For the last 2 years I travel to Chester County, PA and stay at the same motel for 2 nights for my job twice a month. Arlene is one of the cleaning ladies and well over a year ago I began taking advantage of her. She is 44 and not attractive at all but extremely friendly. She also is not very bright and I doubt she ever finished high school. At first I only started telling her about my aches and pains saying I needed a massage. After a few times telling her that I asked if she was able enough to give me a massage and that I would pay her 75. She was more than willing and the first time when she was done work she came in my room. I put towels on the bed and only had a towel around me and just by the expression on her face knew she didnt mind my lack of modesty. I handed her a bottle of lotion and as she was rubbing my shoulders I asked her if she would be offended if I removed the towel. I said something like you dont mind seeing me naked do you To my delight she said she didnt mind. She never touched my genitals the first two times but came close enough for me to get an erection for which I semi apologized. The third time I was able to have her jerk me off paying her 100 instead of 75. I never have sex with her and doubt she wants me to. I cant believe how she has no problem now not just jerking me off but the way she talks to me. She also asks if this or that feels good and spends most of the time rubbing my genitals and even spreads the lotion around my anus. I have a throbbing hard on as she does this and often ejaculate twice. Five months ago I asked if she thinks I should shave off my pubic hair and she did laugh but when I came back two weeks later I did shave myself. She said she liked it and now I have her shave me sometimes, before she gives me the massage and jerks me off. Originally I was the one taking advantage of Arlene but now in a way she is enjoying it also. She positions me or has me kneel on my hands and knees as she rubs inside the cheeks of my ass and holds my scrotum and penis from the rear. If I had any morals it would be humiliating by the way she has me exposed to her. I know this began because of my paying her which I still do, but I truly believe she likes touching my body and jerking me off. I think she also likes seeing me naked in awkward positions to the point where she actually poses me. I wonder at times if she is purposely trying to embarrass or humiliate me. If thats what she is doing I dont care and enjoy every minute of it.
General Confessions - 1 Month ago