Comfortably Numb Adventures Georgina
- 2 years ago
- 43
- 0
The Adventures Of Georgina Part 1 - First Time free porn video
These are the real life stories of a straight guy who becomes a sissy slut. Names and places have been changed to protect the not-so innocent! Enjoy!
Ok, who am I?
My name's George and I am a man in his early forties, living in a large town in rural England. I'm pretty normal really.
Physically I am slim and naturally thin-boned, 5'8" tall and 140 Lbs. My cock is what you would call a "grower" rather than a "shower". When cold it almost disappears due to shrinkage and when fully aroused, might make five and a half inches. I'm told that's average, but I think I'm on the small side! It's not the fattest either, but its never seemed to be a problem in my relationships.
Talking of which, my relationships until recently have all been heterosexual. I have never been remotely attracted to men, but would not consider myself homophobic either. Nothing against gays, it's just not for me.
Over the years, my boyish looks have often attracted the attention of other men and I have had to spurn their advances on several occasions.
I've been married once and had several long term live-in girl friends, but at the point this story begins, I was living on my own in a rented house, having recently been dumped!
In between these mainly vanilla relationships, I often took the opportunity to explore the darker side of my sexuality. My interests had become more varied over the years, but mainly involved BDSM, having submissive tendencies.
I have always had a fascination with feminine clothing. The feel of silky, sheer and shiny fabrics never fails to excite me. I envied women for being able to wear such sensuous clothing. How vulnerable they must feel wearing skirts that offered such easy access, with only the flimsy gusset of their panties for protection!
Naturally some of my fantasies involved forced feminization at the hands of an evil dominatrix and occasionally I had tried on my girlfriends' lingerie when they were out of the house.
Anyway to cut a long story short, I decided I would take the opportunity, while living alone, to explore my feminine side!
I ordered the sexiest underwear I could find online, together with strappy high heel shoes, fishnet stockings etc..
I sheepishly browsed in the supermarket for make-up. To avoid the strange looks from those around me, I would pretend I was on my cell phone to a girl friend and in fact shopping for her! It went something like ... "What colour eyeshadow do you want honey? They have blue, pink.... " or "do you want matte or glossy lipstick?"
The arrival of packages was always cause for excitement and I eagerly tried on my new outfits as soon as they arrived, parading in front of the mirror, tottering in high heels.
I particularly liked the way heels changed my posture and made me look more girly, causing my knees to bend, by bottom to stick out and my back to straighten. I looked pretty good, especially my legs.
I had shaved most of my body, including my "bikini" area. I guessed as it was winter, I wouldn't be wearing shorts, so nobody would see my hairless legs.
Learning to apply make-up was another matter entirely, but I gradually started to get the hang of it.
Good foundation and concealer seemed to hide most things and I'd never been particularly hirsute. My Adam's apple wasn't very prominent either, so altogether I began to look fairly convincing as a girl.
If anything, my eyes were the biggest problem. I have quite a prominent brow, but on the whole I was passable.
At this stage I hadn't ordered a wig, but I found a fancy dress one I'd used to dress up as a hippy, so this would have to suffice for the time being.
I was really starting to enjoy my dressing sessions and would potter around doing the housework and getting used to the heels. I would try to act as feminine as possible, even sitting down to pee when using the bathroom.
Sometimes I would set my camera on a tripod and take lots of selfies in provocative poses, ass in the air etc..
I felt the need to share my experiences and joined a website for transvestites and their admirers. I created a profile under the name of Georgina and added some of my raunchiest photos (face obscured of course).
My aim was to meet a dominant woman who might want a submissive man to feminize or perhaps just other trannies to discuss clothes, make-up and girly things.
It wasn't long before I started attracting very favourable comments about my photos, many complimenting me on my legs and choices of lingerie.
Soon I was dressing up every evening when I got home from work. The act of getting ready and putting on makeup made me feel very feminine and I started to notice my whole thinking and personality change. I tried to think how a girl would think.
