I am 18 years old and will be going to university this coming fall. I am trying to make as much money as I can before I start. On Saturday one of my neighbors offered me $20 to mow her lawn knowing I was looking to make money. Once I was done she asked if I wanted to double the $20 to $40. I asked what she needed done. She came right out and told me all she needed me to do is to take my clothes off and masturbate for her. I asked her to repeat herself as I didn't think I really heard her ask what she asked. I told her I didn't think I could do that. She told me it was easy money but I told her I couldn't masturbate for her. She didn't give up easily and told me she would give me $40 just to get naked then. I told her I couldn't and she offered the $40 to have me strip down to just my underwear. I was in jeans and already shirtless and began thinking it would only be taking off one piece of clothing to get the extra cash. I was hesitating answering her and she offered $50 but added I had to be that way for at least 30 minutes. I began to think it was $30 more than I was original going to get for 30 minutes more work which works out to a $1 per minute for just being in my underwear. I agreed to do it and began to remove all my clothes except my underwear. She watched as I undressed and was staring at me in just my underwear. After being this way for about 5 minutes she asked how I felt being in just my underwear. I truly didn't feel uncomfortable at all being this way and told her so which may have been a bit of a mistake. She then began to try to convince me out of them. I turned her requests down. She then asked if the $50 I was getting for being in my underwear was really going to help me out. I told her I was going to be a great help. She offered me an additional $50 to get out of them. The extra money would have been a big help but being naked would not so I told her I shouldn't. She told me she could see I wanted to but something was holding me back. She told me not to hold back and to think how the extra cash would help me and to just do it. I was thinking about the extra money but didn't think getting naked for her was appropriate. She approached me and gave me hug but in doing so put her hands on the waistband of my underwear and began pulling them down. She had me step out of them and took them. There I was naked now fully exposed to her. We were still out in her yard at this point and she collected all my clothes and brought them inside. When she came back out she told me the extra %50 deal included me being this way for an hour or so from now. I told her she never told me that and I had to get home soon. She said she would get my clothes in an hour or so unless I wanted to get dressed now and leave. I told her I wanted to leave now. She told for me to leave now she wanted me to do what she originally asked. She meant masturbate and I wasn't prepared to do that and told her so. She told me just to do it and get it over with. She said if I would prefer to stay naked that was OK with her but asked how I would feel with some of her friends seeing me naked as they were dropping by soon. Her seeing me naked was one thing but a group of her friends was another. I decided a group seeing me naked was worse that one woman seeing me masturbating. I stood in front of her as she watched me masturbate. It was the most terrifying, embarrassing, humiliating, sexually arousing, all rolled into one, thing I had ever done. She made good on paying me the $100 and gave me my clothes back. She said it was worth what she paid and told me she may have some more work for me.
After it was all said and done, I am still embarrassed with her seeing me naked and doing what I did but there really isn't anything else she could have me now do so embarrassing.

Comments

Anonymous

by Anonymous on Jul 4, 2017 at 4:56 AM

Dude, just enjoy it. Make some cash and may be get laid. You'll regret it later in life if you dont.

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Anonymous

by Anonymous on Jul 4, 2017 at 9:00 AM

If this is true, lol, just think how much you could make doing a striptease for her friends, and letting them jack and suck you off. Could be a lot of work this summer!

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Anonymous

by Anonymous on Dec 8, 2017 at 7:09 AM

If you weren't such a pussy, you could have made a LOT of money from her! That is, IF this is a true story.

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