It’s Sunday morning and I take my usual morning pee before heading downstairs. S has texted me, “Get dressed downstairs, I have some things laid out for you.” I finish up, wash my hands, brush my teeth and head downstairs. I was only wearing my collar, but I saw on the coffee table my harness. I put on my harness, and step into the dining room to find my kilt, socks, my black button up shirt, jock strap, and a butt plug with some lube. S, getting dinner ready in the crock pot, says “I have some tasks for you this morning before we do anything else.”
“Yes Ma’am,” I reply. I step into the bathroom with the lube and butt plug, applying some to the plug, and some around and inside my hole. I relaxed, slowly began to insert the plug until it was in as far as it could go. A little precum dropped out, so I caught it with my finger and licked it. I proceeded to put on my jock strap, making sure the straps didn’t twist up. Then, I put on my socks, the button up shirt, and finally my kilt. “Ok Ma’am, I’m ready,” I say.
S inspects me. She lifts my kilt, pushes on my plug, adding pressure to my prostate. I groan a little, feeling my boy bits twitch in the front. She reaches around, squeezes my bulge. I gasp a little. “Good boy. Can you get us some doughnuts from the downtown shop? Take the bus today.”
“Yes Ma’am,” I say as I grab my wallet, phone, and my hat. I put on my shoes, kiss S, and head out the door. I power walk my way to the stop, each step causing the plug to move around inside me. I’m tight enough that it stays in place, and I can feel a little bit of drippage.
I get to the stop, and it only takes three minutes for it to arrive. Since my stop is the second one, there are only a couple people on the bus. I take a few seconds to scope out a seat, finally deciding on the back seat. I didn’t think it through, because as I sat down, and the bus took off, I could feel the vibrations of the engine through my seat, since the engine is in the back. The bumpy road only enhanced the vibrations, so I was sure I was turning a bit red with embarrassment. I was feeling a lot of pleasure though.
The bus packed quickly, so I kept to my phone to distract me. Nobody said anything about my kilt, they must have thought I was going to some event downtown. I got a few looks, but that was it. Then, the bus hit one huge pothole, and my plug felt like it fucked me, I let out a gasp and a moan. I looked to see if anyone heard me, and there were a few looks, nothing else.
The bus finally arrived downtown. I went to the doughnut shop and picked up four doughnuts. When I was finished, I received a text. “While you’re downtown, could you grab a bottle of Prosecco? Thanks!” So, I walk up the street to the liquor store. At this point, I barely notice the plug inside me, but I see the occasional pedestrian staring at the kilt. I get to the store, and feeling generous, I buy two bottles of Prosecco.
I head back to the bus stop, and wait a couple minutes for the bus. I feel a small breeze building up, and realize that I should probably sit down, as I don’t want to be arrested for putting on a show. Just then, the bus arrives. As I was the next person to get on the bus, the breeze intensified, and the back of my kilt was lifted slightly. “Fuck,” I thought to myself, since I had no available hands. I swiped my card and sat closer to the front. It was the same bumpy ride back, the plug teasing my prostate, and I’m pretty sure I’ve stained my jock strap all the way through.
I get to my stop, power walk my way home. My hole is gripping on to the plug, but I can feel it starting to slip out a little. I continue my power walk to the house. I made it just in time. I got in, put the Prosecco and doughnuts down. I kiss S, and hold my plug in place. S pulls my hand away. “Did you enjoy your adventure?” She slides Her hand up my inner thigh, to my crotch. Instead of grabbing my crotch, She reaches deeper and presses on my plug. I gasp and nod with a smile, lifting my leg a little. “That bus ride was bumpy.” She felt the sticky spot on my jock strap. “I guess it was!” She laughed a bit.
S took out the bottle of Prosecco. “Open this for me.” “Yes Ma’am,” and I slowly pour it into the pitcher. She looks at me “Why are you still dressed? You’re home now.” I stop what I’m doing and immediately undress. Still wearing my collar and harness, I grab two glasses and the pitcher of mimosa and bring them to the table. I pour us glasses, and we each take a doughnut. I kneel in front of her, resting my butt on my heels to apply pressure to my plug. “Good boy,” S says to me. I smile and sip my mimosa.