I tossed and turned all night, having a hard time sleeping. Nolan’s letter and offer were on my mind all night long. Should I go through with what he wanted? The perks of the deal sounded great, and I had no reason so far not to trust Nolan or Bree.
Nolan was obviously bi. He seemed to certainly enjoy sucking my cock, and to be honest, it felt great to me. Was I bi? Would I be expected to suck Nolan in return? Was the butt plug meant to indicate that at some point, Nolan would want to fuck me?
At the same time, any playtime with Bree sounded exciting to me as well. Hell, if giving pleasure to Nolan meant that I would get some fun time and pleasure with Bree, it might be worth it. Hell, I’m willing to try anything twice.
I thought that I was ready for the big city, but I never expected a situation like this.
My light sleep was interrupted Sunday morning by my cell phone ringing.
Being only half awake, I answered it groggily with a ‘hello.’
“Charlie, this is Bree. I’ll be at your apartment in fifteen minutes. I’m sure you’re already up, and you’ve taken a shower and had breakfast. Grab your clothes for work tomorrow and bring them with you because you’re going to spend the night at the house with me tonight. Nolan had to fly out to Los Angeles this morning. But anyway, I will see you in fifteen minutes. Make sure you’re showered, dressed, and ready. I’ll be parked in front of your apartment, just come out and make sure that you’re not late.”
The line went dead. I was suddenly wide awake. As I leaped out of bed and ran to the bathroom, I shouted, “Oh fuck!”
My heart was pounding. I frantically jumped into the shower, not really caring that the water needed a short time to warm up. I think it was the quickest shower ever. I threw a t-shirt on that stuck to my half-dried off body. Underwear and shorts, socks. I didn’t even tie my sneakers.
I grabbed a dress shirt, tie, and pants for Monday’s work and ran outside, where Bree was in her car already waiting for me.
I was breathing heavily as I opened the car door.
“You’re five minutes late, Charlie.” Her tone was casual, just simply stating a fact.
While trying to catch my breath, I uttered, “I’m so sorry, Bree.”
Bree simply patted my knee and said, “Don’t worry, we’ll fix that, and I’m sure you’ll do better next time, but we’ll have some fun today.”
With that, Bree hit the gas pedal, and we were on our way to Nolan’s house.
I was nervous about the sudden change in plans, and Bree gave no hint of what we would be doing. In fact, we didn’t talk at all for the whole ride, but it wasn’t that long of a drive. I simply sat back in the seat with my eyes closed, trying to let my pulse return to normal while taking in the sweet smell of Bree’s fragrance. All I could think of was watching Nolan and Bree having sensual, passionate sex as I was restrained and helpless. My cock was stirring in my pants.
Soon enough, we pulled into the long driveway and up to the large house. As we walked in the door, Bree turned and, with a stern voice, explained, “Unless otherwise told, whenever you walk into this house, you will strip immediately and place your clothes on the side table next to the front door.”
I was surprised, and I obviously didn’t move fast enough because Bree let out a loud “Now, Charlie, you need to strip as soon as you enter this house!”
Startled, yes, but I didn’t waste any time stripping right there as quickly as I could.
I was learning quickly that when Bree said to do something, it was wise not to question, but just do the task as quickly as possible.
Her next order wasn’t as loud, but still stern. “Fold your clothes neatly and put them on top of the table.”
I was quicker this time as I followed her command.
“Follow me, Charlie.” This time, her voice was more casual, but I wasn’t going to take any chances and followed her direction without hesitation.
She led me into the living room and pulled out an armless wooden chair away from the wall, and Bree sat down on it. “Come closer, Charlie, so I can remove your cock cage.” It was music to my ears. I wanted to say “Thank God,” but decided it would be better to just keep my big mouth shut. I was learning.
As Bree finished removing the cock cage, I let out a sigh of relief. It really felt so much better having my cock free. My cock certainly agreed because it started to twitch and become half-aroused as I stood there looking at Bree. Her auburn hair and her sexy body.
Since she was sitting down, my cock was about eye level with her. I so wanted her to open her mouth and start sucking me. To feel those lips around my best friend would be so exquisite. I so wanted her hands to feel and play with my balls, and then for her to stroke my cock to its full hardness, and for her to finally beg me to fuck her.
I was jolted out of my daydream when I heard Bree issue her next command. “Lean over my lap, Charlie.” I knew that it wasn’t a question or a suggestion.
I’m bent over, my cock dangling between her legs, my arms stretched out with my hands against the floor, and my bare ass up in the air.
Bree starts to gently rub my ass, and then she lowers her hand to massage my balls that are dangling down. Sure, it feels good, but I’m not sure that I’m going to like this.
“Tell me, Charlie, how many minutes did you make me wait for you outside of your apartment this morning?”
I mumbled, “Five minutes.”
I suddenly received a hard smack with her open, bare hand on my left ass cheek. “I didn’t hear you, Charlie! When you’re asked a question in this house, you answer in a clear voice because mumbling isn’t allowed!”
In a much louder voice, I replied, “Five minutes, I was five minutes late, Bree.”
“I’m not deaf, and never raise your voice to anyone in this house. Also, at work, I’m Bree, but in this house, or when we are alone, I’m Ma’am. Do you understand?”
