Sophie’s First Meet – A work in progress

First time writing….
This is a story I’m working on. Just posting this begining to get some feedback and see how it appears on the site.
Hope to have more / completed story up soon!

Part 1; Prologue

I picked up the suitcase and carried it down to the waiting taxi. I gave my wife a hug

“Look after yourself while I’m away. I want to come back to find the house still standing!” She said
“Dont worry about me. I’ll be fine” I answered. “You just enjoy your trip”.
“Not much enjoyment to be had with a week full of meetings! Now… I’ll see you next week. Don’t do anything I wouldn’t do!” She joked.
I just smiled and couldn’t help thinking to myself “if only you knew”.
I gave Emma a last hug and a kiss goodbye and waved as the taxi drove up the road and round the corner. Once she was gone, I walked back to house and closed the front door behind me. Now it was time for my week of fun to begin…..

I should probably tell you a little bit about myself. Well, I’m just your average 30 year old man. Married (as you might have figured out!), both of us with a fairly boring but well paid office jobs, which allows us to live comfortably, and allows me to treat myself to the finer things in life…. Nice car, high end home entertainment system, good clothes. And like in most relationships, no matter how happily married we may be, we all have our own little secrets that our partner doesn’t know about.

My own secret is my obsession with lingerie, especially wearing it! Since I first tried on a pair of tights in my teens, stolen from the laundry basket, I’ve loved the feel of dressing up in sexy, delicate, feminine underwear. Over the last fifteen years I’ve tried so many styles, and built up a small collection of my own, well hidden from my unsuspecting wife. Over time I have figured out what sizes fit me, the styles and colours that I love to wear, and which items make me look like the girl I want to be. From a cute innocent teen, to a filthy slut who would do anything you ask, I have the right lingerie for the right occasion.

Now that my wife had gone away for the week, it was time to let Sophie, the girl I want to be, come out to play……. And boy, did she have some exciting plans for this week! My first port of call was to log on and check my e-mails. There waiting for me was the message I wanted to see…..

>> Hello Sophie,
>> Just want to check you are still able to meet up this evening.
>> I’ve booked us two rooms at the hotel as we planned.
>> Can’t wait to see you at 7pm
>> Andy xx

I fired off a quick reply to let him know that I was still ready to hook up, and very excited about meeting him tonight. I had met Andy on a crossdressing chat site, and we had really hit it off. He seemed very kind and caring, and really showed an interest in chatting and actually getting to know me a bit. He was also very understanding of my situation – the fact that I was married, and the fact that I had never met with anyone before. And best of all, (as well as being gorgeous!) he was fairly local to me! Before long, we had exchanged photos, and made plans to try and meet up when my wife went away. Finally, that time had arrived.

I had spent the whole of last week running through in my head how the evening might go. Various scenarios, good or bad, that may happen. Imagining in my head ways to back out if I didn’t feel happy to go through with it. Lots of thinking ”What if…”, ”What if…”, ”What if…”. I had already made a mental list of everything I needed to pack to take with me, and within 30 minutes I was putting a small suitcase in the car.

Part 2; The Hotel

I pulled into the car park of a country house hotel on the edge of town. As I parked I realised I couldn’t remember any of the last hour of driving. My mind had been elsewhere the whole way, still playing out different events that could happen. I walked into reception where I was greeted by a very friendly receptionist

”Good afternoon. I believe a room has been booked for me? It should be under the name of Jackson”.

The receptionist tapped away at her keyboard. The longer it went on, the more I started to fear the worst, and expected to be told there was no reservation. To find out that I had been stood up. That Andy was just leading me on and had no intention of ever meeting me…..

”Ah yes…. Here we are Mr Jackson. You have been booked into the Regal Suite. There is a wonderful view across the gardens from there. You certainly picked a good one! Follow me, and I’ll show you the way”.

We reached the third floor, and headed for a grand oak door. As the receptionist swung the door open, I was awestruck by the sight in front of me. My mouth just dropped open as I took in the sight in front of me. The room was huge, with a small sofa and chairs in one corner. There were huge floor to ceiling windows letting the sunlight stream in. Against one wall was a dressing table with an ornate mirror, but the centrepiece was on the other side of the room. Dominating the room was a grand oak four poster bed covered with luxurious looking pillows and covers. This certainly wasn’t the grotty little motel room that was a possibility in one of my thoughts!

The receptionist obviously gauged my reaction well.

”You like the room Mr Jackson?” she asked, with a smile on her face. ”The bathroom is through that door. If you need anything, just use the phone to call us on reception and we’ll do all we can to help. Room service is available 24/7. Enjoy your stay with us”. And with that she turned and left me alone to fully explore the room.

