Alright, so far things have gone nearly perfectly. After matching with Jess, you picked her up and took her out for dinner. Yeah, she’s much bigger than the pictures on her profile let on, but she’s still gorgeous despite being at least three times your size. She has short, wavy black hair, a sweet and kind face, and some of the biggest stonking TNA you’ve ever seen. She was wearing a simple white blouse that showed more than a modest amount of cleavage, and jeans so tight as to leave almost nothing to the imagination. So what if she was pretty fat, she was still really pretty. And so what if her appetite nearly broke the bank. You didn’t expect her to eat most of the appetizer, order a second entree, and dessert, but that’s alright. You did notice that she seemed a bit antsy throughout the date, making you think she wasn’t enjoying herself. However, when you brought her home after dinner, she invited you in anyway. Having no reason to turn down your beautiful date, you follow her inside. She leads you directly to her bedroom and sits down on the bed, skipping any pretenses of having coffee or some other innocuous end to the night. It’s at this moment that the gravity of the situation starts to dawn on you: you may be a bit outclassed in this matchup.
 
 
“That dinner was fantastic, thank you so much! You’ve been treating me so well!” she exclaimed excitedly. “But now I think I’m ready for dessert.”
“Huh, you already had the pie back at the…. Oh…” you say as her meaning dawns on you. She feels your reluctance, and begins to look very distraught.
 
 
“Oh, I’m sorry. I know I’m being very forward. I really enjoyed our date, but if I’m being honest, I was sort of waiting for this part the whole time. I’ve been very frustrated lately, it’s hard for me to find a man who will take me, and even harder for me to keep them. I went on this date really hoping that at the end I could find some… release.” She outflows this to you, and you suddenly feel terrible. Sure, going this hard on the first date was unexpected and a bit odd, but Jess was very sweet and earnest, and you would be lying to yourself if you said you weren’t turned on.
 
 
“No, no, it’s fine. Look, I was just a bit caught off guard.” you say, backpedaling. “I do really like you, I just wasn’t expecting things to go so far so quickly. But if that’s what you want, I’m happy to please.” The instant that these words leave your mouth, you are scooped up in her arms, face pressed firmly between her massive melons.
 
 
“Oh, thank you! I could just tell that you were the kind of sweetheart who would empathize with this big girl's struggles!” she said as she squeezed the air from your lungs. Once again, squeezed by her ferocious bear hug and nestled between her lovely tits, you felt somewhat disconcerted, but it was overpowered more strongly by your libido.
 
 
Without putting you back down, she lays down on the bed with you still in her arms, placing you beneath her as she straddles your much smaller form. With Jess on top of you, you fully understand the difference between you, as she easily conceals you entirely beneath her weight, save for your head poking out of her tits. She begins kissing you, clearly intending to french kiss, but it amounts more closely to her sucking on the lower half of your face. You do your best to reciprocate, which apparently satisfies her, as she pulls away and looks at you. Her face has become a bit sweaty with a deep blush, her expression somewhere between horny and hungry with a contented smirk.
 
 
“Oh my, you’re a really good kisser!” she says. Surprised by this, you respond “Really? I was just trying to keep up with you.” Bashfully, she tells you “Well, most of the people I’ve kissed act so overwhelmed that they don’t even consider such things. If you can handle this so well, how about we get a bit closer?” she asks, with a hopeful, if somewhat desperate expression, ignoring the fact that she already has nearly your entirely body squished beneath hers. “I don’t think that’s really possible, but I’m down to try.” you respond bravely, earning a happy squeal.
 
 
Jess climbs off of you, and begins slowly taking off her top in what was supposed to be her attempting to give you a strip tease. Watching her clumsily pull her top over her head, it’s easy to appreciate her charms. The definition of a bbw, she had perfect pillowy boobs that could swallow your head, an intimidatingly large, yet still bubbly butt, and a big soft belly that remained perfectly round despite its size. However, she carried herself lightly, with a rather soft touch despite however much she must have weighed. Sensing that she hasn’t quite hit the note she was aiming for, she more casually removes her bra, and stands in front of you wearing only her jeans, still tightly encasing her lower half.
 
