I had been talking with Olivia online for a while now and it looked like our "relationship" was progressing nicely. As a cross dresser I had not been attracted to other "CD's" but there was something about her when we talked. Then I saw her pictures and WOW! Olivia is my height 5'7" but a little heavier than my slight 140lbs. She is not fat at all, just a stronger body than mine. I drool over the pictures of her wearing all sorts of sexy clothes, and her long black and red wig gets me hard. She has said that my pictures were nice and "yummy" as well. Some of her best are pictures of her sucking on cocks. God I love the way her lips look wrapped around a nice hard dick! Like it was meant to be there and fits perfect. She had never done anything other than oral with guys so I was very much looking forward to changing that. I wanted her hot cock buried deep inside of me and a chance to show her how good it is to have a hot CD sucking on her cock.
We had made plans to meet up at her home. I was very excited as I got myself ready. After showing and shaving my body smooth I sat and began doing my make up. I put on my foundation and began with my eyes. Heavy eye liner and dramatic eye lashes. I then put on sexy purple eye shadow and a bit of blush. My nails were the same purple metallic as my eyes. I finished it off with some dark lipstick and a few sprays of perfume. Next I put on my blonde bob wig and my silver choker. I looked in the mirror and was very happy with my results. I felt very hot as I touched my pierced nipples and belly. Ok no time for that, I walked over to my jewelry box and put on my rings and large hoop earrings. Feeling sexier by the minute I began to dress. Since Olivia was a bit darker than me, almost a Goth look I wanted to go with the pure, innocent look. I rolled my white stay up stockings with seam up the back onto my smooth legs and attached my ankle bracelet. Next I put on my white halter corset and tied it really tight. It really gives me a sexy hour glass shape. I attached the garter straps to my stockings and then pulled up my boy shorts. I love these as they have little open sides. I struggled to decide what to wear over my sexy outfit. I decided on a tight short white skirt and tight purple blouse. It is very sexy but not over the top like I usually do. I slid into my 4" patent white Oxford heels before making one last check in the mirror. I must admit I looked hot and was ready to meet Olivia. I grabbed my purse complete with essentials, grabbed my keys and was out the door.
I arrived at Olivia's house a short time later. Nervous and excited I stepped from my car dressed as a sexy woman. I walked up to the door being aware of my stride. I wanted to walk as sexy as I could. I took a deep breath as I tapped on the door, I heard shuffling inside and soon the door opened. There stood Olivia, and man did she look HOT! She was dressed in a black skirt and white blouse, her large erect nipples poking through the sheer material. Her sexy legs covered in black stockings and feet placed in high stilettos with metal heel. I couldn't take my eyes off of her as she invited me in. We sat on the sofa where two glasses of wine were set. Soft music played and she had some sweet incense burning along with an array of candles. It was a very sultry atmosphere and I felt lucky to be invited into it. We chatted for a while making small talk. As we talked our eyes occasionally broke gaze, surveying the others body. The conversation was natural and not forced as you might expect it to be.
As the wine flowed our hands began to roam, first touching stocking covered legs or hands and up arms. This slow progression was more like a couple of high school girls experimenting, not grown men who have each sucked cock, but it was. It was slow and deliberate. Then it happened, a long pause in conversation where we just smiled and looked at each other. We leaned in and our lips touched sending a wave of pleasure throughout my body. Olivia's tongue danced with mine as our lips remained locked. I moaned into her mouth as her hands pressed and rubbed against my nipples. My own hands wandered down and began working the buttons of her blouse. One by one I exposed her lingerie covered body. She had on a sexy black bra and waist cincher. Our kiss was becoming more heated and more intense. My own shirt was being removed as her mouth licked and sucked at my chest and shoulders. I stood up and pulled at the zipper of my skirt letting it fall to the floor, then stepping from it still in my sexy high heeled Oxfords.
Olivia put her hands on my tight firm ass and pulled me to her as she sat on the edge of the sofa. Her mouth went to my stiff cock and she began to lick and nuzzle me through the sheer material of my panties. Her hands found the waist of my boy shorts and she pulled them down. There I was standing in her living room with my hard cock just inches from her beautiful face, ready to have my cock sucked by another man for the first time. Only this was even better because the guy that was going to do it was a super hot cross dresser. She took my cock in her hand and curled her fingers around it. The sexy French manicured finger tips contrasting the skin of my hard dick. She pressed her lips to my mushroom cock head and extended her tongue. I was in heaven as that tongue began to lick all around my head and up and down my shaft. She moaned as she licked which increased the erotic feeling I was already experiencing. Then like before she pressed my cock head to her lips, this time allowing me to penetrate her mouth. Her soft lips molded around me as I slid further into her. It was such a wonderful feeling as my cock went to the back of her throat and then pulled back out. She slowly rubbed my shaft as she continued to lick. My hands found her head and I held tight as I ran my fingers through her hair. Olivia's mouth sliding over my cock was brining me close to my climax. Not wanting to cum just yet I pulled my hard rod from her mouth. A line of pre-cum stuck to her mouth and finally gave way.
I got to my knees and pulled at her skirt. I licked up her leg as I tugged at the side of her panties freeing her cock. It was beautiful and I could not wait to have it in my mouth and then in my ass. I quickly dove onto her cock and drove it deep into my mouth. I was a horny slut and wanted it all. My mouth moved quickly up and down on her shaft, allowing her to fuck my mouth. I regained my composure after a good while of her fucking my face and began to explore and lick. As my tongue was going over every inch of that hot cock I looked into her eyes. She was looking back at me as she rubbed her hands over her body. My mouth would slide down her cock and then lick and suck her balls for a while before going back up her shaft. All the while I was jacking it with my hand. Her cock was very wet from my spit and ready to go into my ass. I was ready for it to go into my ass.
I gave her a few more soft licks before standing up. I grabbed my purse and pulled out my lube putting a generous amount on her cock. I then began rubbing it into my ass as I stood in front of Olivia who remained on the sofa. As she sat I climbed onto her lap and held her cock in my hands. My own cock sticking straight out as I slowly lowered myself onto her. A soft moan escaped my lips as she entered me; Olivia closed her eyes as inch by inch she filled me up. I was now fully seated on her cock as I began to rock up and down on her. We kissed as my hands supported myself on her shoulders; hers placed firmly on my waist. She would move them up feeling the fabric of my corset before falling back to my waist. Her cock sliding in and out of me put the perfect pressure on my prostate and I knew I was close to cumming. God I loved it when I came from being fucked in my ass. Olivia closed her eyes and increased her tempo of her thrusts into me. I was feeling like such a sexy slut and slammed my ass back down to meet her. My cock was bouncing up and down with our motion. Suddenly I began to shoot my hot sticky load onto Olivia's chest. Stray shots went over her shoulder and one landed on her lips. She extended her tongue and licked her lips clean. My ass squeezed tight as my orgasm continued sending Olivia into ecstasy. She grabbed my ass hard and pulled me down onto her as she began to shoot inside of me. Her cock was pumping her seed deep into me as I moaned out. My own cock had since subsided but this did not quench my thirst for her. I put my mouth on hers and shoved my tongue deep into her. We kissed as her cock twitched and spewed its final drops. I settled into her as she held my ass tight. Our lips locked and her body coved in my cum. My ass filled with her cock and cum. Our kiss broke and we just looked into each others eyes.