Kyle - My First Date

My name is Leigh. Well my girl name, I am a cross-dresser. I just feels right to me and I guess that is how I am. I have been putting pictures online of my female-self to share with other people. It is through a photo-sharing chat website that I made many new online friends.

My best friend Lisa invited me to a party she was hosting one Friday night. I always enjoyed hanging out with Lisa and her friends so I accepted.

That night I dressed conservatively: opaque black tights, grey skirt, and a black pull over turtleneck sweater, flats and light make-up. Lisa lived less than five streets away and it was a beautiful fall evening with a light wind so I decided to walk. I threw on a black windbreaker and headed out the door.

The trees looked magnificent in their fall regalia and I imagined Kyle and me on the back of his Harley winding through the trees for a weekend getaway. I have had many dreams of Kyle and I doing things together but none of them will come true unless I can convince him to share these same dreams. Kyle will be at the party tonight and I plan on become his daydream before the night is over.

Kyle is Lisa's brother and works for a 24-hr fitness center; he acts completely obsessed with working out but still smokes and drinks on occasion. Kyle was 6 ft. 4" tall, 235 pounds, 47" chest, 32" waist, and 18" biceps according to the fitness center web page. Lisa and Kyle were born in the Netherlands and both have natural blonde hair and blue eyes.

I walked up to Lisa's front door and rang the bell. Alex, Lisa's girlfriend, answered the door, invited me in and started to introduce me to the other guest. I was polite and made small talk as I slowly made my way closer to where Kyle was standing.

"Leigh, you look beautiful tonight, "I'm so glad you made it." Kyle said as he gave me a warm hug.

"You look great yourself Kyle, how have you been?" I asked.

"I've busy helping my little sister with her wedding plans," Kyle answered.

Kyle and I made small talk for about 5 minutes until Lisa interrupted us. Lisa was glad to see me she hugged me and we stepped outside to have a quick cigarette.

"Leigh, now you know the rules about my big brother," Lisa said playfully.

"I was being polite and nothing more," I whispered. "I didn't hug him he hugged me"

"He is still learning who he is." Lisa chided me "You have to go easy on him, remember he is not experienced with guys"

"He has a lot of experience with girls and I just happen to be a girl tonight...right?" I asked.

"That's not what I'm worried about. Promise me you will follow his lead if anything happens between the two of you." Lisa asked

"Why are you all of a sudden worried about Kyle and me when he barely knows I exist?" I asked.

Lisa did not answer me; but I could tell she was keeping something from me. I decided to let it go.

"Lisa, I promise." I said.

I waited a few minutes before returning to the party, I felt Lisa needed a little space. Once inside, I went to the kitchen where the drinks were and poured myself a glass of wine. Lisa was in the living room, she seemed to have recovered from out chat outside. I thought it best to visit with the guests in the family room, away from Kyle and Lisa for a little while.

My self-exodus was short lived; Alex came in and invited us all to the back yard. "There are envelopes with your name on them just outside the door, Please do not open them until we ask you to." She said.

I stepped outside and the setting sun was casting a purple and red hue on the clouds. All the trees in the back were illuminated with small white Christmas lights, a small bonfire in the center of the yard crackled while a CD player near the back of the house played a soft classical tune.

Kyle startled me when he called my name and handed me a lavender envelope. "Your envelope was right next to mine," Kyle explained.

Lisa thanked everyone for coming to the party and Alex made a speech about how important it is to have good friends throughout our lives. Then together Lisa and Alex asked everyone to open their envelopes.

I opened my envelope to find an invitation to Lisa and Alex's wedding, well their exchanging of vows to be more exact.

We all took turns congratulating the brides, Lisa was almost in tears she hugged and whispered in my ear "I trust you".

I thankfully found a seat on a covered glider near the bonfire where I could sit without the hassle trying to in one of those canvas-folding chairs with a skirt on. I sat there lost in thought about what Lisa just said to me.

I was not paying attention to the people around me as much as I was watching Lisa and Alex weave in and out of conversation with their guest. I was thinking how happy they looked together when Kyle startled me by sitting next to me on the glider and offered me a glass of Champaign.

"You came to the party alone?" Kyle asked.

"I've been single for about 4 months now." I replied.

"Any promising leads?" Kyle asked.

