It has taken years to get my wife to this point but we are finally here. I met her in university and she was a shy and timid bookworm. We hit it off well but she was very reserved in bed and with anything related to sex. I gave her her space and gently encouraged her at the same time to explore a bit and with time she became comfortable with me to try more daring things. The first was laying out topless on the beach which she said felt incredible even though she was scared. This dare here with TODP will be our next step and we hope to get lots of nice emails from everyone here.
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The MILFs are single, married but looking, or in open relationships and most have busy lives being moms and working. So discretion is preferred and they are usually quick to act without much in the way of gamesmanship.