Angie's Date Night

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Ladyboy set up on a blind date has the time of her life.
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Sitting at the bar, nursing my drink, I was beginning to get nervous. I couldn't believe that I'd let my friend, Vinny, set me up on a date. I couldn't remember the last time I'd been on a date and here I was going on a date with a man I didn't even know.

The bar was half full. Over in the kiosks there were a lot of couples. From people watching it was obvious that some were in the early stages of their relationships as they were looking intently at each other, occasionally brushing hands and laughing at what their partner was saying. Others had blatantly been together for quite some time as they spent most of their time looking at their phones, scanning the room and barely talking to each other. Then there were those in between who were still trying to keep a little sparkle in their relationships, but from what I could tell, they wouldn't be together much longer.

What all of the couples had in common was that all of the couples were plain, vanilla, one man and one woman partnerships.

In the corner of the bar was a group of guys, who looked like they'd stopped in for a drink or two on the way home from the office. They were getting a little rowdy and I had already noticed them looking over at me, checking me out. I wish I hadn't chosen my short black dress now. Vinny had persuaded me to wear it as my date would appreciate my curves. My push up bra was making the most of my cleavage and I was showing a lot of flesh, spilling over the top of my dress. And perhaps a longer dress would have been sensible. Sitting on a high chair at the bar, my skirt was only just covering the top of my sheer, black stockings. I was constantly giving a little tug on my dress to hide my modesty. Wearing these three inch heels did make me feel sexy, but right now I felt vulnerable.

I had arrived a few minutes late and expected to find my date waiting for me, but there didn't seem to be any single guys at the bar which is why I found myself sitting on my own.

With the music playing quietly in the background I had placed my chair so that I could see everyone entering the bar without making it obvious. I found myself playing with my earring whilst dangling my heel on the tip of my toe. The door opened and this cute guy entered. He was wearing a nice sweater and chinos and was a little tubby. Not quite my type of guy, but beggars can't be choosers. He walked towards me so I gave him a charming smile as he approached. He smiled back and I went to stand up to greet him.

He continued to smile and walked on by me to take another chair further down the bar.

I was so embarrassed.

This was a mistake.

I couldn't go through with it.

I was picking up my bag from the back of my chair when the door to the bar opened again. Casually I looked up and saw him. There stood a man, 6'2" tall, dark hair, penetrating blue eyes, and he definitely worked out. He was wearing a smart casual suit which fitted him perfectly. Here was a man confident in his own skin and knew that men wanted to be him, women wanted to be with him.

"Well, some lucky lady is going to have a good night, tonight!", I thought to myself as I dropped down from my chair.

As I started to leave, he was walking straight towards me, smiling. As we were passing his hand came out towards me.

"Hello. You must be Angie?"

I just nodded.

"Vinny told me how pretty you were, but she lied to me. You're beyond pretty. You are stunning."

It doesn't often happen, but I was lost for words.

"I'm so rude. I'm your date, Antony."

He bent down, rested one of his huge hands on my bare shoulder and kissed me on the cheek. I then turned and offered him my other cheek which he also kissed. I blushed as his hand and his kisses had sent electricity running through my body. This was a real man and he was my date!

"Lovely to meet you too, Antony", I managed to stammer out, "Vinny had told me you was a gentleman, but she forget to tell me how good looking you are."

Now it was Antony's turn to blush.

Now the introductions were over Antony led me back to the bar and helped me up on to my chair. Even with my heels on, my date was taller than me so once I sat down, I noticed his eyes drifting down to take in my cleavage. Rather than finding it embarrassing, I found his attention kind of cute. I even found myself leaning forward slightly to give him a better view.

Reaching behind him, Antony pulled a chair nearer and perched himself on it. Being so close, our knees were virtually touching. When I crossed my legs, the sound of my nylons dragged his gaze down from my cleavage to my long stockinged legs. I readjusted the hem of my dress to make sure my suspenders were not showing.

"So what will you have, Angie?"

"Dry white wine please. Pinot Gris if they have any."

Antony waved the barman over.

"Yes sir. What can I get you?"

"The lady would like a glass of Pinot Gris and a whiskey for me. Irish if you have any."

