This is the true story of how I lost my virginity and what might’ve sent me down the road to sex addiction.
This happened when I was 16, I’m 40 now but this story began earlier than that even. As I said, it is a true story. I’m not even changing names.
Our story starts in 1990. I was 10 years old and a new kid moved into the apartment down the hall from me. It was just him and his dad. His name was Jason.
It was just a week before the first day of school and he looked about my age. I was happy to see on that first day of school he was in my class. After I introduced myself, he mentioned he’d seen me around the apartment complex. We hit it off immediately. By Christmas we were thick as thieves.
By that time I had noticed that his dad was gay. There were always a man friend over at his house and he’d always seem to be staying the night.
Fast forward a few years and Jason and his dad moved into a new house two towns over. We now went to rival high schools. Just before he moved we had started fooling around a bit. Mostly I’ll show you mine if you show me yours, which evolved into masturbating together. We even practiced kissing, tongue and all. We both chalked it up to practicing for when we had girlfriends.
Soon after he moved I was staying at his house for the weekend and so was his dad’s boyfriend. Jason’s bedroom was in the basement of the house and directly below his dad’s room. We heard most of what was going on in there. We giggled a bit until Jason worked up the courage to suggest we jerk each other off. I was excited but tried to hide it but still agreed. The next night I brought up the idea that someday we should try to give each other blowjobs. We both were reluctant to do so but after a week apart we ended up awkwardly sucking each other’s cocks the following weekend.
The blowjobs went on for almost two years and the talk of anal sex came up from time to time but both of us were terrified to go thru with it. Me in particular. I had tried putting a finger in my ass in the shower when we began discussing this and it didn’t feel very good. That being said, now at 40, I love a finger in my ass!
Now to the story.. I was now 16, almost 17 and Jason had already turned 17. I was a fairly good third baseman for my school baseball team and we happened to be playing Jason’s school on a Friday night. Jason didn’t play sports as he had become more and more feminine over the last year and had come out to his family and me but no one else.
I saw Jason sitting in the bleachers watching the game and knew I was going to his house after the game to spend another weekend there. Which meant I was going to get at least a couple blowjobs. And, I was going to be giving a couple too. We had been sucking each other’s cocks for close to two years now and not only getting good at it but I was really loving it too. I love sucking his cock and getting a mouthful of cum as much as I love getting my cock sucked.
The game came to an end and instead of taking the team bus back to school, I walked to Jason’s house with him. We talked about how horny we were and he mentioned he had a little surprise for me. I don’t like surprises but I had no choice but to wait.
I had been thinking about anal sex more and more with him as we’d been talking about it more and more but it always just seemed like talk and we weren’t going to go thru with it as long as we enjoyed sucking each other off.
We got to his house around 10pm and I was in need of a shower if I wanted anything to happen. I went upstairs to the bathroom and on my way I ran into Jason’s dads boyfriend Marc. A very unsuspecting Marc. You see he was walking from the bathroom to the bedroom completely naked and his cock was sticking straight up. I am proud to say I have a 8” cock and Jason has a solid 7” but Marc, and maybe my surprise is exaggerating an inch or two to it but it looked like a 10+.
“You wanna touch it?” Marc asked with a smirk blocking my way to the bathroom.
I’m 99% sure he was joking since it was obvious I was frozen stunned.
“..no.” I replied as I cleared my throat a bit. Truthfully though I so wanted to hold it and yeah, suck it for a lil bit.
I had tasted Jason’s cum hundreds of times and came in my own mouth another hundred times but I really wanted to taste someone else’s cum.
Marc didn’t respond and turned and went into the bedroom. Marc wasn’t attractive to me but that cock sure was. Immediately after he went in the bedroom, I hurried into the bathroom and took off my clothes. My cock was so hard! As soon as I got in the shower I started stroking my dick. I came almost instantly.
When I got out of the shower and dried off there was a piece of paper by the sink.
“Come get your surprise” it said and there was a kiss mark with dark red lipstick. My heart started pounding in anticipation. Did Jason find a girl to suck our cocks? What was going to happen next? So many scenarios went rushing thru my mind.
I exited the bathroom wearing nothing but my boxer shorts. As I walked down the hall I noticed that the door to Jason’s dads bedroom wasn’t closed all the way. My curiosity got the best of me and I crept toward the door. I put my eye to the crack but couldn’t see anything. There was definitely some kind of movement going on in there, I could hear it but I couldn’t make out what I was hearing with one eye placed against the cracked door. I decided to take a chance and push the door open just enough that I could see with one eye. I came up with an excuse in the event they caught me. I’d just say I thought I heard one of them say my name. Not a particularly believable one but one nonetheless.
I held the doorknob so it didn’t open too much and slightly pushed it open a half inch or so. I could now see what was going on much better. Marc had his back to me and had Jason’s dad bent over the bed frame. He was thrusting pretty hard and Dave (Jason’s dad) was moaning pretty good. I had never been more turned on in my life. I couldn’t see anything because they near their backs to me but I knew enough. I knew Marc had a huge cock, and I knew it was inside Dave’s ass good and deep. If Dave could take Marc’s big ole hunk of meat then maybe Jason and I could figure out how to do this. Couple what I was seeing thru the cracked door and what scenarios were racing thru my mind and suddenly I was open to trying anal sex myself.
