11:11am Anna CNFM

A few years ago I was going with a very pretty blonde named Anna. She had a secret I was not aware of. She always had difficulty climaxing during straight intercourse. She would fake a climax and was good at it. After a couple of weeks I noticed she always climaxed just as I did. I thought she might have been faking it. When I confronted her with my suspicions she admitted she was faking it. She said she would masturbate after I went to sleep or went home. She said she hardly ever reached a climax except by masturbating. I told her I would love to watch her masturbate. She said she had never told anyone about her problem and sure, as hell had never been watched while masturbating,

I told her that I started playing with my cock many years ago and I loved to be watched. She said she had never seen a man jack-off. After quite a bit of talking and pleading she agreed to a mutual masturbation session.

Only I had to go first while she was fully clothed and would be allowed to call it off if she felt like it.

Being an exhibitionist who loved to jack off I readily agreed. We set a date for the next Saturday night.

On Saturday afternoon I completely shaved my cock and balls and around my asshole as well. I wanted to be fully exposed in front of her. On Friday I had stopped at an adult bookstore and bought a bottle of Astroglide and a large flesh like dildo about ten inches in length that became bigger towards the base, it had a head about the size of a golf ball. I already owned a vibrator with several attachments. I packed everything into an overnight bag.

I showed up at her apartment about eight o’clock. I was wearing Levi’s and a pull over shirt and without underwear. I could be naked in about fifteen seconds

She was dressed in slacks and a sweater. It was going to take sometime to get her naked. I put my overnight bag away as I usually did. We didn’t mention what we were planning to do later. We had a few drinks she served dinner. We had another drink. I excused myself and went into the bedroom. I stripped naked, picked up my overnight bag and walked back into the living room

Anna was sitting in a rocking chair fully clothed sipping on her drink. I placed a towel on the sofa and sat down facing Anna. I sipped my drink as I removed the Astroglide from my bag. I poured some Astroglide on my cock. Anna didn’t say a word. She sipped her drink and watched as my cock got harder and harder. This was a strange experience for me. Here was a woman sitting in front of me that I had fucked several times. I had eaten her pussy and licked in and around her asshole. But, her sitting there fully dressed watching my jack-off was a real turn on. I knew nothing of CFNM at the time.

I almost came in the first couple of minutes. She didn’t say a word. Just sipped her drink with a strange little smile on her lips. I had to stop stroking as I was too close to shooting my load. I reached into my bag and pulled out the dildo. I spread Astroglide around and into my asshole. I put some onto the head of the dildo as well. I slid forward on the sofa and raised my knees towards my shoulders. My asshole was pointing straight toward Anna. She said something like “Oh, Boy, this is going to be fun” She took the dildo from my hand and rubbed the head of it around my asshole. She slowing worked inwards towards the waiting asshole.

Very gently she pushed the head of the dildo into me. Working it slowly in and out and rotating it she applied more pressure. I could feel the big head of the dildo go in with a little pain. After that the rest of it was easy. She pulled it almost all the way out and would ram it back in again. After a few minutes she told me to “hold it in” while she went to get something. She returned with a hand mirror, She handed me the mirror as she took over the dildo. She said, “Now you can see what I’m doing to your big asshole.” And man did it look big. My asshole was spread wide open as she pulled the big dildo most of the way out and then really rammed it into me as far as she could get it. The big and wide base was almost inside of me. I couldn’t believe my asshole could be spread that far open. It was a beautiful sight and it felt wonderful. Anna continued fucking my ass for about 15 minutes when she firmly ORDERED me to “jack-off while I fuck you”. This was new to me. I had never been in a submissive position before. Anna rammed the dildo in and said “Jack-off NOW!” I grabbed my cock and started pumping. In about 30 seconds I shot a load all over my face and chest. When my cock went limp she told me to take hold of the dildo and go to the bathroom and clean up.

More experiences with Anna and her girlfriend Rhea will follow soon.