My Cuckold History

Hi to all

I am a member of both a cuckold forum and a chastity forum where members have been able to read about the relationship my wife and I have enjoyed. I hope Literotica readers will welcome the same opportunity. I have unashamedly cut and pasted my story from the forum postings, where it has been up for quite a while. But since it is my own work then I guess I have the right to do so.

*****

Part 1: Introduction

I have been married for just over 11 years now to my wonderful, sexy wife. I am 43 and my wife is 36 this year, and while the cuckold side of our marriage has quietened down recently the chastity side has certainly increased.

My wife likes the fit of the CB3000 on me, and while both of us are aware that removal is possible, she insists on the use of the second smallest ring, which would make it very difficult to get back on. The other element that ensures that I don't try to escape is that she has told me in no uncertain terms that if she ever finds out I have released myself then she will no longer entertain the kinkier side of our relationship—something that keeps me firmly on the straight and narrow!

Gradually my wife has increased the intervals between locking up and release and takes great delight in my frustration. The longest I have been locked away without a sissy spurt (as she calls it) is 60 days which happened last November and December. As I write this I am locked up for 45 days from June 1st to July 15th. She does of course unlock me daily so I can shower and shave (supervised naturally) and sometimes she will take such moments to tease me to the brink of cumming before ultimately denying me and locking me away again—Soooo frustrating!

I am never allowed to ask for any sexual contact but must always be ready to serve her (usually orally or with the strap-on attachment) whenever she wants it.

Just as a reality check, I'm not a 24/7 chastity slave, as it can be many weeks between the end of one session and the start of the next. But once she decides I need to be put into chastity the periods when I am locked up are quite long, so a bit of a break comes as quite a relief!

Anyhow...On with the cuckold part as promised. I'm afraid it may not always read as a story, more as a kind of log of how my feelings and reactions were (from a journal we kept, and from memory).

Part 2: Robert

Following on from my intro I thought I might as well write about how we started on this road. This story is not in any way extreme, it is just a truthful recollection of how my wife and I started out in a cuckold relationship...the juicy parts come later on.

Around six or so years ago we started swinging with select couples, not on a regular basis, but just when the opportunity arose. One time though when we had a meet set up the other wife couldn't make it and sent her hubby to meet us to explain. My wife and the other guy seemed to hit it off straight away and we ended up just having a MFM threesome which she enjoyed far more than all the other times. I guess that was the point at which the very first seed was sown.

Fast forward to around four years ago...

We used to download stories off Literotica and she found a good one one day which was supposed to be a 'loving wife' story but turned out to have a cuckold theme to it. We both found the cuckold thing to be a real turn on and used it in fantasy play more and more. Things started quite slowly on this road, but the first real event happened on a girls' night out when she met and flirted with a guy at a nightclub. They danced, kissed and generally had a really good time and at the end she shared a taxi home with him.

He gave her his number and said he would love to meet her again, even though he knew she was married. We had great sex that night as she told me all about her 'night out'...

It was a couple of weeks later that she brought up the idea that maybe it would be fun to go on a date with him. I was unsure at first and said I'd need a little time to think it over, but as the thought of her going out on a date ran around in my head for the next few days I knew that this was something we would have to try.

The smile on my wife's face said it all when I told her 'yes'. She sent a subtle text to him right there and then and asked him to ring the next day.

She was so excited the next day, just at the thought of this guy phoning her. Luckily he didn't disappoint and just after lunch he rang her. She took the call in front of me, and I knew that he had asked her where I was as she replied, "He's right here beside me," followed by, "No he said it's fine for me to meet up with you." They made a date for the following Friday and it was arranged that he would pick her up from our house.

We did what has become a regular thing now and one of the things I really love. Whilst she had a long soak in the bath, I selected the things she should wear for her first date from underwear to dress, jewellery and shoes. She loved my selection and as I lay back on the bed I watched her dress for her first date alone with another man.

At bang on 7pm his car pulled up to the driveway and she gave me a quick kiss and told me that she didn't know what time she would be back.

With that she picked up her handbag and went out to meet him.

I watched as secretly as I could from the living room window as he walked her round to the passenger side of the car and opened the door for her. Sounds silly I know, but just the sight of him putting his hand on her back as he walked with her gave me an instant erection!

They drove off and I settled back to a night alone in front of the TV. To say I had butterflies was an understatement. I found myself pacing around the house, not quite sure of anything except perhaps how exciting this whole situation was. It was a little after 10pm when she sent me a text and told me everything was fine, and she was having a great time. She went onto say that they had had a meal and they were going onto a nightclub so she may be a little late.

I felt relieved at least that she was safe and enjoying herself and managed to relax a little myself. At around midnight I went upstairs and read until I dozed off. I awoke hearing the sound of a car pulling up on the driveway and diving out of bed I ran to the window and peeped through a gap in the curtains. I saw my wife and her date chatting and in the car and this must've gone on for at least ten minutes before finally he climbed out and went and opened the car door for her.

My cock although hard already twitched as I saw her take hold of his hand and walk to the front door. I remember this moment as if it were yesterday...I watched almost glued to the window as they said a few more words then his hands moved up to her face and he kissed her. My wife responded to his kiss by moving her arms around his shoulders and pulling herself close to him.

