It all started when I was about 15. I was a mid sized boy, 5'7, and I was always very curious about my sexuality. Ever since I was younger I had always wondered what It would be like to have sex for the first time, whether it be with a boy or girl didnt quite matter to me. Though I was curious about sex, I thought that my penis was a little lacking in size at six inches, so I always thought I might have to be gay to get pleasure from sex.
When I was 15, I got curoius about homosexuality. For a while I thought it was a phase. I would try on my sisters clothing, thongs, heels, the works. I would use tampons I found on the floor and put them into my ass to see what it felt like. And soon I learned to use other methods to pleasure myself.
It was a friday afternoon, I was on the floor of my room, pants around my ankles, with an old electric toothbrush in hand. I placed it against my anus to feel the virations of the motor inside. The sensation made my body shake for joy. So I did what I normaly did, and grabbed my penis and started masturbating. The combination of vibrations from the toothbrush and my hand upon my rob made the cum in my balls build quickly. I closed my eyes and bit my lower lip, imagining that I was fucking a man with a large dick, filling my ass giving me the greatest pleasure imaginable. I felt near orgasm when I opened my eyes and looked out the door of my room to see my friend Mike standing their in awe of what was going on before his eyes.
Mike was my neighbor. We had been best friends for as long as I can remember. He was about my age, close to 6 feet tall, dirty blonde hair, very attractive to me. Because we had been such good friends, we had a policy where we could let ourselves into the others house without knocking because we thought it would save time.
After seeing him I immediately turned off the tooth brush and covered my nudity up. Me and him had always joked about gays so I thought he would probably make fun of me for what I was doing.
I stood up and turned my back to him and pulled up my pants as fast as I could. My hands were shaking so badly I was having trouble with the button to my jeans. I fidgeted some more when I felt Mike standing behind me, his hands on mine. He steadied my shaking hands and pressed his body against mine. I felt the bulge in his pants pressing against my lower back.
I could feel his eyes boring through me, undressing me.
He spoke softly to me, "You know, Rob, its ok, what you were doing. Theres nothing wrong with wanting a little something for yourself."
His voice made my heart melt. I had occasionaly fanasized about what it would be like to have sex with Mike, and the idea that it might happen now sprung a new life into my penis.
I turned around and pressed my body against Mikes, stradleing his right leg. The bulge in my pants was up again, ready for some more action.
Looking into his eyes, I said "Mike, would you?"
He looked down at me, I thought I saw love in his eyes, "I was waiting for you to ask."
The next thing I know his pants and boxers are on the floor, my mouth wrapped around his eight inch dick. The taste, the smell, the feel. All of it made we want to go on like this forever. I licked, slurped, tugged, sucked, and just about everything else I had seen done to a cock in pornos. I could feel the tension in his balls. His dick started to spasm. He tried to pull away, but I grabbed his ass and he cumed right into my mouth, filling it with his delicious nectar. I had tasted my own cum before, but it paled in comparison to this. This taste was divine ambrosia, as if sent from god to give me pleasure.
Some cum dripped out of my mouth, some into my throat, I glazed his member with his juices, and swallowed watever was left.
I looked up at him and said simply, "Lubricant."
He smiled at me a smile that melted my heart and made me fall in love with him.
He picked me up and laid me on the table. He kissed me, thrusting his tounge into my willing mouth. I had wanted this kiss so much that it hurt. He stripped me of my boxer and tee shirt, and placing his hand on my six-pack, he slowly worked his cock between my cheeks and into my will ass hole.
The sensation was amazing. I had to contain myself from screaming, but allowed myself a long moan as his member went fully into my rectum. He slowly humped in and out, driving me crazy with pleasure. And as soon as it was slick enough, he humped faster and harder against my ass. All I could do was moan and squeek as his cock filled my ass with pleasure. I looked into his eyes and he looked into mine. For that moment the connection that we shared that would last us years.
He had one hand on my left ass cheek and the other on my penis, slowly jerking it along with the rythm of his humps. I could tell he was ready to come again and I myself was on the verge. He held me close as he gave one final hump and exploded inside of me. At that very moment, my own stream of cum emerged, soaking his chest and abs.
He leaned against the wall and allowed me to lick my own cum off his body. I could feel semen dripping from my ass down my legs but I didnt care. I was in a state of bliss. I was no longer had my virginity, It was taken from me by my best friend.
We slid to the floor and made out for what seemed like hours. Soon after he looked me in the eyes and said that he loved me. I respnded the same, just as we heard my front door open and my father walk in from work.
We scrambled to put our clothes on and turned on my playstation, sat down and played for a while, until Mike had to go home for dinner.
One night, Mike told me that his parents were working and his sister out with her boy friend so i could come over and hang out. We walked up stairs to his room, holding hands. I could tell what he was looking for by what he was wearing. He wore a white beater and boxer breifs, showing an attractive bulge at his crotch.
Now because we had such time for pleasure, I thought Id make it fun.
"Mike, you go into your room and get ready, Im going to get changed."
Mike looked at me quizicaly and complied by walking to his room.
Once I was sure Mike couldnt see me, I walked into his sisters room. His sister was around my height and size, but two years ahead of us, a Junior in high school.
I knew she had some nice clothing because I had seen her wear it around. Immediately when I entered the room, I was greeted by the smell of girl. Perfume was in the air mixed with nail polish and other female products.
I decided that I should put on a show for Mike. I went to the closet and picked out a nice pair of blue heels that strapped to my feet. Amazingly enough they fit perfectly. I placed the shoes on the bed and went to her underwear droor and pulled out a small pair of baby blue shorts. They were tight on me but that only helped. The I pulled out a white tank top with spaghettie straps and put it on. The went to her make up desk and applied baby blue nail polish to finish it off. I wanted to look as attractive to Mike as I could.
After I assembled myself, I walked with grace into Mikes room and stood at the door way. He sat at his computer looking at porn slowly jerking his schlong. He turned to see me and his jaw hit the floor. He was completely speecheless.
He walked up to me, cupped my ass in his hands and carried me to his bed, our lips locked all the way there. He layed ne down and climbed atop me. He grabbed the shorts I was wearing and pulled them to my knees and rubbed my ass with vaseline.
He put his dick into my anus slowly but steadily, and began humping. There was something different about this fuck. There was love in his strokes. I could feel that he was realy in love with me. So I decided to give it back.
Every time he came in, I went up to meet him. We lied there humping each other for what seemed hours until I came, followed by him.
He rolled over onto his back and lie there naked on top of the covers. I crawled up next to him and place my and on his chest and head on his shoulder. There we lied, speechless of what had just happened. We drifted to sleep.
The next morning we had realised that we had slept naked with the door wide open. Lukily his parents pulled all nighters at work and his sister was too wasted to notice. But still, after that close call, we decided to play it safe from then on.