A First Time for Everything

Driving down the road only blocks from my destination, I begin to have second thoughts. Here I was a 28-year-old man, good job, great friends, and a sexy girlfriend. Now I was about to risk it all for a chance at a fantasy that had haunted me for months now.

I was about to have my first homosexual experience. I had wanted this for so long and now I was only minutes away. The butterflies in my stomach were going strong as I rolled closer to Jeff's house.

Jeff was an 18-year-old guy. He was still in High School and was completely out as a bisexual. We chatted, emailed, phoned, and traded pics for months, all behind the back of my girlfriend Allison.

Jeff was 6'1, 175 pounds, short brown hair, and beautiful blue eyes. He worked out and played a couple of sports at school. He was in very good shape. His chest was so sexy and strong. Jeff was smooth, just the way I liked. His cock from the pictures he sent was about 7 inches long and cut. It was one of the most beautiful things I had ever seen.

As for me, my name is Brad. I'm not nearly the hot specimen that Jeff is. He doesn't seem to mind though. He just wants to be with an older man. I'm 5'10, 180 pounds, black hair, and brown eyes. I have some extra weight on me that I would love to lose, but I'm not all that bad. My chest has some light hair sprinkled over it and is still pretty attractive. My cock is my best feature. It's 8 inches and very thick. My girlfriend Allison can't get enough of it.

My brand new dark blue Chrysler PT Cruiser rolled up to Jeff's block. I scanned the addresses looking for 2367. There it was, a cute white house with a nice garden in front. I parked across the street and took a deep breath before walking towards his house. I have to admit, I was scared. I thought crept through my mind. What if Jeff had lied about everything? It would have been easy to steal someone else's pictures. I would just about die if Jeff weren't who he said he was.

I was at the door now. Thoughts were racing through my head at a very rapid pace. I could still bail if I had to. It wasn't too late. I shook my head and forced my hand to the buzzer. I pressed and it rang. My heartbeat was going crazy. This was the most craziest and exciting moment of my life.

The door opened and there stood Jeff. He looked just as the pictures suggested. I was relieved. One worry down.

"Hey, you must be Brad," Jeff said through the screen door.

"Uh, yeah, that's me alright."

I walked into his house. His parents and siblings were gone for the weekend, so it was just he and I.

"Brad, let's sit and get better acquainted," the high school senior said to me. I eyed his tight butt as he sat on then old couch.

"So....", I managed to say. I was such an idiot.

"Brad, you look a little nervous. Don't worry I won't bite. Unless you want me too."

We both laughed at that comment. It eased the tension a bit.

"Yeah, I am nervous. This is all so new to me."

"Don't be. I'm the same guy you've written to, talked on the phone for months. We are just gonna take our relationship to the next level."

"Yeah, I know. Nice place you got here," I blurted out. I was still nervous.

"Brad, sit next to me. We both know this is why you're here."

Jeff's hand patted the space right next to him on the couch. I smiled sheepishly and sat next to the 18 year old.

"Can I put my hand right here?"

Jeff put his hand high on my thigh. My black jeans felt as if they weren't there. I could feel the heat from his hand. Jeff then leaned over and kissed my forehead, my nose and brushed his full lips against mine and smiled. Damn this boy knew what he was doing. I was putty in his hands at that point.

"I'll go slow for you Brad."

Once again he leaned his cute face over towards mine. His lips locked onto my lips and we were kissing. Very slowly he kissed me, no tongue yet, but very sensual. His hands were running along my thigh making me so hot.

Then we started. His tongue flew into my mouth and my tongue instinctively did the same to him. We were making out. My hands were caressing the hair on his head, his hands along my back. I was making out with another man. My mind was delirious as we went at it for several more minutes.

Jeff then stopped and smiled. He was so adorable. His blue eyes and cute button nose drove me crazy. This is the man I was going to fuck. No, the man I was going to make love to. He slipped his hands under my tight black T-shirt and began taking it off. I raised my hands as he slid the shirt up. Before slipping the shirt off, he gently kissed my armpits. Shivers ran through my body. Now, totally topless, Jeff began his work on my already erect nipples. His hot tongue lathered them and sucked on them, as I never knew I wanted.

RINGGGGGG!

The phone rang. It startled me and briefly woke me up from my dream state. Jeff whispered something about the answering machine and continued licking my nipples and kissing my neck.

The answering machine picked up.

"Jeff, this is dad. Pick up the phone, I know your home. We need your help. We left the tickets on the bedroom dresser. Pick up!"

Jeff slid off me and towards the phone. He took the cordless to another room and I just sat there catching my breath.

A couple minutes later, Jeff came into the living room swearing.

"I'm so sorry Brad, but I gotta drive down the airport and give my parents their plane tickets. There flight was delayed so I have time, but I gotta go now."

