Tag: Cuckold

[group] M/36 I’m a down low in the closet Thug with face tattoos. I chase girls but little do they know I suck cock and dress as a sissy behind closed doors. This is my full sexual confession. (Pics on profile)

My Sexual Confession

Here’s my confession I need to get it off my chest..

I’ve been sucking dick since I was a teen. My old best friend (Danny) and his younger brother used to suck each other. Danny had a big ass dick way bigger than mine even now lol.

I fucked and sucked my first transsexual at 18 years old. I was a professional tranny hunter In my 20s and I’ve been with over 200 trannys I always thought I would never Fuck A cross dresser but eventually that’s The majority of who I fuck now mostly cuz their way easier to find now days on grindr.

I first start dressing in women’s clothes and women’s lingerie in teens… I first started wearing my mom g strings and lingerie. I first hooked up with a guy wearing my moms lengerie around 21. He said he was 18 but looked a lot younger.. lol he ate my ass and couldn’t get hard I remember. He Suck my sissy little dick and I came in his mouth in like 2 mins because I was so turned on dressed as a full sissy and Fully shaved. Read more »

Making my wife cheat on me (cuckold)

My wife is young, she’s 24 and I’m a lot older. We met at work. I run my own business and I was looking for a PA. She applied for the job and when I interviewed her she was fucking gorgeous. I was single at the time but never in a million years thought she would give me a second look. I did a lot of work abroad and when she travelled with me we spent a lot of time in hotels. I always asked her to book two double rooms, one for me and one for her.

We flew out to Paris for a meeting in 2018 and when we checked into the hotel, they just gave us a double room. I complained but reception was adamant that was all that was booked. As I was about to buy another room, Charlotte, told me it was fine, she had booked just one room she suggested we share. Needless to say that night, we didn’t have dinner, and Charlotte got the hammering of her life. We soon decided that we wanted to be together. The sex was amazing. Within a year, with a £8,000 ring. I went down on one knee and she accepted. We married at the end of 2019. Read more »

I unlock my boyfriend’s cock cage and gag on his cock [FM] [cuckolding]

“You wanna unlock me?” he looks up at you seriously, “I’ve been waiting for almost a month to cum, Princess.”

“No, not yet…” you say, trying not to sound too excited. You love the power he gives you.

“Please, Princess, I’ve been so good for you. I’ve been waiting.”

“Fine, go get the key, cuck.”

He moves quickly to his bag and rummages for it. He pulls it out, comes back over, and hands it to you.

“Sit down,” you command.

He does and you move the key around inside the lock until it pops open.

“Yes, that’s my girl, pull it off, babe.”

You do what he says and start moving your hand up and down his growing cock.

“Fuck, it feels so good to be touched. Wanna spit on it?”

You get off the couch and move between his legs on the ground.

“Fuck yes, that’s it.” he says.

You move your tongue up and down his cock before taking the whole thing in your mouth and down your throat. You keep going as he moans and says something like, “Yes, baby, all the way down, that feels so good.” Read more »

A Familiar Connection – Part One (Revised) – [B/S] Incest and Buildup

I woke up and checked my phone, reviewing my e-mails. One was from the hotel I was scheduled to visit in three weeks. I reluctantly opened it, already knowing what it would say: “we’re sorry, but with the current COVID outbreak, we’ve cancelled your stay.” Although this was expected, I was still disappointed. On the positive side, I now had a week of vacation scheduled which I needed to fill.

But before we delve deeper, I should provide some background. My name is Harry, I’m a 34 y/o man living in San Francisco. I’ve lived in the Bay Area most of my life, but never settled down or gotten married. I enjoy the city’s active social scene, and the adventurous playmates. Since my girlfriend and I broke up last January, I’ve been in a sexual lull because the swinger clubs are closed (fuck COVID). I had hoped to meet some people at the resort, but that’s no longer an option. Read more »

Life as a College Cuckold Boyfriend [consensual] [long] [some foot fetish] [MF]

*Note from the author: This story ended up being almost 3 stories in 1. Future installments will probably be a lot shorter, but leave your feedback below in terms of what you’d like to see. Note that this story includes more foot fetish content than my last one, but it is mostly in the last 1/3rd. While this story is a continuation of my last post, it should stand alone well enough to be read on its own.*

Now that I’ve told [our origin story](https://www.reddit.com/r/cuckoldstories/comments/m7zj1t/how_a_threemonth_breakup_made_me_a_cuckold/) to positive reviews, I can start getting into some of the other experiences Chloe and I have had over the course of our relationship. I think one of the things I’m most grateful for in our relationship is that we found and embraced this kink very young, whereas many don’t find it until much later in life. This allowed for a variety of experiences that usually only exist in fantasy, like the one below. Read more »

Grad School Friday Nights: Chapter 1: Andrew In The Library [Cheating][Cuckold]

Chapter 1: Andrew In The Library

I went to grad school for a number of reasons, so I could advance my career, so I could make important connections in the event I ever want to teach, and kind of just to do it. I did very well in undergrad so I was given excellent financial aid by every school I applied to. I don’t regret my decision to spend a little more of my twenties in academia, but sometimes it’s a little depressing when I see my college buddies already in the formal adult world with industry jobs, while I’m still… here, cramming for tests, doing homework, lab reports, and all that nonsense.

