First let me say how much I love this site. I have been jacking off for about fifty years now and love it as much as I ever did. My cock still gets rock hard and I still squirt pretty good. I was married twice and jacked off the whole time I was married. I have dated many women and made no secret about how much I jacked off. I made sure at one time or another all of them caught me milking my cock. I got mixed reactions. Some of them thought it was cool and others thought it was a form of cheating on them.
Anyway, this one woman I dated, Tina, off and on for about five or six years, had two daughters, Rea and Tess. When this happened Rea was sixteen and Tess was fifteen. Tess was cute but Rea was a knockout. I secretly wanted her but was careful not to let my intentions be known. I think Rea knew it because when her mom wasn't looking she would flash her gorgeous tits to me and smile when she caught me looking. One day when I was over and her mom was outside she called to me from the shower to bring her another towel. When I knocked on the door she said come in. I opened the door and she was standing there butt naked with a towel wrapped around her head. She was so beautiful I just couldn't take my eyes off her. She said, 'What's the matter? Haven't you ever seen a naked girl before? I said, 'Sure, just not one as knockout gorgeous as you.' She stepped over to me and took the towel and gave me a quick kiss on the lips. She asked if I would keep her company while she finished drying off and put on some lotion. I told her I couldn't think of anything I'd rather do and she knew I was telling the truth because she saw my huge hardon trying to push it way out of my shorts, but I said with her mom just outside I could get in a lot of trouble. She pretended to pout and said, 'OK, maybe next time.'
On days when I got off early I would go over to Tina's and wait for her to get home. This one day I had called her and she said the girls were going home with friends so I would have the run of the house. As soon as I got there I was out of my clothes and out on the patio to jackoff. There was this attractive woman that live next door and I had let her catch me in the back yard jacking off several times. I don't know if she ever told Tina but Tina never said anything to me about it. I was hoping to get another flash in before Tina got home. I put on some cockrings and got my cock all lubed and started stroking my cock. It felt so good being outside with a cool breeze blowing over my naked body. I was stroking really slow to make it last and make myself cum harder. Tina wasn't due for a couple of hours so I could just relax and enjoy and hope the woman next would catch the show.
I had been jacking off for about 45 minutes and had my eyes closed for the last 15. I opened them slightly and out of the corner of my eye I saw Rea standing at the sliding glass door watching me. At first I was in shock but then decided what the hell. I pretended I didn't see her and just kept stroking my cock. I was going slowly but knowing she was watching me was making my cockhead tickle like crazy. Then I heard the sliding glass door open and I couldn't pretend I didn't know she was there anymore. I said, 'Rea honey, I thought you were supposed to be over at a friends. I am so sorry.'
She didn't say a word as she walked over and pulled another lounge chair up right in front of me. She sat down two feet away and put her legs inside my wide spread legs. She had full view of my very hard cock and fat balls. She took her eyes off my cock and looked me in the eyes and said, 'Don't you dare stop doing that. I have never seen a man masturbate before and it is the hottest fucking thing I have ever seen. Mom told me you had nice equipment but I never thought it would be so big. Are you going to make yourself cum?' I told her I definitely was but I was teasing myself to make it last longer and make me cum harder. I told her I had dreamed about her watching me jackoff and came many times thinking about her. I asked her if she masturbated and she said she had for several years. I suggested she join me but she said it made her very self conscious and she could never do that in front of anyone. I suggested she stick her hand down in her gym shorts she still had on from school then I couldn't see anything.
She must have liked that idea because her hand disappeared down her shorts. I could see her hand moving on that beautiful pussy that I had seen in her shower and by the moaning I knew it was feeling very good. I told her to take her time that I could wait as long as she wanted to cum with her. Just then she stood up and was out of her shorts and panties and then the top was gone. There she was in all her beauty for my eyes only. She sat back down and put her legs up over the arms on the chair and she was baring her body and sole to me. She was fingering herself like mad and I was jacking off to match her. I said, 'Rea, you are the most beautiful woman I have ever seen in or out of her clothes.' Then she totally shocked me when she said, 'I want you to cum on me.' I said, 'WHAT?' She said, 'You heard me. I want you to squirt your cum all over me, please, please.'
Her wish was my command and I was gone. I stood up right over her and she looked up into my eyes as I started unloading my cum all over her beautiful tits and body. I lost all control as she screamed with pleasure as her hands brought her to a beautiful orgasm. I sat back down and we were both quiet for a few minutes. We then both laughed at what had happened and Rea said, 'Come on hot guy let's go take a shower.' We had a lot more fun and her mom never found out. Rea lost her virginity to me.