My Girlfriend hooking up with my Boss!

By: Nicole's Cuck

Hello,

I never thought of myself as a cuckold growing up but I realized by my mid twenties that every girlfriend I ever had cheated on me. My first girlfriend in high school, my two girlfriends in college, and my last girlfriend after graduating all cheated on me at some point. This usually led to my girlfriends ending our relationships, despite my general willingness to forgive and keep trying. The one exception was my last girlfriend who kept dating me after 'accidentally' cheating on me at a party where she got too drunk. A few months later though, it happened again and then she ended our relationship.

After that last breakup, I started to fantasize about my ex-girlfriends hooking up with other guys and imagining the series of events that led to them cheating on me. It became a bit of a fetish and was soon the only scenario that I thought of while masturbating. I also started to think more about the guys they had cheated on me with. They were all acquaintances and classmates of mine who I considered jerks or assholes even before they fucked my girlfriends. My girlfriends had said that they appreciated that I was a 'nice guy' but they all gravitated to the other extreme when cheating on me.

I was sinking deep in this cuckold fetish by the time I met my current girlfriend Nicole. We met at work and bonded over complaint about our mutual boss Victor. We called him the evil Michael Scott because he routinely said and did inappropriate things but he didn't have any redeeming qualities or humor. He was just an arrogant boss who made our jobs uncomfortable at all times. We had to eventually disclose our relationship to the company so Victor knew we were dating but we tried to keep relationship hidden from our other colleagues just to avoid the inevitable awkwardness.

Nicole was a bit more liberal minded and sexually adventurous than my previous girlfriends. I definitely enjoyed her proclivities early on in our relationship but it became clear over time that I couldn't provide everything that she desired. She wanted a guy who really took charge and drove the action but I was just following her lead the entire time. Seeing her frustration, I felt like I had disclose my cuckolding fetish to her.

I didn't expect for her to sign on to becoming a hotwife but I just felt like I was hiding my true self from her at some level. To my surprise though, she was very accepting the idea when I first mentioned it. She said she was sorry that I was cheated on so often but understood how that could become a bit of a fetish over time. And when I said jerks and assholes provided some sexual gratification to my previous girlfriends that I couldn't manage, Nicole agreed while explaining that I respected my ex-girlfriends too much and couldn't treat them like the sluts they wanted to be.

After our long conversation, Nicole finally asked me if I wanted her to hook up with someone else. I said yes meekly at first and then again with more conviction. Nicole then asked who I wanted her to hook up with. I said I didn't know and that it was ultimately her choice. She agreed that it was her choice but asked if I wanted the guy to be an asshole like the previous guys my ex-girlfriend's had hooked up with. I said that it was my general preference but again that it was 100% her choice.

Nicole then chuckled and said that she should hook up with our boss Victor then. I immediately said no. I could hardly believe what that would feel like. Nicole explained that Victor checked all the boxes. He was someone we both knew. We both agreed he was a huge asshole and that it would be completely humiliating for me if he was the one to make me into a cuckold. And both of us were certain that he would do it if Nicole let him. He had made sexual remarks about Nicole countless times in the past and wouldn't hesitate for a second to fuck her. I asked Nicole if she wanted to hook up with him though. She thought about it for several seconds before saying that it would make work a lot more fun at least.

The next week, Nicole made a conscious effort to wear more revealing outfits at work. It wasn't anything too overboard but she wore some outfits that were previously reserved for weekend outings. Our office was 90% men so it led to Nicole getting more attention from a lot of guys. Victor took notice too and found every opportunity to chat with Nicole at her desk throughout the week.

And instead of reacting sternly to him like she normally did, Nicole was now much warmer to his advances. She laughed at his jokes and even let him give her a hug. It was surprising how quickly her plan was showing results. Sitting at my desk and watching Victor oogle my girlfriend on a daily basis, I struggled to contain a mix of jealously and excitement. But Nicole said that was all the more proof that I really wanted this to happen.

Things continued to devolve over the next couple weeks as Nicole increased her interactions with Victor and even started to stop by his office just to chat and ask how he was doing. Victor obviously relished the attention and even invited Nicole out to lunch one day. Afterwards, Nicole laughed when I described her lunch as a date. She explained that they just chatted about life while enjoying a couple drinks over lunch. And she acknowledged that Victor had mentioned me and asked about our relationship but said her response would stay between her and Victor.

Victor's assistant Lilly had been very pregnant this whole time and was starting to become suspicious of Nicole and her newfound 'friendship' with Victor. Luckily for us though, she went into labor the next week and started her maternity leave before being able to pry to deeply into Nicole's motives. Lilly travelled with Victor wherever her went typically. But with Lilly out of the picture, Victor asked Nicole if she would join him on his upcoming trip to a sales convention and be his stand-in assistant until Lilly came back. Nicole accepted his offer knowing it meant flying on a plane together and staying in a hotel with him for multiple days. When discussing the trip later with me, we both concluded that if anything was going to happen between Victor and Nicole, this was likely the best shot.

