Kyle - Martini Date

Hi, I am Leigh, a Crossdresser (CD), Caucasian, 68" tall, women's size 8 or 10 depending on the brand, green eyes, and shoulder length hair. I have always had soft facial features. My stories are more of a diary entry than a novel. They actually happened but I changed the places and names.

Kyle, my unofficial boyfriend has invited me out to have dinner and drinks with a couple from his gym. This is all part of Kyle's plan to get me to stay dressed full time, something I think I would want, but I still have my reservations. Because I have not had many safe opportunities to go out dressed, I accepted Kyle's invitation.

I wanted to dress a little conservative and make a good impression on Kyle's friends so, I picked out a plaid skew neck handkerchief dress. The top of the dress was black and the bottom was black and green plaid. I picked out a pair of black suede ankle strap 3.5" heels and skin tone opaque thigh high nylons. I also decided to wear the earrings Kyle bought me, they were heavier than I have ever worn but they made me feel extra sexy when they swung while I walked. I transferred all my essentials to a small green plaid purse with a thin chain. I bought a professionally fitted and trimmed wig to match a hairstyle and color Kyle pointed out from a magazine. It was dark brown with chestnut highlights in a "Rachel" trim. How I got a $500 wig and trim for $50 is going to be another story.

I recently traded in my car for a Jeep, 6-speed. A manual transmission is nothing new for me but driving in super cute dress pumps with a 4-inch heels and a black bow on the back is something I had not thought completely through. My feet fit ok on the clutch and the accelerator this will just take a little practice to make it feel comfortable, I thought. It was a quick trip down the expressway to Kyle's exit but the wipers were barely keeping up with the rain and it was the end of the workday so traffic was picking up.

I quickly learned another flaw with owning a jeep: the guys were checking out the Jeep then they caught a glimpse of a gurl driving a Jeep and they needed to take a second, and often closer look at the driver. This was making me self-concise and a little worried, not everyone is nice, there could be that one guy out here that wants to beat the shit out of a tranny. I became thankful that the steady rain was helping with the illusion that I was a regular girl and not a crossdresser. The exit took me down a marginal road along the south side of the expressway heading east. I needed to be in the number 2 out of four lanes to make the left turn, go under the expressway, and then turn right to get onto the north marginal road to continue east to Kyle's apartment building. This put me right in the middle of all the cars waiting for the various lights and mine was a left turn so I had the longest wait. I was sure any second now a grizzled mountain of a man from a biker gang would pull me out of my Jeep and beat the shit out of me. In just that moment, it became noticeable that the shoulder belt was uncomfortably pulling on my water bra. In that 30-senconds of adjustment, I became aware that I was fulfilling the ultimate traffic fantasy for the construction workers in the truck next to me.

I made the right then the left and in just a mile or so pulled into Kyle's apartment complex, safe and sound. I sat in my jeep for a little bit, to make sure the path from here to the front door of the building was clear, I did not want to meet any of Kyle's neighbors this way so I waited in my jeep to see who was coming and going.

Satisfied, I headed to the door with purse in hand and just as I got to the door two teen-aged males came out of the building, surprisingly one of them held the door for me, and the other male stepped down onto the grass so I could use the sidewalk. I was sure I was going to get a comment from one of them as I got closer but all one of them said was "good evening" and I think they may have been checking me out.

I took the 3-4 steps down to Kyle's "garden level" apartment that was one fourth of the building's basement. It was if Kyle was waiting behind the door when I knocked. He invited me in, pulled me into his arms, I inhaled deeply and my nose filled with his familiar scent, pine needles, the forest right after a rain passed, and then Kyle kissed me ever so gently. "Mmm" was the only thing that escaped me, and I realized my eyes were still closed.

Kyle was still holding me while and studying my face when I opened my eyes, he broke into a smile and asked if I fell asleep there in the moment. I was just very content where I was right there and then but what came out of my mouth was, "am I forgiven?"

Kyle placed his hand under my chin and made me look at him. His bright blue eyes seem to have a light of their own, but my attention drifted to his lips, waiting for them to speak, and then back to his eyes. "Of course you are" Kyle whispered as he pulled me closer for another kiss. A kiss that was so intoxicating my brain could not handle thinking about anything else, as his mouth moved against mine all the worries and anxieties of the world faded into a kind of numbness.

