Hello,
I got cuckolded half a year ago and I'm finally ready to write about it.
I'm a tall, skinny, white guy in my late twenties. I have a beautiful girlfriend named Anna who is also white and in her late twenties. We met a couple years ago and moved in together relatively quickly. Then quarantine hit and we were kinda stuck together. Not that we didn't have a good relationship. It was just that it would have been near impossible for either of us to move out, both financially and practically.
Soon after we started living together, I told Anna about my fascination with cuckolding. She was perplexed at first and didn't believe me. I stayed firm though and she eventually took me seriously. She had lots of questions which I tried to answer as best I could.
In the end, she didn't commit to doing anything. At the time in quarantine, we weren't sure how to meet people in the first place. But she did say she'd think about it and said if she did do it, it had to be 100% her decision for who, where, when, and how and there was nothing I could do to stop it once she made her decision. I agreed to her stipulation without a second thought.
Over the next few months, Anna assumed a more dominant role in our relationship. She made me do all the chores around the house. She also made every decision for where to go eat or what to watch on TV. Sexually, she didn't let me fuck her anymore and she wouldn't give me blowjobs or handjobs. Instead, she enjoyed long sessions of me licking her pussy and I was allowed to masturbate afterwards if she thought I did a good enough job. I loved it though and she seemed to settle into the role naturally.
We were both laid off at the start of quarantine. I was looking for new jobs without much luck for a long time. Eventually, I found a position at a small company basically as a secretary/accountant. It was a really small company too. There was a founder/boss named Mike who was divorced and in his mid to late 40s. And his son Brian who had just graduated high school at 19 was on the payroll as well though he didn't really do anything. That was it for the in-office employees. Everyone else associated with the company worked remotely in sales.
We worked in a small office park amongst several other businesses. Mike and Brian each had their own offices and I sat in a lobby in front taking calls, greeting guests, and handling accounting in general. Though he was the one to hire me, Mike made a lot of jokes about me being a male secretary. He talked about how he had hoped to hire a hot girl initially as secretary but just couldn't find anyone so he settled for me.
I took it in stride but it was always a bit weird to hear. Brian was even worse though. He was an arrogant kid who bullied me at every opportunity. He made jokes about me being gay, knocked papers off my desk, and gave me meaningless busy work to do. There was nothing I could really do since he was the bosses' son and even Mike laughed at his jokes and seemed to generally encourage his behavior.
I told Anna about Mike and Brian but she mostly brushed off my concerns. The most important part was that it was a job that paid money in her eyes. I waited until Brian was on vacation before bringing Anna to the office for the first time to see where I worked. I gave her an extremely short tour of the lobby and then Mike came out of his office to introduce himself.
After shaking hands with her, he jokingly exclaimed that he didn't believe that Anna could really be my girlfriend. She was so beautiful and out of my league. Anna blushed while laughing and then thanked Mike for the complement while touching his arm. Mike continued his teasing by telling Anna that I was the first male secretary he ever met and he would have hired her instead if he could have.
Anna giggled more while agreeing that a secretary was usually a girl's job. Mike added on suggesting that she could loan me a dress one day as a secretary's uniform. Anna laughed again and told Mike that he could call her if I ever violated the dress code or I wasn't living up to his secretary standards. This prompted Mike to get a pen and paper and she wrote down her phone number for him before we left together for lunch.
Later that night, Anna got a text from Mike thanking her for stopping by the office and saying she was welcome to come by anytime. She thanked him for his hospitality. He then asked her if she could send him a picture of herself to show Brian. He explained that Brian would never believe that I had such a pretty girlfriend. Anna agreed and made me use her phone to take some pictures of her while teasing me. She posed suggestively against the wall while asking if she looked hot enough for my boss. She eventually found a picture she liked and sent it to Mike. Mike responded by praising her beauty again. Anna enjoyed the game she was playing with me. She took off her pants, laid down on the bed spread eagle, and told me to lick her.
The next week, Mike couldn't stop talking about Anna. Brian was back from vacation and asked when he would get the opportunity to meet Anna as well. I tried to ignore his request but Mike heard and interjected by saying he'd invite Anna to come over later that afternoon for drinks. He texted her and she rsvp'd a minute later. Mike had me run out and get wine and beers from a nearby liquor store before she arrived.
Around 4pm, Anna arrived at the office. Mike and Brian were already in the lobby waiting for her. When she walked in, she gave Mike a hug. Mike then introduced Anna to Brian who also hugged her. After exchanging some brief small talk, Mike said we should have drinks. I served everyone, giving Mike and Brian beers while Anna took a glass of wine. Mike had tons of jokes, some at my expense, as we sat together in the middle of the lobby. Brian was less subtle and told Anna that he thought I was gay this whole time. Anna laughed though and said that she had the same suspicion too when she first met me.
