The first time I crossdressed

I was at a small bar one night drinking some beers and a few shots. I was shooting pool with an older gentleman who was in his mid 60's. I was 30. It was getting late and the bar was closing. The man I was shooting pool with (Elliott) said he lived about 5 minutes away and said he had a pool table in his house. He asked me if I'd like to go by his house and shoot some more pool and have some more drinks. He seemed nice so I said yes and folloed him to his place. He was a widower and said his wife passed away a few years ago. We shot a few more games and had a few more beers and just talked in general. At one point he asked me how I stay so slim. I'm 5'9", 140 pounds. I told him I was always thin and my job consisted of alot of walking. He said I had a very sexy body. I blushed and said thank you. We sat down and continued to talk. I told him I was married and had a small c***d at home. We kept drinking and talking. He brought up my body again. Normally I would have been uncomfortable but with all the drinking I was relaxed and didn't care. He asked me if I was ever with a man sexually. I told him when I was a teenager I fooled around a little with a friend but that was it. Then he asked me if I had ever worn any womans clothing. I sad no and laughed. He said you have a very sexy body, I'd bet you'd look really good dressed up. I laughed again and tried to change the subject but that wasn't gonna happen. He asked me if I would dress up for him. I asked if he was serious and he said he was. Would you he asked? I felt kinda weird and said I guess I would try anything once. He said he had some clothes upstairs in his bedroom that would fit m and said come on let's go upstairs. I got kinda excited about the thought of dressing. We went into his bedroom ad he walked over to his dresser. He opened up the bottom drawer and it was full of lingerie. He opened anoher drawer and there were a few pairs of high heels in there. Then he opened his closet door and there were some mini dresses hanging there. I asked him who's stuff was this and he said it was his wifes who had died. He said to me, I'd really like to dress you if you don't mind? I was really getting turned on looking at all the clothes and said sure, let's do this. If was hadn't been drinking I don't think it would of happened, but between the beer and him being very nice it made it easier. Plus I was turned on by it. Let's get you out of those man clothes he said. I took off all my clothes until I was naked and sat on the bed. He took out of the drawers what he wanted me to wear. You'll look sexy n all black lingerie he said as he layed everything on the bed. Then he started to dress me. First I put on a pair of lace toppoed thigh high stockings. As I slipped them on I could feel the tingling sensation in my cock. They felt so smooth on my legs. He told me to stand up and up and put a lacy garterbelt on me. He attached the garters to my stockings. There was a full length mirror so I could see how I looked. He said Miki, your legs are so sexy. I had to agree, they really did look sexy. Then he handed me a pair of sexy panties and I slipped them on. Then he handed me a bra and hooked it in the back for me. He had a pair of 5" spiked black heels and they fit me perfect. Then he went into his closet nf pulled out a long sleeved Leopard minidress. It fit very snug and the hem was right above the top of my stockings. He then handed me a back longhaired wig. He said stand up Miki, let's have a look at you. I couldn't believe what I saw in that mirror. I looked so hot. He said Miki you're so sexy. I tried to walk in the high heels but I couldent. I felt so sexy and I was so turned on that the pantys I was wearing were wet in front from my pre cum. How do you feel he asked? I feel wonderful Elliott. You look fabulous. He said, come on lets go downstairs and talk. I took off the heels because there was no way I was walking in them let alone down a set of stairs. When we got to the living room I sat on the couch and put the heels back on. Let me get you another beer Miki he said and went to the kitchen. He returned with a beer for me and one for him. We sat there and talked. He showed me how to sit like a woman with my legs crossed. Then he asked me, Miki, wuld you have sex with me dressed as you are? I blushed and said yes Elliott, I would love to. I'm kinda shy and embarassed though. He said, don't worry baby you're doing fine. Just go with my lead. So, I did. He sat close to me and leaned in close and kissed