🎲 Surprise Me

Results (1403)

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and then it sends you back to sleep, 'cause it feels like fentanyl.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#241
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I don't know. I like it.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#242
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I like sitting on the couch on a Sunday
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#243
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and just a nice pinch and roll on my beanbag, you know? Just…
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#244
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[crowd laughs]
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#245
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[man whoops]
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#246
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-[scattered whistling] -[Tom sighs]
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#247
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"This is free? This is crazy."
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#248
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[crowd laughing]
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#249
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"I wish it were Seven's hand, but this feels good, you know?"
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#250
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A lot of ladies get jealous about that, and honestly, you shouldn't.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#251
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I've seen what you have there, and there's plenty to pull,
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#252
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so you could also just…
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#253
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[crowd laughs]
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#254
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Tug on that taffy bag and see where it takes you.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#255
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[crowd laughs]
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#256
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[Tom sighs]
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#257
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Yeah, and don't you dare get insecure, okay?
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#258
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You ladies do that to each other. We never care.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#259
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It could have teeth, and we try to get in there. We don't care.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#260
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All I'm saying is, ladies, I want you to leave here tonight
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#261
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knowing that you all have beautiful pussies, okay?
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#262
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Yeah, sure.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#263
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[cheers rise]
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#264
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Oh yeah, absolutely.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#265
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So I'm peeing, right?
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#266
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Um…
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#267
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And as I'm peeing, I feel something, you know, in the chamber.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#268
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And I'm polite, so I do the polite thing.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#269
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I… hmm… mmm…
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#270
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look around, and there's nobody in there.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#271
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So I tell myself, "It's okay, buddy."
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#272
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"Why don't you give it a push?"
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#273
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And I did,
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#274
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and there was no sound.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#275
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None.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#276
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But there was movement.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#277
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So now I have to check.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#278
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Do you know how you have to check?
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#279
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You have to take your pants all the way down.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#280
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Like a fucking toddler. I was like…
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#281
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So now I'm just Winnie the Pooh-ing it in a T-shirt. Like…
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#282
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"Hi."
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#283
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"Hello."
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#284
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My little dick's hanging out.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#285
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"Hello."
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#286
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Then I look into my boxers, and I'm like, "Yep, I'm throwing those out."
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#287
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And then I clean up, and then I leave the restroom.
Tom Segura: Teacher (2025)
S01E01 — Tom Segura: Teacher (2025)
#288
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