Jake and I
After four years of marriage to my high school sweetheart, I was divorced and living in a new city (Miami). Sex with my wife was OK but I had these near constant feelings about how it would be to have sex with another man. I grew up Lowell, MA. As a teenager when I was home alone I would get naked and put on my older sister's bra and panties. I would fill the bra cups with balled up panty hose, then stand in front of a full length mirror and admire myself. Masturbation soon followed. When my sister went away to college and took all of her lingerie with her, my dress-up afternoons ended. I tried once to do this again with my wife's things but she was too petite and her things didn't fit. I thought about buying some in my size but I feared that my wife would somehow find them.
Now living in Miami I decided to explore the other side. One Wednesday night I drove up to Ft. Lauderdale. Once there, I used my cell to call a cab company. I asked the dispatcher for the location of a gay bar. Without comment or hesitation she gave me an address. I punched the info into my GPS and drove. I was nervous as hell as I walked into a gay bar for the first time in my life.
I waited by the door for my eyes to adjust the dim lighting. I surveyed the room and the patrons. The furnishings were upscale. Nothing cheap here. The men (no women) were, for the most part, upscale as well. Some wore jackets and ties. There were two gorgeous
CDs at the bar and a few muscle boys.
I found a small table for two in a corner from where I could see the entire room.
I ordered a diet soda from cute young guy in short shorts and a white blouse unbuttoned and tied at the midriff.
I was looking in the direction of the entrance when a familiar face walked in. It was Jake from my office. Jake, I had learned, was a real ladies man. But here he was in a gay bar nearly thirty miles from his home. What was he doing here? The question was answered when my cute server handed him a drink that he had not ordered then kissed Jake full on the lips.
I kept my head down, not wanting Jake to see me here. When he went toward the restroom I put a ten spot under my drink and bolted for the door.
Outside, I half ran to my car. As I drove home I thought, what am I running from? Jake was in that gay bar too, just as I was.
The next morning, as luck would have it, I ran into Jake at the coffee maker. We exchanged good mornings. He gave no indication that he had seen me the night before.
Later that day Jake stuck his head in my office. "Hey, newbie, you a Pats fan?"
"Sure, isn't everyone?"
"No, not in Miami. Listen, you're invited to a game party at my place Sunday. Come and watch the Fins kick some Patriots butt.""The game is at four, you in?"
He handed me a card with his home address and phone number on the back
"There'll be beer. If you want wine, BYO. Three thirty, no sooner, I'll be busy"
At three forty-five on Sunday I entered the lobby of Jake's condo. Security signed me in and pointed to the elevators that took me to the twelfth floor. When I got to his unit the door was open. I called out and walked in. Jake shouted back to close the door and that I was the last to arrive.
Inside, watching the big screen were black Jim, white Jim and Kevin. All from the office and I later learned, all played on the office softball team. As did Jake. The Jims and Kevin were holding bottles of beer. Jake had white wine and I had brought a bottle of Bordeaux.
It was a fun afternoon even though I was the butt of the jokes since the Dolphins were having their way with the Pats and won easily. The conversation went from sex to politics to the game, to sex and other sports and back to sex. Kevin said the he was exploring going to Yankee fantasy camp next year. That got a big laugh. White Jim's fantasy was to fuck Joanie, the leggy red head with the nice rack. She was new to the office and white Jim wanted to be the first to nail her. The others laughed at what his wife would have to say about that.
White Jim's wife must have been watching the game at home, since the minute the game ended, his cell rang. She wanted to know when he was coming home. They rode together, so black Jim had to leave as well. Next it was Kevin's wife. Same thing. Kevin apologized for booking. I told him to go ahead. I would help Jake clean up. The dishwasher was loaded and the tables and bar wiped down in minutes. Jake poured the last of our wine and took a seat at the bar. I sat in an overstuffed chair.
Jake began to chuckle.
"If Jim got ever got a shot at that redhead he'd chicken out. And Kevin talking about fantasy camp. That's because he hasn't run it by his wife yet."
Here was my chance to get bold. "I've got a fantasy"
"Well, I'm sitting in chair like this one and a guy walks up and stands in front of me. I reach out and rub his crotch. Then I go for his belt buckle..."
"Whoa, whoa, why are you telling me this shit?"
I had been looking down until now. I looked up and right at him. "I saw you at a bar in Lauderdale Wednesday night."
"Oh. Are you going to out me, now?"
"Thanks. Well, go on with your fantasy."
"I drop his pants and pull down his underwear and take his penis in my mouth". Here I pause.
Jake says " Go on, what happens next?"
"I don't know. I've never done it before."
"Then I guess you would like me to show you the way, is that it? Finish your fantasy, so to speak?"
"Yes, that's it."