 
With a slight sigh, she asks “How about you help me get these pants off? It took me ages to squeeze into them, I hope they didn’t make my ass look too big.” She wiggles her butt at you, each cheek visibly larger than your own head. “No, you look great. You have an awesome butt, I’m really excited to see it without those jeans.” you respond, kneeling down behind her to give her a hand.
 
 
“Aw, you’re just the sweetest thing!” she says with glee, clearly not having had a date go this well for her in awhile. She unbuttons the pants and bends over to try pulling them off, pushing her ass into your face in the process. Blushing and sweating very visibly, she asks with a slight tremble “Oh… Can you try to pull them down from back there? I’m a tiny bit sweaty and the pants are kinda stuck.” You grab on to either side of her waistband and pull, only managing to get it down a tiny bit. Changing tact, you attempt to pull lower down on her pants, only to find no slack to get a grip on. “Alright, let’s try pulling together. On 3.” you suggest. Counting down, you hit 3, and you both yank on either side of her pants, finally getting them over the hump of her overly generous ass and revealing her panties, which were white with little hearts all over. This also causes her to lose her balance, falling backwards into you. Thankfully the bed was behind you both to prevent you from being completely squished beneath your date.
 
 
You find yourself with your head pinned to the corner of the bed beneath her ass, your face shoved deep into the cloth of her panties. Rather than immediately getting off of you, Jess makes a small moan and begins gently gyrating herself on top of you for a moment. Her panties are already very wet, showing that she wasn’t lying about how much she was anticipating this. Your face is completely covered in her smell: musky, just a little sweet, just a little sour. Catching herself, she pulls herself away from you, looking down at your slightly crushed form with empathy and barely contained lust. You sense that it took a great deal of restraint on her part to have stopped when she did. “I’m so sorry, I just lost myself for a moment. I don’t normally get to do things like that.” Slightly confused, you tell her “No worries, but what do you mean?”
Her blush becomes even deeper, her eyes looking almost frenzied, “I really like being eaten out, but… I think my size makes it a bit too intimidating for most.” Maybe it was seeing such a beautiful girl acting so cute and shy, or maybe it was a minor concussion from having just been squished beneath her, but you felt overcome with empathy and desire for her.
 
You step close to her, attempting to stand on your toes to reach her face to give her a kiss, realizing that you were not even close to tall enough to accomplish this. Failing that, you give her a hug, your arms not even reaching halfway around her. She returns the hug, squeezing you between her tits again, then releases you. She watches curiously as you kneel down in front of her and begin to tug her underwear down. It takes a moment for you to remove her panties, still moist and clinging to her, but she watches quietly, biting her lip excitedly. Finally, her panties slip free and fall loose around her ankles, leaving you facing her bare crotch mere inches away. Even from here, you can smell her excitement, and see drips sliding down her thighs. Her folds were well kept and clean, it seems like she had probably shaved specifically for your date.
 
 
Steeling yourself, you push her thighs apart a bit to make room, and shove yourself between her folds, tongue extended. She gasps as she feels you, and wordlessly takes one of her legs and puts it over your shoulder. She then takes grasp of your head, and begins to grind herself into you as you attempt to find her clit with your tongue. You are unsuccessful in finding it, as she has shoved your head well past the clit, deep into her folds, but she doesn’t seem to notice.
After several minutes, and thinking you might lose your head between her legs, she steps off of you, panting.
 
