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Crazy things are done.
"I know honey," Henry said. "I love to watch you do it too though. I love how big your nipples get when they get aroused. Are you getting wet? Is your pussy starting to tingle?"
"A little. Please come in Henry. There's a milk crate over by the side of the garage."
"I want to watch you get off honey," Henry said, and after reaching into his robe pocket pulled out the vibrator and handed it to the girl through the window. "I want you to get on the bed and lay back, and then I want you to spread your thighs and pretend that it's my cock and slide it in and out of your pussy."
"I don't know how," Debbie said as she looked at the device. "Your thingy is bigger than this."
"This will get you used to it so when we make love it won't hurt."
"Will this make me bleed? Jennifer says that when you first do it you bleed."
"You've never put anything inside of you before?" Henry asked. "Nothing at all?"
"My finger, but not too far. Just around the tingly part."
"You probably won't bleed honey," Henry said. "Just sit down and then lay back and open your legs."
"Please come in - we'll be real quiet," Debbie whispered as she got closer to the window, so close that the senior could smell her pussy. "I'll help you in."
"All right," Henry said resignedly, and as he looked over and saw the metal box Debbie was talking about he headed over while muttering to himself, "I must be getting soft in the head."
The same couldn't be said for the old man's cock, which was tenting out the front of the pajama bottoms after the little show Debbie had put on, and when he returned Debbie had already opened the window all the way and was waiting.
Henry figured he must look like an idiot climbing into an 18 year old girl's bedroom wearing a bathrobe and pajamas, but the smell of her pussy was even coming through the window and it was that carrot-on-the-stick and got him through the window, awkwardly as it was.
"You okay Henry?" Debbie asked after helping the old man to his feet, and Henry nodded as they embraced, his hands squeezing Debbie's plump cheeks.
"Get on the bed," Henry whispered, and after she did Henry made his creaky knees go down to the carpet while spreading the teen's legs and putting them over his shoulders. "Oh honey, you're so wet."
"I know. Please help me. I've been tingly all day," Debbie pleaded, and after Henry reminded her to keep quiet grabbed the vibrator and lowered his face into the girl's dripping grotto, a valley so wet that the down around her mound was flattened.
"Oops," Henry whispered when he turned on the vibrator and realized that even though it probably sounded real loud because he was right next to it, it was still too loud to risk so he kept it off and eased the thin probe between her labia, or at least tried.
"Relax honey," Henry whispered as he teased her clitoris with his tongue while trying to get the vibrator into what felt like a keyhole.
"It's too big," Debbie said as she grabbed the backs of her thighs to spread her legs wider, and only after spinning and coaxing did her manage to push some of the vibrator into Debbie who let out an oohhh in response.
"There honey," Henry said softly as he worked in the end of the device which was no bigger than his thumb and smaller than his own modest manhood, but something Debbie was reacting to as if it was a baseball bat. "How's that?"
"Good," Debbie hissed. "Wish it was your thingy."
"Me too," Henry said as he worked the end of the vibrator in and out while lapping at her sex, and the faster he went the more Henry worried about Debbie making noise when she came.
She did her best, but even the stifled squeal sounded like a roar to Henry as he pressed her pussy to his face by letting go of the vibrator and grabbing her butt, but after he pulled the device out of the spent girl his worst fears were answered.
"Princess?" came a male voice at the door along with a light tapping sound, and with that Henry looked at the open window for a brief second before exchanging terrified looks with Debbie in the murky darkness.