Night of Many Firsts
- 2 years ago
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A Night Of Firsts Pt 1 free porn video
'Oh my God, this was the night,' I thought to myself. 'I'm finally going to go out dressed.'
I work for a small company and get to travel a bit, but I've really only dressed in hotels when I could drive as flying with all my things makes me really nervous. The idea of me and a travel bag being examined and having a stranger discover my femme things just didn't do it for me.
However, this time was different. As I only was going three hours away and staying in a larger city, I had access to a company car. Therefore, I would be taking my goodies to be able to dress. I also had scouted out a club very close to the hotel I was staying. I was going to dress as Pam and go to a club that night featuring a CD themed night with dancing, karaoke and would be welcoming for me to show up fully en femme.
About me- 29, swm, 5'9'', about 150 ish, long brownish auburn hair which I kept in a pony tail as I usually wore a hat over it anyway. I kept my body shaved smooth all over and was proud of my slim figure, and without sounding too cocky I think my flat tummy, long legs and bottom looked good. My ass was just curvy and firm enough to look good in what I wore without being a flat 'no ass' or flabby monstrosity. As I had been dressing since about twenty-one I had perfected a nice look that I considered more than passable. I had taken some pics of myself dressed and didn't mind the look, but living in a smaller town I had yet to ever go out dressed or meet anyone who might appreciate that. So I dressed alone.
I had arrived at the hotel mid-afternoon with plenty of time to prepare, but not driving like a maniac to get there. Once checked in, I stashed all my femme clothing and found a hairdresser nearby. I planned to lop off a few inches of hair in order to have a really femme 'do' for hitting the club, then return to the same place the next day to cut the rest of in order to show up the following Monday at work with a normal haircut so I could say "surprise!" to all the coworkers who had never seen me with short hair.
The hairdresser was a brunette, maybe fifty I guessed, and a taller woman with a nice bosom and fuller womanly hips. She was attractive in that way you might secretly find a girlfriend's mother or an office manager to be attractive yet a bit imposing at the same time. I decided to leave one side longer hiding my face hanging over my eye and the other shorter almost like a page haircut. When my slightly curly longer hair was trimmed to look this way, the curls tightened up slightly which I found to be very sexy when she spun me around to take a look when she was finished.
"That looks really good on you- mysterious. Almost like a man vixen" she said into my ear while blowing the remaining hair a bit with a dryer to make it poof out a bit for having more body.
"Huh? Oh, thanks, it'll be a lot cooler for the rest of the summer," I replied, inwardly thinking 'if only she knew'. I gave her a generous tip and on the way out she told me "Come back any time!"
Baseball hat on my head to cover it up, it simply looked like I was just growing my hair out.
Returning to my hotel room, I laid out everything I would wear that night. I had a few hours until the club would open for the event, so I ate some sandwiches out of a cooler I brought, watched some TV, diddled on my laptop for work related stuff and tried to calm the butterflies in my stomach.
6 o'clock, 7, 8, 9 o'clock. Then the preparations began. This is usually the part where gurls like me go through an entire list of how they prepare for an outing, down to the brand of skin care and makeup they use. To save strain on the eyes, I'll summarize- a shower, shaving myself extra smooth all over, checking myself in the mirror, pouring myself a drink in just a towel, savoring the delicious anticipation of Pam's first night out.
As I had actually thought ahead about this whole trip, I had purchased a tiny clutch-like purse to throw some items into. I giggled thinking how many pockets in men's pants there are, and if I had to carry everything I carried as a man, wallet, keys, change, phone, a tiny leatherman like tool, etc I'd be sunk as Pam.
Oh, I almost forgot- my outfit!
A tight, short and clingy lycra blend black dress, spaghetti straps, cut-away to show plenty of shoulders and upper chest but not too low cut. It came down maybe only a few inches below my bottom and oh my God it felt so good hugging me. It looked like a cross between a clingy foundation garment and a little black dress for how closely the lycra/spandex blend clung to me. To top it off, the dress had a 2-inch slit up the left side.
