Meeting Ken

Through the years, I have a occasionally cross-dressed mainly in the privacy my own home. I mainly put on a garter belt, stockings and sexy panties and look in the mirror to see a pretty women gazing back. I get so turned on I have to please myself with my vibrator and my hand.  

                 

But recently I have wanted to get fully dressed up so I started purchasing all the things I need from Cross-Dress.com to transform me into the little slutty girl I wanted to be. One night when I was alone, I got dressed up and took pictures. My look was just getting started, but I got turned on by the tight pantyhose rubbing my crotch and the long blonde wig caressing the top of my back. I strutted around the room in my high heels and set up my phone camera to capture video of me bending over, exposing my ample ass bouncing up and down and my large silicone tits falling into my hands.

                                                                                        

The next step was to put my pictures on a cross-dressing dating site. I didn’t think i would get too many responses, but to my surprise I got a few! I live in South Florida, and they are on other side of the country, but I did get one a guy named Ken that was local so we started texting back-and-forth. We set up a date to get together. I was trembling at the thought of actually meeting a man. Would he think I was pretty enough? I took a drink and calmed down enough to text him again with, "I can't wait for our date!" with a kissing lips emoji for effect. 

                                                                                            

The day came for our date. We were going to meet at the Holiday Inn, so I started getting dressed. I put my makeup on first, making sure my lips were pouty in red lipstick. Then I put on black panties, a back long sleeve snap crotch teddy and a tight black mini skirt. I slowly pulled on my white fishnet stockings, making sure my legs were perfectly smooth and slipped on my black heels. I finished by applying red press on fingernails and my long blonde wig. I looked at myself in the mirror and thought I look so sexy. I was hoping Ken would think so too. I grabbed my keys and carefully walked to my car, pulling my skirt down just a bit so that my ass cheeks wouldn't show.                                          

 I arrived at the Holiday Inn quickly, went to the lobby up the room 312, the room number Ken reserved for us. There was another man in the elevator and he glanced at my approvingly. I could see that he was looking at my tits straining against my teddy, the nipples always hard. When I got off on the third floor, I walked slowly towards the room, making sure everything was in place and steadying myself for what was to come (in more ways than one!). I knocked on the door and Ken answered the door. He appeared to be in his 50s with a medium build, salt and pepper hair and he smelled wonderful from the cologne he had on. I was getting excited just looking at him through the doorway! He told me "you look good baby!". I felt a rush of relief wash over me that this sexy man could think I looked sexy. I then asked him if he would take some pictures of me in different poses. "Of course I can baby. I want to see what you've got!" He had my pose holding mytits, bending over and also on all fours with my blonde wig falling onto the bed. I was getting turned on posing for him and then Ken walked over to his bag and pulled out a long rubber dildo. He told me he went to see if I could give good head so I crouched down before him and licked my red lips. The dildo must have been 8 inches, but I was feeling confident. I took the rubber dildo in my mouth, inch by inch moaning for more. "You're a pro at sucking cock baby," he said as he pulled the dildo out of my mouth and started taking off his clothes. when he finally got to his underwear, a could see his hard cock straining against them and it was time to let it free! 

When he was fully undressed, he told me to get off my knees and onto the bed. He walked over and got on top of me. He started kissing me and told me how sexy of a woman I was. I then pulled out one of my titties and told him to suck on it which he did and it felt so good. "Are you ready for me baby?" he asked. I was pulsating and felt my lady cock dripping. "Yes Ken, I'm dying to feel you!" I moaned. He then told me to bend over the table. I obliged and he lifted my black mini skirt to expose my waiting hole between my bouncing cheeks. He then put his beautiful slick cock in my pussy hole and let out a moan. I felt so good that my knees got weak and I asked him to go slow since his cock was long and I had only ever had a dildo in my hole before. He slowly thrust his cock little  by little. I just wanted to scream with delight! I was so tight that I couldn’t take his whole length the first time. "It's ok baby, there are other ways you can please me until we get that tight little ass of yours stretched for my full length."  So Ken pulled his cock out of my throbbing hole and instructed me to put the dildo in my mouth to get it wet then up put in his ass. "Get on your knees now and suck me off." I was happy to oblige. I took his hot cock into my hand then guided it into my mouth. I felt the head throbbing and made quick work of licking and sucking him while cupping his hard balls in my hands. I kept this up until I heard him moan and say "I'm going to blow baby. Are you ready?" I looked up at him and nodded while thrusting his cock in and out of my mouth. Less than a minute later, he yelled out, "I'm cumming baby!" and he blew his hot load into my waiting mouth. I felt the cum dripping down my chin and his cock start to get soft. Ken then instructed me to get onto the bed and put the dildo into my own pussy ass. I crawled to the bed and got the dildo wet with my spit and inserted it into my ass. He then told my to fondle myself until I came while he watched. I moved my teddy over to expose my pulsating little cock while making sure to keep the dildo moving in and out. I was so turned on that it took no time for me to blow. When I was done, Ken came over and kissed me. "You did good baby" he said and he got up to get dressed. He was so kind and I knew that we would be meeting again soon.