My cock, small as it was, became an annoyance and spoiled the line of my clothes, so I stared to practice tucking it between my legs and keeping it in place with tight fitting thongs.
A waist clincher was purchased to give me more of an hourglass figure. I hadn't purchased breast forms at this stage, but I did have little man boobs anyway, which would fill an A cup.
When I was dressed I would spend my time on the chat rooms, chatting mainly to other sissies and sometimes guys. I would enjoy flirting and always tried to say things and behave as a girl would.
There were several chat rooms dedicated to people who wanted to arrange real life meets and they always seemed to be the ones with most guests. One was dedicated to people from my part of the country, so I spent a lot of time hanging out there. I would receive all sorts of propositions from admirers and other trannies wanting to meet up, but I always turned them down. I was after all looking for something different - a woman to dominate and feminize me.
It's easy to rationalise this. I was brought up to be a man. Men don't dress like girls. Men don't fancy other men. If you do either of these things you are a gay, sissy faggot! However if you are forced to do it, by a dominant woman, that somehow makes it ok! How ridiculous this sounds in hindsight!
I started to enjoy the attentions of other men more than I did the t-girls. The guys made me feel more girly and the more I chatted to them, the more I started to get aroused by the thought of being intimate with one.
It was like I had two completely different personalities. George was a proper man, one of the lads, happy to drink beer with his mates and never contemplate being intimate with another man. In fact he found the mere thought was repulsive.
Georgina on the other hand was all girl. Once dressed and made up, she felt and acted like a girl and started to fantasise about being with a man.
She wanted to be looked after, lusted after, desired and dominated! Her own satisfaction was not that important, she wanted to give men pleasure and most of all she wanted to suck cock.
She imagined how it would feel and taste inside her mouth. She imagined the feeling of strong arms holding her. She wanted to be a man's plaything and the prospect thrilled her to the core.
When I was dressed as Georgina, I was in my mind a woman, not a man, or a sissy, or a faggot.
I carried on flirting and teasing the guys in the chat room. One evening I was all dressed up and feeling very horny.
I was wearing a black bra with bright pink bows, matching thong and waspie suspender belt. Over this I had on a short grey leopard print skirt and a long black wrap-around cardigan. Fishnets and heels finished the look.
I had spent an hour carefully applying makeup. On this occasion, pale blue eyeshadow and bright red lipstick. Blusher emphasised my high cheekbones and heavy eyeliner added a bit of drama to the look.
A few dabs of recently acquired cheap perfume was a final touch.
I had been on the chat room for a few minutes, just reading the comments from various guests and exchanging greetings with new entrants, when my computer 'pinged' as a chat invite flashed on to the screen. It was from a man I hadn't spoken to previously, so before accepting, I checked out his profile. No photo, but otherwise he seemed like a decent sort and also very local. Some testimonials from other gurls seemed to confirm he was genuine, so I clicked on the accept button.
"High Georgina, how are u tonight?" He said.
"I'm good thanks" I replied "just waiting for a big strong handsome man to talk to! Xxx".
"I like your pictures, you have great legs" he said "do you want to meet up. What part of town are you in?"
Talk about getting straight to the point! I had absolutely no intention of meeting this man. He was a total stranger and I knew nothing about him, but this type of invitation always gave me a thrill. I would of course give him a good reason why we couldn't meet up.
I thanked him for his compliment and told him roughly where I lived, but ignored the part about meeting.
"I could be there in half an hour" he said.
"It's a bit late" I lied "I have to work in the morning.
"A quick blow-job won't take long" he countered. "What are you doing in this room if you're not really looking to meet up? Are you just another prick teaser?"
"I've never been with a man" I told him, hoping this might put him off.
"There's always a first time" was his reply "I don't think you would be in this chat room if it wasn't what you wanted. Am I right Georgie?"
He was right. I did want it. I desperately wanted it and my little clitty, swelling in my panties wanted it too.
