The Negotiation

The restaurant was busy and filled with the constant din of so many relatives talking at once, but a little nudge was all it took to draw my attention to Julia leaning slightly forward beside me. Meeting my eyes she looked down at the space between our seats and I followed her gaze to the hem of the skirt that hung off the back of the chair. Pulling her hand from under her skirt I immediately saw the milky pool of cum she was cradling that I deposited deep in her ass not 30 minutes prior. Sidling up to me as if to whisper something in my ear she discreetly brought my sloppy gift up to her mouth, lapped up and swallowed it in one smooth motion. The sound of her lips smacking right next to my ear shot a lightning bolt right through my core. She sat back upright, arched her eyebrows knowingly and gave me a smile and a shrug that I knew to mean, "Deeper next time." Dick straining against denim, I realized I'd been holding my breath and so when she turned and rejoined the conversation to her left, I exhaled, and the world started to spin. Only my mother's question pulled me out of the clouds.

"So, when are you two going to settle down and make me a grandma?"

I had already forgotten the deal we made the hour before we met my extended Italian-American family for brunch downtown. Julia was standing naked in front of the hotel bathroom mirror getting herself ready; applying the little amount of makeup she thought she needed to fully pass as the biological woman my mother thought her to be. A 5'6" brunette with her hair done up in braids she was freshly showered and shaved; smooth and sleek and intently focussed on creating the appropriate amount of liner to shape her eyes. Sliding out of the shower and directly behind her I placed the engorged head of my cock right between her smooth cheeks, trying my best not to jolt her while the eyeliner was in use.

"You know we don't have time enough for that" she muttered, staring me down in the mirror while simultaneously arching her ass the 15 degrees it took to place my tip right at the top of the hot entrance to her 'pussy.'

Round 1

This is how negotiations began, silently and without breaking eye contact: With firm pressure I rotated my hips, lining up my dick so half of my head slipped into her with a watery slurp, while gently pinching the nipples of Julia's natural B-cup tits. In response, she inhaled sharply and started to clench her asshole slowly, pushing me out of her entrance and leaving my tip mashed against the tight, wrinkled skin of her pursed hole.

She opened, "If we do this, we're going to be late for brunch and everyone will definitely know we've just been fucking when we walk in late, red-faced and sweating."

"Naw, this one's just a quickie. You've already cleaned yourself and I'm already hard. You'll have plenty of time to finish your makeup and we'll be seated before the mimosas get poured." I countered.

Still staring in the mirror without wavering she released the clench ever so slightly and my tip inched forward.

"Easy for you to say. When you get in me you're immediately gonna want to cum but I don't think you can hold out long enough for me to cum too. I'm gonna have blue balls AND have to deal with your gross uncle staring at my tits all morning? No thank you."

Dropping one hand from her nipple down her stomach, through the small dark island of pubic hair, I cupped her tiny balls and resumed a soft pinch on her waking boy-clit. The accompanying shiver she let out wiggled the majority of my tip into her.

Confidently I stated, "IF you don't cum, and I plan to make you cum, I will ride shotgun and blow you on the drive until you do. Even if that means I have to finish you in the parking lot of the restaurant."

Her eyes widened just a touch and we both knew I was winning the battle so she hardened her gaze once more. Seemingly locked and frozen together while we played this out a problem was growing and before she put it to words the tingly feeling in my mouth and cheeks started to find a solution.

"It doesn't matter anyway," she said dismissively, "YOU packed the bags for this weekend and YOU forgot to pack lube and there's just no way you're getting in here... without..."

Before she could finish the sentence, she could see the spit pouring out of my mouth and felt it splash at the top of her asscrack. Resolute and calm and still staring her down I continued to let it pour from my mouth and increased the pinch on her nipple and clit slightly. The gasp she let out forced her guard down and she stopped clenching her asshole momentarily, while also being the first to break eye contact as she looked down at her swelling clit. Instead of applying more pressure and worming my way deeper into her open hole, I waited a second while the spit pooled on top of my dick and instead pulled the tip out. The vacancy allowed the pooled spit to flood into her opening. Reapplying pressure with my now-slick cockhead, I let the current take my dick right into her ass-pussy, stopping halfway buried in one clean stroke.

