I entered the bar as I had done many times before. The difference this time was that I was there as Annie. I was in equal parts feeling exhilarated and mightily nervous. There was always a chance that I might have been recognised but I thought those chances were pretty slim. I make for a pretty convincing girl, and when I'm Annie I look miles different from my usual self. My heart was pounding, nevertheless.
I was wearing a spaghetti strap black mini dress. In the cups of my bra (strapless) were 'chicken fillets', to give the illusion of breasts. They weren't huge (my bra was a 32B) but they were nonetheless a big part of the transformation. My makeup had been done to be attractive but not overdone and I let my long brunette wig cascade naturally over my shoulders and down my back. All in all, I think I'd done a pretty stellar job.
There was music playing but I couldn't hear it at all, a myriad of thoughts flooding my mind. I perched atop a barstool and surveyed the room to see if there was anyone here that I knew; thankfully there was not, at least as far as I could see.
I was still zoned out to all sound until I came to and heard the bartender ask, "You ordering anything, love?"
He was a nice man, bald and with a long grey beard. He was a biker, I think, guessing from the leather jacket, neck tattoo and general aura. Nice, as I say, but not at all the type I was looking for here.
"Um, yes please. I'll have a gin and tonic."
He served my drink and we chatted briefly. He asked what a pretty girl like me was doing in a joint like this. 'Passing by and wanted to pop in for a drink' had been my reply. I could tell from his raised eyebrows that he didn't believe me, but that was ok. I was pretty sure he thought me to be a genuine female though, which was the biggest relief.
We didn't talk for long as he had other customers to serve. So, I sat on my lonesome for a bit, sipping my G&T and people watching. There were a fair few people in the bar that night. My hope, why I had gone out as Annie in the first place, was that maybe I'd be hit on by a guy. I know it sounds silly, and I didn't know what I'd do if a guy did approach me, but I saw it as a challenge. This was my first public outing as Annie and I think I was seeking validation that I could 'pass'.
But as the minutes ticked by and my G&T glass slowly emptied I began to lose hope for this first adventure. 'Never mind', I told myself, 'at least you got over your first hurdle tonight: going out as Annie. Now you know you can do it! Maybe the next time you'll find someone'. I considered ordering another drink and waiting longer but edged towards leaving and going back home.
Just as I was about to grab my handbag from the bar counter and depart my seat, a guy took up position on the nearest stool. He even edged it closer to me before sitting himself down.
"What's a pretty girl like you doing all alone?"
"Oh, um, I, well, I was passing by, and, well, I thought I'd grab a drink."
I was caught off guard. I eyed him up and down and was surprised by how handsome he was. He was what you might call a silver fox: he had piercing blue eyes, a stubbly beard and pearly white teeth. I would have pegged him as early forties, even with his greyness; given the grey hair, he may well have been older, but his good looks suggested otherwise. He wore grey plaid trousers and a tight-fitting black shirt that flaunted his impeccable physique. This was exactly the sort of man I had been dreaming about!
"Well, in that case, may I buy you another?"
"Um, sure, thanks."
He ordered our drinks - mine another G&T and a whiskey for himself. We started chatting, getting to know each other a bit. Everything I told him was true: my job, my hobbies, relationship status, etc., but just changed minor details to keep up my 'Annie' pretence. He was delightful to talk to. We chatted for ages, so much so that I was on my fourth G&T (all paid for by him) when I said that I'd really better be making a move.
"Hey, it's far too early to call it a night. When don't we head back to my place?"
The promise of that thrilled me.
"Sure. But can we do my place instead?" Something about using my place instead of his just felt safer. He was a real gentleman, but I've heard horror stories before and you can never be too careful.
"Great. You lead the way."
We departed our barstools and the bar and walked the short distance back to my flat. After a short fumble in my handbag to find my keys, I opened up and let us both in. I kicked off my heels while he kicked off his shoes and I showed him into the living room. As he made himself comfortable on the sofa, I poured us both a glass of red wine in the kitchen.
I brought through both glasses to the living room and sat adjacent to him on the sofa.
"Jesus, you're practically in another postcode. I don't bite."
