First Time Cuckold (What To Expect)

woman and man cuddling on sofa

I’ve been desperate to share this story for years now and it seems like a good time to finally get it off my chest.

This is the story about the first time I shared Sarah (this is my girlfriend) with another man.

What does Sarah looks like?

She’s 28 years old, 5’2″ dark eyes, and hair, petite body with a tight ass and small-medium perky breasts.

She’s the hottest woman I’ve ever been with and that was one of the hardest parts about sharing her.

Finding Out I’m A Cuckold

woman sitting on sofa

One night Sarah and I had a drink and we started talking about past lovers.

The one with the biggest dick, the one who she let cum inside of her, I learned everything, from her first time trying anal to the first-time she swallowed.

You would think this would anger most boyfriends… Not me, I was turned on.

Fast-forward lots of long nights up talking and you reach the part where she knows I like cuckolding and she wants to spice things up.

Mostly because she hasn’t been with another guy other than me for most of her twenties, to say she was keen to open up our relationship would be an understatement.

Making Sure She Wanted To F**K Another Man

cuckold sub-reddit

We started by going on these cuckold sub-reddits and signed up to a few dating sites.

She started talking to other men, sending nudes and eventually she had cam sex with a guy called Lex while I watched.

Seeing Sarah’s pussy dripping wet once she started masturbating on webcam and seeing this guy touching his massive cock in awe of Sarah was the hottest thing I had experienced so far.

I left the room for one minute and by the time I came back all I could hear were her moans, the sound of her touching her wet pussy and the sound of him stroking his cock.

Sarah started cumming and before she could finish Lex blew his load.

They both giggled, sent a few messages and the Skype chat ended.

The Moment After Sarah Had An Orgasm

It was awkward.

Sarah was silent and a little shy.

I was filled with anxiety and arousal (a weird mix).

She went and had a shower and it wasn’t until the night-time we really talked about it, after having a few hours to cool off.

We both agreed it was hot and we went through a period of her having cam sex with different guys for a few months.

Was It Hard For Me?

I did battle some jealousy and found it hard when I could see her falling for someone, but… We had sex almost every night.

Her sex drive was high before, but now it was as high as mine and at the time my feelings were worth the trade-off.

She Really Wanted To Try A Real Cock

girlfriend in sexy lingerie sitting on sofa

One night after a few drinks my girlfriend with starry-eyes asked me if we could try a threesome.

I asked if she had anyone in mind?

She got her laptop out and showed me some messages on Adult Finder.

There were loads of guys in our area and she started some conversations up, funny enough she only picked the guys with the biggest cocks I’d ever seen.

Almost instantly one of the guys (David) got back to us and after sending pictures we decided to meet the following weekend.

The Important Part:

Part of this week building up to the threesome was spent creating a list of rules (do’s and don’ts) and we both promised we would not change any of them on the fly.

  • Must-use condoms (this is a must, even though she was on birth control).
  • No anal sex.
  • No cuddling.
  • No texting without both of us present.

You can use this to make your own cuckold/hotwife contract.

My First Time Cuckold Experience

hotel room

All the prep was done, we booked a hotel 20 mins from our house, arranged to meet David at 9PM, we had our favorite condoms, lubrication and Sarah even brought some drinks with us for the hotel room, it was time for my first cuckold experience.

The day of the Threesome:

I hardly slept the night before, we got up at 8 am and the day flew by.

We had about an hour before we left and Sarah had her last shower and called me in.

She flashed her bare ass while bending over spreading herself and showing me everything while asking “do I look good enough?”.

She looked the best I had ever seen, she had made such an effort.

Imagine her smooth, tight, hairless ass and pussy that was already soaking wet.

Words cannot express.

I then got asked to leave while she did her make up and got ready.

30 minutes later I got called back in…

…She had bought a new black sheer lingerie set (the see-through kind) and a cute short black dress, she was wearing red lipstick and her hair was straight.

She looked cute, hot and naughty all at the same time.

“What do you think?”

“Do you think David will be impressed?”

She kept asking if she was enough and if she looked good.

Obviously she was perfect.

So, We Went To The Hotel

Checked in, here’s the texts she was sending to David:

cuckold test messages arranging the first meet up

We went to the hotel room and had a strong drink.

It was time, we went to the bar.

We walk in and there he was.

Honestly, when I saw him my heart was pumping through my chest, he was hotter in real life and I knew he was Sarah’s type.

We all had a drink, talked, David and Sarah flirted and she kept touching his leg and eyeing him up.

It was time to go back to the hotel room.

He Was Moments Away From Being Inside My Girlfriend

hotel room door

Before we were back he started kissing her in the elevator.

By the time I got the door open she lead him to the bed, no lights had been turned on.

I could feel my heart pumping through my body, I had anxiety and was really aroused all at once.

She laid him on the bed, unzipped his trousers and within one second she pulled his cock from his boxers and let out a little giggle.

His penis was long and fat, honestly it was something you would see in porn..

I was just sat at the end of the bed, all I could hear was his moans and the slurping of her mouth trying to fit him inside.

I pulled her dress up and her pussy was so wet it was dripping down her thigh, something I didn’t even know was possible.

She was trying to please him in every way she could, it was like seeing behind the scenes of my girlfriend cheating.

Before I knew it he pulled her head up and they switched and he went down on her.

I was awkward and didn’t know what to do so I just watched.

He was massaging her pussy while he sucked her clit, the moans she was making where like nothing I’ve ever made her make.

