Mandy and I had sex last night and while I don’t want to share too many intimate details I do have concerns and would appreciate some advice. As some of you already know apart from a one night stand (I don’t even remember because I was drunk) this was the first real time I have done ‘it’ with a woman and she is also the first woman I have had a real relationship with since my girlfriend/best friend passed away so I was very nervous. We were originally going to wait longer but we were in bed talking and I said some things to her and she just started kissing me and she took her top off.

I moved back and said “I thought you wanted us to wait longer” and she said she did but she had changed her mind and she wanted to make love to me. Mandy was very gentle with me and she knew I was nervous. To be honest, it was a little awkward at first but it got better as we kept going and I think I lasted for around twenty minutes. She tried to go down on me when I took off my pants but I told her I was uncomfortable with the idea of her doing it and she said that was okay because she wasn’t really into doing that either but she thought I would like it. I went down on her instead.

She spent most of the time on top of me but we tried out some other positions too and when we were finished she said I was incredible at going down on her but the actual sex was only good. She said I was too big and I hurt her when we were in some positions. I didn’t mean to hurt her and I don’t want to do it again. Is there anything I can do to fix this problem for her? It’s strange because I didn’t know I was that big. I’m usually a smaller when I’m soft but when I’m erect I’m around eight and a half inches and I thought that was a regular size for most blokes.

Mandy said it would get better the more times we did ‘it’ though and I was the first bloke she did ‘it’ with that she loved before she cuddled me. She was very curious why I was so good at going down on her and I just told her I went down on Jessica a few times before she passed away. I didn’t tell her that Rachel taught me some things and I remembered them and I’m not sure if I should. Mandy is so beautiful and seeing her naked just blew me away. She has a body like a supermodel and I feel like it was a beauty and the beast moment in a way because I'm a bit skinny and pale.

I used to go to the gym with Rachel every day before she passed away and did a lot of cardio but I stopped because I was really depressed and didn’t think there was a point. I stopped eating for a few months too and became very close to becoming anorexic. I only weighed sixty kilos back in February but I now weight eighty. I am running every morning with Mandy now and I'm eating more. I am worried in a way that I am not attractive enough for her but she has never said I am not and she says that I am cute so I probably shouldn’t let it bother me. The way she looks at me with her blue eyes says it all.

One thing she doesn’t know is I started crying when she left the room and I tried to cover it up when she came back. I thought about Jessica and I felt guilty for doing ‘it’ with Mandy. I know I shouldn’t but I did and now I am worried Jessica might hate me. When she passed away a lot of people didn’t understand why I couldn’t move on and part of the reason was the guilt factor. I couldn’t bring myself to ask another woman out because I was worried I would hurt her. I love Mandy and she is an amazing woman but part of me is always going to love Jessica. It’s difficult because I gave my heart to her when I was five and for eleven years she was my world.