Annie |

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 tightfitting 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 twothirds 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.

“That’s it, baby girl. Does my cock taste good? Oh, oh yes, baby girl. You’re doing so well.” He held my head throughout as I intermittently put my hands on his backside to steady myself.

I kept going, enjoying the taste of his throbbing cock that radiated such a pleasant heat. All that practice with the dildo had clearly paid off as he let forth a tsunami of hot, salty liquid straight down the back of my throat. I closed my eyes in that moment, hoping to remember it forever—the first time I’d ever made another man cum. Then I removed myself and commenced licking up the ejaculate that remained on his cock. When I was satisfied with the cleanup job, I pulled my head back and looked up into his eyes.

“Was that ok?” I asked, desperate for confirmation.

“You kidding? It was the best blowjob I’ve ever had. You sure you ain’t done that before?”

I laughed like a schoolgirl and shook my head ‘no’.

He lifted me up and pulled me into a bear hug. I wasn’t large by any means but was surprised by his strength. It was so manly. I wrapped my legs around him as he held my ass cheeks to keep me aloft. I locked my hands behind his neck and gazed into his deep blue eyes.

“Shall we take this into the bedroom, baby girl?”

“If you want to, daddy.”

His eyes glistened as I called him this. It was clearly a turn on.

With me still wrapped around him, he walked from the living room and towards the corridor from which four further rooms sprouted: the bathroom, the kitchen, the guest bedroom (which I just used to house all of Annie’s stuff) and my bedroom.

“It’s the last door on the left.”

He got there and somehow managed to turn the knob with me still in his grasp. We snogged again as he took us inside before he plonked me down on the bed and crawled on top of me. He pinned my arms over my head and snogged me while his cock teasingly tickled my thigh.

He removed his hands my arms and was just lowering under my back and towards my bra strap when I stopped him.

“Can I leave my bra on? Think it’ll spoil the illusion, you know, if you take it off. It helps me to feel feminine.”

He leant into my ear and whispered, “No problem, baby girl.”

He moved his hands from behind my back, and I got up from my lying position. Without instruction, I moved over onto all fours, pushing my bottom out suggestively towards him and arching my back a bit to push it up. He took the cue and lowered my thong to my knees in order to expose my asshole. I expected him to dive right in, but thankfully he was more on the ball.

“Any lube around?” he asked.

God, I hadn’t even thought about that! Just a little reminder to myself of my inexperience.

“Oh, yeah, of course. Second drawer down on the bedside table.”

He retrieved the lube and applied a generous amount to my asshole and his cock. He worked his fingers first into my opening, then he started penetrating, inching his beast slowly but surely inside of me. I gasped as it first entered and groaned as he was fully inside. I had experimented with my 6 inch dildo, but nothing could have prepared me for the feeling of a real dick penetrating my ass. It was utterly delightful.

He placed his hands on my hips and began slowly, thrusting in and out gently. It was nice, but I wanted more. Just like he had done with the blowjob, I started to encourage him.

“Faster, daddy.”

He complied, quickening his pace. His rhythm was nice. He leant down over me, his whole body enveloping my comparatively small frame. I could feel his hot breath behind my right ear; it was heavenly.

“Harder, daddy, harder.”

Again, he complied: the strokes were much more vigorous, and my ass cheeks began to clap as they collided with his solid body on every thrust.

“That good, baby girl?” he was breathless as he spoke.

“Uhhuh, it feels so good, daddy. Please don’t stop!”

I groaned and ramped up my y talk. Between breaths I said, “Oh my god! Oh my god!” and “Your cock is so big, daddy, it feels so good inside me” and “Keep going, oh please God, keep going, don’t you dare slow down.”

How long he shagged me, I do not know. All I know is that it felt like I’d died and gone to heaven. His thrusting reached a climax and he spurted what felt like a truckload of semen straight down my back passage. He disengaged and fell back against the headboard of the bed. I was a bit slower to react, perhaps a bit stunned by what had just happened.

