Rye's Encounters Pt. 03

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.

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The beginning of my sissy transformation truly begins about one month following the events of Part 2. We circle back to Craigslist ads, searching for darker pleasures...

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CH.1

"Countdown"

Frustrated, horny, and desperate, I found myself frequently scrolling through Craigslist. I wanted to find someone to take control and show me what these Sissy videos are all about.

Often, men just wanted to fuck a slut, a pig, or a trans girl with no protection and no care. I was a little turned off by that. I wasn't interested in catching anything, so I avoided those people. They would hit me up with such aggression and horniness that it would never work for me,...at least then.

Eventually, a guy in his late 30s sent me a message saying that he liked what I had to say in my previous post and he wanted to meet up and be my daddy. He sent a picture of an average-bodied Latino male, a picture of his cock, and a STD test dated very recently. I liked what I saw and replied with my stats, and a nice booty pic, and opened the conversation. He was quick to reply, eager to fulfill my wishes to experience more than my last meetup, and could host. We made a date.

As the days went by, my appetite for sissy content increased by double at minimum. I was walking around my college listening to the sissy video's audio in my ears:

"Sissy sluuuut...take that big dick!...oh no, now you're a faggot," the videos reminded me. I've never been more anxious and horny at the same time. I tried to edge every night since I usually lose my drive when I cum. I walked around with perpetual blue balls. I kind of liked it.

At the end of every night approaching Day 3, I was sticking anything dick related inside my boipussy in an attempt to get my mind in a subservient place. It was starting to feel good to feel something stretch my hole a little bit. Like it felt like it was right. My little bubble ass was meant for this. My cock would be limp during insertion--as it should be.

Day 3 approached at a crawl, but I was ready.

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CH.2

"True Awakening"

Day 3 arrived. I checked my email for the 30th time that evening and received a simple message from my imminent top:

"334 Collitta Dr., 930P"

I replied, "Yes sir".

It was about 9 and I decided to get there early to scope out the area. I lept out of the house, turned on my car, and blasted sissy hypno videos the entire drive there.

In 15 minutes, I pulled up to the house. It was a nice neighborhood, which was unexpected. I turned down my sexually graphic encouragement and stared at the house. Little did I know then, that house was a portal that was going to shift my life towards a darker and hotter path than I would have imagined.

930P struck. I got out of my car and sped up to the door. I rang the doorbell. Butterflies fluttered in my tummy. My heartbeat increased significantly. My palms got a little sweaty. The door opened.

A man that fit the description in my email smiled and beckoned me in. He directed me to a couch in a large living room, where trans porn was playing at full blast. I sat on the far end and he sat in the middle of the couch. He was wearing red gym shorts that did not hide his bulge whatsoever.

He caught me staring at his cock, rubbed it, and asked if I wanted to touch it. I nodded and reached for the red lump. Gently stroking his bulge from tip to base, then base to tip, I felt his cock engorge with horniness. He flexed his cock and my fingers caressed his shorts again and again and again.

"Take it out," he commanded.

I complied by pulling his shorts down to his ankles. His cock greeted me as I came back up. It was a very average length, but the girth was almost double the size of my cock.

I remembered my sissy training, looked up at him and asked,

"Can I suck your cock?"

He smiled and nodded. Then, I adjusted myself on the couch doggy style with my ass up, arched back, and face down next to his anticipating cock.

The first thing I did to him was gently touch his shaven balls. I gently slid my fingers from the top to the sides, underneath, and all around his shaft. He deeply groaned and let out a long sigh of relief. His cock stood at attention, begging for a soft, warm hole. I obliged by licking his balls and slowly dragging my tongue to the tip of his glistening head. He slowly but audibly took a shuddering inhale.

I kept doing this maneuver with my tongue, relishing in the change in his reaction from my tongue massaging from his balls to the shaft, to the frenulum, and to his precum-covered glans. Slowly, I also kept feeling around the edges and underneath his ballsack. He was in a state of bliss. I was struggling to restrain myself.

After varying a few different routes up and down his cock, I decided to put his entire cock in my mouth without warning. He jerked a little and gasped as I went down to the base of his cock in one quick stroke. As I came up, I dragged my tongue up his shaft, slowly turning my head to achieve a subtle twisting effect on his cock. He grabbed a fistful of my hair and put enough weight on my head for me to know that his cock was staying in my mouth until he decided it was time to come out.

I noticed that cock doesn't taste like anything until you get a little bitter treat of precum. As I continued to bob on his thick rod, I realized that the taste of precum continued to increase. I didn't have a specific desire for precum, but I took it as a sign that I was doing a good job. To verify, I looked up at him mid-stroke and I saw his head was fully leaned back and he was gaping while breathing through his mouth.

"God you know how to suck a cock, don't you?" he said with his teeth suddenly clenched. I hummed my confirmation as a continued to suck him to the best of my ability.

"You want me to fuck your little hole, boy?" he asked while sliding his hand down the curve of my back, then back up towards my ass. I shook it from side to side and plunged his cock as far as it could go into my mouth in reply. He pushed his hips up and tickled my tonsils.

He slowly lifted me off him and stood up to grab a condom and some lube from the ottoman in front of us. I waited for him to put the condom on, then shyly started to undress.

I took off my pants to reveal a pair of light blue boxer briefs that were snug against my bubble butt and package. He stared at me, rubbing lube onto his covered cock. Then, I removed my shirt, revealing my puffy, girly nipples. He continued rubbing his cock.

