Ch 5 - Reflections

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Allen and Jen go to dinner. Allen confesses...
3.3k words
4.62
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Part 4 of the 13 part series

Updated 08/08/2023
Created 07/16/2023
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Showered and toweled off, Allen rummaged through his own drawers and closet to put together an outfit with a mix of Jen's migrated clothes and his own. He found a pair of her panties in the back of his own underwear drawer and, clean or dirty, was about to slip them on when he found one of her skirts peeking out from the bottom of a pile of clean laundry, and decided on the spot that he was going to dinner commando, dammit, just because he felt an urge to be naughty.

He slipped the skirt on and adjusted it, then - bonus! - he came across that pair of stockings she'd worn last week and left at his place after a torrid night. They were a dark, smoky gray and subtly striped; a thick seam ran up the back of them He was surprised how easily they slipped on and settled into place.

He found one of her casual but sexy bras and committed himself to stuffing his boobs into it to maximize his cleavage. It took some work, but he'd seen her dress countless times and after a couple tries, he had the boob holster applied mostly correctly. After some tugging and shifting, he had his new rack nicely displayed.

Over the top he threw a striped Oxford from his own wardrobe, with the top three buttons undone to show off his cleavage.

Shoes presented a problem. He examined and rejected a pair of "fuck me" pumps that Jen had cast off in his room a couple weeks ago. He settled for a pair of low canvas espadrilles that didn't quite work with the outfit but wouldn't kill him when he tried to walk in them.

Done, he checked himself in the mirror. Not bad! He quickly laid out some trousers, a tee shirt, cardigan, and underwear to save Jen the trouble of finding things to wear, and went to the kitchen to get another glass of juice. Even after sucking down half a pitcher of lemonade, he was still fucking parched!

Some minutes later, Jen joined him in the kitchen, dressed mostly in what he'd laid out. She'd added one of her own scarves as a foulard that made her look like a fop, but Allen raised no objection. It was actually kind of cute. Her hands clasped behind her back, Jen swiveled left and right on her hips, showing her outfit off as she eyed him from head to toe.

"Fuck! You look hot, Baby," she purred. Then her eyes fell on his feet and she 'tsk'd sadly. "I was afraid you'd have a problem there. Here, put these on," she said, pulling the "fuck-me" heels out from behind her back.

"I'll fucking fall to my fucking death from those," Allen protested.

She closed the gap between them and bent over slightly to kiss him. "Shh," she soothed, "do it for me, Baby! You'll look so fucking hot in these! I'll help you. Here!" She got down on one knee and pulled one foot up, removing the frumpy canvas footgear and slipping on the dark, shiny leather high heel.

It did feel sexy against his foot. He just didn't know...

She set his foot down carefully. "Now: Use the counter. Get up on that foot and balance."

He did. It didn't seem too unsafe but he was just standing, not trying to walk yet.

Jen took his other foot and swapped shoes, then returned it to the floor. "There. Now just keep yourself centered and stand up!"

Allen pushed off the counter and tottered a moment, then found his balance atop the surprisingly sexy-feeling but still strange and uncomfortable footwear.

"Now walk to me, one foot in front of the other, just like this..." She pivoted and took six measures steps away from him, demonstrating. Allen followed her example, wobbling only once. Apparently, Jen's body was well conditioned to walking in heels. Jen motioned for him to turn around and walk back. He did, successfully.

"See? Easy," she remarked, moving to join him at the kitchen island. "Now," she said, placing one hand on the counter either side of his waist and leaning in to nuzzle her lips against his earlobe, "you look hot as fuck! ...and - fuck! The fucking hormones!...and fuck-knows what other shit you've left me to deal with here! For some reason, I'd like nothing better right now than to bend your hot ass over this counter and fuck the living shit out of you! But we're not going to do that. Not yet. Not now.

Now, I'm gonna take you out to a nice, safe, public place where we can't just smash our naked parts together at every whim, and we're gonna have a nice meal, and a nice chat about just what the ever-loving fuck is going on here! Ok?"

"Ok," he demurs. Then, being just a bit catty, "should I go first so you can see how fucking hot these heels make my gorgeous ass look..."

A beat while she stares into his eyes, then, "Yes! Fuck! Go show that hot ass off you fucking tramp!" Allen sashays out of the kitchen on his 'new' heels without looking back.


She drives them to their favorite spot; a little bistro on the north side with a simple but elegant menu, a well-stocked bar and a deep wine cellar. She orders a double martini, dirty. He orders a Campari spritz. When the drinks arrive, they trade glasses and gulp them down before trading back the empties. They place their meal orders and get refills on their drinks on top of ordering a choice favorite wine to compliment both of their meals. They're Uber-ing home at this point, but to this point they've kept everything normal.