I was in one of the engineering libraries when it happened, I had overdue work for a class I was a TA for, just grading work along with answering the occasional email when I thought I’d look at instagram.

The girl in the first photo of my feed looked familiar, but I knew it wasn’t Sophia after a few seconds. I took a moment to look through her profile, she was someone I’d absentmindedly followed a few years earlier, after I saw her tagged in a friend’s photo and thought she was hot. I’d jerked off to her a few times in place of Sophia, but it was never the same. Read more »

Becoming a Hotwife [MF][Cheating][Public][Nonfiction]

“The first time I cheated I was in my twenties,” Stela told me.

We were in a quiet cafe in the middle of the afternoon. It was the first time we’d met in person after connecting on a dating app.

“I hadn’t been married long and I wasn’t very experienced when I met my husband. I was a good Puerto Rican Catholic girl if you can believe it. Sex wasn’t a priority for him. Even as newlyweds, it was only a couple of times a week and always missionary. Sometimes oral, but not usually. I wanted things I read about in novels and magazines. I was still working back then and I had an affair with my boss and got caught.”

She was obviously nervous as she told me. She fidgeted with her glass of wine, but I was confident I could put her at ease. It was her first time meeting a stranger, but I had plenty of experience.

“What happened next?” I asked.

“We worked things out,” she said. “We had a family. He made a lot of money and moved to the rich part of town. I quit my job and became a stay-at-home mom. Things were good. At least until my youngest kid started school.” Read more »

naked GF makes me jealous [mf][exhibtionist][cuckold]

the thought of other men seeing my GF naked gets me off and makes me mad at the same time

she is a 9/10-Norwegian blonde in her late 20s, a real goddess, with freckles all over, who always has the tiniest tan-lines when she goes on holiday

she goes every year to a yoga retreat with her girl-friend, who I also have crush on

neither of them are exhibitionists or anything, but they are more laid back about nudity than English guys like me

when they were away, she sent me some pics, also with other guests, who were all women, of different shapes and ages and it became like this fantasy island in my mind

one pic was a selfie of my GF and her friend sunbathing on their tummies, smiling into the camera, and I joked that it looked like they weren’t wearing their bathing suits

“Maybe we weren’t!”, she texted me back

later on that day, I was going to sleep at about midnight and suddenly I got a “ping! ping!” on my phone Read more »

[MMF] Cuckold Husband Pays to Watch His Hotwife Getting Fucked by Two Male Escorts

I had a memorable duo booking with Carlton from Anna’s Angels Agency. We were to entertain a couple who were driving all the way from Somerset to see us for a 1 hour cuckolding/hot wife session. It was to be a present arranged by Mrs Hot Wife for her husband, Mr Cuckold. They were nervous when they arrived, not really knowing what to expect as they were quite inexperienced having only tried MMF once before, many years ago with a male friend.

I got them drinks and sat down to chat with Mr Cuckold whilst his hot wife went to get changed in the bathroom. I did my best to set the mood as no pressure, let him know they’d be in control and the session would be all about them having a great time. I’m told I’m a very calming influence, especially with nervous, inexperienced types. By the time Mrs Hot Wife came out from the bathroom, with her impressive cleavage busting out from a tight little black dress, Mr Cuckold seemed much more at ease. After a chat with the two of them about their likes and dislikes, limits etc I contacted the agency to make sure Carlton was on his way. He arrived soon after. Read more »

More fun with Rachel and Tracy [MFF] – Part 11

previous parts on my profile

——–

I woke up around 7 am. Rachel was starting to rustle up. I went out to the hallway and heard noise from the guest room. I could only guess her BF was watching the videos and jerking off. I laughed to myself and made us all breakfast. When breakfast was almost done, Rachel announced “We can leave after we get video of him fucking me in the ass”. Her BF seemed excited at this. Rachel said they’ve done it a few times, but she wanted it with a real cock.

We cleaned up and then went to my bedroom. Rachel and I stripped, and started making out. I licked her pussy and made her cum quickly, hoping to relax her. I was rock hard and ready to go, I didn’t need help from her. I got lube from my nightstand, flipped her over, and got her lubed up. Her BF was hovering with the camera. Read more »