Probation Tickle

Dylan was 18 and on probation. He had done some stupid things, nothing to serious - in his mind at least - but still here he was at the court ordered doctor's office.

Dr. Stein was an older woman with white hair who looked like his grandmother. Also present was his PO (probation Officer) Officer Jenson. Short blonde hair and kind of cute to be honest. She had two dimples when she smiled.

"Ah, Dylan. Right on time. Now please strip down to your underwear and lay down on the table." Dr. Stein said.

"Wait. I didn't know almost being naked was part of the treatment," Dylan said, suddenly nervous. He was a good-looking arrogant guy who knew how to use that to his advantage. Tall, muscular with a full beard and mustache. Bright blue eyes and a charming smile. His arms were full of tattoos which made him look tough - in his mind.

Dr. Stein wasn't impressed with guys like Dylan. She'd been doing treatments for 30 years and saw every type of man and woman. She always modified their behavior. Sooner or later.

Officer Jenson looked young but had been on the job for five years. She too knew Dylan's type. She wasn't impressed by him either. She often helped Dr. Stein in her treatments. It was fun to break men like Dylan down. They never saw it coming either. That was the best part.

"Strip now!" PO Jenson said.

Dylan took off his clothes. Once he was secured to the table, Dr. Stein explained her method of treatment.

"You'll be tickled all over your body. Rest will come only when I give it and not before. There is no "safe" word," she said using finger quotes around the word safe.

"Do you like being tickled?" PO Jenson asked.

"I don't know. No one's ever tied me up to tickle me before," Dylan answered.

"Well, you're about to find out," Dr. Stein said.

"Is this even legal?" Dylan asked.

The two women looked at each other and laughed.

"Now looks who suddenly concerned with the law," PO Jenson said.

"If only you had thought about that before you got on probation," Dr. Stein said.

Then she reached out and ran a fingernail up his left foot. Dylan jerked away as best he could, but he was tied down tight. He burst out in a choaked laugh.

Both women looked at each other and laughed again.

"I guess he is," PO Jenson said, reaching out to tickle his right foot. Then both women were tickling him on his feet.

Dylan was laughing and thrashing on the table.

"We know his feet are ticklish. How about his pits?" Dr. Stein asked.

Each woman stood by his head, one on each side and without warning, poked their fingers into his armpits. Dylan jumped and laughed and turned his head trying to bite their fingers but couldn't reach.

Suddenly Dylan felt a slap on his face. "No biting!" PO Jenson shouted. Then moved down and pinched his nipple. Dr. Stein did the same.

"Ow! Okay. I'm sorry. Stop you're hurting me!" Dylan said.

Both women leaned down and licked his hard nipples, then blew cool air on them.

Dylan closed his eyes and moaned.

Then he felt fingers tickling his ribs and stomach. All those crunches didn't protect him from their tickling fingers.

He was already starting to get excited, but when they tickled his upper thighs, that's when he felt and saw his cock become fully erect.

"Oooh! Someone likes being tickled," Dr. Stein said, reaching down and tickling his balls.

"It sure looks that way," PO Jenson said, dragging her fingers up and down his shaft.

Before he knew it, his underwear was cut off and PO Jenson was stroking his cock, while Dr. Stein tickled his balls.

"Are the girls impressed with this big old cock?" PO Jenson asked. 'Holy shit this is the biggest cock I've even seen. Long and thick', she thought.

"Nice hairless balls too," Dr. Stein said, fondling and tickling them. Then she traded with PO Jenson and took over stroking Dylan's massive cock. She'd never seen one as big either. She wondered how much he could shoot if built up enough.

Dylan was moaning and grunting. He was close to shooting his load by a woman who looked like his grandmother but had the softest hands.

Then they stopped.

"You didn't think we'd actually finish you off, did you?" Dr. Stein said.

"I was kind of hoping, yeah," Dylan said disappointed.

"Dude, you're on probation. Not at a massage parlor where happy endings are included," PO Jenson said.

They then proceeded to tickle him some more with feathers, electric toothbrushes and other things he didn't know the names of. His cock remained hard the whole time.

"So, are you ever going to commit a crime again?" PO Jenson asked when they had finally given Dylan a rest.

"No. Never. I learned my lesson," An exhausted Dylan answered.

"Well, then in that case," Dr. Stein said and started stroking his cock. "I guess you deserve a reward for being tickled today."

