Our first steps in the lifestyle started in humiliating fashion even tho nothing sexual happened [humiliation] [best friend]

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My girlfriend Jessica and I are both in our mid twenties and have been together for about three years. This year I opened up to her about my cuckold fantasy and it has been amazing ever since. I was a bit shy to tell her at first because my knowing me you could not guess how much of a Beta I am but she loved the idea of dominating me. We had a lot of fun in bed talking about different scenarios and also role playing but we were very hesitant to truly try it because we didn’t wanted it to affect our day to day life and also Jessica is not the kind of girl who sleeps around with strangers.

Text here. Visuals inside.
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Talking about different scenarios I found that what made her hornier was when we imagined her sleeping with someone we know. Maybe because that would make the whole situation more taboo. Some time ago she suggested that I should fuck her for some days and I should not jerk off also. She would walk around wearing thongs around the house and I was dying to cum.

Now Jessica has this friend of her’s Alex who I don’t particularly like. To be honest he doesn’t like me neither. No specific reasons to it. Jessica and Alex never did anything together and they have been knowing each other for 10 years. Every time me and him were together we would argue about every topic. Now, one thing that makes me not like him even more is that not only is a bit arrogant and narcissistic but he is also taller and more muscular than me. So a bit of insecurity from my side I would say.

Since she learned about my cuckold fetish she often teased me talking about my friends and especially Alex. One night she invited him over to hang out and have some drinks and she told me she had a surprise for me. She had bought a chastity and wanted me to keep it on the whole time Alex would be there. It was so exciting. I didn’t cum in two weeks at that point and I was dying to just let myself go, but she made it even more difficult for me.

Alex came around 9pm and as I opened the door for him I felt like such a loser knowing I was locked. Jessica came out of the bedroom wearing some tinny shorts and a tank top. She was never so revealing around male friends, but this time I understood what she was doing.
She gave Alex a big hug in front of me and I immediately felt my cock trying to get free.
We started by having some wine and Jessica made sure to sit close to her friend touching him occasionally.

At one point she was laying on him while her feet where over my cock. She was playing with it as Alex’s arm was around her. They were watching some old videos on her phone while I was trying not to cum in my pants.
About an hour later when the wine hit her a little bit she went to grab another bottle of wine, Alex joked asking her if she had been working out as her butt looked more in share than before. Jessica laughed and told him she had always had a nice butt as she started shaking it a little bit.

I couldn’t believe they were talking about it in front of me. Jessica admitted that she has been working out and came closer to him asking him if it was really noticeable. Alex said yes and added that with those shorts it was pretty visible.
Jessica laughed and told him that usually she doesn’t even bother wearing shorts, as she prefers to keep only her panties on.
My cock was exploding inside the cage.
Alex kept joking saying they were friends for a long time so she can be comfortable around him. I couldn’t believe they were joking about stuff like that like I wasn’t even there, but I loved it.

“Don’t let me finish this bottle alone then or I would end up taking them off” said Jessica.

“No please, I don’t want your boyfriend to be jealous” Alex replied laughing

We spent the night like that, drinking and talking about different topics until Alex left at midnight. As soon as we were alone she asked me if I wanted to eat her pussy and without any hesitation I went for it. I loved the fact that she was wet as I understood she was also horny during that time. She came pretty quickly and after asking me to get her some tissues she turned the other side and told me good night. I was expecting her to release me from the cage and do something, but apparently she loved the idea of me being in chastity and told me I would have to wait a bit longer so I could enjoy more of her surprises.

Trying to sleep while I was dying to cum was extremely hard but I was also very curious to know where all this could go in the future.

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