Becoming a Sissy

Becoming a sissy pt 1

I am a 28 year old mostly straight guy. My gay urges come and go in the form of wanting to release some stress and/or tension by getting my mouth filled up with a big thick cock. Or having an equally big cock go deep into my tight ass. Yes, these urges get to be intense. But they do not remain constant. So when I do feel them I make sure to fully indulge myself.

So a bit more about me. Like I said, I'm 28. About 5'11" and a thin 175-180 ish with little body hair below the neck. Not from grooming, but just more due to my genetics and blond roots. Blond hair and blue eyes. I guess just the average white guy type of attributes. I'm most definitely not well endowed, but nor am I a poster boy for micro penis syndrome either. I'd say fully erect I'm around six to six and a half inches. Enough to get the job done and get noticed while doing it.

So several months back I was chatting with a 52 year old guy online who by the name of Gary. He described himself as tall with an average build. He said he was looking to get his cock sucked off discreetly in a semi public place. We set up a meeting place in a remote park off of a paved bike trail a few miles outside of town. We agreed to meet up at a particular area at 11 pm and exchanged descriptions of what each of us would be wearing.

I casually walked around the area for a few minutes keeping my head on a swivel and eyes alert for every movement. About 10 minutes after the meet up time, I saw an older looking guy approaching. He was about 6/6'1", around 220 lbs. He walked towards me with his hands in his jean pockets and a ball cap low over his face.

"Good evening. You Nathan?" He greeted.

"Yeah. You must be Gary. How's it going?" I replied.

He Continued without really acknowledging my greeting; "Let's go back in those bushes over there" He pointed behind me to his right.

I led the way with his verbal direction. We got into a very small but very well hidden clearing. Not too dark but enough of the light from the walkway lamp posts bounced from the tops of the trees to provide ambient lighting. Surprisingly level ground with a dirt patch clearing. A perfect spot for a tent if one would be camping. I turned and faced him.

"Take off all your clothes. I want to see your naked body as you swallow my dick" Gary ordered in a very matter of fact way.

This wasn't discussed but I have learned this is not unusual. Many times I have met up with guys just to give them a blowjob, they would prefer that their cocksucker was completely nude. i imagine it adds to the turn on. Like they have control and that the guy servicing them is totally submissive.

For me, I'm cool with it too. It is a turn on for me, but I also know that if a guy decides to shoot his load on your face or anywhere else, it's saves you from having to walk or drive home with jizz on your clothes.

I removed all my clothes and tossed them to the side. I stood straight back up as I turned to him. He had a very serious, examining look on his face. "Very nice" He groaned as he looked me down.

"Turn around a couple times. Slowly" He ordered.

I did as he told me. As I turned and my back was to him, I heard him moan once again; "Mmm, I like that little ass. Gonna have to get me some of that."

This was a bit of an alert, as this was just a blowjob hook up. As I completed my rotating show, I responded to his comment; "I don't think I'm up for anal tonight, but you can grab it,rub it, or cum on my ass."

He looked up at my with a slight grin as he cradled my balls and soft dick with his warm left hand, "That's okay. We'll see when we get there" His hand felt so comforting. Like a heated blanket encompassing my entire package. He gave a few tender squeezes and fondled a bit before releasing me from his grasp to start unbuttoning his jeans.

"Go on now and get down on your knees like a good little girl and make daddy nice and hard so he can give you what you deserve" He said as he unbuckled his belt and made room to pull out his cock.

He's apparently into the daddy-son scene I thought as I knelt down and wrapped my right hand around his soft thick cock. I began by holding his meat stick against my face as I fully extended my tongue and licked every bit of his balls. I made sure to get my tongue deep under the constantly sweaty sack right by the asshole.

I stroked his cock slowly Feeling it gradually grow longer and thicker in my hand as I buried my face deep under his scrotum. My licking turned more ravenous as each time I inhaled through my nose the smell of ball sweat made me hornier and hungrier to service him. This happens to me every single time and I end up getting way too submissive.

I couldn't resist any longer. I pulled my head back up from underneath. Now facing a much harder and much much more larger cock in my hand. Starting with a few long licks from the balls up the 8 inches of shaft to the tip I opened my mouth up and began to service his glorious tool properly. With every third or fourth bobbing of my head on his cock I accepted more of it into my mouth. Every dozen or so times I forced my face closer to the base. Training my throat to get more of it in each time.

Gary moaned heavily as I went to town on his cock. "Oh my god. You're an amazing cocksucker. I need you to suck me off all the time" He stated as his eyes closed and his head tilted back in pleasure.

Not bragging or anything but I have heard guys say this before when I would be sucking their dicks. Usually they're just saying it. They never respond or hit you up again afterwards. Sometimes a guy you sucked off hits you up again because it's obviously very nice and convenient to have a discreet younger guy that loves sucking dick without expecting to have his sucked in return.

