Risque chats lead to lead to phone sex which lead to CFNM
I have a customer who started coming by my business a few years ago. She was older than myself by a bit but a very funny lady. I think she enjoyed teasing me by saying things like she wanted to take me home with her or check out her hot tub and such. She always seemed to have the upper hand, leaving me embarrassed like an altar boy. One day I was helping her navigate some things online, showing her how to post an item. I had forgotten I had some windows open that I had Solo Touch and some videos on but were "hidden". The tabs were visible and showed the description of the sites on the toolbar. I realized this too late and couldn't pull up the tabs without calling attention to them. So we completed the task she needed help with and left.
I spoke with her the next day and I apologized if she happened to notice I had porn sites up on my computer. She hadn't but she waved it off as no big deal as all men do. While discussing it with her I was getting hard and I told her that the discussion was turning me on. I asked her if she'd mind if I masturbated with her on the line with me. She thought nothing of it and began telling me how she would take my cock in her mouth and pleasure me just like a phone sex operator. All of this as I sat at my desk stroking my cock. It was heavenly and I really enjoyed myself.
We did it one other time after that but then she seemed to shy away from our playful banter after that for a while. Six months or so ago we exchanged some emails that would get bawdy at times but nothing too sexually explicit. Mostly her teasing about this or that. I kept hoping for a repeat but no luck. Then one day I emailed her letting her know I was "playing" down at my business on a weekend and I hoped she had a good day. She responded it was early and chilly and I should be snuggled in bed. I didn't get that response until the next day so I responded that I again was in my office even earlier hoping she would give a flirty response. She responded with a simple "Have a great day. Great game today "Go Niners".
I emailed "I am really thinking I need a therapist"
She responded "You think too much. Thanks for being who you are. You can share with me anything you want which goes no further. I will be your therapist."
I responded "I don't think you are the kind of therapist that I need. I have shared more with you than almost anyone. However, I have only touched around the edge of what goes through my head. Our talks have planted a seed that is now a hedgerow. I would love to share more but I am not sure I should. I wouldn't want to offend you, which I feel I sometimes have."
Her reply "You won't offend me. I just ask what is really your truth. Go for it!!"
I asked "When is your couch available for an appointment? LOL. What do you mean by " I just ask what is really your truth"?"
Her "You said you would share more but you didn't want to offend me which you think you have in the past???"
Me "Ok here goes. You have starred in many/most of my masturbation sessions for a while now. Ever since we had our first explicit chat a while back. And I really enjoy it I must say. I know I shouldn't but I do. In my fantasy you are not a porn star or something, you just are with me while I am pleasuring myself. I doubt you have checked into porn these days but the term for my fetish is CFNM (Clothed Female Naked Male). Too much or should I continue?"
Her "Continue...I am getting educated.."
Me "I know that being married I should be having this conversation with my wife. However I was into this before I met her and it was something I was/am afraid to have a conversation about. I do have sex with my wife and also enjoy masturbating with her next to me. But I know the forbidden aspect of doing it with you makes it way more exciting. I think since you are such a kind person I find comfort in sharing these thoughts with you. I know it is wrong in many ways but I am kind of a slave to my desires for most of my life. This heart pitter patter makes me do things I know I shouldn't but do anyway. I have only done it with a few others in my life but they were really exciting experiences for me. With you it has taken a further turn in that I find myself wanting to defile your pretty feet. That day that I was at your house and you had had your foot surgery I vividly remember slipping your band aid back over your mended toe when it fell off. Since then I have sought out stories and videos of that genre of porn. It is kind if hard to type this in between things at work. Respond to this email if you would be willing to have this conversation by phone before work tomorrow."
Her "Sure. And thank you for trusting me to share your intimate feelings with me. I will always be here for you.
You're human to have these feelings."
Me "Also thank you for your reassurances about my feelings."
We then chatted on the phone about things. I had jerked off before I chatted with her. We just discussed that she understood that guys have wants and needs.
My next email "Thank you for your understanding of my desires. I really appreciate the chat today. I took care of myself before I called you this morning so I wouldn't be tempted to do it when we spoke. As such the post orgasmic guilt had set in and I may have been a bit timid on the phone with you. I found myself at a loss to discuss things out of embarrassment. Going back through this email thread I certainly found it exciting again."
Her "I'm glad that you took care of yourself and DON"T feel guilty. About what?"
Me "I am always glad to take care of myself. I can only attribute the guilt to growing up Catholic."
Her "What is your guilt about?"
Me "I think the guilt is because the things I think about and the fantasies explored are not socially accepted and while horney and exploring those fantasies the shame is set aside. After I have masturbated through orgasm the "need" to cum has gone and that need clouds judgement. Just as I was doing it an hour ago I wanted to call you and hear your voice as I masturbated at my desk. I didn't want to offend you with that request so I didn't. But the urge to do it was very strong."
Her "Your feeling's are socially acceptable, yet not to you. It is not that often talked about among friends/people. You bought the belief somewhere. You are perfect the way you are and you are a real man to confront your truths and I acknowledge you for that."
Me "I know I bought into it somewhere but it is still not something for regular conversation. I kind of feel that having a discussion with most females that I would like to have them watch me pleasuring myself would be met with a palm print to the face. My old boss used to have a saying that equated to there is always some percentage of people that would be open to anything. He'd say if a man walked up to a hundred women and asked them if they could grab their ass or breast, you'd get 2-3 to say yes. The same may be true in my situation. However it has taken me over two years to get the nerve to being up the subject. And I haven't even asked you directly if you would."
Her "I could be with you on that level yet not sexual w/me at this time. Thanks for asking for what you want."
Me "Pitter patter right here. I understand that it can't be sexual for you. I would respect that boundary if ever given the opportunity. I am totally ok with it being me being naughty with myself. I do that a lot anyway. I just want to experience your presence and positive encouragement while I make myself cum. I would love to answer your questions and respond to any requests while watched, being as you were allowing me to fulfill my fantasy."
Her "What a gift....."
We then worked out a day to meet and I went to her house. I felt really nervous but excited. Part two cumming.