Colton Pt. 02 - First Date

My name is Leigh. Well my girl name, I am a cross-dresser. I just feel right to me and I guess that is how I am. All my stories are based on real experiences; but the places and names have been changed.

Do not ever expect anything. Expectations are a straight path to sorrow. Just have fun. ~Unknown

Most of the guys I have been with just wanted to fuck so just call me paranoid but when Colten turned down a drink after dropping me off at home from the party in Colten Part One. Seriously, any virgin would know I wanted the D when asked to come in for drinks.

As it happens, Colten, well Colt for short has been chatting me up on the phone almost every night since the party. As if he really wanted, a hook up, I mean the flirting was seriously off the hook. Finally, the stars and our schedules lined up with Colt asking me out on a date.

All week I had been trying to figure out what to wear, something a little girly but not too girly. Just in case the date ends with a "happy conclusion," I invested two hours in the bathroom getting ready, then another hour on makeup and hair. My nails were already polished, nothing fake this time.

I pulled out a black silky thong, one that held my boy parts tight and in check. I was not worried about a bulge, honestly, my bulge was not that big to start with, but the dress would conceal anything. Almost sheer nylons slid up my legs, and a water bra just to give me a little boost. The dress was a blue wrap with orchids printed randomly; the hem fell halfway to my knees. Lin caught me turning in the hallway in front of the long mirror.

"Looking good gurl." Lin teased, "What shoes did you pick out?"

"I bought new shoes, come, see what you think." I said.

Lin approved of the white heels with and ankle strap, with rhinestones dotted across the toes. Lin went in my closet and pulled out a white denim jacket with a hint of pink. The color was the result of a laundry room accident that turned out nicely.

Colt was picking me up; Lin and I were sitting in the kitchen when he pulled into the driveway. I got up and took my purse to the side door meeting Colt in the drive with a kiss. Colt presented me with a single red rose. It smelled wonderful.

"You look beautiful." Colt said.

"Thank you, you look great too." I said awkwardly.

I was not use to nice complements; then again, that one-year trip overseas really upped my game in the crossdressing department.

I turned back to see Lin practically bouncing up and down with excitement in the kitchen window giving me a big thumbs up. I slid into Colt's mustang and we backed out of the driveway on onto the street.

"You could have worn pants if it would make you more comfortable." Colt said.

"I am comfortable like this." I said. "Dressing like a boy, makes me uncomfortable."

It is the truth, I wanted to be a girl since I was twelve but that is not how society works. I shudder to think of all the years I repressed the urges to be myself. I wish I were born in the present day to parents that are more progressive in nature; things would be a lot easier for me. Colt broke the long moment of silence.

"If you could do your fist time over would you and what would you change?" Colt asked me.

"You mean my first time with a man, right?" I asked.

"Right, your first time with a man." Colt said.

"I would have done it with a different person, the guy I picked, Dave, ran around, and told everyone I worked with. By the next day when I came into work, I had the cooks threating me and the servers trying to hook me up with better looking people. It was a nightmare; I had to leave to get a new job in a different town." I explained.

"How old were you?" Colt asked.

"I was 18, and fresh out of High School." I said.

Colt pulled into the alley that leads to the parking lot of Maria's, a little restaurant next to the movie theater. Good home cooked meals, family owned and operated. We walked the short distance to the doors of the restaurant, Colt made a quick grab at the door and held it open for me, I sighed and accepted it graciously. One of the owners took us to our seats near the front of the restaurant. The clientele here would fit in any mobster movie, matter of fact I bet Danny Greene's car bombing was planned right here, at one of these tables. Ok, I am joking but you get that vibe, it is a nice sit down place.

Right after introducing herself the waitress complimented me on my eye makeup. I was shocked and took me a second to recover. I thanked her and explained where to get the eye kit. Colt ordered the steak and onion rings and I ordered the open face roast beef special. We both ordered Ice Teas. Colt changed his order to the open roast beef special. Not a fancy meal, but Colt and I are not pushing to impress anyone. We have actually been chatting almost every night. I am amazed we still find things to chat about.

"If you could do it all over what would you do differently?" Colt asked.

"I think I missed out on all the girly things in High School." I said. "The home coming rallies, the crushes, the making out, you know the typical teen stuff; maybe even be a cheerleader.

"You would want a mulligan on life would you?" Colt asked chuckling.

Laughing I agreed, life owed me a mulligan.

Our specials came and we talked more about the food than ourselves. The owner stopped by the table and asked how everything was and smiled at both of us, I thought there was something more to his smile at me than an innocent smile. Colt dismissed my suspicions, but I was still on guard when I went out in public dressed.