"You are forgiven if you tell me all about you and your Aunt's contractor." Kyle playfully said between kisses.

"Maybe I'll show you later, I did bring my overnight bag." I responded.

"Oh and concerning our talk last week I came to a decision. "I said as I brushed my hair back to show Kyle my vixen drop earrings sporting turquoise and diamond birthstones.

I would have been content to stay here and spend the evening alone with Kyle but if we were going to meet up with his friends, we needed to head out. Kyle was driving and that means I can drink all I want tonight and Kyle will insist on paying for everything tonight. Well I will have to give something up tonight, if everything goes well, ha.

Kyle was a perfect gentleman, walking me to the car with his arm around me. Honestly, it was difficult to relax and let a man put his arm around me, I wanted it, but it was still something I had to let happen. "Just let things happen and be part of the moment." I thought to myself.

Besides his motorcycle Kyle had a black, little two-door car with a back seat; I smoothed the back of my skirt as I slid into the passenger side letting Kyle close my door. As the manager of a Fitness center Kyle gets to work out almost 6-hours a day and it was obvious watching his body walk around to the driver's side of the car.

Pulling out onto the expressway, the rain had given way to a steady mist. Kyle had assured me his friends were completely comfortable in meeting a CD.

"What were your friends' names?" I asked.

"Neil and Monica." Kyle replied without taking his eyes off the road.

"What does he do for a living?" I asked.

"Neil is a funeral director." Kyle answered as he maneuvered the car onto the downtown exit.

"It's funny how many Monica's I run into, matter of fact I work with a Monica." I confessed. "Is she a genetic girl (gg)?" I asked.

"Nothing to worry about, this Monica is a college student and yes she is a gg." Kyle answered as we drove under the giant chandelier that silently announced our arrival in the theater district.

Kyle maneuvered the car into the parking lot and after finding a spot, the parking lot attendant approached us. He was a black man, very tall and slim and seemed to be in his late 60's. He was very well dressed with a white shirt and a black vest with a red bowtie and a conductor style hat. I crossed around the back of the car while Kyle was paying the attendant. As I approached, the attendant removed his hat before addressing me, wishing us both a pleasant evening.

Kyle leaned down, kissed me, and smiled as we began walking towards the Martini Bar. This was going to be a night to remember, I was so immersed in the date I honestly forgot I was dressed like a woman and did not care if anyone said anything derogatory about me, I was very content in this lifestyle and wished I could make a complete transformation. I let my mind wander as we walked. Kyle is a very "Alpha Male", and that is exactly what I want from him now but could I date him full time? Alpha males are so nice to be around since I understood exactly what was expected of me and I was more than happy to accommodate those wishes, part time.

The Theater District was very clean and well patrolled by police, two police officers on horseback passed us as we walked. The city also had uniformed ambassadors patrolling the Theater district in bright yellow and blue jackets on bicycle you could stop and ask for assistance. This was the safest section of downtown.

The Martini Bar entrance just around the corner from the main entrance of the 1921 theater building and there was a gentleman in a tuxedo and top hat with two women dressed as 1920's flappers who offered to take our picture in front of a large poster advertising the Broadway play RENT. We got two pictures one with Kyle and me and one with just me holding a sign that read: "Take me out tonight."

We entered the door to the Martini Bar and immediately walked down a flight of marble stairs to a beautiful 1920's art deco marble bar with sculpted brass accents and statues of women at each end, possibly the goddess Nike, holding a milk white globe light at each end of the beautifully stocked bar. In the middle, there were two large containers of frozen margarita, one the traditional lime green and one appeared to be strawberry red.

"It makes you wonder if they actually use the bottles at the top of the bar." I said to Kyle, but the bartender heard me.

"They are used as re-stock; I do keep the top shelf handy down here, what can I get you miss?" the bartender asked. She was talking to me but her eyes were looking Kyle up and down and by her Cheshire cat grin, she liked what she was looking at. She was cute, maybe in her mid-twenties very short bleached white hair and her super tight jeans with the belt loop hem cut off. Oh and excessive piercings. Her nametag said Brenda.

