My Journey to a cuckolding lifestyle

[Shogun456]

Hi Everybody, I would like to share a short but true story on my journey. This whole journey actually took a long time before it happened but I summarized it as much as I could. This happened years back and was a start to an alternate lifestyle I did not imagine that it would happened. Nevertheless, I hope you all enjoy the story.

It all started with my ex gf R when we met in a strange situation. She was in a relationship at that point of time, but we were however starting out as friends. I knew that there was a guy in her life, yet I kept chasing and made sure to keep dating her. I was the 3rd wheel to the relationship that on the rocks. She would still occasionally stay over at his place before we would meet up for our dates. It was a strange time, I felt emotions that I have never experienced. On one hand, I was extremely jealous, on another, who was I to say anything, she wasn't even my gf to begin with. This ding dong lasted a couple of months and she finally had a clean break from her ex. When we were officially dating, we started being physical and started exploring having sex everywhere we could and this was the beginning of how kinky my ex gf was.


Firstly, she was a strong character with a really hot body, she was petite yet she had a nice pair of B cup racks and a bubble butt that was perfect for doggying. She knew the attention she brought about, but she also enjoys exploiting that sexuality of hers. She knew that guys lusted over her and she knew that she was attractive, that made her really desirable. When we first started out, I wasn't as experienced in relationships as she was and I knew that she had many bfs before me. However, on the plus side was a girl that knew her way around a man. She gave the best blowjob that I had ever received and she would do it at the kinkiest places you can think of. There was once we had taken a coach to Genting and she sucked me off under the blanket, cleaned up my cock and swallowed every drip of cum that I shot out and I knew that this kinky gf was going to be the best sex of my life. We started fucking everywhere, from public toilets, parks, car parks and blowjobs in the cinema, driving, plane rides, changing rooms. She would often dress really sexily, low cut tops, short skirts and she knew that she would get ogled at. I was really proud to have such a sexy and confident gf, but there was this emotion that slowly brewed in me, the jealously also brought about a growing erection in my pants, every time some one would try to look down her top or stare at her as she walks by. It was an extremely fun time that we had and with all these experiences that I had, in the back of my head I knew that it wasn't the first time she was doing all these kinky stuff.


One night when we were out drinking and I was curious, opening a Pandora box that I knew couldn't be close again as we chatted about her past. She was hesitant about sharing but as I urge her to be open and share more with me about her past, I felt an erection slowly grow as I stared at her attentively, sharing her detailed experiences about her sex life. I will fast forward the first few bf that she had as they were inexperienced and sex was mostly more mundane. She also shared that when we were started going out, she would still live with her ex and they will still engage in intercourse once in awhile. However, it was when she shared with me that she dated a guy 10 years her senior and that was when she began to explore and try out all the kinky stuffs that she had. He would photograph and video all the sexy fun time that they had. He would fuck her in any outdoor place that he could and get a blowjob from her anytime he wanted. I listened with a raging hard on that whole night and when we when home that time, the sex was explosive, I fucked her harder than usual, my erection was stronger and I had sprayed so much cum all over her face, her tits and her stomach, that long trail of cum all over her body was just a nice sight to behold. After that, my mind would often wonder when I was working, thinking of all the kinky positions that she would be in, even thinking of all the photos and videos of sex that she had with her ex and every time that happened, I would get a raging hard on and think about sex non stop.


I began reading threads about cuckolding/hotwifing lifestyle, I realised that I would get a raging hard on and really strong ejaculations as I read and imagine my ex getting into all sorts of positions and her getting intimate and physical. I started sharing this alternate lifestyle with her and she was shocked to hear about such a lifestyle, but nonetheless, she started reading forums, threads and it started off with her sharing how she got fucked by her exes while we were having sex. It was amazing how detailed and slutty she would be for her exes and every time I heard something new that we haven't tried, I wanted that experience as well. She would also share about her kinks, her fetishes and her turn ons as we discussed what type of man gets her all worked up. One thing about her, was her strong determination to always be in shape, she would be working out on days after her work and was constantly using the gym in her office after work. This was when she started noticing a colleague from a different department named C. One night halfway during our intercourse, I was just curious if anybody she knows actually fit into her criteria and turn her on physically. This was when she shared about her colleague C. He was tall and had big arms with a boyish face and a sunshine tanned. She described him as we we fucking and I could tell from her body that she was getting turned on, her pussy was getting wetter as she thought about C while I was drilling her doggy style. I was spent, shooting a huge load of cum, which trail all the way across her back and onto her ass, thinking of her getting intimate with C.

[showtalk]

Good start TS. 1st camper here!

[ILoveV]

good start. Support reporting

[_GG5_]

Support support!

[curious11]

keep it coming!

[Orange22]

Support and camping.

[StarIight]

Camping here! promising build up

[verywet]

any suggestions for BBQ food while i set up my camp fire.?

[MisterAW]

Interesting start. Tent pitched.

[merseyback]

Camping for updates too!

[enigma88]

Please continue.

[SirLance]

Nice start to story. Keep on going.

[Shogun456]

Thanks for the support and camping bros, the next instalment is here. Please enjoy

The devil inside of me urge her to try this cuckolding lifestyle and she was admitted to me that she felt abit kinky and curious to try. We laid out several ground rules, which the first and foremost was me giving the green light to anything physical and intimate. Secondly, was her giving me every bit of details as soon as she could or if possible even before her doing the deed. It sparked about a new unfound emotion and jealousy that I had. They had to contact each other because of a couple of projects which had to be handled across departments and the relationship was purely professional up to this point. However, one night after a couple of drinks together, she had took the initiative to engage with him in a conversation and this slowly began with them chatting more after that night. It began with normal chats and slowly it began moving to a more personal level. She was extremely open about their conversations, sending me screenshots and updates as soon as she could, the time stamp basically showed that they were flirting casually during work and the conversation was leading towards physical intimacy. Just an update about C, he was attached as well and his gf was working in a nearby office and would always arrange to meet up after work, even going so far as to wait for him when he has to work late. This made it difficult for him to try to have any sort of time after work which kept their rendezvous mostly during work hours.