I was shocked. I got up and began putting my shirt back on and heading for the door.

"Hey sexy," he kissed me, "I'll be back in an hour or so. Hang out here. My house is your house."

"Really, you still wanna do this?"

"Brad, I couldn't wait for this moment for months. Of course I want to do this. I want you."

I smiled. This was so surreal. Another man was telling me that he wanted me!

I kissed Jeff passionately as he went out the door. I watched as he hopped in his old Chevy Nova and drove off.

Dejected and still horny, I had no idea what to do. Kissing and making out with Jeff was so hot and now I'd have to wait. I sat down on his couch and thought about what to do. I decided to snoop around the place.

I walked into Jeff's room. It was the normal teenagers room. There were posters of hot girls, bands, and sports pennants everywhere. His bed was unkept and he had dirty laundry lying across the floor. At his desk was his computer. The very same machine that we first connected. It was already on so I decided to connect to the net. I checked my e-mail and then began searching for some hot gay pics.

That's how all this stuff happened with Jeff. I was horny and pissed off at Allison for not wanted to have sex. I had been bi curious for a while now. I hadn't any experiences at all, just my fantasies. I'd look for pics on the net of hot guys blowing each other. Men kissing men turned me on as well. I posted a few ads, but none of the men appealed to me. I wanted a guy with a great body, cute face, and a horny appetite. Personal ads weren't working so I hit the gay/bi chat rooms. I'd cyber with these men, as I'd masturbate with one hand and type with the other. In one of these chat rooms, I met Jeff. We chatted and he seemed cool. Jeff was pretty near where I lived, only 20-30 minutes away. I will never forget when he sent me his picture. I was in awe. He was hot! His pic consisted of Jeff with his shirt off showing me his awesome chest. He had on plaid boxers with a little surprise sticking out. You could see his penis, not all of it, but enough to get you thinking of how it would taste in your mouth.

Jeff and I became fast friends. We e-mailed each other almost everyday. We shared fantasies and told each other of our sex lives. Jeff was bi and very out. His parents, friends, and his whole high school knew. Most of his experiences were with men. Jeff would explain in breathtaking detail of the hot nights he would spend with the athletic jocks and horny brains at school. I remember asking him why he never told me of his exploits with girls. He'd explain how the girls at school thought he was disgusting for being bi. I later began to think that was just an excuse. Jeff never got very excited when I talked about fucking my girlfriend Allison.

Weeks past and I finally sent some of my racy pictures Jeff's way. He loved them. He told me jacked off looking at my body almost every night. We then began our phone relationship. I was falling for this boy and hearing his sexy voice only made it worse. The two of us engaged in some pretty heavy phone sex along the way. Telling each other what nasty thing we wanted to do to each other. Jeff would tell me that he wanted to sink his cock into my tight round ass. I told him I wanted to slide his cock deep into my mouth and swallow all his teenage cum. We did this for over a month and all without my live in girlfriend finding out.

Jeff began to talk about getting together and backing up all the talk we made to each other. Being inexperienced, I was scared. Having cybersex was one thing, meeting was another. I wasn't sure if I was ready yet. Jeff kept pressuring me for weeks, promising nobody would find out. I finally gave in. I had realized that I really wanted Jeff. I wanted to feel a man's naked body next to mine. I wanted to experience sex with a hot young stud.

That brings us up to this weekend. I told my girlfriend Allison that I was going fishing with some buddies. I had to tell my buddies to back up my story. They of course wanted to know why. I didn't tell them about Jeff, but hinted that I would be getting some. They wanted to know all about "her" when I got back.

This leads me to where I am now. I was in Jeff's room with my pants down looking at gay pornography. I'm stoking my 8-inch cock furiously trying to get off before Jeff came back.

"That guy's ass is good enough to eat, don't you think Brad?" a strange voice startled me from behind. It was Jeff and he was smiling from ear to ear. Just adorable.

I got up and began pulling up my pants. Jeff wagging a finger at me told me to leave them down. He stepped towards me and cupped my naked ass and kissed me like I've never been kissed before. It was so soft, wet, sensual, and yet so masculine. Jeff layed me on his bed and continued probing my mouth with his tongue. His hands had found my manhood and were gently stroking my cock. He got up from me and winked and left the room. What now, I thought?

My teenage lover came back with a bottle of wine. Jeff popped the cork and took a swig. He passed the bottle to me and I did the same. He then kissed my lips and we both tasted the strong flavor of the wine on our tongues. He once again removed my shirt and kissed my nipples. I loved the way he was pleasing me. My eyes closed and I cooed encouragement toward my 18-year-old lover.

"Ooooh," I cried as a cold liquid fell on my chest.

