My Cuckold History

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
jj62
jj62
56 Followers

Eventually the noises stopped, signalling that they must have finished. Moments later I heard the water running next door, as one, or more likely both of them shared a shower. For a good while afterwards I heard the sound of muffled talking and laughter as they shared a very private night together. Their first full night together!

I woke at around 9:00am the next morning and washed and dressed. My boxer shorts still lying on the floor still bore the signs of a large pool of dried cum as I had used them to clean myself off the previous night. I tentatively crept out of the room and listened at the door of our bedroom. Sure enough the familiar sounds of lovemaking greeted me, only this time I could hear much more clearly. My wife's cries of passion and the sound of the bed moving, no doubt as he pounded his cock into her.

I listened for what must have been twenty minutes as they fucked in our bed. Hearing quite clearly the sounds of my wife cumming at least twice before it all went quiet. I made my way downstairs and put a brew of coffee on and relaxed in the front room. At a little before noon my wife called down and asked me to put a fresh coffee on as they were just going to take a shower and would be down shortly.

I joined them in the kitchen as they sat at the breakfast bar. My wife was just in her dressing gown whilst Robert was fully dressed. As they sipped their coffee we made small talk and all the time I noticed his hand resting on her thigh. Almost as if marking her out as his property.

Finally he made his move to go and my wife stood and they embraced, kissing quite passionately in front of me. Her robe opened slightly and his hands wandered inside. I watched as his hands once again caressed her ass.

"Sure you won't stay a while longer?" she teased him when they finally broke away from their kiss. He said he would love too but had some things he had to do.

He said bye to me and she saw him off to the door. One more lingering kiss and he left. She waved as he drove off then it was just us together again.

She came over to me and gave me a big kiss and we shared another cup of coffee and chatted about the whole experience.

Finally she said I deserved a treat as I had been so understanding of her needs and she led me back upstairs. Once back in our room she undressed me and led me over to the bed. I couldn't help but notice that there in the middle of the bed was quite a large wet patch.

With no hesitation she told me that they had decided that as they knew each other a little better now that condoms were no longer necessary. "Besides, I knew you wouldn't mind. You like the idea of him cumming inside me don't you?"

"Y...yes," was all I managed to say before she pushed me back onto the bed and straddled my cock, taking it deep inside her.

"Don't take too long will you, I'm a little sore down there," she teased me.

My wife continued to see this man for just over a year. Each time seemed to get a little hotter and my wife introduced bit by bit different aspects of cuckolding. One thing I did find particularly exciting was when they took a weekend break away alone on their anniversary.

As all things do, eventually it came to an end. I won't go into details but circumstances changed and he had to move away for his job. They still communicate on rare occasions via email and I think it's fair to say we all got a lot out of this relationship and were a little sorry to see it end.

I'll go into more detail about the differing aspects of cuckolding my wife introduced when I write about her second boyfriend and the experiences we had with him.

Part 4: Dennis

A new man on the scene.

After my wife's first boyfriend moved away with work we did much talking about our feelings and what had happened over the last year. Both of us wanted to carry on exploring our new found relationship but how to go about it?

Sure you could use the many personal ads on the net, and we did look! Eventually though we decided that the best way for us was to carry on as we always had done and just be on the look out for any opportunities that came up in every day life.

Opportunities however don't come around that often as we found out. It took around a year before anything remotely possible happened. During that time we continued to talk about our feelings and drew upon the experiences we so recently lived through in fantasy play.

As luck would have it the next opportunity arrived via a conference my wife attended. She was away for three days and on the first night when she phoned me she remarked that she had been chatting to a man who she described as yummy—her words not mine! He had been presenting at the conference and they had struck up a conversation in the coffee lounge afterwards All very work related so she told me.

I joked that maybe she should chat some more if she came across him again... "I may just do that," she replied.

Around lunchtime the second day I received a text on my mobile. Mr Yummy is here again was all it said. Wow I started to get those butterflies in the pit of my stomach again!

