I rode with Sally to Jill’s work, which was about a 20-minute ride. Once I entered the building, the event was taking place in the lobby of the building. I was surprised at how big the company was. All Jill told me was she worked for a company that did major event planning for large companies.
Apparently, by the congratulation signs, her division had landed a large company that put on many events. Since the celebration was now drawing to an end, everyone seemed quite happy and most of the food was gone.
I asked a few people about where I could find Jill, and I guess they knew I would be arriving late. Most of the people responded with something like, “You must be Clyde. Jill was hoping you would have been here a lot sooner to help her celebrate.”
Finally I did find where Jill was standing, talking to two other women. “Clyde, I am happy you finally made it. This is my boss June, and one of my co-workers Alice.”
“Glad to meet both of you,” I said.
“You know you really embarrassed Jill by coming so late,” June said.
“I know that and I apologize,” I said.
“So Clyde, were you spanked by Sally before you came here?” Jill asked.
Now I was embarrassed to have Jill talking about my spanking in front of her boss and co-worker.
“Go ahead and answer Jill,” June, her boss said. “Jill has told us all about you.”
Now I was even more embarrassed. “Yes, Sally gave me a severe spanking before she drove me over here.”
“Good! I hope you never embarrass me again.” Jill said.
Then we talked about me dating Jill and also about the company celebration. It gave me even more respect for what Jill does in her line of work, and also how powerful Jill is within her company.
Before we left June and Alice to talk to Jill’s other company friends, Alice said, “Bye for now. We hope to see you again at the end of the party.”
Jill next introduced me to the other people at the party. All of them were very friendly and many mentioned that I had missed out on Jill’s celebration. I got to eat the few bits of food that was left over and have a drink.
After a lot of the people had left the party and the party was winding down, Jill took me back to where June and Alice were standing. “Before Clyde and I leave, I want to show him my office. Can you come along too?” Jill asked.
“Yes, we would be delighted to,” both June and Alice answered.
Then we took the elevator to the tenth floor. First I was shown June’s large office, then Alice’s office and finally Jill’s. The office had nice large windows and it had a door for privacy. I was pleased to see a picture of Jill and myself on her desk. After all three of us were in Jill’s office, Jill closed her office door.
“Clyde, I would like to make sure Sally did a good job in spanking you. Stand in front of me with your hands on your head so I can inspect you,” Jill said.
“But June and Alice are in the room. Can’t we do this alone? This is so embarrassing,” I said.
“You have embarrassed Jill by showing up so late. Now you deserve to be embarrassed,” June said.
So I stood in front of Jill with my hands on my head. First, she pulled out my shirttails and rolled them up so they were out of the way. Then my belt was unbuckled, I was unzipped and my pants were at my ankles. While this was going on I didn’t make eye contact with Alice or June, I just looked straightforward. Next, my undershorts were at my ankles and Jill said, “Step out of your clothes so I can get them out of the way.”
While Jill handed my clothes to Alice, I obediently stood with my legs spread wide. June said, “What you told us is true, Clyde does have his pubic hair shaved.”
“Yes, I told him he better shave down there, if he wants to keep dating me,” Jill said.
Standing naked from the waist down in front of women I had just met was quite embarrassing, but I still had an erection.
“Clyde, now I want you to go over to my desk and bend over it, so we can examine the results of the spanking you received from Sally,” Jill said.
So I went over to the desk, bent over it and grabbed the other side of it with my hands. I also didn’t want to, but I spread my legs like how Jill likes me to be. Now I felt many hands on my sensitive bare bottom.
“Sally did do a good job in spanking him. I also like that his bottom is shaved. It feels so smooth and nice,” June said.
“I wonder if my boyfriend would shave his pubic area for me, so he would look like Clyde,” Alice said. “I have never spanked a man before. Would you allow me to spank Clyde?”
“He just had a severe spanking from Sally, but if you were to give him a light hand spanking, that would be okay with me. Why don’t you sit on a chair and have him lie over your lap?” Jill said.
“Yes, that sounds like a very good idea,” Alice said.
“Since you are wearing a nice new dress, you should probably take it off so Clyde doesn’t accidently mess it up,” Jill said.
I heard some rustling of clothes behind me and then Jill said, “Clyde, stand up and take off your shirt and tie, then go over to Alice and ask her to spank you.”
Now I was almost totally naked before the three women, with only my shoes and socks on. When I finally looked over at Alice, she was wearing a very skimpy flesh colored bra and panties. She also had on a garter belt that held up her hose, which ended on her upper thighs. With Alice being about my same age, smelling her perfume and seeing how she was now dressed gave me a full-blown erection.
I finally got up the nerve to stand in front of her with my hands on my head and say, “Alice, will you please spank me?”
“I would be happy to,” Alice said. “But first I want to examine how well you are shaved.”
I was now even more embarrassed and I looked over at Jill. “Clyde, make it easier for Alice to examine you by spreading your legs some more,” Jill said.
I really didn’t want to, but I spread my legs some more as I felt Alice’s soft fingers on my penis, balls, and on my bare pubic area. “I like the way he looks when he is shaved. So Clyde, lie over my lap for a quick spanking.”
I reluctantly bent over her lap and presented my sensitive bottom for another spanking. My penis was now between her thighs, rubbing against her bare skin and her nylons. Although she was just spanking me with her hand, I could really feel it.
As I was being spanked, June said, “I would like to spank Clyde too. I felt he really embarrassed you, so he should be embarrassed with a spanking from me.”
“As soon as you are thru spanking Clyde,” Jill said, “Have Clyde stand up and you can trade places with June.”
After awhile, Alice finally said, “Stand up so that June can spank you.”
When I stood up, I put my hands on my head and spread my legs. I didn’t know when June took off her dress, but she was now in her bra and panties. I was examined again and then I lay over June’s lap. Luckily for me, her hand spanking did not last long. But when I stood up, I still had my erection.
June said, “Since Clyde still has an erection, can I embarrass him again by milking him?”
“You're my boss. Go ahead. He deserves it,” Jill said. “Let me grab some tissues for you.”
Then I had to stand still while June stroked my penis and I exploded in her hands. Now both my bottom and my front side were very sensitive. Finally, I was allowed to get dressed and Jill drove me back to her house. Since it was so late, I didn’t go into her house, but drove straight home.
But before I got out of Jill’s car, she said, “Now you know what to expect if you embarrass me again in front of my friends and co-workers. Also, June and Alice really liked you, and they hope to see you now and then, especially for company events. I am looking forward to having more dates with you.”
Now I know never to disappoint Jill again.
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