Freshman year of high school I secretly had sex with one of my senior brother's friends about twice a week. Sophomore year I managed on the few times a year that he would visit and the long winter and summer breaks where we practically had sex every day. I knew he was having sex senior year and during college but he said it was all with girls (we're both bi) so I was fine with it. Junior year, though I couldn't wait for him to come home and I constantly craved sex so I managed to get it from the most unexpected source: my best guy friend.
We were at a friends house watching a movie and I was silently massaging his shoulders while he sat on the floor in front of me (he really likes massages so this was not uncommon for any one to give him one). After a while I moved my hands under his sweatshirt then under his t-shirt and began to massage his bare skin occasionally reaching down to his nipples. Soon we were walking home and I called to pat:
'Hey want to sleepover at my house'
'It's a shorter walk so I may as well' he responded
At my house we were sitting in my room talking while I lied in my bed and he lied on the floor.
'Hey I'm not really tired do you want a massage?' I said
'Sure' he said
'K. get on the bed take your shirt off like a real massage' I said 'I'm going to go get some oil'
When I came back he was lying shirtless face down on my bed. My cock quickly stiffened so I rearranged it under the band of my shorts. I began to slowly lather the oil on and massage his neck and shoulders. I moved down to his lower back and began to massage his hips
'When I was in Hawaii all we wore was a towel when we got massages' I said
'Good thing we're not in Hawaii' he responded
'Yeah but it was so much better' I said grabbing the towel by my feet, throwing it over his butt and I began to pull his shorts off. They were down by his ankles when he grabbed them.
'What are you doing? I can't just be naked what if your parents walked in?' he said quickly
'It's fine they're out tonight don't worry' I said pulling his shorts off completely then taking his boxers.
I could tell he was uncomfortable but my cock was craving sex so bad I could not stop even if he was a straight guy just touching his ass would be enough. I began to massage his calves. He started to moan so I moved up to his thighs then to his upper thighs until I was touching the towel. I slowly massaged the towel up a few inches then decided to go for it. I began to all out squeeze and massage his ass. He tensed up and pushed down the towel.
'What are you doing? That's my ass!' he said
'Trust me! They did it in Hawaii, it felt amazing' I replied. Surprisingly, he put his head down and relaxed his butt muscles. I pushed the towel up on to his back to his ass was completely exposed. I was disappointed not to see his balls below his ass but he must have tucked them underneath himself. I was really grabbing his ass cheeks and pulling them apart so I could see his very tight, unvisited ass hole.
I pulled the towel back over his ass and told him to flip over. Without any hesitation he did so and I told him to close his eyes. I began to massage his chest then I moved down to his abs and right below his belly button. I used some self-restraint and moved down to his feet and began to massage those. He suffered from shin splints so I rubbed his calves and shins some more before moving to his thighs. Nowhere else to go, I went for it and put my hand on his cock and felt it quickly become harder. I looked at his expressionless face, eyes still closed and expected a response. I took this as a good sign and I began to rub up and down his shaft I pulled a pen from my bedside table that I knew was exactly the length of my dick (six inches) and placed it beside his cock. He had at least 2 ½ inches on the pen maybe 3 ½ so I guessed his dick was about 9 inches long. My sex buddy, Dave, only had a 5 ½ inch long dick. Using the end of the towel I measured his girth and found it was equal to the pen, 6 inches!
I put my mouth on his cock and began to suck him. After a while I kissed the pubes right above his cock and said 'Are-you-into-girls-and -guys' kissing him between each word and ending on his Adam's apple
Silent until know he responded 'Sexually attracted to guys. Sexually and emotionally attracted to girls'. He paused for a while then asked my favorite question a straight guy (now bi) can ask you 'do you have lube?'
I got the lube and applied it to his cock.
'Have you had sex before?' I asked knowing he may have gotten head.
'No. Nobody has touched my penis till now' he said quietly
'What a waste of such nice big meat' I said
'Yeah. A waste until tonight' he said turning me over and forcefully placing me on the bed. He struggled at using his virgin cock but eventually got it into my asshole. It felt like three of Dave's penis were being put in my ass. I moaned and he kept doing it. He did it until he came.
'Do you want me to fuck you?' I asked
'Nah my asshole is too small' he replied
My favorite part was that after we were done and although it may have been uncomfortable for him he got under the covers naked pulled me in to him and spooned me while we both rubbed my cock until I came. We laid there naked all night and the next morning he got up and I dressed him and he left. Both of us were uncertain of what laid in our future