The waitress stopped and refiled our drinks and asked if everything was ok taking a moment to talk about dessert. Colt and I smiled at each other and passed on her offer. Over all everyone in the restaurant was nice to me, and yes, there were some looks my way but nothing to worry about.

Colt took the bill as soon as it hit the table but I insisted on leaving the tip. I knew the bill was just over twenty-seven dollars but I slipped a twenty-dollar bill under the edge of my plate for her. She was nice and I could not have asked for a better experience.

We stood and started to leave; our waitress came over and thanked us for visiting the restaurant. I asked her where the rest room was and she took the time to walk me to the women's rest room. I hope she understood how much everything she did today meant to me.

Walking out of the back door the midday sun was blinding and took a moment to adjust, I did not realize how dark it really was in there. Walking with Colt I was feeling euphoric and I was very optimistic we would have a great time at the movie.

The movie theater that was right next door but the theater building extended into the parking lot by a hundred feet further than the restaurant requiring a little bit of a walk. I am not sure who initiated it but it seemed like a novelty when we began walking arm in arm through the parking lot to the back door of the move theater. Colt got to the door first and held it open for me but I beat him to the next and held it open for him.

It was apparent Colt was raised with old-fashioned manners and a respect for women, I did not fault him for practicing what his mother or father programmed into his brain, and I made a mental note to let him patronize me and promised myself to enjoy it.

The movie theater was darker than it was outside but it only took a moment for my eyes to adjust, something I gained recently: the ability of seeing well in low light. I lost my dark brown eyes in my experience overseas, and they transition to the hazel I have now, something to save for another story.

We had to walk through the movie theater down a carpeted hall to the front where the concession stand was located. A male and female worked the concession stand and ticket sales, both high school age. The male whose well-worn nametag said his name was Sam, gave me a once over and offered Colt a smile with a nod and then a fist bump.

Together we had decided on an action movie with excessive violence, unreasonable nudity, a plethora of vehicle chases, and all of it topped off with a dash of romance. A movie made in heaven. Sam gave Colt our tickets and the girl made our popcorn and poured our Dr. Pepper. At the end of the transaction, I noticed her equally worn nametag said Alex. The thought did run through my mind the movie theater only had two nametags and all the employees shared them.

"I do not believe I've ever seen that fist bump ritual before." I said.

"I'm sure that was an approval of my choice in women." Colt suggested.

Colt presented or stubs to the ticket taker and I followed Colt to about three-quarters up and pretty much center of the theater. The plan was a weekday matinee to avoid crowds and it looks like we succeeded, the theater was almost empty.

We got the medium popcorn and Dr. Pepper to share; I really did not want to drink anything because I was nervous of the bathroom situation here. I did not know if someone would freak out if I used the socially accepted wrong restroom.

During the previews, I crossed my legs and managed to let my leg rest against his. He obviously did not argue but he did offer me some popcorn, I opened my mouth and let him feed me a couple pieces. Somewhere around the halfway point of the movie, we were holding hands and it actually sent a shiver down my arms. Not because it was cold, it was something else.

Looking at Colt in the lights playing on his face, I mean his dark hair, broad shoulders, and strong jaw, I could do, wait I have done much worse. He is not a body builder but I have not noticed any fat on him. I shifted in my seat allowing our shoulders to touch. I am not a real girl but my panties were getting wet thinking about having sex with my stallion.

I was thinking about going down on him right here in the theater. I tried to focus on the movie but it does not help, my mind wanders back to sex then something darker crept into my thoughts. Colten wants a relationship. The idea of someone falling in love with me was a scary proposition. Sex was easy for me but relationships not so much.

I look at Colt again, watch the lights from the movie play across his face, push away the relationship fears, and just try to focus on the movie.

By the end of the movie, I had resolved myself to the fact that Colt and I may not have sex today. My theory seemed to be confirmed when Colt asked if I wanted to go for a little drive. I wanted to say no and insist on going home and having sex like rabbits.

The kiddy movie let out the same time our movie did so there was a herd of second and third graders fit to trample us getting out. There were so many kids everywhere, it was like a pipe burst, and the cinema was going to sink.

"Fall back to the APC." I laughed.

"Get to the chopper." Colt says in his best Arnold voice.

I chase a strand of hair out of my eyes as Colt and I make it to the exit and pour out in to the parking lot. Gathered in the parking lot were school busses to pick up the kids. We make it to the mustang and chuckle how we survived the horde of kids.

After a few minutes, we pulled back into my driveway.

"I thought you wanted to go for a drive." I asked.

"I thought about going for frozen custard but I think we may have had enough food for a little while." Colt said.

I agreed and offered him to come inside for some Kraken and Cokes.