The conversation started heading to a sexual level, with him sharing his personal turn ons and kinks. There was a particular dress that my gf wore on dress down Friday which was too revealing and short and that caught his eye, they even discussed on what underwear she was wearing under that short dress, he then requested for her to wear that particular dress to work. One faithful Friday morning, I saw my gf getting ready for work, with a nude colour bra and thongs, under that same white dress that was being discussed as she zipped the front up. She was giving me live updates on their conversations and the last sentence that she sent to me was a conversation about a time and place that was empty after work. There was radio silence for a while before her texting me, I am done, you can come over and pick me. There was alot running through my mind, my cock was extremely hard, my heart felt like it was exploding thinking of what could have happened in that brief period of time. However, I had made it clear to my gf that I was not ready for her to be fucked, I feel that I would not be able to take it if it had happened so quickly and she promised me that it would not happen until I was ready. I was waiting below her office and what was actually minutes, seemed like hours as she slowly appeared from the lift lobby. She had this really cheeky grin as she entered the car and she told me to drive to a deserted area to park the car. I was anxious, anticipating for her to spill on the deeds that just happened. However, she told me to be patient and reassured me that she would share every single detail with me when I parked. The drive that was only 10 mins felt like eternity as I quickly drove up to the highest level of the MSCP.

She looked into my eyes and blow her breath in my face and it had the familiar smell of cum in it. She just smiled coyly and told me that they had planned to meet at a meeting room that was not booked or used for the day. Her every step was filled with excitement and anticipation as her pussy began to get moist thinking of their rendezvous. She reached the meeting room, scanned her pass as the door slowly opened and there he was waiting for her. They wasted no time and started hugging and kissing as they knew that they could be caught any moment if some one decides to enter the room. His hand was auto roaming her ass finding his way down and under, grabbing her bare butt which was cladded only with her thong. She moaned every time his grip tighten and his fingers were feeling up every inch of her butt. She rubbed his nipples and they were erected as her hands began roaming south, feeling his hard on from outside his pants. She took the initiative to take a step back, while still locking in a tongue fight and began unbuckling with his belt. She removed it with ease as she unclasped his pants, pulled down his pants along with his boxers, releasing his hard erected cock as she ran her fingers up and down while using her other hand to caress his balls. She could hear the moans as she stroked his member up and down. His hands were not idle as well, her front zip of her dress was easily pulled down all the way to her waist, exposing her bra cladded tits as he began squeezing and kneading her tits. She in return was moaning when he felt his palms reaching under her bra cup gently groping and flicking her hard erected nipples. She knew that she didnt had the luxury of time as she began to break free from their kiss and began kneeling down.

She started describing his penis to me as I could see her constantly giggling while sharing her experience. It was long, thick and arched as she started running her tongue on his pee hole and he let out a groaned. She was playfully teasing him, using her hand to massage her balls, the other hand stroking his cock and using her tongue to go round his dickhead. All this while, my erection was bursting inside my pants as I was constantly fidgeting and trying to adjust my hard on. She caught on and she told me to just enjoy what she did to him. She alternated between sucking my cock, stroking it and telling me what happened. I was totally in heaven, I could feel the jealous and ego burning inside yet on the other hand, thinking about her experience and her being a slut for another guy's cock made my erection harder and stronger. He begged her not to tease him any longer as he wanted his cock deep in her mouth. All this while, she was constantly looking upwards as she work on his cock and in one swift motion, she took his whole cock into her mouth and started sucking hard and fast. Perhaps it was the excitement building up, the fear of being caught, the taboo of getting blown in the office, she could feel his balls tightening, his moans and groans were louder and heavier. Under that deep breath, all she heard was I am cumming and that made her tighten her lips around his cock, bobbed her head back and forth as fast as she could as she felt a strong squirt and the distinct moaning sound of "ahhhhhh" as his cum slowly started filling up her mouth. She swallowed as much as she could, but she admitted that it was alot, more than she ever swallowed before as the overflow of his cum started leaking out from the sides of her mouth, flowing down to her neck and her breasts.

In my mind, I thought his POV had to be amazing, she was still on her knees, mouthful of cum as he could see it running down all the way to her cleavage. They took a couple of minutes composing and getting dressed before quickly making their way out of the room .We moved to the back of the car, I couldn't take it as I needed to fuck her there and then. Her pussy was already leaking when I removed her thongs, my cock slipped into her pussy with ease. It was extremely warm and wet as I pumped her with her dress on. She then teased me, unzipping the top of her dress and told me to avoid kissing her breasts. She asked me to take a sniff and the smell of cum was so strong as I could see abit of cum stain on her bra. She admitted to me that she didn't clean up and came down immediately after the whole ordeal. That was the last straw for me and I couldn't hold it in any longer as I removed my cock from her pussy and shot my load all over her breasts as well. The ejaculation was stronger than expected, it was a mess, it landed on the car seat, her hair, one long trail across her face and lastly a tiny pond on her breasts as I was spent laying beside her.

[StarIight]

That was a fucking hot update

[funfox]

Awesome story. Thank you TS