First time out, first time fucked.

I was looking good even if I do say so myself. Six inch black platform heels, black hold ups, the obligatory little black dress, long red wig and my fave faux fur jacket. I felt sexy, I felt like a slut and I wanted the world to see me.

I hadn’t been out before but I had been building myself up for this moment for months. I had it all planned. Wait until dark, slip on my sweatshirt, tracksuit bottoms and trainers over my stockings and dress, stick my wig, shoes and jacket in my rucksack. I’d have to risk it in case anyone saw the make up but I figured it would be dark enough for no one to notice, especially if I wore my baseball cap low.

I was excited and nervous but taking a peek outside realised it was now or never. I quickly locked the front door and slipped into my car. Within a minute I was off the drive and heading towards the park on the other side of town. It was late out and there wasn’t much traffic, but the nerves were building and I don’t think I would have noticed either way.

I pulled up in a dark area of the park’s car park, not too far from the entrance but far enough away that I wouldn’t be noticed getting changed. I changed quickly, putting on my shoes, wig and jacket. Quick check in the mirror and I was ready.

The first thing that hit me was the breeze on my legs. I had shaved them earlier and the sensation was electric. I could resist running my hand up my stocking clad legs. I could have been happy with that but I was determined to see this through.

I gently eased myself out of the car trying to look as ladylike as I could just in case anyone was around. A quick glance around told me that there wasn’t and I quickly locked the car and headed for the park entrance. The click of my heels on the pavement excited me. It was turning me on to know I was making that sound. I continued into the park concentrating on my walking and swaying my hips. I’d practiced plenty of times at home but this was different and delicious.

The sound of my heels as I sashayed through the gates was extremely erotic. I was so caught up in how much this was turning me on that I didn’t notice him until he stopped in front of me. “You haven’t seen a little dog around here have you?” he asked.

I quickly looked him up and down. He was late 20’s about 6ft 1, athletic with short brown hair and very cute looking.

“Er, no.” I replied in my best feminine voice.

“Actually, if I’m honest I haven’t lost a dog. I just needed an excuse to speak to you. Hi, my name is Simon.” He offered his hand.

I was quite sure what to do. I hadn’t planned on speaking to anyone.
“Erm, hi I’m Sarah”. I’ve no idea where Sarah cam e from but it was the first name that popped into my head.

“Hi, Sarah. What brings a pretty girl like you to the park late at night then?” Simon enquired with a twinkle in his eye.

Before I was able to reply he continued “I saw you getting changed in your car and was curious but as soon as I saw your legs. I knew I had to speak to you.”

“You saw me getting changed?” Shit! I thought I had been so careful. I was beginning to panic.

“Don’t worry. I’ve always been an admirer of girls like you. Your secret is safe with me.” He must have sensed my panic. “In fact I’ve dated quite a few, but I have to say you are certainly one of the sexiest I’ve met.”

I was a bit surprised by his openness but also flattered by his comments. I couldn’t help but blush.

“Thanks, but I bet you say that to all the girls.” I was trying to be modest but I loved the attention.

“Honestly it’s true. Here feel for yourself.” He took my hand and placed it on his crotch. I could feel his hardness through his jeans. He felt big and I could feel him getting bigger as I touched him.

“Wow.” I let out an involuntary gasp.

“See my cock never lies.”

I had never felt another cock apart from my own and it was certainly bigger than mine and seemed to be getting bigger. I wondered how big it would get and what it would taste like.

“Here, come with me.” He grabbed my hand and led me towards the bushes. We passed through a small gap and were suddenly in a small clearing surrounded by bushes and trees. He stopped next to a large tree and turned and kissed me.
It took me a bit by surprise but I responded eagerly as his tongue explored my mouth. I could feel his hands trace their way down my back and rest on my ass giving it a squeeze. I was in heaven and let out a soft moan as our kiss continued. He pulled me into him and I could feel his hardness pressing in to me.

My hands moved to squeeze his cock. It felt so good and so big I just had to see it. I started to unfasten his belt. He realised what I was doing a broke our kiss and to unbutton his jeans. I stepped back as his jeans fell down past his knees releasing his glistening cock. It was the biggest one I had ever seen and must have been a good 13-14 inches long. It looked so good I knew I had to taste it.

I dropped to my knees in front of him with his cock pointing straight at me. Like a school girl unsure about licking her first lolly I stuck my tongue out to taste it. It was slightly salty but also delicious.

“Why don’t you kiss it?” I heard him pant.

I lent forward and gently kissed the tip of his cock. I hadn’t tasted cock before and was unsure what it would be like but here I was wanting desperately to fit it all in my mouth. I continued to kiss his cock enveloping his cock head in my mouth. I began to twirl my tongue around his cock trying to savour the taste of it.

I must have been doing something right because I began to hear him moan and gently thrust his hips forward pushing his cock further into my mouth. His thrusts were gentle but were becoming more rhythmic. I had only ever sucked on a dildo before and it was nowhere near the size of Simon’s cock. I was worried I was getting out of my depth as he thrust more and more of his cock into my mouth.

I slipped his cock out of my mouth and began to kiss along it’s shaft. I kept alternating between taking as much of his cock in my mouth as I could and kissing along his shaft. Although I was enjoying it, and judging by the sound of him so was Simon, I knew that I was also a little scared of trying to deep throat his huge cock in my mouth.

