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See Part 1:
After our threesome, we felt like we needed to see Ryan again just to resolve any awkwardness since he had left in such a hurry, but not soon enough that he started to expect it to be a regular thing (even though we both wanted to do it again, and soon, we wanted him to stay in the role of “casual plaything”). But Summer started soon after our first experience and scheduling got a little tricky. Ashley went and met him for a solo lunch date and ended up blowing him in our car. She was really embracing the feeling of being “slutty” and I encouraged it. This happened a couple of times and then he moved away again. We would eventually see him again for a do-over of our original experience when he came home for Christmas the next year, but a lot would happen before then.
Ashley was concerned that I might regret the experience, or feel jealousy, but I didn’t feel anything like that. And what’s more, she really stepped up her game in the bedroom. She started training her ass and we started having anal once a week. She even started wanting to fuck in our hot tub where the neighbors could see, but we only did this briefly before we realized how risky it was starting to get. But we started hooking up in public places a bit more carefully and it was exciting.
In the meantime, later that year we had a trip to Ireland, and she was excited to be in another country where she could really be openly promiscuous with a lot less caution. No kids. No acquaintances. Just a different hotel in a different town every night. It was great. And by this time, she had really gained confidence that I liked her “slutty” side, that other men were attracted to her, and she wasn’t holding back. When she saw a guy she was attracted to, she would just instantly go hit on him. We were there for 10 days, and she was able to make several hookups happen.
The first success was a young man in a pub. They hit it off really fast, and she pretty quickly told him about our recent experiences and interests. He said he was really into MILFs, which I think threw her for a loop as she suddenly realized that yes, she was, compared to him, a much older woman, but whatever. He was still down. He came up to the room and it was almost like a scripted repeat of our experience with Ryan. She started blowing both of us. Lots of giggling. We moved to the bed and as things heated up, tried DVP. We had learned this time that I did well in the rear position: he lay on his back, she mounted him and rode him for a bit, and then I entered in doggy style. It was a little less awkward this time and I made it in, but it was a little tight for her to enjoy thrusting, even after more sex just to warm her up a bit more. We were still surprised, because he was a bit smaller than me and the dildo, it should have fit better, but I guess the angles were different. She usually didn’t need much warmup before I could do the double insertion at home, she’s always taken it like a champ. But bodies will be bodies and you never know. So I backed off, and just suggested she let this young man have the night of his life, and he went for it. He ended up finishing in her throat with a rougher throat fucking than she had done before, which she thanked him for – that was cute. He left, again, seeming to feel a little embarrassed and awkward after his nut with the husband watching.
A few nights later we were staying in a very fancy hotel and she approached an older English gentleman who was also staying there. It took her longer for the conversation to become so open, but she eventually expressed her interest, and he expressed his: he would love to spend the evening with her, but he didn’t like the idea of a threesome. She told me it wasn’t going to happen, but when she said that it was just because he wanted only her, I said she should definitely sleep with him. I gave her the room key and said I would just make myself scarce until she texted me that she was ready. It turns out that was unnecessary, because he had a much nicer suite and invited her there, where he made love to her in a very gentlemanly fashion, and then she met up with me, again worried that I might have been jealous. But no problem there! But we were starting to realize she didn’t like “gentleman” so much. He really enjoyed how forward she was and how quickly and eagerly she wanted to give him head, but he wasn’t much to speak of in the bedroom. She wanted something rougher. As I wrote Part 1, I realized we should have seen this sooner too. She liked Ryan being rough. She wanted it harder than I was giving it to her. To me, sex was an act of worship. But she wanted a guy to use her. This guy had made her feel like a million bucks and raised her self esteem, but he hadn’t brought out her slutty side like she wanted. Humorously, it hadn’t occurred to me that she had never encountered an uncut cock, and when she told me about how weird his cock looked, I had to chuckle and explain what that was about.
Our final hookup was a taxi driver who clearly worked out A LOT, and she was curious about being with someone with that physique. She gave him her number and said to text us that night, and he actually did! (I know this story sounds like one slam dunk after another, but there was plenty of rejection and flakes along this journey, you’re just getting the highlights – him texting us and actually showing up was a really big deal, and it really made our night). He came to our hotel and we chatted for a little while, before inviting him upstairs. This time we both had sex with her for quite a long time before we tried DVP, and this time finally we both got in there and could comfortably thrust, and this time… she was transported to another plane of existence. I think she enjoyed having her hands on his very well-developed chest muscles, and he was gripping her ribs and arms and really man handling her. I was worried we might get in trouble with the hotel for how loud she was screaming. She said she didn’t even know how many orgasms she had, because once it built up, it was just constant waves of pleasure. Eventually she tapped out and we all laid there for a while. She hadn’t wanted to stay long after with her English Gentleman friend, and no one else had lingered. Eventually when we had collected ourselves, she invited him into the shower with her and worked him back up to finishing in her mouth before he left.
It was at this point we started to really talk about her fantasies more. She wanted to fuck a really big guy, who could pick her up effortlessly and carry-fuck her. She had wanted it with the cab driver, but felt nervous saying that. And she wanted it rough. She wanted to fully embrace being the “slut” in the room. And even though she really liked DVP (and we were doing DP with me in her ass and a dildo in her pussy regularly by this time too), she liked it when one guy just really went for it with her and wasn’t trying to coordinate thrusts with someone else. And this was when we started openly looking for a “cuckold” experience with a muscular bull…