Before she left, we went together to the mall and I bought Nicole some new dresses and lingerie. The lingerie was see through and very sexy. I asked to see her model the lingerie when we got home but Nicole teased me and said it was for Victor's eyes only. I dropped Nicole off at the airport later that evening and gave her a kiss goodbye. She said she was nervous but also excited.

Nicole texted me from the airport saying she had met Victor and they were about to get on the plane. I wished her luck and asked that she keep me updated on whatever happens. Nicole replied with just a heart and kiss emoji. I was a bit of a wreck for the next several hours until Nicole messaged me again. She explained that Victor had a seat in business class while she was in coach so there wasn't much opportunity for anything to happen on the plane. They took a cab together though to the hotel and got rooms that were on the same floor not too far away from each other.

The next day, Victor and Nicole went to the convention together. Nicole described it as very busy and she just shadowed Victor most of the day and took notes. She took every opportunity though to laugh at his jokes and fawn over him. Nicole said that he was responding to her attention and put his arm around shoulders and waist several times throughout the day to help guide her through the crowds. And in an elevator at one point, they had to squeeze in together in the back corner to let more and more people in. Nicole said her entire body was pressed up against his and he put his arm around her back to hold her close. And after some people exited the elevator, he kept holding his arm around her and they were essentially embracing each other until they got to their floor.

At the end of the day, they got a cab together to take them back to their hotel. As they sat in the back together, Nicole said she let her skirt ride up a bit and leaned her legs towards Victor. He then put his hand on her bare thigh and stroked her leg until they arrived at the hotel. Once inside, they went immediately to the bar and shared a drink together. Nicole continued to lean against Victor and touch him as much possible. The bartender mistook them as a couple which made them both laugh. But then when they left to go back to their rooms, they got in the elevator together. It was empty this time but Nicole joked that the back corner was their spot. Victor walked over to her and put his arms around her. She looked up at him and he leaned down to kiss her. Nicole reciprocated his kiss and they quickly started making out and fondling each other in the elevator.

When they got to their floor, Victor held Nicole's hand and led her to his room. Once inside, they resumed kissing while Victor pressed Nicole against the wall. As they kissed, Nicole eventually managed to slip her dress off her shoulders, revealing the see through lingerie that I had bought her the day before. Victor stepped back and admired her body. He then pulled his phone out of his pocket and explained to Nicole that he needed to record her consenting since he was her boss. Nicole said she was simultaneously anxious and horny as Victor began to record her.

She tried to pose and look cute for him. He asked her if she wanted to suck his cock and she said yes while quickly getting on her knees. He then unzipped his pants and Nicole pulled his cock out. She started stroking it and Victor asked if it was bigger than her boyfriend's (me). Nicole nodded yes while he continued recording her. Victor then demanded that she say it. Feeling like a complete slut, Nicole looked up at the camera with his cock inches from her face and told Victor that his cock was huge and much bigger than me. And without prompting, she started to beg Victor to please let her suck it. Victor laughed and called her a good bitch before thrusting his cock forward into her mouth.

Recounting everything that happened afterwards to me over text, Nicole explained that she sucked his cock for at least ten minutes while he continued to record her and make degrading comments. He called her a slut and said he knew that she had always wanted his cock in her mouth. Every comment though increased her horniness and made her even more wet. And the presence of the camera recording everything heightened her experience to extreme levels.

Eventually Victor led her to the bed and told her to strip for him. Nicole took off her lingerie as he recorded her from every angle. Nicole started rubbing herself and begging Victor to fuck her. Victor said that once he fucked her that her pussy would be his forever. Nicole agreed and said he could have her anytime and anyplace he wanted. Pleased with her response, Victor then inserted his cock into Nicole's spread legs and "fucked the shit out of her" (Nicole's quote) for over an hour... in every possible position and having Nicole suck him again between every transition. Victor kept recording the entire time and basically got a full POV amateur porn movie for himself. And at the end, he pulled out and shot his load across Nicole's face. She then sucked his cock clean as his cum dripped down her face.

Victor finally stopped recording and Nicole cleaned herself up in the bathroom. Nicole said she could hardly walk and felt bow legged after the pounding she received. She put her clothes back on and Victor walked her out of his room. Their flight back home was the next morning and Victor asked Nicole to come back in the morning to wake him up. Nicole promised she would and then went back to her room. Once inside, she started texting about everything that happened and I jerked off while reading about every sordid detail. I couldn't believe she had let him record her. She said she loved it though and was planning on waking him up early the next day with another round.

Nicole will fly back tomorrow with Victor and we'll both have to contend with a boss that will undoubtedly fuck her regularly for the forceable future.

Nicole's Cuck - mahmiss@tutanota.com

Other Couples' Blog Submissions:
Humilated by my Wife & best Friend
She Fucked the whole Bachelor Party
My Husband set me up with a Married Man