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

After the wonderful nap Greg and I took together, I awoke to soft sweet gentle kisses being planted all over the back of my neck coming from his tender lips. His masculine body remained cuddled up tightly next mine as we laid there on our sides. When I squeezed his hand that was wrapped over me to let him know that I had stirred, he whispered in my ear, “Did you have a good nap sweetheart?

I softly replied as I opened my eyes. “ Oh Yea, how about you?”

Greg suddenly yawned and replied, “Me too, cause it was with you.”

I figured after our little nap, Greg had to be horny as hell by now. He hadn't cum in well over a day and a half and I felt at that moment he would love nothing more than to fuck me again which of course I wanted to do as well.

As we remained lying on our sides trying to wake up, I inserted my upper leg between his two masculine hairy ones and rubbed them with my lower calf. At the same time, I reached my arm behind my back and worked it halfway down until I felt his cock with my hand which was pressed up against the crack of my ass. When I gently stroked his penis a few times, it only took about 20 seconds before his flaccid piece of meat grew firm and razor hard. This was my way of telling Greg that I wanted him and that I wanted him badly.

As my hand slid back and forth across his shaft, he let out a soft moan and said, “Oh Scotty,that feels so good sweetheart,” as he planted several more kisses on my neck.

Out of curiosity, I asked what time we had to be at the party.

Greg explained the party started in about a half-hour, but we had plenty of time since all we had to do was shower, get dressed and take the elevator up to the penthouse. He added that dinner was normally served late, around 9 P.M., therefore we had plenty of time given it was only 6:30. He also added that normally he went a little late to this particularly party and said that once we walked in, I would understand why, as he kissed my neck.

Knowing that we were in no hurry, I slowly rolled Greg over on his back so I could rest my head on his shoulder. I wanted to rub my hand all over his chest & nipples while I admired his beautiful masculine naked body at the same time. No sooner had I stroked my hand across his chest about five times, when Greg rolled on top of me and drove his tongue deep into my mouth. Of course I immediately reciprocated my driving my tongue into his while I wrapped my arms around the back of his neck.

As we kissed on and on, I became bolder and more confident by now. I spread my legs and wrapped them around his ass while I rubbed his firm shoulders blades ever so passionately. If that wasn't enough to wake both of us up, I didn’t know what was.

I loved it when Greg laid on top of me. It made me feel so effeminate and him so masculine, especially when his soft chest hairs rubbed up against my smooth skin. I think that’s why we were so attracted to one another. I loved masculinity, maturity and dominance, whereas I could tell Greg loved smoothness, youthfulness and passiveness.

When our lips finally parted, I looked up into Greg’s eyes and softly asked, “Do you have some more Vaseline?”

A huge smile came over Greg’s face. He exclaimed with delight in his face, “Let me go get it sweetheart, it’s in the bathroom.”

Greg hopped out of the bed and sprinted into the bathroom while I remained flat on my back. He looked so cute going to and from the bed with his huge stiffy that waved back and forth.

Just as soon as he got back in bed with the jar, I rolled over on my stomach and spread my legs. Greg immediately popped open the cap and applied an ample portion to my glory-hole. Very gently he rubbed his fingers in soft circles around my opening and then penetrated it with two fingers. Instantly I moaned out and told Greg how good it felt.

After a minute or so, Greg exclaimed, “Scotty, why don’t you roll back over on your back sweetheart? I want us to look at one another while we are fucking.”

No sooner did I heed Greg’s advise and rolled over when he grabbed my legs and placed them over his broad shoulders. Instantly I fell in love with this position! It was like we were about to fuck just like man and wife.

Greg placed the jar in my hand, told me to take a healthy portion and smear it all over his dick. Just as I began to stroke the jell on his shaft, Greg grabbed my ankles and pushed them all the way back almost to the headboard. Knowing that I was still holding onto his cock, he told me to place it into my crack until I could feel it touch my opening.

Just like Greg requested, I guided his cockhead into my crack until I felt it nudge up against my glory-hole. Once I was sure his dick was in perfect position, I exclaimed as if to ask a question, “OK Greg, how’s that?”

Greg immediately replied back in a somewhat brisk tone, “OK Scotty, just help me guide it into you slowly.”

No sooner had those words come out of his mouth when I could feel the sharp pain of his cockhead penetrate me. Just as I let out a passionate squeal, Greg said, “OK sweetheart--let’s just hold it here for a minute until you get use to me--we’ll be fine--I promise.”

I looked into Greg’s eyes biting my lower lip in desperation. Greg could see the obvious pain on my face. When he asked if I was all right, I replied, “Don’t worry, I’ll be OK---it doesn’t hurt anywhere near as bad as the first time.”

He gave me one of his drop-dead smiles as he leaned over and kissed me.

While I was certainly in pain, I loved knowing that Greg and I were adjoined together in the most intimate way possible between two human beings who loved one another. In fact, I was so in love knowing that Greg’s cock was in me, that after a few minutes, I asked him to slide it all the way in. I wanted all of Greg cock in my body and I didn’t care how bad it hurt.

He took one look at me, smiled, and then cast his hips forward very slowly. Within seconds, I could feel his thick piece of meat work its way inside me inch by inch. As Greg slide his cock slowly up my hole, he leaned over and kissed me on my lips again. After a moment or two, he exclaimed, “There, I’m all the way in now sweetheart, how does it feel?”

Even though my face was in agony, I replied, “ I’m OK Greg--Let’s just wait a bit.”

