MMTTD Jess’ Experience(f/m)

AN: This is a request I did for brownjosh123 . This is a part of my My Mom the Tickling Dom series and it features Amanda, Amy’s mom. Feedback is appreciated. 

Originally posted Nov 17, 2020

Jess was an 18 year old young man. He always wanted to be tied up and tickled. He was too young to before, but now that he’s turned 18 he’s been looking for the opportunity. His parents were going on vacation and leaving him alone for the weekend. He just had to figure out how he would get this done. Jess got on the computer and began searching the web. He was a bit hesitant, but he figured the web was where he would find such a place. Finally, he found the place. It was called The Tickling Dungeon. It had good reviews and it was local. Jess wasn’t sure. He had been a pure boy and something like this might be too much. But, he knew he had the opportunity and he had to take it. He filled out the questions and booked the session.

Meanwhile, at The Tickling Dungeon, Danielle received the order and brought it to Mistress Amanda. This was while she still ran the place.

“Someone just booked a session with us online,” Danielle handed the papers to Amanda, “He’s a new customer named Jess, he says he’s 18 and has signed up for two hours.”

Amanda looked at the file and smirked, “It’s obvious he’s never done this before. This would be an intense session even for a regular. He’s asking for way more than I think he understands.”

“I’ll go see who wants to do this session,” Danielle started walking out.

“Actually,” Amanda stopped her, “I think I’ll do it.”

This sounded like a very interesting session to Amanda. Things had been slow recently and this might be just the thing to get her out of her rut.

Jess greatly anticipated the day his session was and finally it came.

We’ll see you later!” Jess’ parents yelled as the left.

Once they were gone, he got prepared. Jess arrived 30 minutes early. He walked in and went to the front desk.

“Do you have an appointment?” Danielle asked.

“Yes, my name is Jess, my appointment is for 2,” he responded.

Danielle typed on her computer, “You’re a little early. I’ll see if she’s ready for you,” she went to the back and Jess sat down in the waiting room. Danielle came back a few minutes later, “She will see you now in room 2.”

Danielle held the door open while Jess went inside. He went to room 2 where Amanda waited inside. Amanda saw him walk in and didn’t believe he was actually 18.

“Just as I thought, you’re just a kid. I’ll refund your money. Now get out of here, come back when you’re older,” Amanda said waving him off.

“No, I’m old enough, see?” Jess quickly grabbed his ID and showed it to her.

Amanda grabbed it and looked at it closely, “You just turned 18, and you are already doing something like this? How naughty,” Amanda teased giving him back his ID.

Jess was often mistaken for someone younger. He was skinny and short. He could get away with saying he was 14.

“I am Mistress Amanda. Let me explain how things are done here. First of all, I am in charge here. I will remember what you have filled out, but I decide when and how it is done. You must do as I say or you will be punished,” Amanda put emphasis on that last sentence, “This place is focused on tickling, you have signed up to be tickled. I will tickle you mercilessly until the time is up, or you tell me to stop. There is a safe word we use here to tell us to stop. The word is orange, remember that in case you need to stop. Once you use that word, I will stop and the session will be ended. I will use the tools you see around you to tickle you. Finally, have fun. We’re all about fun here.”

Jess was looking forward to starting. His Mistress was sexy. Amanda was was a mature, and curvy woman. She was obviously older than Jess. And she had on a nice leather outfit that showed off her features.

“Now then, strip for me,” Amanda commanded.

Jess took off his clothes but stopped when he got to his underwear.

“I didn’t tell you to stop did I?”

Jess was blushing a deep shade of red as he took his underwear off. His cock was already standing upright.

“Good, now let’s get you tied up,” Amanda tied him to the table spread eagle. She wanted to show him what he had gotten himself into. She started by lightly tickling his belly with her nails.

“Hehehehehehehehehehehehehe!”

“Coochie coochie coo~ There’s no need to hold back~”

“HAHAHAHAHAHAHAHAHAHAHAHAHAHA!”

Jess couldn’t help it anymore and started laughing hard. Amanda noticed how sensitive he was. She quit her attack on his belly for a second.

“Have you ever been tickled before?” Amanda asked him.

“No never. But, I’ve always wanted to,” Jess responded.

Amanda felt a little sorry for him. Never been tickled before and now he was under her fingers. But, she also liked the idea of tickling this very sensitive young man for the first time. She was going to tickle him until he begged.

She began tickling his armpits.

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!”

Amanda was barely tickling him and he was already bursting out laughing. She took note of that and moved on. She began tickling his thighs and legs to see what laughter she could get.

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!”

There didn’t seem to be and part of Jess that wasn’t super ticklish. She moved on to his feet last, digging her nails into them.

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!”

His feet were so soft and sensitive. Amanda determined that his armpits and feet were more sensitive, but he was very ticklish from head to toes. She thought she would start out by teasing him with the large white feather. She brought it to his neck first. Jess had a smile on his face but held back from laughing, he was having a hard time. She brought it to his chest next where he started to break with a little bit of laughter breaking through. She suddenly brought the feather to one of his armpits. Now he was laughing a little.