I threw my suitcase onto the bed and checked the time….. I had 4 hours to get myself ready and complete my transformation into Sophie. Soon I was stepping into the shower, and feeling the warm water rush over my body, letting my mind drift away, and for my thoughts to become those of Sophie. For the first time in my life I used hair removal cream on my legs, and watched with a smile on my face as the hair fell away, to leave two smooth shapely legs, glistening in the flowing water. I couldn’t stop myself from running my hands up and down them, marveling at how smooth and feminine they felt. One small action and I already felt well on my way to becoming a new person. Before I knew it, I was liberally applying the cream to my crotch and ass. My cock was getting harder and harder as my fingers worked the cream over my balls and around my hole. I couldn’t hold back from wrapping my hand around my little 5inch cock and slowly wanking while i eased a finger into my ass, already lubricated from the liberal amount of cream i had covered myself with.

As I pulled back on my cock, I slipped deeper into the mind of Sophie. In my imagination I was a gorgeous brunette, sharing a shower with my first lover and feeling a cock get hard with my touch. My lovers hands were all over my smooth, girly body. His fingers exploring my virgin hole. Without realising, I started to let out small, high pitched moans, as my imagined lover started bringing me closer to orgasm. My body was opening up for him, allowing him to slip a second, then a third finger inside me. It felt so good to have his fingers inside me, pushing deeper and deeper into me. My mind was picturing how turned on he was as I could feel the cock getting harder and harder in my hands. I could feel the precum as my fingers slid over his engorged head, teasing him and taking him closer to the edge. As I felt my orgasm build, I knew he was just as close to cumming as I was. My moans got louder and more intense. My body started to tense up as a wave of pleasure shot through my body. My ass tightened around the fingers inside as my orgasm pulsed through my body. I could feel his cock twitch as cum started slipping through my fingers which I greedily brought to my mouth to lick clean and savour the taste of my man.

As the water continued to flow over me, I was slowly brought back to reality. My fingers came out of my ass, leaving me feeling empty, but very ready for spending the evening with Andy! I felt content and relaxed, finishing my shower with a post-orgasmic smile on my face, as I eagerly anticipated what the rest of tonight would have in store.

With my body smooth and hairless, I stepped out of the shower and rubbed a tanning body lotion all over myself, making my skin soft with a subtle tanned shade, and leaving a delicate feminine fragrance on my body. I wrapped myself in a large white towel, enjoying how the material felt against my skin and headed back into the room. I sat on the edge of the bed and painted my toenails a gorgeous shad of red, before the time came to slip into a little something sexy to make me irresistible to my man when he arrives!

Opening the suitcase, the first item I took out was my basque – a beautiful lacy black and and powder blue number. I wrapped it around my body and pulled the eyelets together, loving how it pulled tight against my body. With the last hook in place, I spun it round and slip the straps over my shoulders. Already, my body was becoming more curvy…. A look which was completed as I slipped my new breastforms into the basque. They gave me a realistic looking 34B chest, and felt like real tits through the fabric of the basque, including realistic nipples for my man to play with!

Next up, I opened up a pair of brand new black, seamed stockings. I picked up the first one and took my time to bunch it up, before daintily pointing my foot foward, and slowly rolling the nylon up my smooth leg. I usually had hair on my legs when dressing, so was amazed at how easily they slid up my leg this time…… And the feel of the stocking against my smooth soft skin was just magical! With the elastic top around my thigh, and some straightening out of the seam, I was ready to attach the clips from my basque and pull all four nice and tight, and repeat the process with the other leg.

Finally, I stepped into my matching black lace, and powder blue knickers, bending over at the waist and sticking my ass out as I reached down to pull them up my legs. With a little wiggle, I pulled them up and felt them hug my bum. Was strange to have the knickers over my suspenders, but hopefully this would give Andy easy access while I kept my stockings on!

With all my lingerie on, I took a moment to see how I looked in the mirror…. without wanting to sound too big headed, I was looking pretty fuckable! The basque was giving me curves in all the right places. There was the sexy flash of flesh at the top of my thigh, and the stockings were making my legs look very very shapely, with just a glimpse of my red nail polish showing through on my toes. From the neck down, I was looking like a stunning woman dressed in her very sexiest lingerie….. all apart from the slight bulge in the front of her knickers!

I then slipped into a plain black skirt, that was nice and tight around my bum, showing off my curves, and fell to nearly mid thigh. Enough to keep my stocking tops covered, unless I ”accidently” bend over and give a flash of my suspenders, and bare thighs! I matched the skirt up with a flimsy, light blue halter top, a similar colour to the lingerie underneath.

