Jack Ch. 02


“Lie back, I want to be inside you.”

Derek looked at my apprehensively and I quickly tried to ease his fears.

“It’s okay. I will use my fingers to show you. I won’t go any farther unless you ask me to.” I sighed when he visibly relaxed.

“Okay,” he said. “I trust you, Jack.” I smiled, knowing he was lying, admiring his courage in spite of his fear.

“I will be right back,” I said as I left to the bathroom. I didn’t bother with the light, a benefit of being a bachelor, I knew where everything was. In the cabinet sat a tiny bottle of baby oil. I took it down and selected a few condoms. When I entered the bedroom, Derek was n his side, facing me, his head propped on his hand.

He looked wonderful to me. Quite some time later I began thinking of him as the Imperfect Adonis—which actually made him perfect.

He sat up as I approached, crossing his legs under him. I had to grin at his innocence. He blushed self consciously as I set my things on the nightstand.

“What?” He fiddled with his fingernails.


“You were grinning about something.”

“Yes, you.”


“Yes.” I knelt in front of him and held his cheek as I kissed him. He nervously flicked his tongue over my bottom lip as I pulled away, his blush more pronounced than before.

“No need to blush, sweetie. That was a very tender thing to do.” He focused on his hands again and I sighed. “Derek, I would like you to lie on your stomach. I won’t do anything without your approval. You can trust me.”

“I do. I am just scared.”

“Let me be scared for you, honey.” He nodded and laid on his belly, his legs encasing me between them. I loved the look of his lightly furred ass as lay before me. Open, willing, adorably nervous. I didn’t tell him I was more frightened than he.

Leaning forward I massaged his shoulders, wanting to ease his tension. Working slowly and steadily, I moved down his back, to his waist, to his plump ass. He moaned as I moved my hands over his fleshy globes.

I worked my fingers over him, relishing the feel of him. He began pushing back on my hand as I ran it over his crack. I stiffened immediately and I tried to keep myself in check. It had been so long and he was so sweet….I groaned with my own frustration and he glanced back at me.

I covered with a smile Gaziantep Escort İlanları to his questioning brow and continued to open him up.

“Derek, I am going to take some oil and put it on your crack. After that, I am going to massage your hole but I won’t enter, okay?”

“Yes. Okay.” My cock brushed against his thigh as I reached over him to the stand. I opened the cap and held his ass slightly apart to catch the liquid. He shivered at the chill, but relaxed quickly as I rubbed it in.

“You never get used to the chill,” I told him. He chuckled a bit and laid his head on his forearms. With practiced hands I moved over him, his bud enticing me as my finger lingered with each pass. Derek stiffened and moaned, my cue that he was finally enjoying this part of it. I kept moving, but spoke quietly to him.

“Derek, I would like to use one finger and put it inside you. Only one and very slowly. Let me know when you are ready.”

He sighed and looked over his shoulder.

“Okay. Show me.” He watched me curiously out the corner of his eye as I took another dab of oil and put it directly on his hole. It recoiled from the coolness and I rubbed over it lightly to warm it. Tentatively, I pushed against him, letting him open around my finger naturally.

He was so tight, never having been opened by another man before. The sensation was amazing. I had never been with a virgin before and I wanted to take my time. For his sake and mine. No one really understood that this young man was very dear to me and I wasn’t going to be a regret in his life.

I entered him fully, my thick finger easing up to my first knuckle. His moan of pleasure was incredibly and I was shocked by it. He pushed back to me lifting his ass the tiniest bit.

“More, Jack. I am ready.”

“No, honey. Take it easy. Let me give you another finger. Be patient.” He frowned in frustration, but I wouldn’t be budged. He knew I was serious.

My forefinger withdrew and I put my middle finger next to it. With another touch of oil I gently eased into him. He tensed up and I tried to offer him advice. “Push from the inside just a bit, that will help the tension.”

He tried and I slid in slowly. I took extra care as I moved farther in. He sighed as I inched in and out, letting him take as much as he could.

“God, Jack…aaahhhhh, that feels so good.”

