u/KinkyPerversion

The Real Dairies of Sissy!

Upon a muggy, sticky , summers night I found myself home alone for the evening. In fact , the rest of my family had left for a vacation. A vacation that I opted to stay home and skip it. I was 18 years old and I was secretly dealing with an identity issues. So I was so happy to have 7 days straight by myself. It was going to be a glorious week and I was excited. I had gotten serious about being a girl. After all, I had always felt like one. And I planned on living out every day of those seven days ,as a girl. My older sister was an absolute clothes addict. She had a walk-in wardrobe full of different outfits. We were very close in size and the fact that some clothes were a little tight on me, looked even better. And even though she took a lot of her clothes on vacation, she had so many outfits that it left me with enough to pick and choose. So as soon as they left, I ran to my sisters room. I Rummaged through her closet, put together an outfit ,and put some others aside as well.
For this evening I choose a short black mini dress , with back heals to match. I had recently bought myself a good supply of panties and I picked out a pair of black thongs . I also had purchased a cute pink chastity from a novelty shop and I couldn’t wait to try it. I had been dildoing my smooth young shaved pink pussy for about a year at this point. I enjoyed making my dick, as I always referred to it, as my clit , leak as I put pressure on my Gspot.

So I squirted a good amount of strawberry scented lubricant up my pussy for my plug. A few days prior, I just bought a new larger size plug. It certainly was a challenge to get it in due to the fact that I wasn’t use to it. As I inserted it into my pussy, a good amount of precum leaked down my leg.I even covered my chastity with slightly larger jar to collect any cum that leaked out. I never wanted to waste any of it. I had been eating own Cum for a long time. It was exhilarating to eat and Taste it. I grew to love the smell and the taste. I developed a secret obsession with Sperm. I consistently fantasized about tasting another mans spunk. I wondered how it feel having a real cock cum on my mouth. I yearned to find out. However, I was taught by society and my peers that being a fag was a bad thing. But that fact, made it even more alluring to me. And loved feeling of my pussy ( asshole) being penetrated. It instantly made me feel like a girl. Knowing that I can cum from getting fucked like a girl, called to me constantly. So the only thing better than a toys , was the real thing.

As for that night, I wanted the real thing. I wanted a cock. A mans cock. I wanted to be a girl for a man and feel what’s it was like to be a submissive. I had been planning this for weeks. I bought a 8 ball of coke earlier in the week from a dealer at school and couldn’t wait to start getting in that. I had recently discovered that cocaine fueled my sexual urges. I know it literally turns me into a depraved dirty slut with no inhibitions. I needed it to go through with my plan. I wanted to go all the way. I have been practicing my sucking skills on a 9 inch dildo everyday for a year. Used porn as my tutor to instruct me to do it properly. I conditioned myself to be completely feminine when sucking my dildos, just like how girls give head. And practiced my deep throating skills. I became very capable of taking a great measured cock down my throat.

Finally, I showered, shaved , cleaned my pussy with an enema, painted nails and applied moisturizer. I reapplied the scented lube up my pussy and put my plug back in . Locked up my clit and it would not be opened til the vaca was over. Then, I began to apply make up and transform. I had been growing my hair out for almost a year and it was just above my shoulders. I was proud of my hair. It was brunette, wavy and slightly layered. It looked very feminine when I wanted it to. So when I put the black dress on, everything came together. The dress fit perfectly. It showed my butt off , really well. I was so turned on I couldn’t wait to leave.

