j-j-j-w Jackson Wimbish

David's girlfriend, Allice has a couple of days off and invites him for a night out. What she has planned may be mundane, but with a memorable twist. This is the whole night as it happened with very few details left out.


Érotique Interdit aux moins de 21 ans. © J.J.J.W

#romance #sliceoflife #date #sidestory #32828
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The Real Date Night

Lunchtime arrives and I find a nice bench to sit on outside by the track where some runners are passing by.

"And now, I wait," I say to myself, unpacking the lunchboxes I brought. Both were cold turkey and wasabi sandwiches, with a few cookies and a soda. Sitting back, I look at the sky and lose myself in the blue.

"Hey David, been waiting long?" A voice snaps me out of my trance. Allice was standing next to me and I hadn't noticed.

"No. I think I just got here," I say as I hand her a lunchbox and she sits next to me.

"I got a day off tomorrow. Do you have any plans?" She opens her lunchbox and begins eating. "Ooo, wasabi."

"Only a day?" I ask, taking a bite.

"This week's been pretty crazy. No one ever said being a pop star was easy."

"Yeah but, only a day?"

"Are you doing anything or not?"

"I was going to get a haircut-"

"No, it's so long now- don't cut it." She wraps an arm around my neck and strokes my hair with both hands.

"Why not? I only let it get so long because of that human evolution assignment a while back."

"But you look so cute and adorable and I love you!"

"What was that?"

"I said you look so cute and adorable! How about this? If you get a haircut; I'll get one too, and we can look all manly together." She puffs up and flexes almost comically, and despite her muscular physique, she still looks as dainty as a fairy.

"Manly?" I laugh at the notion until I notice how serious she is. "Ok, I'll keep it long. Gotta keep that 'Allice in Wonderland' aesthetic. After all, it's not Adam in wonderland."

"Ooh, thank you- thank you- thank you!" she begins ruffling through my hair at increased speeds.

"The more you do that, the longer it's going to take me to comb it out later."

"Don't worry, I'll help." She slows down a bit but keeps going.

"So, what do you plan on us doing tomorrow?"

"I was thinking we could go to a cafe and eat some sweets. Then we can go shopping and we can try on some dresses."

"What do you mean 'we try on dresses'?"

"Come on. You'll look so cute in a dress."

"Nope."

"I'll be in a dress too."

"You're always in a dress."

"Yeah, but afterward, we can go to the movies-"

"Movies, yes; dress, no."

“Then after the movies we can...” she looks around suspiciously and then whispers into my ear, “Nobody’s going to be home, so we can fuck until the sun rises.” She turns a bit red.

After hearing what she had to say, I couldn’t help turning red myself. “Alright, I’ll try anything once, but nothing crazy after that, alright?”

"I promise," She says with the smuggest smile I'd ever seen on her.

"But what if somebody we know sees us? All the other guys'll start looking at me differently" I sip my soda; half done with my sandwich.

"I know somewhere nobody from our school goes." She winks. "Nobody needs to know."

"I can't change your mind on this, can I?" She's already shaking her head before I finish my sentence.

"You already said you'll do it." She gives me a peck on the cheek. "For a day, my boyfriend will be my girlfriend."

"I'll do it, but I'm not going to like it." I take another bite and nearly choke on it.

Allice pats my back and says, seductively, "You'll love it"

-afternoon the next day-

"Three, two, one, open your eyes!"

I open them and what I see before me is a slender figure hidden shyly behind a blue flowery loose blue and red dress, ear-length brown hair tied loosely with a pink butterfly hair clip and waving down in the front just over a pair of sparkly wide brown eyes, and blue flat shoes open at the top.

I blink and look to my right. Allice is standing there dressed similarly except her blonde hair is draped across her shoulders and she's in a green Chinese-style dress and matching heels.

"So? like it?" She says, smiling affectionately.

"I... I don't even know what to say..." I looked back at the mirror. "That's not me."

"You're right. That's Diana. 'David' is staying here. I'm taking Diana on a date. How does that sound?" She takes my hand and puts it to her lips.

"I already agreed, so... I guess I can't complain..."

"That's the spirit." She leads me by the hand to the door of her room. "Now, you remember what I taught you, right?" I scowl and she pinches my face with her fingers in response.

"Yes ma'am," I say, realizing how serious she is about our date.

"Good, now as long as you conduct yourself like a nice little lady, we can enjoy ourselves both now..." She lets her hand trail down from my face to my waist. "And later..."

We walk for a solid thirty minutes and all I can do was look around nervously.

"Don't worry, we're almost there." Allice seems to find joy in my suffering.

"Why did we have to walk all the way there?" I ask in a whisper.

"Obviously it's so I can show you off. I mean, look at you. I'd go gay for you."

"That's not the point," I whisper urgently, trying not to raise my voice.

"How're you two young ladies doing this evening?" A guy appears out of nowhere. He's dressed for a night out in a casual suit. I'm too scared to look at his face in case he's someone who knows me.