The moan she let out was exquisite and caused her to straighten up and lift her head back up with an open-mouthed expression of shock and pleasure. The whole move, from spit to in-stroke, lasted 5 seconds at most so when she looked up spit was still dribbling out of my mouth, and she was made to understand that an unbroken string of spit was currently connected from my mouth, down her ass and my dick, right into the deepest part of her. Whatever remaining defense she had was now gone and the realization caused a thick drop of pre-cum to bubble out of her clit. I scooped the glistening white bead off her nub with my finger and brought it up to her mouth. She placed it on her tongue and sucked off her sweet and salty prize with a half-hearted eyeroll.

Round 2

This first round was over: We were gonna fuck before meeting up with my family, that much was certain, but there were many things left to negotiate before this was settled.

I was now halfway inside my gorgeous trans girlfriend and while not a long man (8 inches on my best day) I am reasonably girthy with a pointy cockhead that tapers quickly to a shaft that's two-thirds of a Coke can in width. She'd taken me inside her so many times that I knew she was still comfortable, but I gave her a moment to allow her hole to adjust to my manhood so we could resume negotiations. I dropped my hands from her nipple and mouth and placed them on the counter, taking care not to thrust any further within her while we composed ourselves.

Julia caught her breath and straightened her back, so she could resume the stare again in the mirror.

"Ok fine, so we're doing this, but you're gonna need to let me finish my eyeliner before we discuss further." she asserted, bringing the liner pencil I didn't see she'd grasped the whole time back to her eye. I'd had her girlcock inside my ass a few times so I was always so utterly amazed at what she could do with precision while a dick was buried in her so while she finished her eye makeup I brought my hands up to her hips and held her still. Involuntarily my dick twitched and in response she started rolling her hips almost imperceptibly slowly to set the stage for round 2.

Julia had been on HRT for over 3 years at this point and had developed those perky tits and, combined with a healthy squat routine, some nice wide hips and thick ass cheeks that drove me crazy. It was no wonder that my family never even considered the possibility that she wasn't cisgender.

"Are you going to tell them today?" she asked, hard eyes darting from her makeup past her earlobe to mine, catching me off guard. I stumbled and for a moment I felt like I'd shrunk a little inside her. Without hesitation she accelerated the roll of her hips, really working her asscheek muscles to slowly stir her insides with my dick.

"I can't and you know why," I squeeked out embarrassingly, "and this would be the worst time; almost all of my extended family is gonna be there..."

Jules could see it on my face and feel it inside of her: this question was a bridge too far for the moment and it was quite literally deflating me. She put down her pencil, grabbed both the hands I placed on her hips and squeezed them into her as she added a rocking motion to her elliptical movement, the effect of which was that half my dick was now slowly churning in and out of her wetness.

Meeting my lowered eyes in the mirror and raising them up to hers she relented, "Ok, you're right, my love. Let's get this meal over with and we'll discuss it another time." She then pivoted back to negotiations and added, "You can't fuck me deep right now though." pausing her movements for 2 seconds to establish her point.

"Wait, why not?" I blurted, trying to regain composure. "You mean you don't want all of this inside you?!" I countered, gripping the skin on the sides of her ass and adding a few half thrusts of my own giving her a little more girth and pistoning myself in and out a little quicker.

"No!" fell out of her mouth as she doubled over the counter, head falling into the empty sink. Without looking up she clarified, "I do, baby, so badly, but you can't rearrange my guts before breakfast. I'm sooo hungry and I plan on eating my way through any awkward comment your grandma makes about my 'birthing hips.'" (air quotes were thrown while her head was still in the sink).

"That makes sense, baby, I feel you." I said and fished my right hand up the front of her, picking her up out of the sink, running it right up her chest and resting it gently around her neck, standing her back up in the process. "You decide how deep I can go."

Julia had been doing kegel exercises daily for at least the two years we'd been together, and she could completely push me out of her on my horniest day, so if she wanted me to stay shallow, she was always in control and she knew that. She resumed the rocking elliptical motion with her hips and added a gentle squeeze at the top of my in-stroke indicating that was as far as I would be allowed to penetrate her. I settled my gentle thrusts into her rhythm, and we started fucking in earnest, stopping only briefly for me to drool some spit down her back and into her ass.

