I bought a jelly rubber artificial pussy about a year ago. It's a hand held thing that you slide your dick into and jack off with. You have to lube yourself up and with the combination of that and the jelly type rubber it feels darn good! I use it all the time and I named it Jill.
I was sitting on the front porch after work recently talking to the woman next door. She is about 40. We started talking about sex and I mentioned Jill was my best friend. When I told her it was my artificial pussy she died laughing and asked me all about it. She was so curious! She begged me to go inside and get it and show it to her, so I did.
I explained how I had to slide myself up the rather small opening. There is a hollow tube running all the way through the jelly and out the top end. It is real stretchy so it expands as you slide into it. She just refused to believe my dick would slide inside there because the hole looks so small. I told her if she wanted to come inside I'd prove it to her! She said 'I dare you!'
We went inside and as I sat on the couch talking to her with her beside me, holding Jill and talking about it I started getting hard. I have known this woman for several years and she is pretty good looking, I just never thought I was going to ever be jacking off in front of her!
I was finally totally hard and I said 'well, here goes!' I pulled my pants and underwear down to my knees and sat back down. I propped my dick up and said 'Damn I'm hard!'
'Ummmm. You have a NICE dick!' she said.
She watched while I smeared lubricant all over my dick, then I slipped it up inside Jill. She is a translucent green color so my neighbor could see my dick inside of the artificial pussy. On my downstrokes my dick goes all the way through and out the other end. I started jacking myself slowly as she watched me. She was all eyes!
While I was doing this I asked her if she ever masturbated and she said she did. I told her I'd love to jack off with her sometime when she is masturbating. Or if nothing else, I'd love to just look at her pussy as I jacked off. I asked her if she would show hers to me right then as I was jacking. She was so excited watching me she had her pants off in a second or two and spread her legs. Looking at her bush and her pussy lips really heightened it for me. I didn't last another minute! I shot cum everywhere!
Afterwards she said 'That was HOT!' I told her I really liked doing that in front of her and I asked if we could do it again. She said 'sure!'
Now we have masturbated twice together, getting fully naked the second time. We're having a ball with it!