Carla & I

Recently, I have found myself in a strange position in life. After working for many years for a large well known company, our division was shut-down and I was told I would not have a job after November. Additionally, my live in girlfriend of 6 years broke up with me and moved out. We had drifted apart and for a while were two people living in the same house, sharing a bed, but living separate lives. This was not a surprise, but she paid half the mortgage on a townhome in my name I would never be able to sell with the current real estate market. She had some medical issues and the medications made her gain a lot of weight and lose interest in sex. Her self-image was very low and our sex life went from once a week to once a month to never. I spent a lot of nights masturbating while she slept.

Last fall; I got run over by a car, breaking both my legs. There is a group of people from my office who go running at lunch; we were waiting to cross a laneway on the office property when the car tried to exit on the wrong side of an entrance and had to go onto the sidewalk to avoid a UPS truck coming up the lane.

The guy who ran me over was rich, well insured and was just returning from a liquid lunch with some of our executives. I am now on an indefinite medical leave and should be getting a nice check in the near future.

I realize now that this was the best thing to happen to me. With the exception of 3 weeks in the hospital of course.

This has allowed me to be at home all day and I have an exercise program building strength in my legs. I walk 2 miles twice a day with my dog. The dog walking is how I met Carla.

Carla lives in a house directly behind mine, but I have to walk almost a full mile, down a very long block, to go door to door. We met in the small dog park near our homes.

She is a bit older than me and has 3 children, but lives alone. I was told from another neighbor that her husband is an airline pilot who works overseas, but they don't see one another anymore. She has never spoken to me about him.

I don't know exactly why, but I don't find her sexually attractive. She is a larger women, not fat but curvy. She has thick long black hair, almost to her waist, brown eyes and olive skin.

What started this thing was a conversation we had one day at the park. I forget how it started, but I made a lame joke about how we both needed to get dates and should go on e-harmony. Carla replied she did not have the time and only wanted a man for 20 minutes. I replied that she needed to try craigslist. Carla gave me a very strange look and asked what that was. I explained that it had personal ads for casual sex.

Several days later, again at the dog park, Carla approached me and asked if I had ever looked at the ads on craigslist. She wanted to know what all the codes mean. I did my best to explain and she seemed shocked. The one that got her attention was 'jack-off-buddy'.

Out of the blue she tearfully told me she just wanted somebody to be there to watch her masturbate. I did not know what to say. Clearly embarrassed, Carla quickly left me alone.

The following day, Carla called over the fence and said she wanted to talk to me, suggesting I come over for coffee. I agreed, not knowing what to expect when I got there.

Carla had coffee ready and seemed nervous. I tried to put her at ease by saying I understood her situation and told her about my relationship with my ex-girlfriend, without getting into too much detail.

We spoke for a while in very general terms about how often we masturbated. After a moment she stood up and asked if I would like to watch her masturbate, but made it clear that we were not going to have any sex and that if I tried to she would ask me to leave.

I said ok.

We went into her bedroom and she sat me on a chair at the end of the bed. When she was naked, she took a large latex dildo, shaped like a cock, from under her pillow. She sat on the corner of the bed, feet flat on the floor, legs spread as wide as she could, slowly inserted the dildo into her very hairy vagina. I was amazed at the size of the dildo. My girlfriend had a vibrator that was much smaller and had to use lube to get it inside her. Carla just took this inside her easily.

The whole time she was talking, telling me what she was doing, and what it felt like. After a moment she had opened up and was taking the entire dildo faster and faster. From where I sat, about 6 feet away, I could hear the slurping noise as Carla pumped it into herself. Suddenly, she gasped, 'I am almost there' and leaned back onto the bed with her legs up in the air, still pumping the dildo in and out furiously.

I had never seen a woman squirt before. I had always thought of it as a myth, but I clearly saw Carla squirt, leaving a huge stain on the bedspread. She rolled onto her side and drew herself into a fetal position, breathing heavily.

Carla sat up and the dildo slipped out of her vagina and fell to the floor. Carla picked it up and with a tired smile on her face, said she wanted to be alone for a while and could I see myself out.

It was an incredible experience and as I was walking home I realized I had ejaculated at some point. As soon as I got home; I jerked off.

I did not see Carla again for almost 2 weeks, but we met at the post office. I asked if I could see her again and she said to come over that afternoon.

She met me at the door in a robe with nothing on underneath, explaining she could not wait and was 'warming up'. Again I was placed in a chair, away from the bed. This time Carla lay in the center of the bed, her hips on a pillow, and slid the dildo into herself while rubbing her clit.

I took my penis out and started to masturbate along with her. When Carla realized what I was doing she got upset and asked me to leave. Once I was outside she came to the door and said she was sorry and we went back inside.

We spoke for a while about what each of us wanted, told me it was ok to jerk off and she then lay back on the couch and began fingering herself.

I waited until she had come before taking off my pants and quickly masturbating. As I got close to coming, Carla told me to come on my stomach, so I did. I walked home with a big semen stain on my shirt.

We now have an agreement that I use a condom when I go over to her home. The deal is that I put one on as soon as I get hard and clean up as soon as I come. I have since realized she has a strange aversion to semen. Frankly; my masturbation is something she tolerates, she has told me she really does not enjoy watching me as much as I enjoy watching her.

We get together twice a week, sometimes more often, sometimes less, it seems to depend on Carla's cycle. Over the past month or so she has relaxed somewhat and once we lay together on the bed, side by side as we masturbated.

I am not sure if I want to continue this relationship for the long term. I have started dating again and since this thing started had had sex with two other women. When I told Carla about going to another woman's home for the night and having sex she gave the impression that I was 'cheating' on her in some strange manner. On the other hand I enjoy our times together and like to get off while watching Carla fuck herself with the big dildo.