up close before." She admitted. (She said 'bird' like 'buud'. I have absolutely no idea why her mannerisms tickled me so much, but each time she spoke, it was like champagne bubbles tingling their way up my cheeks).

I approached the fence and angled my screen toward her, so she could get a glimpse of my shots. My camera has quite the zoom on it.

"Oh wow! Beautiful," she cooed. "How long have you been into photography?" She asked.

"Since before you were born, young lady."

"You have quite the eye for it. Did you always shoot birds?"

I allowed a sly grin. "Nude models," I winked.

She giggled. "I meant like sunsets and weddings, you dirty man!" She gave me a playful shove, not at all offended by my lewd insinuations. People seldom are. I'm very unassuming in appearance. Pleasant, playful, attractive, but at that age where people write me off as harmless. An all American retiree still holding onto his energy and looks.

"I may have dabbled in a bit of everything."

"I'd love to try it some time," she admitted.

I gave her a glance. It was late morning. Not a work day for her, but I was already aware of her husband's frequent travels, if not for any other reason than I'm nosy. "What have you got going on today?" I asked.

She shrugged. "Nothing," she admitted. "Michael is in Chicago until the end of the week. I went shopping yesterday, and have some clothes to return, but I'm not feeling like it today."

I felt a little bad for her. She said it with some degree of loneliness and disappointment. She wasn't at the age quite yet where her husband's absence would turn to resentment. But she was definitely a girl who struggled to entertain herself, wanting others to keep her busy.

As much of an unabashed manwhore as I am, I'm also not a complete douche-bag (sometimes). So I say with all honesty, that I had no intentions other than being neighborly. I smiled at her, and passed her the camera. "Well this should keep you busy for a while."

She lit up. "Really?" ("Weally?" There was that pleasant tingling on my cheeks again).

"Yes, really. Go have fun. Get it back to me whenever."

"I promise (pwomise) I won't break (bweak) it. I'll bring (bwing) it back tonight!"

"Keep it all week if you want. I'm not going anywhere." I waved dismissively.

Jessie thanked me again, and bounded back to her porch with her new prize. I took a moment to admire the way her legs looked in her cut-offs, and the way her breasts bounced beneath her tanktop. Great googily moogily! She could make a turtle-neck sweater seem low-cut. Her youthful energy did nothing but add an extra jiggle to that bounce. She definitely had the perk of a first-year cheerleader out to prove herself.

Ah, sweet youth.

I smiled to myself. My good deed done for the day, and the girl had some entertainment for the week, until hubby returned. I decided I'd earned a reward-- maybe a dip in the pool, and a nap in the sun.

***

It was a few hours later when my cute little bunny next door popped her head above my fence again.

My shirt was off. I had a healthy glow to my skin. Beads of sweat were softly tickling their way down my muscles.

"Hey Woy," she said. There was a touch of hesitancy to her voice that I picked up on immediately.

"Uh oh... you broke it already, huh?" I asked, ready to dismiss such a thing as not a big deal.

"No... umm..." she glanced away and a little blush crept over her cheeks. "Actually I wanted to ask you something kind of weird."

I sat up with a grin. "Oh, I'm always up for weird! What have you got?"

There was that timid hesitation again. She sank slightly down below the fence-line from embarrassment. Only her eyes poking above it. "Well I wanted to ask... and this is totally cool if you say no. I would understand!"

I twirled my fingers in the air, wearing an understanding smile. "C'mon, out with it, girl!" I urged her.

"Well... I was wondering if you'd help me take a few pictures... for Michael... you know... while he's away."

I had a rough idea where this was going, but at the risk of incriminating myself as a pervert with ideas on the brain, I wanted her to spell it out. "What kind of pictures?"

I could sense the blush she was wearing right now, even if she was hiding it behind the pickets of my fence. A loose strand of her brown hair had escaped her ponytail and she swept it behind her ear. "Well you said you used to photograph models, right? Well I thought--"

There it was. I smiled pleasantly. "You want to take some boudoir photos to send to your husband, to show him what he's missing while he's away," I finished her thought for her.