“Yes, ma’am. I was five minutes late, making you wait for me this morning, Ma’am.”
I received five rather hard smacks on alternating ass checks. I had never received a spanking in my entire life before. I’m not sure exactly how I felt. I was partly embarrassed but also excited at the same time.
“Stand up, Charlie.”
The excitement didn’t go unnoticed by Bree. “Well, Charlie, I see that your cock is rock hard. Just remember, I went easy on you this time. In the future, any punishments will be harder.”
I didn’t take that last comment as just a mere threat but understood that it was a promise. How much harder would punishments be? Would I be able to handle whatever Bree or Nolan had in mind?
What have I gotten myself into was all that kept going through my mind, but the only thing that came out of my mouth was, “Yes, Ma’am.”
Being naked and over her lap with her touching me was so erotic. I kept thinking of her telling me in the past that pain needs to come before pleasure. I think I was getting some of both at the same time.
Bree stood up. “Put the chair back against the wall and follow me.” She led me over to a door, stopped, and turned to face me. “Every area on this property is a play area, but this door leads down to the real playroom. You will only go downstairs to the playroom if instructed to do so. Is that clear?”
“Yes, ma’am.”
“Good, because your real training starts now. Come with me.” With that, she opened the door and turned the light switch on, and I followed her down to the basement, or what she called the ‘play room’.
It was a large room with plenty of open space. In the middle of the room sat what Bree explained was an anal training bench. A bench with various-sized dildos spaced apart from each other. I suddenly understood what Bree meant about starting my training.
I wasn’t expecting this. Should I turn and run up the stairs now?
I think Bree sensed my apprehension, because she turned to me and slowly started to rub and stroke my cock while leaning into me and whispering in my ear, “Do you trust me, Charlie?”
I looked at the bench. The dildos started small but soon became rather large. How the fuck could I ever take all of those? I knew that there was no way in hell that I could, but Bree was stroking my steel like, hard cock. What choice did I have? I took a deep breath and answered her, “Yes, ma’am, I trust you.”
It was my cock talking, not my brain. There was no doubt about that.
She pointed to a tube of lube and pointed to the first dildo. “Go ahead, lube the first one and then straddle the bench, and I’ll ease you down.”
I’m not sure if I was even thinking at this point, but simply following her commands.
Bree got behind me and guided me down on the first dildo. To be honest, it wasn’t that difficult. It gave me a strange sensation. Not a bad feeling once it pushed through my entrance.
“Bounce up and down on it while keeping it still in your ass.”
The sensation of the dildo and my movement of going up and down kept my cock hard.
Bree kissed the back of my neck and whispered, “Lube the next one, Charlie.”
One down and five more to go.
The next one was taller and thicker than the first one. Bree guided my hole directly over the plug as I inhaled and slowly lowered myself onto it. This one I had to take my time with, but I had to stop halfway down. It was stretching my hole. It wasn’t going in as easily as the first.
“Slowly raise yourself slightly and then lower yourself back down, letting yourself get used to the dildo and go lower. Keep doing that.”
I wasn’t sure if it was simply a helpful suggestion or if it was one more of Bree’s commands. Either way, I did as I was told, and I slowly let my own weight sink more of the dildo into my widening hole.
Once again, Bree kissed the back of my neck and whispered, “Lube the next one, Charlie.”
The next dildo was even bigger in size. I hesitated, being unsure of myself. I just couldn’t. I knew it was going to hurt even more than the ones so far. It was too big, and my hole just wasn’t used to doing this.
I heard from behind me, “Next!” This was, without question, a command. An expectation that wasn’t up for debate or discussion.
After using plenty of lube, I positioned myself once again and inhaled deeply. I slowly started to descend on the plug. It was stretching my hole like never before. The pain and uncomfortableness was hard. What wasn’t hard anymore was my cock.
I kept shaking my head while wondering if this was really worth it.
Bree whispered once again into my ear. A gentle voice this time. “Charlie, I know this is hard, but I know you can do this. It will take time, practice, and patience, but if you complete this dildo, we won’t do any more training or punishments for the rest of the afternoon and evening. Actually, I have a very exciting surprise for you.”
My heart was pounding in my chest. I took a deep inhale and slowly continued.
It seemed like an hour, but it was probably only about a span of five minutes. My ass finally rested on the bench with the dildo fully inserted all the way in.
Bree wrapped her arms around me from behind. I could feel her hard nipples and tits pressed into my back through her lightweight blouse. She held me tight. My ass was burning, but it didn’t matter. I was an 18-year-old virgin, and I had my sexy and gorgeous boss wrapped around me. She started to stroke my cock again, which came back to life extremely quickly.
She finally let go of me and stood up. “You may stand up now.”
I discovered that coming out was only slightly easier than going in. As I finally was able to stand up, I tried to turn away from Bree as I wiped a few tears from my eyes. She simply hugged me again and held me tight.
Finally, which was all too short a time, she pulled away and simply said, “It’s time to go back upstairs, Charlie.”
As we started walking up the stairs, Bree asked, “Charlie, are you ready for the surprise that I have planned for you now?”
