*Second update today*
After a few minutes of kissing and about six “I'm sure,” I was laying on Jack's bed with my legs firmly wrapped around his hips. A few weeks ago, I was really unsure, but now that I know how much he really does care about me, I really think I'm ready for this.
I love you.
My hands were around the back of his neck, Jack’s arms on either side of me, holding himself up so he didn't fall. He kissed me deeply, taking things slower with me than last time. He was probably still hesitant about this since the last time I freaked out and didn't talk to him for almost a month. I slid my hand down his chest, feeling his soft skin get hotter and hotter the longer that we were kissing. I could feel his ragged breathing on my neck as he started to kiss all over my jaw. He pushed his bottom half into mine, slowly grinding down on me. Unlike the last time, this really, really felt good. I was still nervous, but I didn't want to stop at all.
My breathing was hot and heavy, just like his. My hands roamed all over his chest in back as he sucked on my collarbone. I let out a small moan, never actually know how good all of this felt. I brought my hands up to Jack’s shoulders and pulled off his shirt, leaving him naked from the waist up. His own hands went up my shirt, feeling my chest. He pulled my shirt up farther, making me sit up and take it the rest of the way off for him. I fell back to the bed, bringing him with me, finally allowing for that skin to skin contact I’ve been wanting from him for so long.
Jack played with my zipped, slowly pulling it down. He pulled up from the kiss and looked at my eyes. I just nodded before he pushed his hand past the fabric, taking hold of my growing erection from the outside of my boxers. He sensually ran his hand along my length, making me moan against his lips. I stopped kissing him, swinging my head back, letting him touch me however he wants. I bucked my hips into his touch, enjoying every motion. No one has ever touched me like this, and its feels freaking amazing.
He pulled his hands out of my pants, making me look at what he was doing. He was unzipping his pants and pulling them off. Jack threw his clothes on the floor with our shirts, then started to pull my jeans off. I lifter my lower half, making it easier for him. I could see how turned on Jack was through his boxers and it made me feel pretty special that I did that too him. He hovered back over me, kissing me again. His warm body was rubbing against mine, making every part of me go hot. The only things keeping us from full skin to skin contact, where the thin layers of our boxers.
Jack started to kiss his way down my body, making me shudder against him and the bed. he ran his slender fingers around my nipples and down to my waist. So he was face to face with my almost completely hard dick. He kissed it from the outside of my boxers, knowingly torturing me. He hooked his fingers under my boxers, pulling them off my legs and onto the floor. I felt a little self-conscious laying there naked in front of him. No one has ever seen me naked, besides my parents when I was a baby. Oh, if only they could see my now. The son of two very strict Christians, laying in bed, naked, with another man.
I propped myself up on my elbow looking at his movements. He rubbed his hands up and down my thighs, giving me a hungry look. “Have you ever had a blowjob before?” he asked me, being very blunt, but almost slutty at the same time. I loved it. I shook my head now and held my breath. Jack smirked before taking my cock in his soft hands. He kept looking at me and stuck his tongue out placing it on the shaft. I stared at him waist for him to move. He slowly licked up my length and swirled his tongue around the tip. I moaned a little biting my lip. He did it a few more times before taking me into his warm and wet mouth. My eyes rolled back, and so didn't my head. I laid back against the mattress, letting myself get completely engulf in the most wonderful thing I think I have ever felt in my life.
He sucked me up and down, stroking half of my with his hand. Yeah, this was way better than my own hand. I breathing heavily and moaning loading. One of my hands laced its fingers in his black hair, keeping his mouth on me. He went down farther and farther, taking more of me into his mouth. I felt him swallow hard around me, but never once gagging. My teeth pierced my bottom lip so tightly, I was surprised that it wasn't bleeding by now. Jack brought his head back up slowly, tracing his tongue around every part of me. He was fucking skilled at this. He kissed his way back up my and finally back to my lips. I didn't care what was just in his mouth, I didn't hesitate kissing him back.
I was so painfully hard now, I just wanted to move on. I was a little worried about him wanting a blowjob as well, but luckily he didn't say anything. There is no way that I could be as good as him, I had no clue even how to give blowjob.
He stood up walking over to the nightstand next to the bed.I saw him pull out a condom and a bottle of lube. He laid back on the bed, setting the items to the side of us. He pulled off his boxers, so that he was naked too. He was a lot bigger than I thought he was and It made me a little worried. How the hell this was going to work. He kissed me and stroked me a little more, making me forget about my worry. I scooted up so my back was against the pillows a little better. Jack got between my legs, positing them the right way.
“Are you sure about this still?” He asked me. I looked at him and nodded.
“Yeah,” I breathed out.
“Are you sure?” he asked me again.
“Jack, yes. Just start.” I said for him to continue. He nodded a last time and picked up the bottle of lube. I was watching every move, but I wasn't sure why. He spilled a small amount of the liquid on to his fingers and started to rub around my entrance. It was cool, but actually felt good to be touched like that. He poured some more on his fingers, making them very slick with the lubricant. “This is probably going to hurt, okay?” he told and and I nodded understanding.