I sidled closer to him on the sofa, which he patted, and as I neared, he made a joke biting gesture. Startled, I practically hit the ceiling. We both started laughing.
"Oh my god! You scared the shit out of me." I gently hit him on the shoulder, still laughing.
"Sorry, I just couldn't resist."
We were gazing into one another's eyes. He leant in for a kiss, but I pulled away.
"Something wrong?"
"No, no, nothing's wrong. It's just that...well...I really want to do this, you're so good looking...its just...oh, I'm so scared to say it."
"I think I know what you're going to say."
"I really don't think you do. And it was never my intention to deceive you, everything just happened so quickly and..."
"I know you're not really a woman."
I was stunned.
"You know?"
"Yeah, I knew from the moment I set eyes on you in the bar."
"How? I thought nobody would be able to tell."
"Sharp instincts, I suppose. I've been around the block; not a lot gets past me. For what it's worth, I don't think anyone else there knew. They all thought you were a pretty young lady, confident enough to have a solo drink at a rowdy bar."
"Oh..."
I must have looked a bit despondent because he pulled me into him on the sofa and said, maintaining eye contact throughout, "I said I knew from the start, and yet I still flirted with you at the bar and asked you back to my place...doesn't that just show you how interested in you I am?"
I tucked a loose strand of hair behind my ear. "I suppose it does."
"Good." He leant in again for a kiss, and this time I didn't pull away. My mouth opened to allow his tongue to enter. We continued kissing as I manoeuvred myself atop of him, my legs astride and my booty planted on his lap. I unbuttoned his shirt, revealing his seriously ripped body. He flung his shirt aside, and I began kissing down his body, first his neck, then his pecs, then his abs. As I kissed his abs, I undid his belt buckle, threw it over my head, and removed his trousers. He was wearing tight white boxers, his large cock bulging through. I grabbed it almost instinctively and started rubbing it through the cotton material.
He got up off the sofa, lifting me with him. I stopped kissing him, allowing him to reach for the hem of my dress and lift it off and over my head. I stood before him in my black strapless bra (which housed my chicken fillets) and black thong. The bump of my caged penis was obvious beneath the thong, but neither of us made any reference to it. We stood snogging in the middle of the room, both wearing just our underwear, before he broke off and I lowered myself to my knees.
I was about to pull down his boxers when I decided there was something I had to tell him. He sensed my hesitancy.
"Everything ok?"
"Yeah. It's just, well, to be completely honest, I've never done this before. With a real, ahem, penis, that is."
"You're a virgin?"
I nodded coyly.
"It's ok, if you don't want to..."
"Oh but I do," I interrupted eagerly.
"Then just take it at your own pace. We don't have to do anything you don't want to do."
"I just don't want to let you down."
He stroked my hair and smiled down at me. "You definitely won't do that, I promise you."
After a moment's pause, I steeled myself to do this. This was something I'd always dreamed about, after all. I'd be an idiot to pass up on this opportunity, particularly with such a hunky guy.
I raised my hands to the band of his boxers and slowly pulled them down his legs. Out leaped his ginormous penis; the tip brushed my chin as it sprang free. The dildo I'd practiced on before this moment had been six inches, but this beast was much bigger. I'd guess it must have been around eight, maybe even nine inches. It was definitely bigger than most, and it was certainly much bigger than my little member, perhaps three times the length I can get it to when erect. I'm glad to have a little dick, though, as it makes becoming Annie a bit easier.
I was slightly in awe but soon regained my senses. I gave it a couple of strokes, but it was already erect. So, I wiggled forward a small amount and positioned my lips around the tip. I worked my way along the shaft and got to about two-thirds of the way down, but as I made more progress, I gagged and had to remove myself.
"You ok?"
"Yeah, yeah. Just not used to such a big cock. My dildo is small compared to you."
He laughed. I moved back towards him and recommenced the blowjob. This time I didn't gag as I got past the first six inches and managed to get all nine inches inside of me. I started bobbing my head back and forth, sucking his cock like a woman on a mission. He encouraged me as I did this, referring to me occasionally as "baby girl". I liked that.