Tag: Cuckold

[MC][MFMMM][BDSM][SM] Anne & Jenny in Chicago

Feel free to let me know what you think, comment or pm. Thanks.

We were packing for a well needed vacation. Anne and I had been married for 12 years and this is probably our fourth vacation. We got married at a young age, while sometimes it seems to early, most of the time it seemed perfect for us. A couple of years ago, I came out to Anne as a crossdresser. She didn’t take it well. Months of stress built up but, things seemed to level out as we found out what worked for the both of us. You see, I love her dearly but, my desire to dress was in need of an outlet. I had pushed those thoughts from my mind for about 5 years each time. Each time, the desire came back with a vengeance. I decided a couple years ago, to come clean and share my deepest darkest secret. Anne had other thoughts. She didn’t want anything to do with it. We came to an agreement that I wouldn’t do it near her or around her. And as long as I stayed faithful to her, she would deal with occasionally finding my girl clothes around once in a while. Read more »

My [M27] birthday weekend with my GF [F31] and FWB [M30s][Chastity][Cuckold][Femdom][FM]

Background:

My girlfriend (Harley) and I have explored cuckolding pretty early on in our relationship. She has since slept with about 5 guys. We’ve only had one guy willing to have me present while I was there, but he couldn’t keep it up. About a month ago, we agreed that I could not fuck her until I had lost 20 lbs. for the first week, I wasn’t even allowed to sleep in the bed with her. The couch became my new bed. It wasn’t bad, considering she let me sleep in the bed while she stayed over and fucked her current fwb.

Day 1:

This started Friday afternoon. I got off work and she was waiting for me at home. She ordered me to get naked and put on one of my thongs. We climb into bed and she slowly strokes me throw my silky underwear for 30 minutes. Harley got pretty worked up and ordered me to get between her legs. I eat her out until she cums and pushes me away. She’s typically a one and done gal, but tonight she had different plans. Read more »

Shagged by a Stranger While Hubby Slept at Our Side [Cheating] [FM] [Cuckold]

Gary and I have hovered on the edge of the swinging scene for over a year now. I’ve already posted about our adventure with another couple in a tent. This happened just last weekend.

He’s had this cuckold fantasy going on for a while now. Recently it’s got more intense. He likes me to tell him what I would let men do to me if I had the chance and so I do. Storytelling comes easily to me. I suppose the next step is to tell him what a man actually did to me.

We’d gone to this house party. People from his rock climbing club. I didn’t know many of the guests. Just three in fact. I was bored out of my mind until Gary got so drunk he had to be put to bed.

He was sprawled outside the upstairs bathroom drooling. Cath and Mike, the hosts, helped me get him to the spare room. I was going to slip into bed with him but Cath said I shouldn’t let his being unable to handle his drink spoil the night for me. Read more »

What a difference a big cock makes! [fmM] [cuck]

My boyfriend got on top of me, shaking with excitement about what was about to happen, “I can’t wait, babe!”. I tried my best to smile while he reached down to apply a bit of lube between my spread legs. We hadn’t had sex in a long time, but it was his birthday and I thought he deserved it.

“Okay, I’m going to put it in,” He said – I nodded in encouragement. He took his cock in his hands and looked at my pussy a little bit too intently and then unceremoniously slipped it inside, while moaning in pleasure. I tried hard to pretend it felt good for me too, but the truth is, I barely felt anything. I never really did… I didn’t tell him because I didn’t want to hurt his feelings, but he was *way* too small for me to feel much of anything.

“Just remember, don’t come in me, sweetheart,” I reminded him. He moved his cock really slowly – I could tell that he was already struggling and he had just barely put it in. I mentally sighed and kept up the act, “Mmmm, that feels so good,” I lied. Read more »

The Dirty Thirty (Pics Included) [MF]

Lola almost caused my last relationship to end before it ever really began.

I met Lola on Tinder. At the time we first matched, she explained she was in a relationship with a cuckold boyfriend. Having experience with group play in the past, this was not a deterrent to me in the least. As we talked more in the days and weeks ahead, she shared photos and videos her boyfriend had taken with other men.

Around the same time I was texting with Lola, I had begun seeing a girl named Cara. We had gone on a few dates and had hit it off.
Over the course of two months, Cara and I saw each other often but never had a discussion about being monogamous. I assumed she was seeing other guys (she had even traveled to Asia to visit one during the time we were seeing each other). But apparently my thoughts on where we stood were misguided.

One night I had taken a nap and was awoken by Cara collecting her things from my room. She announced she was heading home without explanation. It seemed sudden, and I suspected there was more to the story. Minutes later I received a call from Cara, sobbing and angry. Read more »

Cuckolded by my son’s coach, part 3 [cuckold][mmf]

Excerpt from my latest, which is out now [here](https://www.amazon.com/dp/B071Y3XXZN)

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“Fuck, you look good,” I said to her as I watched her pull her dress up.

“Think he’ll like it?” My wife asked me, a little nervously.

