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I am 28 and have been with my 25yo girlfriend Jane for a couple of years now. Jane is stunning hot, she is curvy in the right places, big boobs, big round ass. I had a couple of relationships before I met her but they were very vanilla and not really for me. From the moment I met Jane I understood that she was nothing like my exes. Sex with her was amazing, she was super fun and always open to try new things in bed. We did role play a lot right from the start talking about cuckold and threesomes. Jane was open to try everything but I was very scared to enter the cuckolding lifestyle although I loved it as a fantasy.
She loves to mention people I know when we talk about cuckold and she knows how much I enjoy the humiliation. Objectively I would always rather try it with a stranger but things became very intense when she started mentioning a guy from my work. I would watch soccer matches with him from time to time and we also supported two rival teams.
Jane asked me if I wanted to invite him to our place to watch the match and maybe she could offer to suck his cock if his team beat mine. I was so turned on by the idea but also not sure if I wanted that to happen. I finally made up my mind and invited John to our place.
Thinking about it John was perfect for this as he was cocky, loved making fun of me especially when my team lost so I was sure he would love the idea of my girlfriend sucking his cock.
He came by my house the day of the match an hour prior to the game. Jane was immediately super flirty with him. She told him she would support his team and was touching his arms every chance she got.
John looked very confident around her and after a couple of drinks he turned his whole attention to her. The first half ended in a draw and Jane caught the opportunity during the break to propose to us the idea of her giving head to the winner of the game.
John looked very surprised but he was in of course. She made sure to humiliate me by cheering loudly for his team as she was begging to suck his cock. At the end my team ended up winning, so not quite as we planned. Jane was caressing his leg while he was blaming the ref for the loss as he always does. I thought the night would end there but at some point they were staring each other before John stood up and pulled down his pants.
This brought a smile to her face and she didn’t hesitate pulling down his underwear and put his cock in her mouth.
It happened so fast I couldn’t believe all that was really happening. Jane was going hard on his cock as he was pushing his cock deeper in her mouth. Jane had no gag reflex whatsoever so it was going all in. I thought all that would last a couple of minutes but I was wrong. John had a lot of stamina and after roughly 10 minutes he told her to bent over on the sofa. I froze. The deal was just a blowjob but they were both enjoying it so much they totally forgot i was there. He pulled down her shorts and as she was extremely wet already this made it easy for his cock to slide in.
He went hard on her from the start and looking at her face she was loving it. She kept telling him how big his cock was and that it was the best cock she ever tried. At that point as I was grabbing my cock hard trying to not to cum, that pressure and her being so bold in humiliating me made me cum in my pants. Jane noticed and she just smiled at me as John kept fucking her. The post nut clarity hit me hard but I really couldn’t move. For the next 4-5 minutes I kept looking at them while my mind was racing. I felt regret and humiliation but I had to accept it.
At one point John was going faster than before until he ordered her to get down on her knees again. She obeyed immediately and stood there with her mouth open as he was jerking off fast. I couldn’t believe my eyes. In a few seconds John shot his load all over her face and most of it ended in her mouth. That motherfucker made sure to humiliate me well, not only by fucking my girlfriend that way but also by cumming in her mouth. Jane swallowed it all and then turned her eyes at me. She stayed there smiling as John was rubbing his cock on her cheek.
She then stood up at sat next to me without saying nothing. John told me that at least I could be happy for my team winning. He laughed and went to the bathroom to clean himself. As he left Jane sat on my lap and passionately kissed me. I couldn’t believe Shen was doing this right after he came in her mouth. She kept going making me tase everything. After a while John came out of the bathroom and got dressed. She saw us kissing and just laughed before telling us good night and leaving. Me and Jane ended up in bed and I asked her multiple times if she meant it when she said his cock was the best she ever tried.
She wouldn’t respond to me just to make me more and more miserable but seeing how desperate I was she said we were equal. Although it was clear she was lying. We entered our cuckolding lifestyle that night in a very humiliating fashion but that was just the beginning of it.