My girlfriends youngest brother Alan is not just a nerd but a computer geek. He is very bashful and not very good looking at all. I have known him for more than ten years and always felt sorry for him. He's short, skinny and not at all good looking. Most of the neighborhood guys always picked on him. He's 19 now but still bashful and quiet and has had a crush on me since he was a little kid. As shy as he is, he is always happy and talkative with me.
About four months ago I had trouble with my computer and Alan offered to fix things for me. I live in my own apartment now and the second night he came over we had a terrible snow storm. He still lives with his parents but I suggested he stay at my house that night since it was so bad to drive. We ended up talking for a few hours and I made dinner for us. He told me things about himself I never thought about and told me how most of the girls he knew had no interest in him and that he never really had a date with a girl. He almost had me in tears with some of the stuff he told me. He had few friends and I guess I never considered how lonely and fragile he was. He didn't finish with my computer that night and said he would come back that Saturday.
I didn't expect him to come so early and had just gotten out of bed. I answered the door in my nightshirt and he tried to act like he wasn't looking at my body but I knew he was checking me out. He had seen me in my bathing suit many times over the years and I knew he liked me very much and always looked at me. After a few minutes he went over and started working on my computer. I left him alone and went in to take a shower. I am seven years older than Alan but always knew he liked me. Not only that I always noticed how he would look at my body when he thought I didn't know that he was.
What possesed me I don't know but after my shower I came out with just the towel around me. I don't know if I did it to tease him or not but as soon as he saw me he started to blush and turned beet red. I held back from laughing and could see he kept looking at me out of the corner of his eye. I asked if he had breakfast and when he said no I went into the kitchen and made us ham and eggs. My apartment is small and I just stayed in my towel as I cooked. He was looking at me the whole time and I admit to bending over a few times exposing my rear to him. I had never done anything like that before and don't know if I did it to tease him or just to flaunt myself.
When I called him into the kitchen I asked him if he minded me being in the towel, again I think I said that to tease him. Right away he said it was ok and I just smiled at him. He sat across from me as we ate and talked again. He dropped his spoon once and then dropped the napkin which was so obvious I knew he was looking under the table at me. I asked him if he was trying to see my privates and he blushed even more than before. That's when he told me how pretty he thought I was and admitted he saw my rear when I was cooking. I told him I knew he was always looking at me for years and am sure it embarrassed him.
We finished eating and just sat talking to each other. He told me he always liked me and still had pictures of me in his room at home. I don't know how it started but somehow the conversation became about him getting hard when he looked at me. I don't even think he used the word 'hard', but I knew he was talking about getting an erection. I think I asked, just to embarrass him more, since I knew it was easy to make him blush. I just asked if he masturbated thinking about me or looked at my pictures when he did. As soon as I said it his face became fire engine red and I just couldn't help but laugh. I never dreamed he would get so emotional and before I knew it he was crying like a small child. I felt terrible laughing at him and said I was sorry. He was really upset and I wished I never said that to him. He said he had to leave and just went home leaving my computer disconnected.
I never said anything about it to my girfriend and quess I never realized how sensitive he really is. That night I called him and told him how sorry I was and he said he was sorry to and that he would come back Tuesday to finish working on my computer. He was going to school in the evenings so he never came until about 9:30. I thought he forgot or just wasn't coming over. I was in my night shirt again and when he came in I hugged him and told him I was sorry again. He worked on the computer for almost an hour and in the meantime I ordered a pizza for us.
We just sat and talked for awhile and once more he talked about how inept he was with girls and admitted to me that he never had sex and only kissed a girl one time. He said he masturbated a lot but that was all. He said he never even saw a naked girl before except on the computer or in a movie. I did really feel sorry for him and the next thing out of my mouth I told him I would show him my breasts if he promised not to tell his sister, which he swore he wouldn't. I don't know how I got the nerve but I stood up and took off my night shirt, standing in front of him with only my panties on.
As amazing as this my sound he turned bright red and was almost in tears while looking at me. I asked him if it aroused him and he admitted right away he had an erection. I think it also aroused me right away and he asked if he could touch me. Again I just said only if he doesn't tell his sister. When he got up I could see he had an erection and I allowed him to fondle my breasts. At one point he leaned over and kissed them. I felt myself getting wet and told him to come into the living room.
He sat on the sofa and without telling him I took my panties off and sat down beside him. His eyes were the size of silver dollars and before he touched my vagina asked if it was ok. To his suprize I unhooked his belt and undid his pants. I then made him stand up and take them off along with his shirt and underware. He had a full erection but not a very big penis. When I put my hand around it he just moaned and ejaculated within seconds. I was sitting in front of him and he was still standing as I masturbated him. When he did cum it went all over my breasts and stomach. He started blushing again and telling me he was sorry and said he couldn't believe we were both naked.
His erection went limp and he grabbed and put his underware on right away and started getting dressed with me still sitting on the sofa completely naked. I got up and put my night shirt back on and he said he had to go home. After he left I was still aroused by the whole episode and masturbated myself. I couldn't believe how fast he came and it seemed like he did as soon as I stroked his penis a couple times. I didn't see or hear from him in over a week until he called me. He just said he was embarrassed that he came so fast but asked me if we could do it again sometime.
He knows I have a boyfriend but for some reason I told him he could come over again. I made it clear to him that I am not his girfriend and that he could never tell his sister about what we are doing. So now when he comes over its only twice a month. We masturbate each other and three weeks ago is the first time we moved on to more things. I taught him how to kiss and he is rather good at it now. I laugh at some of his reactions and the funny thing is it still embarrasses him when I see him naked. Even though he is 19 he acts like a 13 year old but at least he doesn't get upset anymore when I laugh at him. As nerdy as he is I have come to enjoy his visits and think I enjoy the way I dominate what we do. I make him get an erection sometimes and stop jerking him for awhile making him beg me to masturbate him. He knows by now I only do it to tease him. He has become much better at masturbating me. I have already told him I only have intercouse with my boyfriend. I know I am actually cheating on my boyfriend but I have become really fond of Alan. I have fun with him and part of it is making him blush or embarrassing him which is very easy to do. He still hasn't had a real date and I think I am the only girl he has ever touched. I still feel sorry for him but only do this twice each month when my boyfriend is on night work. Alan has wanted us to do it more often but I threatened to stop it if he keeps asking for more. I do enjoy it but still wish he could find a girfriend and stress to him not to get to attached to me. I guess there are a lot of guys like him and I am always telling him how to talk to a girl and things to say to them. He is just too bashful around people and I just hope he gets over that soon.