Kyle - My First Public Date

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Leigh’s first public date.
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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. All my stories are based on truth; but the places and names have been changed.

Kyle and I have been seeing each other for about six months and we have become good friends; however, my reluctance to go out in public dressed was beginning to limit our relationship. Kyle wanted to date me without limitations of where we could go or do and I was not comfortable dressing as a girl in public.

Kyle and his sister have helped me explore who I think I want to be without pressuring me to be someone I was not. So since Kyle really wanted this so I agreed to what he promised to be an all-American date night.

I was nervous and excited at the same time as I stepped out of the shower and began my transformation process. First thing was to dust my face with baby powder to make sure I was completely dry then came the concealer foundation and the rest of the make-up. I had masturbated earlier so I knew as I fitted my boy-parts into my shiny black gaff that I would not have any issues. A black body shaper, around my midsection, followed my homemade breast forms and a black "water bra". I unrolled the semi-opaque flesh toned nylons up my legs one at a time, approving of the hint of glitter they possessed.

I slipped on the long sleeve black dress where the hem stopped halfway to my knees then a shoulder length dark brown wig with chestnut highlights. Dangling silver earrings and velvet Black Suede Lace-Up Heels finished the outfit.

I added some final touches to my make-up and practiced walking up to and away from the long mirror in the hallway. I was satisfied I had done everything I could but I wondered if my date be satisfied with the results? The doorbell rang.

I walked across the living room to the front door. Kyle was standing there with flowers and after he looked me up and down, and with a genuine smile he told me how beautiful I looked. I could feel the blood rush to my cheeks as I invited him in.

Kyle was pretty darn good looking himself. He manages a 24-hr fitness center and at 6 ft. 4" tall, 235 pounds, with 18" biceps it is no surprise he is completely obsessed with working out. Kyle was born in the Netherlands and has natural blonde hair and blue eyes.

I invited him in. We hugged and Kyle told me how beautiful I looked again, I pecked him on the cheek and excused myself to put the flowers in water. This was the first time a guy brought me flowers. Normally I would be invited to their house or some hotel for sex then when they were done with me, or I with them we parted ways. Kyle was different, yes, we had sex on the first date but he actually wanted to hang out with me and not just have sex. I was very intrigued to see where this went and it was going to allow me to become more immersed as a female.

I walked back into the living room, deliberately swaying my hips as I walked up to him. Kyle gave me a big hug and kissed me. I always felt small when Kyle held me in his arms. Kyle was at least 8" taller and his workouts centered around weights where my workouts focused on swimming and aerobics.

I was more than content to stay home and watch a movie on the TV with Kyle, but he was adamant that he was taking me out tonight.

Kyle led me to his car, well roommates van. Kyle's Mustang was in the shop again and snow was in the forecast for tonight so his motorcycle was not an option.

The van was a mini camper with captain's chairs in the front and couch in the back. It also had a small refrigerator, sink, and a small table. The inside was covered in purple carpeting and over the refrigerator on the driver's side was a white shag carpeted playboy logo. It was obviously more shag wagon than camper.

I was more excited than nervous as Kyle maneuvered the van through town, even when he pulled into the parking lot of a movie theater I was not worried. The parking lot was in the back of the theater and the only open spot was all the way in the back row. That is when my excitement turned into panic; the theater was going to be packed.

When Kyle opened my door and helped me out of the van, it felt a little awkward having a guy help me out of a vehicle, but my lack of experience in heels insisted on Kyle being a gentleman.

Kyle placed his hand in the small of my back as we walked toward the theater entrance making it clear that we were a couple tonight and he even and he held the door open for me as we entered the theater.

I leaned into him and whispered, "You are racking up a lot of points tonight mister."

"Oh, and what reward have I earned so far?" Kyle playfully asked as he kissed the top of my head.

"Anything on the bottom shelf." I responded, referring to the carnival games where you have to prove your skill to earn the prizes on the upper shelves.

We bought our tickets and moved to the concession stand where two guys in their early twenties were standing behind the counter. They were staring at me with stupid half grins on their faces; I just knew they were going to say something. As Kyle ordered us a small popcorn and a medium pop, his hand went behind my back and cupped my ass; I jumped, not expecting anything like that. The counter guys kept any comments they had to themselves.

We found our seats and settled into watching the movie. Kyle had his arm around me and the movie was good but my mind started to fill with excitement. Well excitement and pride in myself that not only that I had gone out to a movie theater, but a good-looking guy had offered to take me out to the theater.