I moved to sit at the dresser, subconsciously crossing my legs as I sat like a good, classy girl does! I applied some foundation, then a little blusher on my cheeks. I managed to keep my hand steady as I applied some mascara and a little bit of eyeliner to my eyes, and some shodow on the eyelids. My eyes were now looking deliciously smokey and very inviting! Finally, I puckered up and covered my lips in a little red lipstick….. not too much so as to look slutty, but enough to entice Andy to come in for a kiss…. hopefully! I didn’t have much experience of putting on make up, but (with a little help from tutorials on youtube) I think I had done a pretty good job. Enough to look girly, just on the verge of slutty, but not over the top.

The final piece to complete the look, was by latest, most extravagant purchase….. A brunette wig… shoulder length with a slight wave, and made of real hair. As I placed it onto my head, and made some small adjustments, I felt my transformation was just about complete. A quick look at the time, and I had just a few minutes to spare. I slipped on my four inch heels, and walked over to the sofa. I had a quick look in the full length mirror and was amazed with what I saw…. there was a gorgeous woman staring back at me rather that the guy I usually saw in my reflection! Pleased with my efforts, I sat down and waited, with butterflies in my stomach, for Andy to arrive……

Part 3; A Knock At The Door

After what felt like hours (but was in fact only a few minutes), there was a gentle knock on the suite’s door. I stood, and slowly walked across the room using this last chance to practice my sexy, seductive walk in my heels. My mind was racing, thinking about what was about to happen. I got to the door and took a deep breath to help steady my nerves. “This is it. No turning back now” I quietly said to myself, as I reached forward to open the door and allow myself to enter a new chapter in my life.

The door swung open, and there he was…. the guy who had been all I could think about for the last week. The guy who came into my mind as I screwed my wife before she went away. The guy I wanted to give my love and body to.

My goodness…. he was more gorgeous in person than his picture had suggested. He was dressed smart, but not too smart in black trousers and a white and blue shirt. You could make out a hint of a toned body (not gym-obsessed-beefcake type….. just enough definition to show he took care of himself!).

In that moment of admiring who was stood in front of me, I saw his eyes look me up and down. The the way his smile grew gave me the idea that he liked what he saw, and I’m sure I felt myself blush a little. In one hand he held an ice-bucket complete with a bottle of champagne, two champagne flutes and a single red rose. His free hand reached forward to take mine.

“Good evening Sophie. You are looking incredible”

He brought my hand to his face, and kissed the back of it

“I’m so glad we finally get a chance to meet. Since the first time we spoke online, I’ve been dreaming about this day” Andy said.

I could feel my heart beating faster and my head started to get lighter…

“It’s very nice to meet you too Andy. Please…. come in. This room is amazing. You sure know how to pick a good hotel!”

“I’d heard good things about this place. Just wanted to make your visit special. Why don’t you take a seat, and I’ll open this for us”.

I smiled, turned, and walked over to the sofa. I caught a glimpse of him in the mirror, and I’m sure he was watching as I walked away, so made sure I swayed my hips and bum a little as I moved across the room. It felt so good thinking of him staring at my ass and enjoying the view!

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Time flew by, as we sat on the sofa and chatted about everything and nothing. Andy was full of interesting tales, told with passion and humour, but also gave me time and space to talk to, and appeared genuinely interested in what I was saying. He was putting me so at ease that, combined with half a bottle of champagne, I didn’t realise how close we were now sitting, and how as I was telling a particularly animated story, my hand had ended up on his knee, and our faces were only inches apart. The story ended, and we just sat looking into each others eyes, his arm was slung across the back of the sofa, his fingers resting gently on my shoulder. I could smell the musk of his aftershave, and hear his breathing and without even being concious of it, I leant in to kiss him.

Our lips met in a gentle embrace, both of us opening our mouths slightly, allowing our tongues to meet and dance together. Something felt different, and it took me a moment to realise – It was his stubble! Although being clean shaved, I could still feel a slight roughness to his face – a sensation I had never experienced before, and in that moment I felt more feminine than I ever had before.

As we kissed, I felt his fingers move from my shoulder, and start slowly brushing up my neck, and behind my ear. I melted into him, and my hand started moving from his knee, and running up his thigh. My fingers traced up his leg, reaching closer and closer to his crotch. The kiss was becoming more passionate, and I could feel him pulling my head in towards his.

Finally my hand reached it’s destination, and I began to rub his bulging crotch through his trousers. I don’t know if he was getting hard yet, as this was all so new to me, but through the fabric of his trousers he already felt so big. I’m sure I could make out the outline of his cock, and it was definately twitching as fingers run across it.