That night it was around 9.00pm that she rang me. She had been out for a few drinks and a bite to eat with some of her fellow attendees.

It was no surprise to find out that he had been one of them. I asked all sorts of questions but she was adamant that this would in all likelihood come to nothing. I asked her pointedly if she thought he was good boyfriend material to which she replied, "Oh yes...I'm sure he would be, given the chance," but no matter how much I pressed her she kept telling me that it would be very unlikely to go anywhere.

The final day she sent me another text. Maybe I was wrong, do you mind if I grab a bite to eat at the close of the conf???

It only took me two seconds to text back Enjoy your meal!

It was a little before ten pm when she arrived home. I took her bags and gave her a big kiss before handing her a glass of wine. She chatted about the conference and some of the people she had met and I'm sure was just teasing me by deliberately not mentioning her new found friend.

Finally I could take it no more. "Just tell me."

Smiling wickedly she began to tell me all about it. Apparently at the coffee lounge on the first day it really was just work related.

The second night they had chatted over dinner shared and shared a couple of drinks at the restaurant bar once everyone else from the party had left. She told me that once alone they had then chatted about each other and he was apparently very flirtatious with her.

She said she couldn't quite put her finger on it but there seemed a chemistry between them.

The meal they had shared earlier had been just them and she told me that they had once again flirted with each other and that he had told her he found her very attractive and it was a shame that she was married. She had joked back that she too found him attractive and maybe it needn't be a shame. He asked her to explain what she meant and to her credit, my wife didn't tell him all about us there and then, but sowed the seeds in his mind that maybe this was worth pursuing. At the end of the meal she wrote down her private email address and gave it to him and said to drop her a line if he wanted to catch up on anything.

When we finally hit the sack that night I asked her had she actually done anything with him. She told me that no she hadn't as she wanted to see if he was really interested in her or was this the line he usually took at conferences.

Lo and behold, the next day there was a new email sitting in my wife's in tray. It was short and sweet, but showed that there was definitely an interest there.

Hi gorgeous...Just a quick note to tell you how much I enjoyed our chats. Thought about what you said yesterday and would definitely like to chat again, give me a call on 0xxxx xxx xxx anytime. I would love to hear from you! Here's hoping...

Despite numerous prompts from me, my wife left it until the Sunday to call him. She made the call upstairs in the bedroom as she wanted a little privacy while she chatted. From what she told me afterwards they chatted about many things. It transpired as luck would have it that he lived around 60 miles away from us. He was a successful businessman who was divorced and travelled quite extensively. He was quite open and honest with what he said and he brought up the thorny issue of me as he didn't at this stage know anything about our lifestyle.

My wife played a little coy about this and suggested that they should perhaps meet up for a drink and a chat. They agreed upon meeting for the following Wednesday night at country pub midway between us.

I could tell that my wife was keen to see what would happen and we tried to work out how to actually broach the subject of our lifestyle. We finally decided that telling the truth about it would be the best option and if he wasn't comfortable with it, well, that would be that.

We did our usual routine of her bathing and me selecting an outfit for her to wear which stirred up a lot of happy memories for me.

We set off from our house at 7:15pm and arrived at the pub just before 8:00pm. I parked the car and my wife gave me a kiss and told me to wait for her out here. She said to me, "I may be back quite soon. If he doesn't show by 8:15 then I'll be back out and we'll go home. If he does, then I don't know how it will go."

I watched the clock and more notably the people going in and out of the pub...Each single guy who walked in could've been him...

8:05...

8:10...Each minute seemed to take an eternity.

8:15...My heart was beating quite fast by now.

Finally when 8:30 came around I knew that he had at least turned up and they were chatting. I thought about sneaking in to have a look but didn't want to interrupt whatever they were discussing.

At just gone 9:00pm I got a text on the phone which simply said You can come in and say hello if you want.

