The Night of Surprises

*This is based on a true story, while some parts happened differently, this is the gist of my actual first time*

Tonight the night, I thought to myself as I looked into my own eyes in the mirror.

My big, brown eyes looked back at me sadly. I'd recently been dumped. Five years with a woman I thought had loved me, but she'd left me for another guy. We hadn't lived together, me living in my own place across town, but we had spent every free minute together. I was going to be lonely without her.

But, there was one way to end that, tonight, and finally do something I'd wanted to.

I rubbed my scruffy beard, there I was, a 30 year old man, but what I saw in the mirror was going to change.

You see, before I'd met my ex, I would, in secret, dress as woman, but was never convincing. After we met, I did confide in her, and she'd embraced it. She bought me outfits, taught me makeup and bought me wigs, and other accessories to complete my look. We'd spend evenings together sometimes, at her place or mine dressed in our best dresses drinking but I'd never done it by myself, and I'd never stepped outside of either of our homes, but that, was going to change tonight.

I picked up my razor and shaved every inch of my face below my eyebrows, and splashed on a little moisturiser. Then, I got into the bubble bath I'd run while i was shaving and soaked for a few minutes before setting the razor onto my body. It took me well over an hour, but when I was finished, there wasn't a hair on my body below my head. Since I'd told my ex about my crossdressing, I did keep it reasonably smooth, but tonight had to be perfect. I ran my fingers up my smooth legs, over my chest, and bald scrotum before applying more moisturiser.

I dried myself off, and carefully applied make up to my face, trying to follow the techniques my ex had shown me. I painted my nails in a deep shade of red, fingers, and toes then went back into my bedroom.

Laid out on the bed was my outfit. I'd picked out a martching red set of panties and a bra. I put them on, and put my breast forms into the cups, using tape, I made cleavage. I pulled on a little black dress that showed off my boobs, and came to about halfway between down my thighs.

A choker, some clip-on earrings, and a few bracelets were next then finished the look with my auburn, shoulder length wig.

I picked out my gladiator stilletos and tied the cord around my calves. They were open toe and showed off my painted nails. I picked up a small handbag into which I popped my keys, phone and wallet.

I took a long look at myself in the full length mirror and smiled. With my exes help, my skills had developed and I was now convincing, sexy, and beautiful. The woman looking back at me would turn heads in the right places.

I lived in a seaside resort on the south coast of England, so nowhere was far from pubs or bars, and I lived very close to a street that had a lot of them, and it was a Friday night. I'd decided I'd walk to the nearest one, order a drink, or two and go home, just to see how it felt to be out, as a woman.

I was due to meet him, so I took a deep breath, and stepped out of the door to my flat, shutting it behind me. I carefully walked down the stairs to the ground floor, and out the front door onto the street.

It was a cool night, and I could feel a breeze around my bare legs and up my dress. I looped my handbag onto my shoulder and folded my arms and began to walk, unsteadily at first - I'd only walked in these heels on carpet before - I headed to the bar.

I stood outside for wait felt like an age to get the courage to go inside, but eventually I did, and headed to the bar. My date wasn't here yet, so I swallowed hard and ordered a cocktail wincing as I heard my poor attempt at a feminine voice. I looked around, noone was giving me funny looks or staring. As far as they knew i was a woman out for a night out.

I finished my drink quickly as the nerves were getting the better of me, and turned to order another when I noticed someone appear alongside me.

"What can I get you love?" he said, smiling.

Oh my god. I thought, is he hitting on me?

I smiled back and said, in my best girl-voice "Tequila Sunrise, please!"

"I'm Mark" he said

"Anna" I said, thinking quickly realising I'd not picked out a femme-name before now and saying the first thing that popped into my head.

"You're very pretty Anna, join me?"

I don't know what had gotten into me, but I nodded and walked with him to his table, taking a seat and crossing my legs.

I must have gotten carried away with the excitement, because we chatted away for what felt like hours, knocking back more drinks, when he leaned in and kissed me.

"Stop!" I said "I'm not that kind of girl..."