"I've decided to stop looking for right now, if the right guy comes along...maybe" I responded. "There was one really nice guy, but your sister did not approve of me asking him out."

"My little sister can be very protective of those she loves Leigh, I wouldn't let her make all your decisions," Kyle stated.

"Speaking of decisions, I thought Lisa and Alex were going to the Netherlands to get married." I said.

"They still are, we thought it would be nice to have something locally so everyone could attend." Kyle said.

After a few moments of silence, Kyle started talking about how amazing the trees looked on his ride and how much he enjoyed the smells of fall. I admitted I was thinking the same thing earlier this evening.

Kyle and I continued to sip our champagne and chat about this and that. I was actually surprised about how many things we had in common. I also learned he rode his Harley up from Orrville that night.

Kyle pulled out a pack of cigarettes from his pocket and started searching the other pocket for his lighter. I reached in my purse and offered him my lighter. I lit his cigarette for him and he thanked me.

I said, "It's ok, I light all my bitches' cigarettes"

Kyle laughed

"So any new love interests in your life Kyle?" Placing my hand on his thigh as I asked playfully.

Kyle leaned back with is arm resting on the back of the glider behind me and admitted, "There is someone I'm interested in but the timing has been bad, plus I haven't decided how I want to let them know I'm interested."

"Kyle, sometimes you have to be impulsive and make the first move...seize the moment before the moment is gone," I suggested

Kyle smiled at me and said, "Well maybe we should seize some more of that free Champagne before it's all gone."

Kyle took my empty glass and offered his hand to me. I flattened out my skirt before we walked back inside. Once we got in the house, I excused myself to the Ladies room while Kyle refiled our glasses.

Several of the guests were leaving and I could hear Alex and Lisa saying their goodbyes and thanking them for coming out tonight. Kyle had slipped into the restroom as I came out, so I sipped my drink while waiting for him in the kitchen.

I was looking out the patio doors when I saw Kyle's reflection coming up behind me. Without turning around I opened the door with the hope that Kyle would follow me outside. He did not disappoint me.

I walked up to the fire and turned around to greet him and I caught him gazing down.

"Were you just checking out my ass mister? I playfully scolded him as I stepped closer to him.

"Well I couldn't help myself, you do have one choice ass," Kyle jokingly admitted.

I stepped even closer to Kyle, looked up into his blue eyes, and flirtingly asked if a choice ass was better than a nice ass. Kyle looked down at me as he reached around and placed his hand on the small of my back.

In a soft voice, he explained, "choice is better than nice."

I tilted my head back a little farther and my lips voluntarily slightly parted themselves expecting the inevitable, Kyle was going to kiss me. Kyle slowly tilted his head towards me and...

"Hey I was looking all over for you guys," Lisa playfully yelled from somewhere behind Kyle.

When Kyle broke, his gaze I almost fell over, Kyle's hand caught me but he quickly pulled it away once I regained my balance. I went from euphoria to cold, empty, and alone. As fresh air rushed into my lungs, I wondered: how long had I been holding my breath?

Kyle exchanged a conversation in Dutch with Lisa of which I only caught a few words.

Alex and Lisa looked completely spent and the momentum between Kyle and I was lost for the night. Looking up at the night sky it looked like rain and I had a long, solitary walk home so I hugged Lisa and said my goodbyes, congratulating both of them. I told Lisa that if there was anything I could do to help to call me.

Kyle announced that he was going to walk me to my car.

"I didn't drive, I walked and I better get going before it rains," I said.

I started walking across the yard when Lisa stopped me.

"I don't want you walking home this late at night," Lisa told me. "Kyle will give you a ride home."

"On his bike?" I asked almost too eagerly.

"Are you ok with that?" Kyle asked.

"If you promise no wheelies I'm ok with it," I answered.

Kyle disappeared into the house to get his jacket and helmet. As the garage door opened, Lisa reminded me not to hurt her brother.

"I live 5 blocks away, nothing is going to happen" I assured her.

Kyle had already started the Harley Road King and waived me onto the bike. He handed me a pair of riding glasses to wear. I had to bunch my skirt up a little too high to get on the bike; thankfully, I had tights on. I sat behind Kyle, my legs spread against the small of his back with my arms wrapped around him. Kyle asked if I was ready and I started to laugh.

"What's so funny? Kyle asked.