Their orders in, Jen slumps in her chair and flips a hand across the table. Allen takes it tenderly. Tears glisten in her eyes. "Allen? What the fuck!?"

I don't know, Baby! I don't. Maybe... just... We're okay," he says.

"Okay!? Allen! I have a cock! And it's yours! And it's driving me fucking crazy horny!" Her outburst draws attention from the wait staff who subtly alter their trajectories around the house.

"Is this...," she starts. "How long... What if..."

"Jen! Jen! It's okay!"

"Maybe you should start calling me 'Allen' in public, yeah?"

"Honey," he concedes, trying to placate, "Look. We're... This is some pretty fucking weird, fucked-up shit, yeah. But we're in this together, right!?"

"Yeah," she sniffles and smiles at him, "Yeah! We are!"

"Okay, then. Let's count that a win. We've... today has been... well, I for one..." Allen senses he's not getting where he wants to be. She grips his hand and it centers him. He starts again. "Up side," he offers, "I've had some very enlightening insights today that I think have helped me... helped us... grow and become closer, yeah?"

"Allen. I fucked your brains out with your own cock," she says, deadpan. "How... oh. Ok. Yeah, maybe." He gives here time to work out whatever's racing through her mind. Whatever it is slowly slides from her face and she looks at him with new-found resolve. "Ok: Together. As long as that's true I promise not to panic anymore, okay?"

"Okay," he smiles. Their second order of drinks arrive and they sip more measuredly this time.

"So," Allen begins, setting his martini down carefully, "let's assume that this may or may not be a permanent thing, but for right now it's our new reality, with me?"

She nods.

"Okay. Positives?"

"We're in this together," she smiles at him.

"Damned right," he agrees. "What else?"

"Well..." she hesitates.

"Go on," he coaches.

She grins sheepishly at him. "I kinda did always wonder what it would feel like to have a cock, I guess..."

"Okay. So. Good..."

"And you," she asks with an expectant burst of empathy, "I can't imagine... how are you... what's it been like for you... Pussies are so fucking complicated. Thank goodness I just got done my period. Hey... that's another plus, maybe! This shit goes on long enough, you'll get to have some real empathy for what that fucking shit is like."

Allen rolled his eyes and groans.

"Okay, so how's it going so far for you," she redirects.

"Well," he allows, "if you hadn't texted when you did, I'd still be playing with these!" He cups her - his hot rack for emphasis, "and diddling myself with the water jets in the shower!"

She giggles. "Damn! You're a fast learner! Took me almost sixteen years to figure that one out, you horny cockslut!"

They both chuckle. Then Allen adds, "Horny is a mild fucking word for it. Seriously, Jen. Are you... You know how my - your cock won't stay down? This huhu is the same. I'm wet constantly. And I can't stop thinking about cock! Was it like this when you had it?"

"Hmm," Jen thinks. A little maybe? Maybe you're just getting used to it. Maybe we both are and it's just so intense because it's new. Like a second puberty or something."

"I was never this constantly horny when I was a teenager. And I was a fucking guy then!"

"Speaking of which, I'm curious," she starts.

"Yes?"

"Well, how did it... how did you... was it weird you know..." she points at her crotch, hidden below the rim of the table.

"What? Sucking my own cock," he blurts, "fuck! I've wanted to do that since I was thirteen!"

They both share another near-hysterical chuckle.

"Seriously, though," he continues, "It just felt.... I don't know. Natural? Right? ... Naughty! Oddly, it wasn't as weird as... well, kissing a guy for the first time. That was a bit odd there for a sec but we got over it. Sucking your cock, though? It felt naughty as fuck and I fucking loved it! ...and you kinda got a kick out of it to, yeah?"

Jen blushed deeply and Allen began to feel his pussy moistening with all the talk about cock.

"Allen, Sweetie," she beamed at him, "Nobody has ever sucked my cock like that! It was fucking amazing and I want you to do it again! Right here! Right fucking now! In the middle of the bistro with everyone watching your hot, talented cockmouth working my throbbing rod...!" She held it a beat. "Seriously! That's what I ... or what I feel your body wanting. Fuck! It's what I want and it's so..." she trailed off.

"New... exciting... exhilarating... scary...," he offers.

"Yes! All of that!"

They hold each other's understanding gaze a moment.

"I found your dildo," Allen blurts out.

"You didn't!"

"I did!"

"The purple one!? In my nightstand!?"