“Yes,” I said emphatically… feeling a little bit humiliated that I was giving my wife advice on the best outfit to wear for another man.

We got into the car and did the standard drive to Derek’s place. It was in one of the nicer areas of our town—he had managed his finances well while he was a professional athlete himself. We pulled up to his big house (it must have been twice as big as our place), and my wife strutted up to the door. I watched her ass sway and jiggle as she walked… I was jealous that big black Derek would get to have her tonight.

“Cindy! Nice to see you.” The door to the big house swung open and there was Derek. Read more »

‘A Complicated Affair: Redux’ [mF, Anal, Cheating, Cuckold & D/s] (7,500+ Words)

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**A COMPLICATED AFFAIR: VOLUME ONE**

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**| Table of Contents:**

> * *Plot Summary*

> * *Introduction*

> * **One:** *’as_requested.jpg’*

> * **Two:** *’An Aversion to Small Talk’*

> * **Three:** *’Susan’s Only Rule’*

> * **Four:** *’Quasi-Religious Encounters’*

> * **Five:** *’Removing the Safety Seal’*

> * **Six:** *’Loophole’*

> * **Seven:** *’Second Virginity’*

> * **Eight:** *’Instant Replay’*

> * **Nine:** *’The Close Call’*

> * **Ten:** *’Bottled & Corked’*

> * **Eleven:** *’Developing a New Routine’*

> * **Twelve:** *’Unpleasant Formalities’*

> * **Thirteen:** *’The Incident’*

> * **Fourteen:** *’Confession(s)’*

> * **Fifteen:** *’An Alarming Blur of Events’*

> * *Afterword*

> * *Uncensored Story Tags*

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**| Plot Summary:**

A young man’s affair with a middle-aged hairdresser is complicated, after her husband learns of his wife’s severe betrayal.

Expect a story with a strong sense of acceleration and consequence, sustained across multiple chapters. There’s a handful of twists that you — *hopefully* — won’t see coming…

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**| Introduction:** Read more »

Wife’s Lover [Cuckold] [Huge Cock] [True]

My wife and I had been together for about 7 years at the start of all this, married for 4. Our life together was pretty good – we both had decent jobs, a nice house, and we enjoyed time spent with each other. We shared a gym membership and kept in shape, but neither of us had rock hard bodies. The sex we had 2-3 times a week was good, and though I was always up for more, I was happy with what I got. I was always kinkier than her, and often brought up new ideas – using a vibe, tying her down, etc. She went along with almost everything, but drew the line at threesomes. She didn’t like the idea of having sex with a stranger, and didn’t like any of our friends ‘in that way’. I eventually let it go, playing it out in my fantasies over the years.

She started grad school, taking classes after work a few nights a week. Her second year in she joined a study group, and soon after had a ‘Study Buddy’ she worked with. She described him as a nerdy kid, definitely not someone to be threatened by. The semester rolled on and she stayed out later and later with him. I didn’t doubt they were studying – her 4.0 GPA proved that much – and everything was good with us, so I didn’t have any reason to worry. Read more »

Crescent City Surfer Boy MILF Fun [MF]

Hi Y’all

Being the newbie to the Pacific Northwest and the kids on spring break from school my husband having some leave to burn, we decided to take a tour of the Oregon coast this past week. What an amazing trip and some fantastic adventures along the way. I’m so glad to have a supportive cuckold hubby that can cover for me while off having some fun to share with him later.

My favorite adventure of the trip happened in Crescent City, CA on the night before our visit to the Redwoods. We had stopped for the night in Crescent City and as a family all grabbed dinner at North Coast Ocean Sports and Grill. It was a terrific little dive that had great food and a view of a large beach with views of surfers and the sounds sea lions in the harbor behind.

As most of you know I’m always horny and love to fuck! The smallest thought of sex and my pussy starts dripping! I love to tease and will follow through on a tease to make some guy very happy! At least that’s the goal! Read more »

Cuckolded by the Black Billionaire Boss

Here is part 3 in my “The Boss” series, which you can check out [here](https://www.amazon.com/dp/B06XY7B4L1)

More of my writing at /r/todomforfun

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Mr. Brinks: She’s doing a good job with the first few inches.

I looked at the next picture and my eyes went wide. It was a close-up of my wife’s little pussy being stretched out by a huge black cock. The feeling of humiliation coursed through me as I stared and gawked at the absolutely massive dick. It was thick and veiny, and my wife’s pussy was wrapped tightly around it. Mr. Brinks hadn’t bothered with a condom, he was going to be taking my wife’s pussy bareback. I imagined how she’d be moaning at the pleasure of being taken by such a huge man, but realized that her sounds would be muffled, given how he had gagged her.

Mr. Brinks: Maybe if you beg me I’ll go easy on her.

I opened the next image to see a picture of my wife on her back, this time Mr. Brinks huge cock was balls-deep inside her. She was taking every single inch of the billionaire’s rod, and I could see her eyes wide, filled with lust and pleasure. She was being absolutely stuffed. Read more »