This story is about cuckolding. I have looked at all of the categories and Loving Wives appears to be the one where a great deal of cuckolding stories are submitted and so I have used this category.
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Chapter 1 - Exactly How do you Start Cuckolding?
In the aftermath of my birthday our sex life improved significantly for a short time. We spent most of the weekend in bed making love many times a day. Being a man I came every time. I could only tease Jess to gentle orgasms when I used my tongue but we were both happy and horny.
Once the new week started and we went back to work we continued to make love every night and on two days we did it before work. However, without the extreme stimulation of our first cuckolding experience the sexual spark began to fade again. Everything else in our life was as affectionate and loving as ever but the sex dwindled again. We made love three evenings during the second week, once in the third week and then went for another two weeks before we made love again. My frustration was beginning to rise again.
We often talked about starting our cuckolding journey properly. By that we meant not having to pay an escort to help out. The trouble was that we just did not know how. We tried a number of things. Firstly we tried going out partying with Jess dressed a little more revealingly than she would usually. She would dance and drink and I would try and hang back a little; not exactly apart but looking like friendly acquaintances rather than spouses. I initially thought this would work because Jess drew quite a lot of male attention. However, despite chatting, guys getting her drinks for her and even a little dancing she never felt the desire to hook up with any of them. She just was not in to them.
I got a bit frustrated with the situation and we even ended up having a few arguments. However, I had to agree with her that it was hard to introduce the idea of cuckolding into conversation. It is after all not what the vast majority of people are into. Most single guys would happily, eagerly even, take Jess somewhere and fuck her brains out, even if they knew she was married. Having me present though was a different matter and would be enough to put most people off no matter how appealing Jess was. We were at a bit of a loss. Picking guys up in bars and clubs was obviously never going to work.
Next we tried cuckolding dating sites. We posted a couples profile and some sexy underwear shots of Jess. This attracted a lot of interest from others interested in the cuckolding life. Lots of men propositioned Jess but again she never wanted to go through with it.
All this went on for about three months during which time Jess was getting a bit uptight and I was getting unbearably frustrated; we had not had sex that entire time and this showed no signs of changing. I had convinced myself that Jess would only have sex with me once she had cuckolded me again. When I look back on this mindset now I can see how ridiculous it was. Jess was not a slut. Many people would say that what she did on my birthday was her being a slut but I honestly believe that she did it all for me and she was uncomfortable about doing it. The fact that she hired an escort and so there was a commercial transaction involved somehow made it a bit easier for her to justify it. However, in reality I could have stopped the whole cuckolding idea there and then and she would have been perfectly happy about it. However, as I said, I had got it into my head that she really wanted it and the only way she would have sex with me again was for her to have sex with another man first. Of course, me thinking this probably meant that I acted in a way that did not exactly entice her to sleep with me. To put it mildly I was an idiot.
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Chapter 2 -- The Virtual Connection
I eventually realised that as Jess was not a slut she would never hook up with a guy unless there was some kind of emotional connection and that could only come with prolonged contact over a long period of time. You could say that I finally remembered that she was a woman and not a man. So we tried an adult social networking site. We set up our profile with our story and a selection of photographs of Jess in various stages of undress; always with at least her bra and panties on.
We entered a public chat room for the first time. Our computer was hooked up to our television so we had a 50 inch view and we switched on our high definition webcam. I let Jess lead the way. She pulled up live feeds from many different men. There was a lot of sausage on show; lots of men of all shapes and sizes masturbating on camera. There were a lot of women too but Jess was not interested and did not want me to look at them.
It soon became clear that Jess was not interested in just seeing some random guy wank. Firstly she wanted to be able to see the whole guy, not just his cock and hand. Secondly she wanted conversation before anything else. Now Jess was an outgoing girl and so it did not take her long to get engrossed in conversations with several guys. She quickly binned the ones she found boring or crass or who were only interested in getting her naked.
By the end of our first session she had added five guys as friends and promised each of them that she would be back on the next day to chat with them. She kept her promise and she chatted away for hours the next day. I was largely a passenger and did not really hang around for most of it. By the end of the second day she had acquired a couple more friends. This continued for the next month or so; she would spend a couple of hours each night catching up with some of her cyber friends. She had got over twenty guy friends by that stage that she regularly kept in touch with. Nothing sexual had happened yet though.
Over the next month her regular friends had dwindled down to four guys that she talked to a lot and the conversations got increasingly flirty as she got more and more comfortable with them all. By this stage it had been over five months since we last made love. My deluded obsession with trying to start cuckolding had created a wife who was addicted to social networking and who was much more interested in that than in sex. So I was actually quite surprised when she told me that she was ready to try cyber sex with one of her friends on the social network. His username was PompeyPete and he was white, about six foot four and buff. Even I had to admit that he was pretty. He was also extremely charming and warm and he seemed genuinely in to Jess and was not at all put off by the cuckolding.
Having watched a few other girls on the site we decided that Jess should have a vibrator so we ordered her a nine inch black one with bobbles on. It arrived a week later and Jess said that she was ready. She arranged to hook with Pete at the weekend; he seemed delighted and excited.
As the weekend approached I could tell that Jess was getting nervous. I knew that no one had ever seen Jess masturbate before and she had never used a vibrator. I tried to reassure her and I managed to convince her that it would be okay.
When the time arrived she had a couple of stiff drinks and said to me 'God, I am nervous.'
'I know but you will be fine. I am sure you will get in to it once you start.'
With a slightly uncertain voice she replied 'I suppose you are right but...I feel....you know.... embarrassed.'
'You have nothing to be embarrassed about. You are gorgeous. He will love it.'
'That is not helping,' she scolded.
'Well what will help then?' I did not expect the answer I got.
'I think it will help if...err...if...if you are not watching me.'
'You want to blindfold me?'
'No. If I am going to be able to do this then I think you need to be out of the room.' I was deflated.
'I don't understand. Pete will be able to see you doing it.'
'Well obviously. It just does not feel so real doing it on the television as it would having someone in the room watching you.'
'So shall I watch on the other computer then?' I asked.
'I'd rather you didn't watch at all. I want to do it a couple of times first to gain a bit of confidence and get used to it before I can face the embarrassment I will feel if you see me doing that to myself.' She seemed strong and certain.
'But I have seen you naked loads of times. Hell I have even seen you have sex with a big black guy.' I was sounded like I was pleading.
