I Am Cuck Ch. 02bywestcoastjohn©
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.
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.
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.
'Look, if I am going to do this then it has to be my way or we can call the whole thing off. It's up to you.'
All I could say was 'Okay.' I hung my head a little and left the room.
I was absolutely deflated. I had waited over five months for some sexual activity and now some was going to happen in my own lounge and I could not even watch, let alone get involved. I resigned myself to it and consoled myself with the thought that Jess was beginning to get interested in sex again and so my long wait would be over soon.
As it turned out it was nowhere near as soon as I had assumed.
Chapter 3 - Jess's First Cyber Sex
I obviously never saw what happened next but after it had finished Jess told me everything.
Jess logged on to the chatroom and quickly found PompeyPete. They chatted in the public area for a while before setting up their own private room.
'You look gorgeous tonight Jess.' Pete was right. Jess wore a tight tank top and a short tight leather skirt. Every curve was accentuated and she looked sexy.
'Thanks Pete. I am a bit nervous though. I think you will have to help me out a bit. I don't really know what to do.' Jess was nervous but she felt excited too; she did fancy Pete. He was a beautiful man and the lack of sex in her real life had left her having naughty thoughts about Pete and now that she had said it the thought of Pete telling her what to do tonight was getting to be quite a turn on for her.
'Well I have been really excited about finally seeing that gorgeous body of yours. Why don't you take off that top?'
Jess immediately felt a tingling sensation growing between her legs as Pete told her what to do and she was going to obey. She slowly, and as seductively as she could manage, began to lift her top up. The first thing to be revealed was the expanse of perfect milky skin on her tight little tummy.
'Oh yeah,' was all Pete could say; he had obviously started to rub himself through his jeans. This affect that she was having on someone she now considered to be a friend made Jess's heart beat a little faster; she was getting excited.
After what seemed like an age to Pete, Jess finally pulled her tight top over her full breasts; she was wearing no bra. For only the second time in her life she had exposed her naked boobs to someone she was not in a relationship with. They were big and perky and perfect. Jess instinctively began to rub them seductively. She was really beginning to get into this. She was still very nervous; she was even shaking a little bit; but she was getting really horny and could feel a slight dampness between her thighs.
'Oh my God! They are even better than I thought they would be. How can one girl be so stunning?' Pete took his top off too to reveal a perfectly sculpted six pack. Jess found herself thinking that if ever her and Pete had kids that they would be so pretty.
'God, I wish I was there so that I could suck those tits.'
Jess had never really been into sex talk but she wanted to throw herself into it. 'I wish you were here too. I just want to devour that amazing body of yours. I wouldn't let you out of the bedroom for a week.' She felt a bit silly and embarrassed saying it but it was fun.
'Oh fuck, you are my dream woman.'
'Well if you can't be here to suck my tits I will have to do it for you.' Jess grabbed her left breast and pushed it up to her mouth. She began to gently lick and suck the nipple. She had never done this before but she closed her eyes and imagined that Pete was doing it to her. She was getting incredibly horny.
Pete had opened his jeans and was vigorously rubbing his large hard cock. The site of beautiful Jess sucking and licking her own tits was awesome. He wanted this girl so badly.
'Do you like that?' Jess asked.
'Oh fuck yeah.' It was only then that Jess opened her eyes and saw Pete's cock for the first time.
'Oh my, that is big.' She was right. Pete's cock was at least ten inches. 'That is so much bigger than my husband's.'
'It's all yours girl. How long has it been now since that hubby of yours made love to you?'
'It must be five or six months.'
'Damn. What is he thinking? If I had a girl like you I would have you all the time. The things I would do to you. Man.' Jess felt naughty and horny as she listened whilst watching him rub his massive cock. Pete then gave his next order.
'Open your legs. Let me see you touch yourself.'
Jess obeyed without question. She parted her thighs to reveal bright yellow lace panties that matched her recently removed top. She licked her finger and stated to run it around her labia but on the outside of her panties. She immediately felt the dampness that had formed over the last few minutes. Her own touch felt wonderful; enhancing her already heightened sensitivity. She began to rub more enthusiastically. All thoughts of embarrassment seemed to have disappeared. At this moment she really wanted this gorgeous man to see her masturbate; something no-one else had ever seen her do; even me.
Jess and Pete's sex chat continued whilst the action played out.
Jess moved her hand inside her panties and ran her fingers around her wet lips. It felt so good and the sight of Pete tugging his monster to the point of explosion just turned her on even more. She slipped a couple of fingers inside herself and began to play with her clitoris.
'Take your panties off.' Pete ordered breathlessly. Jess leaned back, put her legs up in the air and slowly began to lift her panties off. Pete's view was amazing. Jess's ass was on full show; it was big and round and to Pete it was just like the rest of her; perfect.