"I know exactly what kind of girl you are, Anna. And I love that about you..." he placed his hand on my thigh and slowly moved it upwards brushing my panties with his thumb. To my surprise, I felt myself getting a little hard.

He leaned in again, and this time, I found myself kissing him back. I'd never kissed a man before, it felt....incredible. The roughness of his stubble, the firmness of his tongue, the feeling of his lips against mine.

More to the point, the feeling of his hand, under my dress, rubbing me.

"Want to go somewhere more private?" he asked, and I found myself nodding in agreement.

He took my hand and led me out the door, where he hailed a taxi. We got in, and kissed for the entire car ride. When we stopped, he paid, and led me by the hand inside his house.

"Make yourself comfortable" he said, gesturing toward a large sofa before leaving me alone. I sat, shaking with nerves, my legs crossed, and checked my make up in a small mirror from my bad, touching up my smudged lipstick, when he returned, and handed me a glass of wine. He clinked his own glass against mine, and we both knocked back our drinks quickly before he sat next to me again and once again started to kiss me, his hand rubbing my thigh once more.

"Stand up" he whispered, so I obliged, and he placed his hands on my waist and guided me to turn around so I had my back to him, then led me to get onto the sofa on my knees, mt arms over the back. He lifted the skirt of my dress, and slid my panties down. Suddenly free, my dick stood to attention, but he wasn't interested in that. I felt a moistness on my asshole, followed by a surge of pleasure as he rimmed me. I'd never felt anything like it, and moaned loudly as his tongue moved swiftly in and out of my hole, licking it up, down and all over, inside and out.

I thought I was going to cum just from that, when he stopped, leant over and kissed me again. I sat back down, kissed him back and found my hands wandering down to his crotch and unzipping his jeans. He burst out of them, standing erect, this huge, pillar of a cock. Bigger than mine, and rock hard.

I was committed now, I got on my knees in front of him, opened my mouth and took his head into it. I slid my lips down as far as I could, until i felt myself gag, before sliding back to the tip. I'd never sucked a dick before, but it felt like the most natural thing. Sliding up and down his shaft with my lips and tongue. He placed a hand behind my head and closed his fist around my hair, and pulled me down onto his cock thrusting his hips to fuck my face. I gagged, but kept going, his head hitting the back of my throat with every thrust. He moaned, then stopped and pushed me off his cock, placing a hand under my chin and lifting my head to look him in the eye.

"I'm going to fuck you now" he said, reaching for a tube of lube that was sat on the side table.

I nervously nodded, as he slathered the lube over his cock, and stood behind me, unzipping my dress so it fell to the floor, then I climbed back onto the sofa on all fours as he slid a finger into my hole to spread more lube there.

"This might hurt" he said "But it'll be worth it"

I braced myself, and felt pressure against my hole. I squeezed my eyes tight and gritted my teeth, trying not to cry out when I felt it give, and my ass was suddenly full. It stretched, and it hurt, and he began to slide in and out. The pain subsided and gave way to pleasure as he sped up, thrusting in and out, everytime he slammed into me, it felt like he was knocking the wind out of me. His balls slapped against my ass, and he gripped tightly on my hips as he pounded me raw.

I moaned loudly with each thrust, when he pulled out, grabbed me by the waist and threw my onto my back. He grabbed the back of my legs and pushed my knees up to my chest and slip his cock back in, on top of me now and went straight back to pounded, kissing me while he did.

I wrapped my legs around him as he fucked me. I'd never felt so vulnerable, and so out of control as I did then, submitting myself to him completely. I looked up into his eyes, saw my heels in the air behind his head, his bare chest and stomach and my thighs, wide, my cock bouncing on my stomach as his was deep inside me.

His eyes rolled back in his head, he moaned loudly, thrusted hard and held it, and then...I felt a warm feeling shooting up inside my asshole as he came deep inside me.

He slipped out and lay next to me, kissing me once more, as we lay there, him kissing my neck while his cum seeped out of my hole, I couldn't help but think that my life, was never going to be the same again.