Suddenly Andy broke off from our kiss.

“Sophie…… We don’t have to do anything if you don’t want to. I know this is your first time, and I don’t want you to feel any pressure to do something if you don’t want to do it”

But it was too late. My mind was made up. I shifted myself, to put me knees on the sofa, straddling his lap

“I’ve never wanted something so much before, Andy” I told him, then moved forward to resume our kiss, only this time with more vigour, and inflamed with passion and desire. My hands were round his face, pulling him in close to me, and he reached his arms out to my hips and held me tight.

My fingers moved down, and fumbled with the buttons of his shirt. I wanted to get my hands in there and caress his chest – to run my fingers through the hair and feel his firm pecs. Soon my mouth was heading the same direction, planting kisses down his neck and running my tongue over his nipple.

I slid down onto the floor, so I was now kneeling in front of him, looking up into his eyes, as I started to undo his belt and trousers. I was filled with lust, and couldn’t wait to see what was waiting inside. As soon as the button was loose, I pulled his trousers and boxer shorts down, as gazed in amazement at the delightful cock that was now in front of me. I knelt and stared for a few seconds, and without even realising was licking my lips. Andy sat back, his arms outstretched and shirt undone and asked

“You like what you see?”

I couldn’t find the words, so just nodded, while seductively biting my lip, and looking up into his dark eyes. I reached my hand forward, and ran my fingers up and down his semi-erect cock. It looked to be about 8inches long, a bit thicker than mine, with a delicious looking, glistening head. I could feel it and see it twitch as my fingers touched it, just feeling the warmth and texture of my first cock. I wrapped my fingers around it and began to move up and down – just a little at first, and very slowly. Already Andy was sighing and for the first time I was experiencing the sensation of another guys cock getting harder and harder in my hand. Knowing the effect I was having on him made me feel like such a slut!

It didn’t take long for him to become fully hard in my hand, and the head was now glistening a little with precum. I couldn’t resist moving my head forward, and running my tongue from the base of his cock, slowly slowly up the underside, to the head, before swirling my tongue over his bulbous, sticky bellend. Good God, that tasted delicious! I had tasted my own cum before, but Andy’s was something else. Warm, sticky, and slightly salty. It tasted of man! I couldn’t hold back from trying again, and repeated the process, running my tongue up his cock, feeling every bump and ridge, before slurping my tobgue over the sweet spot. I was like a little girl with a lollipop!

After a few licks, I decided to go a little further…. As I reached the head, rather than just lick, I opened my mouth and wrapped my lips around his bellend, and gently sucked. Each time doing this, I would take a little bit more in my mouth, and suck for just a little bit longer. Soon I was slipping a good couple of inches into my mouth, being careful not to catch him with my teeth. Eventually, I just held my mouth there, holding the base. I managed to look up into his eyes again, his face filled with pleasure, and slowly slid my mouth further and further down his cock, taking him deeper into my mouth.

I took him as deep as I could go, and kept my hand wrapped around the base, enveloping his whole length. It felt amazing to have my mouth stuffed with Andy’s warm, delicious cock. My lips could feel every ridge and bump as they slid slowly back up to the head to taste more of his precum. My tongue danced and swirled across the end of his meat before sliding back down again. I slowly picked up my pace, and could hear Andy’s breathing get heavier as he got more and more aroused. My free hand reached between his legs, and I started to play with his balls. They felt so heavy in my hand, as I lifted them and squeezed them while sucking and slurping on his cock.

Andy’s hands were now on my head, his fingers running through my hair. He was bucking his hips in time with my movements. It felt so good to have him slowly fucking my face. I was embracing my role as a hungry cockslut, eager to please her man. I decided to bring him even closer to the edge, and started humming as I broke my blowjob cherry. The humming seemed to have the desired effect, as his breathing becoming grunting and moaning. It wasn’t long until I heard him groan…

“Oh baby…. that feels sooooo goood…. I think I’m gonna cum soon….”

I released him from my mouth just long enough to tell him “Cum in my mouth hun”, before clampiing my lips back round him. After a few more thrusts, I felt his cock start twitching and jumping like crazy, before erupting inside my mouth. I sucked hard as four jets of cum shot into my throat, and swallowed them down greedily. As his orgasm passed, I continued to lick his cock clean, this time holding the cum in my mouth as his cock softened.

I released him from my oral grasp, and crawled back onto the sofa with him. I opened my mouth so he could see the wad of cum still on my tongue, before swallowing it down in front of him, and smiling.

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