T-Girl Loves First-Date Anal

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Trans girl cannot resist going all the way on her first date.
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T-Girl Loves First-Date Anal

I'd only just started being a full-time girl and I loved it when a man asked to take me out. A nice-looking man at that. I was quite innocent, but not for long.

Mike had texted to say he'd meet me at the fountain in the mall at eight. I rolled up and parked at 7:50. I checked my hair and makeup in the car vanity mirror, then I took some scent from my bag and sprayed under my arms. I was about to put the bottle back when I had an afterthought. I held my hem up and sprayed some up my skirt, feeling the sensual mist on my skin beneath. Satisfied, I swung my legs out of the door. I was looking good in my slinky black minidress and 7-denier stay-ups. The tops were nearly showing, but not quite. I wanted to look sexy, not like a whore. I took off my slip-on driving shoes and put on my black patent-leather four-inch heels. I locked the car and walked toward the glass door at the entrance. I held my head high so my hair fell prettily to my shoulders.

My heels clicked on the floor as I made my way to the stairs. When I trotted down, I looked around for Mike. Yes! There he was! A smart man with neatly trimmed grey hair. He recognized me from my photo and smiled.

"So, you're Susan," he declared.

"Yes, I am!" I replied.

He held out his elbow. I hooked my arm around it and we headed back to the parking lot. Mike had a brand-new BMW. He opened the door for me and I got into the passenger seat. I found myself stroking the shiny shifter on the center console. Mike noticed and put his hand on mine. Then he started the engine and started driving, pushing the car into gear with my hand. It was lovely to feel him taking charge of me.

The journey was just a few miles. The restaurant was part of a multistorey complex in the city center. We parked two levels down in one of the spaces in the parking garage below the restaurant. We took the elevator up.

We walked up to the desk, holding hands. It felt so right to me. The clerk found the booking and led us to our table. The dinner was lovely -- lobster thermidor. It can be messy to eat and I wasn't experienced, but Mike showed me how to break it and crack the claws.

When coffee arrived, I felt Mike's toes g touch my calf. He had slipped his shoes off, so I did the same. Very cute, I thought. I reached under the table and gently squeezed his toes. He gave me a warm, knowing smile over his coffee cup. I slowly brought his foot up and moved it, so his toes brushed my thigh. I suppose I was giving him the come-on.

He moved around the table to sit beside me. I squeezed his knee. His hand rested gently on my knee. I caressed his hand to show I liked it. Then I felt his fingers glide gently over my thigh until they reached my nude skin above my stay-up.

I wriggled slightly and whispered "naughty!" in his ear, but I was loving it.

His fingertips found the hem of my snowy white panties. Then a little further, pushing gently under the delicate lace. I knew I was completely smooth and my thighs were as fragrant as fresh roses.

I felt like a gorgeous fresh flower, ready to be plucked. I quivered as Mike's fingers walked round my thigh and touched my bare bottom.

"Very, very naughty!" I whispered once more in fake disapproval.

I hooked my leg over his under the tablecloth. Now he could explore me more freely. I decided to return the favour. When I put my hand on his crotch, I could feel his cock bulging. I unzipped him and put my hand inside, then through and on to his bare, warm dick. I pulled it out and it sprang free. I looked into his eyes as I caressed him ever so gently.

"No rush, but would you like to settle up?" the waiter asked. I was startled. Neither of us had seen him coming.

"Sure," Mike replied, paying by card and leaving a big tip.

"Thank you, sir. Have a good evening."

The waiter didn't seem to have noticed anything, even though Mike's cock was still stiff and bare under the table. We tidied ourselves up and headed for the exit, holding hands more firmly than before. I knew then we were on a mission to go all the way.

"Hope to see you again soon," called the waiter.

"You can bank on it," replied Mike, "that's the best coffee I've ever had and the sugar made it even better."

We got into the elevator for the three-floor descent to the parking.

Mike pulled me close, kissing me passionately. His hand was straight up my dress. I raised my thigh against his and kissed him back. He pulled me to him by my right butt cheek under my dress and put his other hand up and on my other cheek. He was gripping both cheeks. I knew what he wanted. I wanted it too. Even more so when he slipped both his hands down my panties, pulling them down a little, and I felt him grasp my bare buttocks. I loved it. It was already the best thing I had ever known. He wanted me and I wanted him.