Kyle began playing with my earing with his arm that was around the back of my seat. When I turned to look at him, he kissed me, a slow deliberate kiss on the lips. Then he went back to watching the movie with a playful grin on his face. I could not let that go unchallenged so I slipped my hand down to his leg. His dress pants felt very thin as I slid my hand up his thigh to his crotch where I found that definite bulge allowing my index finger to trace the outline of his balls through his pants before moving back to his thigh.

The movie ended a lot sooner than I wanted it to, I was enjoying the time with Kyle's arm around me. We sat through the credits and started heading towards the exits at the rear of the theater that lead directly into the parking lot. I held onto Kyle's arm as we walked through the parking lot. When we arrived at the van Kyle asked if I wanted to go in the back for a little fun, I quickly said I would love to!

Kyle opened the side door of the van for me and as I sat on the couch in the back, he closed the curtain behind the front seats, now it was almost completely dark in the back of the van. Kyle settled in next to me on the couch at the back of the van with his left arm stretched out on the back of the couch behind my shoulders and with his right, he moved a bit of my bangs, hooking them behind my ear while staring into my eyes. He told me how beautiful I was, and then he kissed me. We looked into each other's eyes and we kissed again.

He was being ever so gentle, his left arm around me, out lips meeting, the whole thing was very intoxicating to say the least. I was completely enjoying everything Kyle was doing, so when he started massaging my left breast I let him, but I whisper a reminder in his ear to be gentle with those. Kyle was kissing and gently sucking on the side of my neck when we heard people talking outside of the van. It was people walking back to their cars; we had been making out for two hours already.

I moved to the floor of the van, kneeling in front of Kyle and unbuckled his belt and he shifted to allow me to slide his pants and boxer briefs down; as he did, his cock sprang out almost smacking me in the face. There was nothing small about Kyle and his cock was definitely a challenge to suck. I pursed my lips to the tip of his cock, like you would take a large straw and with a sucking action I slid my mouth over his cock with one motion taking as much of him into my mouth as I could. Kyle made a deep throaty grunt as I did this and his hand instinctively went to the back of my head but he quickly pulled his hand away. I moved my mouth over the first 2 to 3 inches of his cock as my hand pumped his cock establishing steady rhythm with my mouth and my hand. Soon his hips were lifting up off the couch to meet my lips and tongue.

"Oh, what a good girl" Kyle purred as the head of his cock probed the back of my mouth. With each of his thrusts into my mouth, he continued with "Mmm yeah, that feels nice", "that's so good baby", "OMG, your mouth feels incredible", "Keep doing that", and a few "Mmm yeah".

Kyle announced he was close and started making throaty grunting noises, soon I felt the first twitch of his cock in my mouth and quickly he filled my mouth with his cum and I swallowed all of it. I held his cock in my mouth until it went limp enough to fit in my mouth completely.

That was absolutely amazing, Kyle stated.

"If you keep treating me as nice as you have I'll have to think of a better way to reward you, so just think of that as a down payment for tonight." I answered.

We collected ourselves and moved to the front seats of the van. I was busy with touching up my make-up as Kyle maneuvered the van onto the street. I thought we were headed to one of the usual clubs on the far side of town but Kyle surprised me once again by parking the van in front of the 24-hour pancake house almost right across the street from the movie theater.

"Relax, everything will be alright, trust me." Kyle assured me as he held my door and helped me out of the van.

Kyle was right, everything was all right, and actually, it was better than all right. Kyle knew the owners and we had a great time. Kyle and I had some quality time just talking about, well just about everything. Kyle broached the subject of sexual fantasies and I may have said a little more than I should have, but my answers did not seem to bother him at all.

We pulled into my driveway well after two in the morning, and I invited him inside. We barely made it into the living room when Kyle spun me around, kissing me as soon as I was facing him, his hands quickly moved down my back to my butt, squeezing and kneading them as he maneuvered me towards the hallway. I vaguely remember dropping my purse to the floor as Kyle's mouth moved along my jawline to my neck. His arms held my body flat against his as he maneuvered me through the bedroom door while he kissed me, when his tongue slipped past my lips my arousal increased, I wanted him so bad right then. When the back of my legs touched the bed he hesitated and told me how beautiful I was. I pulled at this belt and unbuttoned his shirt soon; I was on the bed almost completely undressed watching him franticly removing the rest of his clothes.

