For several years I was taking adult classes in Spanish several evenings a week. I was taking these courses because I love foreign languages and for no other reason. The classes were made up exclusively of adults, most like me, just interested in learning a new language.
Some nights after class a group of us would go and have a few drinks and good conversation. It was during these outings after class that I became close friends with one woman I will call Debbie. She is very shy and sometimes conversation is difficult, nevertheless I found her quite charming and fairly good looking too.
One night after class I walked her to her car and found myself giving her a good night kiss. It wasn't one of those passionate ones, just a little smack on the lips. The next evening after class and after drinks with the others I again walked her to her car and this time the kiss lasted a bit longer. I asked her if I could get in her car for a while and she said that was OK, so inside her car we more passionately kissed.
I drove her to a little pub the next night after class, and again back at my car afterwards we made out. This time I was so hard, I whispered into her ear as we made out that I wanted her to feel me. As we kissed I felt her hand slide down to my lap and I felt her hand caress my hard dick through my pants. It felt so wonderful to feel her hand squeeze me and feel me. As she felt me I tried to feel her breasts but she squirmed and said she was so shy ... she said she was embarrassed to let me feel her and stuff like that. I don't know if a man has ever seen her naked before, and she was about 45 then!
Another night after class and making out in the car, she feeling my really hard rod, I asked her if she wanted to look at it and she just nodded yes without saying anything. We were in a rather dark parking space so I unzipped and pulled my super hard dick out. She wrapped her fingers around it tightly and kissed me passionately. I asked her to jack me off so as she kissed me she jacked me until I squirted my cum all over my lower shirt.
We didn't have class one night so I asked her if I could come over to her house and she said that was OK, so off I went. Inside her house where we were safe from being seen we made out passionately, but at the slightest touch to her breasts or between her legs made her freeze. She was so uncomfortable with having her body touched, and she certainly wasn't going to get naked for me at all. It was obvious she had some deep problem mentally concerning her body, or how she perceived her body, etc. Actually, she has a very nice body. In spite of that, she was quite passionate with me and had no qualms about feeling my dick. Here I was at long last in her bedroom kissing her, she feeling my dick, me unzipping, she reaching inside and pulling me out, ... and I finally said 'Screw it!' I stood up and totally removed my pants, shirt, and underwear. I told her to get down and look at me really well, so she kneeled on the floor and looked at my throbbing dick very closely. Se ran her hands up and down my length, under my balls, through my hair and back to my dick. I told her I wanted her to get naked too and I told her I'd love to look at her pussy and taste it, and fuck her all night long. She said she just couldn't get naked because she was too embarrassed and she was too shy about her body. All my pleading went down the drain. I finally told her 'jack me off good then...' so she took my throbbing dick and jacked me until I squirted cum all over her bed and her blouse. Afterwards she laid beside me on her bed, her fully clothed and me naked, and she fondled my dick as she talked to me. She, unfortunately, has a real inferiority complex the roots of which I don't know and don't understand.
I do enjoy getting totally naked with her as she kisses me and jacks me off, even though she won't get naked. She does love jacking me off and she is wonderful at it. We just can't get past here though.