I know I brought this whole situation on myself but the fact of the matter is that Helen has a big mouth. Two years ago I moved into a apartment building and lived on my own for the first time. I was 22 and the youngest in the entire building. Helen is my next door neighbor and just turned 56 three weeks ago. She was always kind to me right from the start but also pushy and at times obnoxious. She is extremely heavy and always wears those ugly house coats. For some reason she seemed to like me right away more than I wanted her to. I work everyday during the week and she soon began fixing me meals and snooping into my personal life. She gave me a key to her apartment and insisted I give her my key which I reluctantly did. One day I came home from work and all my dirty clothes were washed and stacked on my bed. I thanked Helen for doing it then also realized she cleaned and vacummed my apartment. I told her it wasn't necessary but she claimed it gave her something to do since was alone and on SS disability. To an extent she began to spoil me. I never had dirty dishes or dirty clothes and my apartment was always clean. She would bring me a dinner a few nights a week or leave me a note that she put a platter in my fridge. She made cookies, cake and pie and treated me better than my mother ever did. After only a few months she began coming into my apartment in the evenings. At first she would knock before unlocking my door but before I knew it would just walk in on me, several times while in my underware and once when I was naked. I guess I was embarrased about it but she would just grin at me encouraging me to feel comfortable around her. She knew my girlfriend and I had broken up and kept asking me questions about it even asking me how our sex life was. I didn't want to talk about it but Helen was relentless and I did begin telling her personal things she had no right asking me about. Things not only about my x girlfriend but also about my family. She is the type of woman who can be intimadating and since she is so much older than me I think I let her intimadate me to an extent. She would just walk in on me once or twice a week to bring me things and got to where I never knew when she would come into my apartment. I wanted to get my key off of her but she treated me so well I think I felt to bad to ask her. She was sweet and kind but also became very dominating and careing for me as though I were a child. Aside from doing my wash she even ironed my work shirts and I no longer had socks with holes. The only times I didn't see her was on weekends when she went to her sisters house.
Seven months or more had gone by and by that time she saw me in my underware so many times it didn't bother me anymore. I thought to myself a few times and worried that she wanted me like a boyfriend which she didn't. She rarely walked in on me two nights in a row but one night she walked in and I was in my bedroom masturbating. I didn't hear her come in and I had just ejaculated and realized she was standing in my doorway. Now I was completely embarrassed even more than the time she saw me naked. She only grined at me and said she would take the platter to the kitchen for me. I put shorts on and didn't know what to do or say to her. When I walked into the kitchen I found myself starting to apoligize to her, when it really wasn't my fault she saw me jerking off. Then she half heartedly apoligized to me but also telling me it was ok for me to do that since I didn't have a girlfriend. She then went on to say she hoped I didn't mind her coming in and being her friend. She went on a long speal telling me of her loneliness and that the only other friends she had was her sister and the people in our building. She sheepishly told me she like seeing me undressed and that she had no sex life at all and only masturbated herself. Not leaving very much alone she also said she enjoyed seeing my penis and especially liked watching me masturbate. She had been standing watching me longer than I had relized at the time. I admit I was speechless and she just kept talking, finally asking me if I objected to her coming in my apartment as often as she did. Helen was giving me an opening to say I did object but without thinking about it I told her she was always welcome. Thats all she needed to hear and her visits became even more frequent.
