First Crossdressing Encounter

I was so excited that you had finally agreed that we could be together the way I had asked. We had many long discussions about why I loved to crossdress as a woman after the first time you found out. I wasn’t sure I was ever going to be able to explain to you that I wasn’t gay, and didn’t want to be a woman, and that I just loved the sexiness and femininity of dressing in womens clothes, and making myself up. In the end you had proven just how open minded you were, and how much you loved me, by agreeing to spend the night with me.

To give me plenty of time to prepare, you agreed to give me the entire afternoon alone at home. We didn’t speak much that morning, nervous about what lay ahead for us that night, and you left at noon with a quick kiss. As you got into your car, carrying your bag, I called out to you, saying that I loved you, and you replied, saying you loved me. I wondered how long it would take for you to find the surprise I had stashed in your bag this morning.

I went upstairs in our house, more nervous than I ever had in our time together. I knew I would easily consume the hours given to me to prepare, so I wasted no time in starting. I turned on the shower, and simply stood in the hot water for a few minutes. As I had only done only a few times before, I painstakingly began to shave. I took every caution to make sure not to cut or nick myself as I shaved my face, armpits, legs, and finally most of the area around my genitals. I washed thoroughly, rinsed under the hot water, and got out of the shower. Like I only did when dressing, I wore your short, black, satin robe after my shower.

Next I moved on to one of the sexiest parts of crossdressing for me, and one I never seemed to have enough time for before now. I sat down in front of the mirror on your dresser, and opened up my makeup bag. I removed all the makeup I would need for the night, and placed it on your dresser. I started by moisturizing my face, and then applying a good foundation. I felt myself getting more and more excited the more I thought about how great I might look, and what the rest of the night held for us. Putting on makeup always gets me very excited, and tonight was no different. I had to squeeze my legs together in excitement as I put on a nice dark eyeliner, mascara, and eye shadow, and finally some blush for my cheeks. I finished with a good layer of sexy lipstick in a deep maroon. I admired myself in the mirror, and felt I was well on my way to showing you how great I look as a woman.

Next I got my black wig out of the closet where I kept all my feminine materials. I took care to brush out the wig just right before sitting again and putting the wig on. Another few brushes, and I was all set. I decided that before going any further I should dress, so I went back to the closet to get my outfit for the night. I decided that for our first time together I shouldn’t come off too slutty, so I chose my professional white suit, which I thought looked great on me anyway. I hung up my suit on the inside of the closet door, and got out my undergarments for the night.

Since I was wearing a white outfit, then only white underwear would do, but I chose my sexiest lingerie for tonight. I placed my white thigh-high stockings, the white panties, and white corset on the bed. Last I retrieved my white patent leather high heels from the closet. As I looked at my outfit laid out for me on the bed, I was so excited again, and it was all I could do to stop myself from stroking my stiffening cock. As I always did, I started with my favorites, and pulled the stockings up my smooth legs. I love the way my muscular legs look in stockings, and I love the feel of the rubber tops of the stockings, gripping my legs to stay on tight. Next I sat to put on my heels. There’s nothing like the feeling of squeezing my feet into the beautiful leather shoes, and buckling the thin ankle strap. Just like the other times I’ve dressed, I had to walk around a little to get the feeling for the high heels again, but I loved the feeling of being so tall and admired the look of my legs and feet in the mirror.

Next I spent the time to put on my white satin corset and lace it up tight to give myself the hourglass figure of a real woman. After I was fully laced in, I padded the bust of the corset to give myself a womanly looking set of breasts. Finally, I attached the garters of the corset to my stockings, and slid the panties up over the garters, knowing I’d want to take the panties off later, and not deal with the straps. Again I admired myself in the mirror, and I thought I truly looked delicious.

Putting my robe back on, I sat again at your dresser for the next step of my transformation for the night. I patiently went through the process of gluing fake long fingernails on, all the time thinking about how they might feel running down your back. When the nails were firmly glued on, I applied a coat of polish to match my lipstick, and waited for them to dry.

After my nails were dry, it was time to finish dressing. I checked the clock, and the time you would be home was quickly approaching. I knew I’d need this time to make myself just right for you, so I was glad to have it. Hanging the robe back in your closet, I slipped myself into the short skirt of my suit, and put on the white satin blouse for underneath my jacket, and then finally the jacket itself. I watched myself in the mirror, and marveled at the way the corset gave me the right shape to make the suit follow my curves. The final touch of my outfit was a multi-strand pearl bracelet and a matching pearl choker.