I looked around the house and thought what a mess it was. I couldn't entertain a guest with it looking like that!
"Do you know how to treat a girl like me?" I asked "I need a man who can take control".
"Yes I do" he said "so what's it gonna be?"
"Just a blow-job?" I asked? I didn't want him thinking my ass was available. That would have been a step too far!
"Yes" he typed.
Without giving it any further thought my fingers tapped out my reply "OK. Give me your number and I'll text my address. I'll need an hour to get ready".
Oh my God, what had I done? I felt fear, excitement, lust and a hundred other emotions all at once.
His mobile number flashed on the screen and before I could back out, I quickly texted my address, leaving out only the house number, which I promised to text once he let me know he was outside.
I don't know why I did this. I think I just wanted to retain one last bit of control and leave myself with a way out if I got cold feet.
"See you soon" flashed up on my screen and he exited the chat room.
I stepped out of the rear door onto my patio to light up a smoke, my hands shaking. I loved the way my lipstick left traces on the cigarette and was grateful for the calming effect of the nicotine.
Stepping back into the house I set about tidying up the living room and when satisfied it was acceptable, I turned my attention to the mirror. A few touches here and there were all that was needed.
Being busy, stopped me thinking about what I had let myself in for, but the hour soon passed and my phone beeped to tell me I had a message.
It was him. He was in my street. Fingers shaking, I texted my house number and told him to look for the red door.
He must have parked very near to my house as just a few seconds later there was a knock on my front door.
As I walked down my hallway, I felt incredibly vulnerable. I'm not a strong guy and this man outside could probably do whatever he wanted to me and I would be powerless to prevent it!
Sure, I could kick and scream the house down and no doubt neighbours world come running to my aid, but did I want the whole World to find out I was a sissy slut, who invited men round to suck?!
There was no turning back now I had come this far. I opened the door, careful to keep out of sight of any curious neighbours.
"Come in" I said "nice to meet you".
I spoke softly, in a voice slightly higher than normal, trying my best to be convincing.
As he followed me through to the lounge I could feel his eyes on my ass, which thanks to the height of my shoes had a pronounced wiggle as I walked.
He took a seat on my leather sofa and I offered him a drink, whilst my eyes checked him out.
"Can I get you a tea or coffee? Beer maybe?"
"Water will be fine".
"Of course" I said "I hope you don't mind if I get myself a glass of wine!"
I excused myself to the kitchen and considered the situation while I poured drinks.
Jeff, as he had introduced himself, seemed ok. He was a good couple of inches taller than me at around 5'10", but my heels made up for that. He had a much bigger build than me, not muscular, but not fat either, just well covered. I imagined he was a similar age to me.
He was dressed casually in jeans, training shoes and a sweater. Not scruffy, but not smart. He'd obviously just come as he was.
He had a rural accent and I got the impression he was a bit of a country boy and probably a manual worker.
I wouldn't describe him as handsome, but at the same time he wasn't ugly.
Anyway, right now he was sitting in my lounge waiting for me to suck him off! My little sissy clit, twitched in my panties and I knew a sticky patch would be forming in the gusset.
I walked back in to the lounge and placed our drinks on the coffee table and looked at Jeff, wondering what I should do next. Should I make some small talk?
I needn't have worried as Jeff, in an assertive tone, said "you'd better get on with it" as his eyes dropped towards his crutch.
Without hesitation I knelt in front of the sofa and reached for his belt. It's surprising how much harder it is releasing someone else's belt rather than your own, but I soon had it unfastened together with his fly buttons and, as he raised his ass from the seat, I tugged his jeans down to his knees.
Jeff was wearing grey jersey cotton boxers and his semi-erect cock was causing an impressive bulge. The thought that this man was hard for me gave me a real thrill and I reached to pull down the waist band, eager to see him in the flesh. "God," I prayed to myself, "please let him be clean"!
His cock sprung free and immediately assumed an angle pointing up to the ceiling.