We were only a few minutes in when I could feel the shift inside her. Holding that kegel squeeze was a workout but she was up to the task. What she didn't anticipate was how I was slowly lifting her up with my thrusts and by raising the hand around her neck. This had a few effects: 1. It slightly lifted her heels off the ground and her hands off the counter, reducing her core strength; 2. It pointed my dick directly at her prostate, sending her waves of pleasure inside her on every stroke; and 3. It plopped her engorged clit right on the counter. As soon as I moved my left hand off her hip and clamped it around her girlcock she knew round 2 was conceded. Her eyes lolled around in the mirror, her hands fell limp against her sides, and she let the squeeze go completely. The very next thrust I buried myself to the balls and held her tight against me, feet dangling off the ground for a second or two.

Now that I was inside her fully and completely, she abandoned the muscles keeping me shallow and we got straight to it. Full strokes, gently jackhammering her thighs against the counter, her eyes came back into focus.

"Fuck, ok, take me baby, please..." she pleaded. "Fuck me deeeeep..." trailing off at the end.

I obliged.

Using her hard girlcock as a handle I pushed her back into me while simultaneously dropping her weight down on my dick and thrusting up. My pubes were sopping wet and slathered into the crack of her ass while my balls slapped the back of her tiny sack. She pushed her ass back into mine and on the apex of the deepest strokes I could feel myself pushing against her inner sphincter, which she lovingly referred to as her 'cervix'. I could see her face in complete ecstasy; a steady stream of drool had started to drip out of her mouth that I don't think she was aware of. I bounced her on my rock hard dick for 5 min or more, completely blissed out and making the most delectably wet slapping and squishing sounds, when I started to feel her little clit tightening in my hand. I looked down to see her spurting cum out in long ropes onto the counter and I almost blew my load in unison inside her.

I'm still not sure why I didn't cum at that very moment, I just wanted to watch her enjoy herself, I guess. And she did; thick white streams painting the countertop until her clit was done quaking. Since she had now cum, I had fulfilled her previous request and there was seemingly only one thing left to do so I slowly started pistoning my hips again, getting ready to blow my seed deep inside her.

At that moment Julia grabbed my hands and moved them back to her hips, bending herself over the counter, putting her face right in proximity of her freshly squeezed cum lined up on the granite. It took me by surprise when she started to lick and suck her cum up letting a long "mmmmmm" sound escape her lip. She had nearly cleaned the whole mess up when she stood back up abruptly, looked at me in the mirror and swallowed the whole load, draping her hands down her neck and resting on her stomach, following the path her cum took inside. I was so mesmerized I stopped thrusting inside her and she took the pause as an opportunity to crane her neck back to kiss me deeply, letting me taste the salty cum on her lips and tongue.

"You can't cum inside me," she turned and said matter-of-factly into the mirror, "I'm not dripping your cum out all morning with your father sitting next to me. Someone's gonna smell it and it's going to mess up my new skirt." And with that she hopped off my dick, turned and dropped to her knees. "I still want it though, feed me your cum baby."

Round 3

"Wait, what?" was all I could get out before she had the head of my dick in her mouth, "but you know that's my favourite thing in the world!" I added, defeated. She was amazing at giving head but thoughts of filling her up with my seed ran through my brain all day, every day, and she knew it. She loved it just as much and thought it a badge of honor to have leaked my cum out of her in at least a half-dozen restaurants in the city over the years, as well as at my parents house on a couple occasions. That's when I realized we weren't quite done negotiating.

Julia bobbed and swirled her mouth on my cock like she was starving but stared up at me with an intensity that begged me to make the next move.

"You know I need to put this load in your pussy, right?"

She nodded, cock pushing against the back of her mouth.

"And you want something from me before you let me shoot my seed in you?"

Nodded again, somehow deeper than before.

"What do I need to do?" I pleaded.

Taking her mouth off my shaft and coming up for air, "Two things: First one is that I want you to beg for it." she stated and plopped my dick right back in her mouth.

"Beg for it?! Absolutely!" She didn't have to ask me twice. "Please baby, take me in your pussy and let me fill you with my cum."