“Hehehehehehehehehehehehehe!”

“Tickle tickle tickle~ Are you having fun yet?~”

Jess was actually kind of frustrated. One minute she was tickling him hard, and now she was only giving him slow, light tickles.

The feather slowly found it’s way to his belly where Amanda brought it back and forth.

“The feather sure is fluffy, isn’t it?~ I could just keep waving this on your belly forever~ But I won’t,” Amanda stopped tickling, “Now that I’ve gotten you warmed up, let’s really begin.”

She put the feather away and grabbed the blindfold. After putting it on him, she went back to grab her next tool. Jess couldn’t see what she was doing, but he was excited for whatever come next. He heard a bottle open and was quickly caught by surprise when he felt her touch his underarms. She was rubbing some sort of lotion or oil onto them. Then she used her nails and tickled them.

“BWAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!”

Amanda was furiously attacking his armpits with her nails.

“Coochie coochie coo~ Your armpits are so sensitive~ They deserve all these tickles~”

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!”

His laughter was so intoxicating. It had been forever since she had tickled anyone so sensitive and inexperienced. He had signed up for 2 hours, but she felt it was going to be hard to stop.

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!! ITTICKLESSOOOHOOHOOHOOMUCH!!!HAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!”

“It’s only been 15 minutes~ We still have a while to spend together~”

Amanda kept tickling his armpits for a few more minutes. Afterwards, she went to the wall for her nest tools. Jess was beginning to think he may have signed up for too much. This woman was really good at tickling, and he was with her for 2 hours. He heard her come back over and then she turned on something that buzzed. The buzzing thing made contact with his belly and he started laughing away again.

“HAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!”

Amanda brought the toothbrush around and around. It circled his belly until it got to his belly button.

“I love the toothbrushes, they never fail to bring out the most wonderful laughter~”

While she used the one toothbrush around his belly, she quietly brought a second toothbrush she had been hiding over. She turned it on and used that one on his belly too.

“HAHAHAHAHAHAHAHAHAHAHA!!!”

Once she felt she had tickled every spot on his belly, she brought the toothbrushes to his underarms.

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!!!ITSTOOHOOHOOMUCH!!!!!HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!!!”

She tickled his armpits for a few minutes before moving the toothbrushes to his nipples. It didn’t tickle very much, but his cock began twitching. After that, she switched them off.

Amanda opened the bottle of oil back up and began massaging it into his skin. Jess needed a break to catch his breath, this was beginning to be a little too much for him. He began to realize how stupid he was to start with a 2 hour session. He was brought out of his thoughts when he felt her start rubbing his cock. A moan escaped his lips which made him embarrassed. It felt so nice, and it was a welcome change of pace after the harsh tickling he had just been through. But, he wasn’t aware that Amanda would only be harsher, and that she wanted to tickle him until he screamed and begged. She finished the massage, leaving Jess a bit frustrated. He was really turned on by the tickling, and playing with his cock only made it worse, he really needed to cum. Amanda had no intensions of making him cum just yet, she was grabbing her next tools to tickle him. He heard her come back, this time to the other end of the table by his feet. She began brushing something on his feet.

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!!!”

Amanda began furiously using hairbrushes to brush his now oiled feet. His soft feet were already super ticklish before, but now they were unbearably ticklish. And Amanda knew just how to brush someone’s soles.

“Tickle tickle tickle~ Do you like my brushes~ I think you do~”

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!!!”

Amanda couldn’t remember anyone ever laughing this hard before. This was heaven for her.

“Coochie coochie coo~”

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!!!”

She couldn’t help but tease him. He responded so well to it.

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!!!”

Jess’ soles were so wonderfully ticklish, she got lost in tickling them and accidently tickled them for 45 minutes straight. Once she realized how long she had been tickling them, she stopped. The poor boy looked ready to pass out as he gasped for for air.

Jess couldn’t believe what he had just been through. But, even though it was harsh and sadistic, he loved it. Amanda was having lots of fun too.

She had a little bit of time life left and she knew just how she would use it. She used her nails to tickle the rest of his oiled body.

“HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!!”

His belly, his chest, his sides, his thighs, his underarms were all so ticklish.

“Tickle tickle tickle~ Just keep laughing for me~”

Time was almost up and Amanda only had one more thing left to do. She grabbed his cock with her right hand and began to stroke. With her left hand, she lightly tickled his belly. He came hard, the hardest he ever had.

Amanda untied Jess and brought him to a chair. She handed him his clothes and got dressed.

“So what did you think of your first time?” Amanda asked.

“It was amazing. Even better than I expected.”

“If you ever come back, I’ll be happy to do this again,” Amanda told him.

Jess left satisfied with his experience. And Amanda had once again found her love for tickling.