Diana's Story

(copyright, March, 2002)

1 – Me

My name is Diana Roberts. I am 48 years old. I live in a large metropolitan area in Canada. I am married but no longer living with my husband, and I have two sons, Robby, who is 23 and who is currently attending medical school here in the city we live in, and Toby who is a year and a bit younger and whom I haven't seen in a while.

My husband's name is Bob and we had been married for over 20 years when Bob decided he no longer wanted to live with me. He reconciled himself to the fact that he was gay and decided he wanted to spend the latter years of his life living in that community and doing what he felt he should have been doing all along. Bob was very successful financially, and he currently supports Robby and I very well. I had only found out he was gay about four years ago, and while I had suspicions at times, I was quite surprised and hurt that he had been having affairs with men for a number of years without me being aware of it.

I believe I am still a fairly attractive woman at 48. I am well built and I keep myself in good shape by working out regularly at running and aerobics. I am tall and I like to think that my weight is proportional to my height, but that is a little optimistic, I suppose. Like most people I have to watch what I eat to keep my weight under control and that has been a little harder to do since Bob left since it is hard to get up the energy to cook the right food when I am alone. It is easier when Robby is home. I think my bum is a little too wide and that my breasts are a little too large, and that has always bothered me a little, but one learns to live with those kinds of imperfections. I am also noticing that the aging lines around my eyes and mouth are becoming more noticeable with time, but what can one do except make the best of it. My hair is long and dark and I usually wear it down over my shoulders. My eyes are green and they sometimes take on a pale sea green color in certain lights, something people who know me have mentioned several times. I belong to a health club and I try to get there to work out at least four or five times a week. It has also become sort of a social outlet for me and I have met many wonderful women there, several who are in the same boat as I am, divorced and about my age. After we work out or take a class together, we sit around and chat, exchanging stories about our husbands and life in general with and without men.

As I said, I have rather large breasts for my body size. My breasts have always been quite firm and shapely, although lately a number of blue veins are starting to show more and more through my skin. My nipples are not overly big but the brown area around them is sometimes quite prominent. Lately, they have been starting to sag a bit, and I guess that age is catching up with me. I also have pretty good legs and I have always managed to attract attention from other men, although I was always rather put-offish to them and never once did I ever invite an advance from any of the men who tried to flirt with me over the years.

Our sexual life was never an exciting one. We did have sex on a regular basis, but when I think back, I now realize that Bob was very selfish about sex and only seemed to want oral sex, and only one way. He was always quite content to have me suck his penis whenever he wanted me too, and while it didn't happen every day, when he wanted me to do that for him, he was very demanding about it. He seldom touched me and we seldom had intercourse together. He would always want to ejaculate into my mouth and once he was finished doing that, it would be the end of our sexual encounter, even though I tried to get him to please me too. That should have been a clue, I guess, but not having had much experience prior to our marriage, I guess I was too naïve and accepting of things.

So, you can see that my life has been pretty mundane for quite a few years, and because of the relationship with my husband, I never thought much about sex and thought that this kind of relationship was just the norm for folks of our age.

When Bob left me, I looked for some work for a while, but at my age, I was unsuccessful in getting any. I did not have to work and I had enough money to support myself, but I thought I should work anyway to keep myself occupied.

I did buy a computer soon after Bob left and with the help of my son I learned how to use it and became quite efficient with it. I don't know what it was or why, but I seemed to come by its use quite naturally and I soon found myself signing on to the internet and locating different web sites. I have been enjoying it immensely.

I was soon exposed to a whole world of weirdness and interesting stuff while surfing and playing around on the net. I had heard about porn and stuff being a problem, and I guess I was a bit curious to find out what all the fuss was about, so with a determination I didn't realize I had, I signed on to and tried out all kinds of sites. I got an e-mail address and I found chat sites, catalog sites, picture sites, and everything else there is on the net.

