My First Gay Experience Part III

Jason and I had begun a sexual relationship but now a wrench was about to be thrown into it.

I just woke up, rubbed my eyes and looked at the clock. It was just after 6am. The sun was just about all the way above the horizon now and I could see Jason was still asleep. We just had sex for the first time a few hours ago and we were both still completely naked. Normally we slept in our boxers together.

I quietly got out of bed and made my way upstairs to the bathroom. I didn’t bother to put on my boxers. I intended to go back to bed and spoon my naked body with Jason’s. Besides, the only other people in the house were Jason’s Dad and his boyfriend Marc, and if they were awake they weren’t going to see anything they hadn’t seen before.

I made it back from the bathroom without being seen. Both Dave (Jason’s dad) and Marc were still sound asleep. As I crawled into bed, Jason rolled over and smiled at me.

“Morning.” He said while yawning.

“Hey.” I replied climbing on top of him and greeting him with a kiss.

The kiss lead to more kisses and then tongues became involved. Before I could even remember I wanted to go back to sleep, we exchanged blow jobs.

I went home that day on cloud nine. I had lost my virginity, and I was sure it was a real relationship. Jason and I had real feelings for each other that had grown for years of childhood friendship.

Normally when we had a weekend sleepover we’d wait a couple weeks before we got together again but we both couldn’t wait to see each other again so we got together the following weekend at my house this time. The entire time my mom was asking us what big plans we had and what we’re we going to do. We did our best to pretend we had plans but all we wanted to do was go to my room, lock the door and take off our clothes.

My mom was an alcoholic and would drink pretty heavily on the weekends and she’d spend the entire time in her room. I knew that she wouldn’t bother us and wouldn’t be aware enough to know what we were doing anyways. As soon as she retired to her bedroom with her bottle, we ran to my room and started to make out. Once again we exchanged blow jobs. I never liked the idea of sucking another guys cock and I hated the idea of cum in my mouth but all of the sudden I found myself not being able to get enough of it.

Jason and I had an entire weekend of blowing each other with two times we had anal sex. It was still me entering him. I was still not sold on being the bottom, but Jason didn’t ask. Either he knew I was uncomfortable with it or he just enjoyed being fucked and sucked.

We did this for about a month and a half. Every weekend we switched each other’s houses and would spend most of the time naked and pleasuring each other.

After about 2 months of Jason and I being a couple or fuck buddies or whatever it was. Truth be told, we never did define it. We had sex, we said we loved each other and meant it, but never really put a label on it. By now school had started up again and we went to different high schools so we didn’t get to see each other as much during school year. About a month into the school year I noticed a girl being rather flirtatious with me. Sarah, was 2 years younger than me and an incoming freshman. She had big brown eyes, and big bright smile and liked skateboarding and the same music I liked.

Sarah eventually asked me out, well her friend Samantha asked me if I’d go out with Sarah and I instinctively said yes. We hit it off instantly and began spending all of our free time together. A month into our relationship I hadn’t even called Jason and when he called me, I always cut the call short because I was hanging out with Sarah.

Sarah and I started having sex and I was hooked on pussy. I forgot all about Jason and his cock. Sarah and I were each of our first partners from the opposite sex and so the sex was awkward and didn’t have an abundance of quality behind it but there was a ton of quantity. We went at it like rabbits. I got out a half hour before the freshman would and I’d run up to the drug store and buy a box of condoms, and we’d meet at my house after she got out and go at it. I was spending a huge percentage of my money on condoms but it was worth it.

This went on until Thanksgiving time. I had barely spoken to Jason since August and only hung out with him once. We did fool around but it felt odd and I wasn’t completely into it. I let him suck me off but when it came time to suck him, I half assed it and when he came, I didn’t let him cum in my mouth. I just jerked him off.

Sarah went away on vacation with her family for 2 weeks to visit her family and celebrate Thanksgiving and Christmas all in one. I called Jason to see if he wanted to hang out. I had told myself that I wasn’t going to cheat on Sarah but I knew that I wasn’t going to be able to resist.