A laugh filled with nervous energy burst from her mouth. "Yes," she sagged, relieved to have gotten that off her chest. "He's traveling a lot, and I thought I'd surprise him with something to look at and entertain himself with."

I laughed to ease her tension more. I'm a pretty judgment-free guy, and I think she was picking up on that by my reaction. "If you're that shy about asking me, why don't you take them yourself? I can lend you a tripod." While I'm generally a sexual person, and while Jessie was especially attractive, you have to believe me that I really had no bad intentions with this young lady. She was a sweetheart whose chipper voice and perky pep always put me in a good mood. I wasn't about to go out of my way to corrupt her (not that I wouldn't mind-- I'm just a man, after all). So I thought it best to offer a solution that wouldn't tear down that wall between us.

"I tried a few, myself," she admitted. "But they just look like selfies. They make me feel trashy. If I'm going to objectify myself, I'm going to do it right, you know?" She laughed and I could see her sashay with a bit of sass to her posture. "I want to look like a professional pin-up girl. Not some Onlyfans webcam stripper."

"Onlyfans?" I feigned like I didn't know (of course I know what Onlyfans is! I'm not *that* old).

"Girls who take off their clothes on a camera on the internet."

I shrugged. "In my day we just called them 'Peep Shows'."

"Gross!" She declared, making a gagging sound. "So you'll do it?" She was nearly pleading now. How funny that she'd gone from barely able to speak her request, to excited and insistent.

"As long as you're comfortable with me doing this for you, I'll happily help you out."

She laughed. "I know you and you've never made me uncomfortable. If anything, I'd probably be more uncomfortable going to a real photographer."

"Are you saying I'm not a real photographer?" I teased, just relishing in toying with her.

"I didn't mean it like that," she blushed again, this time so I could see those rosy cheeks turn even rosier. "I just mean like... you give off this vibe like you've done this sort of thing a million times, and it's like nothing to you. So I trust that you're not some creep."

(Oh kiddo, you have no idea).

I smiled pleasantly. "Oh trust me, I notice beautiful women the same as I did when I was 17, as I do now at 60. That'll *never* change." I winked at her and was rewarded with a flattered blush. "But I'll go get all of my equipment and bring it over. Like you said-- if we're doing this, we're doing this right. And I'll give you direction or make suggestions, but we're not going to do anything that you're not comfortable doing."

Those blue eyes lit up once again. "This sounds fun! Think I could make a good model?" She flaunted her lashes at me.

"I think you'd make a fantastic model."

***

Jessie had certainly made a good call, coming to me. I definitely had all the professional goodies. I'd spent the better part of an hour turning her bedroom into a photography studio. I came with lighting, cameras, mounts, tripods, and mirrors.

"Oh wow!" She declared when she saw how I'd transformed her room. "D-do you want me to pay you for this?"

"Don't be silly," I waved. "It's not like either of us had any plans today, it's for a good cause, and who says this isn't its own payment?" I winked at her.

She laughed and smacked me playfully with the back of her hand. "You pervert. That's why you set everything up so quickly, huh? You're working just for nipple." With her flattered smile came a hint of something else... A flicker of naughty suggestiveness. I'll bet she was thinking she could give this old man a heart attack, and she was toying with that thought in her head.

"So why don't you show me what kind of outfits you have in mind, and we'll go from there?" I said, back to business now.

She rummaged thoughtfully for a few minutes, making her selections carefully. She seemed a little bit lost. She'd selected a few expensive and very pretty dresses, but unless she wanted to turn this into a fashion photo-shoot, she was missing the mark.

"One dress," I told her. "But we'll make some adjustments."

"I have a couple of bikinis," she suggested.

"You wanted boudoir?" I asked. "Let's steer clear of making this a swim suit catalogue. You want something that he doesn't see you in frequently, right?"