My trans goddess nodded for the last time, kissed the head of my dick and hopped up onto the bathroom counter facing me. Leaning back, she pulled up her legs and held her tiny package up against her stomach laying bare her pink, gaping boipussy. She cupped her hand up to my mouth and I spit into it knowingly. Pushing my spit into her hole she grabbed my dick and directed it to the entrance. In one slow motion I was back inside her pulsating ass, balls deep.

"Beg." she whispered and placed her ankles on each of my shoulders.

"Please, baby, let me cum inside you." I replied, feeling her 'cervix' in this position more intensely, "Can I please pump my seed deep into you?"

She nodded silently and I rocked my hips right into hers, picking her up in the process and increasing the tempo. Mashing the head of my cock against her deep inner sphincter with every stroke I was getting ready to paint her insides with my hot semen but I just had to ask. In between thrusts I squeezed out, "What. Was. The. Last. Demand?"

Julia grabbed my head with both hands, tightened up her kegel muscles around my dick like a vise, looked me straight in the eye and said, "You will tell your parents about me and we'll deal with the consequences. Together." She smiled sweetly at me adding, "it doesn't have to be today but promise me you won't keep my secret a secret for much longer, my love?" and before I could answer she pulled my face in and kissed me passionately.

As our tongues swirled around in their angry dance, she slowly wiggled herself down further into my lap. This time, instead of bottoming out on her cervix, it bloomed slowly and allowed my dick to turn the corner inside her sweet ass, placing me in the deepest part of her body and soul. We both inhaled and froze together in that hotel bathroom for a few seconds that seemed like an eternity.

Breathlessly I whispered, "I promise. I love you."

A big smile spread across her face and she mouthed, "Thank you, I love you too," and turning that smile into a needful pout, "and I want to have your babies, so breed me baby. Give me all your spunk as deep as you can!"

Her request put fire in my veins and ten full lengths of my manhood pumping in her pussy later, I started pulsing glob after glob of my sticky sperm in the deepest part of her belly, coating her colon with my gifts. Shaking and sweaty we slumped across the countertop to catch our breath.

Julia kissed me on my forehead and slid of me and onto the floor. Walking back to the bedroom rubbing her belly, she looked back with a winking smirk and a cheeky warning, "Thanks for that, love, but if YOUR cum stains MY skirt you ARE buying me a new one."

"So, when are you two going to settle down and make me a grandma?" The question rang through my head like a bell and pulled me out of the fog.

Looking past my mother I could see that at least a few other people were waiting on the answer to the same question but my usual method of laughing it off and deflecting wasn't coming out; the words stuck in my mouth. Almost in a trance I stood up from the table, drawing every pair of eyes at the table (and some neighbouring strangers') to me.

"Actually, uh, I have something to say..." I stammered, probably a little louder than necessary. I looked over at Julia and she looked up at me with her beautiful smile and wet eyes and nodded slowly. "I, uh, just wanted you all to know that Julia is a proud transgender woman and we weren't trying to keep it from you but I love her and she loves me and we're happy and I know that not all of you will approve and we will still love you regardless and we hope you will too..." I rambled, drifting off while staring out at the faces looking back at us. The kids at the table were oblivious, their parents a mixture of concerned and angry, and the grandparents mostly confused as to what I was even saying. You could hear a pin drop in the restaurant when Julia stood up beside me and squeezed my hand tight.

Her reassuring grip was a life saver and it solidified something in me, so while it seemed the air had been let out of the room and everyone was still reeling, I turned to her and said, "I love you, Jules, and I know you love me too and I don't need anyone else's approval to know that's pure and true." Dropping to one knee with her hand in mine I looked up at her confused face, eyes filling with tears and said, "I didn't plan this well, I don't have a ring, and I'm sorry I kept your secret against your wishes but, Julia, will you marry me?"

Through her tears she started nodding and with her free hand she deftly unwound one of the many hair ties holding her braids in place and handed it to me. I wrapped it around her finger over and over until it was secure. "Thank you." I whispered, kissing her hand, and the room exploded in raucous applause! Aunts, uncles, grandparents and cousins all got out of their chairs and came over, patting me on the back, hugging Julia and crying and celebrating with us.