Becky's Tease Ch. 03

Story Info
Becky takes Barry to new submissive level at home & on vacation.
13.4k words
4.42
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14

Part 3 of the 4 part series

Updated 01/29/2024
Created 10/06/2022
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I was on top of the world and I loved it.

Summer had come which brought lots of changes in my life. Barry graduated college and decided to stay in town. Pete, his housemate, left and I moved in. It was both a relational and financial arrangement.

I met Barry's family at his graduation. They were classic underachievers. Both were retired and seemed to be in their early 50s though I couldn't be sure. Barry's paternal grandfather was a renowned businessman who wrote some of the early management books. We had read his most famous book in one of my early business classes. My professor called it dated but important and advised us to look past some of the earlier business practices and glean the parts about how good business people can grow in their company as they push for the business's success. I enjoyed the book but agreed with my professor. It was a bit dated.

The book made a bunch of money for Barry's grandpa and that money was handed down to his father who most likely never read the book because he had never moved beyond middle management in a somewhat outdated company. He enjoyed spending money more than making it. Barry's mother read a different book. It might have been titled, "How to Marry a Man with Money." She was also a good spender.

At dinner that night, I told Barry's dad that I had read his father's book in one of my classes and he offered to have the book signed for me. I didn't have the heart to tell him that the book was probably sitting in the used bookstore hoping that some other professor might one day assign it to his students.

Barry was following in his parent's footsteps by taking on a mediocre job working at the front desk of a large office building. His parents were proud that he had landed a job before graduation and encouraged him to be the best desk officer he could be. Dad talked about the importance of keeping a balance between security and hospitality, pointing out how the first impression of a company was so important but bad players getting into a building could lead to stolen work.

I quietly shook my head. Barry's job was to check IDs and give parking vouchers to the few visitors who did appear at the door. I didn't tell his parents that his position would most likely be replaced by an electronic gate and a parking kiosk.

While Barry was doing his security/hospitality work at the front desk, I was doing a paid summer internship in the Marketing Department of a tech company not far from his work. As a Marketing major, it was the perfect job for me and I loved it from the moment I started. My manager valued my opinions on what people my age were looking for when using their apps. And better yet I was being paid good money.

I was making more money in my internship than Barry which was the financial reason for my moving in with him. The poor boy couldn't afford half of the monthly rent. With my paycheck, I was able to keep us in the apartment.

As I said before, our living arrangement was both financial and relational. Before graduation, I stayed at his place maybe one or two nights a week, and most of those nights Peter was around so, due to the thin walls, our lovemaking was forced to be very quiet or nonexistent. Now that we had the place to ourselves we were able to do whatever we wanted, whenever we wanted to do it. Life was good.

Barry and I not only enjoyed having sex; we also entertained ourselves with fantasy talk. I quickly learned that Barry was even more submissive than I thought. Our evening with Paul, whom Barry still referred to only as Sex Guy, was a big thing for him. He loved to talk about Paul and often asked me what sex was like with him. He always wanted more details so I didn't hold back. I never compared the two of them and he never asked me to. This was a good thing because if I was forced to pick based only on the quality of the fuck, Paul would win hands down.

Our talk about Sex Guy almost always ended in us having sex. I think perhaps Barry saw it as him winning in the end. He knew that my sex was good with Paul but at that moment he was the one who had me in his arms. I was ok with this. I did find that, while I liked being on the bottom with Paul, I preferred to be on top of Barry. Paul was strong and forceful. Having him on top pushing himself on me was thrilling. With Barry, I wanted to be in control. I liked to start out straddling Barry on his chest. From there, I had many options. I could move forward, push my knees into his underarms, and force his hands above his head, putting him in a surrender position with my clit on his mouth. Or I could also move back and lean forward placing my breasts in his mouth.

And of course, I could go further back if I chose and impale myself on his dick. Barry didn't have much choice in the matter being stuck under me the whole time. If I let him fuck me, it went at my speed and ended when I wanted it to. Sometimes that was before he had a chance to come and if that was the case the poor frustrated boy would just have to wait. I always went to sleep completely satisfied having felt his tongue between my legs whether we fucked or not.

