My family moved from Ohio to California when I was in High School. I instantly fell in love with California and enjoyed the opportunity to play outdoor sports year round. I excelled in baseball and swimming. We lived close to the beach to, so I learned how to surf pretty good. As the years went by I developed many great friends and was fairly popular. I missed some of my friends in Ohio but that's about it.
My parents were easy to deal with and I pretty much got away with a lot of crap. My little sister Chris, had it a little tougher than me but she managed to have her fun too. We watched each others backs and were very close. She was 2 years younger and had a lot of hot girlfriends. I banged a few of her friends and became very close to one Samantha. Chris was cool with this because she banged one of my best friends. Samantha was pretty wild when she got drunk, she liked to drink Margaritas and I supplied her with many. We did all kinds of things when we got drunk and naked. She let me bang her in the ass when she was on her period, which was more intense than her snatch. I always counted the days till she had to start using pads and tampons. I loved to screw her sweet ass and she didn't mind as long as she was drunk.
I went off to college and let the relationship between us fizzle out. I studied hard in college and did well. I also did good with the ladies and banged a lot of horny college chicks. In my senior year I started to get serious with one girl, Holly. She was athletic, smart and loved to suck cock. She was a very enthusiastic cock sucker, but could never take my cock all the way down her throat.
What she did love was the taste of my cum, way too much. When I shot big loads in her mouth, she would let it pool up in her mouth, savoring my milky love juice as long as she could before she swallowed it. Then she would try to kiss me right after and I always pushed her away. I could never understand why she craved my cum so much, but one day in the future I would figure it out.
After graduating college, I landed a good job that paid well. I soon had my own condominium and things were looking bright. Holly lived about 30 miles away and we spent almost every weekend together.
Most of the time she came to my place for the weekend to fuck my brains out, once in a while I went to hers. She shared an old house with two hot flirty roommates. Her roommate's always tried to seduce me when she wasn't looking. Her roommates were a few years younger than Holly and super sexy. They would prance around the house half nude all the time and flash me all kinds of skin. I always loved the free shows, when Holly was doing chores or checking the mail.
Holly and I were pretty close but there was one thing she wasn't into. She wouldn't take it in the ass. She didn't even want to try and when I pressed her she got pissed off, so eventually I let it go. The relationship was falling apart, especially on one afternoon when she caught me making out with her roommate.
Her roommate Courtney, had the nicest toned ass I've ever seen and flirted with me more and more. She said she'd let me fuck her in the ass if we ever got the chance to be alone. I guess she found out from Holly that I wanted anal and Holly didn't.
One Saturday afternoon I was watching a baseball game at her place, Holly left me alone with Courtney and went to run some errands. Immediately Courtney came on to me when Holly left. She came out of her room wearing the sexiest purple bra and thong. I got and instant hard-on when she walked in, then she came up to me and sat on my lap. We started making out like horny teenagers, it was getting very hot. She gabbed my cock and jerked me as we made out. I slid my hand down her smooth ass crack and began to massage her tight ass hole with my middle finger, that's when Holly walked in. Courtney jumped up and ran to her room and Holly started screaming at me to get the fuck out. That was the last time I saw Holly, or her roommates.
I was bummed out and felt stupid for messing around with her roommate. I threw myself into my job and focused on work and exercise. My boss recently hired a new big guy named Brad who was given the vacant desk next to mine. Brad is 6'2", very good looking guy with a slightly muscular build. Like me he loved sports and was a star athlete in High School. Brad is 26 years old like me, and just got divorced from his High School sweetheart. We had a lot in common, more than I knew at the time.
We had a lot of fun on the job and began to hang out after work. Brad was very humble guy and always dressed sharp. After getting to know him better, I could sense he lost a little of his confidence. He really was a very kind, sincere person. I wanted to help him through his divorce and help him gain his confidence back. Although he had no kids with his X wife, he was heartbroken. He found out she was having an affair with her boss and was crushed. She dumped him for a rich older guy and moved in with the home wrecker.
As the weeks went by, we became closer, he seemed to be getting over his divorce and began to laugh a lot more.
We went on bike rides, went swimming and generally had a great time together. He looked nice in speedos and filled out the front pretty good. He also looked great in bike tights, so I bought some just like his. We also loved watching comedy shows like Impractical Jokers and silly slapstick movies.
He was coming out of his shell and began to open up about his personal life more.
He had the same complaint I did with my X. No anal sex, ever. We talked about it and thought it was funny we had the same problem with our X's. I told him about Samantha, my anal sex queen from High School and he wanted to hear every detail. He had a girlfriend in college that would give up the booty once in a while, which he admitted was the best sex. He also said that as long as she was fresh out of the shower, he loved licking around her bum hole. He said it made her crazy for him and it turned him on big time. He claimed it gave him a monster hard on in no time.
"What's the big deal, as long as you take it slow at first and let them adjust to the new sensation. Some chicks are just too uptight to try. They think it's disrespectful to their pussy's or something."
"I know, some chicks get really pissed off when you hit them up for a little backdoor action."
"You got that right, you think we were asking to shove a baseball bat up there." We both laughed.
"Brad you are hilarious. Who writes your material?"
"It's you Mike, you inspire me to be my goofiest."
"Thanks, I appreciate that." I replied with a chuckle.
He always cracked me up with his comments and after our anal sex talk, we soon began to talk about anything on our minds. There was no holding back on any subject anymore.
One Friday night after work at his place, we were drinking beers, sitting next to each other watching silly videos again. Then a video of guy deep throating a banana came on, it was funny but kind of awkward to watch with him. We laughed hysterically when the guy choked at the end.
"That was fucking crazy Brad, have you ever seen that one before?"
"I've seen some crazy shit online before but never seen the deep throat banana man."
"Are you sure?" I poked at him.
"Awe come on Mike, you know I've never been gay."
"I don't know that for sure." I teased at him.
"You fucker, shut up." He said jokingly and shoved my arm.
I was a little drunk and feeling silly, so I went to his kitchen and grabbed one of his banana's. I came back in with the banana hidden behind me. I whipped it out and put down to my crotch and wiggled it.
"Hey big boy, I have a surprise for you." Teasing him like this, for the first time. It was all fun and games and he knew it.
"Come on Mike, your drunk."
"I know I was just messing you bro, I know your not gay."
I've never been gay either; but if I had to, Brad would be the perfect candidate. He had a sexy ass and a great smile. I put the banana back and we resumed our silly videos. We ended up getting pretty drunk that night, so he let me sleep over for the first time. He gave me a blanket and pillow and I fell asleep on the couch. The next morning I woke up and saw him across the room coming out of the bathroom, he was completely nude. I couldn't believe how big his cock was, it was like 7 inches soft.
He must of thought I was still asleep and when he glanced at me, I pretended I was. He walked around the kitchen for a minute then went back to his room. Brad sure had a big cock, I can see why his X-wife didn't want that going up her butt.
I got up a few minutes later to take a leak and I was stuck with a boner that wouldn't let me pee. I couldn't pee so I leaned forward and bent my hard shaft down to drain my lizard. When I came out Brad was in the kitchen wearing sweats, no shirt and making coffee. I was glad he wasn't nude anymore. It would of been hard not to stare at his big cut cock.
"Good morning Mike, you sleep OK?" He said kindly.