"Yes sir. Will Bushmills 16 year old be okay?"

"Perfect."

"And small or large wine?"

Antony looked over to me.

"A large one please."

Antony grinned and I blushed at the misunderstanding.

"A large wine please!"

"Coming right up."

The barman walked off to get our drinks and we sat wondering what to say next.

"So how..."

"Vinny was..."

We smiled at each other.

"After you."

"So how do you know Vinny?" I asked Antony

"We went to school together so I've known her well, since before... well, you know."

And I did know.

Vinny hadn't always been Vinny. We had supported each other as she had her surgery and struggled with her family's rejection. I had held her hand when she went in for her first surgery and was there when she woke up from the last of her surgeries. She had gone from being a shy effeminate young man to a wonderful, beautiful lady. She hasn't been with a man since her surgery but after a night of dancing at the local club, she would often climb in to bed with me and we'd curl up together and cuddle until dawn.

"You must be the only of her school friends to still be in touch," I prompted.

"I was working in the States while he, sorry, she... well, while she went through her transition. We were in touch via e-mail but she never mentioned anything. And then the e-mails stopped. I asked my brother if he knew what was up and he just told me to forget about it."

"Your drinks sir."

"Thank you."

We both took a sip of our drinks while looking each other in the eyes. Antony had eyes the colour of the oceans. Such a deep blue, I could fall right in to them. As he put his whiskey down, he rested his hand on my thigh. Not in a possessive way, but as if we've known each other for ages.

"So when did you find out?"

"When I came home. I asked my brother and he stuck with the line of just forgetting about my old friend. We were out drinking one night and he had one, or two, too many. A long legged beauty in a sexy black dress walked past wiggling her ass as she walked by. I had checked her ass as she passed. My brother laughed at me and asked if I remembered her from school. I told him I never went to school with her. I would have remembered if such a sexy girl was in our class. That's Aaron, he said, but he likes to be called Vinny now."

"Must have been a shock?"

"It did take a few seconds to take it all in. I was still watching her walk away and knew that I had to speak to her. I made my excuses with my brother and followed her across the floor and tapped her on the shoulder. She turned around and I saw her from the front for the first time. She smiled and was beautiful. And then her face dropped as she recognised me. And smiled at her and told her how great it was to see her. She was unsure but when I offered to buy her a drink she softened. We spent the whole night catching up with what we'd been up to since we left school. I told her about my studies in the States, how well my work had gone and why I'd returned home."

"I guess Vinny's story took a little longer?"

"Ha! Yes. She told me how she'd struggled with her inner desires all through school and had been so depressed. Until she met an amazing person who had given her the confidence and encouraged her to listen to her inner feelings."

"Really? And who was that?"

"You might know her. Someone called Angie."

I giggled and blushed a little.

"Really? I could see she was unhappy and just needed a little encouragement to blossom. As you've seen, I was right!"

"You certainly were! The more she told me about how you supported my friend the more I liked the sound of you. Vinny and I have been catching up over the last few weeks and it's been great getting to know her all over again. The other night we got to talking about you. You must know she has so much respect for you and loves you like a sister?"

"We always look after each other," I smiled thinking about my friend.

"Then she told me you was single and asked if I would like to take you on a date."

"She's so naughty! She knows the type of man I go for and, well, you tick a few of those boxes!"

Antony squeezed my thigh and broke out in to a beaming smile, flashing his white, even teeth at me.

"So here we are. You, the lady who helped my friend through the toughest period of her life when her family and friends walked away and me the stranger from school who wants to say thank you."

Antony leant in to give me a kiss on the cheek.

Perhaps it was the story he had told me and my love for my friend, but I moved my head so that we ended up lip to lip.

I think my forwardness caught Antony by surprise as he started to withdraw, but I slipped my arm around his neck and held him in for a longer kiss, looking him in the eyes as I did so. I could see the shock in his eyes at my not so subtle seduction technique, but then he relaxed and began kissing me back. As our kiss became more passionate, he began to slide his hand up my thigh until he reached my stocking top.

Our kiss was now beyond passionate. I was gently moaning as our tongues entwined inside each other's moist mouths. I began to open my legs slightly and then remembered that we were sitting at a very public bar.