"This feels like some weird Kama Sutra backwards missionary positon" I replied.

Kyle maneuvered the bike down the driveway and onto the street. Just when I thought, things could not get any better I felt the Harley engine thump. Thump, thump, thump. It was as if the seat had its own built in vibrator and with me leaning forward, holding onto Kyle the thumping was hitting all the right spots.

At the first stop light, I realized I forgot my purse and asked Kyle if we could turn around. Lisa must have heard us pull in the driveway. She came out of the house with my purse, and placed it in one of the saddlebags on the back of the bike.

We arrived at my house just as it started pouring down rain. I slid off the bike, grabbed my purse and ran onto the porch with Kyle right behind me.

I invited Kyle in while we waited for the rain to subside. I told him to hang his jacket on the back of a kitchen chair. I slipped off my wet shoes as Kyle removed his boots and laid his socks on top of them to dry. I grabbed two bottles of water from the fridge, walked Kyle into my living room and invited him to make himself at home. I stepped into the next room, took off my turtleneck, and put on a button down black blouse. Shortly after we were on the couch together when the power went out.

I lit the decorative candles on the coffee table so we could have a little light while we waited out the storm.

"I'm so sorry, I must look a mess right now," I exclaimed to Kyle as I tried to brush my rain soaked hair away from my face.

Kyle responded by slipping his right arm around me, pulling me closer to him, and he kissed me.

"I wasn't expecting that" I said.

"Well I'll just have to do it again," Kyle said.

I closed my eyes; I could smell Kyles intoxicating cologne mixed with the smell of the lavender candles on the coffee table. I became very aware of Kyle's hand on my back pulling me closer to him and I instinctively reached up and placed my hand on Kyle's chest just above his heart. Kyle's kiss landed gently on my lower lip, it felt like the tip of a rose petal landed on my bottom lip. Before I could say anything Kyle kissed my upper lip and paused for a moment. Involuntarily my lips parted giving him full access to my upper lip. Soon I felt tip of his tongue tracing just the inside of my lips. Our tongues met and danced together until his tongue completely invade my mouth.

Kyle was inside of me, it was just his tongue, but mentally it was the most erotic thing that has happened to me all year. It was a man's tongue inside my mouth and I was enjoying it.

I felt safe in Kyle's arms; we began reclining as we kissed. I could not perceive the problem it may cause because I was so into our make-out session I did not care what was happening as long he continued to kiss me. I attempted to maneuver my hips and legs against the back of the couch so we could lay side by side. Kyle misunderstood and we ended up in a missionary position.

Kyle was passionately kissing the side of my neck, with his right arm hooked behind my neck and his left hand kneading my left breast. As I lay there underneath Kyle, I imagined this is how the impala feels when the leopard catches it.

I was in euphoric bliss until I felt a tugging on my blouse. Kyle was unbuttoning my shirt. I put my hand on his and asked him to stop. Kyle ignored me and continued to unbutton my shirt. When I protested, again he stopped and then continued kissing me.

Kyle paused and said, "I promise it will be ok, trust me."

The words promise and trust made me look at my situation. We still had our clothes on, but Kyle was on top of me. Fighting him off me would be impossible.

"Kyle, I need to sit up" I said.

I touched his face gently and said "Kyle, sit me up, please, I need a break."

He complied; Kyle moved his right arm around my back and helped me into a sitting position next to him on the couch.

"What's wrong?" he asked.

"Nothing, I need a break" I said as I moved across the couch just out of arms reach.

"Should I leave?" he asked.

"No...I want you to sit where you are, I don't want you to leave," I said.

I pulled a cigarette from the pack on the coffee table and lit it, and then I smoothed out my clothes a little. When Kyle reached for the cigarettes, I playfully slid them away from his hand.

"I'm sorry those are on my side of the coffee table," I said playfully.

I slid the pack toward Kyle along with the lighter.

"Take your shirt off Kyle and hand it to me," I playfully ordered.

Kyle did as I asked. I flipped his white dress shirt around and showed him all the red lipstick marks on the collar.

"Do you want to explain this to your sister?" I asked.

I put my cigarette out and took a long swig from the water bottle. I moved over to where Kyle was sitting and started kissing him and running my hand across his chest. Kyle's hand started rubbing my leg and the other started massaging my breasts. I stopped him from playing with my chest but allowed the other hand to rub my leg. I asked Kyle to move towards the center of the couch so I could sit on his lap facing him.

