This story is about how I got my second girlfriend to watch me masturbate. Comments are welcome.
After my first contribution had been about my first girlfriend, I am now writing about my second girlfriend. We have been together for more than six years. Besides having sexual intercourse and oral sex we also masturbated each other to orgasm on a regular basis. But we have never pleasured ourselves and watched each other. I had asked my girlfriend once if she would be willing to do it in general and she said yes. But every time I asked her if she wanted to try it tonight she said no. I had the feeling that she was just too shy to let me watch her pleasure herself, but that she was maybe willing to watch me masturbate. But at first I did not know, how to bring that up.
When we were masturbating each other it would always be one after another. We rarely masturbated each other at the same time. One evening she was lying as usual on her right side next to me in my left arm and was jacking me with her left hand. When I jack myself off, I love it to massage my balls with my other hand at the same time. So I asked her if she could caress my ball sack with her other hand. Because she was lying on her side in my arm she would have to sit up to do so. She said it was so comfortable and cuddly to lie in my arm and she wanted to stay like that. So I asked her if she would mind if I caressed my ball sack myself with my free right hand. She said ok, so I did. I then let her jack me to a wonderful orgasm while I massaged my balls.
We did this from time to time over the next couple of weeks and she did not mind at all when I fondled my balls. So once when we were at it again, I asked her if she would mind to switch, so that I jack my cock and she caresses my balls. She said ok, so we switched. I then jacked myself off the first time while she watched. Because this was something new and I was really excited about it plus she was massaging my balls I had an awesome orgasm and squirted more than I usually do.
Over the next couple of weeks we did this too from time to time. Sometimes we would switch jacking me several times before either she or me brought me to orgasm. Once when I was jacking me again and she was fondling my balls I asked her if she would lick and suck at my balls while I continued to jack me off. She said ok and moved between my legs. Then she started first to lick my clean shaven ball sack very gently and began then to suck my balls into her mouth. I was in heaven. While she did this, I jacked myself to one off the best orgasms that I ever had. My cum spurted farther than it usually does.
So, if you have ever wanted to jack yourself off, while your girlfriend watches you and you never new how to bring the subject up you could try my method.
I hope you liked the story. Happy jacking and jilling.