First Time With A Man

I have crossdressed for a long time, actually, as long as I can remember. I had some time off last winter, so one day when I was all dressed up, I got online and was looking for a special friend. It didn't take long and I had all sorts of invitations to play. After talking with an older married gentleman, I very nervously gave him my address. I had never been with a man, and at that point had been married for 26 years. Yes she knew I dressed, but has no interest in it at all. I guess if ignores it, she thinks it will go away. Anyway, I was all dressed up, white lace panties and matching bra, white lace garter belt, with white silk stockings. Over that, I had a pink knee high tight skirt and a light pink turtleneck sweater on, and of course, pink 4" heels. I had already prepared for possible intercourse with plenty of cleansing. I was feeling hot, sexy, and as nervous as I have ever been. I was actually shaking. Other than my wife, no one had seen me dressed. Within a half hour, there was a knock at my door, now my nervousness was really in full gear. I was really going to do this. I peaked out the window to make sure it was him, and it was. Slowly I made my way down the steps to the door, women, you make it look so easy walking in high heels! I opened the door slightly, and peered around the door, he whisppered, kattie? I answered yes, come on in. I opened the door and he quickly slid in. Now I stood before a man completly dressed in womens clothing. He looked me up and down, and smilled. I lead him downstairs to my basement, where we sat on the couch and exchanged pleasantries. After a short time, he had already known I wanted to be taken complete controll of, he just leaned into me, grabbed my head, pulled it to him, and gave me the deepest wettest kiss I have ever had. I just melted into his arms. Before long, his hands where exploring my body, under my sweater, feeling my hand nipples thru my bra, and under my skirt between my legs. I didn't fight any off it,and actually spread my legs a little so he could feel the softness of my pantie clad crotch. I had done the "tuck" so there where no real big buldges at that time. I was softly moaning by now, and eagerly accepted his advances. Then with no warning, the time came for me to show my womanly side, he grabbed my head and gently pushed it towards his crotch. I knew what he wanted, and began to shake almost uncontrolably. I undid his belt, then his zipper, and slid his pants the the floor. Now I was face to face with his now hard ****. I remember saying softly, "O my God", before I took him in my mouth. I couldn't believe how warm it was in my mouth. Soon, I was sucking him like a pro. My head bobbing up and down, sucking, licking, chocking sometimes as he tried to push it farther in. I couldn't believe I was sucking another man's ****. After a while, he was moaning and trying to push harder into my mouth, and I could actually feel him swelling up. I knew what this meant. Then, just when I was ready to take his hot load, he pulled out, and told me to stand up, which I quickly obeyed. He stoop up, turned me around, and pushed me by the head face down over the arm of the couch. I felt him pull my skirt over my waiste, the him pulling my panties down around my knees. My head was spinning like a top. He then pushed a finger deep into me, I moaned out loud. I have had things inside of me, but, never anything real. I was already wet and lubed from playing a little before he came over. Then a second finger, in and out he slid them with ease, I was deleareous now excitement. Then I felt him pull his fingers from me, next I knew his warm **** was pushing at my opening. He thrust forward and deep into me all at once. I moaned out loud this time as I felt him deep in me. Another mans **** was inside of me! He held it there for a couple of seconds, then started a slow rythemic pumping. His strong hands held me tightly around my waiste as he started to really pound into me. I could hear and feel his swollen balls slapping against my *** as he did. My God I never imagined it would feel this good! All my fantasys where coming true. I was all dressed up, and was a man's little *****. By now I was pushing back into him matching his thrusts. He reached up, grabbed my hair, and asked , you like that *****? All I could do is nod my head yes. With that, he slapped my *** hard, and in a louder voice, i asked you a question *****. This time I managed to get, yes sir out for him to hear. He answered good. I don't know how long he was pounding away at me, but, then I felt him getting tighter and tighter inside of me, he was swelling and ready to ***. Then I felt him stop, grab me tighter, and in a loud grunt, exploded inside of me! I could feel the warmth of his *** gushing inside of me, all I could do was stand there and let him *** inside. I remember I had a huge smile on my face as I stood there letting him fill me up with his hot ***, and how it felt, I was in heaven, and as close to being a woman that day as any I have had dressing up. Him and I meet on a regular basis now, and I still love it.
kattie2121 kattie2121
56-60, M
4 Responses Jun 10, 2013

wonderful. thanks for sharing :)

I relaay like your story I wasn't to in touch with hs asty comment o you but what happened happened. I would have wshed he were efem as well and you both could have had some very sexy cd love.

Wonderful story, Kattie. You got me rock hard and ************ to completion while reading. Very hot!

OMG... how sexy.