I continued worshipping Gary's cock. Now, I was completely able to get all 8 inches into my throat and press my face against his bushy pubic hair at the base of his belly. Each time I tasted and felt a bit of precum lubricating the back of my tongue and coating my throat in a delicious creamy glaze.

By now I would say I had been servicing Gary for a good 20 minutes. A very good and enjoyable 20 minutes for Gary as well as me. There's just something about sucking on big thick cocks that really just makes you unleash your true gay thirst.

At this point I assumed that he would unload his cum right into my mouth or down my throat. Perhaps with little or no warning. As I pulled his dick out of my greedy mouth to take the periodic gasp of air I looked up at him and asked: "You gonna cum on my face or in my mouth, daddy?" That daddy part even surprised me. Apparently I had passed that point I was mentioning about getting too submissive. I was certain he would say he wanted to unload on my face with my mouth open. Then I'd be told to swallow and clean his dick off after he came. I've learned it's a common desire. But he went a different route. And I have to admit it was a kinky turn on for me when he said it.

"That would be great. Next time", He said. This implied to me that he was already thinking about having me suck him again. He continued; "I wanna see my cum shoot all over those cute little ass cheeks of yours. Turn around and get on all fours."

Like an overly horny sissy little slut I smiled and slightly bit my precum covered lower lip. And doing as he told me to I quickly turned in a single motion and readied myself on my hands and knees with my bare ass presented to him like a target. Like an exposed unprotected target.

"Oh, fuck yeah" Gary groaned out a bit more intensely this time. "You're gonna love this."

I'm sure the smile on my face was fully showing a sissy greed of an immense level of sluttiness as I awaited my present. I did my duty of swallowing his great tool and now I was about to be rewarded with a huge hot load that would splatter my smooth ass like warm cream cheese on a bagel. Then perhaps he would use his cock like a butter knife and spread it all around.

I could hear his breathing become labored. I imagined the sight of him furiously stroking his log of a cock to induce a massive release. And after perhaps a minute or so he called out; "He it comes. I'm gonna cum!"

When he announced his impending explosion I arched my back down and leaned my ass a bit closer to him. And was very quickly greeted with perhaps one of the best releases I have ever felt from any of my hook ups. He let loose a massive load of hot jizz. Hitting my left ass cheek and directly on my asshole with the first two blasts. They hit with so much force it was like getting hit by someone shooting a rubberband at you at point blank range. It was so hot and so thick. And the feel of the cum on my hole instantly made me cum a bit myself.

But it didn't end there. Like I said those were the first two blasts. The third shot across my back. That felt like someone squirted a ketchup bottle on me. Or hot mayo. Still so thick and so much. The next I felt hit my upper back and neck with a bit into my hair.

He sighed very heavily as the last couple shots he aimed once again at my asshole and hit with much less force and quantity. "Holy fuck! That's so nice! Oh yes, very nice"

For a few brief moments I was in cock whore heaven. Covered in cum while completely naked in the woods on all fours for older man. The thoughts of how I would clean up or get home without looking or feeling cum covered hadn't creeped into my mind just yet.

I really didn't get time. Because what he said next shifted my thoughts from euphoria to confusion. Then quickly to surprise. I turned my sight over my right shoulder in response to Gary placing his hand on one of my butt cheeks and stretching it wider with his thumb as he stated; "You're gonna love this"

At that moment, my unsuspecting, cum coated tight asshole was met with Gary's still erect cock pushing it's head against it. I'm sure he was smiling as he continued; "I knew once I saw this ass that I'd had to feel it wrapped around my cock."

I cried out very meekly; "Oh fuck. Wait. NO. I -"

He cut me off: "It's okay boy. I promise you you're gonna love this. You'll be begging me for every inch before you know it. You've been a great little cocksucker slut for me so far. You don't want to bitch out now do you boy?'

"I don't know if I can take it" I pleaded.

"You will" he chuckled, "If you can ride cock as good as you suck it you're gonna have a lot of opportunities open up to you" He pressed his cock a bit more against my hole. I could feel my hole slowly getting opened by the thick sloppy invader.

I pleaded one last time; "But,...you came so much. How- "

He interrupted once again: "We're not done. Now you get what you really want boy" And with that, he pushed even harder. I felt the head of his tool breach by little hole as the shaft slowly followed like a marching army. I gasped out with equal parts pleasure and burning pain. Thankfully all that cum was there as lube or else I probably would have passed out.

"Ohhhhh, yessssss" I moaned as I felt inch after hard hot throbbing inch sliding into my hole and filling my gut up my pathetic dick stiffened and dripped steadily. This was just his initial penetration and slow exploratory thrust. But he went all the way in. It was as his big hairy hot balls met and pressed against my balls from behind and underneath and I felt packed full of massive meat in my stomach that I realized how correct he was.

We're not done.