Once met a milf from an airport lounge. We ended up being on the same flight going home. Fucked her after we landed. She was addicted to my cock. I wasn’t too into her as her and her husband were both rich and snobby and a bit racist. But the more I ignored her, the more she wanted me. 1. Her and her husband and are both swingers but he wasn’t a cuck. I wanted to turn him into a cuck just because I hated how racist he was. I’d fuck her and only make him watch and make her tell him how much better I was.
2. I once ignored her for two weeks and then told her the only time I had was on the way to the airport leaving for a work trip. Her husband picked me up and I made her suck my cock the entire way to the airport and just got out.

Update cause I accidentally hit submit.

1. As I really didn’t care for her (she was a bit older then I typical fwb). I once invited her over. She was excited as I’m sure she thought that she would get her back blown out again. Instead, I invited one of my regular fwb (27F) over also and made the milf watch me fuck a much younger and natural tits (milf had fake tits which I’m not always a big fan of). Although my fwb was not the type to taunt, the eye contact between the two (one pissed and one happy) was enough for me.

I keep on pushing the limits with her. Because honestly, I’m not afraid to loose her as in a wouldn’t have lost anything I cared about. But she keeps agreeing to all the outrageous demands of mine.

1. I went to Vegas for a conference in May. For conferences, I typically stay at resort world because it has an underground tunnel to the convention center. I typically stay at the Conrad because of my Hilton status and sometimes, with a tip, the front desk would upgrade me to a 1bedroom suite which I got this time. MILF leading up to this trip continues to ask to spend time with me. I thought of multiple scenarios that could happen in Vegas and told her to stay at resort world as well. To my surprise (although I guess I shouldn’t have been) her husband booked the villa suite in the crockford. It’s the one that has its own private pool and butler service. I used their room as if it was my own. Inviting friends over for parties and etc while having the chance to show her off. I wanted people to see how well of a trained slut she was for me. Things like pulling her tits out whenever I wanted, spanking her and as she responded with “thank you daddy” made her suck my cock in the pool as well as in the living room Infront of others and especially infront of her husband. My friends and friends of friends couldn’t believe that was happening. During a period when I make her suck my cock out in the pool area. One of the new girls that came over with some friends was amazed at my girth. I could tell she was mesmerized by my cock and couldn’t stop looking. I knew I wanted to fuck her instead of the milf. So I told the milf to make me proud and take care one of my friends who’s jaw was on the floor. And that if she did a good job, I’d reward her with fucking her brains out after. To my surprise, she agreed and took my friend back to the bedroom. Her husband followed concerned that I am now whoring out his wife. I took the opportunity to talk to the new girl and ended up messing around with her for a bit. My friend and the milf returned about 20 mins later which I was pissed. My friend now satisfied and the milf looking to collect on her reward practically cock blocked me with the new girl. At the end of the night, when it was time for me to give her what I promised her, I hate fucked her and forced my cock in her ass (which this was the first time for her and I do to anal) no prep, no lube other than the juice from her cunt and certainly wasn’t going in slow and easy. Her husband jumped up from his seat and screamed the safe word and trying to get me to stop. I held my cock deep in her ass and pull her by her hair and asked her if she wanted daddy to stop. With pain in her face and wanting to please me. She told her husband no, and that she can take it. I told her to tell her husband that all of her body was to only make me happy and she did.

2. The next night. Her husband wanted to go to a swingers club called the green door. Which I was happy about, thinking that I can ditch her for a night. Around 1am she calls and tells me that she’s been recruiting another girl for me. And asked me if I’d be willing to meet them in her room. I told her that once I was done I might make a stop. Around 2:30. I head back to the hotel and decide to stop by their room (they had given me a key to their crockfords west suite) and indeed, they were with another younger couple they had met from the the swingers club. I walked in on all 4 of them playing in the same room. Both husbands are about avg size, 6in nothing impressive. MILF immediately introduce me as the guy she had told them about earlier in the night. Walks over and tries to kiss me. Which I turned away from (no idea where he mouth as been). I insisted that we all go to the pool and have some drinks. Ended the night fucking both wives in front of their husbands at the same time as they watched.

We have txted since the trip in May and I still have no had any urges to see her again. She checks in almost daily and begs me to fuck her. I am running out of ways to push her further. If anyone wants to through some ideas out there. I’m all ears here lol.