Finding the perfect woman (cuckold, cum swallowing, cheating)

CuckoldGuy's sex story
There comes a point in your life when you look back at your mistakes and look to the future and what you want to make you happy. After a failed marriage and many failed relationships. I was doing just that, looking seriously at how I could make my future happier.



For a few years I had been interested in cuckoldry, after reading about it as a lifestyle in the old Forum magazines. To be quite honest I was never convinced that I was good enough as a lover and so the idea of cuckoldry grew in my mind.

The reason was simple really, I enjoyed the company of women and wanted them to be happy and content. I truly believe that my partner should be fulfilled in bed for a relationship to be strong.

However fantasy, want and need are two different things. I had made the classic mistake of expecting the porn version of cuckoldry to be like real life. You know the thing the hot looking Milf from videos and stories who always appear to be from a higher standing in society than the cuckold.

I had chosen women like this and to my credit had pulled a few. But once the relationship had progressed enough to feel safe to sound them out about bringing others into the mix it was soon made clear that they only wanted one man in the relationship, and my fantasies were not on the menu.

I took time out and left all the groups that I had joined to find a cuckoldress and began to think about the way to make my fantasy real. It was making me depressed and I got used to the idea of living the last years of my life single.

And then on a cold winters morning I saw her! I was having a cigarette through my window when she walked down my street obviously taking her dog to the local park. What made her stand out even from this distance was how she looked.

She looked to be about my age, late forties. But looked older, like life had not been kind to her. She had long dirty blonde hair which was piled on top of her head. She was slim, and she was dressed sexily for such a cold, damp day.

What do I mean by dressed sexily? Well for a start, what stood out to me was her tight bright red spandex trousers! She also had a black shiny puffer jacket and some black suede boots which looked like they had seen better times.

Now I know that I was trying to get away from the porno version of a cuckoldress and I was. But there was something different about her. She was giving off the aura of a woman who had been around the block a few times, and what’s more she looked like she was still looking for cock.

It was the next day that sealed things for me. Again she was out walking her dog and was dressed similar to the previous day. This time though she had a grey nylon jacket on. And the same suede boots and today Black shiny spandex trousers. This was the sign to me that she was looking for sex, as it was not the type of clothing you would expect to see on the street during day time. It was the sort of clothing you may expect to see in one of the trashier night clubs.

The next day I decided to take a walk about the time she would be walking her dog hoping to bump into her. And just as I thought she was going to be a no show, there she was. Just as I walked around the corner she appeared. Catching me quite unaware I just mumbled a hello as I made sure I gave her a good look over.

Yes, I wanted her to know that I was interested, but also wanted to make sure she was what I was expecting. And she was. She was haggered but still with an aura of sexiness. I walked past her with a smile and after a five second count turned around for a final look, just as she did the same. Perfection she had caught me looking.

I walked back to my place, and began to plan the second phase of my seduction. There are two pubs near me one is a family pub where they do food. The second is a rundown estate pub the kind of pub with a dart board, pool table etc. It is not the kind of pub that I would usually use. But I figured looking at her, it would, out of the two be the one she would use.

Luckily it was Christmas so there would be a good chance that she would be in the pub with friends, as most women don’t go in a pub by themselves around here! Especially a pub like this one. I dressed myself up a bit and put my best aftershave on and made my way to the boozer in question.

I got myself a pint and stood at the bar taking a look around hoping that she would be in. At first I did not spot her but then I heard some loud female laughing coming from one of the booths. I noticed that if I went to the juke box I would be able to see who was in there.

I was in luck, she was there and still in the red spandex trousers she was in earlier in the day which probably meant they had not been washed in days. They looked great with a nice tight black spandex t shirt. I felt my cock stir as I took a long look at her. She had obviously had a few and was with two friends giggling and drinking.

Just to be near her and in her eye sight, I set up the pool table and began to pot a few balls. I kept sneaking a look at her every now and then, and spotted that her friends had noticed me looking, and were nudging her and whispering in her ear.

She grabbed her cigarettes and vodka and I followed her to the outside shelter. It was cold so there was no one else there. I watched as she lit up a long cigarette and exhaled smoothly as she leant back on the wall with one leg up.
Just to get close, I asked her for a light. Her spandex covered knee brushed against my hard cock as I leant in for the light, and our eyes met. As I said thank you, I put my hand on her knee and squeezed. She smiled and our lips met in a hot passionate embrace.

Jenna and I dated for about six months in a hot and steamy sex fuelled relationship. I just loved how trashy she could be and look. Soon it was time to find out whether she could become the woman I craved, one that would cuckold me! I cooked a meal and plied her with plenty of wine which I had laced with vodka.

Once I was sure she was feeling merry but not completely out of it, I slid my hand up her skirt as she lay back on the sofa. As I ran my finger over her satin pantied pussy, I took a deep breath and asked her if she ever still thought about other guys and missed the variety.

It was make or break time and I was sure she was going to answer in the negative. But I was shocked when she admitted she did miss her one night stands, as she loved to feel a new cock every now and then. This was the perfect answer for me, as it meant that she wanted different cocks but not get rid of me.

I told her that I would love to see her fuck other guys and that it would make me hot. As I spoke I felt her pussy moisten, and I rubbed harder on her pussy her hips moving up to meet me. “Yes, yes I want a new cock now” she cried clapping her hands . I asked if she felt like going to a local place known for dogging. Without much persuasion she panted, “fuck yes, let’s go”.

