She Was Up For Anything

This is a true story of my relationship with a woman that stretched over a few years. I’ve written previous stories of some specific activities with her, but this covers the whole relationship which was strictly a sexual one. The accompanying photo is her hand on my cock. A very common occurrence when we were together.  I originally met her through my wife. The woman, Sherry by name, was a hairdresser and did my wife’s hair. At some point she started cutting my hair. About a year after I initially met her, she split from her husband and right around the same time, my wife and I broke up. At this point there was nothing going on between us other than she was cutting my hair regularly. She had been coming to my house to cut my hair. My wife and I were still living in the same house although at opposite ends. We continued to share the house until we could get it sold. We had a huge amount of equity in it and the only way I could come up with her half of the equity was to sell the place. Sherry was an extremely outgoing person. Nothing really was taboo to her. We used to joke around a lot and of course there was always a certain amount of sexual innuendo in our conversations. One time when she was cutting my hair, I jokingly said something about my pubes needed trimming and she said, “no problem.” But she couldn’t do it at my house since there was always the chance my soon to be ex-wife would be there. She suggested that we do it after hours at the salon where she worked full time. I turned up at the appointed time. She had a key to the place. The chair I sat in was actually visible through the front window of the salon but only from the chest up. She cut my hair and then told me to take off my pants. Frankly I was very nervous about doing this. Suppose another of the employees turned up? She told me not to worry about it. I took off my pants and underwear and sat in the chair. She got busy trimming my pubic hair. I was really concerned about getting caught and as a result it as a very non-sexual event. I tried to imagine what might transpire if I got an erection, hoping that it would seem like a natural occurrence and I knew she would just laugh it off. Unfortunately my poor penis had other plans and stayed limp as a noodle  Shortly after this the house was sold and I moved out of the area. However, I wanted to continue the relationship with Sherry hoping it might develop into something more interesting. It was nearly an hour’s drive from where she lived to my new place, but I offered to make the trip worthwhile. At the time I was making a lot of money and had set up a relatively low overhead single lifestyle, so I was in a position to give her a couple of hundred bucks to drive to my place every few weeks. Back then, that was a fairly decent amount of money.  The first time she came to my new place she forewarned me to have a bottle of champagne on hand. It wasn’t for any celebration, it was just her favorite drink. She showed up at the condo and gave me a haircut. Then she told me to strip and she would give my pubes a trim. I took off all my clothes, sat down in a straight back chair and she started clipping away. Holding my dick in one hand and trimming away with the other. All the while we both were guzzling champagne. Now I really wanted an erection but maybe I wanted it too much because nothing at all was happening. The more I tried to will myself into a hard-on, the less anything was happening.  My new condo had a large whirlpool tub in it and we both decided to get in it. Sherry had a terrific body. Really nice tits, a narrow waist, flaring hips and the best pair of legs you would ever want to see. By now we had advanced to some serious kissing and cuddling. She even rubbed my cock but nothing happened. I couldn’t believe I couldn’t get hard. That was never a problem with me but there was some kind of mental block going on.  Finally, about 1 am we decided to go to bed as she didn’t want to drive home after too much champagne. We got into bed, both of us naked as jaybirds and still nothing happened. I’ve never been as sexually frustrated as I was that night. However, I woke up with a glorious case of morning wood. My dick was so hard a cat couldn’t scratch it. There was never any question as what to do with it. After some really hot and heavy foreplay, I slid my rock hard cock into her sopping wet pussy and fucked the shit out of her.  That was the start of a nearly two-year fuckbuddy relationship. It was somewhat unusual. She loved to watch me jack off. But she also loved to jack me off or suck me off. Plus plenty of fucking but as I think back, I believe we both somewhat preferred masturbation. I think it had something to do with her love of watching me ejaculate. She really got off on it. To the extent that when a visit was planned, I would edge for a large number of hours so when the time came for me to jack off for her, I was loaded for bear. The first time we did this I really primed the pump, and when I came, the semen shot halfway across the room. It went so far that I had her get a tape measure out of the kitchen drawer and measure it off. Just an inch or so short of five feet. Even with just a normal jackoff I could usually spurt a good two or three feet. And those hand jobs were usually just the beginning of several hours of fucking and sucking.  