This was just one of a few experiences with one of my favorite girlfriends
One night I when I was in college I was sitting at the computer looking at porn and jacking off. I had my instant messenger program up and running and a girl friend of mine popped up. I had been edging for a while and she asked what I was doing. I told her I was jacking off (which she knew I did all the time). She told me she was at her apartment just watching tv. She asked me if I wanted to come over. I told her I was really enjoying jacking off (I knew there was NO WAY she would be having sex with me) and I was trying to build up to an amazing orgasm. She told me I could come over and jack off, that it wouldn't bother her if I did. I resisted the urge to cum right then and there, put my clothes on and headed over to her apartment.
When I got there she was sitting on the couch in pajamas. I sat down next to her and watched whatever show she had on the tv. She said 'I am going to finish cleaning up the place. You can sit here and jack off if you need to'. I didn't wait one minute. I stripped down, sat on the couch, and continued stroking from what I was doing earlier.
I continued my edging not getting in a hurry to cum because I loved knowing that she could look at me any minute and see me jacking off, all while she was just cleaning up her apartment. This went on for a couple of hours (not exaggerating). She would keep checking on me to see how I was doing, always flashing me a smile as to let me know she knew I was having fun and she was glad I was having fun. After a while she went into her room, took off her pants and came back out showing off her panties. She knew I had a panty fetish and this really got me going. As she was still cleaning, she would lean and bend over in ways that showed off her panties just to tease me a bit. I was really building up a lot of cum and I started moaning more to show her that I was enjoying her show.
After another few minutes she went into her bathroom and came back out with a hand towel and tossed in on my lap saying 'I think you may need this here soon'. I stood up with my hardon pointing straight up, hung the towel on my penis and started chasing her around the room. She just laughed at how I was holding in the towel in place with no hands.
I laid back down on the couch and continued jacking off. This has been going on for at least three hours now and I have built up a huge load, and was still going.
When she was done cleaning, she announced she was going to go take a shower. I asked her if I could watch and she said sure. She had a clear shower door. I sat in the bathroom floor jacking off while she showered, we had casual conversation, nothing overly sexual, but the whole time I couldn't stop stroking while looking at her perfect black bush (she had some Italian in her).
She said she was getting out and asked me to go back to the couch, which I did. I went back to the couch and was just flicking my penis at this point. I was SOOOOO aroused that even stroking just a couple of time would have made it explode so I was very lightly touching, which was just enough to keep me hard and not cum.
A couple of minutes passed and she walked into the living room where I was at wearing nothing but a pair of panties. She said 'Are you still jacking off?'
I replied, 'yes, and loving every minute of it'.
'That is a long time to be masturbating', she followed.
I was still just lightly caressing my cock just to keep the urge built right up. She came and sat down on my legs while I was still laying on the couch. She stared right at my cock as I was still lightly touching it.
At one point I felt the orgasm about to happen and realized I was SOOO close to the breaking point I took my hand away and just laid it to the side, trying to catch my breath and will myself not to cum just yet.
Within seconds of me laying my hand down and TRYING to relax, Sara grabbed my raging cock and started a medium stroke. 'Is anything going to happen with this?' she asked. I could barely mutter a response when my hips started bucking, and moans were filling the air.
There was so much pressure built up that the first shot of cum came out and flew over my shoulder, over the armrest on the couch, and hit the window pretty high up. We both chuckled when we heard the splatter of my cum hitting the glass. She continued her stroke and milked every last drop out of me. The rest shot on my chest and stomach. This was easily the most powerful orgasm I had up to that point in my life.
She took the towel and cleaned up the mess I made as we just laughed about everything that happened. I have been back a few times and jacked off with her there. Sometimes she would help and sometimes she would just sit and watch, but she was one of the best girlfriends I had, and this memory will live on for a while.