My First Anal Part 4

My boyfriend Jason and I were in a fully sexual relationship and we began trying to find new ways to enjoy each other.

Jason and I continued to have a great sexual relationship with each other. I was used to and completely comfortable with anal sex by now. We were basically spending every minute of free time with each other and every minute was doing something sexual. Sitting through an entire day of school without getting rock hard in class was absolutely impossible. I’d find myself daydreaming during class about what we’d do as soon as school was out. Most days we’d just race to his house and immediately begin sucking each other’s cocks.

We had been giving each other oral sex for almost 3 years now and had finally taken that last step of anal sex about 6 months ago. In our entire relationship, we never talked about who was a top or who was a bottom or anything remotely close to that. Both of us are bisexual and married nowadays. Our roles in the relationship just sort of happened organically. I found myself, probably because I had been secretly dressing in women’s clothing for a few years, and being overweight I have man boobs, being the submissive bottom, or the woman, or the feminine one, whichever you choose to call it. And Jason, probably because of his 6’4” athletic body just fell into the top or the dominant one. It worked out perfectly.

Now that we were having regular sex, we were always looking for new, interesting, or different ways to do it. Jason loved the idea of having sex in a public place. We tried that a few times. Once in a park at night, another in his car, and a third in a Target bathroom. I wasn’t a huge fan of it and was thankful we never got caught.

One idea that had been swirling around in my head for a while was having a second guy. A threesome! I was very hesitant to approach Jason with such an idea because he was rather popular at school and we had some pretty big secrets that would’ve buried us if they had gotten out and bringing in a 3rd person, most likely someone who went to school with us was risky.

The more I ignored the idea, the more it swirled in my head and the more I wanted to do it. I finally suggested it to Jason and he was a little unsure about it at first. Whether we wanted to admit it or not, we were in a gay relationship and we had even gone as far as telling each other we loved the other. Introducing a 3rd person could certainly make things a little awkward between us.

I let it go for a few weeks until I had heard rumors of another guy I at school being gay. I had no way to confirm it and I was definitely not going to ask him, but it sparked something in my mind. I found myself fantasizing about him when I’d see him in the hallway or at lunch. His name was John. He was quiet and shy but had a nice physique as well. Not that of a top football player that Jason had but still pretty good. My fantasizing went so far that I began thinking about him while Jason and I were 69ing one day.

I approached John at lunch one day while he was sitting alone and started up a conversation with him. We got along pretty well. I spent about a month building up trust with him before I finally asked him the big question..

“Are you gay? I heard somewhere that you were.” I boldly asked

“What?! No! That’s crazy!” John replied storming off.

I could tell that he was lying by the way he responded. I approached Jason with the idea that we befriend him and maybe if we can confirm he’s gay, maybe, just maybe we could try a threesome.

Long story short, we have John a couple days to cool off and became friends with him. He was indeed gay as he came admitted to us and we told him about us.

I knew that I wanted to have a threesome with Jason and John but I hadn’t asked John and Jason was still not crazy about the idea. I had to convince him first.

I told Jason that I had been doing things in public places with him and wasn’t crazy about that so maybe he could meet me halfway on this one. Reluctantly, he agreed, and we decided to talk to John together.

We invited John over to Jason’s house on a Saturday night and started chatting. When the conversation slowed I just got impatient and blurted it out.

“I’m a cross dresser and Jason and I want to have a threesome with you.” I boldly admitted

John was taken back by my honesty and had a bunch of questions, all of which we answered honestly. John admitted that when we told him we were in a relationship, he began thinking about us as well. We all kind of chuckled a bit and the mood instantly changed from uncomfortable chit chat to how do we get all this started?

It was my fantasy so I had my own ideas and I had some clothes for the occasion. I couldn’t change in the bathroom for fear Jason’s parents saw me so I climbed into his bedroom closet with a flashlight. I know right…

Over the past few months Jason had bought me a few pieces of lingerie and stuff so I just kept them at his house.

