Kelly First not last time as Kellie

So normal start of the story I had been interested in wearing any type of womens clothes for years and would take the opportunity when ever possible, started with panties progressed to the addition of tights pantyhose stockings then came leggings, skirts and so on.

My next step was fully dressing at home on weekends, late night step out to the deck while dressed just to feel the cool night air under my skirt, along with the cool breeze over my freshly shaved stocking covered legs, then came a 6 inch dildo and 7 in vibrator, and I discovered how much I luv to suck on one and push one into my ass omg I was racing down the rabbit hole to real cock.

My next step was out fully dressed late night drives finding park and rides or closed businesses to just step out for a quick walk around the car once again that feeling of that cool night air around my legs under my skirt. After a couple months of this and then going home and riding one of my toys, started watching sissy hypno, then listening almost all the time in my earbuds while doing pretty much every thing, out grocery shopping I would be listening to how much I need to suck cock, how I need to have cock in my ass, and it was working I would be leaking in my panties almost the whole day.

So I made a post for CD looking to play and got a few responses shared some pics, got some pics back but then a few flaked out, I was sorta bummed they liked my pics 5'5" 160 size 8 in most clothes I had gotten to the point of passable I was told. Then I got a response from Brian we shared pics and I he shared one of his cock and that was it, I was going to make this happen, or rather need to. His cock was not this 9 inch python, no it was a nice 6 inch average girth with nice mushroom head glistening with a little precum in the photo and I was thinking for my first time could not be more perfect, pretty much same size as my dildo with his head maybe just a touch bigger.

So we made plans, for me to come to his place in 2hrs. I went all black, satin thong and thigh highs, black turtle neck style ribbed top, with the thumb holes at the end of the sleves, and black skater flaired skirt and some calf high boots. Then did my make up made sure the wig I was wearing was good and styled, and out to the garage I went heels clicking as i walked to the car.

When I got to Brians his driveway was long and led to a nice private house, that you could not see the from the road, as I drove up to his house I parked in front of the garage, just to the right of the garage was deck with some stairs to second level.

When i looked up Brian was coming down the stairs and greeted me with a light hug and light kiss on the cheek that I felt all the way to my toes, I thought omg this is finally going to happen. He led me to the stairs and had me walk up first. I could feel him staring at my legs as my heels clicked up the stairs oh was I getting turned on. At the top stairs there was a nice size deck over the garage and on the deck there was a table and chairs and a bottle of wine chilling,

I had to smile as he poured me a glass, and the pulled out a cigarette and said hope you dont mind, I said as long as you don't and pulled my pack of virgina slims out of my clutch he leaned in and lit mine first, oh how I luv leaving lipstick marks on my smokes, and on the lip of the glass just something sexy about it.

After some small talk he asks if I would like to go inside, I smiled and said yes, as he stands I notice a semi hard cock in his shorts and i instinctively lick my upper lip just a little he smiles at me when I did he caught me and I was happy about it.

We set our glasses down on the coffee table and I sat next to him keeping my knees together the skirt rode up just to the point you could see the lace part of my thigh highs, I saw him take a good long look up and down my legs.

He then asked if I wanted to watch some porn to get things going a bit I said sounds wonderful, then he put his hand on my knee slowly stroking up and down from knee to mid thigh, I could see he had gotten harder and a little twitch of his cock, then he slid his hand little higher on the I side of my thigh just to the hem of my skirt and then slowly back down to my knee. I could feel my thong dampening as I leaked a little in my thong

I then reached over and started to rub his cock though his shorts I could tell he was going commando so I slowly traced the outline of his cock with my hand giving a nice soft squeeze, then on the screen there was a girl sucking on a nice cock and he said "what a lucky guy"

Then I said "oh no its the girl that is the lucky one, maybe I could be so lucky," with that he spread his legs as I got on my knees in front of him I reached up and pulled down his shorts tossed them to the side and there was a beautiful cock and in my eyes perfect cock with just a little precum at the tip.

I gave three stokes nice and slow to his cock and could not take it anymore, and put the head in my mouth omg in an instant I knew I had chosen the right path and I would need to do this so many more times. I could feel myself leak even more as I bobbed up and down on that cock.

Then I took him deep holding it in my mouth nice and deep, oh the practice I put in on my dildo was paying off as he said softly " oh fuck that's good," then back up to just the head in my mouth using nice slow strokes, then back deep as I could take him, then bobbing about half way, then going deep again, then just the head in my mouth swirling my tounge around the head, Then back deep I heard his breath change and his thighs tighten so back I went back to just the head in my mouth sliding my tongue under the head and the it happened my first and I knew this would not be my last load of cum in my mouth I was loving it all, the feeling of the first shot hitting the roof of my mouth, second hit back of my throat, next on my tounge, the pulsing of the beautiful cock.

I then stroked him nice and slow getting every last drop out of that beautiful cock then I showed him my mouthful of cum and swallowed, instantly my thoughts are omg want to, no, need more, I so need to do this so much more.

He helped me back on to the couch next to him, and leaned in and kissed me tounge and all we sat the porn playing in back ground making out. I noticed his cock start to come back to life so I reached out while our tounges wrestled and stroked him back to nice and hard.

He pulled away from kissing and said he would luv to fuck me, I said well I am definitely not gonna stop you, and got up and walked to middle of living room got on my hands and knees flipped up my skirt and brought my chest down to the floor, I handed him the lube I grabbed from my clutch he lubbed me up and put finger in me then two fingers pushing in and out and twisting inside of me he could tell I was ready as I was pushing back at him each time he pushed in.

Then he lined up his cock and slowly pushed in oh the feeling of that smooth head pushing into me oh l do I uv that feeling, I thought it would hurt at first but with the lubr and him not being some massive nine inch python along with the practice I had done with my toys it was perfect, I pushed my chest into the floor as he grabbed my hips and started to pick up the pace, I said omg please fuck me hard, he then would slowly pull out and slam back in balls deep hard and fast the he would then again slowly back out and repeat hard fast back in slow out he kept repeating it all I could do was moan and say oh fuck.

Then he picked up the pace his breathing changed I was surprised I could even pick up on it since I was getting so much enjoyment from finally getting fucked as I have wanted for so long, then he tensed up and he pushed in deep rocking me forward a bit and I could feel his cock swell and feel his cum shooting in me, then he did a few more strokes about half way and then slowly pulled out I could feel his cum start to leak out and I quickly put my thong back in place, as if that would hold it in, he helped me to my feet we kissed.

Then it was time for me to go, he walked me to the car I could feel the thong was soaked I leaked like crazy and the thin little material between my cheeks was soaked with his cum He said we need to do this again I said omg yes we do, I looked at his deck and pointed at the table and chairs and said maybe next time.

He smiled and said we can make that happen. But that will be another story once it happens.