Over a week after receiving the spanking in the parking lot I had been on my best behavior, my ass still hurt but was healing. The red skin had turned to purple, brown, and yellow. I liked to stare at myself in the mirror, massage my cheeks. I liked that I had been marked. I liked the sensations. It was a constant reminder of how I had misbehaved, how I had been corrected, and that I didn’t want to be spanked again at least not right away.
In that week I had gotten into a habit with Mr. Grant. It was easy because he was still working on getting his restaurant started so he had free time. We’d go out to eat, he’d order for me. We went to the park. We talked about all of the small things, meaningless things. My parents stopped expecting me home but they didn’t say anything to me. They knew I was gay. They knew he was gay. Maybe they thought he was a good influence for me.
I’d write my lines every night at the desk in his room before bed as I sat in my underwear. I did my homework after class. I had stopped smoking. I hadn’t had a drink since the party. I was on my best behavior. I had completely forgotten about my cane. I had motivation.
During that week we did little more than jerk or suck each other off. The best was when we’d cuddle next to each other on the couch where we’d play with each others dicks. It felt slightly mischievous under the blanket with his hairy arm around my side, his hand down the crotch of my tight white underwear, barely enough room to stroke me, but he always got me off and I did the same in return with my hand in his boxers. I was unsure how I would convince him to have full on sex, especially without a condom but it was good. I had no complaints.
And yet there were moments when I got bored so I joined a few online groups about spanking. It had changed my life, having someone who I was responsible to, who looked out for my best interest, had changed my life. I didn’t want to disappoint him and yet I was still unemployed.
That’s why when he asked me if I was up to a challenge to find a job I agreed. He said he had a plan and that I was to be free Friday morning. I didn’t usually have anything then so it was an easy agreement. It was ten in the morning when he drove me to the strip mall near where we lived. I was dressed in the shirt, pants, and shoes he had bought me, my hair was combed neatly and I had shaved just that morning so I was feeling pretty fresh. I could tell by the look in his eyes that he was up to something.
“There are thirty businesses here that are all open. Twenty-five of which I believe would hire you for some kind of work. I want you to go introduce yourself and ask for an application. If they seem interested and want to talk and ask you to fill it out then do so. If they don’t, then that’s okay and just bring back the form. I will be back after twelve o’clock right here in this spot to pick you up. For every business that you don’t go to I will spank you twice.”
I swallowed at the challenge because I remembered the spanking he had already given me. I clenched my butt at the thought of another one so soon.
“If you go to all of them we can go out to lunch,” he said. “And here’s ten dollars to get yourself a snack of some kind, make sure to drink water.”
I got out of the car feeling a little excited, a little stressed, but somehow it felt more of a challenge than a punishment. It was an excuse to get me out of my head, to stop thinking about my fears and do something. I had an excuse to do the thing I knew I needed to do. Instead of panic I felt courage. He pulled away from me, the drove off as I watched him I couldn’t help but smile.
My cheerfulness didn’t last long. The first place was a grocery store. I felt anxiety just approaching a cashier let alone a manager but I made myself do it. The woman said the manager was busy but gave me an application. I thanked her and went on my way. The next place was a little more subdued as it was a cell phone store. The place wasn’t busy but there was no manager around so the man there gave me another application. It went on like that for five more stores. I was starting to feel exhausted already and decided to get a bottle of water and a snack from a place where I also asked for an application. I went out to the bench in front of the store.
Collecting applications was easy, I thought, so at least I won’t get a spanking, but then I looked to the wooden bench and there was an ache in my butt so bad I had to reach back to tell myself it wasn’t real, just a memory. It wasn’t the pain itself. It was the idea of being back over his lap, the weight on my chest, and the feeling of being naked. It was the idea of being so vulnerable with him and being able to trust him not to take advantage of me. I could walk around his house in my underwear. He’d never bully me, belittle me, or haze me.
With a renewed feeling of confidence I continued my challenge. I found the next couple to be a little more interested and got to talk to the managers. But the most eager ones seemed like they would be the hardest to work for and I had my reservations about even returning the applications. The most interesting was a coffee shop that offered ‘flexible hours’ but said that the hardest shift to get was in the morning because people made the most in tips. By the end of my job hunt I was feeling pretty tired by the time I got back to where Mr. Grant had dropped me off. I had thirty applications in hand and some stories to tell about the managers I had met.