She reached orgasm in minutes, quicker than I’d ever made her cum (that hurt a little).

She pulled him up, literally begging for his cock trying to thrust it in with her hips. He put a condom on.

There was a weird part of me that wanted his cock to be uncomfortable and not enjoyable for her, even though I was so aroused at the idea of her enjoying it.

Guess what?

He glided inside of her I had no idea she was so deep and could stretch that much.

All I could see from the back was his cock covered in her cum and pussy juice as he thrust inside her.

She was moaning, then taking deep breaths and then cumming and repeating the cycle.

He knew exactly how to hit her g-spot and she looked like she had forgotten I was there.

Then he flipped her to doggy style position and she waved me over, she put me inside her mouth while he thrusted deep inside her.

He was thrusting so hard she couldn’t suck my dick, it was lucky because I couldn’t have lasted a second in her mouth.

I’m not sure, but while in doggy I think he put his fingers in her ass but it felt like he did (this was against our rules) but it was like my girlfriend wasn’t there anymore, she was so turned on.

He could of made her do anything, she was his and it was like I wasn’t there.

These are the feelings that an unexperieced cuckold feels, well at-least I did.

They must have f**ked for at-least two hours straight, he went through 4 condoms, she was covered in his cum (he gave her a facial and finished on her butt) and he was still making her moan.

I joined in for some parts and masturbated a lot but kept stopping before I could cum, I didn’t want to get orgasm regret while my girlfriend was being f**ked by a bull.

What Happened After She Came?

woman showing censored chest

He left about 4 am, it was awkward, I had some regret, but seeing my girlfriend lose herself and experience something I could never give her was ecstasy.

It’s a weird mix of feelings from sickness and anxiety, to arousal beyond words and adrenaline.

We both had a shower and during mine, she came in and said something like “Thank you for letting me experience that, you’re the best boyfriend in the world, I love you”.

We made out and had sex, her pussy was still stretched to his size, again that’s another thing I didn’t know happened.

I came in seconds and we did our best to sleep in a bed that was covered in his cum, her cum, and their sweat.

The next morning it was a mix of guilt, arousal and awkwardness.

Each day it got less awkward and hotter until we tried it again and again before venturing out to try other guys.

It was hit and miss the first time, but each time it got better, more normal and we became stronger.


Recommendations For First Time Cuckolds

my hotel room

Before you try anything to do with cuckold/hotwife I highly recommend you read this cuckold training plan and then follow these first-time cuck tips and advice.

#1. Use this awesome cuckold techniques

Start by using the webcam method that I talk about in that article.

See what feelings arise, then let your wife try sending nudes and sexting another man.

Check yourself again.

Finally, try a threesome.

I get it you want to be cucked, but trust me the first time you share your lover it’s best if you’re involved…

#2. Don’t let your wife F**K without you present

The first few times you share your wife you need to be there.

That’s why I recommend labeling it as a threesome.

You don’t have to get involved you can just watch, but at least be present.

Nothing is worse than finding out you’re not a cuck while you’re wife has taken some guy that’s hotter, bigger and better than you back to a hotel and is showing him every part of her, especially the parts she doesn’t let you touch and see.

When in doubt threeway it out.

#3. Try simulating cuckolding with a sex toy

Get a suction cup dildo and have your partner ride it while she gives you a blowjob.

Want to see how she takes a massive dick?

Try a penis sleeve, mine adds 3 inches in length and a few inches in thickness.

Sarah literally makes me use it at least once per week and it’s the only way I make her cum through penetration.

This also helps you satisfy her if she turns into a size queen after trying someone with a bigger penis than you.

Want to watch her getting f**ked?

Try a sex machine! These can get expensive, but I own a few of them and nothing is hotter than seeing Sarah take every last inch of her 8″ sex machine.


Want more? You can join our Cuckin hotwife/cuckold community and get access to loads of videos, gifs, captions, stories and guides.

I'm the cuckold of cuckin.com. I write about my experiences sharing Sarah and about the things I learned. I've been a cuck for the past 4 years of our relationship, but have been studying this lifestyle for the past 10 years, when I first found out I got turned on by the idea of my partner being with other men.

Comments:

  1. We’re just starting out now, so I don’t have many cuckold stories, but my wife tells me about how her ex used to make her cum from his big dick and she tells me about all the things they tried and how he was the best lover she’s ever been with.

  2. I guess I’d like to know what happens immediately after the first time? How did you feel and was your wife reassuring in a way that you believed? Was there any sense that she was not being totally honest about her physical and emotional takeaway from the experience? Any sense of a lack of respect for you or that she was now in control?

    • Hey Devon, I’m Sarah (the girl who got shared), after it happened it was a mix of different feelings, there was a little guilt on both parts and we did wonder if we did the right thing. Every day that past after the experience them emotions went away and were replaced by a craving to try it again.

      Luckily Jack and I both enjoy the same things, it’s not about me having sex with some random guy, it’s about how each part of the experience turns us both on. We are both enjoying the experience as much as each other and that’s why it works for us. Our actual relationship hasn’t changed, we spend 95% of our time just doing normal couple stuff, it’s just that 5% when we let our inner kinks out – Sarah <3

  3. Our first-time cuckold experience was a few years ago. We decided to do it on vacation and it was pretty magical as everything just fell into place. My husband did the classic thing of sitting and watching from the corner of the room and it just felt so right, it really opened the doors for us.

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