I knew exactly where I was going. There is a rest stop off of the highway about six miles from my house. About two weeks earlier I found out that it’s a cruising spot for gay men. I went twice before and I just couldn’t get enough nerve to do anything . I knew , I had to go there as a girl. I fantasized about it constantly, as the days counted down for my parents to leave. And now, the day came. I was a bit nervous with excitement as I got into the car. I drove the 10 mile ride and my heart was pounding as I made me way off the highway and pulled around the long curves exit for the rest area. I notice that the place was pretty busy. Cars where parked all though out the parking lot. I felt nervous as I found a spot to park in the upper parking area . As I pulled in, I shut my car off and rolled down the windows. It was very warm that night. It was mid July and during a heat wave . Inside my car was quiet. But outside I can hear the cars and trucks speeding along on the highway. I was still very nervous until I set up a big choker line of coke. I was barely able to snort it all in one swoop. There was still some left and I quickly snorted it. I lick my finger and stuck in the bag. There was a good amount on my finger and rubbed my teeth with it and swallowed it . I brought knees to my chest and legs went spread eagle in my front seat. I reached between my legs , and pulled out my plug. I then licked my finger again, stuck it in the bag and got a very large pile of coke and began shoving it in my pussy. I finger myself as the Cocaine took ahold of me. I was no longer nervous, my inhibitions were gone. I finger fucked myself for a good while. Until a car pulled up next to me. I put legs down, but the plug wasn’t all the way in. It was almost in as I wiggled my ass on my seat, and it gave much resistance as it went deep into my now numb pussy. Suddenly it broke through and pressed hard against my G-Spot .
I was squeezing my plug with the muscle of my hole. I could feel Cummies dripping out. The guy in the car was looking at me. I kept my focus on my cocaine loaded pussy and he waved me at me . I smile and looked away . He got out of his car and walked by the front of my car. Then he proceeded to walk across a grass divider, that’s was in front of where I was parked , to another parking lot for campers and smaller trucks. He then turn and stood facing me, in the wood line just about 50 yards away. At that moment, I was leaking so much that I thought I was going to fill the “ cummie jar” right there. I was so lost in a state of bliss as was grinding the plug against my prostate. I had to gain composure as I located him in my line sight. He was an older white man. Probably in his 60s. He had salt and pepper hair , def more salt than paper. He had on a white t-shirt and blue jeans. As he stood in the wood line I notice he was stroking his cock. Instantly I knew that it was my chance, and I knew I wanted it. Instead of waking over to him , I drove. I pulled about 20 feet up from him and got out. My throat was numb from the massive line I took. I wanted nothing more than to put his dick in my mouth . I walked right up to him and got directly on my knees.

There it was. Another mans cock right in front of me.

He ask me if I was a girl and, I looked up at him , and replied
“I wish “

“ You sure look like one. I couldn’t even tell. You even sound like one” he replied

I was on my knees in a wide open place. I knew that mostly anyone can see us if they just looked our way. But I didn’t care. I only cared about sucking this strangers cock.

He ask
“You want to make me cum ? Huh? You want to suck on this cock ? I’ve been edging all day. You sure you can handle it”

From down on my knees , and looking directly at his cock. I was only a few inches away from it. My mouth, though numb from the cocaine, was watering. I could smell his dick. It was the first time I had ever gotten the chance to know what a mans cock smelled like. The aroma was intoxicating. It captivated my sense and formed a mental imprint of how cock smells. I knew I loved it before I even did anything . As I was merely inches from his erect I could l see a good bit of it in the dim light.

Finally I nodded

But I couldn’t really formulate any words. I froze for a moment as a moment of panic set in. Just then I had felt my nose start to run. so I quickly snort it back up. To my delightful surprise it was a bunch of cocaine that must of been in my nasal passage. It Brought me back to what I was seeking.

He said “ Go ahead . Make it cum .” He said, as he grab his cock and slowly stoked it.
He had an average size cock. about 6 or 7 inches. It wasn’t particularly thick, however , but it had a nice mushroom head. And it curved up. His pee hole glistened with precum when it caught the reflection of surrounding light. There was a good amount of it too..He was hard and ready. My heart was speeding as I knew it was time. I had trained for this and I was set to do it right. I pressed my two lips against the tip and kissed it. His cock twitch up and quickly back down. His precum smeared my lips. I pulled away as I licked my lips. I got a good taste of it and it was delicious. The flavor of his pre-cum send me over my heals. I again kiss his cock, and this time I didn’t pull away I slide my pretty pink lips over his head and stopped there . I sucked as much of his precum as I could . I kept very high suction around his Cum cover head. I used my tongue to swipe over his pee hole and then circling his cock head. I could feel the pronounced ridge of his swollen mushroom head with my tongue. The sensation of a real one, was different from its synthetic counter part. And it felt so right.