"Ting!"

Oh no! The elevator was stopping two floors down. We unentwined and straightened our clothes at the speed of light. A silver-haired lady and her well-dressed, seventy-something partner, came on board.

"Good evening," said the man, "wonderful bright moon this evening."

"Good evening, sir" replied Mike.

The senior couple left the elevator to pay at the machine. Mike had paid on the app, so we headed down another floor and out to the parking area. It was late by now. Instead of going to the car, Mike led me through a staircase entrance. I knew what he had in mind. We were face to face again, Mike's hands pulling me close by his big, firm hands on my bum. He spun me round so I faced the wall. He got his cock out, slipped my dress up with his two hands and pulled my panties to my knees.

I felt the cool night air on my crotch. He put his cock between my thighs and started dry-humping me as I squeezed his cock between my legs. I could feel how hard he was. I wanted him inside me.

"Fuck me, Mike!" I said, my voice echoing a little too loudly down the staircase.

I rummaged in my bag and handed him a tube of booty lube. He flipped up the lid with his thumb and quickly lubed his cock. I felt his helmet touch my hole. My hole kissed his cock as he pushed just a little way into me. Then out. Then in again. Ever so gently. Tantalizingly. I trembled with anticipation.

Just then, I heard voices and footsteps.

"Mike!" I hissed. He pulled out.

Again, we put everything away and stood demurely, holding hands, looking through an opening to the bright, full moon.

A young couple passed us, hand in hand. They smiled knowingly at us and we smiled back. As they walked down the stairs, her hand was in her boyfriend's jeans' back pocket. She gave his bottom a quick squeeze as they turned the corner out of sight.

I turned to Mike. He kissed me hard as his hands went straight up my skirt and yanked my panties back down. I unzipped him and pulled his cock out of his pants. It was stiff in my hand as it sprang free. Mike turned me to the wall. I fumbled for the lube bottle in my bag and handed it to him He was caressing my bum cheek with his left hand and lubing me up with his right. One finger in me, then two, then three.

"Mike, I need your cock in me now!" I heard myself say.

For a pre-date anal virgin, that was quite a declaration!

I felt his big hands on my hips and his solid body against mine as he took control. He was in further than before already as his helmet entered me with a single thrust. He knew it would be a bit painful to start with and he stayed still.

I waited until the aching died away and then reached back and pinched his ass to let him know. He pushed gently a little further in, and then started slowly pumping in and out.

"Oh Mike... oh I love this," I cooed.

Then he teased me by pulling all the way out and spanking me on each cheek, telling me I was a very naughty girl. The little smacks echoed down the stairs. Then he thrust into me again, much deeper. The sensation made me unbelievably horny and I relaxed completely. Then he was in me deeply. So deep I felt his jeans touch my cheeks. He was bumping me as he pumped. In full control of me. My panties were at the floor. I kicked them off and raised my butt, with my feet apart, bracing myself against the wall.

I felt Mike's jeans drop away and heard the rattle as his belt buckle hit the floor. He wanted his bare skin against mine. I loved that.

"Get right in me, Mike!" I yelled.

And he did. I loved to sense his pleasure in my body. His bare, hairy crotch was against my smooth bare ass like a soft brush. I squirmed and squeezed him inside me with my ass. We cared about nothing else now.

I reached back and felt his tightening balls, touching them ever so gently with my fingertips. I started to drip precum. I was in ecstasy and I knew I would cum before long.

"Cum in me Mike! Cum in me!" I yelled, knowing it was risky. Mike pulled out quickly and put on a rubber, then he was in me again, pumping hard. I just wanted him right in, like he was in my tummy, two becoming one.

"Mike, I'm cumming!" I shouted, reaching back and gripping his muscular thigh.

He gripped me hard and shoved as deep in as he could go, I pushed my ass back on him, bracing my hands against the wall and spreading my legs. Leaning as low and open as I could, bum pert to the night. Mike held me really tight. He was deep inside my body as I felt his cock pulsing.