First I put on this white silk thong. I added a matching pair of white stockings that had little bows on the back of the thigh. Then I put on a white silk babydoll dress. It was far too dark for me to put on any makeup, not that it mattered, my skills weren’t getting any better anyways. I did however have a sexy blonde wig that I capped it off with.

“Are you boys naked and ready for me?” I said in my most seductive tone

“Mmhmm” they both replied

I swung the closet door open and saw both of them lying on the bed naked. They couldn’t take their eyes off me, especially John. He sat up a bit to get a better view as I approached the bottom of the bed. I was equally impressed when I saw John’s cock standing straight up. It was massive! Jason’s was 7” and John had to be between 9-10”.

“Look at this.” I said to Jason pointing out John’s huge dong

I climbed between John’s leg and took his shaft in my hand. It was so hard but also incredibly soft. It smelled amazing! Jason sat up and leaned over and we both began licking and sucking on John’s cock and balls. We were enamored with the size of his member and almost ignored each other.

“I wanna fuck you so bad right now!” Jason whispered to me

As he sat up to grab the lubricant, I began sucking John more thoroughly and aggressively. Jason had positioned himself behind me already and pulled my panties down around my knees. I felt the tip of his cock press against my ass and he pushed it in! I moaned as loud as I could with John’s cock in my mouth. As soon Jason was inside me, I felt John put his hand on my head and I blast of hot cum hit the roof of my mouth and slid down my throat. Before I could get a chance to prepare myself, a second blast just as strong landed on my tongue. I found it difficult to focus on the taste because Jason was going to town on my asshole. His hands were squeezing my hips so tightly that I thought he was going to break the skin.

John finished cumming and I swallowed every drop of it! He continued to lay there and I played and sucked his semi hard cock while Jason continued to fuck me.

“Oh I’m gonna cum so hard!” Jason moaned

I immediately put John’s cock back in my mouth and started sucking him again. He began to get hard again! Just then, Jason’s grip got even tighter, and he bit his bottom lip so not to scream too loud. I felt his cock pulsing as it pumped shot after shot of cum in my ass! John’s cock was rock hard again and as nervous as I was about the size and width of his dick, I wanted him inside me.

As Jason pulled out I instantly felt cum dripping out of my ass. Jason sat back on his heels to catch his breath and he smacked my ass.

“Holy shit that was awesome!” He said sounding exhausted

“You gonna fuck me with this big ole dick now?” I asked John

“I’ve never done this before.” He said as he nervously sat up.

John positioned himself behind me and Jason squirted a small bit of lube on his cock. Jason then grabbed John’s dick and pointed it at my eager hole. John thrusted forward a bit and the tip of his big dick went in my ass. Then he pushed it in almost all the way!

“Oh fuck that’s deep! Oh god that’s big!” I cried into Jason’s pillow even biting it a bit to avoid screaming.

John was far more gentle with the hip squeezing. He continued to slide his cock in and out of my ass. I couldn’t believe how thick he was! It was definitely stretching out my hole! John fucked my ass for over 20 minutes in a few different positions! I couldn’t believe how long he was lasting. It had to be because I emptied the chamber in my mouth just before.

“I’m ready! I’m gonna cum!” John shouted, perhaps a bit too loud but no one noticed

I thought it was amazing when I would feel Jason’s cock pulse and swell when he came but feeling John’s cock get just a bit harder and thicker as it pumped spurts of cum in my ass was incredible! When he finally pulled out, I was ready to be done, but Jason quickly got on top of me in a missionary position and slid his cock back inside me. To my surprise, he came pretty quickly. When he pulled out, he fell next to me on the bed. John laid on the other side of me and all three of us were drenched in sweat. John stayed the night with us and we didn’t have any more sex that night on account my ass hurt but I did give both of them blowjobs in the morning.

John left shortly after and Jason was nice enough to give me an incredible blowjob as well. When it was over he crawled back up and laid next to me.

“That was pretty fun… I love you.” He said

“I love you too… and yeah it was.” I answered resting my head on his chest.

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