First off I had a sister that was 3 years older than me. In my freshman year of high school I hit the point I wanted to know what ladies under wear felt like. My sister had a strict no entering her room policy. So the summer after she graduated she went on a two week trip. My parents went to work all day. So the first day she was gone and so were my parents I had my opportunity. I went into her room and opened her drawers. It took me a minute to sort thru the plain cotton ones. The I struck pay dirt. I found the satin underwear I knew she had hidden from Mom. I stood in her room and put those panties on. They were tight but felt so good on my cock. I did this for two weeks straight. It was a great two weeks. Anyway fast forwarding several years.
I just moved into my own place my junior year in college. I was finally on my own. My own computer and everything. I never forgot how good those panties felt. So I decided I needed to buy my own. I found a mall and scoped it out. After going to a few stores I didn't really feel comfortable. I ended up at Sears in the ladies section. I scoped out the lady at the check out. She was an older lady and I figured this was my chance. Not to many other ladies in the section either. Trying to keep a low profile. I walked into the area filled with bras, panties and stockings. I was so nervous. I grabbed some bras and panties and rushed to the nearest dressing room. I grabbed some jeans and a shirt to cover the bras and panties. There was one guy in the dressing room too. I put the panties on and instantly was back in my freshman year in high school. I tried on the bras until I found a well fitting size bra. I knew I needed more of them and more panties too. I covered the bra and panties up and went back for more. I needed to get back into the dressing room to try in a few more things. I went back into the dressing room with another "cover" shirt. When I walked into the dressing room I looked over my shoulder to make sure no one saw me I ran into a guy that was coming out of the dressing room. I ran into hi and dropped my clothes. The bras and panties came out of the cover shirt. I tried to grab them quickly but he saw them. I was so embarrassed. To my surprise he just said "Those are sexy". I said "Thanks". We kinda struck up a conversation now that I figured he was into what I was doing. He said to meet him in the food court of the mall if I wanted to chat more. He gave me his number and I said that I would call him in a bit. He was 40 to 45, really good looking guy. After getting thru my very nervous purchasing the bras, panties and nylon stockings. I was now more nervous about meeting my guy in the food court. I decided to go thru with it. I called him and met him a few minutes later. He bought lunch for me and we found a somewhat secluded table. We made small talk. He told me his name and that I should not be nervous or embarrassed about our earlier encounter. He told me that he would like to talk further but could not really ask me the kind of questions he really wanted to in the food court. He told me he had an apartment close and if I would follow him over there we could chat. He told that if I didn't it would be no problem. I thought for a minute an decided it would be okay. I went to his place with my bag in hand. I had fantasizes about being with a guy before but had never done anything about it. My mind and heart were racing.
Once inside his place he made me very comfortable. We started to chat about my purchases. After some chatting he told me that he wanted to see me in my purchases. Then get me out of those clothes for some fun. I told him I have never been with a man before and that I was a virgin both ways. He said that if at any point we could stop and there would be no problem. He had some porn to lighten the mood. I went into eh bathroom and slipped on a pair of black thigh high stockings, black satin panties with lace and a bright red bra, I put my jeans and shirt back on for a little surprise reveal. I walked back out and the porn was already going. He asked if I was okay and I said Yes. Told him that I wanted to strip down in a bit for him. We started slow. I watched the porn on the TV for some pointers since I really had no clue what to do. I slowly revealed my bra the took my jeans off. He said I looked so sexy. He rubbed my bra and panties. I was so hard. I rubbed his cock with my hand. He had a nice 6.5 to 7 inch cock. He asked me to suck his cock. I got on my knees and took some cues from the porn. He told me I was doing great and that it felt so good. After a few minutes he told me to slow down or he was going to cum. After more teasing and groping. He told me he wanted to fuck my virgin ass so bad. He told me to go into the bed room if I wanted to be fucked. I asked if he had lube and condoms. He said oh yes. I told him okay and to be very gentle. I got up and he spanked my ass and told me how sexy I was again.
We went into the bedroom. I asked how he wanted me on the bed. He told me face down and ass up. He pulled my panties down and lubed me up. He teased with his finger and the tip of his cock. I wanted him so bad. I was so horny at this point. He eased his cock in me and I moaned. It hurt but felt great at the same time. The pressure increased as he slid in further. I almost had to tell him to stop then he said that that was all the way in. He rocked slowly back in forth. I moaned and told him how good he felt in me. He started to pump harder. I had to grab a pillow and cover my mouth to silence my pleasure moans. After a few minutes he grabbed my bra strap and held on like a rodeo rider. I felt his cock expand into my ass. He told me that he was going to cum. He pulled out and shot his hot load down my back. It was so hot, it went to my bra strap. We laid ther for a few minutes. He told me now great I was and I told him how good he felt in me. He later told me to call him when I was horny and he would gladly fix my problem. This turned into a several month booty call relationship. He would sometimes call me and tell me that he had a special outfit for me and that I needed to come over and show it off for him.
He eventually had to move away but not before giving me one more great night. I will write about it later.