Early in our time living together Barry, in his shy way, asked me about spankings.

"I've been thinking," he started one night. I had just rolled off him with both of us having happy endings.

When he didn't finish his sentence I had to ask, "What were you thinking, Barry?"

"Well, Um." The boy took so long to get around to his deep dark issues. "Well, would you ever consider giving me a spanking?"

I laughed out loud. Big mistake. I should have taken his desires seriously.

"Never mind," he muttered, rolling over away from me.

"No no I'm sorry Barry," I said as seriously as possible. "Why do you want a spanking?"

"I feel like I need to be punished," he admitted.

"Why? Have you done something wrong?"

"I don't know. I mean I don't think I have but I think about being punished a lot and it turns me on. You know, the same way I feel when you are doing it with Sex Guy."

"Ok then, you will get a spanking but not tonight. It has to be when I decide." Barry rolled back toward me, hugged me, and happily went to sleep.

It was a few days later when I decided it was time for his spanking. I had never thought much about spankings as a sexual thing but it was another way for me to control Barry and I liked that thought.

After dinner, we were watching TV when in the middle of a show I told Barry to go to his room and prepare for a spanking. He gave me a shocked look.

"Now?" he asked.

"Yes, now. I told you it would be when I decided. I decided it is now."

"Can we finish the show?"

"No!" I said strongly. "To your room and prepare for your spanking."

"How do I prepare for a spanking?"

I hadn't thought about that. I thought about telling him to take off all his clothes but then it sounded too sexual. I wanted it to feel like a punishment.

"Just go to the bedroom, sit on the bed, and wait for me."

"Yes, Ma'am," he responded. And then, as he walked toward the room, "Can you record the rest of the show?"

"No!" I responded right away. I recorded it anyway. I also wanted to see it.

I let him sit there for about five minutes and then walked into the room where I found him meekly sitting on the bed.

"OK, you wanted this and you're going to get what you asked for," I said as I pulled out the desk chair and sat in front of him. "And as a further punishment, there will be no sex tonight."

Barry looked at me but didn't say anything. He was pouting like a baby.

"Now stand up, pull down your pants and your underwear and get over my lap."

He stood and stripped down. I could immediately see his erection. "Umm, go in the bathroom and get a towel. I don't want you spewing your seed all over my jeans. That is not what this is about."

Without a word, he did a duck walk to the bathroom while holding his pants around his knees. He looked pretty silly as he came back holding the towel with one hand and the top of his pants with the other.

Once I got the towel over my lap I was able to comfortably pull Barry over my knees. His hands went to the floor on my left and his feet were hanging in the air to my right. I placed my palm on his bare butt and prepared for a spanking.

I had never given anyone a spanking before and had no idea what I was doing. It seemed pretty simple though. I raised my hand and let it come down hard in the middle of his butt. Barry's head flew up immediately.

"Ah, Shit! That was too hard," he cried.

I didn't know what to do. I didn't want him controlling this but I also was doing it for him. I certainly didn't want to hurt the boy but at the same time, this was supposed to be a punishment. As a result, my spanks went from hard to light to hard again.

This just wasn't working and both of us knew it. In the end, I told him I had recorded our show. We went out and watched and then, breaking my threat from earlier we went to bed and had sex.

***

This was the first time that I lived in a place other than the dormitory or my parent's house and I wanted to host a party. I had been making some new friends at work and I decided to have brunch for a few of them. I invited three girls from my team. Two of them had boyfriends who were also invited so along with Barry and me there would be seven of us.

The night before my big event, Barry cooked our dinner while I did some preparations for the brunch. Together we made a total mess out of the kitchen. I was tired from a busy day of work and an evening of planning so I appreciated it when Barry offered to clean the kitchen and let me go to bed.

Barry was still asleep when I got up in the morning and I figured I wouldn't wake him as all I had to do was put the coffee cake and casserole in the oven.

"Shit!" I yelled when I turned on the kitchen light. That was followed by "Barry!!!"

Silence.

"Barry, get up now" I screamed walking back into the bedroom.

I found Barry in our room half asleep and struggling to put his jeans on. "What's the matter?" he asked in response to my panicked call

"The kitchen," I screamed. "It is a total mess. You said you were going to clean it up for me last night. What the fuck happened?"