32C breast forms glued on, and a wireless sheer black bra kept them in place perfectly! A wide black velvet choker around my neck, black lycra blend gloves minus the glove part that extended over my elbows, a chain belt around my hips, some really expensive but soooooo glossy and sheer to waist jet black pantyhose (I tucked for hating panties with pantyhose for leaving a panty line, even thongs), 4 inch open toed black heels, a tiny gold chain worn around my left ankle over my pantyhose, a snake looking arm bracelet over my upper arm, a few bracelets from the thrift store bargain bin, small hoop clip on earrings-now for the makeup!
I had earlier painted both my finger and toenails a deep dark burgundy (almost like a dark plum shade) to match my lips. Smokey plum eye shadow, heavy eyeliner, a touch of rouge over the light foundation and feeling playful I took a sharpie marker and added a little Madonna/Marilyn Monroe beauty mark above the right side of my lips! I went rather heavy on the perfume, wrists, neck, the backs of my pantyhosed legs feeling increasingly more feminine and flirty.
Looking myself over in the mirror, I said to my reflection, "Pam, now you look like a real vixen, don't you?". I poured myself a smaller drink (no sense getting sloppy for driving) and as I sipped it I placed my phone, ID, hotel room key card, lipstick and some cash in my tiny clutch purse.
Anyone watching me practically sprint to my rental car parked near the side entrance of the hotel would have burst out laughing as I was doing it in heels, but I didn't see anyone else between closing my hotel room door and getting into my car. It was going 11:30pm and it seemed like a slow night for guests.
Suddenly, I started feeling nervous as it all hit me at once. I was completely en femme and I was about to drive to a club and go inside! 'What if I'm the only one dressed there?' Images of small town drunks chasing me out of the club down the street into a dark alley flooded my mind. I gripped the steering wheel of the rental car and breathed deeply for a few moments before starting it.
I had slipped my heels off before pulling out of the hotel parking lot and wore of all things some slippers I brought for this purpose as driving in heels right now would not be the best idea. Better to keep things simple I thought- don't take any chances, don't speed, don't hop the curb, don't run any stop signs.
The club was only about a mile away and thankfully easy to find. I saw what looked like a half full parking lot for the club and hoped there would be others like me there if nothing more than to take all the attention away.
As I switched off the engine, I suddenly became aware of how short and tight my dress really was as I noticed it had ridden up my thighs on the drive dangerously close to revealing that I was not a real woman. The harsh glare of the streetlights shimmered off my glossy black pantyhose as I switched the engine off. My hands shook a bit taking the key out of the ignition. Again I forced myself to breathe deeply and focus. I'm not doing anything wrong or illegal, right? Gurls go out all the time dressed and it is ok. It is ok. I touched up my lipstick in the rear view mirror and then gave myself a pep talk as I slipped my heels back on.
"You can do this Pam, this is what you've wanted to do for so very long. This is your night. Let Pam out to play and get her sexy gurl on!"
Smiling at my reflection, I opened the car door, swung my legs out carefully so as not to give anyone a little peek, stood, grabbed my purse, closed and locked the door and walked to the front entrance of the club.
The night was warm enough to wear something tiny and sexy like the dress I wore, but still with a hint of a cool breeze which felt exhilarating on my hosed legs, briefly even up my dress for all its clinginess. I heard myself softly gasp feeling the night air caressing my pantyhosed legs all the up to where they met.
Click, click click of my heels in time to my steps, focusing on putting one foot in front of the other so as to allow my hips to sway in a feminine fashion. I heard my nyloned thighs swishing together as it was that quiet outside for a Thursday night. I felt my heart doing laps around my chest. I felt like the only gurl who had ever decided to go to a club and told myself I was just being silly.
There was a line of maybe six people outside the club, and I exhaled in relief seeing a few other gurls like me waiting to get in. Some were passable like me, some not, but nobody seemed to care. A few men were also patiently waiting to show IDs to a doorman. I fumbled getting mine out of my purse and had to keep both legs together while half squatting, half bending to pick it up off the sidewalk. Yikes! My heart started to race.
The doorman examined my ID and smiled at me as he handed it back.
"First time here?" he asked.
"Yes, I heard it was a nice place," I answered in a feminine voice that I hoped would not betray me.
When the words left my lips, they didn't sound bad. In fact, they sounded quite natural.
"I hope you have a wonderful time here tonight, honey," he said as I placed my ID back in my purse and clicked up the steps to the club.
