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

As the engines slowed, the plane turned its nose downward and plunged through the clouds on final approach. I leaned over, handed my empty soft drink cup to the fight attendant and stared out the window. I wondered if Greg was still the same great and good-looking guy I remembered from days gone by. I hadn’t seen him in over five years after he and my sister ended their casual six year relationship.

I was now in my final year of high school. Greg was now a well established corporate attorney working for a major corporation who was zooming his way up the ladder and had recently been promoted to his company’s Chicago office according to my parents.

Given I had just turned 18 and my sister was 28, I figured Greg was now about 32.

Both my parents and Greg’s arranged for me to stay with him for a week during Easter break so I could check-out De Paul, Northwestern and the University of Chicago. I was considering them among others to attend after graduation.

I always liked Greg far more than any boyfriend my sister dated. He was so very regal--so much above pure pettiness, and always greatly caring about other people’s feelings from what I remembered.

Whether it was baseball, the beach, river-rafting or even fireworks on the Fourth, Greg always made sure I was welcome if I wanted to go even despite my sister’s objections at times.

Aside from Greg’s wonderful personality, he was so All-American looking from what I remembered which I guess is the reason why he exhibited such self-confidence and charm. I recalled him being slightly taller than my dad (about 5’10 or so) with light brown hair, green eyes and a boyish face carved from the heavens. I kind of wondered why Greg hadn't married yet given everything he had going for him. But I was soon to find out why and how it would turn into be the greatest night of my life.

When the plane finally pulled up to the gate, my heart started pounding. While I was really excited about seeing him again, I felt a bit nervous & apprehensive. I figured it would take us at least a couple of days to warm back up to each other, especially since we hadn’t seen one another for so long, and given I was no longer the boy he remembered.

But no sooner had the plane’s door opened and I emerged from the jet-way, Greg was standing right there to greet me with a huge smile on his face. Any concerns about being nervous & apprehensive, vanished right away. He quickly put his arms around me and gave me a giant hug. He exclaimed with sure & sincere vigor in his voice, “ God Scotty, it’s great to see you again--you don’t know how excited I have been about you coming up here to stay with me . I can’t believe you are finally here and I am actually looking at you. We are going to have a great time together while you are here.”

I smiled right back and eagerly replied, “Geee Greg, you don’t know how good it is to see you too. I’m so happy to be here.”

Greg quickly pushed me back at arms length as he clutched both my shoulders so he could look me over from head to toe. He exclaimed with a giant smile still on his face , “ Wow you’re so big now--all grown up aren’t you ---you look great!"

I was now 5’7, 130 lbs, dark brownish hair hanging down over my forehead and hazel eyes).”

I smiled, shrugged my shoulders and modestly replied, “ Well , thanks Greg, you look really great too--exactly like I remember you.”

On the drive back to Greg’s complex, he informed me that he lived in a one bedroom apartment on the 20th floor, but was on a waiting list to get a larger two bedroom/two bath. He added that he would open the sofa-sleeper in the den and I could sleep there.

When we walked in the door, Greg gave me a quick tour of his apartment so I knew were everything was. He then helped me unpack and put my suit case away. Once I put my toiletries in his bathroom, we stripped down to our boxers and t-shirts given I had taken a late evening flight and it was now after midnight.

He fixed us both a glass of warm milk and we laid across his bed on top of his duck-down white comforter facing one another. The comforter was so very soft and cushy-- absolutely superb! My young smooth body sank right in and did it ever feel so good.

As we talked about the various colleges I wanted to visit, suddenly Greg pulled his t-shirt off. He looked just as I remembered him at the beach in trunks only his body appeared more mature now--especially given a sexy little paunch and miniature love handles that had matured on his stomach & waist. Brilliant modest soft light hairs still captivated his masculine chest as well as dark sexy freckles that showered all over his shoulder blades. Now that I was older, I thought Greg bestowed the most charming pink nipples in the world especially given the tiny soft light hairs that circled each one of them.

I couldn’t help but occasionally glance him over from head to toe. He looked so very sensual lying there on his side facing me with the palm of his hand holding up his head just like I was doing.

Just as we began discussing the last college I wanted to visit, I thought I felt his toes softly nudge up against my bare foot as if neither of us were supposed to notice. When I didn’t flinch or back my foot away, sure enough he gently pushed his toes further into my foot with each passing minute.

My heat starting pounding! I did everything I could to prevent my boxers from springing a huge tent.

Just about the time we finished our conversation, I felt his toes softly begin to stroke mine. I eagerly wanted to reciprocate. The next thing I knew, I began to rub my toes back and forth across his. We were now playing footsie and did I ever find it arousing.

Without warning, Greg suddenly placed the backside of his free hand across my chest. The feeling of his hand rubbing me through my t-shirt combined with his foot stroking mine excited me beyond anything I ever experienced. Greg could easily sense I very much liked what he was doing to me. As he continued to rub my chest and played footsie with me, he looked into my eyes with his soft gentle green ones and whispered, “Do you like this, Scotty?

I softly replied with a wide smile on my face, “Oh yea, I like it a lot, Greg.”

He looked into my eyes again and softly asked, “Scotty, do you think you might like guys better than girls”.

This time I looked deep into Greg’s eyes and replied, “ Well, I have never had sex with a guy before, but I sure do like what we are doing, Greg. It feels so good being with you like this”.

With that courageous statement now out in the air, Greg slowly moved his lips closer to mine. Tenderly he kissed my lips until I opened my mouth and gladly allowed his warm wet tongue to slowly guide its way in. My cock skyrocketed and I knew without looking, Greg’s dick was super stiff too.

Seconds later, I gladly reciprocated by inserting my tongue into his. Greg’s mouth tasted delicious as I swirled my tongue all over his! I wasn’t scared or nervous even though it was my first sexual encounter with another male.

As we frenched ever so passionately, Greg worked his hand down to the elastic waistband inside my boxers. He rubbed his fingers back & forth inside them and very slowly tugged them down below my knee caps. By this time, I was so stimulated and aroused, I forced my tongue deeper into his to let him know just how accepting of what he had just done.

Gently, he placed his hand on my stiff rod & balls and rubbed me ever so tenderly while he worked his tongueeeper and more vigorously into my mouth. I could have done this forever! We were so much in heated passion now as we relished in both the taste & touch of each other’s bodies.

When our lips finally parted, Greg, softly said, “ Scotty if it is OK, I want to see all of your beautiful body.”

Before I could respond, he rolled me over on my back, helped me tug my t-shirt off and casually pull my boxers off until they dropped on the floor. Now, my naked body laid right before his very eyes as he sat up on his knees and looked me over from head to toe with a huge smile on his face. Within seconds, I felt a sense of submissive eroticism unlike anything had I ever fathomed knowing that Greg was so turned on looking at me in the buff. Here he could have had probably any babe in Chicago with his good looks and charm, but I was the one that floated his boat.

Greg exclaimed with glee, “God Scotty, you are so beautiful-so absolutely beautiful--and I can’t believe how big your cock is too--it’s gorgeous”, as he carefully wrapped his hand around it.

As I laid there with my hands behind my head, I asked even though I already knew the answer, ” Do I turn you on more than my sister did?”

Greg eagerly replied, “Oh God yes, I mean, you’re so beautiful, Scotty. And I just love your gorgeous patch of hair ,” as he removed his hand from my dick and stroked his fingers through my pubbies”.

Within seconds, he slowly worked his tender lips all over my hairless nipples and then down my smooth teenage body to my awaiting purple cockhead. The feeling of having another male caress me in such a way was incredible!