Chapter 30

I got into the center of the bed on my hands and knees and opened my legs wide. He quickly got behind me and I handed him the bottle of lube.

“Squirt some of that on your finger and on my bottom.”

He followed my direction. His finger was coated with lube, and he squirted so much on my asshole I could feel the cool, crisp liquid run down into my vagina. “I think you got enough there,” I said teasingly.

“I ... I ... I’m just afraid of hurting you.”

“You won’t, I promise, you’re going to be great at this,” I said encouragingly. I could tell my earlier speech on safety had all but destroyed his confidence, and I needed to build him back up again. “Now very, very slowly, work the tip of your finger inside me.”

A little shiver coursed through my body when the tip of his finger entered me. I could also feel my pussy start to heat up and build a bit of moisture. “Now, just a little deeper.” Another inch of his finger slipped inside me, past my tight little ring, and I let out a little moan.

He froze up and stopped. “Are you okay?”

“I’m fine, baby, it feels great, just a little more.” He continued to make slow, steady progress, opening me until his finger was buried inside me. “Now, work it in and out.” He spent the next minute or so rotating his finger back and forth. My vagina was soaked and my secretions were running down the inside of my thighs. Taking me a bit by surprise, he pulled his finger out of my ass, ran a different finger through the little stream of liquid, and then sucked on both of his fingers. I looked back and gave him a little smile.

“I can’t help it, I love how you taste.”

“Monica’s going to love you ... you know that?” We shared a big smile. “Okay, let’s try two fingers in my ass now, use some more of the lube.”

He squirted another large dollop on two of his fingers and slowly began to work them in. “Yeah, just like that, nice and slow.” I could feel his fingers opening me up, getting me ready. My pussy felt like it was on fire, and I needed a little relief. “This is a bit of an advanced move, but use your other hand and rub my clit.” My earlier training had paid off; he instantly found my clit and used the tips of his fingers to gently manipulate it. “Yeah, just like that, it feels so good,” I moaned.

As he continued to work his fingers deeper inside my rectum, he simultaneously rubbed my clit and my body began to climb. “Just a little bit more,” I grunted. I felt his fingers bottom out in my asshole; he slowly worked them in and out a bit faster and my body convulsed as a powerful orgasm rocked my body. When he could tell I was there, he expertly withdrew his fingers from my clit, just like I’d taught him, but he kept both fingers buried inside my tight little hole.

“God, that was amazing,” I said, while still attempting to catch my breath. I loved the look on his face. I knew he felt so proud, so accomplished.

“I love doing this with you,” he said shyly.

“I love it too, are you ready for more?”

“I am.”

“Okay, let’s do this. Just remember, slowly.”

He got behind me, and I took a deep breath and tried to relax. He withdrew his fingers and I felt the tip of his cock push against my asshole. Then he eased forward and his large mushroom head popped inside me. “Yeah, just like, honey, it feels good.” Displaying a patience that was quite unexpected for someone so young, he gently eased forward at what felt like a millimeter at a time. Every few seconds, he asked me if I was okay, and I assured him I was. I could tell he was really afraid of hurting me, and my earlier lesson on safety must have really hit home. He was being careful and putting my need for comfort ahead of his need for pleasure. He was a remarkable young man, and he was going to make some lucky young woman very happy.

After a couple of minutes, he’d worked himself all the way inside me. He felt so good, and I felt so full. It was a delicious, naughty feeling, because it felt as if the head of his cock was deep in my stomach. “Now just hold still,” I whispered. “Let me get used to it.” This was always very important to me. I liked having just a bit of time to adjust and acclimate myself; it helped to let my body accommodate such a foreign invasion.

After about a minute, I was ready. “Okay, honey, now, nice and slow.” At a snail’s pace, he eased out of me and very gently worked his way back in. “Yeah, that’s perfect, it feels so good.” I was getting those familiar little tingles in my stomach and it felt as if my pussy was on fire.