Rye's Encounters Pt. 01

Note to reader:

The following series of encounters are 100% non-fiction, best of my ability accounts of my real life encounters with horny men. Names, locations, and revealing details were altered to protect identities of course.

PREFACE:

Hi. My name is Rye. I am a cute, 5'9", blonde, big booty, white boy...with a hunger. I have a fairly symmetrical face, big wide eyes, and a fit figure. Also, I have been told I have a nice smile with fairly straight teeth.

This is the story not another soul knows.

-------

My sexual saga begins in the summer of 2015. I was freshly 21 years old and working with my father for the summer break...

-------

CH.1

"Fuck. Everything."

I had just had the back to back worst semesters of my life. I had just transferred to a school up north from LA and I could not go one semester without fucking things up. I felt like a failure...because I was a failure--I completely dropped out due to grades. Everything sucked.

My father owned a flooring company and had me working with him 9-5 to make money and to get me motivated again. That sucked too.

Everyday pulling flooring. Everyday bending over to pick up trash and cleaning on the job site. Everyday receiving constant ridicule from my father or his burly workers. I hated being the official Construction Bitch.

When I came home, all I wanted to do was jack off and play video games--which I definitely did.

My depression at the time was such that it became harder and harder to get off. I tried different types of lubes, to no avail. I needed release.

So, I tried different porn sites. The classic sites were great, but I was a part of some algorithm and couldn't get off with what was available. I tried a forum-type website where people posted their own, organically sourced videos. The best of the best. Even that was rough. Though, the categories ranged from creampies to beheadings, so it was easy to float around to crazy to funny to sexy to interesting to revolting. I stuck around for a while.

After hours of daily drudgery, I would come home and find a new category to explore. One day I found a gay/sissy category. At first I didn't really get it. Was it like cross-dressing boys or girls or what? I tried it and it was kinda hot. Felt bad after I came, but whatever.

Next day, I found myself back in sissy land. Reading people's stories and comments and videos telling me to suck cock and submit myself. Go on Craigslist. Find a daddy. Do what he says. Hot.

I had always known about Craigslist and figured it was sketchy...so no thanks.

Day after day, I came back and searched for more. It was such an immersive experience. 3 videos in and I am a sissy slut. Then I cum and I'm Rye again. It was a nice break and I came hard to the thought of a sloppy dick in my mouth...slowly conditioning myself for my secret life ahead of me.

Say a month later of shitty days and cummy nights, I decide to try this Craigslist thing out and see what's happening. Click around to find personals and notice that it gives me a choice...men for men or men for women? Guess what I picked.

The people posting were gross. No genuine requests, just pigs trying to fuck pigs. I wasn't a huge fan, so I decided to post the sole genuine response and see what happens.

"Virgin white boi looking to suck a dick"

I was not a virgin in any single way at this point in my life.

The post got over 50 hits and was blowing my email up. I replied to a few, but I was nervous that someone might know me since I grew up in the area. I only reply to emails with face a dick pics.

I found one guy, we can call him Sam. Caramel skin, muscular, jock type black dude. A dude you would never think was into white bois in passing. We chatted and exchanged numbers.

In text he asked for my face pic. I was super nervous and didn't want to, but he said "don't worry, Im cool". Apparently this was enough for me. After sending the selfie picture, he replied "you look cool". To which I replied "cool".

I gave him the 20 question routine and he had no problem answering everything. From STDs to sexual experiences to where he grew up. He wasn't from my town and that was great news for us both. We scheduled a date to meet that week.

The hours and days following were a flood of emotions I haven't felt for years--excitement, danger, enthusiasm, lust, and most of all fear. I couldn't believe I was going to do this or even got this far. I had almost canceled 20 times...but I didn't.

They day finally came. Hours crept by. Every bit of sweeping or trash pick up felt like an eternity of desert sand in an hour glass. It got me so insane, I even asked to leave early to prepare.

I drove to the meeting spot and cleaned out my two door car. We were meeting at a clean public park. As I waited and texted him with updates, my hands shivered and ankles shook with adrenaline.