He let out a moan

He said “ Oh you are something else kid. And You are a very pretty girl.”

I was too busy to reply. I was sucking his precum like it was the most tasty dessert I ever had. I then swallowed , and went for his balls like I learn from the porn movie. I pressed my face into this strange old mans ball sack. I began lightly licking underneath them. I reached up with my left hand and gripped his throbbing cock. I sucked one of his balls in my mouth and I lightly moaned.

“ Oh yeah ! Suck my balls.” He said in a half moan

I suck on his balls for a tiny but more. I was very surprised and relieved that he was freshly washed. He tasted yummy as I pressed my lips to the bottom of his shaft and I stuck my tongue on it . I lick up from his balls to the top of his cock head. He had gathered more precum from his pee hole as it was about to dripped down his shaft. Once again I slide my lips over his cock head and began go suck all of his precum. Precum taste so good to a “Cum Goon” like me and I wanted more. I pulled slowly off his cock head and kiss it again. I kiss it as I swallowed this strange old mans Spunk. I then wrap my lip around the the tip of his cock and I slowly work my way down his shaft. I made sure that kept constant strong suction as I slid down his cock. I was half way down his cock when I stop and slowly reverse my lips back towards the tip. Then again I slide down his cock. I would go a little Further down each time. As I slide down the last time I was able to press my lips hard against him as I had his entire cock in my mouth. I just stayed there I pressed hard into him. I was swiping my tongue at the base his shaft. His cock pulsated twice as I could feel him get harder.

He abruptly said

“ Damn it, you can suck a cock. You’re gonna make me shoot my load in no time”

At the moment needed a breath and I pulled off and immediately went right back down . I slammed my forehead and Lips against his body as he bottomed out. I repeated this 4 more times and then I pulled off, took as deep breath and went all the way down again.

The stranger grab the back of my head and began trying to force his cock in deeper .

“ Oh yeah. Take that dick in your throat. That’s a good girl”
He encouraged

At this point I gagged and pulled off. I had an immense amount of salvia and I spit on his cock and began sucking him all the way down again and back up repetitively. I try really hard to keep suction but it hard to do when your bobbing your head back and forth in such a speed. I pulled slightly down on his cock and gave it some resistance. It must of gave the stranger alittle more sensation, because his cock tighten up..I didn’t stop sucking like that. I would stop every once in a while at the base of his cock, deep throating him.

Suddenly he said “ oh I’m gonna shoot”
So I pulled back a little bit and began mouth stroking him over his swollen cock head.
I felt his cock harden , and twitch .
Suddenly he let out a groan like a wild animal

“ Ohhh yeah !!! “ He yelled
And I felt and endless jet of cum hit my the back of my throat. It was powerful and thick. After that one huge blast, I felt him pulsate a couple times.
He still groaning and moaning as he emptied himself completely. My mouth was absolutely full . I was leaking a good amount of spunk as he blew his old man sperm into my mouth. It was intense to feel a man lose control to an orgasm from my doing. After he settle down I continued to clean his cock and suck as much I as I could out.
He stepped back, and put his cock back in his pants.
“ I hope to see you again “ he remarked , as he walk in the direction of his car

There was so much cum In my mouth , it was dripping out of the Corners .

I walk to my car and spit the mouthful out into a jar I bought with me to save Cum. I look at his cum in under the light and I smelled it. I took a sip and swallowed some. It smelled sweet and clean. It tasted a bit sweet. I was in a different world. I couldn’t believe I had gone through with it. I was completely buzz from the sexual high . Not to mention the coke. I kept playing his powerful cum shot over and over again. Feeling his cock tense up, pulsate and then slam my throat and mouth with a thick load was better than I ever imagined. I knew, at the moment, that his cock was just the beginning.
Jillian Jordan