Suddenly Simon lifted me to my feet. “That feels sexy babe but it’s your turn now.” He said turning me so I was facing tree with him directly behind me.
He lifted the hem of my dress up exposing my panty covered ass. He started to fondle my ass and then I felt him move my panties to one side and start teasing my hole with his finger. I loved having my hole played with and Simon’s touch was electric. He stroked and caressed around my hole and suddenly I felt something warm and wet enter it.

It took me a moment to realise that it was his tongue and he was literally tonguing my ass. It was heaven and I couldn’t stop from letting out loud moans and pushing back onto his heavenly tongue.

“Oh, fuck babes that feels so good.” I said encouraging his tongue deeper into me.

He was driving me wild. “Oh, god. Fuck me! Fuck me! I need you inside me.”
If I had thought about it I would have had second thoughts about screaming that out but I was so turned on I just wanted to have him in me.

“Fuck me Simon! Make me your slut.” I was caught up in the heat of the moment.
Simon stopped tonguing my ass and stood up behind me. I could feel the heat of his cock pressing at my boy pussy. I began to push back hungry to get his cock in me.

I had fucked myself with dildo’s before and regularly used a small butt plug on myself but nothing prepared me for the pain I felt as Simon’s cock head pushed into me. I screamed and Simon stopped pulling out of me.

“Do you want me to stop?” He asked.

“No!” I wanted his cock in me so badly. “Just take it slow so I can adjust. I’ve never had a cock as big as yours in me.” It was true but there was also some bravado in my words as I wasn’t sure I could take his cock.

Simon worked his cock slowly into me, letting me adjust when the pain got to intense and get used to his monster. Eventually he was completely buried in me. I had never felt anything like it before. There was still a bit of pain but that was being replaced by a fullness and a feeling of euphoria than I had managed to fit him all into me.

“You okay?” He asked.

“Yes, just take it slow at first.”

He began to slowly slide his monster in and out of me. The pain and concern quickly subsided as the waves of pleasure and lust for his cock I was feeling began to build. I started to push back encouraging him deeper into me and he responded by upping the tempo.

“Yes, babes that feels so good. Fuck me hard make me your bitch.” The pain was gone and I was in pure ecstasy.

“Faster babes. Fuck my little slut ass.” I wasn’t sure where my dirty talk was coming from but it had its desired effect as Simon began to really pound his cock into me. I braced myself against the tree to stop from falling over.

“That’s it babes. Pound my tranny ass.” His cock seemed to grow bigger in me causing waves of pleasure.

“Oh fuck.” Simon called out. He was really pound his monster cock deep into me and as he tightened his grip on my hips I knew he was close to cumming.

“That’s it babes, cum in your tranny slut’s ass. Make me your bitch.” I had never been this turned on in my life but I was desperate to make Simon cum in me.

Suddenly I felt his cock explode in me with spurt after spurt of hot fluid coating my insides. It sent me over the edge with pleasure and I’m sure I blacked out a little. Simon held his cock in me until I regained my composure. Eventually he went softer and began to slide out of me.

“Wow. That was quite a show you two put on.”

We both turned in the direction of the voice…

To be continued.

99% (91/1)
 
Categories: Shemales
Posted by Shimmerts
2 years ago    Views: 2,061
Comments (30)
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21 days ago
Extremely HOT!!!
2 months ago
omg that was great
2 months ago
nice story
4 months ago
...and yeah- just so everybody has some imagination (and I think that is what you intended), that was my fruff voice exhaling smoke and watching you- my bitch wife- get fucked!

There is nothing like leaving the sequel open to imagination!
4 months ago
Honey, as excited as you were taking dick, you would be fucking gaping your jaws when I pulled down my zipper!

Guy
8 months ago
Part 2 pleassseee, :)
1 year ago
hot story! I love the ending... looking forward to the sequel
1 year ago
Wow, great story! Cant wait to read the continuation!
1 year ago
What fun!
1 year ago
Lucky Simon to have the honor and pleasure of such a Gorgeous Sexy "Lady"
BBWCuntlo...
retired
1 year ago
Nice!
1 year ago
great story honey!
1 year ago
Great story how about a sequel?
1 year ago
Great story. Can't wait to find out who the voice belongs to.
funsearch5
retired
1 year ago
wow thats a hot story! I need to read the next part
luv2cream
retired
1 year ago
wow
1 year ago
love to be in your ass :) x
1 year ago
Thanks for a hot story!
2 years ago
Great story
2 years ago
Wow!!! Can I be 'Simon' next?
2 years ago
OMG, that was a hot story. Getting caught changing in the car kinda sucks though. Glad he was cool with it.
2 years ago
Great story :)
2 years ago
Oh that got my cock hard and would love to slide it into your hot ass.
brook2012
retired
2 years ago
love your look and stories
2 years ago
now i have to read part 2..great story!
2 years ago
Cannot wait for part 2 one of the hottest stories I've read on here .
2 years ago
luv it...cant wait for the next one
2 years ago
Super Hot
2 years ago
great story! Cant wait for part 2
MrSpockYo...
retired
2 years ago
Cannot wait for part 2