I slowly backed away from the door and crept towards the basement door. As I closed it behind me my heart started racing even more now. Each step down made my heart pound more and more and sweat was building up on my forehead, and hands. As I opened the door to Jason’s room he was standing there next to the bed. He had a long blonde wig on, a black lace bra and matching black lace panties. He had tucked his cock and balls between his legs, and he had done up his make up quite well with that dark red lipstick that was on that note. My jaw literally dropped. I was speechless.
“I really wanted to have sex with you and I thought maybe this would help with encouragement.” He said to me.
I hesitated for a second or two being completely caught off guard for the second time in 15 minutes.
“.. uh, yeah. Yeah.. wow! You look sexy! Wow!” I uncomfortably uttered still frozen in the doorway.
Jason signaled for me to come closer. I approached him slowly and he reached out his hand and took mine. As he pulled me closer I could smell he had put on some girly lotion that not only made his skin soft but smelled intoxicating as well. I had never been with a girl before that but that’s what I had imagined it would be like. Later I found out I had confessed much of that to him earlier which is why he hit it out of the park that night.
He pulled me in and we started kissing. Our tongues wrapped around each other in by far our most passionate kissing we had ever done. I ran my hands up and down his soft body as we continued to kiss.
He sat on the corner of the bed and pulled my boxer shorts down to my ankles. So that he wouldn’t crush his cock and balls he moved them back to the front and his dick was sticking up out of the black panties he was wearing. As I kicked off my boxers I felt his hand grab ahold of my shaft and his warm mouth wrap around the tip of my cock. At this point I was even more happy to have had that short interaction with Marc because if I hadn’t, I wouldn’t have jacked off in the shower and I would’ve cum in Jason’s mouth instantly.
A few minutes of him slurping my cock go by and now the excitement begins to grow. I push him back on the bed and immediately put his cock in my mouth. It’s warm, rock hard and there’s a substantial amount of pre cum already trickling out. My tongue dances around his tip licking up as much of it as I can. I push it back into my mouth and I feel his hand on the back of my head. That was always our way, in the beginning before we let each other cum in each other’s mouths, of telling the other we were about to cum. Now we had both become in love with each other’s cocks and cum that it just made our intensity rev up.
When his hand hit the back of my head I started cupping his balls and squeezing his shaft. He began to moan a bit and pull my hair. I released my tight grip on his shaft and an explosion of hot sticky cum shot down my throat. I began stroking his cock vigorously in an effort to get every drop out. He reached down and grabbed it from me and I let him squirt the last few drops down his shaft. He took a deep breath and let go of his cock and I took the opportunity to lick up every drop left behind.
As I pulled my head up Jason handed my a small bottle. It was lubricant.
“Fuck me.” He whispered as he sat up. “Make me a woman” he added.
He got on all fours and I pulled the panties down around his knees.
“How much of this stuff do I need?” I asked
“Put a small squirt on my hole and then some more all over your dick” he replied
I squirted a small bit on his hole and then a glob on my cock. Jason reaches around and started fingering his hole making sure the lube was everywhere it needed to be.
“Slowly push your head inside me and do exactly as I say” he instructed
I grabbed his hip with one hand and my cock tip with the other and pressed it against his hole. I started to push slowly like he told me and shortly after my entire tip slipped inside him.
“Oh shit!” He moaned.
“Pull it out?!” I asked
“No! Leave it in! Go deeper but go slow for now.” He said
I started to push a little deeper. I slowly watched my dick disappear inside his ass. I got it about half way in and then pulled back a bit. He let out a cry. Then I pushed it in a little further this time. Each time I pulled back he moaned a bit.
“You ok?” I asked
“Your dick feels amazing!” He replied
He was loosened up now and my I began to thrust a little harder and a little deeper. He sat up so my chest was pressed against his back. I reached around and found his dick was rock hard again. I began stroking him.
“I’m gonna cum again!” He moaned “keep going!” He added
“Me too!” I moaned back
I felt a small trickle of cum hit my fingers and he cried out and pushed his ass back against me. My cock slid as deep as it had gone inside him and I released a batch of hot cum inside him.
I licked the few drops of cum off my fingers as he sat up. My cock slipped out of his ass. Still on his hands and knees I see his pulsing gaping asshole and my hot cum drip out and down his leg. His hand reached between his legs and swiped up a bit of cum and put his finger in his mouth. He crashed on to his side and I laid next to him. Both of us a hot sweaty mess. We kissed a few times and then rolled onto our backs to catch our breath.
“How was it?” I asked him after a few minutes of silence.
“We have to do that again! That’s my new favorite thing!” He replied with a laugh
“Really?” I asked
“How did you like it?” He asked in return
“That’s my new favorite thing.” I said laughing “Do you want to fuck me?” I asked after the laughter calmed
“Not if you don’t want to. I’m fine with this arrangement but if you wanna try it sometime we can. No pressure though.”
I have been with my share of girls in my life including my wife but all thru it Jason and I have continued to have a sexual relationship. Both our wives understand that this is something we both need and want. He’s the only man I’ve ever had sex with. About a year after this I found myself in an interesting situation at his house with Marc. I explained to him Jason and my relationship one night and I reminded him it started that night I saw him naked and rock hard. I literally told him every detail of that night and long story short, I gave him a blowjob later that night when Jason and his dad were sleeping. It wasn’t as good as Jason but it was something I wanted to do and wasn’t going to stop until I did it. His cock was as big as I thought and his cum wasn’t as good as Jason’s or mine for that matter.
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