Continuing My Education Ch. 01

"No need to force yourself. It's your first time, I gather," purred Cass. I made some kind of grunt, but I continue to bob slowly up and down, each time letting the head hit the roof of my mouth. My finger dove down between Cass' soft cheek and found her hole. A subtle shift of Cass' weight and move of her legs told me she approved. I just let my fingertip caress and push a little at the entrance, rather than push inside. I knew it would be rough without any kind of lubricant, and my mouth was far too happy to take a break.

As the moments passed, I was aware that Cass' breathing was faster, her body moved more, and her cock seemed to grow slightly in my grip, so I knew her orgasm was close. I felt a little disappointment in the back of my mind, thinking that it would be over, then I reminded myself that Cass and I were just starting as lovers, and I would be getting a second chance. I quickened my pace, and after several more moments, Cass grunted," If you don't want to taste yet, I..."

I silenced her with a look and though I pulled my lips back around the head, I pressed them sealing, telling her I was ready. Her hand on the top of my head, she screamed and I got my first taste of cum. I was swallowing before the first jet hit my tongue, so at first, I didn't get a proper taste until she released more. I expected a stronger, more unpleasant liquid, but her cum was slightly salty and musky, but otherwise nondescript. As I swallowed I must have looked lost in thought, because Cass was suddenly stroking my cheek and asking me if I was okay. A few more licks of her head and I pull back, licking my lips.

"No, I'm fine. In fact, I'm great. That was wonderful and intense and erotic, and I was happy to do that for you," She pulled me up hard and kissed me passionately, then broke off.

"Oh my, you really did enjoy it, didn't you." I was confused at first to what she meant, but when she looked down my body, I understood. My own cock was achingly erect, and had been the entire time, thought I hadn't paid attention to it. I smiled rather sheepishly. "No, don't be embarrassed, honey. Be happy and proud."

She quickly flipped me over and then considered me for a moment. She retrieved a bottle of lube from beside the bed and poured some on her hands.

"Just relax. Completely relax." She kissed the very tip of my cock, then then started stroking with both her lubed hands. The feeling was exquisite, almost as good as sex, and I really did relax and enjoy it. I didn't think I would be able to last, as aroused as I was, but Cass had an instinct on when to slow down and ease me back. I had closed my eye when her fingers began to squeeze and massage my balls, but I opened them again when her wet finger probe further down, against my anus. She just massaged there and push slightly until I really relaxed, and then she slid her finger into me, without hesitating. I could feel the digit moving, twisting, until there was a sudden intense sensation inside and I felt like I was going to erupt that instant. I didn't, but I stared at Cass, who was beaming.

"You can just let go, now." The way she spoke, with experience, and with a gentle tone, helped me trust her completely. Cass started moving her finger again, but not in a thrusting motion. Her finger flicked back and forth over my prostate and I could barely stay in place. I was surprised when my penis started to soften for a moment, enough that I panicked a little bit. Cass smiled reassuringly, but didn't start stroking my shaft again.

"Don't worry about that. You are just reacting to having my finger inside, and the intensity of the experience. Sometimes when I'm over aroused, I soften, just because my body doesn't want to release yet. Trust me, honey, don't worry." I tried to relax as much as I could, but I really did feel like I was going to explode if I didn't orgasm. I saw clear fluid starting to leak out of my slit. Instead of stroking, Cass squeezed, as though trying to milk me. More of the fluid streamed out as her finger again moved inside me. My hands reach out and gripped the bed, and I felt like I couldn't stand much more of this, even though Cass had only begun.

She placed soft kisses on the head of my cock and on my belly as she massaged my prostate, before eventually taking me back into her mouth. It seemed like an eternity, but I grew erect again, and before long I was aching to erupt. I couldn't control my muscles any more and I thought that I was going to tear Cass' finger off. She knew exactly what she was doing, and gave me a simple look letting me know it was okay to orgasm. I felt afraid to really let go, but my body took over, and I tensed, with such a powerful orgasm that I thought I might pass out. My eyes closed and my back arched, making it difficult to keep my hips in place. I did so, just barely, for Cass' benefit. I figured that I had released a fountain.

When I finally looked down and saw Cass licking her lips, not a dribble of cum spilled, I took a deep breath. Her finger was still inside me, but I could tell that it was slowly being drawn out.

"Stay here, don't move, and breath deeply." She went quickly to the bathroom, and I heard the water running for quite sometime. I did focus on breathing, processing what had just occurred. I felt empty, and slightly uncomfortable, but I didn't really mind it. I guessed that everyone who had been taken in the ass felt similar afterwards. And this was only Cass' finger. I began to wonder what it would be like to take her cock, when Cass came back out with a towel and a wet washcloth.

"It takes a long time for the hot water to get going, so I apologize. You haven't felt any... urge to go?" she asked softly as she knelt before me.

"Um... no, not really. Just empty, and a little soreness," I responded getting up on my elbows. Cass slowly cleaned my cock, thighs, balls and ass. She also seemed to be checking for any bleeding.

"That's very good. I was being as careful as I could, but anal play can be a little risky. I've done it with gloves before, but with you, I didn't want that barrier," She smiled up at me, took the washcloth back to the bathroom, then came back to kiss me.

"And how do you feel emotionally?" Her eyes locked onto mine, and I felt a little tension in the moment. Her fingers stoked my face, and I realized that I would have to pick my words carefully again.

"I feel very close to you, and not just physically. I know it takes a lot of trust to let someone do what you just did. I do trust you," She nodded, but keep that steely lock on my eyes, wanting more. So I continued, telling her exactly what I had been thinking. "Just before you came back out with the washcloth, I start to imagine you fucking me there, and not just with your fingers."

Her eyebrows raised, and I saw her lips twitch a little.

"With your cock," I added, with conviction, trying to emphasize it for her. She broke into a grin.

"I'm really glad, Jason. It's not a requirement, despite what the smile on my face might say, but I've enjoyed fucking boys in the past, and it something I would want to do with a partner I really loved," She put her head down on my chest and snuggled me. "To be honest, I prefer to take rather than give most of the time. But I want... no I need variety."

She sat up suddenly and stared at me with a slight frown. "Not that I mean other lovers, or anything. I'm not like that. I just like sex, different kinds of sex and..." I stopped her with a kiss, and held her tightly.

"I get it Cass, and I want the same thing. You'll probably have to teach me a lot, but I'll be a willing student, to be sure," I whispered and kissed her forehead.

"Turnabout is fair play, as they say?" she asked demurely and nipped at my chest.

"Um... yeah,"

We rested in silence, as the afternoon faded and soon it was dusk, and I could tell from various rumbling sounds that we were both hungry.

"Chinese?" We both said at the same time, and then laughed... together... it was wonderful.