Reluctantly, I broke the kiss and panted slightly as I blushed with the passion that the kiss and caressing had brought out of me. Antony took his hand off my thigh and leaned back, giving me a long hard look.

"You are amazing Angie!"

"You're not too bad yourself Antony," and I meant it. I began to wonder how much Vinny had told Antony about me.

"If it's not too forward of me, would you like to go somewhere a little more private?"

I thought long and hard about the offer. Well, at least a couple of seconds.

"You do know..."

Antony put a finger to my lips to stop me from finishing my question.

"No need to say anything Angie. I've grown up a lot in the last couple of weeks as I've become reacquainted with Vinny. Here, lets finish our drinks and head off."

"Okay. As long as you're okay?"

I don't think I've knocked back a wine so quickly. Not very ladylike, I know, but I wanted to strike whilst the iron was hot and the wine was giving me a little Dutch courage.

We both finished our drinks, Antony dropped some money on the bar, reached out for my hand and we walked to the door.

"Would it sound forward of me if I suggested we head to my place? I have a bottle of Pinot Gris that has your name on it."

"Sounds perfect!"

"Great! It's only a five minute walk."

As we walked along, I couldn't help looking up at this hunk of a man who I had just met. How lucky was I to have a friend like Vinny who had set me up with such a man. My hand felt so small in his huge hands. He was having a huge effect on me! What with the sound of my heels clattering as we walked along and the cooling breeze on my stockinged legs I was beginning to get very aroused.

I barely noticed where we were walking just enjoying the romantic night I was having.

"Here we are."

We had stopped outside the gates of what I could only describe as a mansion. I looked around to see where Antony meant.

"This is your place?"

"Yeah, I guess so. I did quite well in the States and had some luck with my investments."

I was too stunned to respond. Antony put his arm around my waist and guided me through the gate and along the path to the front door.

"Welcome to my little home."

The double doors opened on to a hallway which was as big as my entire apartment. The floor was made up of black and white marble tiles with doors off either side, leading to a wide staircase like something from a 30s movie set.

I was dumbfounded and just looked up at Antony. He was grinning down at me.

"It's quite impressive isn't it? A bit big for me all on my own. I need to find me a wife don't I?"

The look in his eyes melted me even more.

"Do you want the quick tour or the extended tour?"

"I'd love to see everything you have if that's okay."

Immediately I realised what I'd said and blushed again.

"Well, since you asked so nicely, let's have a look shall we."

Reaching down for my hand again, we walked through to the kitchen where he opened a bottle of chilled white wine, poured a couple of glasses and put the bottle in to an ice bucket. He guided me through the kitchen, showing me the gardens which included a heated pool, completely secluded from the neighours' view. Like the house, the gardens were stunning.

We then went back in the house moving from room to room, each one more stunning than the previous. A piano in one, an awesome looking home cinema setup in another. We then went to the basement which contained a gym with more equipment than I knew how to use and another smaller pool.

"So what do you think of my humble abode?"

"Yeah, it's not so bad. If you like that sort of thing" I joked.

"Haha! Well, thank you Angie. Would you like to complete the tour and see upstairs too?"

I know we'd only just met each other, but I think I was ready to trust this man. He had been nothing but a gentleman all night. I took another sip of my wine and nodded.

"Okay."

We headed up the stairs. As we reached the top of the stairs. my heels were now silent as we were walking on a lush, deep carpet. Antony pointed at various doors, opening a couple to show the bedrooms, all immaculate and furnished to the highest level. There was one door he didn't open and I didn't question it.

On reaching the last door Antony stopped, spun me around, holding my hand in his, looking down at me.

"Angie, are you sure you want to do this?"

I nodded.

"Yes Antony. Yes, with all of my heart."

And I had never meant it more. This man was going to take me to his bed and I knew that he was going to be the one.

Before opening the door, he bent down and kissed me. Our lips met and I felt myself melting in to this man. His tongue was soft, yet forceful as it probed my mouth. I leaned my head back and let him dominate the kiss. With my free hand, I ran my fingers through his full head of hair. I felt like wrapping my leg around his calf so that I could fell his rugged torso against my feminine one.