The kiss seemed to last for ages and I enjoyed watching them both from the safe vantage point of the bedroom window.

Finally they broke the kiss and holding each other's hands they said a few more words before my wife put the key in the door and opened it. Although I couldn't see her now, she obviously waited whilst he went back to his car as he waved when he got in. Moments after he drove off I heard her shut and lock the front door. By the time she got up to our bedroom I was back under the covers. "Hi babe," she simply said as she made her way into the bathroom to take off her make-up.

When finished she climbed into bed with me and cuddled up. "Miss me?" she asked teasingly as she reached down and grasped my rock hard cock.

Next she gently took my hand and placed it on her pussy. "Mmmm, feel how wet I was for him," she whispered and before I could answer she pushed me onto my back and climbed on top, easing my cock into her soft warm and very very wet pussy.

Luckily she was so turned on by her evening out that it didn't take her long before she came. Seconds later I followed suit and had one of the most explosive orgasms I can ever remember.

So there it was, the first tentative steps into this lifestyle. As we lay in each other's arms afterwards she told me every detail of the evening. Remember this was her first time out on a date with another guy...

She didn't have sex, or a give him a BJ. In fact apart from some very close dancing in the nightclub and lots and lots of kissing they didn't really do much that night. That's what made it so special for her, he acted like a perfect gentleman and put her at ease.

I didn't know it then, but she would go on to date this guy for well over a year...As she would put it to me a few weeks later, "He's a keeper."

*****

I guess at this point I should fill in a few details...

My wife and I, although in a cuckold relationship are very much a loving couple. In no way could she be described as a 'slut' or 'bored housewife'. In fact she holds down a very responsible job which is why I don't use her name here and using a fake name just doesn't sound right.

As I have previously written, this didn't all happen overnight, but evolved over a long period of time. It is only really the last four years where the cuckold lifestyle has really taken hold. In that period my wife has only had three boyfriends, so you can see that she doesn't do one night stands etc. In fact there are periods where there is no one else on the scene and we carry on like most everyday couples when that is the case.

In a way that only heightens the excitement, as you never know when the whole process will start again...

Now—back to the early days with her new boyfriend...

Picking up from the night before, we lay in bed for most of the morning and discussed her and my feelings about what had happened the night before. I asked her if she would like to see him again and she said coyly, "I don't know...maybe."

I knew from her reaction though that deep down she would.

Later that afternoon we went out and took in a movie and meal. Halfway through the meal her phone beeped signalling she had a text. She read it to herself and I could see from the smile that appeared on her face that she was chuffed that he had taken the time to send a text.

I asked her if I could see and she said, "Of course...but don't you think some things should be private?"

My cock hardened as she said this and I agreed that as long as she was honest with me then yes, I would go along with her wishes.

Smiling she told me that it had just said that he had had a great night out and would she like to do it again. Also that she could call him for a chat anytime if she wanted to.

I asked her did she want to see him again and she simply replied, "If I'm honest then yes, I'd love to."

We chatted some more about the whole situation before my cock got the better of me and I said, "Well why don't you give him a call now. He said anytime."

Moments later I found myself sat at the table listening in on my wife's side of the conversation. To the best of my recollection it went something like this...

"Hi, it's me."

"Mmmm, thought there was no time like the present to call."

"Yes I had a great time too, wish it could have gone on longer."

"I know, I found that really sexy as well."

"I'd like that very much, when did you have in mind?"

"Next Friday..." She glanced at me to see my reaction at that point. I was by now caught up in the whole situation and nodded yes even though I only had an idea that they were arranging another date...

"Friday's fine."

"No he doesn't mind, in fact he's sat here with me right now."

Breaking into laughter she continued, "Yes he's very understanding, a real sweetie," and she added, "Aren't you," as she looked directly at me.

"I'll look forward to it."

"No, no need to do that, I'm sure JJ will be happy to do that." (JJ—she obviously used my name here)

"No I'm sure he won't mind, trust me."

"See you Friday then."

"Bye."

She had a grin on her like a cheshire cat when she clicked the off button on the phone.

Excitedly I asked, "Won't mind what?"

I felt her foot come up under the table and gently rub against my cock. Still smiling she said, "I told him you wouldn't mind dropping me off at his place next Friday, he wants to cook me a meal."

Wow...Did that ever hit home, I had just heard my wife talking to another man and telling him that I wouldn't mind delivering her to his door so that he could cook her a romantic meal...

That night we practically tore each other's clothes off and had great passionate sex. As we lay in each other's arms afterwards she asked me if I was alright with how this was going. It was after all a big step. Even though I had lost most of my excitement after cumming I knew that for some reason the answer was yes.

Fast forward to the following Friday night...

Once again we ran through the same bathing and dressing scenario. Whilst my wife relaxed in a deep bath surrounded by candles which I had lit for her I busied myself selecting her outfit for her date.

I chose her best black lacy wonderbra and matching g-string, stockings and suspender belt (of course) and her favourite little black dress which is short but not in an obscene way.

