Theme park fun

My best friend (25f) and I (24f) have had annual passes to our local theme park for many years now and tend to go every other weekend. This year for my bf’s (24m) birthday I purchased him a pass so he could join us. This story was from our trip to the theme park this last weekend.

The morning started with the alarm going off at 7:30am to get our day started early for a full day at the parks. My bf is a very heavy sleeper, so I woke him up with hard taps to his “morning wooded” locked cock. (He’s been locked up for about 2 months nonstop in his pink HT nub). He after a min of recovery got up to make us our morning coffee and bagels. We moved on to the shower where he eagerly licked me to a quick orgasm and I got dressed while he finished showering and shaving. The door rang as my friend Kim arrived to join us for the day.

She was wearing a tight crop top and volley ball shorts to deal with the summer heat we would be experiencing today. Kim had played with us in the past, so having my bf walk around in a towel from getting out of the shower was nothing new to her today. He greeted her, but knew that if she was here, he was going to have a long day. I pulled off his towel and invited Kim to help me pick his outfit for the day.

I lead him by his cage to the bedroom with Kim following. With her help, we decided on a bright pink g-string. He reluctantly put it on and complained it rode up his ass. Kim laughed and proceeded to give him the deepest wedgie “does that help” she asked as he let out a yelp. I laughed knowing he really asked for that one. I packed a quick to-go bag and we got in the car. I made an executive decision that he would be in the back with his pants pulled to his ankles for maximum humiliation. We all jammed to music for our dive there, little did my bf know… Kim and I planned quite the day for him.

We parked and my bf began to pull his pants back up and get out of the car, I ordered him to close the door. I handed Kim the key to his cage on a necklace and the to-go bag. “Today you refer to Kim as mistress K, she will in charge of u for our trip and u will do everything she asks” he rolled his eyes but responded sheepishly with a “yes mistress”. She put the key around her neck and rummaged through the bag. She pulled out a medium plug, small bottle of lube and a period pad and joined him in the back seat.

She pulled him over her knee, pulled his pants down and with no warm up, shoved the lubed plug deep inside him while he let out a loud moan. His face what bright red and buried his face into the seat. She flipped him around and pulled the front of his panties out, he was leaking profusely out of his cage. We both took this opportunity to verbally degrade him for enjoying his punishment to the point of leaking “Awe does someone like when their ass is full” “How does that little clit make such a mess” “Does someone need a diaper bc the can’t control their messes?” He couldn’t look either of us in the eye, and he leaked more with each comment.

Kim proceeded to attach the panty liner to his panties and we allowed him to pull up his pants to get out of the car.

To be continued…