I’m not gay but I did lose my virginity to a guy.
When I was 7, a boy moved in with his single dad next door to us. His name was Jason and he was a Native American boy.
We became friends instantly and before long we were having sleepovers and eating dinner at each other’s apartments.
Jason and I stayed friends all through high school despite him and his dad moving out of the neighborhood. Fortunately he was only 2 towns away and we didn’t go to the same school but we could still hang out on weekends.
By the time we got to 10th grade, the secret was out, Jason’s dad was gay. It was only a year earlier in 9th grade that Jason made an attempt to.. oh let’s just say “get physical” with me. Now, I should preface this by saying when we were 10, we started “exploring our sexuality” together. It was wildly innocent for the first few years. Starting with I’ll show you my penis if you show me yours. It took us a solid 8 months before that turned into “I’ll touch yours if you touch mine”.
We never made it past just two curious boys masturbating together, until one night in 9th grade. I was sleeping over at his house and while we were alone in his bedroom he leaned in and kissed me. The kind of kiss where his tongue was in my mouth. I just went with it. In the moment it was kind of hot. If any other guy would’ve tried that with me I would have knocked his teeth out but since Jason and I had a history, I just kind of went with the flow.
Jason mistake that for me being interested in something more. I wasn’t at that time.
Fast forward now to 11th grade and Jason is now not only out of the closet but sometimes even cross dressing. Entirely in private though. I’d still sleep over at his house on a regular basis. I hated my home life so anyone I attach myself to, I would. Jason had the entire basement to himself and a massive King sized bed. Yes, we shared that bed every time, and even after he was out of the closet, not only did we sleep in that bed together but always in our underwear, sometimes even naked.
It was a Friday night and I had arrived at Jason’s house after my football game. I had a particularly good game that night and was eager to get over there to tell Jason.
It was around 11pm when I got there and we headed to his bedroom in the basement. In the weeks prior, we had rehashed the conversation about the two of us being a thing. Even in secret, I wasn’t sure I wanted a relationship like that with him. So, it wasn’t long after I got there that the topic casually came up.
Normally I would change the subject or make a joke about it. That particular night I was in a different state of mind. Playing a football game and then playing exceptionally well that night, I was a bit gassed up if you know what I mean… I was horny!
I decided I was going to take a quick shower. I was still sweaty and dirty from the game and smelled something awful. Despite my musky odor, Jason stopped me before I headed upstairs to shower.
“Just think about it…” Jason said locking eyes with me
“Trust me when I tell you I think about it all the time.” I replied
Before I could escape, Jason grabbed my wrist and leaned in and kissed me unexpectedly. Just as he did two years earlier. Now, full disclosure there was a lot of kissing between us in that time frame. We’d make out and give each other blowjobs from time to time.
As I showered all I could think about was doing it. I wanted to go back downstairs and bend him over so bad but I knew I was all jazzed up and needed to settle down before I did something I was going to regret. So, I turned that hot shower into an ice cold shower. It was so cold but my mind was still fixated on what I had waiting for me.
When the cold water didn’t slow me down, I made the decision to just jerk off right there in the shower. It took all of 10 seconds before I shot a wad all over the wall.
As I exited the shower and began to dry myself, my breathing slowed and I began to mellow out. I remember thinking to myself how I was definitely not interested in sex with Jason but I was totally going to try and get a blowjob out of this.
As I said, Jason and I casually would suck each other off every once in a while. That secret alone was a lot for me to lose sleep over. It was the 90’s and homosexuality was not accepted well, especially amongst teenagers. I lost a lot of sleep over it because the greater secret was that I almost certainly enjoyed it more than he did. On both ends! Jason gave fantastic head but I absolutely loved sucking his cock! I loved the way it smelled. Tasted. I loved how hard it got but it was still covered in the softest, smoothest skin on the body! I loved it!