We were on our sides kissing when his hands moved between my but cheeks and I felt the coldness of the lubricant as his fingers made tiny circles around my opening. I knew what he wanted and he knew I needed it bad. Kyle adjusted himself a little and began kissing and biting my neck as my leg rested on his side giving him full access to my ass. Kyle rolled me over onto my back with himself above me, and goosed me with two well-lubricated fingers. His fingers pushed into me until his knuckles stopped him. My hips jumped off the bed only making my impalement more dramatic. Kyle asked if I was ok, not that it would have made any difference to him right then, but he did ask, and all I could do was nod my head that everything would be ok as I tried to catch my breath. This was how it was every time I was fucked in the ass and Kyle knew I freaked out a little in the beginning and said things I did not mean, but I still wanted him inside of me.

Kyle began kissing and sucking on my nipples as his fingers remained inside of me. I loved having my nipples played with and he knew that, soon I had forgotten about any of the initial discomfort. Kyle rolled me over onto my hands and knees as he moved behind me, spreading my knees apart to accommodate himself behind me. I could feel the head of his manhood sliding between my cheeks then it slid up and down, as it looked for my opening. As soon as his cock found its mark, Kyle placed both of his hands on my hips and increased the pressure until the head of his cock popped inside of me. I groaned and verbally complained about Kyle's girth as he pushed more and more of his ridged cock inside of me. I begged him to slow down to allow me to adjust to the girth of his manhood, but it seems my complaints and moans only encouraged him to force more of his cock into my ass. Soon I felt the pressure of his balls against my ass and I knew I had just been hilted by my lover. Pausing, he leaned over my panting body and said in a semi-serious angry tone, "I own this body".

He was right, I was allowing him to own me and at that, moment, I went from trying to pass as a girl to successfully being the girl tonight. I was his girl, and the pain and pressure I felt a second ago quickly turned into a fulfilled moment and as he pulled his cock from me I quickly felt empty, but only for a moment. He slid back inside of me and soon he had established a rhythm. Our bodies making loud slapping sounds together in the night. Then I felt it, it was a sensation, almost as if my penis was rubbing on the sheets or something, it was the same sensation as if I was the impairer instead of the impaled but that did not make sense. Kyle's 8.5" cock was fucking me, how could I have this sensation. Each time Kyle thrust into me the sensation became stronger, and it was leading me to something I had to have. I reached down and checked myself because my mind said I was hard, but I was not. Kyle continued his thrusts and I was getting closer to orgasm. I was so lost in this feeling, focusing on it because I was afraid, I was going to lose it somehow and then I had the most powerful orgasm I have ever experienced. So powerful, it washed over me and bathed me in its power. I glanced back at Kyle and he was smiling, he reached down and felt the wetness I had left on the bed and he chuckled a little before resuming fucking me. I had my orgasm but Kyle was not finished, so I just enjoyed the moment and became lost in his rhythm.

Soon Kyle became more forceful and I could feel the head of his cock poking at my insides, he was harder and thicker than before and the fucking I was receiving was more direct and lustful, Kyle was getting close. Then he slammed into my ass and held himself against me, I could almost feel the throbbing inside me as he came.

Kyle wrapped his arms around me and we rolled onto our sides and just laid there, savoring the moment.

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AnonymousAnonymousover 3 years ago
Excellent Story

I wish to read more of these two characters. With Kyle being an owner of a Athletic center he would have no problems with getting pills. Kyle should impose that he/she start tacking some of his vitamins only to be feeding hormones to make him/her more feminine and able to grow breasts instead of trying to cope with trying to make something that looks close to being breasts.

Riki1942Riki1942over 3 years ago
Cumming While Soft

I usually only go out fully dressed as a woman if it's with my boyfriend. I want to look like a woman but for some reason, when I'm with him, being "made" by others and knowing that they know we are a couple turns me on.

When we fuck, I am always hard until I cum the first time. I usually have an orgasm pretty fast, unless I slow him down when I'm getting close. If I go ahead and let it happen quickly, he can fuck me long enough that I will cum again even if I have gone soft.

It's a strange, but good, feeling when I cum while soft without my cock being touched. It's a sort of an electric vibrating in my cock and it produces a lot of more clear precum that drools out, rather than white cum shooting out. I call it an anal orgasm where my whole body spasms and my sphincter goes crazy clenching down on his cock!

Riki

4yourpleasureiam4yourpleasureiamover 4 years ago
I added you as a favorit author

Because of your tenderness and love.

4yourpleasureiam4yourpleasureiamover 4 years ago
Another nice tender love story

I do wish my Motorcycle rider had a chance to make me his real girlfriend for a weekend or however long he wanted. I love wearing a skirt and feeling the fresh air blowing up my legs. His hand sneaking back and sliding up my thigh as I hold on tight.

MissLisaJonesMissLisaJonesalmost 6 years ago
Short but sweet

Lovely story well told.

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