My Sex Life: Boss Pt. 02

"So are you free Monday?" I shrugged.

"Should be fine I'm done with everything."

"Good. I'm hoping my interviews tomorrow will soon fill the staff positions." I nodded. As I head for the door he called out.

"Oh, by the way I have one more instruction for you. I want you to wear this on Monday." I looked down as I caught it. I was shocked and nearly dropped it as I realized it was a g-string, white with a large red heart on the front. I looked up at him. "See you Monday." I hesitated before shoving it into my pocket. Once home I stared at it, but knew that like with getting rid of my underwear I was prepared to continue with the game.

When Monday rolled around it saw me entering the store, wearing the g-string under my pants as instructed. He grinned when he saw me.

"Let's see." Before I could react he yanked my pants down. He nodded when he saw the underwear. He stood and gestured I could pull my pants back up. "Confession time. I don't have a fetish for guys in women's underwear. I just wanted to push this as I didn't have a plan. I've been mostly improvising. Your ass just looked so inviting when I saw you stuck the other day." I groaned, but didn't speak. "However I do have good news. I should have people for the rest of the week and after that everything should be in place." The day proved about like before, including the relatively slow business and him wanting me to blow him while he dealt with customers. However this time when he came back from turning the sign to closed he sat in a chair, holding his cock up.

"Hop on." I stared a moment before straddling and slowly lowering myself onto him. "Is this a first?" I shook my head.

"Same girlfriend." He whistled before laughing softly. Continuing to lowering myself I was sitting on the head, both of us pushing. In a short time the head popped in and I groaned in some pain. However I was soon lowering myself into his lap. To my surprise he leaned into kiss me. It was different from the women I had kissed, although they tended to be more aggressive than him.

Then I slowly raised myself to begin riding him. It was a bit awkward as riding someone in a chair doesn't work as well as in a bed as you have to push yourself up more. I moaned as I lowered myself once again and held onto him for support. He gripped my hips and grunted as he stared to thrust upward to meet my downward thrust. In and out, up and down I continued to ride him in jerky, awkward motions that I never managed to smooth out. I moaned and felt him swell inside me as I began to swell as before.

It was only after I been riding for a while that I realized he had neglected to put a condom on me. However when I tried to slow and point this out he suddenly slammed into me. I cried out as I came on his chest and stomach. He thrust for a short time before he stopped grinning.

"Clean me up." I awkwardly dropped to my knees to lower my head to his chest and stomach. I extended my tongue to begin licking over his chest and stomach. This was a first as I had never actually cum on anyone before. When he was satisfied that I cleaned up my cum he spoke.

"Bend over." I awkwardly complied and rose to my feet to bend over the chair. He easily slid into me eliciting further moans. In a short time he was slamming into me with hard, fast thrusts and I gripped the chair tightly. Without warning he suddenly stopped to pull back and make a hard thrust, followed by a series of increasingly shallow thrusts until he pulled out. At that point I was too winded to move, but soon I was uncertain about moving as he had cum in me. However I did not have long before I felt him at my ass, pushing in a plug.

"Keep that in there until you get home." I nodded as I struggled to keep it in until I had dressed, including the g-string. As the day progressed I occasionally felt the plug shift, but soon my ass had closed to the point where it remained still. However I never forgot it was there.

This set a pattern even though I only worked at the shop a few more times. We never dated, but we would meet a lot and have sex over the course of the following three months. I kept the panties, although I didn't wear them after that. This would not be my last time with a guy and I would see Veronica again, but those are other stories.

The End