I could not believe that there was so much sex going on around me. As I mentioned earlier, my sexual experience had been pretty much limited to Bob and then limited in general. Now, the more I learned on the net, the more intrigued I became by what I might have been missing. And boy, had I ever been missing a lot. I couldn't believe what I could see and hear and do with my computer when it came to sex.

I had always had a sort of sub-conscious interest in high heel shoes, although I never owned any really high ones. We always dressed rather conservatively and my highest pair of heels was probably only about 2 or so inches high, but I was always fascinated by other women I saw at parties or out shopping who wore much higher heels. I recall when I was quite young that I used to sometimes try to walk in my Mom's heels when she was out. And when I went shopping for shoes, I often found myself looking at the very high heeled ones and wondering what it would be like to walk in them, but I never got up the courage to buy any. I soon found that there were all kinds of mail-order web sites that sold shoes, and I then found myself thinking that maybe I should order a pair after all these years.

After searching for quite a while, I settled on a pair of red open-toed sandals that had a very high heel. They looked so pretty and sexy in the picture and when you read the description it sounded like they were guaranteed to attract the first man that saw them. I also got very brazen and decided to order a red and black garter belt and some black fashion stockings with seams. The garter belt looked very sexy and it had five straps on each leg that attached to the hose. I had never worn a garter belt in my life, so you can imagine how excited I was when I settled on the one I wanted. I was nervous about providing credit card information but soon got over that and placed an order.

I was as nervous as a schoolgirl on her first date while waiting for that first order to arrive. It only took two days, and then I was afraid to answer the door when I saw the express truck parked in our driveway, as I thought the driver probably knew what was in the package. I was nervous and embarrassed but then pleased to find out that there were no markings on the package to indicate what was inside.

I couldn't wait to open the box when the man left, and I was delightfully surprised to find exactly what I had ordered. I immediately went up to my room, undressed totally, then put on the garter belt and stockings and then the shoes. The shoes I ordered had heels that must have been at least 5 inches high, and I probably should have ordered something lower for my first pair, but I was determined to learn how to walk in them, no matter what. But that was harder than I thought, and I found myself tottering and having a lot of trouble, not to speak of the sharp pains that shot through the calves of my legs. I couldn't stand in them for very long because of the pain, so I sat on the edge of the bed looking at myself in the mirrored doors of the closet.

Imagine a woman approaching 50 looking at herself in the mirror with her legs open, wearing only a garter belt, hosiery and with a pair of 5 inch heels on her feet. For some reason I felt very sexy and attractive, and then I started to run my fingers over the stockings and the open part of my legs above the tops of them and over my breasts. I hadn't felt much sexual yearning for a long time, and I had seldom masturbated but now I could not stop myself. I started to play with myself and soon found myself moaning with pleasure and it wasn't long before I had one of the nicer orgasms that I could remember.

With practice I soon learned to walk in the shoes and it wasn't long before I could keep them on for quite a while. Whenever I was alone in the house I would undress and put my heels and the garters on and with the blinds drawn, I would do my chores or sit at my computer dressed like that. It wasn't long before I ordered other pairs of shoes and several other bras and things. I was becoming obsessed and tried to find the sexiest types of bras, camisoles and even some corsets and girdles, all with straps to hold up the stockings I ordered, since I found it so refreshing not to be enclosed by pantyhose.

My feet are very easy to fit and ordering from the net has worked very well for me. The big advantage of buying this way of course is the incredible variety of styles that are available and I have been able to get myself several pair of very exotic shoes. One problem is that I only wear them around the house when I am alone as I am still not comfortable wearing some of the more exotic ones outside of the house. Since being on the net, I have also come to realize that my interest in my shoes and hose would probably be considered a fetish by many. It was not long before I had about a dozen pair of shoes, and I even ordered some long high-heeled boots that I enjoy wearing very much also.