Suddenly something occurred to her. She slapped her forehead and went for her closet. She rummaged through a box in the back-- their 'sexy time' outfit box. Jessie produced a black and red lace corset, and a black sheer baby doll.

"Those will work," I nodded my head, looking over the contents of her closet. "Actually..." I said thoughtfully. "Does your husband have a preferred button-down for work? And a tie?"

She looked momentarily puzzled.

I smiled my knowing worldly smile. The smile of a professional who'd done this a thousand times. "Trust me."

She thought for a second and came out with a bright blue button down. "It's his favorite," she said. "He was wearing it when he proposed," again, stammering over her words cutely.

"Perfect," I held it beside her. "It matches your eyes." The tie was professional and clean-lined. Blue and white stripes.

"Well start with the dress and go from there," I told her. "Go change while I adjust the lighting."

***

We started small. I didn't want to overwhelm her right away.

Jessie seemed excited to display herself as the pampered princess, because when she emerged from the bathroom, she was lavished in an expensive little black party dress. Black with sequence, slit up to her waist, giving a fantastic side view of her leg and thigh. It was tasteful, but it was definitely hard to hide her breasts. The cut wasn't low, but it was low enough to show off the sheer size of her melons. Her cleavage seemed to go on for days, and although I was definitely looking, there was no sign of any tan lines.

She'd applied more makeup than usual, and her was in a bouncy ponytail. She looked like she was going to prom.

I took one glance at her, and shook my head in disapproval. Don't get me wrong, the dress fit her well-- snug in all the right areas. Her cleavage was immense-- it boggled my mind how such a cute bunny-faced girl could have the rack of a porn star-- and her dress displayed much of her leg.

"It doesn't look good?" She was slightly hurt and offended.

"You look like you're about to join your husband at a fancy dinner to impress his boss. If that's what you want, we can do that. But I thought the goal was to give your husband something to drool over. You want him craving you, remember? We need to give him something to masturbate to while he's out of town."

"That is the goal," she admitted, and looked at herself in the mirror.

"It'll make for a really nice picture," I said, "But if you want 'naughty', we'll have to spice things up a bit."

She shrugged, not having many ideas or imagination. "I guess I'm bad at this," she deflated.

Lucky for her, she had me to help. I'm an endless wealth of sin and debauchery. And I had an idea. I went to the bed and skewed the covers. I tossed the duvet to the floor, along with several pillows. I knocked over the bed-side lamp. I turned the bed-side wedding photos face down, and I left the backdrop looking like a party had happened right there on the bed.

Jessie looked taken aback. I smiled at her. "Modeling is like acting..." (Is it? I have no idea. I was just making this shit up as I went, and it sounded good.) "For this shoot, you won't be playing the part of the good wife going *to* the party. You're going to be the bad wife *after* the party. Understand?"

That seemed to make sense to her. "Ooh, I like it." There was a hint of naughty excitement to her expression as she processed this concept for the first time. Clearly it was new to her. She licked her lip thoughtfully, and gazed at the bed.

"Here..." I undid her ponytail and deliberately messed up her hair. I arranged her heels, one on the bed, one discarded on the floor within view. "Is there a pair of underwear that your husband is especially fond of?" I asked.

She retrieved a black lace thong, and was aghast when I suggested she toss it haphazardly somewhere within view. We ended up hanging it from the side of the headboard, like a trophy.

I arranged her on the bed. Her inexperience was showing, but she seemed to be easing into the concept. Under my direction, she slid a strap of her dress down her shoulder, until one of her nipples came dangerously close to revealing itself. She inched her dress high... a little reluctant to mess it at first. But when I got behind the camera and fabricated the back-story for her, she seemed to delight in the concept.

"So strike a pose and give me a look like... last night was your anniversary dinner. You were going to take your hubby home and have wild sex. But he blew you off to pull an all-nighter at the office, probably working with that skanky slut that you can't stand."

Jessie giggled. "He doesn't work with some skank that I can't stand."