Knowing that I was still in anguish, Greg tried to make me laugh and forget about the pain when he jokingly asked, “What do think would happen, Scotty, if your sister, Lori could see us now?”

Well, needless to say that comment was a good one and we both broke out laughing.

I replied back , “Oh, I would give anything to see the look on Lori’s face if she could see us now, Greg?”

“I would too,” replied Greg.

No sooner did we get a good laugh in when the pain had subsided. I was so excited I exclaimed , “ Greg, can you believe the pain is gone?”

Greg replied with a smile on his face, “See I told you sweetheart---it just takes a few times and then pretty soon you get use to it.”

I replied back, “Well I didn’t know fucking felt this good.”

Greg relied, “Heck yea, why do you think gay guys love it so much!”

Before I knew it, Greg was pumping me ever so slowly and boy did it feel good. He could easily tell by my facial expression that I was loving every second of it. Of course I could tell by Greg’s face he was loving it just as much as me. The feeling was so good by now that I softly moaned out , “ Oh Greg, I wish we could do this forever.”

Greg moaned back as his cock began to pump me faster and faster, “Oh God Scotty, I wished we could too, sweetheart--you feel so good--we fit one another just perfect don’t we?”

By now we were going crazy with bellows and moans that came streaming out of our mouths. At one point I moaned out , “Oh Greg, Cum in me---I want it really bad.”

Greg cried back , “Don’t worry, I’m almost there sweetheart--almost there,” as he grasp to catch his breath.

It wasn't but a few moments later when Greg let out his breath as his body shook violently. He uttered a raging moan and exclaimed, “Oh Scotty, I’m cumming--I’m cumming, darling--I love you so much.”

With that, his cockhead began feeding my teenage hole with his warm holy sacrament. As I laid there with Greg on top of me and felt his cum squirt inside my body, I reached my arms up and grabbed his firm shoulders as hard as I could. I knew Greg deeply appreciated this for he desperately needed a vise at that point. He was completely out of breath by now as sweat dripped off his chin and onto me.

While Greg laid on top of me struggling to regain his composure, I couldn't help but think our lovemaking session drew us closer together than ever. It was the first time we engaged in sexual intercourse where both of us truly cherished the ritual. As far as I was concerned, we were truly one and I would have gladly married Greg right then and there if I could have.

By now Greg's body was begging to calm as the final droplets of his cum exited his body and entered mine.

Once Greg went soft, he pulled his cock out of me, and exclaimed, “ Are you all right sweetheart---boy that was so good.”

I looked up into his eyes with a smile on my face and exclaimed, “I’m always all right when I’m with you, Greg.”

He looked deep into my eyes, paused for a minute and then gave me one of his famous deep wet kisses. Immediately I wrapped my legs once again around his ass, and arms around his shoulders, as we frenched ever so passionately. Our love for one another just kept on growing and growing.

Afterwards we took a long hot shower together. Greg couldn't keep his hands off me the whole time. But then again, I couldn't keep my hands off him either. When we finally got out, we both toweled each other off, brushed our teeth and shaved. Greg wanted to shave me since I only had a few facial hairs here and there mostly on my chin. While Greg touched me up with the blade, I asked what my sister and he had been talking about. Greg just looked at me with an impartial expression on his face and said, “Well Scott, I think she wants to get back together again--she wants to know when I am coming home to see my parents and she wants us to get together for dinner one night.

Hearing that, I asked, “So what did you tell her?”

Greg said that in a round-about- way he put her off because he told her he wasn’t sure when he would be coming home. Then he looked me in the eyes and said, “But don’t worry, when the time comes, I’ll just tell her that I’m gay and am not interested in women anymore--and that I’m very happy being with you, Scott.”

Just as he finished touching me up, I gave Greg a kiss and jokingly said ( even though I really meant it ), “Shoot, I'll just pick up the phone right now, Greg, and tell her not to bother you anymore because were both gay”.

Greg just laughed and said, “Well let’s not do that now Scotty---you don’t want to flip her out,” as he admired his fine barber work and the smoothness of my face”.

Then I exclaimed, “Hell I’ll call her--I’ll call her right now, Greg-- and just tell her.”

Greg chuckle again and replied, “I know you would, but let’s not---come on-- let’s get dressed and go to the party”.

When we removed our towels and walked into his bedroom to get dressed, Greg kind of shocked me. Rather than putting on a pair of slacks and a dress shirt which I thought we were going to wear to the party, Greg told me to just throw on some shorts and a pullover. At first I thought he was joking. But when he jumped in a pair of shorts and put on a Chicago White Sox's T-shirt, I could see that he was serious. I found it very odd that we were going to a party in such an elegant apartment building wearing shorts and T-shirts. But Greg told me to trust him.

Just as I bent over on his bed to put on my sneakers, Greg told me to leave them cause we were going barefoot Well needless to say, by now, I thought Greg had either lost his mind, or we were going to some kind party for hillbillies.

And to top it off, just before we walked out the door, Greg did the most bizarre thing. He pulled from his drawer two black tuxedo bow ties and put them in his pocket. By now, I didn’t know what the heck was going on. But I figured I would find out soon enough.

When we walked out of his apartment and into lobby, Greg hit the elevator button and gave me another one of his quick kisses on my lips. No sooner had the door opened when there were about eight guys from his apartment building who were also headed up to the party on the 37th floor. They were dressed almost like us--shorts and T-shirts mostly. So, I at least didn’t feel as awkward or worried about how we looked. On the way up, Greg kindly introduced me to everyone and even though they were all very nice, I could tell they were eyeing me over.