I asked for a frozen strawberry margarita and Kyle asked for a coke with a lime twist. Brenda made our drinks and climbed on top of the bar kneeling in front of us in her best SI pose to pin a designated driver badge onto the lapel of Kyle's jacket, her hand was taking liberties of Kyle's chest. I thought was a little excessive with me standing right there.

In a booth near the back we found Neil sitting alone, his date was in the Ladies Room. Kyle offered me to slide in to the booth first, fine with me; Kyle can be my buffer from the real world. Neil was nice and he still had his Scottish accent, a definite turn on for anyone that could hear him talk.

Kyle and I were facing away from the restrooms so we did not see her until it was too late. Monica slid into the booth next to Neil and I froze, I was so scared I could not move; it was she. It took her a moment; you could see here brain making the calculations, her eyes jumping around taking in different aspects of my face, then her eyes went wide and he mouth dropped open. Yes, she was the Monica I worked with. My real life and my transgender life just merged.

Kyle sensed my distress and put a reassuring hand on my thigh. The only thing that I could do was say:

"HI"

"Oh my gosh, I knew something was up, I mean to each his own, but, wow," Monica said.

I reached for my drink, hands shaking, I hand to use two hands to take a drink, and I wish it were stronger.

"Kyle, this is Monica, I work with her," I said.

Monica was energetic, hyperactive, and obsessive-compulsive. Sometimes she can be overbearing and domineering; but, she can also be the levelheaded practical friend at work, but I am not sure, how that is going to play out tonight finding me dressed like a girl. Tonight Monica had her hair in a bob cut that just brushed her shoulder and it had a lot of volume.

"I really like your hair," I said to Monica.

Monica reached over and playfully felt the tip of my wig, complementing me on mine. After a moment of awkward silence Kyle offered to refresh our drinks and Monica nudged Neil he should go help. As soon as the guys were out of earshot...

"I'm very impressed, I thought you were a freaking hermit, now look at you, you are like on the opposite side of the spectrum, I'm very impressed!" Monica said.

"I am? I mean what are you going to tell everyone at work?" I asked.

"I don't think you're a freak, and I'm not going to say anything, like I said before: to each their own. Nevertheless, seriously how did you and Kyle get together? I mean, he is a real hunk and you don't take this the wrong way, but you are not in his league, or so I thought." Monica said.

"Monica, honestly I'm trying to figure out who I am and Kyle is helping me out and we are not exclusive, maybe I could put a good word in for you if you like. "I said as the guys returned with our drinks.

We chatted for a little while before Kyle leaned in, kissed me on my forehead, and asked if I was doing ok. I assured him I was doing great, and I was having a great time, thanking him for taking me out tonight. Monica gave us the surprised look with a bit of jealousy mixed in. They say all women gravitate towards a certain type of man, some like the executive, some like the construction worker; Monica liked guys who worked out, loved the outdoors, had an accent, and was man enough to fill out a pair of spandex shorts. Kyle was all those things and from the Netherlands.

I asked to be excused, to go to the bathroom; Monica got up to go with me. I guess I surprised her once again by my boldness of walking right into the ladies room. Once inside we went in our stalls took care of business then to the mirror to touch up our makeup and hair.

"So have you and Kyle had sex, yet?" Monica asked.

"Oh yea, and it's great." I answered.

"So what have you guys done?" Monica asked.

"Everything, oral, anal, making out, everything a normal couple would do. Tonight is the first time I'm spending the whole weekend at his apartment." I explained.

"How big is he?" Monica asked.

"What do you mean, how big is his cock? It's almost 12", thick, and uncut." I answered.

"How do you fit that inside of you?" Monica asked. Our conversation was cut short as other women entered the restroom; we finished up and as we headed back to our table Monica whispered we needed a girls day to chat and get caught up.

"Let's stop at the bar and get another round." I offered. I ordered one of everything I knew our table had been drinking and Monica surprised me by ordering four smoky whiskey and two tequila shots.

"If I didn't know any better I would think you are trying to get me drunk Monica." I said.

"No not you but maybe I can get Neil to pass out and arm wrestles you for a chance at Kyle." Monica replied.