me on my lips very gently. He put his hand on my waist then slid it to the top of my thigh. His fingers played with the lacy top of my stocking. He kissed my neck and then the top of my shoulder. As he did he pulled me closer to him. I felt his hands all over my body. I was so horny. I don't think I was ever as horny as I was at that moment. I felt his hand move under my dress until he found my clitty which was soaked in my panties with pre cum. He rubbed my clitty and balls though the silky panties and I was in heaven. Then he reached around and grabbed my ass. Sit on daddys lap Miki, he said. I did. He continued to kiss me and feel me up. My God this was so intense. Miki, he asked, would you be a good girl and suck daddys cock? Yes daddy I said. Get on your knees in front of daddy. I did. I undid his pants and slid down them and his underware. His cock was huge. At least 9" cut and it was hard and throbbing. He said, look at me Miki, while you suck on daddy I'm going to pussy all loosened up ok? Yes daddy I said. I leaned down and kissed the tip of his cock. I licked off his pre cum and then licked his cock like a lolly pop. As I did so I felt him pull my panties to the side. I heard him in the drawer in the coffee table. He had 3 butt plugs and some liquid lube. He lubed is finger and then I could feel it it rubbing my pussy. The lube was so slippery. He put his finger against my hole and made circles. That felt so good. I sucked him as he was doing this. Then i felt the tip of his finger push in. He told me the lube hes was useing was made to numb my pussy. Then I felt his finger slide in slowly. He kept it in there for a while then pulled it out. He asked how it felt. I just moaned with my aproval as I sucked him. Then he lubed up the 1st butt plug. It was thin and bout the size of my thumb. He slid it in till it was all the way inside me and left it there. He slapped my ass and that felt sooooo good. After about 15 minutes he pulled out the butt plug. He took the 2nd one and repeated what he did with the 1st one. My hole was numb and there was no pain. He periodcally slapped my ass cheeks. The tingling sensation felt so good. I continued to kiss, lick and suck his beautiful cock. After another 15 minutes he pulled the 2nd butt plug out and put 2fingers inside me and finger fucked me. Then the the 3rd and last butt plug was put inside my pussy. It was the biggest of the 3. It felt really good inside me. Agaid he slapped my ass and it drove me insane. After 30 or so minutes he said, Ok Miki, are you ready for daddys cock? Yes daddy I said. How bad do you want it Miki? Very bad daddy I said. OK baby you're gonna get it. And he pulled the 3rd butt plug from my pussy. Get on all fours baby he said. I did. He got behind me and pulled my panties down. He slapped each ass cheek really hard. Then I felt him hike up my minidress to the middle of my back. I felt him behind me he rubbed the head of his cock against my hole and stayed there. Then I felt his hands on my hips. He pulled my bosy onto his hard throbbing cock. He put it inside me very very slow. A little at a time till he was all the way inside me. I felt stuffed. It felt so good and there was no pain because my hole was numb, but I could feel him inside me. He stayed all the way in and leaned down to kiss my neck and ear lobes. Then I felt him start to pull outtill he was almost all the way out then he would slid back in very slowly. He did this over and over. Then he picked up the pace and got faster and faster. I looked down at my clitty and it was hard and pre cum was dripping out. My balls were tight. His hands were tight on my hips and he was fucking me hard and fast. The feeling was so intense. Then I felt myself cumming and my muscles in my pussy tightened hard around his cock as I came hands free. I heard him moan and groan and he exploded his hot cum in my pussy. When he pulled out I stayed in that position and felt his cum leaking from my pussy down onto my balls. I was exhausted. It was the best sex I ever had. He picked me up and I sat on his lap and we kissed and cuddled. Then we went back upstairs and I undressed and cleaned up in his bathroom. I got dressed in my regular clothes and we went back downstairs and talked some more. He asked me if I would be interested in being his regular girl. I said yes. We met once a week. This went on for two years until he retired and moved to california. That night I was hooked. It was twenty years ago and I still dress to this day. This was a true story. Hope you liked it.