One time she brought a girlfriend with her. Sherry had told the friend about how far I could shoot, and the friend didn’t believe it. She wanted to see for herself. They showed up with no warning but fortunately this was one of the times I had done some serious edging. I didn’t do it every time she came but luckily I was prepared on this particular visit. I jacked off while the two girls watched. The friend was blown away when the semen started flying across the kitchen floor. Sherry dutifully got out the tape measure and once again it was just short of five feet. Afterwards, as I stood there, slightly embarrassed as the only naked person in the room, strings of cum drooling from my dick, I felt really exposed. But both the girls were totally cool as they discussed my performance as if I wasn’t even there. Sherry grabbed a washcloth and ran some warm water over it and came over and wiped off my cock as if it was the most normal thing in the world. Sadly, that was the only time the friend was there. I had kinda hoped for a possible threesome but they girls said they had to get going.  From time to time, Sherry would hook up with a boyfriend. During those times she still came to cut my hair regularly, but our sex was limited to handjobs and blowjobs. She would not fuck me while she was seeing somebody. I remember one time she was in a big hurry. She did a quickie on my hair and said she only had time to suck me off. I had gotten in the habit of being nude while she cut my hair and usually had a hard-on the whole time. I asked her what was the big rush and she said her boyfriend was waiting in the car outside. While she knelt down and started sucking my cock, all I could think about was the boyfriend outside. That didn’t inhibit me from shooting a load of cum down her throat however. One time she came to my place (no boyfriend at the time) and spent nearly the entire day. We got undressed and were both completely naked for the next five or six hours drinking champagne and having various forms of sex. At one point we went out on my balcony. At the time I had a third floor condo. The balcony was not in view of anybody. There was a thick forested area across the street. She decided she wanted to jack me off and she wanted me to shoot my semen off of the balcony. Who was I to argue? We scooted our chairs up closer to the railing and when I came, it spurted out right between the railings and sailed off the balcony. After she finished coaxing every last drop of cum from my cock and sucked it clean, I looked over the edge of the balcony. The unit under me had an identical balcony to mine but the ground floor unit had a landscaped patio. There was an outdoor table and chairs and right in the middle of the table was a big blob of semen. She thought it was hilarious but I was a bit concerned because whoever lived there would know it had to come from me or the person below me. Nothing ever came of it however.  One time I took her on a short vacation to Mexico. We stayed in a town on the tip of Baja called San Jose Del Cabo. Several crazy things happened on that trip. She was very uninhibited normally but once in Mexico she really let it hang out. I had rented a Suzuki Samurai which was an open Jeep-like vehicle. We were driving from Cabo San Lucas to San Jose Del Cabo, the two main towns at the tip of Baja. She decided she wanted to suck my cock, so she got it out and went to work. We passed several slow moving trucks filled with workers in the back and they all were screaming and yelling at us she bobbed her head up and down on my prick as we drove by.  We were staying in a very upscale resort called Palmilla. We had a ground floor room with a really nice patio. Late at night we would lay out on a couple of chaise lounges. On this particular night I moved over onto her lounge and started playing around. The clothes came off and pretty soon I was laying on my back while she straddled me with my cock buried in her cunt. Both of us totally naked. She’s bopping up and down when I heard voices of several people. There was a path that went right by our patio. I whispered for her to lay still until they passed by. She kept right on humping and I heard the voices change to whispers. I looked past her and two couples were watching us. They stood there transfixed for a few moments while she slammed her pussy up and down on my cock. Then they moved on just when I started pumping a load of cum into her.  The next night we had a very late night dinner in San Jose del Cabo. We got out of the restaurant around 11:30 and decided to walk down the totally deserted main street of the town. After walking for 20 minutes or so, I had to pee really bad. Nothing was open and by then the restaurant was probably closed. Sherry said, just go over in that darkened doorway and let it go. She walked with me. When I got to the doorway she stepped up behind me, wrapped her left arm around me and reached for my cock with her right hand. “Here, let me hold it for you,” she said. I relieved myself while she directed the stream. When I finished she flipped it a few times to shake it off and then started to masturbate me. I was instantly hard and she proceeded to jack me off. It was a really satisfying orgasm as I shot my cum all over the sidewalk. Something about getting jacked off in a totally public setting, even though nobody was there but us, was very exciting.  Sherry moved to Arizona and although I saw her a couple of times on her rare trips back to L.A. to visit family and friends, I had hooked up with the gal who would shortly be my wife and completely lost touch with Sherry. But we did have a lot of fun together. I have to laugh about that initial session where I couldn’t get hard to save my ass. Every time after that when we were together it was instant erection. In fact, she used to tease me about my cock seemingly being hard 24/7.  ###########