"That would be easy to arrange, Kyle and I are part of the Stag & Vixen lifestyle now, so anything is possible." I said.

We collected our drinks and as we walked down the bar to our table, Brenda, the bartender caught me at the end of the bar and gave me her number; she said she would like to have a turn with Kyle if possible. She did not care it might be a threesome. I found the idea of sharing a bed with Brenda and Kyle an interesting proposition.

We took the drinks back to the table, and we continued to have a good time, I was getting drunk and maybe that is why I started teasing Kyle under the table. At first it was just my hand on his thigh but it progressed to my fingers mindlessly fluttering around on his crotch while the four of us chatted and drank. My finger flirtations elevated to the tips of my fingers tacking the outline of Kyle's cock in his thin dress pants. As soon as Kyle had readjusted himself for the third time, I offered that we go to a different club, somewhere with music.

We paid for our drinks and I relinquished my cell number to Brenda who reminded me she was serious about a threesome with us. Not only did Brenda comp my drinks she kissed me on the cheek and referred to me as sister. I gave her a cheeky smile and the four of us headed outside.

Neil and Monica parked in the lot on the northeast side of the building and we had parked across the street from the southeast corner of the building. We chatted, confirmed where we were going, and went our separate ways. I quickly realized just how drunk I was, and I thought walking in heels sober was challenging. Kyle had almost carried me back to the car. We passed another couple and I overheard the women tell her date "that guy is getting lucky tonight." Little did she know, well she should have had an idea right? She is a woman; yes, she knew what I had planned, I am sure of it.

I stumbled across the street to the parking lot apologizing to Kyle the whole way for being a drunk klutz on heels and for teasing him in the club as I did.

Kyle just said, "Don't worry about it, its fine, that's why I'm here, no problem."

When he guided me through the passenger side door I said, "I'm so sorry, get in so I can suck your cock in the parking lot, just to say I'm sorry." I said.

I was starting to sober up a little but I wondered why the car did not start moving, Kyle adjusted his seat and was pulling his pants down for some unknown reason, then I remembered I had just promised him a blowjob two minutes ago. I was this old, when I realized park on the center-console shifter was all the way forward so I could lean over to give Kyle head.

With my knees on the passenger seat, I leaned over, pulled his foreskin back on his uncut cock, and started licking up and down and around his cock with my tongue before pursing my lips and sucking his cock into my mouth.

"Fuck, you have perfect lips for this, baby." I heard Kyle exclaimed as I used my hand and mouth together.

Kyle tried to play with my ass but I was not messing around, we did not have all day to get him off. I was pumping my mouth up and down the first 4-5 inches of his cock like a machine. This enthusiastic rhythm caused Kyle to remove his hand from my ass and place it on the back of my head. I was getting excited; with my head in Kyle's lap, all I could see was the floor mat, the steering wheel, and his cock with my lips sliding up and down.

"Keep, yes, keep sucking, baby, that's my pretty little vixen, suck that cock." Kyle said.

I knew I was taking his cock the right way because I had only had him in my mouth for three minutes or so and he was harder than rock hard already and his hips were trying to slip more of his cock past my lips. My complaints sounded like a long moan and that just spurred Kyle on to push me down harder while his hips lifted off the seat. I heard, "oh shit." and Kyle froze and I felt his cock pulse in my mouth, his hand on the back of my head held me still as his cock began to throb. He shot a decent load into my mouth, enough that I had to swallow a couple times. He must have been holding his breath when he came because after his cock stopped filling my mouth with cum I heard him gasp. I waited for him to begin to soften before I let him slip from my lips, we did not need a mess on our clothes.

"Wow, someone has been a good boy for a couple of weeks." I said.

"What makes you say that?" Kyle asked as he pulled his pants up and adjusted his seat.

"You came so much I'm almost sober again." I said.

Kyle pulled the car out and headed down the street. I looks like that was only a five-minute blowjob, too bad, they normally last 20-30 minutes with Kyle. I pulled the visor down and fixed my makeup in the lighted mirror. In about 10 minutes, we pulled into the valet parking outside of the club. A neon sign with a giant animated tongue and martini glass illuminated the entrance to the club. Neil and Monice were waiting for us at the valet stand.