With her panties off she spread her legs and pulled her lips apart so that Pete could clearly see her excited clit. She flicked it and rubbed her labia before sinking two fingers deep inside herself. Jess began to finger fuck herself making sure she stimulated her clit all the time. She began to get a little breathless herself as she got more and more aroused.
Pete could not take it any longer. 'Oh God. I am going to cum.' No sooner had he said it than Jess saw massive string after massive string of cum spewing out of Pete's amazing cock.
'I wish you had done that inside me,' Jess whispered.
'God. Me too.'
Pete watched Jess masturbate enthusiastically. 'God. I want to be in you right now. I would fill places with my cock that your pathetic excuse of a hubby could only dream of filling. I would make you cum so hard like he never could. Tell me he can't make you cum.'
'John cannot make me cum.'
'Why can't he make you cum? Tell me.'
'He has a small cock.' This trash talk, especially trashing me was turning Jess on even more in her state of extreme arousal. She was getting close.
'Shout so that he can hear it.'
'JOHN CANNOT MAKE ME CUM BECAUSE HE HAS A SMALL COCK.'
'JOHN CANNOT MAKE ME CUM BECAUSE HE HAS A SMALL COCK.'
Pete got her to repeat this over and over again until she finally came loudly and strongly. Jess's whole body was shuddering. She was still finger fucking herself as fast and hard as she could, trying to lengthen the orgasm as much as she could.
I was in the next room and I felt like hell hearing her shout that about me and then hearing her cum louder than I had ever made her cum. Then it dawned on me that Pete had just seen my wife masturbate and that was something that I had never seen. I was suddenly extremely jealous but I knew I could not interrupt or I would spoil the whole thing. So I sat and waited; assuming that she would be out in a few minutes now that she had cum. I was wrong.
'Wow, that was amazing. You are such a sexy woman. How can he not fuck you every night?'
'You know that you are the first person to ever see me doing that.' Jess smiled at Pete.
'You're kidding. You mean John has not even seen you play with yourself?'
'Well now. Are you still feeling naughty? Feeling horny?'
'I so am. I don't know what has gotten into me. I really do wish you were here right now so that cock could make me cum just as hard.' Jess was now feeling at ease talking dirty.
'Well I can't be there right now but how about we try something a bit more daring?'
'Well you mentioned a vibrator.'
'Yes, it's here.' She picked it up and showed it to him and then playfully rubbed it against her pussy. All the time since she had cum her legs were still wide apart so that Pete could see everything.
'Well how about you play with that and I shut down this room so that everyone can see you doing it? That way over one hundred people will get to see you doing something that little John never has. How fucking sexy is that?'
'I...I...I am not sure.'
'Just play with it.'
Jess stated to nervously rub the vibrator against her lips again. She switched it on and the vibrations reverberated through her and almost instantly brought her sex organs to life once more. It felt amazing; she was still very sensitive after her intense orgasm and it was not long before she slowly began to sink the plastic further and further into her vagina. It was as if her whole body was vibrating with sex. Her eyes were closed and she was fucking herself with this vibrating wonder. This continued for about five minutes with her pelvis gyrating to enhance her arousal.
At that point she opened her eyes to look at Pete. He smiled back at her. She then realised that she was no longer in a private room and that 108 people had her video open. She was shocked and embarrassed but the feeling inside her was so amazing that she could not force herself to stop. She closed her eyes and continued her personal, albeit very public, journey to her second orgasm of the day.
When it came it was even more intense than the last one. The fact that 96 men and 12 women were watching her masturbate just made everything seem more extreme, more sensitive, more enjoyable. These had been two of the best orgasms she had ever had.
Unsurprisingly there were a massive number of compliments (many extreme vulgar) on the chatroom text. Jess knew it was silly but these compliments actually made her feel really good, empowered and beautiful.
When she came out of the room she walked up to me and kissed me gently before telling me everything. My heart sank yet further when I found out that over one hundred people had witnessed what I never had. I could barely contain my jealousy but I had to. I still believed that if we were ever to make love again that Jess would have to cuckold me again. What an idiot; I know now that she would have made love to me all night that night if I had just made a move. But I did not. Instead I just kissed her for the longest time before she ran off to the shower.
Over the next two months Jess and Pete had cyber sex every night and it always ended with Jess masturbating in the public chatroom. I was still not allowed to join in or watch and my jealousy reached new heights as the number of people who had seen Jess masturbate was over a thousand and I still never had. What made it worse was the fact that Jess was now obviously very close to Pete emotionally and they had had daily sex for a longer period of time than I can ever remember having with Jess; although theirs was virtual of course.
I was actually torn emotionally. On the one hand I was all jealousy and frustration (it had been over eight months since I last made love to Jess). On the other hand I was glad because I knew that Jess needed an emotional attachment in order to progress to the next level and actually hook up with someone in order to cuckold me. It was my obsession with this that made me persist with it and even enthusiastically encourage it.