My Sister's X-Boyfriend , Greg, Part I

Greg fumbled through a drawer for a few seconds when he suddenly located a jar of Vaseline . He popped the top open and smeared a generous amount all over his fingers. With a loving gentle look on his face, he embraced me by wrapping both arms around my back as he drove his tongue deep into my mouth. I eagerly reciprocated by wrapping my arms around his darling freckled shoulder blades and swirled my tongue all around his. While we frenched, slowly, Greg moved his lubed-up fingers down to my crack. Knowing that he needed to lubricate me, I spread my legs slightly and loosened my ass lips.

At first, he softly smeared the jell all over my hole and rubbed his fingers in soft concentric circles around it to get me super hot & hungry for his cock. As we continued to french like crazy, I felt an intrusion into my opening by one of his fingers. I was so hot at that point, I thought I was going to black out in excitement. I drove my tongue deeper and deeper into his mouth gesturing to him that I loved what he was doing to me.

About half-a-minute had passed when I felt a second finger abruptly enter my hole. By now I was so hungry for his cock that I began to rock my ass back and forth as our mouths parted and I planted deep wet kisses all over his neck & lovable freckled shoulder blades. Once his two fingers twisted back and forth in my hole about twenty times, Greg pulled them out and kindly said, “ Scotty, I don’t want hurt you too bad the first time, so bend over the toilet seat and spread you legs as far as you can. Then grab on real hard to the seat cover”.

I did exactly as Greg recommended. He smeared a generous portion of the jell all over his cock, squatted slightly so he could come up from behind me and inserted his cockhead up to my opening. Greg then exclaimed, “ Now if it hurts, grip the toilet seat as hard as you can, Scotty.”

No sooner did Greg give me his recommendation when I felt his cockhead bluntly penetrate my opening. The pain was so sharp and incredible, I let out a horrific squeal in dismay. I felt like I was being busted wide open. Tears filled my eyes and my knees buckled. Quickly observing the torment I was enduring, Greg grabbed me so I wouldn’t fall to the bathroom floor. Immediately, he pulled his cock out of me and asked if I was all right. At that point I was gasping for air into my lungs as my body became paralyzed.

Greg hastily stood me up, turned me around and hugged me ever so dearly as tears streamed down my eyes and onto his chest. He knew my teenage body was utterly traumatized by the event. His cock was so big and thick, any would-be virgin would have experienced the same anguish.

Softly, Greg stroked his fingers through my hair with one hand until my body calmed and I could feel my muscles come back to life. Once I caught my breath and he was sure that I was OK, he asked if I wanted to stop. But, we both knew without saying a word to one another that we couldn’t turn back now.

I gently replied, “No Greg, I want to try it again-- just give me a minute and I will be OK”.

He gently placed his lips on mine and we frenched ever so lovingly. Even though I was still somewhat in pain, I wanted Greg’s dick in me so bad that I was absolutely committed no matter how much it hurt.

After a minute or so, we parted our lips. I bent over again, spread my legs and grabbed the toilet seat again. Greg stroked even more Vaseline onto his thick cock. He lowered his body like he did the first time and inserted his cockhead into my crack until it touched my opening. Slowly he penetrated me once more. While the pain was still incredible and my body jerked violently, I didn’t dare outwardly display the agony I was in. I knew it would just take time for my hole to embrace his big & thick piece of meat. And no sooner did I reach this conclusion when Greg exclaimed, “Now let’s just stay like this until you get use to me , Scotty.”

While the pain continued to persist, I kept my sanity by thinking how hot we must have looked with me bent over holding onto the toilet seat with his hot thick cock inside me. If ever there was a picture I wanted to send to my sister, it would have a photo of what we were now doing.

Greg placed his hands on my hips and slowly worked his rod up my hole. The pain was so blistering that I had to let out several squeals along the way. It was almost like trying to park an 18-Wheeler inside a one car garage. Greg keep encouraging me as his cock thrust deeper and deeper up my hole. Once he was about halfway, he exclaimed , “ Oh Scotty , I just love knowing that I am popping your cherry”.

Even though I was in a tremendous amount of pain, I managed to reply, “ Well I’, glad you’re popping my cherry too, Greg,” as I struggled desperately to catch my breath.

Within seconds, Greg was finally all the way in me. He exclaimed, “Scotty, I can’t believe we are fully connected to one another now.”

With total pain still venting in my voice, I replied, “Well I’m glad we are connected too, Greg. I’m so glad we are doing this together.”

He quickly exclaimed , “I’m glad we are too sweetheart--I love you so much--OK, let me hold my dick in you for a few minutes until your hole expands and gets use to me.”

As I remained bent over with Greg’s cock deep inside of me, he explained that it normally takes two or three times before fucking really feels good. He added though that gay sex was by far hotter and more rewarding than straight sex, and that I would never want to try straight sex after we fucked several more times in the coming days.

After a few minutes, he began to pump me slowly. While it really hurt, again I did not outwardly exhibit the pain I was in. Instead I told Greg to go faster because I wanted him to cum in me so we would be truly bond together once and for all. Greg of course honored my request and began to go faster and faster. Before I knew it, some of the pain was gone. And I even let out a few soft moans of pleasure to let Greg know how much I appreciated the hot ass fucking he was giving me. I couldn’t believe that his big thick cock was actually fully inside me and the joy I was truly giving him.

By now he was humping me faster and faster with each passing thrust. I could tell he was getting close for he exclaimed in a huff, “Almost there sweetheart, almost there”, as his cock slide in & out of my hole with sheer fortitude.

I exclaimed out loud, “Ohhhh Greg, cum, cum for me, cum in my ass like gay guys do.”

No sooner did I say those words when Greg’s erupted and exclaimed, “Oh Scotty, I cumming sweetheart, I’m cumming,” as he struggled to catch his breath while his warm seed rocketed into my body. I felt so bonded to Greg now knowing that I let him pop my cherry and cum inside me. It was like no other feeling in the world.

Once Greg fully expelled his seed, he left his cock in my hole and pulled me up. He wrapped his arms around my chest and turned us towards the mirror so that we could both admire ourselves fully adjoined to one another.

As he began to go soft, he kissed my neck from side to side as if to tell me that I now belonged to him, and only him.

When he finally pulled out, he turned me around until I faced him. He looked into my eyes as if to say that he wanted to marry me and inserted his tongue deep into my mouth. We frenched for almost two full minutes by the time our mouths finally parted.

We then looked down at his soft cock. Smeared in the Vaseline were small strands of blood. Greg exclaimed, “Look Scotty, I really did pop your cherry, sweetheart” as a deep & warm sense of pride crossed his face.

I just smiled and replied, “Well, Greg, I’m no longer a virgin and I sure am glad you were the one I lost my cherry to”.

Greg was so happy, he exclaimed, “Come on sweetheart, lets take a hot shower together and get all clean before we go to bed---I want to soap you all up.”

As I stepped into the shower with Greg right behind me, we both knew this was only the very beginning of our relationship and there would be many, many fine years we would share together yet to CUM.