THE NEW COACH CHAPTER 37 (Scott's PoV)

Scott's PoV:

Is this fine? We were talking about holding back my desire yesterday, that I shouldn't be controlled by my lust. Yet, Josephina was readily facilitating my desire instead of resisting my demand when I asked her whether I could fuck her this morning. What made her change her mind? But should I be concerned about that? Wasn’t this better for me? I put back all my worries at the moment as I'm getting absorbed in fucking the mature woman.

“Are you feeling good, Josephina?” I ask her as I pounded her in her pussy. I moved my hips back and forth as powerfully as I could. I started to regret it why my nerdy ass didn’t bother to work out more. I was already short of breath just a few minutes pounding her pussy. The only thing that kept me going was my willpower.

“Yes…Yes, I feel good. You are getting good at this, Scott.” She moaned. Josephina’s head lolled back; her reaction was more exaggerated than yesterday. Did she fake it, or am I really getting better at fucking her? I hope it’s the latter.

My cock throbbed.

“I’m getting close,” I groaned. My fingers gripped her hips.

Her body shivered. Josephina suddenly let out a yell, “No, don’t come inside.”

I was startled by her sudden yell. What’s wrong? Yesterday, she let me cum inside her. But I still complied with her request. Thankfully, I managed to pull my dick out of her pussy before I came inside her. The moment my cock came out of her pussy, I uncontrollably cum, spraying her backside with my cum.

I could hear Josephina let out a sigh. I didn’t know whether it was a relieved sigh or a frustrated sigh.

“What’s wrong?” I asked.

“Ah, I asked you to take your cock out because I want you to cum on my face, but you end up cum first as soon as you get your cock out of my pussy,” Josephina answered.

Ah, so that’s the reason why she didn't let me cum inside this time. “I'm sorry,” I apologized to her.

“No need to say sorry, Scott. I should have said it from the start instead of telling you to pull out all of a sudden. It’s my fault.”

“I should have tried to hold on,” I say to her in shame.

“There's always next time, but you are correct; you need to train your stamina and control yourself better, Scott. This applies to your mentality and down there.”

“Sorry, I don't mean to sound patronizing; I just want the best for you, Scott,” Josephina added.

“It’s okay, I’m not offended.”

Josephina smiled at me. “Well then, I’m going to clean myself first.”

The mature woman walked away from the room. I could see my cum slowly dripping from her buttocks. Honestly, I felt kind of proud looking at it. I was marking her. An alpha dog marks their territory. She’s mine. That was what I felt when looking at her cum filled hole. I felt a sense of confidence in myself once again. Not empty bravado that I always told myself, but a feeling of ‘I can do it’ for real this time. I would save my loved ones; they were mine, not Darel or Caleb.

I calmed my excited mood. It's good that my motivation was renewed because of the confidence I gained, but the thought that Josephina or other women were mine was a dangerous fantasy. Just as Josephina said, she was her own person. If they wanted to be mine, it was because of their will and consent, not because I was forcing them. I needed to be a different kind of master than Darel or Caleb. I was a better person than they were.

Throughout the day, I was trying to hold my desire to ask for ‘more’. When Josephina came back, the mature woman was no longer dressed in her casual blouse and slacks, but a sexy crop top and mini skirt that hugged her hips. Her face was caked with more bold makeup. The getup would probably suit her if she were younger. I really didn’t want to tell her that she looked like a skanky cougar. I prefer the casual and elegant Josephina, yet my body responded differently from my mind; my cock hardened when I looked at how the once elegant lady could look quite slutty.

In the evening, we gathered in the living room. Josephina was sitting beside me, and in front of us was Astrid. As she boasted, she came back to us in two days with the result of her investigation.

“So, according to my investigation, this person is probably the one you're searching for,” Astrid said as she handed me a document folder.

“Winona Mackey. She runs a bar downtown. I tried to track a connection between her and your aunt; Winona went to the same school as your aunt, she shared several classes with her, and though they were not that close, she could be considered her friend,” Astrid explained.

“A bar owner? I thought her background would be more special as Aunt Gail said she could help me.”

“I think I know why your aunt told you that Winona might be able to help you in your case. But I will withhold that information until you do your part of the deal,” Astrid replied.

The deal. Right, I had agreed to free Astrid’s acquaintance from Darel’s influence. Previously, I doubted whether I could do it, but now I see it as a good chance: if I could save them from Darel’s influence, I could save others. If I couldn’t save them, I didn't have the right to talk about saving Mom, Aunt Gail, Raven, and others.

