“Eighteen, Mistress Tabitha. No, ma’am. I haven’t tasted my cum.”
“You’ve never come in a pussy or ass, and then licked it out?”
Swat!
“Nineteen, Mistress Tabitha. No, ma’am.”
Swat!
“Twenty, Mistress Tabitha.”
Josh’s back was bright red, and he began to shift his weight from foot to foot. He rolled his shoulders and rounded his back some. He was approaching his limit, and I was sure Tabitha saw it. Stepping to the side, she paused for a moment and moved to where she could see his face and visually check on him. She reached between his body and the wall to take hold of his cock.
“Mmm. It appears that you’re enjoying your punishment and staying after class.”
“Yes, Mistress Tabitha.”
I had a good feeling that Josh was as hard as could be. I still hadn’t caught the sight of the front of Josh. When I found them, Josh was already naked and leaning against the chalkboard. The perv in me really wanted to see the front of him.
This type of play session sounded like it was right up his alley from what James alluded to. And, like a great Top, Tabitha was going to push him to his absolute limit.
As her questions and swats from the flogger continued, I thought about what she had asked earlier—if he had tasted his cum. I couldn’t be certain, but I was almost sure that after working with James for so long that he most likely would have tasted his own cum. I knew he denied having done it for the purposes of the play session. A common act I had seen many times was for a female Top to have their male bottom come in them, and then they were instructed to lick it out of them. Though he wouldn’t have had the experience to come in James and then lick it out, he most likely had, had that experience with another Top. No one fucked James. Ever.
Suddenly, I pictured Alison on all fours getting pumped full with Josh’s cum. I pictured her barking at him to lick it all out. I reached down and felt my erection over my pants.
“Thirty, Mistress Tabitha,” Josh grunted.
He took all thirty from her, and his back looked like it was on fire. Tabitha set the flogger down on the desk, then unzipped the side of her tight skirt.
“Wrap it up, and give me that long cock,” she instructed.
When Josh turned around and reached for a condom from the jar on the desk, my eyes quickly covered as much land as possible. Tabitha wasn’t fibbing or trying to stroke Josh’s ego. Josh had been blessed with an incredibly long cock, and he even had very grip-able pecs that were covered in the perfect amount of chest hair. I was surprised, though pleasantly surprised, to see two small silver hoops hanging from his nipples. Josh had washboard abs and a chiseled V that angled flawlessly. His pubes were nicely trimmed back, proof that Josh took very good care of his body, both physically and aesthetically.
With the skirt hiked up and gathered around her waist, Tabitha took hold of the desk. Josh walked to stand behind her as he rolled the condom down the length of his shaft. With his hand on the small of her back, he lined himself up and slowly pushed inside her.
“Mmm,” she moaned as he slowly pulled back and almost out of her. The look on Tabitha’s face showed that she was enjoying his girth and length. She looked like she was really trying hard to stay in the stern teacher role, but she was loving his cock too much to reprimand him.
As soon as Josh took hold of her hips, he closed his eyes and began thrusting into her fast and deep. Tabitha went wild, moaning each time he thrust himself forward. With a dick that long, I imagined he was banging against her ovaries with each pump of his hips. Occasionally, she would gasp in shock and surprise, so it was safe to assume he was bumping those ovaries.
“Fuck me with that long cock, Josh,” Tabitha pleaded.
I kept my eyes on Josh, though, because his facial expression indicated he wasn’t enjoying this nearly as much as Tabitha was. I thought it was a little odd, especially since he supposedly had a thing for these kind of play sessions. His forehead had lines of wrinkles, and his brows were furrowed. He kept his eyes closed the entire time he fucked her pussy while she cried out in pleasure. I considered there was a chance that he was in deep concentration, but this felt different to me.
Josh moaned and grunted faintly, but it almost sounded like he was in pain. Moments after his abs flexed, he lowered his head and turned to face the chalkboard as he came.
“Ohhh, Josh,” Tabitha breathlessly panted. “Mmm.”
Josh pulled out, took the condom off, tied it and tossed it in the trash while Tabitha stood and straightened her skirt. Josh put on his bright red jockstrap that Alison poked fun at him for having. Keeping his eyes downward and looking a little lost, Josh waited by the desk while Tabitha zipped her skirt. She patted his chest and said that she had fun, and that he was always wonderful to have a session with.
Tabitha’s fingers curled around Josh’s waistband as she wrapped her arm around him. When I saw they were headed toward the doorway, I quickly moved away from the wall and headed toward the main room. I had a feeling they were headed that way for their aftercare, and I wanted to watch that as well. I had no shame or guilt in watching them, but I left the hallway quickly because I didn’t want Josh to feel like he needed to acknowledge me if he saw me.
Once in the main room, I immediately went to the bar area and grabbed a bottle of water. By the time I sat down at a high top table, Tabitha and Josh were seated together on a loveseat. She had collected two bottles of water that they were each sipping on.
I couldn’t hear a word they were saying, but I liked the fact that Tabitha had turned her body to face him as she spoke. Tabitha sat close to him and had her arm on the back cushion of the loveseat so that her hand could gently rub the back of his neck, head, or shoulder. With each passing minute, Josh seemed to come around more and more. The two of them sat together talking for about twenty-five minutes before they stood and hugged one another. Tabitha headed toward the entrance while Josh headed to the men’s locker room.
I took a deep breath and thought about their session. He obviously wanted that type of session, but to me it felt as though there was something deeper happening for him emotionally. I was going to try to figure it out myself, and if I couldn’t, I’d go to James. I had no doubt that James knew what Josh’s deal was. Josh was clearly capable of negotiating safe play sessions. But after seeing his session tonight, I felt like he still needed a mentor, and I was the perfect man for that task.
6