"OK, what kind of underwear is your fantasy guy wearing? Boxers, jockeys, red bikinis? Got to make this fantasy complete"
I answer, "white jockeys"
Jake slides off the barstool and heads to his bedroom. "Be right back. Take off your shoes and socks"
My hands are shaking uncontrollably as I unlace my sneakers and pull off my socks. It's going to happen. I can't stop shaking.
Jake is back. He stops at the bar to finish his wine. He has removed the sandals that he had been wearing. He walks over and stands in front of me. According to my fantasy, the next move is mine, I take it. With a deep breath, I reach out with a still shaking hand and touch the front of his jeans. Getting bolder I rub the bulge. Another deep breath and I go for his belt and zipper. His jeans fall to the floor. I put my thumbs in the waistband of his jockeys and pull them out and over his penis then down to the floor. Jake steps out of his jeans and jockeys and kicks them aside. Now I am looking at the first live cock since high school gym class showers. None of those were erect and this one is right in my face. I leaned forward and took this beautiful cock into my mouth. At first I just held the head in my mouth. Jake helped by gently pumping it back and forth between my lips. When he stopped this, I took the hint and began to stroke his cock with my hands and lips. I must have been doing something right because I heard him moan. Then his knees buckled slightly and he put a hand on my shoulder for support.
He pulled away from my lips. "Let's slow down and get comfortable."
He took my hands and pulled me to my feet. He was totally naked now. He must have
removed his tee when his dick was in my mouth.
He said, "Come," and led me to his bedroom.
The bedroom was dimly lit. There was only the light from the hallway and the master bath. We stood beside his king-size bed and in front of a mirrored wall. Jake began to slowly undress me. When I was naked he moved behind me. When he kissed the side of my neck I tilted my head back rested it on his shoulder.
He kissed my neck again and motioned for me to lie down on the bed. Jake got on the bed and straddled my left leg. He then took my hands and held me spread-eagled. Then Jake was kissing and sucking my nipples. What a sensation. Something I had never experienced before. I arched my back trying to get more of my nipples into his mouth. Then he was kissing my neck again while tweaking my nipples, first one then the other. Jake kissed my ear, my neck, my cheek, my forehead. He then paused with his lips just two inches from mine. He moved as if to kiss me on the mouth. I guess he wasn't sure if I was ready for that yet. I was. I put a hand on the back of his head and pulled his lips to mine. Our mouths opened and our tongues we doing their dance.
When he kissed my nipples again I reached out a grabbed his cock. Jake stopped me. He said that this first time would be all about me, we could do him later. I didn't argue. I was the student here. The teacher knew best. We had been naked together for nearly fifteen minutes and he was yet to touch my raging erection. I thought that I might climax from just his kisses and caresses. I just closed my eyes and let things happen. He shifted position and was between my wide spread legs. He was tweaking my nipples with both hands now. Suddenly I felt warm breath on my cock, and then in an instant my entire member was in his mouth. I knew that I was going to cum soon and said so.
He stopped looked up and said "Yes, do it, cum in my mouth." Then went back to work with his mouth and tongue. It took just a few more strokes until I climaxed. He kept up the sucking until I was totally spent. I felt him swallow before he let my cock slide out of his mouth. Jake then moved to lie beside me. When we both said thank you at the same time we laughed.
I got up on one elbow gave him a quick kiss on the lips. "My turn now?"
"Sure, go for it"
I began with is nipples. Sucking, licking, tweaking, tweaking, sucking, licking and back again. I didn't have Jake's patience. I wanted his cock in my mouth again and went for it. I saw a drop of precum on the tip. I stopped to lick it away. Another appeared and I licked again. I wanted more and took it. I tried to get as much of his cock into my mouth as I could handle. I worked his cock as fast as I could. I was having trouble breathing. Jake said that I should breathe through my nose.
Good tip. It was easier now. I pumped and sucked but it didn’t appear that he was going to cum for me. I needed help and asked for it. Jake began to jack off with the head of his dick in my mouth. When he took his hand away and said that he was going to cum I again took as much of his cock as I could. I sucked and pumped and swirled my tounge on his rock hard cock for just a few seconds when I felt his cock jerk and I could feel his cum in my mouth. I held on with my lips until I was sure that he would cum no more. I was surprised that his cum didn't have much of a taste. I then swallowed my first load of cum.
Lying beside him again as before Jake said, "On three, 1,2,3, Thank you."
Together, we laughed again.
I had a question. "Why did you tell me to remove my shoes and socks?"
He answered that he knew that undressing me would be sexy. But pulling off another’s sweaty sneakers and socks wasn't very sexy. I had learned something else this night.
Gotta go now. Maybe I'll be here again to tell you about my next my next lesson from Jake.