I took one last deep breath before opening the door...
I work for a small company and get to travel a bit, but I've really only dressed in hotels when I could drive as flying with all my things makes me really nervous. The idea of me and a travel bag being examined and having a stranger discover my femme things just didn't do it for me.
However, this time was different. As I only was going three hours away and staying in a larger city, I had access to a company car. Therefore, I would be taking my goodies to be able to dress. I also had scouted out a club very close to the hotel I was staying. I was going to dress as Pam and go to a club that night featuring a CD themed night with dancing, karaoke and would be welcoming for me to show up fully en femme.
About me- 29, swm, 5'9'', about 150 ish, long brownish auburn hair which I kept in a pony tail as I usually wore a hat over it anyway. I kept my body shaved smooth all over and was proud of my slim figure, and without sounding too cocky I think my flat tummy, long legs and bottom looked good. My ass was just curvy and firm enough to look good in what I wore without being a flat 'no ass' or flabby monstrosity. As I had been dressing since about twenty-one I had perfected a nice look that I considered more than passable. I had taken some pics of myself dressed and didn't mind the look, but living in a smaller town I had yet to ever go out dressed or meet anyone who might appreciate that. So I dressed alone.
I had arrived at the hotel mid-afternoon with plenty of time to prepare, but not driving like a maniac to get there. Once checked in, I stashed all my femme clothing and found a hairdresser nearby. I planned to lop off a few inches of hair in order to have a really femme 'do' for hitting the club, then return to the same place the next day to cut the rest of in order to show up the following Monday at work with a normal haircut so I could say "surprise!" to all the coworkers who had never seen me with short hair.
The hairdresser was a brunette, maybe fifty I guessed, and a taller woman with a nice bosom and fuller womanly hips. She was attractive in that way you might secretly find a girlfriend's mother or an office manager to be attractive yet a bit imposing at the same time. I decided to leave one side longer hiding my face hanging over my eye and the other shorter almost like a page haircut. When my slightly curly longer hair was trimmed to look this way, the curls tightened up slightly which I found to be very sexy when she spun me around to take a look when she was finished.
"That looks really good on you- mysterious. Almost like a man vixen" she said into my ear while blowing the remaining hair a bit with a dryer to make it poof out a bit for having more body.
"Huh? Oh, thanks, it'll be a lot cooler for the rest of the summer," I replied, inwardly thinking 'if only she knew'. I gave her a generous tip and on the way out she told me "Come back any time!"
Baseball hat on my head to cover it up, it simply looked like I was just growing my hair out.
Returning to my hotel room, I laid out everything I would wear that night. I had a few hours until the club would open for the event, so I ate some sandwiches out of a cooler I brought, watched some TV, diddled on my laptop for work related stuff and tried to calm the butterflies in my stomach.
6 o'clock, 7, 8, 9 o'clock. Then the preparations began. This is usually the part where gurls like me go through an entire list of how they prepare for an outing, down to the brand of skin care and makeup they use. To save strain on the eyes, I'll summarize- a shower, shaving myself extra smooth all over, checking myself in the mirror, pouring myself a drink in just a towel, savoring the delicious anticipation of Pam's first night out.
As I had actually thought ahead about this whole trip, I had purchased a tiny clutch-like purse to throw some items into. I giggled thinking how many pockets in men's pants there are, and if I had to carry everything I carried as a man, wallet, keys, change, phone, a tiny leatherman like tool, etc I'd be sunk as Pam.
Oh, I almost forgot- my outfit!
A tight, short and clingy lycra blend black dress, spaghetti straps, cut-away to show plenty of shoulders and upper chest but not too low cut. It came down maybe only a few inches below my bottom and oh my God it felt so good hugging me. It looked like a cross between a clingy foundation garment and a little black dress for how closely the lycra/spandex blend clung to me. To top it off, the dress had a 2-inch slit up the left side.
32C breast forms glued on, and a wireless sheer black bra kept them in place perfectly! A wide black velvet choker around my neck, black lycra blend gloves minus the glove part that extended over my elbows, a chain belt around my hips, some really expensive but soooooo glossy and sheer to waist jet black pantyhose (I tucked for hating panties with pantyhose for leaving a panty line, even thongs), 4 inch open toed black heels, a tiny gold chain worn around my left ankle over my pantyhose, a snake looking arm bracelet over my upper arm, a few bracelets from the thrift store bargain bin, small hoop clip on earrings-now for the makeup!
