Older & Timid

I had been living in Utah about 6 months or so and had gotten a job working with people with disabilities. I was making a good living considering I was in Utah, and I was finally able to find my own place. It wasn't Taj Mahal, but I rented a small little 1 bedroom cottage not far from the main highway. I was doing alright, meeting girls, getting laid and having a great time. My folks still lived down south about 20 miles and I visited often. There was a small store & gas station across the street and one day while I was in there I met the sister of one the counter girls.

Stephanie was in her late 40's or early 50's. She had long dark brown hair with streaks of grey, and had just moved to town. She wasn't bad looking for age but she was no beauty queen either. She weighed about 150 lbs, which on her frame was about 20 lbs too much. Her body wasn't the best either and her clothes didn't help. She had a big ass, a thick waist and double A tits and her self esteem was in shambles. It seems she was living in Northern California but was in the process of divorcing and need to leave town to clear her head. By the time she arrived her marriage was over and she was depressed. After about a week decided she was going to stay. She told me she was staying with her sister but they really didn't get along very well and she was now looking for her own place.

Stephanie & I got along well and it wasn't long before we were hanging out and doing things. She had a smile on her face and seemed happy that someone wanted to be around her. I tried a couple of time to get into her pants but she wasn't having any part of that. She had lots of reason that never seem to make any sense, from our age difference to the gossip in our little to the fact that she was still married. I sort of figured I might get into her pants sooner or later but was getting laid so much that it really didn't matter.

It didn't take me long to get my place looking good. A few cans of oops paint from the hardware store, a few pictures on the wall and some curtains and candles & I was living in bachelor heaven.

One night, after a long day of work and some fishing, I was tired just getting ready for bed. The lights were out and only a couple of candles were lit when I heard a knock on back door. It startled me a little cause it took some effort to get to the back yard without going through the house. When I open the door there was Stephanie and she was asking to come in. I was a sort of surprised to see her as it was so late but she mentioned that I had invited her over to see my new place and since she was in the neighborhood there was no time like the present. As I wasn't expecting company, I answered the door in a pair of boxer and at first she seemed embarrassed and asked if I always came to the door with so little clothing on. I told she was lucky cause I was in bed and usually slept naked. Then she looked down and blushed, and when I looked down I was getting hard and poking out the front.

I didn't really have to ask her in; she just pushed her way through. I told her to have a seat on the couch and make her self comfortable and I would put some clothes on and I turned to head towards the bedroom.

The house was set up kind of weird. If you came through the back door, you came through the kitchen, into the living room, past the bathroom and the bedroom was located in the front of the house. So as she came in she got the tour. I asked her if she wanted something to drink but she just followed me through to my room. She was real impressed by the way I had decorated and by the time I got to my room she told me not to bother getting dressed. When I turned to ask her why was already down to her bra and panties. They weren't exactly the sexiest pair of undies, in fact they were the more grandma/industrial type that covered everything. But I could tell it really took everything she had to strip down and be this brave. I was shocked to say the least because after trying for so long to get her bed I sort of gave up. And now here she was giving her self to me. She told me I could have her but made me promise to tell absolutely NO ONE! She was so afraid of anyone finding out hat she actually parked 2 blocks away and snuck into my yard. I peeked out the window and I didn't see her car.

She was very timid at first and I tried to get her to ease up. She was very different from the girls I was fucking already. Most of my regulars were horny animals who did as much fucking of me as I did of them, but Stephanie was different. She was sort of used to lights off, get naked in the bathroom, missionary position Wham Bam Thank you Mame kind of sex! So I casually moved her to the couch where we did a little necking. She took the rest of her clothes off but asked if I had a robe. I went to get it for her and she quickly put it on. As we sat on the couch she slowly started to kiss me and caress me, but not on any of my erotic zones. She was rubbing my leg and kissing my neck and when she finally reached my crotch she seemed almost hesitant. I still had my boxers on and when she felt the front of my boxers I was already poking out and very hard. It scared and she pulled her hand back. When she looked down her jaw dropped and sort made a comment about how big I was.

