Genny

I am a widower and have always liked wearing my wifes clothes. However I never went out in public until now.
Last night I got the urge to go out to a club that is open to cross dressers. I shaved my body and put on a pair of tight panties, panty hose and a pushup bra. I wore a sexy blouse and a pair of my wifes tight jeans and a pair of her flats. A little makeup and lipstick along with a shoulder length wig completed my “look”. For a “gal” of my age I looked pretty good.
This was my first time out in public and I was a little nervous but when I entered the club no one snickered or pointed at me so I felt at ease. I walked up to the bar and ordered a drink and took it to a small table by the dance floor. Sipping my drink and watching the people dancing put me more at ease. Suddenly I was startled when someone tapped me on the shoulder. To my suprise a gentleman who I had talked to several times at the pier where I sometimes fished asked me to dance. Did he know who I was? What should I do? He said should I call you James tonight or do you go by something else when you’re out on the town? I replied with “You can call me Genny” He said great and then he said I looked “hot” and he took me by the hand and led me to the floor and danced a slow one holding me close to him. After we danced he bought me another drink and we talked about my second life. I told him this was the first time I was out in public and found it exciting. After a few more drinks and more talk we decided to go get something to eat. I was hesitant at first because a restaurant is brighter than a dimly lit club and that someone I knew might see me. Well we went, ate and no one I knew saw me. I had a little too much to drink and didn’t want to take a chance driving and getting caught “dressed up” so Don said he’d drive me home. I agreed. So far he hadn’t made any passes at me except to dance with me and that suited me as I’m not gay by any means of the word. Well when we got to my house he asked if he could come in and use the bathroom. Of course he could. When he came out he said goodbye and headed to the door. I walked to the door with him and thanked him for a nice evening and that I’d probably see him at the pier on Thursday. All of a sudden he pulled me close to him and kissed me on the mouth. I was shocked but excited. I pulled away and looked at him and again he kissed me but this time he parted my lips and tongued me. I was scared and excited at the same time. Before I knew it he was feeling me all over and I was melting away. Somehow we ended up in my bed. I was being undressed by him and he was kissing and licking me all over. It was awesome. He spread my legs apart and licked my hard shaft and within moments I came all over. He started rubbing my come all over my balls and crack. I didn’t even realize that he had removed his clothes until he lifted my legs and I felt his boner touching my hole and pushing against my tight pucker hole. I told him that I had never done this before and he said he’s going to pop my cherry and all of a sudden he bore down on me with all of his might driving his dick all the way in with me screaming at the top of my lungs. I had never felt such unbearable pain. It felt as if I had a coke bottle up my rear. It seemed like an eternity that he was fucking me with me crying and begging him to take it out of me. All of a sudden he shoved in and out and then he just kept it pushed all the way in me and I felt through the pain his hot cum spurting in me. When he finished he pulled out and said he needed to get home that his wife would be wondering where he was as the pier was closing in twenty minutes. He left without another word and I just layed there in terrible pain cussing myself out for allowing this to happen. After a while I stumbled to the bathroom and sat on the pot to pee because I didn’t have the strength to stand and pee. My ass was burning and I felt like I had to shit so I tried but only his cum was running out or so I thought. It was when I wiped myself that I saw the blood on the paper mixed with his cum. When I woke up this morning the pain was still as bad as last night. My sheets were covered with blood and now almost 24 hours later I’m still bleeding and in pain. A few minutes ago Don called and said he really enjoyed last night and hoped we could get together again soon. He said no one had ever been able to take his 2.5″ diameter dick up the ass before me. I told him to go fuck himself. He didn’t even ask if I was OK. As far as I’m concerned I never do this again. I never realized how unbearable anal fucking really is.

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