I got over to Jason’s house just after dinner time and went straight to his bedroom. Jason jumped out of his bed when I entered his room and came over and kissed me. We wasted no time in making out pretty hard. I felt his hands unbuttoning my jeans and reaching in my pants. As they dropped to the floor I knew what we were going to do but I wasn’t sure if I wanted to do it.

“Wait!” I said as Jason was just about to drop to his knees in front of me. “I need to tell you something first.” I continued as I pulled him back to his feet.

I pulled my jeans up and walked over to the bed where we both sat down. I told him everything. I told him everything Sarah and I had done, how we felt about each other and that she was who I wanted to be with. He was shocked to say the least. I felt horrible. I did have intense feelings for him and it was clear that I was bisexual at this point but I wanted Sarah.

“Maybe what I want fluctuates. Today I want a girl, maybe tomorrow I want a boy.” I said. “Truth is, I want you both but I can’t ask either of you to do that. Plus she’s only 14, she’s not going to understand this. I don’t even get it.” I added

We sat in silence for a few minutes both trying to think of something to say. Neither of us had anything. I couldn’t take the silence anymore so I said I was going to go and he reluctantly agreed. I knew he wanted me to stay but I couldn’t.

The following weekend, after a number of calls trying to convince me to come over and “talk” I agreed. I knew it was a bad idea but Sarah was still out of town and I was getting lonely.

Jason and I watched a movie, played some video games and eventually went to bed. We both wore our boxers to bed this time and nothing else, which obviously wasn’t going to stop us if we wanted to do something but it was more of a symbolic wall.

Normally we’d both fall asleep quickly but we both had stuff on our minds and couldn’t sleep. About an hour into trying to sleep I felt Jason’s soft hand on my back.

“I can share you if she can.” He whispered before kissing my shoulder and rolling over.

I didn’t respond because now I had even more to process. This was unexpected for sure. It’s what I wanted but I didn’t think Sarah would go for it. I didn’t want to hurt her or do anything I would regret.

Jason fell asleep almost instantly after he rolled over. As if all his problems went away and now it was up to me. I laid there, staring at the ceiling thinking about Sarah, and then looking over at Jason. I couldn’t deny my feelings for him and I couldn’t ignore how great I felt sexually with him. With Sarah it was quantity and she was a girl. It’s not like the quality wasn’t getting better, we were just new to sex. It was getting better and I was doing a much better job at pleasuring her as well as getting myself off. With Jason, there were intense feelings. We loved each other. I wasn’t going to deny myself of him anymore.

“Hey!” I whispered in his ear while gently shaking his shoulder. “Are you awake?”

“I am now.” He responded while rolling over

I didn’t waste any time. I leaned in and began kissing him. Our tongues began to swirl around each other like two professional ballet dancers.

“I love you, and I’m not going to deny myself of your love. If you’re willing to share then that’s great! If she’s not, she has to go, not you.” I explained

“I’ve got a surprise for you, hoping this would happen.” Jason said as he climbed out of bed.

I casually removed my boxers as Jason walked over to his closet, grabbed some things and made his way towards the door. I heard him go upstairs and then a few minutes later I heard him walking back down the stairs. My heart raced wondering what he had planned.

The bedroom door swung open and Jason popped in and quickly shut it behind him and locked it. He flipped the light switch. My jaw dropped. He was dressed as a woman. He had a long blonde wig, some dark lipstick, a cute sundress on that he had gotten at the mall, a pair of purple stockings that matched the dress and some high heels.

“Whaddaya think?” Jason said posing for me

“You look amazing!” I said, truthfully. “You don’t have to dress up like this though. I love you the way you are.” I added

“Well, when you feel like a boy you can have me, and if she doesn’t want to share you, you can have this version of me when you want a girl. Tonight, call me Jasmine.” Jason explained

“Jasmine?”

