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She was my babysitter.

Tagged as: Age differences, Friends<< Previous question   Next question >>
Question - (17 November 2007) 5 Answers - (Newest, 18 November 2007)
A male United States age 36-40, anonymous writes:

My questions are regarding an older woman. She is eleven years older than me. Perhaps some background would be helpful. The woman we are talking about I have known for a very long time. She was first my babysitter and then she helped me with homework throughout my jr. high and high school years. We have always been close. After serving in these roles in my life our relationship began to change. We started hanging out and doing fun things together. She is caring, attentive, bright, fun, and very beautiful. When I close my eyes I cannot help but see her with her beautiful long blond hair, nice smile, and her athletic body. When I can I try to sneak peaks at her breasts, which extend nicely out of her tops and her nicely formed rear end. Having said this I have not seen her in the nude but would very much like to. I have come to care deeply about this woman. I love it when I can run my hands through her hair and kiss her on the face.

A few weeks ago we were out for a nice evening of dancing. I could not help enjoy the close dancing. It was during these dances that her breasts were resting on my chest. There were only a few layers of cloth separating us. It was after this evening that I knew that I wanted to become more intimate with her. The next time I saw her I attempted to openly communicate this desire to her. I believe in open and honest communication with her. When I brought up the subject she seemed to change it. Maybe she is unsure of how she should respond and I respect her for this. Perhaps there are concerns about our prior background and/or our ages. How can I ensure her that these are not problems?

Since I tried to engage her in conversation about this without luck would it be ok that the next time we are alone in private together to just act on my feelings for her? Maybe this would open up communication with her on this subject matter or allow us to communicate in non-verbal ways. Next time when we are alone and I have the chance to rub my hands through her soft hair and kiss her smooth skin maybe I keep working my hands and mouth down her body. In the process I would be attempting to finally see her in the buff. This is bound to open up some communication. What do you think?

If we get beyond the point as to where we have been before what can I do to make our intimate time together very beautiful for her? Any advice about non-verbal intimate communication?

Regards,

Patrick L.

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A female reader, AnnaW219 United Kingdom +, writes (18 November 2007):

AnnaW219 agony auntmaybe she changes the subject because shes scared that you have maybe noticed she loves you if she didnt care for you then why would she let you hang about with her and 11 yrs is nothing at all if you like her ask her if she likes you when sno one is near and its you and her toigether tll her what you feel ask her if she feels the same even ask her on a date but ask her like its a friendly night out then if she says are you asking me on a date say yes as well you dont have to tell her like oh i love you just tell her by your actions the way you speak and what you say i meen ever woman wants a toy boy. so go for it good look

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A male reader, Richard_EMids United Kingdom +, writes (17 November 2007):

Richard_EMids agony auntYou ask for advice about intimate communication:

Well, when you're in the middle making hot passionate love to her ....just don't call her Nanny!

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A female reader, hlskitten United Kingdom +, writes (17 November 2007):

hlskitten agony auntHi

You have both posted a question about each other. Maybe talking to each other would be more ideal than seeing what the other has put on here. And what others say. Afterall the best judge of whats best for you is yourselves.

11 yrs is nothing though by the way, and as long as no one is getting hurt (ie other people/partners) then you should go for it.

Good luck.

C xxxxx

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A male reader, anonymous, writes (17 November 2007):

Hasnt she just left a message before you same thing anyway

so talk to her

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A male reader, anonymous, writes (17 November 2007):

Is this question genuine?

look at http://www.dearcupid.org/question/the-nice-boy-i-babysitted-and-tutored-has.html.

Its kinda clear its the same story from both sides - posted with 2 minutes of eachother - what are the chances of that happening for real???

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