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

When we reached the top floor and exited the elevator, we walked down a hall to the penthouse. Greg explained the penthouse was actually a large multipurpose room with about six separate bedrooms, wet bar, kitchen and a huge dinning room. He added that it could be rented by any resident for $500 a night and by reserving it 30 days in advance.

Just as we got to the entrance, there was a doorman standing in front to check us off the guest list and to let us in. When he opened the door and we walked through the foyer, my jaw nearly dropped to the floor. There before us stood a whole room full of naked men wearing nothing but black formal tuxedo ties lounging around socializing with cocktails in their hands.

It was what I would call a formal nudist party! I could believe my eyes at first, but Greg just grabbed both my shoulders from behind and exclaimed, “See, I told you it’s a special party.”

I was so shocked, I was speechless. It was the strangest thing I'd ever seen looking at a room full of naked men with their hairy dicks hanging out talking to one another as if it were no big deal. But I had to admit the crowd was very good looking indeed. Most the men appeared to be between their mid 20’s and 40’s with trim bodies. And judging by their mannerisms and appearance, they were strictly upscale professionals like Greg.

Greg quickly grabbed me by the hand and led me into a room right off the foyer where the newly arrived guests were removing their clothes and checking them with a party host who was naked himself.

Well, I was so nervous, I was way too scared to take off my clothes. But Greg stripped off his then took mine off. As I stood there in the bare buff, Greg hugged me and said with a smile on his face, “Scotty, Relax! You're going to have a great time. I promise! After 20 minutes or so you won’t even miss your clothes. Now let me put this bow tie on you cause I want to see handsome it makes you look.”

I replied still shaking, “Are you sure, Greg?”

Greg exclaimed, “Heck yes I'm sure. If I didn’t think you would have a good time, I wouldn’t have brought you up here tonight. You'll fit right in--trust me.”

Greg straddled the tie around my neck and buttoned it. Once he was sure he had it securely fastened, he stood back so he could admire how it looked on me. He then buttoned one on his neck and said, “Come on, let me get you a drink--I want to introduce you to everyone and show you off,” as he gave me a kiss on my lips along with one of his darling smiles that always floored me.

He quickly grabbed my hand and led me out to the bar. I felt so peculiar walking into an open room completely naked wearing nothing but a formal black bow tie. Just as we were ordering drinks, we ran into Mike & Harold -- the two guys I met the day before. Mike had elegant gold & black name tags made for us and stuck them on our chests.

Once Mike had padded my name tag on, Harold looked me over and exclaimed in his very nelly voice, “We thought you were darling enough yesterday Scott at brunch with your clothes on, but you're even more darling with them off,” as both he and Mike chuckled.

Mike exclaimed, “Yea Scott, you are so adorable! Greg you better keep your eyes on him tonight,” as once again both of them snickered in their sissy nelly utterances.

I just smiled and blushed cause I didn’t know what to say.

But Greg jumped in with a quick comeback line and exclaimed, “Scott can have any guy he wants this evening as long as it’s me.” All four of us got a great laugh out of that comment.

As I looked around the room, everything seemed so strange. Here I was standing in an elegant penthouse with marble walls, plush carpet, beautiful chandeliers hanging from the ceiling, gorgeous mahogany bar, fine china & silverware, elegant white table cloth settings and the whole room was filled with naked gay men with black bow ties standing around with their hairy peckers hanging out. I thought to myself, “If my Mom could only see where I am now, she would probably pass out and who could blame her?”

Greg, Mike and Harold explained to me that Chicago had a gay nudist club already, but that this one was a private made up mostly of residents from the building, select friends and working business professionals. Moreover they made it clear that they were very picky about who they invited to join club and that their membership could be no greater than 110 people. They added that once a month, they met usually here in the penthouse, and held their party on Saturday night.

No sooner had Greg handed me a rum & coke while he talked to Mike & Harold, when three guys approached us who saw me strip at the night club the day before. They came over to say “hi” and to welcome me to the party. All three were very kind and sincerely warm. One guy, Kip, said, “Geeeze Scott, you were so damn hot dancing
around yesterday. I think every guy in the place fell in love with you yesterday.”
I gave all three guys a pleasant smile and said, “Well I had fun dancing and I'm sure glad I was able to help raise some money for such a good cause.”

Greg stepped in with a smile and said, “I bet every guy was in love with Scott too yesterday and probably tonight as well. But Scott belongs to me--so they can look all they want, but they can’t touch,” as everyone broke out in laughter.

Even though I thought what Greg said was rather humorous, I loved it when he announced that I belonged to him. I knew Greg wasn’t jealous even though he knew just about every guy there was checking me out -- especially my ass & cock.

After Greg introduced me to quite a few other people, he took me by the hand and led me down a hall to the bedrooms. Once again my jaw literally dropped to the floor when we poked our heads in the rooms and observed guys having open sex. There were three rooms alone where several groups of orgies were taking place. One guy who looked to be just a little older than me was down on all fours letting some older chubby man fuck his lights out. And there was no doubt by his facial expression and moans he was loving every second of it. I'd never seen anything like it in my life!

