Originally Posted by
jackbirdjay
I been cross dressing on and off since I was 14. When I was 20 had my first bi experience with a guy in his 50's. About age 22 got my own place. I started dressing going to stores and buying sexy clothes, with stares. It was the 70's early 80's started shaving everywhere. Then at 23 did the whole thing and went out on Halloween, fully dressed. I wore a red dress that was a wrap around, knee length, black stockings with red garters, black thong, black bra, and red heels. Back then I was very skinny, had long hair, and long nails. nails and toes were painted red. A guy started hitting on me. I kept saying it's Halloween you know. He said yes he knows. He was on the drunk side. I finely said to him I was a guy dressed for Halloween. He said his wife doesn't like sex, right now I am so horny anything looks good to me and you did do a good job dressing. I said thank you. He started putting his hand on my leg, rubbing it. I said are you bi? He said no but could be. I pulled my lip stick out of my pocketbook and put more on. His hand was now under my dress on my thigh. I asked him if he every did anything at all with a guy? He said not yet you game? What do you have in mind? He said don't know but thinking for a while now what it would be like. I was scared it was 1980 not as open like now, thinking it might be a set-up. I was also very excited to. After about three more drinks and him almost begging I said you get a motel room we will go. He said ok I'll get a cab. We left in a cab. I reached over pulled him to my mouth and kissed him to see if he was serious or not. He kissed me back deeply. Once in the room we were kissing his hands all over me. I push him back a little and said hold on tiger. I started unbuttoning his shirt taking it off. I dropped to my knees taking his shoes and socks off, I reached up undoing his bet and pants letting them drop to the floor. He had white mens bikini. I reached up pulling his nipples as I kiss his cock though the bikini leaving lip stick on them. All this time he was moaning oh yes. I pulled his bikini off. His cock was only semi hard. It was a good size soft with lots of veins and a few blue ones. His nuts hung very low with one hanging lower than the other. I took him in my mouth sucking and licking playing with his nuts. After about a minute or two he pulled me to my feet. He still wasn't hard just semi. He took my dress off and started rubbing my cock though my thong. He started kissing my neck putting his hand in my thong playing with my now hard cock. He whisper in my ear so this is what jerking another cock is like. He stated grabbing my ass and asked how many guys I been with. I told him 3 tonight, I lied. He pulled my thong down letting fall to the floor, I stepped out of them. Now at this point he still wasn't hard. I asked him if he wanted to go on the bed, he said yes. I said lay on your side. I lay down next to him but in a 69 position. I started sucking him he was just stroking me. I said go ahead lick it but if you don't want to it's ok. He said no he wanted to and then started licking my hard cock. He said nice I think I like precum. He took me in his mouth started sucking and lick me. He still was soft in my mouth. I started sucking his nuts one at a time. I went down further licking just before his ass. He started moaning put one leg up high. I then got on top of him. I slide down to his hairy ass and started tonguing it. He moaned oh yes. My tongue darted in and out. He started getting hard under my chest. I was humping his chest as he was rubbing my ass cheeks. I sat up he said don't stop, I took my bra off and went back. I was licking his ass humping his cock with my smooth chest. He started cumming on my chest. As he was I started sucking and licking his nuts and slide two fingers in him rubbing his sweet spot. After he stopped cumming, I slide down to taste his cum. Licked him clean. He said go sit in that chair. I did as I was told. He came over to me got on his knees told me he was nervous about this but enjoyed it and got on his knees started sucking me. He said don't cum in my mouth not ready for that let me know when your ready I'll jerk you off. I shoot all over his chest. I licked his chest clean keeping it in my mouth. I kissed him giving him a snowball forcing it in him mouth. I said now you know what I taste like. We started a 5 year fling. We would meet, I would be dressed for him.