Anna then accidentally spilled her wine on her shirt. Mike went into his office and gave Anna a spare t-shirt he had. Anna thanked him and asked if she could use his office to change. He said of course. Anna went in, closed the door, and then emerged 30 seconds later wearing Mike'a shirt. It was a size XL and looked massive on her small body. Mike joked that she could wear just his shirt and nothing else because it was so big.
Anna agreed and pulled down her jeans under the shirt to show Mike and Brian that the shirt actually made a nice dress falling at her mid thigh. She handed me her shirt and pants and then spun around and posed like a runway model while they cheered. We chatted a bit longer after that but then Brian had to leave to meet some friends. He gave Anna another hug and ran out the door. Mike told me to clean up while he took Anna by the hand to give her a tour of the larger business park. I picked up our beer cans and cleaned up the wine on the floor as they walked outside together. I finished cleaning and then looked out the window to try to see them. They were still holding hands and Anna was laughing wildly at some joke Mike just told.
They eventually came back inside and we said goodbyes. Anna and I left into the parking lot while Mike stayed in the office. When we got to our cars, Anna looked at me and said she left her purse in the office with a bit of a devilish grin. I said I'd go get it for her but she told me to go home and said Mike was still there so he could help her find it. Meekishly, I got into my car and watched Anna walk back into the office still just wearing his t-shirt. She knocked on the door and I saw Mike approach and let her back in with a big smile on his face.
He let her inside and I could barely see her crawl around under my desk to look for her purse. I'm sure she was giving Mike a good show of her butt. She eventually found it and returned to Mike who remained at the door. She gave him a hug. He put his arms around her back and kept them there as she pulled back and they started to talk. I saw Anna laugh once again and give Mike a quick kiss on the cheek. He returned her kiss on her lips and they continued to kiss for several seconds while Mike's hands wandered on her back and pulled up his shirt a bit to reveal her panties.
Eventually they broke off the kiss and Anna exited the office while blushing. I drove off home and Anna arrived home as well a few minutes after me. Once inside, Anna took off Mike's shirt. Wearing just her bra and underwear, she took a photo of herself in the bathroom mirror. She sent the photo to Mike telling him he was so naughty and he got her horny. Mike then replied with a photo of his erect cock which Anna made sure to show me. She then made me lick her again while musing about how big and nice Mike's cock looked.
The following week, Brian was on vacation again leaving me in the office alone with Mike. He texted Anna often and they exchanged more photos which Anna reviewed with me each evening. There was no subtle pretext anymore in their conversations. I knew they were gonna fuck and it was just a matter of when. Come Friday, Mike invited Anna to the office again and she happily agreed to visit. She arrived in the afternoon wearing a short black dress. Her nipples were poking out and I could tell she wasn't wearing a bra. We had some drinks together and I sat at my desk while Anna laughed at Mike's various jokes. Eventually, Anna said she had to go to the bathroom. Mike took her hand and led her to the bathroom while I remained in the office. After ten minutes, they hadn't returned so I looked outside. Just outside the bathroom, I saw Anna and Mike making out and groping each other. They eventually returned and I quickly ran back to my desk and acted like I hadn't noticed anything.
When they entered the lobby, they were still holding hands. Mike told me I could go home and I started to pack up my things. Anna came over to me and slipped her panties which she had taken off in the bathroom into my bag. I said goodbye while Anna said she was just gonna hang out a bit longer to finish her drink. Immediately after I left, Mike locked the front door and led Anna into his office. I walked around the building and peered through a small window in the back of Mike's office.
Through the window, I saw Mike and Anna kissing against his desk. Anna then stepped back and unzipped her dress to reveal that she wasn't wearing any underwear. Mike kissed and groped her more until eventually bending her doggystyle across his desk. He then dropped his pants and inserted his dick into Anna's pussy. I couldn't hear them but I saw Anna writhe in ecstasy. He went slowly at first but soon started to pound her quite roughly. He spanked her and even pulled her hair back to get leverage to shove his dick even deeper inside of her. This continued for over ten minutes before Mike pulled out and shot his load across her butt and back.
Anna stayed faced down on the desk while Mike took out his phone and took a picture of her covered in his cum. He then wiped off his cum with a tissue and Anna got up. She put her dress back on and then gave Mike a kiss before leaving. I left the window and ran back to my car. Anna walked to her car soon after and we both left the parking lot and headed home.
Since that day, Mike has continued to fuck Anna in the office or at his home on a near weekly basis. They sext all the time and I'm sure Mike has a treasure trove of her pics now. Brian found out eventually too and has not ceased to make fun of me and talk about how his dad is fucking my girlfriend like a whore.
Gibson - gibson341@gmail.com