“So, when will you arrange the meeting?” I asked Astrid.

“It won’t be a problem if I bring you to meet them in two days, right?”

I nodded. “It's okay.”

The tense atmosphere vanished as we finished our plan. In two days, Astrid would arrange for me to meet with Mrs. A and her daughter privately.

Astrid smiled at us and said, “See you in two days, Mr. Robinson. Enjoy your day with Josephina. You don’t need to accompany me to the door, Josephina.”

Did she notice what Josephina and I did? While we were talking, Josephina, who sat beside me, was actually giving me a handjob. Thankfully, our lower bodies were obscured by the table, so Astrid shouldn’t be able to see what Josephina did with her hand. At least that's what I believe. But considering how Josephina dressed right now, Astrid might be able to tell that something was happening between us.

I was trying to keep my calm to not arouse Astrid’s suspicion during our talk by talking and behaving as normally as possible.

Josephina had told me beforehand that this was a training to hold back my desire. The goal was not to be found out and embarrass myself in front of Astrid, so I needed to hold back from cumming until she left.

The thrill of being caught pumped my adrenaline and made the situation feel hotter. This might be how some of those freak exhibitionists felt. I’m ashamed that I felt the same excitement in this situation.

Josephina was skillful in her handjob, but it seemed that she was going easy on me. She was able to tell whether I was about to cum and would pause stroking my cock for a few moments to deny me the release, and kept me on edge. It happened a few times until my talk with Astrid finished.

As Astrid left, I let out a relieved sigh. I managed to achieve my goal of not cumming in front of the indian private investigator

“Congratulations, Scott, you managed to hold on without cumming, so, as a reward, let me serve you.”

Josephina slipped down under the table.

“Try not to cum so fast, Master,” Josephina reminded me in a teasing tone.

Instead of continuing with her handjob, Josephina was giving me a blowjob. She readily put my cock into her eager mouth. I could feel her tongue dancing around my cock.

Unfortunately, despite her reminding me not to cum quickly, I was already on the edge. The stimulation from her tongue made my cock throb like crazy. It was hard for me to hold it any longer.

“I'm going to cum,” I told her.

Josephina stopped sucking my cock and pulled her head back.

“Cum on my face this time,” she ordered.

I aimed toward her face before I let go and shot several ropes of cum to coat the mature woman's face.

After I finished, I observed my handiwork. Josephina really looked the part of a washed-up, mature skank with my cum on her face. I did this. I turned an elegant woman in her 50s into this slutty looking cougar.

“Do you like what you see, Master?” Josephina asked me coquettishly.

I nodded. Just like how I felt proud when my cum drips from her backside, looking at her face coated with my cum gave me a sense of satisfaction and pride.

Josephina scooped some of the cum on her face with her fingers and then licked her fingers clean.

“You should try to taste your cum, Scott,” She suggested.

It was a sudden and weird suggestion coming from Josephina. It caught me off guard. Should I try to eat my own cum? I didn't think I should, but Josephina's suggestions so far have always been good for me. There must be a good reason why she suggested that.

I hesitantly scooped a little of my cum off her face with my fingers and licked it. The taste was salty and a little weird.

I glanced at Josephina to see her reaction. She smiled proudly, the smile she gave when I did a good job.

“So, why did you tell me to taste my own cum?” I asked her curiously.

“You wanted to be a good Master; I think you need to understand how your subs feel. Do unto others as you want others to do to you,” Josephina answered.

That sounded logical.

“So, Scott, with that principle in mind, I give you a choice: you can tell me to clean up, I will clean your cum on my face with my finger, and I will lick them clean, or you can tell me to let it stay on my face for a night. I am about to go out to meet some friends. If you choose the latter, I will meet my friend with your cum on my face. As a good Master, which one will you choose?”

Did she really let me choose the latter option? It would destroy her reputation if she went out with my cum on her face. Of course, no matter how hot it sounds, I didn’t want that. If I were in her position, I would rather lick clean my cum on her face.

I took another scoop of my cum on her face.

“Clean up your face,” I told her, then licked the cum on my finger clean.

Josephina let out a sigh, a relieved sigh if I might guess.

“I was ready to do the latter if you chose it; I would be pretty embarrassed, but I think it will be pretty hot. But I knew you would choose the first because you are a good guy, Scott.”

I took that as a compliment.

Continued in the next part >>

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