He nods, and continues, misreading the mild horror creeping across her face, "I got up, had a good sit-down pee, freaked out in the mirror, then I just felt his overwhelming craving for cock! I just had to fill my - your - my hot pussy up with cock! It was like this ... I don't know! Some overpowering imperative!"

"No!" Jen shakes her head slowly. "Allen. I mean you didn't find my vibrator!" Jen sighs. "Susan's mom was visiting last weekend. She asked me to hold onto it for her."

"Huh," Allen mused. "So... um, how do you feel about that?"

"Well, huh," Jen said thoughtfully. "Yesterday I'd probably have said eww! But I suppose my perspective's kinda changed on that. I'm more worried what Susan would think."

"Oh, I'm sure she's probably cool with that," Allen offered.

"What do you mean?" Jen eyed him curiously.

They were interrupted by a contralto voice calling across the room, "Hey, Jen!" They both turned to see Jen's friend Hellen making her way across the dining room. Her perfectly coiffed auburn red hair bounced on her shoulders. "Hey, girl! Hey Allen." Helen bent over Allen to give him a hug and a peck on each cheek - and an eyeful of cleavage that hung deliciously inside her thin silk blouse. She smelled yummy! Allen felt a warm fuzzy burst of cheer his pussy.

"I don't want to bother you guys. It's just been so long! I saw you and just had to come over and say hi and twist your arms in person!" As she said this she'd stood up and leaned to grip Jen's upper arm in her expensively manicures fingers. "We're opening up the patio this weekend. You two have to come over for cocktails and lunch on Sunday, alright?"

"We..." Allen saw Jen catch his eye and give her head the slightest of shakes, while Helen's fingers lingered on her arm.

"Of course, we'd love to! Can I text you," Allen offered.

"You can, but I just won't take no for an answer, you two. Okay? Enjoy your meal and have a lovely evening now." She winked and turned away, her fingertips brushing along Jen's arm as she did. Both watched Hellen's gorgeous butt roll away underneath her tight skirt, her leather pumps clicking on the tile. She didn't show any panty evident panty lines.

"What's up," Allen asked after Hellen was out of earshot.

"Hellen's...let's say 'complicated', Allen," Jen said. "Sean, too. I'm pretty sure they've... got a very actively open relationship. And Hellen's got the hots for you. Did you see her flirting with me!?"

"Yeah. I kinda caught that. Must be my new intuition," Allen quipped. "Well, I did leave it so we can make our excuses if we have to."

"You don't know Hellen," she sighed, "and that's the other problem. You don't know Hellen. There's almost no way that doesn't end up awkward and uncomfortable at one point or another."

"Oh. Yeah. Guess you're right," Allen allowed, then swore, "Fuck! Your bladder! I gotta p... powder my nose," Allen quickly slipped out of his heels, not trusting himself to stay atop them in a hurry. He grinned at Jen and squeezed her as he stood to go find the loo.

"Ladies is on the left," Jen smirked at him as he hurried off.

Despite Jen's warning, Allen's momentum and habit very nearly carried him into the men's room. Only the sight of a guy coming out reminded him to veer left ...into uncharted territory.

No urinals of course. Huge sink counter but only two stalls, only the handicapped one empty.

Allen had no compunctions about taking the option that kept him from peeing down his stockings. He hiked up his skirt, sat down heavily and let go with a throaty grunt.

"Aaaaughhh!"

"You okay in there," came the alarmingly familiar voice from the other stall.

"Yeah, thanks! Just had to go so fucking bad, you know?" Allen said apologetically.

"Jen?"

"Helen?"

"Hey, Sweetie!"

Fuck! Allen thought, just take it easy. Pee casually.

His pee splashed loud and long in the bowl. It was still gushing out of him when he heard Helen flush and remark over the hydraulics, "Damn, girl! You really did have to go! Do I need to give you a checkup?"

What!?, Allen thought, is she a urologist or is that code for something I'm gonna fuck all the heck up now? He went for simple and to the point. "I just... got distracted and then really had to peel all of a sudden!"

The last dribbles of pee squirted out of him and he wiped carefully, suddenly thinking of UTIs thanks to Hellen. His skirt fell back in place as he stood and adjusted his thigh-high stockings through the fabric.

He heard a sink still running and hesitated. How long should he take getting out of the stall? He wiped again and heard the water shut off and the hand towel machine cycle. When he heard the door creak, he flushed, took a deep breath, and opened the door.

Hellen was waiting for him with an indecipherable grin. He put on what he hoped was a neutral smile and moved to the sink to wash up. Was there some ritual he should know? You're overthinking this, he thought, girls wash their hands just like everybody else!"