Without breaking the kiss, Antony reached for the handle behind him and opened the bedroom door. I didn't need to look over his shoulder to know that the room would be amazing.

Grabbing my buttocks, Antony swung me up as if I was light as a feather. Now I decided to wrap my legs around his waist and let him walk us both in to his bedroom. I have never felt so wanted. This hunk of a man knew how to treat a lady and boy was he making all the right moves.

Antony broke the kiss and put his half drunk glass of wine down on a conveniently placed table. He took mine from my hand and I noticed the red lipstick marks I'd left on the glass. He placed it on the table next to his and beside an ice bucket with an open bottle of white wine.

Even with my passions riding high, I did wonder how the ice bucket that we'd left in the kitchen end up in his bedroom, but I didn't linger for long on this puzzle.

Now that we both had our hands free, Antony was caressing my butt with one hand whilst caressing my nearly bare back with the other. I could feel my nipples getting harder as he stroked and played with my body. I'm sure that Antony must be able to feel them growing against his firm chest.

Talking of growing, with my legs wrapped around him, I could feel his arousal bulging through his trousers. I had both of my hands draped around his neck as we continued to kiss, then I broke the kiss and pushed away from him so I could look him in the eyes.

"Antony, now it's my turn to ask, you know about me don't you?" Antony nodded. "And are you sure that you want to do this?"

Smiling, Antony said, "With all of my heart, Angie!"

Locking my arms around Antony's neck, I unravelled my legs and dropped to the floor on tip toes, reaching up to leave a kiss on his lips.

"Which of these doors is the bathroom? I'd like to freshen up."

"You can use that one there. You should find everything you need in there."

You won't be surprised to hear that the bathroom was beautifully finished and spotlessly clean. As I opened my hand bag to touch up my make-up I could hear Antony moving around the bedroom. First I heard him put on some soft, background music, then I heard him preparing the bed. Our bed!

I looked in the mirror I applied a fresh coat of my favourite red lipstick, straightened my hair and dress and then sprayed a little perfume. One last look in the mirror and I opened the door to my future.

"Well, what do you think?" I asked.

Whilst I'd been making myself look as pretty as possible, Antony had lowered the lighting and lit a number of candles so the room was flickering nicely. He had removed all his clothing. Well, all except for his boxer shorts!

What a hot body! This man looked after himself. And he wanted me. He wanted to take me to bed.

"Come here and join me, Angie. I promise I won't bite."

As confidently as I could, I walked towards him, trying to seduce him with my womanly curves.

Offering him my neck, I said, "Well, you can nibble here if you like."

Pulling me towards him, Antony brushed my long hair aside and kissed me on my elegant neck. With his passions rising, he bared his lips and the kiss became a nibble. If only he knew what effect this has on me.

Shutting my eyes, my head dropped back as I enjoyed this passionate man devouring me. My hands dropped down towards his boxers, just so that I could feel what I was about to receive.

I liked what I felt!

Antony was now making a mess of my neck, but I wanted more.

With his attention on my neck, I eased my dress over my shoulders and let it drop to my waist. My push up bra was now in plain view. Antony's kissing was beginning to make me pant with passion. Each inhalation and the cups of my bra were struggling to contain my little breasts. I decided to let them free and reached behind my back to undo my bra.

Every time I look down and see my little breasts I get horny. I love my breasts and how they jiggle when I move. They make me feel so feminine.

"You can nibble me here too if you like."

Pushing my breasts towards Antony, he stops making love to my neck and drops his head towards them. He sticks his tongue out and just the tip brushes against my nipple.

"Oh fuck!" I moan.

The tip of his tongue grazes against the tip of a nipple and I swear my confined clitty grew an inch. Antony was teasing me and it was working. Every touch of his tongue sent a shot of electricity through me. His tongue was now circling around my areolae and I could see goose pimples in my darkened skin. I was pushing my breasts towards his lips, encouraging him to take my hard nipples between his lips.

"Mmmmmm", I moan as his tongue skips to my other breast, "Oh yeah".

I can't resist sliding my hand inside his boxers and feel his manhood. This seems to encourage Antony to finally use his lips and he begins suckling on my nipple, his teeth grazing my own hardness as I stroke his.

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