"We're doing fine, thank you," says Allice with a smile.

"Going somewhere special?" He keeps pace with us.

"We're on a date." She grabs my hands in hers.

"In that case, can I offer you two a coupon for-"

"I'm sorry, we must hurry along." She pulls me suddenly and I stumble behind her for half a block.

"Do we know that guy?" I ask, still whispering.

"No, but he might know us. He's a big-shot photographer with a magazine company. To think we'd run into someone like that here." She sighs. "If we run into him again, he won't leave us alone until he gets a picture."

"Well, what do we do?"

"You'll have to take the lead next time."

"But he'll hear my voice."

"We'll take care of that problem in time. For now, just be the quiet little princess you are."

Reluctantly, I nod my head and keep quiet.

An hour and a half later, we arrive at a mall on the other side of town. The sun just started setting and the glass building reflects the amber haze of the sky perfectly. We enter and make a B-line for the clothes store.

Allice immediately begins picking out dresses left and right. I open my mouth many times to object to the ones she chooses for me, but close it immediately as we're always in close proximity to someone else.

After maybe ten minutes of picking out clothes, she practically forces me into the changing room and won't let me go until I try on at least eight different dresses. They were wildly different in design and materials.

The tight space and awkward nudity triggers a response in me that I'm not expecting. Allice, on the other hand, was all too prepared for it. Since I was fully cross-dressed, I was wearing panties and my bulge was all too easy to notice. Before I know it, one of her hands is nestled neatly under my scrotum while the other is stroking my shaft through the panties.

I, too weary of my voice, only take a sharp breath while she frees my manhood from its confines.

Allice, with a mischievous smile, says, “I don’t think this one fits, let’s try this one,” with a finger over her lips and my tip just as close.

She kisses the head and slowly introduces it to her tongue as she expertly pokes and prods it before attempting to swallow it in one go. My knees give out almost immediately and she wraps her arms around me to keep me balanced. She starts out slowly and increases in pace until I’m close. I tap her head as a warning and she stops completely.

“Ok, now this one.” She reaches for another dress for me to try on and never lets me finish.

As she does whatever she wants, I endure it all silently. Once we’re done, she makes me wait for my erection to subside before we leave the booth. Needless to say, it takes a while.

Allice buys three of the eight dresses she made me try on while I stand by silently.

"Done being quiet?" she asks, handing me a bag of dresses.

I look away from her and at the floor. I felt used.

"Oh, don't be like that." She leans in close to my ear. "I have a way we can fix that." She backs off. "Although, you are pretty cute being all mute like that."

I start walking straight toward the cinema on the other side of the mall.

"No, wait. I was just having my fun, come back." She catches up with me. "Look, you can't stay mad at me, right."

I look at her and look away with a huff.

"Okay." She grabbed my wrist and stopped walking, causing me to stop as well. "Alright, look up and try to sound as feminine as possible, I'll take care of the rest."

I look at her questioningly then do what she says. What escapes my throat is the highest voice I can make in imitation of my mom's voice, the only feminine voice I can copy.

Quickly, Allice raises her hand and flicks my throat hard.

"Ow," I say, gripping my throat. "Whoa," I say, noticing that my voice stayed high on its own. "How did you?"

"Every girl knows that it's all in the wrist." She flicks her finger in the air a few times and winks.

"Sure," I say.

The walk to the cinema is short and uneventful, but once we get there, we have a choice to make. Despite how meticulously this date was planned, neither of us thought of what movie to watch.

"What do you wanna watch?" Allice was looking between the posters displayed at the cinema entrance with a big smile on her face.

"I thought you already picked one out."

"Nope. I thought I'd leave this one up to you."

I let my eyes trail between the images hanging on the walls. "I don't know. I'm fine with anything as long as it's fun."

"Fun, huh?" Taking one last look, the girl still holding my arm nearly drags me into the theater with one hand. "I know what we're watching."

Before I have a chance to ask, she already paid for the tickets and started buying snacks.

"Wait, what are we watching?"

"You'll see. What kind of snacks do you want? They have sour gummy worms."

"Oh, they do?"

"How many do you think you could eat?"

"You don't want to know that answer."

"Well, now I gotta know."

We ended up with four family-sized bags of sour gummy worms, an extra-large bucket of popcorn to share, and two large sodas.

We sit near the back of the theater and the film starts nearly ten minutes later. It turns out it's a supernatural horror movie about a home that's visited by a different monster every week while the family has to figure out how to survive each creature. As long as one family member survives when the monsters show up, they all come back to life with no memory of what happened.

Halfway through the movie, Allice stands to go to the bathroom and pulls me along with her. Once we reach the empty bathroom, It becomes obvious that she didn’t come to do a number. We enter a stall and lock it.

She pulls me close and says ”Return the favor from earlier.” She backs against the wall and pulls the front of her dress up while pulling her panties down. She then makes a V with her fingers and sticks her tongue through it.