Greg explained that some men liked group sessions and enjoyed getting a little action in before dinner. Greg added that after dinner and once everyone got either drunk, bored or both, things got even hotter in the bedrooms and they most often spilled out into the dinning room and lounge areas.

When I asked Greg what would happen if the manager of the building found out about these nudist gay sex parties, he grabbed me by the hand and led me over to the second bedroom. When we looked in, we observed four guys fucking on a king size bed. There was also an older slim man in his late 40’s and a young guy in his early 20’s sitting on a sofa deep frenching one another hot and heavy. Greg yelled out, “Yo, Alex...you gotta a second ...I want you to meet someone.” The older gentleman looked at us, paused, got up and came over as Greg requested.

Greg said, “Scott, this is Alex.... Alex this is Scott. Alex’s company, Scott, owns this apartment building as well as a number of others in Chicago. And he is the principal partner in the corporation.”

Well, needless to say, I was shocked. I couldn’t believe that one of the owners of the building was gay and was in the nudist club having sex like the other gay men.

Alex smiled and replied, “It’s very nice to meet you Scott. Any friend of Greg’s is a friend of mine since he is our attorney and keeps both me and our company out of trouble,” as he gazed my naked body over several times with a huge smile on his face.

I had no idea Greg was the attorney for the apartment building. When I looked over at Greg with shock on my face, he just smiled and put his arm around me.

Alex then informed Greg that one of his manager’s informed him that three two-bedroom apartments were coming available in the building the following month and that Greg had first choice on any of the three if he wanted one. Greg was overjoyed by the news! He went on to explain to Alex about our past and my sister, and that we were now going to be living together in June. Greg added we needed an extra bedroom so that I could use it as my study since I would be going to college as well as a guest bedroom when we had company.

Alex jokingly said that having a good looking couple like us living in the building would definitely drive the value of his skyrise up.

He graciously excused himself because he wanted to go back to his hot little trick that was sitting on the sofa waiting for him. But he told Greg and me to get with his manager, Russell (who was gay himself and at the party somewhere) and have him show us all three apartments. He added that he would tell Russell to have whatever apartment we picked out both painted, re-draped and re-carpeted to our choice regardless of whether it needed or not.

Greg looked over with me with a huge smile on his face and said, “See sweetheart, we are going to have our very own place together just the way we want it. I’m so excited!”

With a huge smile on my face, I replied, “Well I’m really excited too Greg, I can’t believe how fast everything has happened already.”

Greg quickly hugged me, placed a quick kiss on my lips, and exclaimed in delight, “Don’t worry about it sweetheart---we are going to have a great life together, I promise!”

Of course I wrapped my arms rather firmly around Greg with joy. When he jokingly complained by asking if I was ever going let him go, I whispered in his ear, “Well, I will let go of you, but I want to hold you for a few minutes. And before I do, I want you to promise that we will fuck again tonight cause you felt so good when we did it earlier.”

Greg smiled and exclaimed, “You can hold me as long as you want. I’m all yours sweetheart and of course I promise we’ll fool around tonight.”

I couldn't believe all of this was happening to me. It was like a dream come true. All the years I had a secret crush on Greg was now a reality. He had chosen to take my hand and spend the rest of his life with me and not my sister or any other woman.

Just as I gave Greg a huge deep wet kiss, two guys walked by and said we were definitely the hottest couple at the party. Still embracing one another we both thanked the guys for their kind complement as we looked at one another with sure love in our eyes. No sooner had I finally taken my hands off Greg when dinner was announced. Greg interlocked our fingers and lead me down the hall to the dinning room.

The dining room was absolutely gorgeous! It was set for 200 people. Everything was strictly the finest--the finest bone china, silverware, crystal, table clothes, gold flowered centerpieces andwine colored candles. It was kind of odd dinning in such a formal elegant setting in the nude. Just as we sat down, Alex joined us at our table along with his cute little boyfriend and his manager Russell. Alex learned from Greg that I was considering Northwestern University among others to attended. He was so excited, he insisted that I go to his Alma-Mater especially when he learned I scored 1480 on my SAT’s and was carrying a 3.854 GPA.

Alex then exclaimed in sure determination, “Scott I want you to get with Russell in his office here in the building first thing on Monday. Russell is going to take you up to Northwestern and show you around. I’ll call the dean of students and have him meet you guys and give you a tour. He’ll process your application, Scott, and get you approved right away on Monday since he already has your application on file so you don’t even have to bother looking at those other schools. Then Russell can take you to lunch and show you around the city a bit...and then, when Greg gets off work, Russell can show you those apartments. Now, no “Buts’. Russell, tell Sidney and Leon (the two other managers) to cover for you on Monday cause you are
doing a little project for me.”

Well, needless to say, I was floored. I looked at Greg and he looked at me with a huge smile on his face. Greg squeezed my hand like he was telling me, “Let’s not pass this kind offer up, Scott. Alex is a powerful man so let’s take advantage of this and let him help you.”

Of course I agreed and reached over and gave Alex a big hug. Alex jokingly said, “Now you just make sure you keep Greg, happy Scott, cause I don’t want you guys leaving Chicago.” We all got a big chuckle out of that statement and then Alex toasted the fact that I was headed to Northwestern the following year.