My mom and me live in a condo and on the other side of the pool is an old man named Miles who we have known for a long time now.
My mom works a lot and is out of town several times a month. Miles took a liking to both of us and we see him a lot and talk to him and have him over for dinner often. He never talked about sex when my mom was with me but always did when we were talking alone. At first it wasn't anything about me but he would tell me stories of his ex-wife and other woman he had sex with. He began telling me he has a hard time getting an erection and that he hasn't had sex with a woman in many years. He told me that he tries to masturbate but can't get hard enough. He did ask sometimes if I minded him talking about those things but I always told him I didn't mind and I really didn't. It was last summer when he told me he watches me at the pool from his condo and tries to masturbate looking at me. He said he hopes I'm not offended and began telling me how beautiful I am and how he likes seeing me in my bikini. I think because of his age I only laughed about it and wasn't at all offended. He always knew when my mom was out of town and would invite me to his condo for lunch. I think I was intrigued by his stories so I have lunch with him whenever he asked. He would begin telling me his sex stories which some I didn't believe. Around that time last summer he began asking me personal questions about my sex life. I just want to say I did and do like Miles very much and saw no harm talking about sex with him. I opened up and told him about the only three boys I had any kind of sex with and did tell him I have sex with my boyfriend who is in the Army. He asked if I masturbated, how often and even how I did it. Why it didn't embarrass me I don't know but gave him details of how I did masturbate and where, like in the shower or in my bed.
I'm not sure but think it was early August 2011 when we were having one of our usual talks over lunch. I thought I was hearing things at first but he asked me if I wanted to see his penis. Instead of just saying no I think I said why. He just told me he was having a very hard time getting an erection anymore and thought if I looked at him he might be able to get one. He said he knows I already saw guys naked and that he wasn't trying to have sex with me because he couldn't anyhow. I don't know what I actually said but I knew he was a harmless old man and I finally told him to show it to me. Sure enough he pulled down his pants and exposed himself. His penis is smaller than any of the boys I ever had sex with. Without saying anything he started to try and jerk off in front of me. He just kept pulling on his penis for awhile but nothing happened and he couldn't get hard. Then he really surprised me when he ask me to let him see my breasts. Whatever possessed me to do that I still don't know. I don't remember whether I felt sorry for him or whether I was aroused a bit by the thought of it. I didn't take off my blouse but did unbutton it and pull up my bra as he continued to try and get an erection. His penis did get a little hard but far from a full erection. Then he asked me to hold my own breasts, which I did and without having a real hard on he did cum. All he did was keep thanking me over and over again telling me he hasn't been able to ejaculate in a long time.
About a week later when my mom had to go to Boston and Miles came over to the pool telling me he made me lunch. When I went in lunch was on the table and we sat talking again about sex and again he began thanking me for showing him my breasts the week before. The conversation turned to masturbation and just talking about it with him got me aroused. I hadn't seen my boyfriend in three months and did masturbate often. I was in my bikini and Miles kept looking at my body and telling me how he wished he was 40 years younger. We weren't finished eating when he began asking me to let him see my breasts again. I did say no this time but he was persistent and kept asking. I finally gave in and took my top off and asked me to stand up. He then dropped his pants again and began trying to get an erection. He kept jerking off and again was able to cum just by looking at me topless. I think I did get some satisfaction knowing how I could get him to ejaculate. I went back to my condo a little later and masturbated myself. By the middle of September, Miles had me showing him my breasts once or twice a week then convinced me to let him see me naked. By that time I began enjoying exposing myself and seeing him ejaculate even though he never had a complete erection. I could see how happy my nudity made him and it caused me to become aroused by his reaction.
It was but a few weeks later when he asked if I would let him watch me masturbate. What I originally thought would be to humiliating to do came very easy for me. Seeing him watch me finger myself wasn't embarrassing at all. Perhaps because he had seen me naked many times but also with him watching me had me more aroused then if I were alone. The very first time he watched me I orgasmed twice. It was only a month or so after the first time that I masturbated him and he still never had a full erection. Then I began letting him maturbate me even when my boyfriend came home on a 30 day leave. I should be ashamed of myself for letting this old man not just masturbate me, but also fondle my breasts and for that matter my entire body. He sees me in ways my boyfriend doesn't and 8 months ago bought me a vibrator which I let him use on me at least once a week and twice a week when my mom is out of town. I can't believe the things I let Miles do to me or the things he has me do to him. He is the only one who has ever penetrated my anus with his fingers and does so every time he puts the vibrator in me. I have more orgasms with Miles than I have ever had. When I jerk him off he likes me to play with his testicles and it seems to make his penis slightly harder when I do. The thing is it's not like Miles is taking advantage of me, which he may be in a way. Its just that I like Miles seeing me naked and I even like masturbating him and have him masturbating me. I like Miles and I don't care how old he is and it makes me happy knowing how I make him happy and satisfy him. We have him over for dinner a few times a month and my mom really likes him also. She thinks he is just a lonely old man which I can assure you he isn't anymore. I never go over to Miles when my mom is home and she can never find out about this.