 
“Oh my god. I haven’t felt that good in ages. How about we continue after getting a little more comfortable?” She says breathlessly, as she lays down on the bad, gesturing for you to follow her. “Oh, but first it’s your turn to give me a show.” Taking your cue, you pull your shirt off in a single motion and throw it to the side. You then undo your belt, allowing your pants to fall to the floor. You then lay down next to her, and she turns around to lay on top of you. She positions herself with her face next to your crotch, and pulls your underwear off, revealing your throbbing erection. She had clearly intended to 69 with you, but with your difference in size, her head being in position meant your own head was buried beneath her stomach. Undeterred, she gently licks your dick from base to tip, before sliding it into her mouth. All you can see is her navel pressed into you, but you can feel her lips and tongue sliding up and down your shaft, as she fondles your balls with her hands. It doesn’t take long before you feel yourself nearly ready to burst, but in your position you are unable to give Jess any warning. However, she was able to tell as you had started tensing up, and drove her mouth all the way down to the base, sucking hard. You cum hard into her mouth, but she keeps sucking until you are done and drained, only releasing your cock as it starts to soften.
 
 
She sits back behind you, your head now resting between her legs, the top of your head pressing into her crotch. Looking down at you, she says “I hope you enjoyed that. I’m so beyond ready to get off, I hope you're ready for me.” She said, her eyes a bit glassy. The intense desire in her expression, she looked like she was ready to swallow you whole. Scooting forward, she straddles your head, and immediately begins furiously humping your face. Her smell was far more intense now then when she’d sat on you earlier, your face completely lost within her folds. As she grinded into you, you continued to sink deeper into the desperate pussy, but you couldn’t tell since you had been lost within her folds from the moment she climbed on top of you. It was only once your entire head had sunk inside of her, and her lips reached the bottom of your neck that you noticed. Sensing the danger you were in, you tried smacking her on the ass to get her off of you, but that only excited her more, egging her humping on. As you continued to try and push her off of you, she finally took the hint… sort of.
 
 
“Oh, whoopsie. Sorry, was I crushing you? Here, let’s change positions.” She says, rolling over onto her stomach and bringing you along with her. With your head still trapped in her crotch, she was now laying with her ass in the air. You attempt to pull your head out, but only get as far as freeing your neck before she pushes back against you, pumping you back in. She begins to rock back and forth, sliding your head within her like a living dildo. The walls of her pussy begin to clench harder and harder against your skull, pulling you deeper. With a mighty clench and a torrent of slick, musky fluid, Jess lets out a sound halfway between a whimper and a moan as she cums all over you. The force of the clench, combined with her thrusting backwards against you and the extra fluid lubing you up, caused your shoulders to slip inside as well. “That was amazing, I haven’t felt anything like that in ages!” she exclaims in between pants.Trying to find purchase with your knees on the bed, you again try to pull yourself out. However, Jess reacts to this in the least helpful way: she sits back.
 
 
Feeling you attempting to extricate yourself caused another wave of pleasure to pass through her body, surprising her, causing her to sit back on top of you. “Oh, are you ready for a round 2 right away? Perfect!” she says with a lusty grin. Sitting back had forced you even deeper into her musty depths, and you now found yourself trapped up to your waist. Readying herself for more, she returns to her position on her belly with her butt up, with your lower half now protruding from behind her, legs flailing in the air. Your desperate squirms are more than enough to stimulate her, and gravity aiding her clenching pussy causes you to sink further and further inside. Soon, you find yourself with nothing but your feet remaining outside, and with a wet POP those too join you inside the steamy depths of your date’s dripping pussy. Sealed entirely within her still furiously horny loins, you felt her sticky, wet walls squeezing you from every direction. It almost feels sort of nice, like an extremely intimate hug. As her pussy continues to squeeze and grind on you, your mind begins to go fuzzy. You barely even notice as your body starts to become soft and mushy, mixing with the femcum that you are being bathed in. Her pussy continues to squeeze into you, more and more intensely, until finally she cums again, mashing the remains of your form into liquid. The torrent of cum that once included your body comes gushing out of the now very pleased pussy, drenching a portion of Jess’ bed and spilling onto the floor. Panting, Jess simply lays there for a few minutes, lost in the afterglow, before it dawns on her that she hasn’t heard you say anything in a while. Sitting up, she looks around to see that she is alone. She then looks at the massive mess she has made, with my now drenched clothing in a pile on the floor.
“God damnit, not again. This is what I meant when I said a good man is so hard to keep…”