"Kyle you know I'm not a real girl, right?" I asked in a playful tone

"Yes I know that." He responded

"And you know these are not 100% me, I'm wearing a water bra and enhancers right?" I asked while cupping my breasts.

"Leigh, your boobs really complete you, I like them fake or real I think they look great," Kyle stated as he started to unbutton my blouse. I did not stop him. When the last button was undone, I took it off and tossed it on the floor.

Kyle had reached up and cupped my breasts and he asked me to remove my bra. I undid the back clasp and tossed my bra onto the floor. Kyle pulled me towards him, sucked my left nipple into his mouth, and flicked his tongue across it so fast it felt like a vibrator. It felt so good I grabbed the back of his head and held him there. It was hard to catch my breath it felt that good.

When Kyle's mouth released me, I twisted my torso so my right nipple was right in front of his mouth. He hesitated; I was still trying to catch my breath. I relaxed my grip on his head as the sensation in the left half of my chest started to fade.

"Kyle, I really liked that," I said.

"I could tell" he responded.

My body relaxed, I started moving my nipple around his lips, my head was hanging limp near the right side of his neck. I began kissing his neck and shoulder.

"Baby, please I want you to do it again," I whispered in his right ear.

"Is that right? He asked while moving both of his hands to my hips.

"I need it really bad, stop teasing me" I whispered as I kissed his shoulder.

"What's in it for me?" he asked coyly then he licked my nipple and blew on it.

I grabbed a hand full of his hair pulling his head back; I kissed him shoving my tongue forcefully into his mouth. I moved back to kissing his neck and shoulder.

"If you do it...I'll suck your cock dry," I whispered.

Kyle pulled my hips into him and his mouth and tongue were doing magical things to my right nipple. I hung on to the back of his shoulders with both hands. When he finished with my right breast, he began consuming my left nipple again. The left was still sensitive from earlier and I threw my head back and loudly professed how great that felt.

Kyle and I cuddled in this position with my head resting on his shoulder until I had regained my breath. My body startled whenever the hair on his chest brushed my nipples.

I got up and found by bra and my shirt. I put my bra on and the cool inside fabric made my sore nipples feel better instantly. I asked Kyle to hook the back for me, something I could never do behind my back with fake nails. I tossed the shirt on and smoothed out my skirt.

I turned to Kyle, kissed him, and asked if he wanted the blowjob now or did he want a rain check.

"It's raining now" Kyle joked.

"Then you need to lose the jeans cowboy" I said as I dropped to my knees.

Kyle stepped out of his jeans and kicked them away. I reached up and started working his underwear down. I was not expecting to have a spring-loaded cock smack me in the face. It felt like he swung it.

Kyle's cock was just like the rest of his body: big thick and solid.

Kyle was too tall for me kneeling so I asked him to sit on the couch. I knelt between his thighs and took his cock into my hands his sack was the largest one I have ever seen. His cock was 20 fingers long, 6 fingers wide at the base with a slight downward curve and uncircumcised.

I started by licking the sides, top and bottom of his cock to get it lubricated being careful to avoid the tip. I pulled his foreskin all the way forward and I carefully took the first 2" of his cock into my mouth. I Australian kissed it by sliding my tongue between the head and the foreskin and slowly rolling my tongue around inside his hood. Then I pulled the foreskin back and started slowly pumping my mouth up and down on. While my other hand slid his foreskin towards and away from my lips with a slight rolling motion. When Kyle started begging me to fuck me, I knew it was time to move.

I turned my head allowing Kyle's cock to rest on my cheek as I licked his balls. I swirled tongue around the bottom of his right nut then I slowly licked until I found his left nut. I pushed my tongue into his sack to separate left from right then I made a "come here" motion with my tongue before moving over to service his left nut. I started playing with his foreskin in my right hand making slow pumping motions. The noises Kyle started to make were either pure agony or ecstasy; since he was not trying to escape, I had to assume it was the second sensation.

I continues stroking his cock with my right hand while my mouth pumped up and down the first 4 inches with increased rhythm soon; my hand and mouth were in harmony with each other. Kyle again asked if he could fuck me. This time I stopped everything I lifted my head and said, "I'm sorry when my mouth is full I can't hear you"