"Oh shit. I fell asleep on the couch. I must have woken up in the middle of the night and just crawled into bed."

"We gotta get this place cleaned up before my people arrive. And we have to make coffee, tea, set the table, neaten up the living room...." I was manically listing off things to do in no particular order.

When Barry cooks he has a way of using every bowl and utensil in our house and last night was no exception. The sink was full of plates and bowls. Pots and pans with caked-on food sat uneasily on the stovetop. Even the floor was covered with crumbs that had flown around during his cooking event.

It took us a full hour to get the apartment back in order and another twenty minutes to neaten up the rest of the apartment. At that point, I was almost too tired to have the party. I was also still angry with Barry.

"Barry..." I started in a rather harsh voice.

"I know. I know. I'm sorry Becky."

"No, listen to me," I responded in a firm tone. "You. Into our room now! Get out your towel, move the desk chair next to the bed, and wait for me. I need a few minutes to cool down."

Barry knew I was upset and was happy to get away from me. He also knew what was going to happen next. Our first spanking session had been a fiasco and I knew why. There had been no reason for it. This time it would be different.

Even though I was never spanked or even given any punishments, there was one rule that I remember from growing up. 'Never punish in anger.' Well, that might not work today, I thought. Although I did count to 10 before heading toward the room.

Halfway to the door I turned around and went back into the kitchen. I grabbed our largest wooden spook before heading back to the room.

I found Barry sitting on the bed with his hands in his lap. The same towel we had used during our previous poorly managed spanking was folded neatly beside him and the desk chair was in front of him waiting for me to sit.

As I sat down facing him, still holding the wooden spoon, I saw a bit of fear in his eyes.

"This time it's real. Isn't it?"

"Yes, Barry, this time it's real. I figured out why our last spanking session didn't take. This time you screwed up and need to be punished."

Barry just stared at me. I think he was unsure about what he should say so he said nothing.

"We don't have much time," I continued. "People are coming soon and I still need to get dressed. Pants and undies down and get over my lap."

Barry stood, placed the towel over my lap, then pulled down his pants and got in position.

I placed the spoon on the floor next to my chair and started with my hand. I spanked him lightly at first then picked up both the force and the tempo. His suddenly unsteady breath and the bucking of his feet told me that I was hitting my mark. As I reached down for the large wooden spoon I noticed that his butt had turned a crimson red. Touching it I noticed that the skin was quite warm.

I didn't have much time so and I still wanted to make more of an impact on him so I started in hard with the spoon which brought cries of pain to Barry's lips. I saw that the spoon was leaving nice round marks on his bottom. I was sure that they were going to be black and blue. That and the fact that he was now fully crying and begging me to stop made me think that I might have gone a little too hard.

"I thought this was what you wanted," I said when he started complaining through his tears.

"I-I did," He responded between his harried breaths. "I just didn't think it would hurt so much"

"Ten more and then we are done for now. We have to get ready for our party"

Without me asking Barry counted each of the ten strokes from the wooden spoon. By the end, his cries made it difficult to hear his counting.

"Get up and pull up those pants"

"Yes, ma'am," he responded tearfully.

"I want you to go out and set the table then wait for the guests to arrive. I'm going to jump in the shower."

"Yes, ma'am"

"Oh and set the table for six," I added as I stepped into the bathroom.

"But there are seven of us"

"I know. I think you may not want to sit with us -- Or sit at all! You can be our waiter today."

Barry didn't respond to that. I don't know how he felt. He was probably relieved that he didn't have to place his butt on the wooden chairs in our dining room but he may have also been thinking that he was going to be looking a little silly not eating with everyone.

I stripped down and hopped in the shower being careful not to get my hair wet as I wouldn't have time to dry it. While soaping myself up, my fingers slid down between my legs. I hadn't realized how much that spanking turned me on. As I rubbed myself the fantasy part of my brain fired up.