I few seconds later, I felt one of his fingers start to push its way inside of me. I squinted my eyes, not in pain, but a little bit of discomfort. “Are you okay?” he asked me. I nodded and felt him push and pull his finger out of me very slowly. Soon, the little bit of discomfort went away and it just felt a little weird having something inside me like that. He pulled out a little, but still inside me. I felt him add another finger, and this time I felt a little bit of pain. I hissed and twisted my lower half.
“Shit, are you okay?” Jack asked, a little voice of panic coming from him.
“Yeah, just hurt a little. I'm fine. Just… Go slow.” he slowly pushed the two fingers inside me, stretching the surrounding muscle. He scissored them lightly and turned them in different direction inside me. The pain was leaving again, making me feel only the discomfort. he wiggled his fingers around more until he hit a certain spot that made me cry out in pleasure. My hands gripped the sheets as he continued to press into that spot. I was moaning loudly and practically screaming as he circled his fingers into the bundle of nerves. I changed my mind about the blowjob being the best feeling ever, it was actually this feeling right now. I started to grind my hips down on his hand a little, wanting more and more of the feeling, I was getting really close.
To my displeasure, Jack pulled his fingers out again and wiped them on his sheets. I guess that’s why he didn't have actual blankets on the bed right now. The pleasurable feeling was going away again, back to normal. He kissed me again, before sitting on his knees between my legs still. He picked up the condom, tearing open the foil packet with him teeth. I watched him and he slid the rubber over his entire length. Jack poured even more lube in his hand and ran it over himself. He closed his eyes, probably enjoying the feeling after not being touched for a while. He opened them back up, looking at me. His eyes clouded with lust and desire.
He kissed me quickly again and sat back up. he pulled my legs so that they would rest on his thighs, bringing my hips up, so he had better access. He held his tip at my entrance and looked up at me. “Are you sure you’re ready?” I swallowed and nodded. I took a deep breath and felt him ever so slowly push his tip into me. I hissed at the pain that shot through my lower half. It's hurt way more than his fingers. He stopped, rubbing my hips, waist and thigh. I nodded again, letting him continue. He started to push in again more. “It's okay,” he said going farther in me. “I need you to relax okay? It can hurt even worse if you don't stay relaxed.” He told me sweetly. I relaxed my muscles as he went farther in again.
His hips finally met mine, and I sighed, happy that he was finally completely in me. A thought came to me, that was it, I wasn't a virgin any more. He came down to me, not moving and kissing me as much as he would. “Move,” I whispered to him.
“Are you sure?” I chuckled a little.
“I'm not glass, Jack. I will be fine. Just move, okay?” He nodded and pulled only a little of the way out, then pushed back in. My face scrunched at the feeling. It wasn't really the best, but I could feel myself slowly get more and more used to him. My hands went to the back of his neck again, kissing him as a distraction from the pain. He slowly pulled out a little more each time and coming back in. I could feel his lips tremble against mine. I could tell that he just wanted to move faster. It was probably overwhelming for him to not have sex for months and me being so tight. But he stayed slow, for my sake.
His hips started to pick up a little pace, rolling against mine. I still wasn't in heaven, but te was feeling better each time. “You can move faster.” I told him. Before he could ask me if I'm sure again, I nodded. He looked down between us and pulled almost all the way out, he came back in faster than usual. I hissed and moaned at the feeling. Jack tucked his head in the crook of my neck, kissing and sucking on all my sweet spots. I could feel his hot breath, panting on my shoulder. he hands ran down his back, feeling the small beads of sweat that littered his back. His hips, snapped harder against mine, making me hiss again, but this time actually feeling really good too.
“Sorry,” he mumbled and went slower. Jack took a hold of my dick again, sensually stroking it. I swung my head back, enjoying the good feeling that was slowly starting. I had softened a little at the beginning. I guess I didn't do well with pain. The pleasure was building back up. Jack kissed and sucked and his hand tightened around my cock, squeezing me and running his thumb over the tip. My body was hot, my breathing heavy and rugged. I moaned letting Jack know I was about to come.
My body shuddered against his as I finally came, spilling onto my lower abdomen and on my chest. My short nails dug into his back, my heels digging into his thighs. My toes curled at how amazing my orgasm was. My first orgasm from another person. Jack moaned at the tightening of my walls, he thrusted a little faster and continued to stroke me through my high.
“Come, Jack.” I said in his ear. “Come on, please, for me.” I said again. He looked at me and moaned. He froze, dropping his head into my neck and moaning quietly.
Jack stayed on top of me. Slowly kissing my neck. He finally go to my lips, kissing them lightly. He pulled up, looking at my eyes. His face was red and covered in sweat, hair sticking to his forehead, but hot all the same. His eyes held so much admiration, making me not regret a single thing that just happened. He kissed me softly again, before rolling off of me and carefully pulling out of me. I felt so empty again without him there.
Jack and I laid on our backs, basking in the hot air of the room. He looked at each other and smiled. I watched him pull off the condom and tie the end, before throwing it in the trash bin on his side of the bed. he gave me a box of tissues to clean myself off with. took them from me and threw them in the trash too. He rolled closer to me, making me rolling into his chest. He pulled a thin sheet over us. We just laid there together, feeling tired and out of it. My whole body felt sore, but amazing at the same time.
I looked at Jack, he looked like he was sleeping already. My heart swelled so much for him right now, I could only think of one thing.