I was thrilled to see how wonderful it was. It really was one of the nicest looking cocks you could imagine, and it was big! Well big compared to mine. I would estimate about 7" long and quite thick.
Leaning over his lap I gripped it firmly in my right hand and closed my red painted lips around the head, which had forced its way out from his foreskin.
My nostrils filled with his scent. He smelt fresh and clean, just ever so slightly musky and he tasted equally as good.
I was so eager to have this this lovely man meat in me and sucked hard as my head bobbed up and down. With my hand wrapped around his shaft there was still a good three inches going in and out of my mouth.
Jeff's next words thrilled me as he groaned and called me a "Dirty whore" and then told me "This is not the first time you have sucked cock is it?"
I slipped my mouth off his cock just long enough to insist that it was, before greedily taking it back in.
How much cock could I take I wondered. I took my hand from the shaft and caressed his balls as I attempted to deep throat him.
"That's right bitch" he said "take it all".
I slowly lowered my head further down and felt his helmet against the back or my mouth, but there were still a good two inches of cock left to go. He pushed harder into me and I gagged violently as it was forced into my throat.
I hoped that if I just kept trying, the reflex response might lessen, but every time he thrust into me I began to wretch.
"Dig your thumb nail into your finger as hard as you can" he advised "it will lessen the reflex to gag".
It didn't!
Jeff pushed me away for a moment so he could get up from the couch and assume a standing position in front of his kneeling sissy.
I took the opportunity to shrug off my cardigan and noticed that my skirt had ridden up my thighs, exposing my stocking tops and panties.
I greedily reached for his cock, now glistening with my saliva and licked all along the shaft and around the head, before encapsulating it within my mouth once more.
In the standing position, he now had the freedom to thrust his hips back and forth, pounding his knob into my mouth and I had to keep my hand around the shaft to prevent it going too far down my throat.
For several minutes he continued to fuck my face. He was firm, but not too rough, seeming to know exactly how hard he could push me with out my gagging becoming a problem.
All the time, he would be offering encouragement.
"Good girl" he would say.
"Keep sucking that cock..... You know you love it....... That's a good slut... Use your tongue..... You dirty sissy girl..... That's right don't stop..........
His breath was quickening and I sensed he was getting close to his climax.
I sucked hard and bobbed my head in time to his thrusts, my hand wanking his shaft, as he encouraged me with his vocal comments.
"That's it you dirty whore, suck me hard and make me come".
I moved faster, desperate to please him and make him shoot his load in my mouth. Soon, and without warning, I was rewarded, as a jet of warm jizz exploded into the back of my throat.
Jeff was making grunting noises as he pumped several more doses of spunk into me, forcing me to swallow quickly to avoid choking.
Not a drop escaped my lips as I proudly took all he could give me and in hindsight, I wish I'd had more time to savour the taste of his seed, before gulping it down. My head was swimming, with all the new sensations I was experiencing as my tongue and lips finished cleaning the last vestiges of cum from his dick and it slid from my mouth.
I knelt there in quiet contemplation as Jeff, looking down at me, pulled up his shorts and jeans.
"I better be goin'" he said "thanks slut".
With that he headed for the front door and left me, used on the floor.
"How typical of a man is that?" I laughed to myself. "Only concerned with his own pleasure!"
It served to reinforce my feelings of femininity. I was now a girly slut to be used by men, the dominant sex. A gender I could no longer claim as my own.
I wasn't George the man, I was a sissy faggot, who pretended to be a woman.
I picked myself up from the floor and reached for my untouched glass of wine and took a large swig, washing away any remaining taste of the lovely cum I had swallowed.
As I sat on my bed later, removing my makeup before slipping into a nightie, I was already contemplating my next girly adventure.
Rowan
- 01.04.2022
- 20
- 0
George 6 Georgina The party
- 2 years ago
- 33
- 0
The Exchange Student Disciplines Georgina
- 4 years ago
- 29
- 0