“This is only the beginning, honey. There is so much more to know.”

He purred as I pushed farther into him, letting him close on me, then easing again. Gauging how he was doing, I let my fingers enter him fully, adjusting to the intrusion, then relaxing as he accepted me.

He moved as I moved, fingering him with gentleness until he thought he was ready to move on.

“Derek, do you feel you are ready?”

“Yes. You feel so good to me, I want to know everything.”

“Come here. Lie on your back. This should be the easiest for you to begin with. This way you can also tell me how much or how little you are comfortable with, since you should be able to see me.”

He turned over quietly his nervousness screaming out to me. I felt for him deep in my heart. He was putting on a good act for my sake and his own.

“I am ready, Jack.”

I let his legs rest on the bed as I rubbed oil on my cock. I was concerned about this part of it. I get considerably wider after my head and I didn’t want to risk hurting him. Taking it slowly may not work for him.

He indicated he was ready by pulling his legs to his chest. I stroked his cheek as I pressed my head to him. Though he was prepped, he was still so tight as I took my time entering him.

He winced a few times as I applied more pressure to make the final move.

“Push from the inside, baby,” I whispered to him. When he pushed, I leaned against him, my head popping through his tender ring. He gasped, but I stopped, letting him adjust to me.

“Jack…..fuck!” I held his hand as I eased just a bit farther in. This would be the hardest part. There was almost an audible pop as I finally made it through his tiny ring. He gasped and sighed, releasing my hand.

“Damn, Jack…..are you trying to kill me?”

“Shush, you are fine. Let yourself get adjusted to me and I will move again.” He nodded waiting, flexing his ass around me, having no clue that it was making me crazy! I wanted to plunge into him but I held fast, there was no way he could handle that.

“Okay, I am going to move. Slow and easy. While I do this, you can stroke, or I can do it for you. That helps with any pain sometimes and we also may be able to come together like that.”

“We could come at the same time?”

“Yes, it does happen.”

“Wow….” He smiled at me and took his cock in his hand. His fear kept him a bit soft but it sprang to life when he touched himself. I kept upright with a tilt to my hips to keep the pressure off him until he was used to sex. As I crept farther into him his eyes clenched and he moaned loudly.


“God, this feels so good…..I never knew…” Steadily I moved faster, my balls slapping at his ass as I buried myself to the hilt inside him. I watched him closely, his deep brown eyes so emotional, so innocent. His young man’s mouth agape with pleasure as he opened himself up to me.

I leaned into him and he wrapped his legs around my waist. I stretched a bit and kissed the tiny scar on his chin. So perfect in his imperfection, so handsome. His belly quivered as I thrusted harder. Just seeing that almost made me climax. I loved his belly, that baby fat that will never go away with the beer he indulges in. I loved that about him.

He was groaning, clawing at my shoulder as he jerked himself. I couldn’t last…he was too good. I felt so much for him and he trusted me. I looked at how I was connected to him. Seeing my body in his was amazing, sensual, so hot.

He looked into my eyes and I cannot describe what I saw there. His whole being was open for me to see and it touched me.

Derek writhed beneath me, catching my cock just right and I only had a couple thrusts left before I spilled my seed into his virgin ass. His fist flew over his throbbing shaft and he looked in my eyes again.

“I am coming for you, Jack!” His body tensed, clenching hard on me, my own orgasm spewing forth into him. “Ahhhh, God, Jack, yes! Oh fuck yeah!” I was silent as I watched his first orgasm with me. My own meant nothing, but this wasn’t for me. This sweet young man was getting what he really wanted. I was go glad to be the one he went to.

As his shudders subsided, I pulled from him. I went to the bathroom and dampened a washcloth, cleaning myself quickly, then bringing one out for him. He didn’t move when I held my hand out to stop him. I wanted to clean him myself.

He watched me as I wiped off his stomach and dropped the cloth into the hamper.

“Jack…..is there more to it?”

I couldn’t help but laugh. He smiled and waited for me to answer.

“There is so much more. I will show you.” He sat up and snuggled into me.

“Then show me, baby.”

To be continued in part 3

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