This time when she reached back she got her self a good handful and was really rubbing me good. In fact I had to tell to lighten up cause she was going to rub me raw. She was real nervous and said it had been a while since she had a dick in her hand. In fact this was the first dick she had seen in a long time. For an older women, she really didn't know what she was doing. Kind of a shame really cause she played the part so well. She was clumsy and awkward and really seemed to working to hard to have a good time. I finally told her that we should move things o the bed and although she agreed I almost had to pull her to her feet and drag her. I asked her more then a few times if she was sure she knew what she was doing and I tried to give her an out if she needed one. She never really said, "No, please stop! But she never real made me stop.

SO I laid her on the bed and did my best to put her at ease. I kissed and licked all the spots I know women love but she was having none of that and she closed her legs on my ears before I could get close. I then tried to get her to give me a little head but she just put the tip in her mouth and was done too fast. Fuck I love foreplay, especially eating a girl till she's ready and I love getting head but none of this was happening. I was feeling like maybe, as scared as she was, that this was as far as it would go. I mean if I can't get you wet, how am I supposed to slide in. I didn't even have any jelly or lube. But she got on her back and pulled me to her laying my dick across her furry opening. When I did I got the shock of my life, she was wetter then any women I had been with I quiet a while. She dripping wet. She was soaking the hell out of the sheets wet. She looked me in the eyes and said that she had made her mind up earlier in the afternoon to come over and fuck me, and when she finally made up her mind she said got so wet. She said it was running out of her and she had to change her undies and her pants at least 4 times that day.

She tried to put me out of her mind because she didn't feel she was ready to get involved but her pussy was now doing the talking and she was listening. I put the head right at her opening and she asked to go slow. You know it's really hard to go slow when you come across a pussy that wet and calling your name. It seemed like it took me forever to get in and hit bottom and when I did she just stiffened up and told me to hold still. She said she wanted to get use to my size but she was cumming before I could even start to move around. Heck she was in love so fast and was cumming so much and I hadn't done a thing but put it in her. Then her ass started to wiggle and she gave me the go ahead to start fucking. She wrapped her legs around my waist, put her hands around my neck and just hung on.

I started slow at first as I didn't want to hurt or scare her but before you know we found a nice rhythm and were really going at. Although her experience was limited you could tell she had the making of a real tiger in bed. I'm pretty sure she was looking for someone to bring that out in her and I was doing my best. It was almost scary how tight she hung on but I never stopped feeding her my dick. All of a sudden she got real quiet and then started to cry. I was afraid I hurt her so I pulled out and lay next to her. When I did a gusher came streaming out of her. She wasn't really shooting & squirting but just flowing. I asked her if she was OK and she said in all her years of having sex, no one had ever made her that wet or made her come like. I said, "Even when you masterbate?", and she said she had never done that. I know she had an older son, so I know she wasn't a virgin but damn close.

I hadn't come yet so I jumped back in the saddle and started to slide back in and as he was shocked that I wanted to fuck again. It seems her boyfriend was a 30 second man and she never got seconds. Damn was she wet, and it didn't take me long to fill her up with cum, and she was cumming again herself. Wow was she wet. In hindsight it's a good thing I didn't eat her, I would have drowned. After I was done I tried to get her to stay by telling her that if she gave me a few minutes I would be ready to go again in no time but she said she was sore and since it had been a while she didn't want to cause herself any irritation. I was used to longer sessions and was kind of worked up still. But she got dressed, gave the best kiss she knew how to give and promised me she would stop by another night.

The funny things was she was true to her word and came to see about 2-3 times a week and she always came by late at night and through the back door. She really learned her lessons well and really learned to enjoy sex. But the funny part about the whole deal was I became her booty call, her 11-5 and no one in town was the wiser. It eventually ended one day when I was in that little store and her sister started peppering me with questions. I tried to ignore them or divert the conversation but one I could take it any more and when her sister asked me for the 300th time if I was fucking her sister, I turned and told her no, that she was fucking me. Well word got back to Stephanie and I never saw her in my bed again. I still see her at that little store once in a while with her new husband. She always has a little smile for me, kind of like an unspoken thank you and her new husband is none the wiser, although I'm sure he's grateful knowing his wife is a tiger in bed.