I have known Annie for about 23 years. I met her when I was 28 and she was 15. She was a friend of my little sisters who is 14 years younger than me. We never really talked much except for the casual hello if I saw her at a family picnic or party. When I was 40 she stopped into my bar with my sister one night and we talked for about two hours while my sister flirted with some guy at the bar. I couldn't believe how much we had in common in our lives. I got married, had three kids and then got divorced because my ex was cheating on me. She was in the same situation with one kid. Anyway, I asked her for her phone number so we could talk again.
After about two years of talking about all of the crap that had happened in our personal lives we began to get very comfortable talking with each other about everything and anything including sex. We even admitted to each other that we both masterbated from time to time. For me it was more like every day but I didn't want her to know that. She would ask my advice about what guys did and didn't like and I would do the same with her about women.
One day I had seen an add for a health club subscription and it was giving 50% off if two people joined. I needed to loose about 50 pounds and Annie said if she didn't drop 40 she was going to lose her boyfriend because he was hinting she was getting a little 'Thick'. She said 'The heck with the health club, I've got a tread mill, elipticle and an exercise bike in my basement that I've been using for clothes racks for the past year. Why don't you just come by my house if you want to get serious about working out and we can motivate each other.' I figured I'd give it a shot. What could it hurt.
After about six months we both lost weight but Annie wasn't happy with her progress. I told her women always have a tougher time losing weight than men do and she should just hang in there. With that I went into the bathroom and took a shower. She decided to keep riding the bike. After my shower I had on a loose pair of sweat shorts and a tank top. Annie was still riding the bike. I was tired so I lay down on the couch to try and catch a nap. Annie finished her workout and went into the bathroom to take a shower. When she finished she came out of the bathroom wearing a white robe and sat on a chair by the couch. She was obviously aggrivated so I asked her 'What's wrong?' She said 'We've been friends for a long time. I need you to be real honest with me.' I told her I would and asked 'What's up?' With that, she stood up and said do I look 'Thick' to you and dropped the robe onto the floor and stood there naked in front of me.
I couldn't believe what I was seeing. Annie is 5'5' and about 135 lbs. She has long brunette hair. Her pussy is trimmed nice and short with a little landing strip. Her tits are a large C cup that are very perky with silver dollar nipples and she has an hourglass figure. I was totally taken by surprise when she did this. I looked her over up and down and figured I better not say anything sexual or it would ruin not only the moment but our friendship as well.
I said 'If your asking me are you fat the answer is no. Are you a size four, the answer is no also. You don't have a fat ass, your tits are beautiful, your stomach is flat and you don't have any cellulite anywhere I can see.' As I'm describing what she looks like to her I can feel my cock start to get hard. I mean here she is standing naked in front of me and I'm talking about how hot her body is. Who wouldn't get a hard on!
She must of felt very good about herself after that because instead of putting her robe back on she just goes over to the chair and sits down. She goes on and on about what an asshole her boyfriend is. Now I feel the head of my cock start to stick out from the bottom of my shorts while I keep getting more and more aroused looking at her naked body.
Well she noticed the head of my cock sticking out from my shorts and she says 'If you need to take care of yourself by all means go ahead.' I almost died. I say 'What do you mean?' She says 'Come on, I know you masterbate and your obviously horny so if you want to jerk off, go ahead.'
Now I am totally blown away. Here I am this 51 year old man looking at this beautiful 38 year old naked woman and she's telling me it's 'OK' to jerk off in front of her. I have never felt so turned on in my whole life. My biggest fantasy has always been to masterbate for a woman while she watches me and now I'm going to get my chance.
Rather than whip my shorts off, I slide my hand down my waist band, wrap my fingers around my cock and start to stroke it inside my shorts all the while looking at her for some type of reaction to what I'm doing. She's talking about how he's so ignorant and she's not going to deal with any more bullshit from her boyfriend and that she's going to dump him. All the while she's telling me this I'm slowly stroking my cock inside my shorts staring at her body while she is sitting there. As I continue to masterbate, whether knowingly or not, she slowly starts to let her legs open up so I can start to see her beautiful pussy.
She goes on a little longer about how rotten he is and I say 'Annie, would it be all right with you if I take my shorts off?' She says that I can do whatever I want. It doesn't bother her at all. In fact, on the days she knows that her daughter isn't going to be home, she never wears any clothes. She loves being naked.
I stand up, take off my tank top and then drop my shorts. I am so turned on that my cock is sticking straight out further than I've ever seen before and it is oozing pre-cum. I lay back down on the couch and position myself so Annie can get a good look at the show I'm going to put on for her. I say 'Annie, forget about him, relax and don't let it bother you anymore.' She says 'OK, I'm sorry.' I tell her 'Don't worry, that's what friends are for.' She looks at me, smiles and says 'You mean Friends with Benefits!' I smile back at her and start to really get into stroking my cock for her while she watches me.
As I rub my cock I can see she is getting excited. She totally focuses on what I'm doing and picks her left leg off the floor and hangs it over the arm of the chair fully exposing her pussy for me to see. She takes her left hand and places it under her left breast. Then she takes her right hand and places it on her right thigh. I take my finger and wipe a large drop of pre-cum off the tip of my cock and raise it to my lips and taste it. I look into her eyes and say 'If you feel the need to relieve yourself, by all means go for it. Like you said, I know that you masterbate and if your horny, go right ahead!' She then cups her left breast with her left hand and starts to play with her nipple which is already nice and hard. Then she places the middle finger of her right hand on her clit and starts to rub it in a circular motion. She then slides her middle finger inside her pussy and lets out a huge sigh! I'm in heaven at this point. Here I am masterbating on a couch with a hot brunette watching me and pleasing herself while I do it.
She stands up, walks over towards me and lies down on the floor next to the couch. She picks up her leg and lays it on the couch so I can see right inside her pussy and starts to masterbate with me.
This is more than I can ever begin to believe would ever happen in my lifetime and I am in absolute exctasy. This is the most erotic moment of my life.
I continue to jerk off and from time to time taste the pre-cum from my cock. When I do that, Annie brings her fingers to her mouth and tastes her pussy juice. She say's to me 'When you cum, I want you to cum all over me.'
That sends me over the edge and I say 'I'm going to cum!' She says 'So am I! Cum all over me baby!' With that I shoot at least five huge ropes of cum onto her beautiful body. The first one lands between her tits. The second one shoots even further and lands right on her mouth. The rest of the cum shoots onto her stomach and almost on her pussy.
As I just finish shooting my last rope of cum she says 'Watch me cum for you!' She starts to moan intensely and starts rubbing her clit real fast and starts spraying all over the place. I have never seen a woman spray like that. It was an incredible sight and the most intense orgasm I have ever had.
I told her anytime she wanted me to masterbate for her she should call me and I'll come right over. She told me that her daughter is going away to stay with her dad next week for two weeks and if I want, I could stay by her house while she's gone. 'Then we can run around naked and masterbate for each other whenever we want.' Then she says 'I would also like you to use my toys on me so you can watch me squirt and I would love to stroke your cock and watch you cum!'