She went to shower and I looked in her wardrobe for something suitable for her to wear. I chose a short pvc skirt which was tight and only just long enough to cover her pussy. For a top it had to be an old t shirt which I ripped in strategic places to show off her nipples and bits of her tits. With a marker pen I wrote in big letters slut for cock.

When she came out of the shower she said she liked what I had done and found some old stockings which she ripped too before putting them on. She put the rest of the outfit on with some sexy ankle boots, as it would be soft under foot there.

I showed her a chastity device I had bought ages ago, and told her I would like her to lock me into it so I couldn’t intrude on her fun. She giggled but agreed forcing my cock into the device. I felt the spikes on the inside, and knew they would hurt if I got to excited. She kept the key putting it in her handbag, she grabbed the rest of the vodka and a short leather jacket she had, and we were on our way.

She made me stop at a garage to get her some more cigarettes and she asked if she should buy some condoms while we were there. I answered no, and was rewarded with a kiss and her saying “that’s completely the right answer”. I watched as she walked into the shop. I noticed a lot of guys watching her every move, one guy spilling petrol down his car!

Soon we were off again, and I could almost smell her arousal. It did not take long before the wooded car park came in to view. Jenna took a swig of vodka, and took two of her long cigarettes. She wiped the filtered ends in the juices coming from her pussy and gave one to me and one for herself.

We smoked them as I parked up in a discrete place, passing two cars on the way. “My god I cannot wait for some big cocks you naughty boy. You have put some filthy ideas into my mind, things I have always wanted to do, but never had the courage to do. Thank you for letting me do this and I have not said it yet, but I love you I have never had a boyfriend that has let me be myself”.

I told Jenna I loved her too and we kissed, touching each other up as we did and getting really horny. I felt the time was right, plus I needed a break, as my cock was getting painful in its cage. From my pocket I took a bottle of poppers which we both took a good long sniff from. I really wanted Jenna to fly and lose any inhibitions.

We heard a third car pull in not far from us and could see it was a guy about our age and big built. Jenna put on the interior light and refreshed her lipstick and lip gloss.

Taking another big hit of the poppers she told me to put on the headlights and some music. She took off her jacket and stepped out of the car and stood in the glare of the headlights. Jenna began to sway her hips to the music as I turned the interior light on, signalling to the other car owners that it was ok to approach.

The guy that had just pulled in opened his door and got out. From my wing mirror I could see he was bulging in his lycra shorts. I watched Jenna beckon him over blowing him a kiss.

He stood behind her as she danced grinding her sexy ass into his cock. I heard the other two car doors open and close and saw a middle aged guy who was slightly chubby, and a very young guy in a nylon track suit who could only just have passed his driving test approach. They stood by my car and glanced in to see me in my cage squirming.

I felt so humiliated seeing these guys watch me but so turned on. Jenna now turned, grinding her front into the buff stranger, and began to kiss him. She took another hit of poppers and beckoned me over to watch closer, as she slid down his body and took out his cock.

When I got there I could see he was large and very erect “look hunni isn’t his cock big, should I put it in my mouth”? I knew there was no going back. “Yes please, suck his cock for me like the dirty slut you are”. Jenna licked around the guys cock head showing me the pre cum on her tongue.

Jenna had a wonderful way of starting a blow job, by sticking her long tongue out and sliding it down the cock as she took the first mouthful. This she did letting out an “Mmmmm” of approval. As I and the other two guys watched she began to suck the stranger hard. The guy putting his hand on the back of her head.

I took the poppers from Jenna, and took another hit. My head swam as I turned to the young lad in the track suit and asked him to finger Jenna’s cunt for me. The older guy I asked to go and play with her tits and not be to gentle, as she does like a bit of roughness with her tits.

Jenna was going crazy with lust as she was manhandled. The guy who was being sucked suddenly spoke “. I am going to fuck this slut”. I nodded my assent to him and now knew he was taking control. He almost dragged my girlfriend to my car pushing her face up onto the bonnet.

I cursed my cock cage as I got to hard watching, his cock slide into Jenna’s pussy. Her face was a sight to behold as his cock stretched her pussy. The older guy put his cock in Jenna’s mouth and the young guy started to twist and pull on her nipples.

In between sucking the old guy she gave off mewls of contentment. Soon the first guy began to buck harder “I am going to cum” he shouted. Jenna locked her legs around the guy’s waist “Fill me with your hot cum, big boy”.

The guy grunted as he fired his cum deep into my girlfriends pussy And I saw Jenna’s eyes glaze over as her pussy was flooded by his baby making juice. He pulled off, and Jenna grabbed the old guy and forced his cock into her pussy. I think we all knew he wouldn’t last long.

Soon the old guy added his cream to Jenna’s pussy just as the young guy came in her mouth. As soon as they could they got back into their cars and left.

Jenna embraced me and gave me a hug. She then opened her lips slightly showing me that her mouth was full of the young guys cum. She leant in to kiss and soon we were swapping the cum between us and we both swallowed it all.

Jenna pushed me down onto my knees and I soon understood why, as she straddled my face. “Open your mouth lover and drink from my hole”. I did as asked and was soon rewarded with two loads of cum dripping into my mouth.

God this was all too much, it had been such a sexy evening, I was so turned on. Jenna bent her legs forcing her pussy onto my lips, and I began to lick every bit of the mixed cum from her. She came on my mouth as she rode my face.

Eventually she got off my face letting me breathe. As I started to recover I knew there was something else I just had to do. Still on my knees with cum all over my face I asked Jenna to become my wife.

She Picked me up from the floor, and as she kissed the cum from my face whispered that she accepted my proposal. As we drove home still high she told me of some ideas she had for the wedding! But that is another story.
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