At first, I was remembering the spanking and especially that moment when Barry's ragged breathing turned into cries -- how he was begging me to stop. And then I started thinking about Barry in pain in front of our guests. I imagined that they all learned that he had been spanked hard with a wooden spoon just before they arrived. In my mind I saw Barry, his face red with humiliation, and unable to look up from the floor as my guests stared at him in disbelief. With all that going on in my head and my fingers pressing into my clit, a completely pleasurable orgasm erupted causing me to lean against the shower wall for balance. I shook my head as I turned off the water. I hadn't expected that. Once again I realized how much I enjoyed controlling Barry.

While drying myself off I heard our doorbell and knew that Barry would be welcoming our first guests. It turned out to be Mary, our guest who was coming alone. Mary Teller was my best friend at work. I liked the other girls enough but Mary and I were particularly close. We ate lunch together almost every day and confided in everything -- well, almost everything.

I had recently told Mary about my one-night stand. (She was the only one other than Barry that I had told.) But I had not told her about my second time with him where Barry was forced to sit and watch. That was too much to share and it wouldn't be fair to Barry if she ever met him, which she was doing at this very moment.

Mary was an extremely pretty girl who always dressed well. When the rest of us were wearing pants to work she would be in a skirt or dress that showed off her amazing legs. She had small breasts but she always showed them off nicely, often with tight tops.

As soon as I made it out to the living room. I saw that Barry was gaga over her. The tears from his spanking had seemingly washed away and he was happily talking with Mary.

I noticed that Barry had changed his pants. Instead of the tight pair of jeans that he had on earlier, he was now wearing some baggy pants. I had never seen them before and they didn't look very good on him. I guessed that the boy's bottom was still hurting.

Mary was dressed in her usual fashion wearing a short skirt and a tight top. It was immediately obvious that she wasn't wearing a bra. I was sure that Barry had noticed as well.

"Barry, did you offer Mary a coffee?" I asked sternly. Barry looked up embarrassed that I was so demanding in front of Mary. I decided to push him further. "And before you get the coffee I want you out of those ugly baggy pants. Go put on your black jeans and a clean white shirt."

"But those pants are tight," Barry responded in a quiet voice. He didn't want Mary to hear about problems with his butt.

"They will be fine," I responded in a voice loud enough for Mary to hear. "I know your bottom hurts but it is important that you look nice today."

Barry's mouth dropped open. He didn't like being ordered around but worse he was shocked that I had commented on the state of his rear in front of this beautiful girl.

To be honest I was also surprised by what I said. I hadn't planned it but it felt powerful to say it in front of my friend.

Mary gave me a knowing smile as Barry sulked toward our bedroom.

"Welcome," I said. "I'm sorry Barry didn't offer you something when you arrived."

"Oh, that's fine. Guys don't always think of things like that," replied Mary.

"I'm working on him. I have to give him some correction from time to time."

"It sounds like you gave him some 'correction' this morning." She said with a sexy smile.

Barry was returning with coffee wearing a white dress shirt and tight black jeans. He looked the part that I wanted him to play. He would have been correct if he had guessed that we were talking about him while he was away. I had spent our alone time filling Mary in on more of the secrets of our relationship.

Soon the two couples arrived and both Barry and I were surprised to see one of Barry's basketball buddies come in. It turned out he was the boyfriend of one of my coworkers.

Barry played pick-up basketball almost every weekend. It was a group of students and recent graduates who were just out to have some fun on the courts.

I now had a decision to make. I planned to order Barry around like a servant at brunch. The idea had come to me after the spanking when it was making me hot to think about punishing and humiliating him.

I looked at the table which was set for six just as I had asked. Should I change my plan now that one of his friends was here? I looked at him and decided, what the hell, let's see where this goes.

As we approached the table I saw some confusion about the seating so I announced to the group that Barry would be our waiter today.

"He is very good at this and likes to serve," I concluded. With that, I ordered him to the kitchen to bring in the coffee cake and breakfast casserole. After serving the food, I commanded him to serve coffee and tea followed by the orange juice and champagne that one of the couples brought. At one point, when some water was spilled I called for him to come quickly and clean the table and floor. When Barry appeared with what looked like a dirty rag, I yelled at him to bring out a clean one. With a "Yes Ma'am" he ran off and came back with another. I then pointed to the floor and he went to his hands and knees and crawled around at everyone's feet mopping up.