My first pair of boots were a vivid red and they had a 4 ½ heel, a zipper that ran right down to below the ankle, and they were trimmed with red leather straps. The straps were mainly for show I think, although they could have been adjusted. I much preferred to leave the straps at the top of the boots behind my thigh very loose so that the top of the boot was as wide as possible. I guess I just liked the look of my leg coming out of the wider top. I enjoyed wearing those boots so much and I enjoyed looking at how I looked in the mirror when wearing them that I ordered several other pairs as well, some in very soft leather, and of course I just loved wearing the leather ones since they looked and felt so much better.

I think that one of my very favorite things to wear is a white bustier type of outfit that I bought one day. I like to wear it around the house with white hose and a pair of platform sandals with extremely high heels, but heels that I could at least walk in because the high platform soles did not make the heels quite as high as they looked. This outfit only had an under-wire platform bra so my breasts were bare when I wore it, and the tiny cup held them so that they stood out quite firmly. The neatest thing about the outfit though was that the garter straps were very long and attached about half way up my body, not from my hips where they are usually attached, and they were quite stretchy. This gave them a very different effect and when I walked the garter straps would pull away from my body. I loved to put this outfit on and strut in front of a long mirror, looking at my body, my breasts and my legs especially. I seldom wore panties when I had this outfit on so except for the garter straps I was bare naked from just above my navel to the tops of the stockings that stopped half way up my thighs. I absolutely loved the feel of the material against my skin. I called it my virginal vamp outfit and believe me when I say that I have masturbated more than once while wearing it.

One day I even decided to order a dildo. I thought that if I was going to masturbate once in a while, I might as well try a dildo too. I actually ended up ordering two of them, one that was plastic and had a battery so it was really a vibrator I guess. And then one that was rubbery. I don't know what I was thinking but the rubber one turned out to be so big that I could hardly get it into my vagina, no matter how much lubricant or how relaxed I tried to make myself. I still enjoyed it though because I would play with it once in a while and lick it and pretend it was a real penis. Whenever I did this, I felt pretty silly but I did enjoy it a lot.

One problem that I had though was making sure my son would not see this new stuff so I kept everything locked and hidden in a small trunk I had in my bedroom. My son was studying at university and had a girlfriend that he lived with most of the time, so he was seldom home but I did have to be careful, because he still had his room and he did come home to use it every once in a while.

Anyway, it became almost a daily ritual for me to have a shower in the morning, then put on a girdle that perhaps had a half bra and a pair of my high heels or boots. I would then prance around the house like a tart with my breasts jutting out over the top of the bra that was holding them up and feeling like a stripper on the runway. Seldom would a day go by that I would not masturbate, and sometimes I would do it two or three times a day.

2 – My Chatting

I had found some chat rooms that featured a lot of cyber sex and used to spend time there when using my computer. I really didn't like cyber sex very much, but I must confess that I did try it a few times, and even found myself masturbating while engaged in some sort of silly scene with someone I had never met. I don't know if they believed me when I told them what I was wearing, but I did enjoy sitting at the computer with my new shoes and clothes.

While I did not enjoy the cyber very much, I did enjoy chatting about sex and finding out what other people thought and did. Once I realized that people were more candid than they might be in real life, and that the person at the other end could not possibly find out who you really were, I became more comfortable in sharing and listening to fantasies about sex. Sometimes, I would become aroused enough to masturbate while I was chatting with someone.

Then there were the pictures. Oh my, so many people wanted to see a picture of me and of course a lot of people wanted to send you pictures of themselves. I did scan some shots of myself that I had, but when I got brave enough to send one to someone, more often that not they would want to have one of me naked or something. I visited a lot of sites that showed pictures of ordinary people in all kinds of dress and undress and even having sex, and I often thought that I looked much better and had a much nicer body than most of them. I also thought it might be neat to have some pictures of me in my heels and hose, and I even found sites that offered to take the pictures. I ended talking to one man who lived not very far away and he offered to take photos of me in some of my outfits. He said he would do it for free, and finally one day my need to do something like that got the better of me and I agreed to pose in some of my clothes. Now I have a whole bunch of photos of myself in very sexy poses and many with my breasts bared but that is another story and I am getting away from what I want to write about.