It was a few weeks later when she caught me masturbating again, only this time I was already finished but still naked. Like I said before she saw me in my underware almost all the time but that was only the third time she had seen me naked. She only gave me a grin again and said she was sorry she didn't come in sooner. I just looked at her in amazement and then asked her if she liked seeing me naked and liked watching me masturbate. I put a towel around me and we went into the kitchen. As soon as we sat down she told me I was a slim handsome guy and that she never gets a chance to see a man naked or especially see a man playing with himself. She said she wishes I would be naked more often and then asked to see my penis again. Now I know this makes me sound like an exibitionist but I stood up and took the towel away letting her see me nude. All she said then was thank you. I have never had any sexual interest in her and still don't but find it fascinating that a woman like her could be so bold as to ask me to expose myself. Before she left she asked if she I could be naked sometimes when she comes over and for whatever reason, I agreed to it. I no longer felt embarrassed about her seeing me nude and perhaps thought of it as a compliment as rediculous as that may sound. I seldom went out during the work week and began being naked almost every evening even when Helen didn't come in. When she did it was obvious she was pleased when I was naked. It did feel strange for a month or so but I began enjoying her looking at me. My penis is only average at best and I guess it made me feel more confident of myself by the way she kept looking at me. At first I didn't get erections often but after a short time I started getting them often. I said things to her referring to my penis size and she always reassured me that I was normal. She no longer left platters in my fridge but would bring them in and heat them up for me. I even eat naked sometimes and she would sit talking to me as I did. It was last December the first time she asked me to masturbate in front of her. She did see me twice before but not when I knew she would be watching me. The first time I knowingly jerked off in front of her I was standing up but after that I would lay on my bed and do it. With no sexual feelings for her it did stimulate me just having her watch me. What I thought would be humiliating has become more of a turn on for me. Thursday evening February 3, 2011 is the first time she mastubated me and simply asked me if she could. I don't know how much experience she has had but I have never been jerked off as well as she does it. She put baby oil on her hands and not only held my penis but also held my scrotum and brush her finger along my anus up to the bottom of my testicals. She masturbates me once or twice a week now always asking my permission. Other times she just likes watching me masturbate myself. She never touches herself and has never taken her clothes off or exposed herself in any way. I know she is embarrassed about her body and has told me so ..(continue confession)
Seven months or more had gone by and by that time she saw me in my underware so many times it didn't bother me anymore. I thought to myself a few times and worried that she wanted me like a boyfriend which she didn't. She rarely walked in on me two nights in a row but one night she walked in and I was in my bedroom masturbating. I didn't hear her come in and I had just ejaculated and realized she was standing in my doorway. Now I was completely embarrassed even more than the time she saw me naked. She only grined at me and said she would take the platter to the kitchen for me. I put shorts on and didn't know what to do or say to her. When I walked into the kitchen I found myself starting to apoligize to her, when it really wasn't my fault she saw me jerking off. Then she half heartedly apoligized to me but also telling me it was ok for me to do that since I didn't have a girlfriend. She then went on to say she hoped I didn't mind her coming in and being her friend. She went on a long speal telling me of her loneliness and that the only other friends she had was her sister and the people in our building. She sheepishly told me she like seeing me undressed and that she had no sex life at all and only masturbated herself. Not leaving very much alone she also said she enjoyed seeing my penis and especially liked watching me masturbate. She had been standing watching me longer than I had relized at the time. I admit I was speechless and she just kept talking, finally asking me if I objected to her coming in my apartment as often as she did. Helen was giving me an opening to say I did object but without thinking about it I told her she was always welcome. Thats all she needed to hear and her visits became even more frequent.
It was a few weeks later when she caught me masturbating again, only this time I was already finished but still naked. Like I said before she saw me in my underware almost all the time but that was only the third time she had seen me naked. She only gave me a grin again and said she was sorry she didn't come in sooner. I just looked at her in amazement and then asked her if she liked seeing me naked and liked watching me masturbate. I put a towel around me and we went into the kitchen. As soon as we sat down she told me I was a slim handsome guy and that she never gets a chance to see a man naked or especially see a man playing with himself. She said she wishes I would be naked more often and then asked to see my penis again. Now I know this makes me sound like an exibitionist but I stood up and took the towel away letting her see me nude. All she said then was thank you. I have never had any sexual interest in her and still don't but find it fascinating that a woman like her could be so bold as to ask me to expose myself. Before she left she asked if she I could be naked sometimes when she comes over and for whatever reason, I agreed to it. I no longer felt embarrassed about her seeing me nude and perhaps thought of it as a compliment as rediculous as that may sound. I seldom went out during the work week and began being naked almost every evening even when Helen didn't come in. When she did it was obvious she was pleased when I was naked. It did feel strange for a month or so but I began enjoying her looking at me. My penis is only average at best and I guess it made me feel more confident of myself by the way she kept looking at me. At first I didn't get erections often but after a short time I started getting them often. I said things to her referring to my penis size and she always reassured me that I was normal. She no longer left platters in my fridge but would bring them in and heat them up for me. I even eat naked sometimes and she would sit talking to me as I did. It was last December the first time she asked me to masturbate in front of her. She did see me twice before but not when I knew she would be watching me. The first time I knowingly jerked off in front of her I was standing up but after that I would lay on my bed and do it. With no sexual feelings for her it did stimulate me just having her watch me. What I thought would be humiliating has become more of a turn on for me. Thursday evening February 3, 2011 is the first time she mastubated me and simply asked me if she could. I don't know how much experience she has had but I have never been jerked off as well as she does it. She put baby oil on her hands and not only held my penis but also held my scrotum and brush her finger along my anus up to the bottom of my testicals. She masturbates me once or twice a week now always asking my permission. Other times she just likes watching me masturbate myself. She never touches herself and has never taken her clothes off or exposed herself in any way. I know she is embarrassed about her body and has told me so ..(continue confession)
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