Colt followed me into the house and I invited him to make himself at home while I used the restroom. I came out and found Colt on the couch fussing with the TV remote. I went into the kitchen and came back with two Kraken and Cokes. Colt settled on the love songs radio channel, Chris Isaak's Wicked Game was playing as I settled next to Colt on the couch. Then we kissed.

Colt pecked me on the lips. I lightly kissed him back. Colt surprised me with a deep passionate kiss, when he tried to retreat I held on and ran my tongue along his bottom lip baiting his tongue to come out and play. His tongue pushed its way past my lips and into my mouth. The only thing more intimate than French kissing is oral sex in my opinion. Colt's tongue is in my mouth, greedy, wet, and demanding and I am in heaven. Right now Colt has moved over my reclined body. We are still on the couch and have been kissing for maybe thirty minutes without a break. It was as if we were in high school or something. We take a break and we both go for our drinks. Setting our drink down Colt moves over me, I recline a little on the couch.

Looking into his hazel eyes I say: "What big eyes you have."

"All the better to see you with." Colt says his smile bright and perfect.

"What big teeth you have." I said.

"All the better to devour you." Colt said.

"Are you?" I asked.

"That's the plan." Colt said as he reached up under my dress cupping my ass and lifting me, centering me on the couch better. When he withdrew his hands, he relieved me of my nylons and my thong in one smooth motion then he dove straight between my legs. He took all of me into his mouth. Long slow movements with his tongue. A husky moan escapes colt's mouth as he nibbles on the inside of my thigh. I feel his 5'0 clock shadow tickle my thigh as he moves in for more.

I weave my fingers in his tasseled dark hair and let out a muffled Oh my god your good. His tongue feels huge as it lavishes my private parts. I cannot believe it feels this good. I do not know what he lubricated his finger with but I felt his finger slip inside of me. I looked down, between my legs watching his head move. His finger and mouth seemed to be working together perfectly. I could not help it.

"I'm close." I gasped.

He was only down on me for five minutes, he already had two fingers in me, my legs started shaking uncontrollably, and my back arched. When my eyes opened, I looked down to see him licking his lips. I cannot remember the last time someone went down on me and I never had anyone do it so well.

I watched and Colt removed his shirt and pants, my jacket had come off before I sat on the couch so Colt helped lift my dress over my head and he tossed it into a nearby chair, I undid my bra and let it fall to the floor. Colt still had on a pair of black boxer briefs, his excitement was obvious as he worked to discard those.

My mouth watered looking at his cock, I could not tell how big it was, but it looked wondrous.

"Let me suck your cock." I begged. "Give it to me."

"Oh you're getting it." Colt said.

Colt pulled himself up, took my right nipple in his mouth, and massaged my breast with his free hand. Electricity flowed through my body as he sucked and nursed on me then he moved to the left. He altered the pressure, his technique made me feel weirdly maternal. I cradled his head in my hand as he sucked, liked, and did his magic.

Distracted by him kissing and biting my neck he maneuvered between my legs and entered me. I felt the pressure and pain of his cock at my entrance but he forcible pushed straight in until his balls were against my ass. I was hilted before I could say anything. My legs wrapped around him with my heels digging into his fine ass and my arms around his broad shoulders. He kissed me, forcing his tongue between my lips and over my tongue as he pulled his cock back and started pumping. I was officially being fucked and fucked hard. Colt moved down and kissed my neck as his cock moved in and out of me like a jackhammer. I could not form words but I could moan and make little mewing noises as he pummeled my hole. It was clear he owned me every time his balls slapped into my ass. It was all I could do to hold on. His trusts were quick hard and directed upward, towards my belly button. Colt knew exactly what he was doing because I started getting that feeling again.

I did not think it was possible for me to have two orgasms that quickly but I knew what was happening. Colt's cock was massaging my P-spot and in my mind, I could not tell if he was fucking me or if I was fucking him. Everything was a little blurry but I knew he felt my body contract around his cock and my hips jerking uncontrollably. When my body cums this way it lasts four times as long as a regular orgasm and it is twice as intense.

When I opened my eyes, Colt was still fucking me ruthlessly while looking into my eyes and he was smiling. No, he was gloating in the fact that I came from his fucking me. It is ok, he can gloat all he wants if I get that glorious feeling.

I was spent, all I could do was lay there and let Colt use my body as a fuck toy until he came. Seriously, I felt compelled to be his cock sleeve for all the wonderful emotions and feelings I felt. Colt helped me into the doggie positon, ass up and my head down on the armrest and he resumed just literally pounding my ass like a nineteen year old. Finally, Colt stiffed up and I knew he came; we crumpled into a pile on the couch. Colt pulled the quilt down from the back of the couch and we just held each other for a few moments.

"You would make someone a great wife." Colt said.