One of the things that intrigued me the most were the pictures that I found of women in various forms of bondage, and I found myself looking for more of these types of pictures all the time. I became very intrigued and curious about this whole sub-culture of activity. I didn't know much about it and didn't even realize that people really did this, and soon I found myself interested to the point of wanting to try it myself. I cannot explain it but the very thought of what it would be like to be tied and bound in various ways like the women in the pictures, and maybe to even be tortured and abused became very erotic for me. I don't know what caused this interest, but it started to become an obsession and I found myself thinking about it and fantasizing about it on a constant basis.

I then found myself masturbating while looking at pictures of women tied up and being tortured, and wondering what it would be like to be in their position.

I saw a number of pictures that featured women with things that I have since learned are nipple clamps, and this intrigued me a lot. The thought of those on my breasts kept creeping into my mind. I didn't have any clamps of my own of course, but I found that I could attach the clips from some skirt and pant hangers on to my nipples or clip clothes pegs on them, and when I tried this, I found it very exciting. Those kinds of clips hurt my nipples a lot when I tried them but I found that if I attached them more to the skin around the nipples rather than to the nipples themselves it didn't hurt as much. The only problem was that as soon as they started to hurt I would take them off, and I often wondered and thought what it would be like if someone else put them on me and then I wouldn't be able to take them off but would be forced to endure the pain – what then? But that was the extent of my experience until one day when I was chatting in a chat room and I struck up a conversation with someone who was called Bro-W.

I think Bro-W was male but I am not certain. Well, I guess I am sure he was as I can't imagine another woman suggesting the things he did. In any event, he seemed very nice and we exchanged a few pleasantries. He then asked me very nonchalantly if I would like to follow his instructions and tie myself up while we were chatting. I thought he was kidding and said so, as I could not figure out how I could tie myself up, but he said, yes, I could if I wanted to and he could teach me if I was interested. Well, I was intrigued at the thought and said so, and he suggested we move to another chat room where it would be quieter, so we did that.

The chat that ensued changed my life quite dramatically and so I am including a copy of that chat, and I have interspersed it with comments to help you understand what happened to me.

In a moment, Bro-W came back and suggested we move to a room called The Palace. I said okay, left the chat room I was in, found the Palace room he was referring to and went there. A moment later, there he was.

(13:02:25) Bro-W--Hi Diana, you made it, great! (13:02:30) Diana--yes, hello (13:02:40) Bro-W--Tell me more about yourself, how old are you? (13:02:50) Diana--38

(If you recall correctly, I am actually 48 but I did not want the chat to end because he might have thought I was too old or something, so I told him I was 38.)

(13:03:08) Bro-W--Where do you live (13:03:16) Diana--in Canada (13:03:28) Bro-W--and you are interested in bondage, why is that? (13:03:44) Diana--I don't know, I just find myself dreaming and thinking about it a lot – I can't get it out of my head (13:04:14) Bro-W--but you have never tried it at all, ever? (13:04:26) Diana--no (13:04:40) Bro-W--you are willing to learn? (13:04:52) Diana--yes (13:05:08) Bro-W--will you do everything I say, it is important that you do so you don't get hurt (13:05:24) Diana--yes (13:05:44) Bro-W--are you serious about that? (13:06:06) Diana--yes (13:06:15) Bro-W--everything? (13:06:22) Diana--yes (13:06:38) Bro-W--okay, there is no danger if you just do what I say, okay (13:06:58) Diana--yes (13:07:18) Bro-W--now, first I want you to take all of your clothes off. What are you wearing anyway? (13:07:56) Diana--just some jeans and a blouse

(That was what I was wearing too. It was one of the few times recently that I was not wearing any of the heels or hose that I had been acquiring.)