I see a black BMW pull up next to me with a subsequent text of "hey cutie".

"I'm straight and had sex with women before...why do I feel butterflies?" I thought as I was meeting a guy to suck his dick.

We decided to go with my car since he thought that it would get "messy". I wasn't sure what he meant.

We drove around to find a more private location and found one about a mile away. All the while, making awkward nervous small talk. My non driving leg, shaking and bouncing like a kid waiting for a roller coaster.

Awkwardly, we climb into the back of my 2 doors back seat. He takes the passenger back seat and I take the driver side back seat. I realized that I had not really looked at this guy yet, even after driving around for a solid 10 minutes.

He had green eyes, plump lips, caramel complexion, and large but not super defined muscles. Sam smiled and asked how I wanted to start...I responded with gently starting to undo his pants. This task proved more difficult than I previously imagined. He helped take off his jeans to express red, loose fitting boxers. I remember him saying over text that he was 8 inches.

I slowly put my hand on his crotch to find a warm, semi hard log under this little piece of cloth. I pulled down his boxers to reveal a girth-y dong with trimmed black pubes. His cock was much darker than his caramel skin...like it could have been attached to a more chocolate colored man.

He asks me to take mine off too...which I complied, nervously.

I grabbed his standing rod and felt how soft and warm his dick felt and couldn't resist it any longer. I gently opened my mouth and tongue to take his head in my mouth and closed my sloppy lips around his frenulum. He let out a sigh of pleasure and grabbed my boxer covered ass firmly.

I took my time savoring his must and slurping on his gorgeous black dick. Up and down, then lick the sides, then cup the balls--all the things I like done to me. All the while, Sam his groping my ass and inching his fingers towards my little pink pucker.

Finally he touches my anus and gives his fingers a swirl around and on the pucker. This drove me wild as I attempted to deep throat him with every bob and stroke.

By this time, my mouth is slobber wet and drool-y thick saliva is abundant. He tells me to spit on his hand. I do. He then takes the spit on his fingers and pushes two in my asshole. His fingers were colder than his cock, but he was gentle. Every time I went down, he pushed in.

This went on until he had 4 good fingers in my ass to the 2nd knuckle, slowly gaping my cheeks and applying more of my endless lube. Me: bobbing and slurping relentlessly on his rod.

"I want you to cum in my mouth" I said.

"In your mouth?" Sam repeated.

I gave him a confirmation hum since I had already started back on with my mouth.

He then pulled his fingers out of my properly lubed ass and started to buck under my mouth. His right hand, now resting on top of my head, started pushing increasingly more hard. Sam's left, grabbing my plump nipples and massaging the parts of me he could reach.

This continued to get increasingly more tense and aggressive until Sam was literally hitting the back of my throat, pushing my head straight down to his balls, and thrusting violently upward. All I could do was just try to breath when I could.

In my head, I saw flashes of the hypno pornos I had binged on. Suck his dick. Please him. This is what you were made for. Sissy slut.

If Sam were to have stroked my dick one single time, I would have came out of principle.

It wasn't until the very last moments that it clicked in my brain "why was he playing with my ass so much?"...he wanted to fuck my ass like he was fucking my face. I was so slobbery, it would have been easy to stay lubed. He had pulled my hole apart so thoroughly, he would have slid in like the missing puzzle piece to my soul. That's why he said it was going to get messy. In that moment I wanted nothing more than his warm sloppy rod slipping around my guts...gifting me his warm gooey lust, just inside my hole.

But alas, he plunged me as deep as he could and violently blew his load in the very back of my oral cavity. I couldn't even taste the cum, like I wanted to. He held me there, only allowing me to suckle and slowly bob the rest of the length of his dick.

I slowly cleaned him up with my mouth. Giving Sam my last bits of oral energy and tenderness. Rubbed his dark balls sweetly. Finally removing his spent cock from my aching jaw.

We quietly moved to the front and unceremoniously drove off.

We said bye. That was it. My moment of immersive sissy indulgence...

...and I wanted more.