Trip to the Drug Store P6

After I was shaved and spanked at the Quick Health Center, I went home and got ready for my date with Jill. I took my time eating and getting ready, because Jill had said that this was a special date.

At 7 PM, I called Jill to ask her if I needed to stop and pick up anything. Jill answered me with, “Don’t you remember? You were supposed to be here right now. Just come over as quickly as you can.”

Now I remembered that this date had something to do with the company she worked for. I was supposed to pick her up a little before 7 PM, so that we would be there on time. Jill also was one of the organizers of the event, so she needed to be there a little early.

Now Jill lives a good thirty-minute drive from my house, so I quickly got into my car and drove straight to Jill’s house. I rang the doorbell and when the door opened, I was glad to see Sally.

“Is Jill here? I guess I was suppose to pick her up earlier,” I said.

“Come and in and I will explain what is going to happen,” Sally said.

We sat on the couch together and Sally continued, “As you know, the event was a company event that Jill helped plan, so it was important that she got there on time or a bit early. She was hoping you would accompany her, but since you forgot, she drove herself there. Jill had told everyone at her work that you would accompany her, so you really disappointed her.”

“I’m sorry. I didn’t mean to be late. I just forgot,” I replied.

“So I am suppose to spank you, and then drive you to her company event. Either that or you don’t see Jill anymore. I need to warn you, since you were so late and disappointed Jill so much, this will be a more severe spanking.”

“I am truly sorry,” I said. “Can’t you just take me there and let Jill spank me later?”

“If you want to keep dating Jill, you will need to take this severe spanking from me right now. Otherwise, you can walk out the door right now and never come back.”

“I have never been severely spanked before. What will it include?” I asked.

“I don’t want to explain to you how you will be spanked, but when I was in college, during my last year at the sorority, Jill and I were in charge of discipline. The girls we punished could take a severe spanking, so I know you can too. Also, you won’t forget this spanking for a long while. So shall we start?”

“I guess so. I really want to keep dating Jill, because I feel we have a lot in common. So what is next?”

“I will give you one last chance to walk away. Go to the kitchen and get the implements you will be spanked with. They are on the kitchen table. Bring them in here and place them on the coffee table next to the couch. After seeing them, you can also leave them in the kitchen and walk out the door and never come back.”

When I went to the kitchen, I saw paddles, straps, hairbrushes, and other stuff I couldn’t identify. It felt strange carrying out the stuff I would be spanked with.

“Good, you made the right decision. I think you and Jill make a nice couple,” Sally said. “I won’t use all of these on you, but I want to have a choice. So stand in the middle of the room and strip down to your undershorts. Then stand in front of me.”

As Sally sat on the middle of the couch and pulled up her dress, I undressed in front of her. I know she had spanked me before, but I still felt embarrassed taking off my clothes. Then I stood directly in front of Sally, and I put my hands on my head.

“What I like about you Clyde is that you are smart and you obey women. You even put your hands on your head without me telling you to do that. If you ever get tired of Jill or break up for some reason, I would like you to be my boyfriend.”

“I do really like Jill and I want to keep dating her. That is why I am accepting this spanking from you,” I said. “But if I do break up with Jill, I will keep you in mind.”

“OK. Let’s first check out your shaving job.” I felt my undershorts fall to my ankles. Next I stepped out of them and spread my legs for Sally.

She gently handled my penis and balls and said, “Yes, they did a good job shaving you. But you have an erection already, you naughty boy. I am curious to see if it goes away as you receive this severe spanking. So over my lap you go. I will warm you up with a hand spanking.”

Then my spanking began. Sally had a similar scent to her body as Jill that I liked.

Sally also had a firm grip on me, so I would stay in place.

“Remember to always spread those legs when you are spanked,” Sally said as she continued to spank me. “Also, refer to me as ‘Miss Sally’, while you are being spanked.”

I quickly spread my legs and answered with, “Yes, Miss Sally.”

As she spanked me Sally said, “I asked my former boyfriend to shave his pubic hair for me, and he didn’t do it. So I left him. Now I am without a boyfriend. So I will be hanging out with you and Jill for a while.”

“I think if a man really likes and loves a woman, he would shave his pubic hair,” I said. “It does however, make me more aware of my balls and penis.”

After spanking me for a while with her hand she said, “Your bottom has turned a nice pink color. Now I am going to spank you with the hairbrush.”

Now the hairbrush stung my bare bottom a lot more than her hand, and I began to squirm around a little.

“Clyde, I can’t have you moving about while I am spanking you. So stand up, kneel on the couch, and bend over the back of it.”

It felt good to take a short break and stand up. Sally then stood beside me and guided me into position. She even took my knees and spread them even further apart.

“I like spanking men a lot more than women, because it is easier to tell how they are reacting to the spanking. I really like the way you react, Clyde.”

I wasn’t sure how to react to her statement, so I just said, “Thank you, Miss Sally.”

“Now I will use a bigger leather paddle on you.”

This did hurt a lot more, but because I was bent over the couch, it was easier to stay in place.

“You are taking this spanking very well. I expected you to do more complaining,” Sally said.

“I have learned that I am spanked less if I don’t complain,” I said.

After about five more minutes of spanking with the paddle, Sally said, “I will now end your spanking with a special paddle. Let me show it to you.” Sally knelt down and showed me this longer wooden paddle, with large holes in it. The paddle also had strange lettering on it.

“This paddle was used at the sorority house by Jill and I. It really stings and it kept the girls in line. Now you get a chance of feeling it.”

“How many swats do I get with that paddle, Miss Sally?” I asked.

“I told you this would be a severe spanking, so I am going to spank you until your bottom turns bright red. As I said, Jill wants you to feel this spanking for many days. So do your best to hold still.”

“I am so sorry,” I said. “This will not happen again, Miss Sally.”

Then I felt the first swat from this paddle. It hurt so much that I exclaimed, “Ouch! That really hurts!”

“It is supposed to hurt. I told you this would be a severe spanking.”

Then SWAT, SWAT, SWAT, SWAT, many more times.

Now my bottom was hurting so much that I was moving about and I brought my hands back to rub my poor bottom.

“Don’t rub your bottom until I tell you to! Your spanking isn’t over with yet, so now I want you to stand up and follow me.”

Although my bottom was still hurting, she grabbed me by my erect penis and led me over to the wall. “Stand about three feet from the wall with your legs apart, and put your hands out so you are leaning against the wall.”

In this position, it was now impossible to reach back and rub my bottom. Also, my penis and balls were totally exposed.

“The women in the sorority could take a spanking like this, and you can too. So stay in position.”

Now the paddle stung my poor bottom in a different way, and it hurt even more.

My spanking continued until I was almost in tears. Then I felt her hands on my very warm and sensitive bottom.

“Your bottom is a nice red color. I think Jill will be pleased with your spanking. But stay in position.”

Sally returned with a washrag from the bathroom. “Stay still and don’t move.” Next I felt her hands on my exposed penis and balls. Even though my bottom was hurting, my erection came back with her gentle stroking, and I squirted my cum into the rag.

“That is your reward for taking such a severe spanking from me. Now get dressed so I can drive you to Jill’s event.”

I was glad that Sally gave me a pillow to sit on during the car ride.

“Now you know what to expect from either Jill or myself if you disappoint Jill again,” Sally told me.

“Don’t worry. I will be a good boy. I never want to be spanked like this again. Miss Sally.”

Then I got out of the car to attend Jill’s event where she worked.