I nod and get an idea. I would return the favor.

Moving my face to the space between her legs, I start by caressing her clit with the tip of my tongue and then replacing it with my thumb as I rub it while tracing a straight line between her lips, slithering like a snake. She begins to moan and I bring my face back up to suck her clit while I slip a finger inside of her.

Based on the moisture, she’s been wet for a while. Probably since she blew me in the clothes store. Knowing that makes me smile.

I insert another finger and hook them upwards, reaching for a rough patch within her walls. When I find it, she shivers. I stroke it while making sure not to neglect her clit all the same. After a couple of minutes, she begins to spasm.

“Oops,” I say, removing my fingers and backing away from her.

“Oh, you cheeky bitch, how did you know?” She seemed surprised and embarrassed.

“I can’t give away that secret.” I smiled.

“I have half a mind to rape you.”

“Don’t threaten me with a good time,” I say, cheekily. “Should I continue?”

“You’d better.” She grips the sides of my head and doesn’t let go until I start again. Each time she comes close, I pull away despite how hard she holds onto me. Eventually, she gives up and we return to the movie, but we already missed most of it.

After the movie, we head back. Almost every store we pass is closed. We walk and talk without a care in the world.

"Excuse me, ladies." A vaguely familiar voice sounded in front of us.

I yelp in surprise as I realize it was the guy from earlier. He wears an innocent look while his eyes wander a little too far below our faces.

"Uh, I, um, um uh...." I remember that I'm supposed to take charge in case we ran into him again and panic.

"No need to be so shy." He reaches into his suit pocket and produces a small camera. "I just want to interest you in a photoshoot." He smiles. "I'm a photographer and I've been having a hard time finding models. I was just wondering if you lovely ladies would like to have your picture taken."

"Um, I'm, I'm, I'm..." I can't explain it, but I'm suddenly overrun with emotion. "I'm sorry, I can't do it..." I begin bawling on Allice's shoulder.

"Are- are you okay?" asks the man.

"Look what you've done! Of course, she's not okay!" I've never heard Allice sound so furious in my life.

"Oh, I'm sorry, I didn't mean-"

"Step off!" She stamps her foot and scares the man away. She coddles me as we continue walking.

"I'm sorry. I don't know what came over me." I can barely look her in the eye while talking.

"It's fine, don't worry about it." She has an arm around me with a tight grasp. "I'm the one who put you in that situation, so I'll make it up to you."

"O-ok." It isn't hard to imagine what she meant.

Once we get to her house, we go straight to her room.

“You ready to end the night with a bang?” She pulls me in for a kiss that lasts long enough for me to run out of breath and serves to dull my sense of awareness.

I drop the bags I’m holding and embraced her. We almost fall on the floor, but land on the bed instead. We begin feeling all over each other and gripping anything we can. Eventually, we end up in a compromised position. I’m leaning over her and her legs are around me. My boner is pressed tightly against her entrance as if that was the only thing to do. I reach down and begin pulling the dress I’m wearing up over my head.

“Keep it on,” says Allice, “I want you to fuck me like a lady.”

I oblige with a gulp. Pushing both of our panties aside, it’s easy to see how turned on we both are. Neither of us was able to finish throughout the night and now is the time to let it all out.

“What are you waiting for? Should I take the lead?” She teases.

In one swift motion, I enter her and almost cum immediately. I grit my teeth and concentrate. She convulses just a bit and we both start gasping for air as if we had already been going for a while. I tried to pull out and she began convulsing again. The pressure of her squeezing brought me to orgasm early and she did too. It’s so intense it hurts, but despite this, I’m still rock-hard inside her.

“That was worth the wait,” she says, still spasming. “Let’s see how long we can keep this up.”

“Gotta be honest, that hurt.” I rubbed the back of my neck with my hand.

“Me too.” She grabbed my shoulders and forced me to switch positions with her. “But we have all night.”

I swallowed hard as she began moving. Every motion she made was intense and deliberate. She’d slow down whenever it seemed like either of us would go over the edge and speed up immediately after, not skipping a beat. At some point, I found myself pushing her up from below at rapid speeds with my hands on her hips.

“No-” She gasps, gripping my wrists.

I roll over so that we’re both on the bed and continue pumping away. She kisses me and I cum. She does as well soon after but continues riding it out.

I go flaccid and after a break of just cuddling, we get back to it. Before we know it, the sun is shining between our bated breaths and harsh voices.

“It’s morning,” I say, first to notice.

“Now’s a good time to stop.” My partner attempts to sit up, but falls backward and begins snoring softly.

“Maybe it is...” Before I know it, my head is on her chest and my vision is fading. “I love you.”

1 Octobre 2022 00:00:14 0 Rapport Incorporer Suivre l’histoire
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Jackson Wimbish I like to write what I want. Chances are, you might like it, too.

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