He starting making appreciative sounds with each deep, short thrust as he approached climax.

"Oh, Susan, darling!"

"Susan, my love!"

I was screaming with each push.

"Oh!"

"Oh Mike! Yes! Yes!"

I came in a way I had never known, squirting cum each time his balls pressed my ass.

"Oh Mike, keep going! Oh!"

He was holding me more and more tightly, to cum in me as deeply as he could.

"Susan! Susan!"

He pulled me to him really hard one last time, with his dick right in as far as it would go, holding me tight as he pulsed his cream to that place deep inside me.

I felt his body stiffen like a rock and then relax. We stayed like that, panting, for at least a minute.

Then he pulled out slowly and took the laden rubber off, casting it into the bin by the wall. He turned me around and kissed me softly and lovingly, stroking my bottom with his fingers inside my crack.

I took a wet wipe from my bag and knelt down in front of Mike. I cleaned his cock lovingly, all over the skin and his helmet. I kissed his helmet and looked up into his eyes.

Could he go again? I wondered hopefully. I caressed his still-bare bottom with my soft hands, and planted quick, soft kisses on his cock.

"Mmmmmm," he murmured.

His cock started to lift a little. I looked into his eyes again and played the tip of my tongue right on the end of his dick.

"Oh, that tickles!" said Mike.

I put my lips more tightly round his cock and sucked him as I worked his helmet, playing on it with my tongue at the same time.

He was getting much stiffer now. I kept going, letting my fingers explore his bum crack. I could see that he liked that. I touched his hole every now and then.

"Susan, on your back, darling!" Mike commanded.

I was glad to obey. I put my bag under me to make it easier for him to get inside me. Then his cock was in me and my legs were wide and in the air. I could reach his firm thighs as he pushed in and out -- more urgently than before. He looked into my eyes with joy. I loved to see him owning and enjoying my body. I knew he would cum more quickly this time. He did, and so did I.

He rocked my legs right back, so my feet were nearly behind my ears. My fingers were on his balls as they tightened, pumping their cream through the veins of his cock.

I looked demandingly into his eyes.

"Yes, Mike, yes!"

I pushed back and gripped his cock inside me, sucking his juice from him with my body.

"Susan, my love!" yelled Mike, not caring who might hear.

Slowly, he relaxed and so did I. We lay there in that risky, public space for what must have been five minutes. Then we gazed into each other's eyes, half with delight and half with surprise. A little embarrassed. We both felt suddenly conspicuous. We stood quietly, retrieved our clothes and put them on, as demurely as one would in a tennis club dressing room.

As we strolled arm in arm to Mike's car for the journey home, a Range Rover left its parking space. The driver flashed his lights once, gave a tiny toot, and waved to us as he passed. Had he seen anything? We would never know.

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11 Comments
comegentlycomegentlyabout 1 year agoAuthor

Thank you for the compliments x

69pat6969pat69over 1 year ago

Anal fantasy. I could the cock in my ass while reading this story.

AnonymousAnonymousover 1 year ago

Well written. Being in a public place, taking it deep in the ass, knowing you might get caught, is so exciting. I know I would be standing erect, feeling the piston like penetration and Mike's balls slapping mine with every thrust. Then after the first load, the realization of what just happened in the stairway, the feeling of your backside so stretched, freshly pounded, and wanting more, I could see the second time just wanting Mike's load deep in me, either end.

AnonymousAnonymousalmost 2 years ago

Bareback is always best. It will usually send me over the edge if not already there. Feeling ropes against my prostate is heaven. Makes me think of how I was such a whore. Driving home with as many as 8 loads in me making my panties soaking wet. Feeling the glow from the wonderful seed inside of me. I would love to be the receptive bride of a 2 Gurl couple. Feed me, seed me, breed me. Gurls are much better them men. Feeling our nyloned legs rub together while on my back is so wonderful. I pulsate with desire as I write this. xoxo

NewOldGuy77NewOldGuy77almost 2 years ago

Sweet, and nicely done. No condom the 2nd time, naughty! Can't wait to see where the relationship goes next...

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