“Yep, that’s my girl name, I just made it up.” He said

I scooted to the edge of the bed to meet him as he approached. I sat on the corner of the bed and wrapped my arms around his waist and ran my hands up his back. I felt a bra underneath the dress. His level of commitment was turning me on more than you could believe.

My hands eventually found their way up his dress to find a pair of lace panties which I wasted no time in pulling down around his knees. I saw his cock flop out and poke the inside of his dress. Unbelievably hot! He slid his panties down to his ankles and took them off, then picking them up with his high heel and transferring them to his hand.

“You’re just full of surprises!” I said with a chuckle.

Jason shoved his tongue in my mouth for just a quick kiss then shoved his panties in my mouth after. As I spit the panties out, Jason lifted the front of his sundress and draped it over my head. His cock was staring me right between the eyes. I slid my hand up his thigh and grabbed ahold of his shaft at the base and put his cock in my mouth. It tasted amazing! He smelled like peach body spray and tasted like it too!

I began to feel his cock swell in my mouth and his hand tapped me on the head. That was always our signal that we were about to cum so we weren’t taken by surprise but we didn’t use it anymore as we began to just say “I’m gonna cum!”

Just then I felt a small trickle of sweet saltiness and before I could enjoy the taste a hot spurt hit the roof of my mouth, and then another and another. If felt like he hadn’t had an orgasm in over a month. There was so much cum in my mouth it began to dribble down my chin. I tried to swallow as much as I could but small spurts kept coming out and every time I swallowed some, it felt like he shot a bit more.

“Holy shot that was a lot of cum!” I said laughing while wiping my chin of any leftover.

“Kinda been saving it for this.” Jason responded with an embarrassing smile

Jason lifted his sundress over his head revealing a cute lace bra that matched the panties he shoved in my mouth. I kissed his stomach a few times before standing and picking him up. He wrapped his legs around my waist and kissed me. I could feel his wet sticky cock pressed against my stomach. I laid him down on his back and grabbed the lube from his side table drawer. Jason quickly unhooked his bra and threw it on the floor. Before I could start to lube up my cock, he swiped the bottle from me and squirted a healthy dose in his hand. He stroked my cock 3 or 4 times getting it nice and slippery, then ran his hand against his ass wiping what was left on his hole.

I pressed my tip against his tight hole and pushed. We were getting better at this now and it was only a matter of seconds before the tip of my cock popped inside his ass. Our eyes locked the entire time as he bit his bottom lip and moaned as my cock entered him. He lifted his legs up which allowed me to go deeper. I pushed deeper inside him and he let out a gasp.

“Oh god your dick feels so good!” He moaned

“I’m so hard right now!” I answered with a grunt as I picked up the pace of my thrusts

I reached down and grabbed the wig and tore it off, throwing it on the floor. I was so close to cumming now. I desperately wanted this to last longer but it wasn’t going to happen. I had only been inside him for 2 minutes before I was edging.

“Oh my god, I’m gonna cum so hard!” I said, our eyes still locked in one another.

“Cum inside me!” He panted back as one hand placed on my lower back pulling me deeper inside him and the other hand on the back of my neck pulling me in for a kiss.

We began kissing passionately for a moment and then I exploded inside him. Jason bit my bottom lip this time as I moaned rather loudly forgetting we weren’t the only ones in the house.

I felt my cock pulsing unleashing my cum inside him. I lifted up to my knees and grabbed his ankles, and pulled my cock out of him. With it was a few drops of cum. Watching my cock slide out of his ass was as much a turn on to me as fucking his ass. If I could go again at that moment I would’ve.

Jason sat up and squeezed the shaft of my cock forcing out the last few drops of cum I had. He leaned in and licked them off the tip of my cock and laid back down. My sweaty body collapsed next to him completely spent physically and emotionally.

We didn’t clean up or shut the lights off, we just fell asleep naked, sweaty and satisfied…

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