Lastly, I turned around and bent over to show him my ass and slowly removed my boxers, inch by inch. He waited, watched, and stoked. Eventually, my boxers were around my knees and I naturally began to kneel on the couch we were just on, grabbing the back of the couch and sticking my bare, raw ass back at him.

I didn't immediately feel his hands on me, so I looked back at him. He stood in front of the TV, so all I could see was the porn playing, a dark silhouette of a man making masturbation movements, and my milky white ass, illuminated by the light of the TV. I shook my ass at him for the second time that evening, which he understood.

Suddenly there was a cool sensation on the pucker of my ass. It surprised me and caused me to gasp a little. Soon after, a very warm finger gently pushed open my anus and allowed the lube inside me. The finger pushed in and out of me 20 or 30 times. It felt easy and kind of soothing since he wasn't particularly trying to stretch me out or finger my hole super fast.

"Are you ready, boy?" he inquired while continuing to plunge my pussy.

"Yes..."

He slowly withdrew his finger. I felt his hands on the sides of my hips and his thumbs digging into my cheeks. He pulled apart my asscheeks, exposing my hole, and placed his cock at the pucker. I felt a little more of a cold sensation on my hole as he added a bit more lube. Then he began to push his cock against my boipussy. I lightly flexed my hole to allow him inside with a little more ease. He slid inside me and I gasped at the sensation.

The first thing I noticed was how warm his cock was compared to the cold lube. Then as he pulled his cock out, I noticed that it didn't hurt at all. Then he pushed it back inside me. It was almost a tickling feeling in my hole and a satisfying feeling when he pulled out. When he pushed his cock inside was a new feeling to me, like unique to anything else.

He began to pick up his pace and thrust deeper inside my ass. I started to feel a little extra tickle on my taint area. I put my hand between my legs as he slowly pumped my ass to feel the area out of curiosity and felt his balls touching my taint. He felt my touch and almost growled in pleasure. I responded to that by opening my fingers to caress his balls more effectively; he responded by picking up the pace and strength of each thrust. The sound of his hips smacking my ass began to echo in the living room.

I felt a tickling sensation continue to bubble up inside me.

My mind was reeling. My heart was racing. A man was fucking me in my ass. My hole was finally getting used.

"Sissy sluuut" my brain reminded me. The porn conditioning was working.

I felt my cock wiggling and flopping around, notably limp. That was a new sensation too. Every time his cock plunged into me, I felt his balls fully press onto my taint. Then as he pulled away, his balls would peel off my taint--sticky from the lube.

The tickly sensation inside me continued to build. My instincts told me to touch my cock and pleasure myself. I resisted.

He changed his grip on my ass and grabbed the front of my hip bones like they were fuck handles. Then he started to drill my hole. The sound of his hips smacking my ass suddenly increased in volume and speed. My hole felt hotter from the increased friction from his cock pulling in and out of me and greater speed. I enjoyed every second.

My hole getting fucked was expanding my mind. It was such a different experience getting penetrated by a real cock. Experiencing a real man's hands gripping my hips; knowing I couldn't get away; feeling his cock move in and out of my boipussy at a pace outside of my control--it was sheer ecstasy.

I felt his breath on my neck, his hand shifts up my tummy to my left nipple, and his other hand begins to randomly smack my right ass cheek. All the while, blasting my hole with his hard cock and clapping my cheeks. I heard his breath begin to get more ragged and aggressive. He started the growling moans again. His pace increased again. I moved my hand from his balls to the back of the couch just simply to hold on as he started fucking me like a gorilla.

I couldn't help my self and started to whimper every time he drove his cock inside me. He liked this and completely changed his tactic from fast strokes to hard and deep thrusts. My back muscles couldn't withstand the assault and nearly buckled every time he smashed his hips into my asscheeks.

My hole was constantly spread open by the girth of his cock. I could feel the precum leaking from my limp clitty as it flopped around and spread my precum against my thighs like a spiderweb.

Suddenly, his movements fell from steady jackhammering to rigid and twitchy. He said through gritted teeth, "I'm cumminggg". He ceremoniously plunged inside me deep and became very still as his hard cock flexed inside of my hole. He could barely move. I leaned forward and reached back with both hands to spread my cheeks for him. His cock flexed against my hole, and I flexed my hole back at him.

He unsheathed his cock from my hole and gazed at the gape staring back at him--my hands still spreading my cheeks open for him. He slowly stuck his cock in and withdrew it again. He liked watching my hole eat his cock, so he kept doing it. I could feel that he was getting softer and that the condom he used had a full-tip reservoir. He tapped his cock against my hole, gently whipping me with the used condom then pushed his cock back inside my used hole.

He slowly pulled out for a final time and walked off to the bathroom. I felt stuck in that position, doggy style on the couch spreading my cheeks open to the world. My mind was swimming with what just happened. I was just a fuckdoll, exactly like the Hypnos said. I just pleasured a man with both of my holes. I felt so many conflicting emotions--horny, anxious, regret, lust. A drop of lube oozed out of my hole and slowly worked its way down my to my balls, it kind of tickled.

Eventually, I got dressed and I asked him to hit me up again, to which he agreed. I left and went back to my house. When I got in, I masturbated about 5 times in a row, obsessing over my life memories.

A new world had just opened up for me. I still wanted more...