My heart began racing...I made my way into the pub and saw my wife sitting at a table with her new 'friend'. Taking a deep breath I walked over to the table. My wife smiled at me and broke the ice by making the introductions. "Honey this is Dennis...Dennis, this is my husband."

We both said 'Hi' to each other and I was about to ask if either of them wanted a drink and to join them at the table when she added, "You don't mind waiting for me back out in the car do you?"

I was a little taken aback but before I could answer she continued, "Dennis and I have a lot to talk about," and with that she reached across the table and took hold of his hand.

I remember managing to say, "No...of course not," before slowly making my way back out.

Sitting back in the car I turned the radio on and listened to the usual midweek stuff. Ten o'clock came and went as did eleven o'clock.

Finally, at a little after 11:30 they appeared at the doorway. Hand in hand they walked over to the car and he opened the door for her. Before she got in they shared a long kiss. As I was already in the car I could only see the bottom half of their bodies. His hands gently ran down and rested on her ass as they continued kissing. I remember watching almost in a trance as they finally broke their embrace and my wife slipped in beside me. She pressed the electric switch for the window and opened it. Dennis peered through the window and ignoring me whispered to my wife that he would call her tomorrow night for a chat.

*****

As we drove off I could tell her mind was running over the meeting she had just shared. "Have fun?" I asked.

She looked at me and with a wicked smile took hold of my hand and placed it under her short skirt and onto her panties. Instantly I could feel they were damp. She moved a little to allow me better access and said, "See for yourself."

I nudged her panties to the side and my finger brushed the opening to her soft, warm and soaking pussy.

"Need I say anymore?"

Slowly I played with her lips as I drove, every so often easing my finger just inside her which made her moan in a most sexy way. My cock was as hard as a rock as I thought about how turned on she had been just chatting with Dennis. All too soon she removed my hand and told me I should wait till we got home.

No sooner were we through the front door than I found myself kneeling in front of her as she hiked her skirt up and pulled her panties down. Leaving them bunched around her ankles she placed her hands on my head and pulled my face up to her pussy. "Mmmm...do what you do best," she teased and began to grind slowly against me as my tongue found its way inside her.

It took only a minute or so before I felt her body shudder a little as a powerful orgasm took hold. Stepping out of her panties she beckoned me to follow her into the front room and leaning over the arm of the sofa she told me to fuck her long and hard from behind. It had been a long time since I had seen her this worked up and she kept pleading with me to, "Fuck me hard...harder goddammit."

I did so for as long as I could before the excitement overcame me and I came, collapsing over her back as I did so.

We caught our breath for a few moments before reluctantly I eased myself up. She gave me a long kiss and taking my hand we made our way up to bed. As we relaxed in each other's arms she told me bits and pieces of their conversation. She explained that she had felt it best if she was absolutely honest with him from the start and had told him that she had taken a lover before and that I was quite happy being a cuckold.

Dennis had apparently joked that she must be kidding and that no husband would surely let his wife do that to him quite as openly as that and that is why she had sent me the text asking me to join them in the pub. "You did really well honey, especially leaving again so soon when I asked you to."

I asked what his reaction had been and she told me he had laughed and more pointedly, so had she.

I told her that I wasn't sure she should have brought up the cuckold bit quite so soon but she cut me off by saying, "Well that's what you are isn't it...a cuckold?"

"Y...Yes I suppose so."

"Well then no need to worry. Besides, Dennis understood completely."

Finally we drifted off to sleep, no doubt both of us running the events of the evening through our heads as we did so.

*****

Good to his word he rang the next evening and they chatted for well over an hour. Afterwards I asked her what they had said but she told me I would have to wait until Saturday night to see as Dennis had said to keep it a surprise.

Saturday seemed to take ages to come. I was in true cuckold heaven as I watched her get ready for him. A little after 6:30pm I heard the sound of his car pull into the driveway and my wife asked me to let him in while she put the finishing touches to her make-up.

