Losing My Virginity

Growing up I never imagined losing my virginity to a boy.

I have posted stories on here before under a different name and all of them were completely false. Some of them were kind of inspired by things that happened to me or stories that I had heard or read. This story is real. It’s the story of how I lost my virginity.

When I was 9 I met a new friend, Jayson. We became good friends very quickly, riding bikes, playing baseball and such. One night after we had been friends about a year, we were having a sleepover. We had many sleepovers before without any incident but for some reason things took a turn in our friendship that night.

It was a hot summer night, and we were getting ready for bed. We had just spent 4 hours playing video games and eating pizza and were both pretty tired. We both decided to sleep in our boxers. We laid quietly in his big queen size bed trying to fall asleep when I felt a soft tickle down my back. I said nothing as the goosebumps gave me a nice chill on that hot night.

A few seconds later I felt his foot softly rub my leg. I turned and asked him what he was doing. He told me he was horny. I admitted that I kind of was as well. He pulled out a Playboy that he had under his mattress and we ended up jacking off together.

This kind of thing went on for a few years until one night when we were 14, we both worked up the courage to give each other blow jobs. We had talked about it for a year but had always chickened out. For whatever reason that night we went thru with it.

Both of us were god awful at sucking dick as it was our first time, but because it was the first time either of us had ever had anything other than a hand job from each other, we both came hard.

Over the next few months we would regularly suck each other off, getting better and better at it each time.

One night when we were 16, Jayson had moved about 30 minutes away and to a new school. I went over to his house on a Friday night after my football game. I was always so excited to hang out with him now that he was further away and we didn’t hang out as much. I think that him moving away and us not hanging out everyday had a lot to do with how our relationship changed.

I got to his place around 11pm that Friday night and when he opened the door, I entered and he kissed me. We had made out with tongues many many times but always in the privacy of our bedrooms. This time I had barely closed the front door behind me before he had his arms around my waist and his tongue in my mouth. I assumed it was because his parents were already in bed and he felt more comfortable, but he never greeted me with a kiss before so I was a bit taken back.

We immediately went to his bedroom which was in the basement of his house. That was where we usually did stuff because we had more privacy than my bedroom. We sat on his bed and started kissing some more and it didn’t take long before we had removed our shirts and then our pants and underwear.

Our tongues swirled around each other and our hands wrapped tightly around each other’s cocks. Jayson laid down on his bed and I climbed on top of him in a sort of missionary position. We continued to make out and grind against each other. Our dicks rubbed against each other and I almost came all over his stomach right then and there. We had done things like this before but this time seemed a little more intense. We both seemed to want each other.

I knew if I kept grinding on him, I, or both of us would cum all over the place, so I sat up and positioned myself between his legs. I grabbed ahold of the base of his shaft and wrapped my lips and tongue around his tip and began sucking his cock. I have always considered myself straight, even while his cock was in my mouth I thought I was straight, but just having a little fun.

For the first few months that we would exchange blow jobs, we never came in each other’s mouths. We were both too scared or nervous or grossed out. We always tapped the other on the head to let them know they were about to cum and then we’d finish the job with our hand. It wasn’t until one time Jayson decided not to tap me so he could feel what it was like to cam in my mouth. He held my head in place as he came. I fucking loved it! When I convinced him to try it as well, we never didn’t cum in each other’s mouths. We had both grown to love the taste of each other’s cum. Even then I still thought I was straight.

As I continued to suck his cock, I could hear his breathing change and his shaft swell a bit in my mouth. I began using my hand a little more and then an explosion of cum like never before hit the roof of my mouth and kept spitting on my tongue and down my throat. I always swallowed every drop he made willingly but this time I had no choice. It felt like my mouth was completely full of cum. I kept sucking until he finally stopped cumming and I had swallowed every drop. I looked up at him and laughed a bit.

“Holy shit that was a lot of cum!” I said to him

“I haven’t jacked off since the last time you were here a month ago.” He said laughing a bit as well

“Wow!” I added

I slowly climbed up his body and started kissing him, then I laid next to him thinking it was my turn to get my cock sucked. Jayson reached into his drawer next to his bed and pulled out some stuff. He handed me a bottle of KY lube.

“What’s this?” I naively asked

“I’m ready!” He said while then handing me a condom as well.

My jaw dropped, like literally dropped! We had talked about this for a while but unlike the blowjobs, I didn’t think it would ever happen. I knew I wasn’t going to let him fuck my ass. I knew he was serious about being ready though because one night we did try it and he chickened out, if you wanna call it that, as soon as I started to enter him. He said it hurt too much. That was probably 4 or 5 months earlier.

“How do you wanna do it?” I asked not even questioning his willingness.

“Whatever way you wanna do it.” He answered

“I suppose just doggy style then.” I said

Jayson didn’t hesitate. He got up on his hands and knees and told me to squirt a bit of lube in his hand. He rubbed it all over his asshole and I did the same with my cock.

“Ready?” I asked

“Mmhmm. Just go slow.” He moaned

I pressed the tip of my dick against his butthole and started to push. He let out a gasp, he was nervously holding his breath. The room was dimly lit and I couldn’t see much but I did see the tip of my cock slowly disappearing. Jayson reached back and put his hand on my stomach almost if you keep me from going further in. Just then I felt a slip, and heard Jayson moan out.

“Oh shit that hurts!” He moaned

The head of my cock had slipped all the way in his tight asshole.

“Do you want me to take it out?!” I asked scared I was hurting him.

“No no no no, leave it in, just go really slow.” He moaned and panted.

I sat there with just the tip of my dick inside him for a minute or so and then as his breathing slowed I started softly thrusting. There wasn’t much movement on the first few thrusts but when I went a little harder I felt my dick go in a little deeper. His ass had relaxed a bit now and I could slide in and out. I pushed it in as far as I could, balls deep and he yelled.

“Oh fuck that’s deep. This feels fucking amazing!” He yelled

My thrusting was now much more normal and I was now fucking him! My hands held his hips tightly, and my eyes were fixated on my cock sliding in and out of his hole. All I could think about was “Oh my God, I’m losing my virginity!”

It wasn’t long before I felt like I was gonna cum. I started thrusting as hard as I could. He yelled at me to slow down, then stop! But I was to close and before he could tell me to stop again, I made one last deep thrust and came! My hands squeezed his hips and pulled him as close to me as I could. My toes curled and I was lightheaded for a second or two.

As I pulled my cock out of his ass, the quick stench of shit hit my nose and was gone as soon as it came. I didn’t mind one bit! We both collapsed in the bed next to each other, both struggling to catch our breath.

“Holy goddamn shit, that was amazing!” I said “..are you ok?” I then asked

“It hurt like hell at first but then got easier. Sucked at the end. Maybe next time go a little slower.. at least until I’m used to this.” He explained

“Next time? Awesome!” I said laughing while still trying to catch my breath

I sat up and removed the condom. It was full of cum. Not as much as he made a few minutes earlier but still a substantial amount considering I jacked off earlier that day in an attempt to make the blow job I thought I was going to get last longer.

That is how I lost my virginity to my friend. We had sex many times after the first, every time was me inside him. I never let him fuck me. He never pressed the issue, especially as long I continued to blow him, which I did. Our sexual relationship went off and on until we were in our mid 20’s. It survived girlfriend’s that never knew and his wife, that never knew. I haven’t been with any other man in my life but him.

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