I looked up and saw Jeff slowly dripping the wine on my chest. He smiled when our eyes met and hurried down to slurp up the rich juices. He then licked his way down my chest to my tummy. He stopped and dripped wine in my navel. Jeff's tongue sucked the juice up while fondling my balls.

I cried in pleasure as I felt Jeff's mouth inch down my treasure trail and between my thighs. He kissed and licked the sides of my cock. My member twitched and was about to explode as the sensations of another man licking my penis was too much. Then I felt the cool wine droplets fall on my cock and balls. The coolness of the wine halted my cock's pending eruption.

Jeff smelling my hot sex along with the sweet smell of the wine slid my thick penis into his mouth. His mouth was like a sauna, hot and steamy. I felt his tongue caress the sides of my cock. The room was getting hotter, my head started spinning, and my cock was as hard as it ever was. Jeff was fucking my cock with his mouth. My golden brown balls were smacking up against his face while I was moaning and groaning in absolute rapture.

"Uhhh Jeff, I'm gonna cum, ohhhh, yes, this is so good, ahhhh, yessss"

Jeff slipped his lips off my rod as I came. My orgasm shook me like a freight train. I came so hard and long that I totally forgot about Jeff. When it ended I smiled as I saw Jeff's face moving towards me. His face was covered in white slimy cum. It was all over his eyes, nose, and lips. It was the hottest thing I had ever seen. Cum was dripping off his face as our lips met. As we kissed I tasted my own cum in Jeff's mouth. It tasted salty, but good. I began to clean my lover's face, slowly by surely enjoying the taste of cum with each lick. I could only imagine was Jeff's cream would taste like.

After finishing my cleaning, Jeff slid down my sweaty naked body and began to suck on my balls. I felt it and it felt good. Unfortunately my cock was spent. The poor guy had been worn out by an experienced cocksucker.

Jeff lifted my legs up in the air and began to devour my asshole. I could feel his tongue probing me, moistening my anus. It was a whole new pleasure in which I've never experienced. It looked like it was going to be that kind of day.

My eyes were closed and I felt like I was in a dream state. I quickly awoke as I felt the tip of Jeff's cock enter my ass. He was gentle and patient, but my ass was tight and the pain came quickly as he eased himself in. My asshole expanded to make room for Jeff's penis. It stretched and I winced as he continued entering me with his 7-inch cock.

Then Jeff stopped. He had filled my ass up. I could feel him inside me and with a little fear and a lot of excitement; I waited what was to come. Jeff began to pull out and then back in. Through the pain I began to feel pleasure. Seconds later the pain subsided and all I felt was joy of having a big fat cock in my ass.

Jeff began to quicken his pace. In and out, in and out...I began to moan his name. Jeff, who up to this point hadn't said a word, began to talk.

"Oh yes, I'm fucking your hot ass!"

"Yessss," I cried.

"Your so tight, uhhh yeah, Brad, how do you like your first ass fucking?"

"Ohhhh, yessss, I love it!"

"You're my little bitch aren't you? You need my cock!"

"Yesssss!"

"Say it!"

"I need you hard cock, ohh yesss, faster, I'm your bitch, fuck me Jeff, fuck me!"

Jeff was pounding my ass furiously. His balls were making loud slaps as he thrusted into me. I was moaning Jeff's name, as he was mine. We both were in total ecstasy. I was fingering my nipples and Jeff was stroking my cock as he fucked me. My cock was back and ready for more.

"Uhhhh, yesssss, Brad, ohh, your ass is so good, I can't hold off any longer, uhhhh."

"Jeff! Oh yes, Jeff! Fuck me like your little slut. Cum in my ass. I wanna feel you hot cock cum inside me, ohhhhh Jeff!"

My cock exploded once again. It was pointing up in the air and cum was flying all over me. Jeff, still stroking me stuck out his tongue and caught a few drops of my cum. This proved too much for Jeff as I heard him moan loudly, his eyes rolled into the back of his head and he came.

I felt the muscles in his cock spasm and warm liquid spewed into my body. Stream after stream flowed as Jeff moaned and cried. I could feel the warmth of his cum in me. My cock was still spasming as he dumped his whole load in my ass.

Suddenly Jeff was done. He slowly pulled out and I heard a pop when his cock left my warm ass. I could feel cum dripping out of my asshole as Jeff laid next to me. He still had his shirt on so I quickly remedied that and sucked on his erect nipples. Jeff was exhausted. Quite frankly so was I. Both of us on our back with flaccid cocks looked at each other and kissed. I whispered the words "Thank You" to him. Jeff put his finger on my lips to keep me quiet and kissed me gently. We rolled up next to each other and melted into each other's arms. In that position we fell asleep, two naked men, holding each other after the most intense most electrifying sexual experience of our lives.

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Thanks for reading my story. If you have any ideas for future stories or just comments in general, please send them to me. I love hearing what you think. Thanks