I barely had time for a last check in the mirror as your car pulled in the driveway. I went slowly down the stairs as my heart beat a million times a minute, nervous about this important night. I stood in the kitchen as you came through the front door, and I could instantly see you had spent some time getting ready for tonight as well. You looked stunning as always, and wore an incredibly sexy outfit. I couldn't wait to find out what was underneath your tight black miniskirt and black satin blouse. Your legs and feet looked so sexy in the black stockings and high heels you wore, and your face was glowingly made up.

Still unbelievably nervous, I walked over to you, and you did look a little stunned at how I looked, but you covered it well, telling me that I looked great. You remarked on how well my clothes fit, and on how confidently sexy I looked being so tall in my 4" high heels. I did a full turn for you to get a good look at me and I hoped that you were as impressed as you said you were. I think both of our nerves were starting to calm, and I began to believe we truly would have a good night together.

Since it was early in the evening, I suggested that we sit and have dinner and a glass of wine. We walked together to the dining room, and you mentioned that you might feel strange referring to me by my real name. I suggested that you just call me Kira, and you agreed. We sat at the dining room table where I brought out a light dinner of salad and white wine.

I'm sure we made an interesting pair, sitting and eating, like girls out on a first date. It was wonderful to talk while we ate, though, sharing stories of shopping, make up, and our preparations for the night. As we only got more and more comfortable with each other, we laughed and flirted as we ate. After our small salad and a first glass of wine, I cleared the table, and you said you wanted to freshen up in the bathroom. Because you left the door open, I could see you were just fixing your make up and lipstick, and took the opportunity to join you. You looked at me a little strangely while I powdered my face and reapplied my lipstick, but smiled at me when I had finished.

I suggested that we have another wine, and sit and talk some more. We sat on our couch and sipped wine, both with our legs crossed, only proper in our short skirts. I could see that you were definitely starting to enjoy the fantasy we were acting out, and started asking me more personal questions. You asked if I was attracted to you, and I replied with an enthusiastic yes. I told you that this was my first date, and I was very excited, but also very nervous. You put your hand on my thigh, and told me not to worry. Putting your wine glass down, you broke the sexual ice by asking if you could kiss me. I said yes, and you leaned in closer to me for our first kiss.

We started lightly, but our kiss finally became more passionate and intense. You moved closer to me on the couch, and commented on how this was the first time you had ever kissed any girl, and you told me how much you loved our lipstick to lipstick kisses. You kissed me again, hard and passionate, and our tongues met as we kissed. Your lips were incredible, and I could feel the heat of your body next to me. You asked if we could go upstairs to the bedroom, and I readily agreed.

We held hands as I led you up the stairs to the bedroom, where I had already lit a number of candles to light the room. Turning to you as I entered the room, we finally could get our bodies close together as we kissed. Your hands roamed across my back, and down across my ass as we kissed. Your tongue was insistently pushing against mine as we kissed, and when we stopped your face was flushed.

You told me to sit on the bed, and I did, while you walked back to the door, and retrieved your purse from the floor where you had dropped it. You sat next to me on the bed, and with another little kiss, you told me how attracted to me you were, and wondered if I wanted to share a little present someone had given you. Quietly you pulled a velvet bag from your purse, and opened it. Reaching into the bag, you pulled out my secret gift, and showed me the strap on dildo I had given you. I kissed you again, and suggested that we could both make love like a woman and a man tonight, if that is what you wanted.

Standing, you told me you wanted me to watch you undress a little, so I watched you, sitting cross legged on the bed. You stood in the candlelight and started unbuttoning your blouse. I watched silently as you completely unbuttoned your blouse, and I could see that you were wearing a black lace bustier underneath. You took the blouse off entirely, and then started removing your skirt, never losing eye contact with me. When your skirt fell to the floor, I could see that you weren't wearing any panties, and I squeezed my legs in excitement at how beautiful you looked in just the bustier and black thigh high stockings. Still in your high heels, you grabbed the dildo from beside me, and quickly buckled it around your hips. It looked perfect, just as I had hoped, because it gave you a great, large hard on, but left your pussy and ass completely exposed.

When you asked how I thought you looked, I said you were gorgeous, and stood to give you another kiss. We held each other in our arms, and I could feel your hard on against my crotch as we kissed and fondled some more. While you caressed my breasts, ass, and crotch, I did the same, and loved the feeling of being able to touch both your mound and the hard dildo you were wearing. We stopped our kiss, and you asked me to undress for you, which I quickly agreed to do.

While you continued to stand, I knelt on the bed facing you, and began to undress. I unbuttoned my suit jacket, and quickly removed it. Next came my white blouse, and I could see you loved seeing the corset I wore underneath. Next I unzipped my skirt, but lay on my back to remove it. I watched you while I slowly slid the skirt off, and I could see that while you watched me, you had one hand rubbing your breasts and the other alternating between rubbing your pussy and stroking your dildo. Now, down to my heels, jewelry, and underwear, I was truly excited, and I couldnt wait to make love to you. I decided I could give you a little show, and began to run my hands all over myself. I could tell you were excited as I stared into your eyes, and slowly touched my breasts, and ran my hands down between my legs. I stroked myself while you watched, all the time touching yourself ever so lightly.