I had earlier painted both my finger and toenails a deep dark burgundy (almost like a dark plum shade) to match my lips. Smokey plum eye shadow, heavy eyeliner, a touch of rouge over the light foundation and feeling playful I took a sharpie marker and added a little Madonna/Marilyn Monroe beauty mark above the right side of my lips! I went rather heavy on the perfume, wrists, neck, the backs of my pantyhosed legs feeling increasingly more feminine and flirty.
Looking myself over in the mirror, I said to my reflection, "Pam, now you look like a real vixen, don't you?". I poured myself a smaller drink (no sense getting sloppy for driving) and as I sipped it I placed my phone, ID, hotel room key card, lipstick and some cash in my tiny clutch purse.
Anyone watching me practically sprint to my rental car parked near the side entrance of the hotel would have burst out laughing as I was doing it in heels, but I didn't see anyone else between closing my hotel room door and getting into my car. It was going 11:30pm and it seemed like a slow night for guests.
Suddenly, I started feeling nervous as it all hit me at once. I was completely en femme and I was about to drive to a club and go inside! 'What if I'm the only one dressed there?' Images of small town drunks chasing me out of the club down the street into a dark alley flooded my mind. I gripped the steering wheel of the rental car and breathed deeply for a few moments before starting it.
I had slipped my heels off before pulling out of the hotel parking lot and wore of all things some slippers I brought for this purpose as driving in heels right now would not be the best idea. Better to keep things simple I thought- don't take any chances, don't speed, don't hop the curb, don't run any stop signs.
The club was only about a mile away and thankfully easy to find. I saw what looked like a half full parking lot for the club and hoped there would be others like me there if nothing more than to take all the attention away.
As I switched off the engine, I suddenly became aware of how short and tight my dress really was as I noticed it had ridden up my thighs on the drive dangerously close to revealing that I was not a real woman. The harsh glare of the streetlights shimmered off my glossy black pantyhose as I switched the engine off. My hands shook a bit taking the key out of the ignition. Again I forced myself to breathe deeply and focus. I'm not doing anything wrong or illegal, right? Gurls go out all the time dressed and it is ok. It is ok. I touched up my lipstick in the rear view mirror and then gave myself a pep talk as I slipped my heels back on.
"You can do this Pam, this is what you've wanted to do for so very long. This is your night. Let Pam out to play and get her sexy gurl on!"
Smiling at my reflection, I opened the car door, swung my legs out carefully so as not to give anyone a little peek, stood, grabbed my purse, closed and locked the door and walked to the front entrance of the club.
The night was warm enough to wear something tiny and sexy like the dress I wore, but still with a hint of a cool breeze which felt exhilarating on my hosed legs, briefly even up my dress for all its clinginess. I heard myself softly gasp feeling the night air caressing my pantyhosed legs all the up to where they met.
Click, click click of my heels in time to my steps, focusing on putting one foot in front of the other so as to allow my hips to sway in a feminine fashion. I heard my nyloned thighs swishing together as it was that quiet outside for a Thursday night. I felt my heart doing laps around my chest. I felt like the only gurl who had ever decided to go to a club and told myself I was just being silly.
There was a line of maybe six people outside the club, and I exhaled in relief seeing a few other gurls like me waiting to get in. Some were passable like me, some not, but nobody seemed to care. A few men were also patiently waiting to show IDs to a doorman. I fumbled getting mine out of my purse and had to keep both legs together while half squatting, half bending to pick it up off the sidewalk. Yikes! My heart started to race.
The doorman examined my ID and smiled at me as he handed it back.
"First time here?" he asked.
"Yes, I heard it was a nice place," I answered in a feminine voice that I hoped would not betray me.
When the words left my lips, they didn't sound bad. In fact, they sounded quite natural.
"I hope you have a wonderful time here tonight, honey," he said as I placed my ID back in my purse and clicked up the steps to the club.
I took one last deep breath before opening the door...
Fay
- 22.09.2021
- 14
- 0
- Category:
- Crossdressing