PO Jenson tickled his balls. Both women were looking at him in the eyes.

Soon, Dylan shouted he was going to come and come he did. PO Jenson had guessed right he shot a massive load of cum in the air all over his chest and Dr. Stein's hand. She kept stroking, getting every drop out. Then a surprised Dylan watched as she licked his cum from her hand. That was topped by PO Jenson bending down and licking his cock clean. Soon both women were licking the cum from his body and cock.

They untied him, watched him dress and told him to return next week.

At first Dylan thought probation would suck, and it literally did, but in the best way. He hated being tickled, but the rest was awesome. Would it be like this every week?

Shit! Dylan thought. Stupid fucking car. "Mom! I need a ride to my probation appointment," Dylan said.

After pulling up to the house his mother was surprised. "You meet your probation officer here?"

"Well, I have to do these treatments and it's actually at the doctor's house."

"Treatments! What kind? Are they giving you drugs? Maybe I should come in..."

"Mom, chill out. It's not drugs. It's more behavior modification," Dylan said, proud of himself. He'd be totally embarrassed if his mom saw him getting jacked off by an old woman and his hot PO. If that even happened again.

"Just drop me off and come back in an hour."

Dylan, still being a cocky little shit, took off all his clothes and lay on the table.

Hairbrushes were used on his feet to start this tickle session. Then they added oil and that made it worse. He popped a boner right away.

PO Jenson used the oil on Dylan's cock and stroked it while Dr. Stein tickled his balls with an electric toothbrush.

Dylan was laughing and moaning. Just before he shot off, Dylan saw his mother walk into the room. The other women turned and saw her enter the room as well.

Without a word, the two women continued their tickle assault on Dylan's cock and balls. Then PO Jenson looked into Dylan's mother's eyes as she rubbed her thumb under the head of his cock until he popped his load.

"So, this is the behavior modification you mentioned?" his mother asked.

"Mom, please go wait in the car," A red faced Dylan pleaded.

"Yeah, right," Bonnie, Dylan's mom said.

"So, you're Dylan's mom. I'm Dr. Stein and this is his PO Officer Jenson."

"Bonnie. Nice to meet you, so, who wants to explain the hand job?" His mother asked.

"Well, we start with tickling, but sometimes they need a release. So, we offer a quick hand job.

"I guess I should have tried tickling instead of grounding. Being a single mother isn't easy."

"No, it isn't. PO Jenson said. "I've had to bring my own son in for tickle sessions with Dr. Stein. Shaped him right up."

Dylan thought about another 18-year-old being jacked off by his own mother. It kind of thrilled him.

"Well, I think he should return the favor," Bonnie said. "Dr. Stein. Climb on up there and see how well my son eats pussy."

She looked at PO Jenson who nodded and then removed her clothes and climbed on Dylan's face. He was surprised her hairless pussy tasted so good. She came in no time. Then PO Jenson climbed on his face, and he went to town on her pussy and clit. She too was hairless. He sucked on her clit until she cried out and came all over his face.

When his mother mentioned his butt was ticklish, he was untied and retied with his butt in the air and his face on the table. Feathers, toothbrushes and fingers were used all around his ass and asshole. Then one woman licked his balls, one his cock and one his asshole. Then they rotated. Dylan figured out his own mother had just licked and sucked his cock and balls and given him a rim job.

At some point his mother had gotten undressed and climbed up on the table underneath him in a 69 position. She told him to eat her pussy while she sucked his cock and Dr. Stein and PO Jenson played with his balls and asshole.

He made his mom come after a while of licking and sucking. Then he felt his balls in someone's mouth, a tongue in his asshole and his moms tongue circling around the head of his cock and he lost it and shot his load inside his own mother's mouth.

She climbed off the table and shared his cum with the other two via a French kiss.

Dylan was a changed man after that. He was still tied up and tickled by his mother and often times her friends who came over to visit, even though he never got in trouble again, this became a literal bonding moment for mother and son. He got to tie her up a few times too. He liked bringing her to the edge and stopping, then holding a vibrator on her clit while he fingered her to a huge orgasm.

After his probation was over, he never saw Dr. Stein or PO Jenson again, but some of his friends who got in trouble told wild tales of being tickled by the two. No one believed them, but Dylan did. He never said a word about it though. Those were memories for him and him alone.