He was right there where he said he would be, and five minutes early. I got into the car, buckled up, and he began to drive. I told him that I had collected the applications and that I looked forward to filling them out and returning them. He seemed pleased by my accomplishment and said that as a reward we’d go to the mall. We made our way to the food court where he let me pick out the place to get food.
We made small talk over lunch and I thought somehow that it was over. I thought we’d go back home and I’d fill out the applications, maybe play some video games and jerk off, or else we’d watch a movie but we didn’t, I didn’t. He raised his eyebrow to me and said there was another challenge. I nodded in acceptance.
“The mall is next,” he said. “I want you to go around to at least fifteen stores and do the same thing.”
I groaned at his comment and he looked to me with a renewed seriousness. I suddenly realized just how much like a little boy I was and how much of a man he was as I thought about my reaction. He was trying to teach me responsibility and I was trying to manipulate him out of my obligations.
Collecting the fifteen was easy. The best place I thought to work was a place that sold designer eyeglasses, both prescription and nonprescription. There were two people working there and they both seemed kind of gay, at least the man did. The woman was fashionable and she could have been a lesbian. I’d never find out for sure.
When I finished my collection I texted Mr. Grant to find out where he was and he said he was waiting outside the movie theater. He asked if I wanted to see a show starting in ten minutes. I said replied, ‘sure’ before looking at my clock and estimating the time to get across the mall. It was an easy walk, though I felt pressure to be as quick as I could be. He had the tickets in hand, gave me one. I got in line behind him in front of the person who checks the tickets.
Just past the man he stopped and looked to the concession stand. Without thinking I said, “hold on let me see if they have an application” and walked away before he could say anything. I saw one person was reloading the popcorn machine and moved to her. I stepped close and asked if the theater was hiring and if I could get an application. She said they were and would get me one. I hoped I wasn’t making us too late but collecting applications started to have its own reward. Mr. Grant moved up behind me, put his arm around me in a friendly sort of way.
“Actually I was going to ask if you wanted anything,” he said.
“Oh, well, some popcorn and a drink,” I said.
When the woman came back with the application Mr. Grant signaled to her that he wanted to order. She asked him what he wanted and he ordered the date package with two drinks, one popcorn, and one box of candy. I looked at the prices and felt guilty for a moment before he said I could pick out the candy. I moved to the case, pointed to my favorite. She smiled at us as she collected everything, more when he paid. It was a knowing smile, like that she liked gay men, or that her cousin was gay, maybe an uncle. I took my drink. He took his. I grabbed the candy. He picked up the popcorn. We couldn’t help but laugh at each other as we walked away into the theater.
We were five minutes late and the previews had already started. It was easy to find a seat because there were only a few other people there and they were mostly in the front. I led him to the back of the theater where we could sit under the projector, see if ushers entered. We snacked through the rest of the previews and into the first ten minutes of the movie until we settled into our seats and everything seemed normal.
That’s when I reached over into his lap. He squirmed a little at my touch, reached to my hand. I grabbed hold of the fabric of his crotch until I could feel his dick. He moaned a little and I let out a silent laugh. I leaned to him, kissed him on the cheek and whispered for him to be quiet or he’d attract attention. I worked him through the rest of the movie. We left as soon as the credits started. I was headed for the car but he grabbed hold me at the first unused, fire exit door. He closed the door behind us. We made sure no one saw us or was following us. It seemed clear. He pulled me into a kiss with his back against the door. I sunk to my knees, pulled out his dick.
The concrete was hard on my knees, the stairwell had this weird echo effect. His dick was hard and slick. I knew his underwear was a mess and it made me smile. I started with the tip as usual, decided to make it a quick one because I couldn’t get to his balls and where we were. It was easy to get him to my throat for the first few sucks but oddly my gag reflex started to act up so I simply sat back on my feet, wiped the spit from my lips with the back of my hand and worked his dick with my other hand. It was fun to pull and squeeze it. I loved the feeling of the head of his dick just before my hand would slip over it. I moved out of the way before he had an orgasm, let the cum shoot over my shoulder and onto the floor.
He tucked himself back inside as we began to laugh. The blob of ejaculate looked like an odd spill, maybe someone would think it was spit. We checked each other over before we ran down the stairs laughing as we did. It was easy to get back to his car. When we got there I couldn’t help myself. I moved with him to the driver’s side door, pressed my body against his and we kissed again. This time he grabbed the back of my head and held me there with our tongues slipping against each other for a long time before we pulled apart and looked around to see no one else was around, no one had seen us. We laughed more as I ran around to the passenger seat.
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