Just as he reached the door I opened it and let him in. we made a little awkward small talk for a while before I led him through to the living room and asked him if he wanted a drink. I told him my wife shouldn't be long and she was just putting on her lipstick and went out to the fridge to get him a glass of red wine. I also poured my wife a glass of white wine and took them both back to the front room.

I hadn't heard her come down, but I was greeted by the sight of Dennis and my wife embracing and sharing a passionate kiss as I entered the living room. They didn't stop as they no doubt heard me come in. After what seemed an eternity they broke away and sat down next to one another and chatted. I listened intently, my cock semi-hard with the knowledge of how turned on my wife would be.

Dennis whispered something to my wife and she turned to me and said, "Honey...be a sweetie and go fetch my overnight bag from our bedroom, it's all packed on the bed."

A little surprised at her request I said, "Y...You mean you're going back to Dennis's place tonight?"

"No sweetie...Dennis has tickets for the theatre and has booked us into the Regency afterwards. He checked in on the way over here."

Feeling a little awkward I made my way upstairs and into our bedroom. There on the edge of the bed was her small overnight case. I took a few moments to catch my thoughts. How stupid I had been thinking they would be staying in. There was nothing prepared in the way of food and I had somehow not given that a second thought. This was certainly not what I had been expecting, but very tellingly I felt my cock was twitching with excitement at the very thought of her staying at a hotel overnight with him.

I picked up the bag and resisted the temptation to look inside. Not because I was being honourable, just because I knew I had already been upstairs for a while and they would no doubt have noticed that.

When I reached the bottom of the stairs they were already there. Dennis was helping her on with her coat and they were laughing about something or other. My wife said, "You don't mind dropping us off at the hotel do you?" knowing full well I could hardly say no (nor would have done).

I carried her bag out to our car and put the case into the boot. Dennis meanwhile had walked out hand in hand with my wife and had opened the back door and helped her in. As I started the car Dennis jokingly said, "The Regency please driver," to which they both laughed.

As I drove they both chatted away to each other in the back. I could see his hand resting gently on my wife's thigh through the rear view mirror.

It took about 20 minutes to get to the hotel and I pulled up right outside the front. I opened the boot and retrieved the case, noticing as I did so that a doorman had now appeared on the scene.

"I'll take the case for you Sir," he said.

He needn't have, it was only a very small bag, but I guess this was all part of the service. As he walked up a few of the steps leading to the door Dennis and my wife got out of the car. Dennis had his arm around my wife as she faced me and said in a hushed tone, "I'll give you a ring in the morning to tell you what time we need to be picked up...now try and have a nice night honey," and with the briefest peck on the cheek she and Dennis made their way towards the waiting doorman.

"Welcome to the Regency Hotel," he said greeting them.

I watched as they made their way inside, still a little bewildered at what had happened. Climbing back inside the car I made my way home.

The vision of the doorman taking the case from me then greeting Dennis and my wife gave me a huge hard-on the more I thought about it. No sooner did I get through the front door than I made my way straight upstairs. Hurriedly I stripped naked then retrieved the pair of panties my wife had been wearing earlier from the washing basket and laid back on the bed and masturbated furiously, taking deep breaths as I inhaled the wonderful aroma that still adorned her most intimate garment.

I'm not ashamed to say I masturbated twice that night, catching the cum the second time in the lacy black panties that served as such a powerful memory of my wife.

My evening was spent fetching a take-away and watching TV. I finally went up to bed around 1:00am and drifted off into a very fitful sleep, very aware that on only her second real date with this man she had not only chosen to sleep with him, but to spend the night with him too.

*****

The next part covers how our relationship changed slightly during the time my wife dated Dennis. Changes that include such things as how and why she started denying me full sex with her.

This was originally written as a diary type of journal a few years back. These notes capture quite well the period in our life when we were indulging ourselves in 'extra-marital' sex—or at least my wife was (LOL). The reason they read like they do is that we both wanted to document what we felt so we could go over it and re-live those times later on (just like we are doing now I guess).

jj62
jj62
56 Followers