Little backstory first. I was blackmailed into coming out to a family member from an ex friend. I had quit dressing for 5 years cause of my living situation. When I told that family member they said just don't run around in bra and panties in the living room.
So I started buying panties and teddies again. I started wearing them every day. I only wore them in my room I wouldn't even wear them in the common areas because I was nervous one roommate who was big time anti-any alt life style would see them under my shorts.
Finally one day I got the courage to wear a pair while cooking. Then outside. Then every day.
I ordered a few teddies from Lane Bryant and had them shipped to the store. I went to pick them up and saw a cute skirt, I decided I wanted to try it on so I took it and went to the fitting room. Tried it on and ended up buying it. Here is where the story starts.
I heard "Oh that's cute. Good choice. For your girlfriend?" before I even thought about it "No for me" was my response. I turned and looked at who was talking to me and it was very sexy guy. I knew I was bi long before this but I was instantly turned on by him.
He said (name changed) "Name is Keith" I responded for some reason with "Kim". He looked and said you don't look like a Kim. I said that's my CD name. We chatted a bit and he asked me if I wanted to go get a drink. I told him I don't drink anymore but we could go get coffee and chat. Then I got real brave and said or go back to your place and I can model the skirt and other items I bought. He smiled and said ok.
I don't normally do random hookups like this so I was taking a big chance. I got in his car and said you have to bring me back cause it's not my car and I don't want to take a chance someone sees it and tells the owner where I was. He said ok.
We drove a few blocks from the mall and he pulled into a driveway and said this is me. My heart was beating so fast. It had been about 10 years since I was with another guy. We went inside and I wasted no time. I didn't even get dressed I turned and grabbed his cock and kissed him deeply. I whispered I don't want to waste time modeling we both know what we want. He moaned yes and I unzipped his pants.
I got on my knees and started kissing his hard dick. My heart was about to jump out my chest it felt like. I slide my tounge up and down the shaft then slide my mouth over it. He wasn't huge about six inches so I was able to take his whole cock in my mouth. After about 5 mins or so I felt him twitch and he tried to pull out of my mouth as he said I'm going to cum. I moaned around his cock no and help his hips so he had to cum in my mouth. I went down as far as I could and felt him shoot his cum in the back of my mouth. I swallowed as much as I could only a little fell on my chin. He said most girls won't do that on the first date.
I've been dressing for a long time and nobody called me a girl before and that made me so hot for some reason. I always thought it would bother me to be refered to as a girl.
I stood up and kissed him and said now I will model a teddy for you. Let's go to the bedroom. I went into the bathroom and put on my pink teddy I just picked up. I was already in pink panties so I left them on.
I came out of the bathroom and did a little twirl and said you like what you see? Keith responded you look so sexy Kim. I climbed on the bed and started making out with him. He asked if I wanted him to give me a blowjob and I said no. I want you to get hard again and fuck me. I was playing with him and when I said that he got rock hard right away.
I laid down and spread my legs and said come make me that girl you said I was. Come fuck my pussy. (I never talked like that before it was always fuck my ass never pussy). He slide between my legs and I wrapped them around his waist. He licked a finger and slide it into me to get me a little loose then put the tip at my hole. He started to slide in slowly and I was in heaven. I felt every part of that cock as he entered me. I started to moan. I pulled his mouth to mine and kissed him again and whispered fuck me now. He started going faster as I sucked on his neck.
Since he had already came once he took about a good while to get close again. The whole time I am moaning very very loudly. He asked where I wanted him to cum on me or in me. I said (again taking a risk) in my pussy baby. Deep in there. He moans I'm cumming, So I pulled his hips as hard as I could and felt his cock twitch as he started to cum. I kissed him again as he was cumming then I felt my cock start to twitch and I came.
He said he had to get ready for work since he worked nights so we exchanged numbers and I threw my guy clothes on over my teddy and as I put my panties back on I could feel his cum dripping out my ass. He took me back to my car where we kissed again and said we would hook up again soon.
I drove home and didn't even notice that his cum had dripped down my legs since I was in shorts. The family member I had came out to was sitting in the living room as I came in. I went into my room and then a few minutes later she knocked on my door. I said come in. She stepped in and smiled and said so what's running down your leg. I thought oh shit...And I answered honestly probably the guy who just fucked me cum. She smiled. Did you have a good time? She asked. I said yes. She looked at me like she wanted to ask something but was scared to. I said I won't describe all of it but he fucked my pussy like I was a real girl. She got a weird look and said pussy? I said yes thats what a sissy calls their ass. And that's what I was today a cock hungry sissy. She smiled and said good for you.
And that was the exact moment I decided to dress as much as I could and come out as bi. I had to move to be Kim as much as possible due to the anti-alt roommate but now I can dress as Kim all I want.
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