Finally, you came and lay down on the bed next to me, and we kissed and touched each other more. Before long your hand was at my crotch, stroking my cock, and I touched you between your legs as well, feeling your wetness. Next you decided you wanted my panties off, and you pulled them down and off my legs. Again we went back to kissing and rolling on the bed, both of us just enjoying the feeling of a hard cock rubbing our crotches and asses as we rolled around.

I want to start to make love to you, so I got you on your back, and kissed my way down your stomach and settled in between your spread legs. In anticipation, you watched as I kissed down both of your hips, and finally took your cock in my hand. I hoped you liked seeing my long fingernails wrapped around your cock as I placed two or three kisses up the length of your hot pussy. I whispered to you that I had been hoping to suck your cock all day, and now finally the time was here. I let you watch as I started kissing and licking the length of the dildo, and looked straight into your eyes as I took the cock into my mouth. I loved the feeling of the hard cock sliding in and out of my mouth, and across my tongue. I only hoped you enjoyed watching me as much as I loved making love to the fake cock you wore.

Soon you wanted to get into the action, and rolled me onto my back. Just the way I love, you straddled my head so that I could continue to lick you as you went down on me. It felt wonderful to have my cock sliding in your mouth, and I took the opportunity to start licking your hot pussy. I was sure we made a beautiful image, two girls in their lingerie, stocking, and heels, locked in a 69 with a couple of hard cocks and hot mouths between us.

After only a quick minute of your oral attack on me, I felt you slowly push your wet finger into my ass, and I told you how good it felt to have your finger pump me while you sucked my cock. I continued to lick your wet pussy while you sucked me and probed my ass with your finger. You rolled off of me, and asked if you could be the first one of us to get a hard codk inside you, and I agreed. I snuggled up behind you while you lay on your side, and rubbed my cock up and down the crack of your ass, and then pushed my cock into your pussy.

You felt great as I pumped my cock in and out of your pussy, and kissed your lips while I held you. You were so hot and really moved your ass back against me while I pumped in and out of you. While I fucked you, I was touching you all over, and I loved to squeeze your breasts and hard nipples. I wanted you to have a great orgasm, so I grabbed one of your own hands , and moved it down to grasp the dildo sticking out from your hips. Together, with our painted fingernails entwined, we stroked the cock before moving down to rub your pussy. With both of our hands we rubbed your wet pussy lips and clitoris, soon bringing you to a moaning orgasm.

After resting for a short minute, I whispered in your ear, and asked if it was time for me to get fucked like you had. You said of course, and I slipped my cock out of your pussy, and rolled onto my back. I told you that there was lubricant in the bedside table, and you reached over to retrieve it. Again I had the chance to admire just how beautiful and sexy you were in your lingerie and strap on cock. I whispered to you that I couldn't wait to have you inside me, and I put a pillow under my ass to prop up my hips. I watched as you rubbed the slick lubricant across the dildo, and then look at me, asking if I was ready. I replied by lifting my legs up, well spread, and exposed my ass to you.

You rubbed some of the extra lubricant across my ass, and made sure I was ready by again putting a single finger inside my ass. I held me legs up and open as you reached down and grabbed the dildo, and placed the head against my ass. I tried to sexily tell you to fuck me, and you smiled as you pushed your hips forward, and pushed the head of the dildo inside me. I gasped a little at the fullness I felt with the big cock inside me, but I told you how great it felt, and I told you to push it all inside me. You did, and soon you were pumping me with the fake cock so well, and I loved every second of the feeling.

My cock was harder than ever and I was so excited by the feeling of your strap on sliding in and out of me. I talked dirty to you, telling you to fuck me and telling you what a good little slut I was for taking your cock in my ass. I could tell that the dirty talk was making you hot, because you fucked me with harder and harder strokes. Finally, sensing I was ready to cum you began stroking my hard cock while you continued to pump me with the dildo. After just a few strokes, I was moaning and lifting my hips, and then finally cried out as I came, my sperm jetting out onto my stomach.

Pulling the dildo out of my ass, you bent over and noisily slurped my cum up into your mouth, and then lay on top of me. Our lips met and you stuck your tongue into my mouth, and we shared the taste of my cum in our mouths. We continued our sticky french kiss until we had swallowed all of my cum, and then I looked into your beautiful eyes and thanked you for making love to me like a woman.

The End