When my mother-in-law found me she laid down the rules!
While living at my girl-friends house before we got married, I was working the night shift at a restaurant and so I would be at the house during the day while my girlfriend and future father-in-law were both at work. This allowed me plenty of time to sneak jack-off sessions in the room where I stayed and would fantasize about being caught by my mother-in-law while stroking my hard cock to stupendous ejaculations that I had during my masturbation each morning before showering.
One morning while I was into my masturbation and not paying too much attention my mother-in-law made her way down the hall and I guess she heard what she thought was me getting sick, What she saw when she opened the door took her breath away! Me beating my meat for all I was worth! When she gasped, I opened my eyes and stopped stroking to see what she was going to do?
She stood there in the doorway for a moment, slowly smiled and said, 'I uh, I thought you were sick, but now I see that your just busy with yourself, I'm sorry for disturbing you!' I said, 'Your not disturbing me, I'm just doing what I do every morning before my shower.' Her eyes got a little bigger and she said, 'You do that EVERY MORNING?' I said, 'Yes, I do.' She then said exactly what I
wanted her to say, 'Then you won't mind if I join you and watch will you?' 'Of course not, but only if you lend a hand if you know what I mean.'
She said, 'Give me a minute to put a little something special on to help you.' She went down the hall and was gone for only five minutes when she came back, she slowly opened the door and came in wearing a robe. She walked over to where I was sitting on my knees on the floor and opened the robe to reveal a push-up bra, a lace garter belt that was holding up some black seamed stockings with reinforcements at her toes and heels and all topped off with some tall gloss black spiked heels that had open toes!
She whispered, 'Now, I want to watch you masturbate your hard cock while I sit here at the desk, O.K.?' I just leaned back on my left hand and started to jack off again with my right while she put her chin in her hand and smiled while watching me go faster and faster.
She told me that she enjoyed watching me jack off for her and asked if I would tell her before I was going to ejaculate?
I was going as fast as I could now so she just looked at me and said, 'Go ahead and masturbate that cock for me, Albert, masturbate for me as fast as you can! but don't forget to tell me when your going to cum!' A few minutes later I said, 'I'm going to cum!' and she took off one of her shoes and put it in front of my cock while telling me to shoot my cum on her toes! When she felt all the warm jizz covering her feet, she squeeled and laughed at me. 'Your SUCH a good masturbator honey, please tell me that you'll do this for me whenever I want!!'
That was the first time she watched me jack off, but certainly not the only. After that we got into a daily routine where she would come into my room just after her daughter and husband left for work and sometimes she would command me to masturbate for her while she watched and instructed me, and sometimes she would masturbate me with her delicate hands and lot's of lube until I covered her hands and fingers in warm semen so she could rub it into my stomach or if I asked, she would allow me to cum on her large titties while laying on the bed and she would get on her knees right next to the bed.
It was very enjoyable to have her instruct me how she wanted me to masturbate for her and sometimes she would put a finger up my ass and massage my prostate, That really made me shoot great strings of cum and she liked that too. This went on for many months until I married my girlfriend.
Even after our marriage, one time when we found ourselves in the house alone for a few hours, she instructed me to masturbate for her over and over until I was pumped dry, She had me shoot a load on her hair, and finally on her feet!
I begged her to let me stop, only after I promissed to do it for her again did she allow me to stop.
I became addicted to masturbating for her as she would always whisper to me when I saw her: Did you masturbate for me today?
More about my Mother-In-Law in another story.