Rye’s Encounters Pt. 04

A gay story: Rye’s Encounters Pt. 04

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.

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.

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Following my anal deflowering, that same top, featured in Pt. 3, wanted a lot more. He wanted to teach me where my place was a a sissy bottom and to open my eyes to how deep the sissy rabbit hole can go…

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CH.1

“Follow Up”

A few days pass since the top claimed my sissy holes. I check my email out of curiosity and since my sexual energy had recharged since that evening. 2 new emails. All from the top.

“Hey boy, that was a hot little time. Lets do it again soon. Send me some more pictures of your ass, I need to have something to JO to.”

“BTW Im Alex. Heres my cell, text me (555) 555 – 1234”

I immediately texted pictures that I’ve been using in other communications with tops who wanted to see more. One pic is of my ass with my finger under my cheeks, propping up my ass. The other pic captures my fit figure contrasted with my fat bubbly ass and muscular thighs. I like it when they ask for pictures, it makes me feel sexy.

In the body of the text message, I wrote:

“I’m sure these pics will remind you of who this is. BTW Im Rye”

He texted back withnin 5 minutes with:

“Damn. What are you doing Friday night”

I replied, with empowered sexual confidence, “You, hopefully. Same address?”

“No, I was just house-sitting. Im doing it again at another spot in the same neighborhood.

1254 Redwood Ln. 10pm”

And there it was, my next contribution to the sissy cause. Another date to serve cock.

He double texted me moments after receiving the address and time:

“Be ready to stay a while and serve like a good boy”

Reading that made me instantly hard and mentally submissive. I reply, simply:

“Yes sir”

My heart beating fast, butterflies in my tummy, my clitty trying to burst the seam of my pants–I was so ready.

Another countdown begins, 5 days, 10 hours…starting now.

——-

CH.2

“Redwood Ln”

Friday, 9:45PM. I parked my car back on Collier and walked over to Redwood. I started to feel antsy and didn’t want to have anyone see me entering / exiting / driving away so easily, plus I was already familiar with Collier from last time.

Before turning the corner while walking down a few blocks to Redwood, I turn back to gaze at the house where I completed my first anal task as a self-proclaimed sissy. Some lights were on in the house; I wondered if they could sense the rite that was performed in that living room just a few days ago.

A short walk later, I was again face to face with another portal to my dark future: A door, with some numbers next to it; a doorbell, with a little circle for a button; a welcome mat, graciously inviting me to participate in my fate.

“Ding-Dong” the doorbell rang in muffled tones.

10PM struck, and, right on time, the door opened to Alex on the other side.

“Hey,” he said with a little smile on his dimly lit face.

“Hi,” I coyly replied, visibly blushing in the porch light.

He lets me in and guides me to another living room, with a large couch placed in front of a large TV, which displayed a still image of a large cock jammed into a transgirls ass. The video was quickly resumed as Alex caught me staring at the screen.

He told me to chill and that he was going to smoke some weed really quick. I nodded and sat down on the couch to watch the porn. The fact that I came here to do exactly what that actress was doing on screen was not lost on me: I am here to serve and take cock like a good sissy.

I quickly take off my pants and set them aside to reveal tight fitting red boxer briefs. I want to feel accessible to my top.

The lights dim and Alex walks up next to me, the smell of weed fragrancing the air, with his cock and balls hanging above the wastline of his basketball shorts. I touch his cock and stare with wide eyes for a moment. He then sits down very close next to me and place his right arm around my shoulders with his hand wrapping at the side and front of my neck, like he was preparing to gently choke me.

I lean over and he gently pulls my head and neck towards his dry semi hard cock. It’s exactly as I remember. Without preamble, I put his entire cock in my mouth and begin to suckle on it. His cock quickly grew inside my mouth as I slowly altered between sucking and tongue flickering. As his cock stiffened, Alex slid his right hand into my boxers to caress and squeeze my ass cheek.

His precum flow increased and he inched closer and closer to my little pucker. I gratefully swallow and taste the precum as it glides along my tongue. I begin to mouth-stroke up and down on his cock faster and he lets out a low moan. I cup his balls with my right hand and slowly rub in the saliva and precum mixture that since slid down from his now wet and hard cock.

He sneaked his hand beneath my undies and grabs a handful of my ass cheek. Alex then tells me to take off my boxers. I take them off while he still grips my bare ass. He leans over to gaze at my hole as he speads my ass cheek. My hole was hungry for cock, so I flexed/winked it at him. He responded by lightly tickling my little picker with his middle finger. The sensation was electrifying and incredibly eroctic. I responded by diving deeper and faster onto his cock.

This went on for a few minutes, him gently tickling my sissy hole while I energetically plunge my face into his pelvis. Occasionally he would reach a little further and gently stroke my taint and get very close to touching my little sissy balls. We were both in silent ecstacy, minus the tones of slurping and the porn playing on the tv. It was that day that I learned about my interest in soft light touching and feather play.

After coming up for air for the hundreth time, he told me to wait there on the couch. He got up to go get something out of a bag on a near by table. Before he sat back down, I noticed that there was a damp spot on the couch where his cock and my mouth met. I was really giving him some sloppy head.

He sat back down and put a bottle of lube, 2 condoms, and a small brown bottle on the coffee table in front of us. I asked him what the bottle was. He smiled with a devlish grin and replied, “Those are called poppers. You sniff them and it makes you super horny”.

“What does it feel like?” I inquired.

“It kind of feels like Coke, but without the side effects,” he replied.

I didn’t really need any drugs to feel empowered enough to be a sissy, so I kind of just shrugged it off. It was obvious that I had never tried them based on my questions and demeanor. He grabbed the bottle, uncapped it, and took a long sniff. He quickly capped the bottle after he was done sniffing.

“Your turn.” he said with serious look on his face.

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