The Dildo Game

Yet another restless night haunted by Nick’s videos and the cold reality of CalcSD charts, you leave work early and drive across town to a seedy adult bookstore on the outskirts. The neon sign flickers “XXX Video & Toys” above a blacked-out storefront. Your heart hammers as you step inside, the smell of latex and stale incense hitting you immediately. A bored goth clerk barely glances up from her phone.You move to the dildo wall like a man on a mission. Silicone cocks of every size hang in glossy packaging. You grab one of each category, pulse racing:Mini: 4 inches long, slim 3.5-inch girth – almost a joke.

Small: 5 inches, 4.5 around – close but still bigger than you.

Medium: 6 inches, 5 inches thick – respectable.

Large: 7.5 inches, 5.75 girth – intimidating.

Exxxtra Large: 9.5 massive inches with a 6.5-inch circumference, veiny and realistic with heavy balls at the base.

The total makes your wallet hurt, but the shame-fueled erection in your pants makes it worth it. You drive home with the discreet black bag hidden in the trunk, cock leaking pre-cum the entire way thinking about Tawny’s reaction.That evening you open a bottle of her favorite red wine. Two glasses in, Tawny is giggly and flushed, her tight tank top straining over her massive tits and yoga pants hugging her thick ass. You’ve already set up the game: an old cardboard box with a hole cut in the side just big enough for an arm. The five dildos stand upright inside like soldiers awaiting judgment, lubed and ready.“Baby, I want to play a fun game tonight,” you say, voice thick with nerves and arousal. “Blind comparison. You reach in, pick one, and… tell me how it compares to me. Mouth and pussy. Be honest.”Tawny raises an eyebrow, wine glass paused at her lips. A slow, mischievous smile spreads. “You’re really still on this size thing? Okay, perv. But only because you’re cute when you’re ****.” She sets her glass down and kneels in front of the box in just her tank top and panties, heavy breasts swaying.

“Let’s see what Mommy pulls out.”Her hand disappears into the hole. You watch her arm move, fishing around. She pulls out the Medium – the 6-inch veiny realistic one, already glistening with lube.“Oh wow,” she laughs, holding it up. It looks huge in her soft hand compared to what she’s used to. “This one feels… substantial.”

Your cock twitches in your shorts as you strip naked. Your 4.33-inch erection points up angrily, already leaking. Tawny places the medium dildo on the coffee table next to your dick for side-by-side comparison. The difference is immediate and humiliating. Yours looks like a smaller sibling.

“First, mouth,” she purrs, clearly getting into it. She leans forward on her knees, massive tits resting on your thighs. She takes your cock into her warm, wet mouth first – easy, all the way to the base with no effort. Her tongue swirls lazily. “Mmm, familiar… cozy.”Then she turns to the medium dildo. Her lips stretch noticeably as she takes the head, cheeks hollowing. She bobs deeper, forcing more in until she gags softly around the fourth inch. “Fuck… bigger,” she gasps, pulling off with a wet pop. Saliva strings connect her lips to the silicone. “My jaw has to work for this one. Feels thicker on my tongue too.”Your face burns with arousal and shame. Precum drips down your shaft. “Now… pussy?”

Tawny stands, peels off her soaked panties, and lies back on the couch, legs spread wide. Her puffy, shaved pussy glistens. She rubs the medium dildo up and down her slit, teasing her clit, then slowly pushes it inside.“Ohhh… shit,” she moans, eyes fluttering. You watch inch after inch disappear into her until the fake balls press against her ass. She’s stretched more than usual, her lips gripping the thicker shaft. “It’s filling me up. Hitting deeper than you usually do, baby.”

You stroke yourself slowly as she fucks herself with it – long, deliberate strokes. Her huge tits bounce under her tank top. Wet, squelching sounds fill the living room. “Deeper… fuller,” she pants. “I can feel it pressing my cervix almost. God, it’s good.”