When she came into the room and saw what I had selected she teasingly said, "Wow, you must really want me to make an impression tonight."

I watched as she sat in just her bra and panties while she dried her hair and put on her make-up.

"Do you think he'll approve?" she asked when finally dressed.

I told her that he'd have to be mad if he didn't, she looked truly stunning!

"Well nip down and get me a glass of wine before we go, I need to just put on some perfume, oh and I wrote down his address and left it on the pad in the office for you."

My hands were literally shaking as I poured her a tall glass of wine. They must have been in contact over the last few days for him to have given her the address. I picked up the pad and was reading the it when she came into the office.

"Know how to get there babe?" she asked.

Feeling myself slightly blush at the thought of what I was about to do I managed to stammer, "Yes."

Finishing her wine she smiled at me and said, "Ready then?"

I opened the door to the car for her and remember just looking at how beautiful she looked...It hit me again though that she was dressed this way for another man, not me!

The drive would take 20 minutes or so as he lived over to the west of the city. As we passed by a local store she asked me to stop for a moment, as she had forgotten something. I waited in the car as she nipped in and moments later she appeared back at the car door. As I drove off she reached inside the bag and brought out a small box of condoms. "Just in case," she smiled as she transferred them to her handbag.

I asked her what she wanted me to do once I had dropped her off and she suggested I go get something to eat and take in a movie or something. Her hand sat in my lap as I drove and every now and then she would squeeze my cock which had been hard ever since we set off from home.

"You don't mind me seeing him again?" she asked, I'm sure looking for reassurance.

I told her I was fine with it as long as she was. This was a lie—I was about as excited as I've ever been in my life at that point.

"Good, what if this goes further, what if I want to see him regularly?" she continued to probe, all the time her hand rubbing my cock.

I told her that would be OK as well, as long as she was honest with me and didn't put our marriage at risk.

She told me that she would never do that, but that she really wanted to experience this. That the very fact that her husband was driving her to meet with another man made her feel exceptionally excited.

"I guess this really does make you a cuckold," she teased.

"I guess so," I replied trying hard to concentrate on driving as she teased my cock.

As I pulled up at his house she told me not to worry, and to try and have a good night myself. "I'll text you when I need picking up," she said and added, "You won't mind if it's late will you?"

She turned to me and gave me a quick peck on the lips and told me she loved me before picking up her bag and making her way to the front door. As she knocked she waved goodbye to me and I slowly pulled out of the driveway. Through the rear view mirror I saw him open the door and greet her with a kiss.

*****

I drove for about a mile down the street and then pulled over. My palms were sweaty and I was breathing hard. A million doubts crossed my mind, what had I done! I had just let my wife go into another man's house...not only that I had actually driven her there and consented to it. What kind of pervert was I?...Again the answer came straight back to me...

I was a cuckold, and I loved every second of it!

When I had regained my composure I drove off and found a nice Italian restaurant. "Table for one Sir?" The Maitre D's words echoed around my head as I sat down and ordered. I don't remember much about the meal, or the film I watched afterwards at the close by multiscreen. I do remember seeing all the couples out on a Friday night though and wondering if this was all happening to quickly.

As the credits to the film ran I glanced at my watch and checked my mobile for texts. It was 11:45pm and no texts had arrived as yet. I drove around the city centre for a while to kill some time and finally made my way back towards his house. I parked up at the same spot about a mile away and turned the radio on and waited...and waited...and waited.

If I'm honest all that I thought about was my wife giving herself to this other man...willingly! My cock was hard as a rock all the time as visions of her in his arms kept playing over and over.

I remember almost jumping out of my skin when the beeping sound of the mobile next to brought me back to the real world. I glanced quickly at the clock on the dashboard. It read 02:12—I will never as long as I live forget that time! Picking up the phone I read the message...

Hi babe, hope you had a nice night, I have...You can come and pick me up now XXX.

To this day I have never deleted this message, it still sits there in the inbox on my phone.

I drove up to the house and parked in the drive, some moments later the door opened and I saw my wife appear. Turning round she embraced this man and kissed him long and hard. Then taking him by the hand she led him over to our car. Wow—this I wasn't sure about. I hadn't prepared myself for this, to come face to face with the man who had just spent the last six hours with my wife.

As they approached the car he opened the door for her and they kissed once more, I noticed his hands running down over her ass as they did so, before at last she got in beside me. She shut the door and lowered the electric window. When he leaned through and quite calmly smiled at me and said, "Hi,"—in an almost surreal way it seemed normal.

My wife looked in my direction and said, "This is Robert babe. I thought you two ought to say hi to each other."

I managed to stammer, "Hi," back and they chatted for a while as if nothing was at all odd.

Finally he leant back inside slightly and gave my wife one last fleeting kiss before saying, "I'll call you tomorrow," and finishing with, "Nice to meet you JJ."

As I drove away it must've taken at least a minute before either of us said anything. My wife put her hand on my thigh and smiled at me as she said, "So what did you get up to tonight?" This broke the ice and I remember we both dissolved into fits of laughter.

The drive home was not at all awkward—thankfully and we just chatted normally until we arrived home. As I walked her to our front door she stopped me and gave me a huge kiss.