"You two out on a date night," Helen inquired, somehow managing to put a lurid emphasis on the word 'date'.

"We're just out for dinner," Allen offered neutrally.

"Oh, come on, Honey! Are you gonna get laid tonight or what?" Helen cast her a naughty grin.

"That's always my hope," he allowed, truthfully, taking a length of paper towel and drying his hands.

"You sly dog, Chuck," Hellen grinned cryptically.

Allen took a moment to check himself in the mirror, then stood back, hoping it would signal Hellen that he was ready to leave. No such luck: Hellen stood resolutely in his path; eyes locked on his. She stepped into his personal space and he resisted the urge to back away, unsure what ladies' bathroom protocol or Jen's history with Hellen dictated was appropriate here. Hellen slid one hand up Allen's arm to rest on his shoulder and cupped his cheek with the other.

"I'm really serious about Sunday, Love! You and Allen simply must come! Okay?"

"Sure, Helen, of course," Allen stammered.

Helen searched his eyes for a moment, then smiled. "Good!" She leaned in and put her mouth sensuously close to his ear and purred, "I promise you won't be disappointed!"

Hellen stepped back, her fingertips trailing away feather light from Allen's face and shoulder.

"See you then, then," she grinned then added mischievously, "I hope that hot stud of yours fucks your brains out tonight!" Hellen puckered an air kiss at him, winking, then turned and led their way out of the bathroom.

With one more pat on his shoulder blade and a naughty wink, Hellen said, "See you Sunday," then left Allen to find his way back to the table.

Having seen the last of the exchange, Jen asked him nervously as he sat down, "What was that all about?"

"She... Hellen was just reiterating her invitation for Sunday," he reported.

"What happened? What did she say? What did you say," Jen grilled him.

Allen briefly described the encounter, then answered a few pointed follow-up questions, the last of which was, "Did she touch you? Did she kiss you?"

"Yes. No." Allen gave her the details as he remembered them.

Jen sat for a minute, thinking. "Damn," she said.

"What?"

"Later. We can deal with that later," Jen dismissed the topic as swiftly as she'd made it the focus of their conversation. "You said you didn't think Susan would mind that you'd... to think that I'd jilled off all over her vibrator. Why?"

Fuck. "It vibrates!?" He was extemporizing. Think! No! Keep it simple! "I just didn't know how girl roommates - I mean, it didn't seem like a big deal," he said.

"Have you ever shared a fleshlight with a roommate? A cum rag?"

Allen saw the flaw. "No," he said, biting his tongue to keep from adding an 'of course not'. "But I just thought..." Fuck! Think "She's into girls, right?"

"Yeah, she is," Jen said, "but she's not into me!"

Allen's awkward silence only fueled Jen's anxiety and it made her jump dangerously towards exactly the right conclusion.

"Allen?"

"Huh?"

"What happened?!"

"Susan was home, you see and..."

"What? Happened!?"

"When you woke up - you remember that flood of strange hormones and things you couldn't control, right?"

"What. Happened?"

"You said 'guys, gals, fruit salad,' right!? Everything made you hard and horny, right?"

"What. Fucking. HAPPENED," Jen seethed.

He told her.

She sat dumbstruck while he kept babbling it all out - the whole story - like he was back in high school and recounting his first sexual experience to an enraptured brace of friends. His narrative petered out and she was still sitting there unmoving.

Dinner arrived.

Allen tucked in, suddenly ravenous, and Jen did, too. Neither spoke another word until the empty plates were cleared, and the dessert menus offered.

"Cheesecake. Two. One with caramel. Two cognacs. Double," Jen reeled off at the accommodating waitress.

Jen didn't trust herself to talk until after desert arrived. After she'd cleaned her plate and tossed back the last of her digestif, she sighed deeply, then muttered, "Oh! We are so going to Helen's on Sunday!"

"What," Allen asked, not sure he'd heard her.

"Nothing," she spat. I'll get the check. You call an Uber."

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Cunning_Linguist_69Cunning_Linguist_699 months agoAuthor

Next chapter is in draft/exit. For some reason the series (beta) shows a link already where there is no chapter yet

AnonymousAnonymous9 months ago

Where is next part?!

Cunning_Linguist_69Cunning_Linguist_699 months agoAuthor

Much more to cum!

AnonymousAnonymous9 months ago

Enjoying this one a lot. 😊 Chapter 6 link is broken.

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Ch 4 - Reckoning Previous Part
Being Jen Series Info

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