You can’t take it. You pull the dildo out with a lewd pop and slam your own cock into her. She’s noticeably looser after the medium, but still warm and wet. You thrust frantically, but Tawny’s hand sneaks down to rub her clit hard. She cums with a shudder, but it’s clear the dildo had already done most of the work.You pull out and cum across her soft belly in weak spurts.

“Round two?” she asks, still flushed. You nod desperately.She reaches in again. This time she pulls the Large – 7.5 inches of thick, veiny silicone.Her eyes widen. “Holy fuck, this one is big.” She holds it next to your rock-hard dick. The comparison is brutal. Yours looks tiny beside it.Mouth test: Tawny struggles visibly. Her lips stretch wide around the fat head. She only gets about halfway before gagging hard, eyes watering.

“Jesus… my throat feels full already. Can barely get half.” Drool runs down her chin onto her cleavage.

Pussy test: She lies back again, rubbing the massive head against her entrance. “Go slow…” she whispers. You watch in awe and jealousy as her pussy lips part obscenely, stretching around the thick shaft. Inch after inch sinks in until she’s stuffed. Her belly even shows a slight bulge.“Fuuuuck… it’s so deep,” she groans, voice husky. She fucks herself harder, hips bucking. The wet sounds are louder, sloppier.

Her massive tits bounce wildly as she chases pleasure. “It’s hitting spots you’ve never reached, baby. I’m so full.”You’re stroking furiously now. When she cums – a real, squirting orgasm that soaks the couch cushion – you lose it and add your own load to the mess on her stomach.The wine flows. Tawny’s inhibitions melt. She reaches in a third time and pulls the Exxxtra Large – the 9.5-inch monster.

“Oh my God,” she breathes, genuinely shocked. It looks obscene in her hand, wrist-thick and heavy. Next to your dick it’s laughable. Yours barely looks half the size.Mouth: Tawny attacks it like a challenge. Her jaw stretches painfully wide. She gags repeatedly but forces more than half down her throat, mascara running. “It’s fucking huge… my mouth feels stretched out.” She coughs, strings of thick spit everywhere, tits shiny with drool.Pussy: This one takes time. She lubes it generously and works it in slowly, moaning like a whore. “Baby… it’s splitting me open. So fucking deep.” You watch her pussy swallow almost the entire thing, her lips puffy and gripping desperately. She fucks herself to a screaming orgasm, legs shaking, juices squirting around the massive dildo. Her eyes roll back.You can’t even compete. When you slide into her afterward she feels stretched and loose, almost like fucking warm jelly. She still moans encouragingly, but you both know the truth. You cum quickly from the humiliation.

By now the room smells of sex and wine. Tawny, drunk and horny, insists on continuing. She reaches in again.

Small this time. Closer to your size. She laughs. “This one feels more like you… but still a little thicker.” The comparisons are gentler, but she still notes it feels “fuller” in her mouth and “more filling” in her pussy.

Then the Mini. She giggles uncontrollably. “This is cute. Like a little training cock.” She sucks it easily and slides it in with almost no resistance after the XL. “Feels like… nothing compared to the big ones now.”The night devolves into chaos. She makes you fuck her after each dildo, comparing directly. She rides the Large while sucking your cock. She takes the Exxxtra Large doggy-style while you lick her clit. At one point she has the Medium in her pussy and the Large teasing her ass while she blows you.You lose count of her orgasms – real, shaking, squirting ones with the bigger toys. Your own climaxes feel smaller, weaker.

By 2 AM she’s a wreck: covered in lube, cum, and her own squirt, hair messy, tits marked with hickeys.She pulls you close, kissing you deeply. “This was so fucking hot, baby. I love that you’re exploring this.” Her hand finds your spent, sticky cock. “Even if you’re smaller… you’re mine.”But as she falls asleep, you lie awake staring at the ceiling, the five dildos lined up on the table like trophies. Your mind races with new fantasies – showing her Nick’s cock, inviting real competition, pushing the humiliation further.