What had just happened? I asked myself as if needing to rationalise the situation. Luckily my inner voice was at the ready to inform me I wasn’t in a dream: ‘What’s just happened, you little slut, is that you’ve been picked up by a guy at a bar, taken him back to yours, and he’s fucked you good and proper. That’s what’s happened! No longer a virgin, you little cocksucker!” I smiled to the fullest extent I could. I was absolutely buzzing.

Coming to, I pulled my thong back up and sidled over to him. He looked spent with flushed cheeks and beads of sweat on his brow. He still looked effortlessly fit, though. I rested my head on his chest, and he stroked through my hair. We didn’t say a word, there wasn’t any need to. We just lay there staring ahead and thinking our own private thoughts.

We didn’t stir for quite some time. When we did it was so he could use the bathroom to ‘clean up’. I offered to help, but he laughed politely and said that wasn’t necessary. While he did what he had to do in the bathroom, I got changed in the spare bedroom. I wanted to stay as Allie, so I exchanged my bra and thong for a white silk nightdress with black trim. I wore no panties underneath but kept on my cage. I no longer had breasts as the chicken fillets I had been using required a bra to hold them in place. I didn’t think that important, though.

I brushed my wig and then heard the bathroom door open. I finished up and tiptoed into the living room. He was pulling up his tight white boxer shorts and searching for his shirt and trousers. He was facing me initially but hadn’t noticed my presence, giving me a chance to admire his impressive bulge once more. Even flaccid his penis was huge!

He then turned so that his tight little bum was pointed towards me. I snuck up on him and drove my hand down the front of his pants, embracing him from behind. He allowed me a little rummage but then removed my hand and turned to me with a genial smile; the fondle may have been brief, but it was joyous to touch such a magnificent thing once more. He soon found and did up his shirt while I passed him his trousers and belt. I passed them over reluctantly.

“Not staying?”

Perhaps sensing my disappointment at the obvious answer, he pulled me in and clasped my one butt cheek under the nightie. He held such power in his big hands.

“Baby girl, I want to stay more than anything. But I’ve got work tomorrow. Lame excuse, I know, but I really have to be getting home.”

He let go in order to do up his trousers. He then slipped on his shoes and socks and was at the door, ready to leave.

I leaned against the doorframe, arms folded across my chest.

“Am I going to see you again?”

“Maybe, depends on if you want to or not?”

“I do. But how am I to contact you?”

“I think you’ll find a way.” And with that, he closed the door and left. I sprinted for the door, but he was too far gone by the time I got there.

I shut and locked the front door, exasperated. How was I supposed to find him if I didn’t know his number? I was a bit upset, and made my way slowly to the kitchen. I eat when I’m upset, and so I headed for the fridge. That was when I noticed a postit note had been put up and held in place by a magnet. I removed the magnet and examined the note:

‘Loved tonight, baby girl! Let’s do it again sometime.’ After this, he had written his number.

I leaped into the air and squealed with delight. I immediately traipsed over to the living room to collect my phone and dialled in the number. He answered after one ring.

“Calling already?” He was clearly chuckling as he said this.

“How did you know it was me?”

“Gut instinct. I told you mine’s good.”

I giggled.

“So, what did you…”

“When you free next?” I interrupted.

“Easy tiger. Well, let’s see, how about…”

“You free after work tomorrow?”

He laughed again. “Sure, I’m free tomorrow evening.”

“Fab! Come round mine when you’re ready. I’ll wear something y.”

“Great, look forward to it.”

We both knew the conversation was at an end, but neither was willing to hang up. After some bargaining on both sides, we both agreed to do it after 3. Call ended, I decided to turn in for the night.

As I lay there in my silk nightie, I relived the wonderful events of the evening. To know that I had just lost my virginity to a gorgeous guy in this very room was a thrill. And to know that I’d be seeing him again the next evening was so exciting. And then to think about what might happen next, where we might take things from here, the new things he might show me,…

I eventually drifted off and dreamed about what was to come. My life as a cocksucking slut had just begun!