As I left the bathroom and began to make my way downstairs, I noticed that Jason’s dad’s bedroom was open just a crack. To this day I have no idea why I stopped, turned around and looked inside but what I saw changed my life.
I quietly pressed my left eye to the crack in the door. The room was dimly lit but I could see everything just fine. I saw Jason’s dad on all fours with his new boyfriend Mark fucking him from behind.
Jason’s dad was just a schlubby guy with nothing special about him but this Mark fella was a different story. Mark was in his early 50’s and had dark hair, a decent body, a thick black mustache with some grey stubble, a patch of chest hair and one of the most impressive cocks I’ve ever seen!
I couldn’t take my eyes off Mark fucking Jason’s dad. The smells, the sounds they were making still echo through my head 30 years later. I only watched for a minute at the most but it felt like an eternity. I only had a towel wrapped around my waist, no clothes. My cock was so hard that it pushed the towel open. I was only 17 but I had never been that turned on before and maybe never since.
I tossed the wet towel back in the bathroom and made my way through Jason’s living room stark naked with the hardest erection I’ve ever had.
As I entered Jason’s room there’s a couple scented candles burning and the lights are out. Jason is sitting on the edge of the bed with his now long hair tied back. He’s wearing a very sexy black women’s silk lingerie piece.
“Oh my god!” He chuckles seeing me walk in with an erection. “Wow, is that for me?”
“Mmhmm..” I quietly say with my entire body trembling
Since Jason told me about his love of wearing women’s clothes, I had gotten very used to seeing him in them. As I said he only did it in private and I had made a new rule that when we exchanged blowjobs, he had to be dressed in women’s clothes. I just preferred the optics, you know?
Jason and I crawled into his bed together and draped the sheets over us. I don’t think either of us took a breath the entire time. Both of us trembled as neither of us knew exactly what was going to happen. How far were we going to go?
Our legs entwined first. He had shaved his legs! That was a first. Our hands began to explore each other’s bodies as we scooted up as close as we could to each other. Our cocks rubbing against one another, our tongues began to swirl as well. Suddenly the was the moment where we weren’t just fooling around anymore. The groping and kissing became intense. There was this intoxicating feeling that I was or about to fall in love. We both noticed it. We spoke of it many times afterwards.
“I want you so bad!” I moaned in his ear
“You have me!” I whispered back
I rolled on my back and reached for a tube of lubricant he kept in his side table drawer. As I dug blindly for it in the poorly candlelit room and grabbed the lube I felt Jason’s cold hand and warm mouth wrap around my cock. I squeezed the tube almost hard enough for it to explode in my hand.
Jason quickly sits his girlish figure up and straddles me. He takes the lube from me and squeezes a bit on the tip of my cock. It warms to the touch and my cock begins to tingle. He massages the rest on his asshole and presses my cock against his hole and slowly sits down on my cock.
Jason began to slowly grind and move up and down on my cock. Instantly I began thinking of watching Mark fuck Jason’s dad. Seeing that removed whatever was in my head stopping me from exploring sex with guys, Jason in particular. Whatever it was, put me over the edge.
OP
Suddenly I look up at Jason and as he’s riding me, he has a firm grip on his dick and he explodes all over my stomach and chest! That was all I needed. I began thrusting upwards and squeezing his hips as hard as I could. Seconds.. yes, seconds later I unloaded everything left in my balls inside his ass. I’ve never felt so good in my life! What a feeling! The intensity. The passion?! Who knew we’d suddenly have feelings involved?
We ended up having sex 3 more times that night. I was completely exhausted. It was unbelievable!
The next night I slept in my own bed and I had a sex dream. I only remember a flash of it but it was me having sex with an older man and in the flash, I call him Daddy. So when I woke up with a raging hard on, and I began to play with my dick, I started thinking about Mark and Jason’s dad. Well, more specifically Mark. I couldn’t stop thinking about his hairy chest and his mustache. I wanted to fuck Mark. Well, more specifically, I wanted Mark to fuck me!
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