**LOOOONG Backstory (sorry, I just started typing and couldn’t stop. You can skip this bit, it’s not that interesting)**
Me and my SO are both bi and so ever since the start of our relationship 4 years ago, we’ve had an understanding that we are free to do anything with people of the same sex, and, because we’re not too worried about that, also members of the opposite sex. However, until recently, we hadn’t really discussed this to any great length or acted on it.
We’re soon going on a holiday to Amsterdam where, last time I went, before we were together, I enjoyed the company of a ladyboy hooker. My SO loved this idea as she’d never been with a ladyboy, and wanted to do this herself. Knowing that she can be a little shy at times (she’s been getting steadily better over the past 4 years), I realised that there’s a good chance that she’d be too worried to suggest doing anything while we were there, and I really didn’t want her to come home regretting missing the opportunity.
I decided that a good way to deal with this would be to be a bit naughty before we go by having a threesome with a guy, so that she knows we’ve already crossed the “cheating” bridge and that we’re both ok with it, so she can let loose on our trip. Alongside this, a few other things have led me to want this for her, but this was the main catalyst for me putting some time aside for us to have “a talk”.
The talk went well. She was actually surprised that I felt the need to discuss it, but as the days/weeks went by, she realised how important it was for us to lay out rules and really go into depth with some of our fantasies related to having other people (amongst other things, she REALLY wanted to watch me suck a guy’s dick as I have quite a reputation for being rather talented at this and I REALLY wanted to watch her being fucked by another guy). As part of her shyness, it’s taken a bit of work for her to open up about a lot of her fantasies in the past, but we’ve always been on the same page about everything.
So we got ourselves an app to start looking for nice guys and, with the one weekend off a month we get, have gone on a couple of dates and even arranged for one of them to come to our house for a fun afternoon. That brings us to two days ago, when the guy cancelled. But we had our weekend off, and with our holiday not far away, we weren’t prepared to go unsatisfied, so we decided to go to a sex/swingers club near us, something we wanted to do, but thought it might not be the best first step into this lifestyle.
**Starting the Night**
We had some fun getting her dressed up for the night. Not really understanding the quite vaguely worded dress code, we put a lot of thought into it, though it was too last-minute to really do any shopping for it, so we just decided I’d wear boxers. Her outfit was much more stunning though – lacy red lingerie, a sheer kimono, sexy heels and a blonde wig (her hair’s always different – natural, wig or dreadlocks, depending on her mood). She looked absolutely stunning and it took a fuck ton of willpower to not just pounce on her then and sap our horny energy before the night started.
We got to the club and were met with very warm greetings, instantly ousted as newbies. We were given a tour of the rooms and rundown of the rules. Everyone we spoke to assured us of being safe, easing our way into things and not feeling that we have to do anything we were uncomfortable with.
So before we jumped into anything, we sat in the bar having a drink, purposely in a corner so that we could chat, get our bearings and discuss our plan of action. We decided to do a lap of the place, see what we could see and learn the layout a bit (by the end of the night, it was still a little bit of a maze to us), so we did just that, chatting to people occasionally as we wandered, everyone assuring us that we can take it as easy as we like and to not do anything we were uncomfortable with.
After a few hours of drink in the bar, wander round, chat to someone and repeat, we decided we should try something a little naughtier and go into the pool. We got out of our underwear and into towels and we headed off there. I was happy to strip off straight away and plunge right in, but my SO was a little more timid, instead opting to sit at the side, cutely swishing her feet in the water. After some gentle persuasion from me and a guy we’d chatted to quite a bit a few times throughout the evening who we were very at ease with, she felt happy enough to get naked and get in the pool. We had a lovely time chatting with him and he was again very cautious to not offend, asking occasionally if he was ok being so close or if it was ok that he was playing with himself while we chatted and such.
**The Real Fun Begins**
Having enjoyed the pool and rinsed ourselves in the showers in front of everyone, we again regrouped in the bar and decided we should do more. So we headed to the couples room with the intention of playing with each other and maybe getting involved with someone else we found there.
What we walked into was… loud. From a tangle of bodies a couple of women were screaming loudly from successions of orgasms. For me, this was a great atmosphere. I didn’t feel like I was intruding and I didn’t feel like there was too much attention focused on us.
But the latter wasn’t entirely true. I took my towel off and got on the bed. My SO laid back, pulling her towel open with utter confidence and comfortableness, looking absolutely divine, and we started kissing. Before we knew it, we had been approached by a really kind-faced older gentleman, who asked if he was ok to talk to us. We said yes and soon he asked if her could kiss and touch her, which we again agreed to. My SO has the most gorgeous, heavenly boobs I have ever seen, so this man was grabbing them with gusto. I loved it. I loved watching the enjoyment on her face and I loved the eagerness with which another man was enjoying her amazing body.
Before very long, another guy approached us and asked her if she likes being licked. She said yes, he asked if he could and she again said yes, and so he proceeded to go down on her and play with her with his fingers. He would go on to make her orgasm an unfathomable amount of times like this (she can orgasm A LOT, and this night was a prime example of this), though not by fucking her, as he mostly liked to please. Another guy who we’d eyed up earlier in the night also made his way up to her, again asked permission to touch her and started to enjoy her. He soon put his dick near her face and she eagerly, hungrily started to suck him. He also had a go at going down on her, and him and the other guy were discussing her like a sweet delicacy, absolutely in love with the taste of her and in awe of her body. I remember looking at her face while we were all touching and pleasing her, thinking she looked like a goddess being worshipped. She agreed that’s exactly how she felt.
Meanwhile, however, the older gentlemen who’d first spoken to us in this room had asked about our sexualities and was quite pleased to hear that I was bi. Part way through this worshipping, me and him had moved off to the side to kiss and, before long, I was sucking his VERY thick dick, putting my 4-years-out-of-practice dick sucking skills to the test. I wasn’t disappointed with myself, being able to take his whole length every time.
Me and my SO kept looking over at each other, getting even hornier each time we saw what the other was doing. Her moans and facial expressions were driving me crazy, as were the hands all over her, and the lustful looks on the faces of the guys who were enjoying her. She was enjoying watching me suck a dick just like she had long wanted, and watching the guy I was with shaking and tensing up, moaning in pleasure at using my mouth. She said I must have absolutely made his night by how much he was enjoying it.
My guy grabbed me to kiss me for a bit and asked if I wanted him to cum. I said “Not with my mouth up here” and got back to my job, earning myself the lovely mouthful of cum I’d been craving for so long, swallowing every last drop, still gently sucking until he stopped twitching.
I soon rejoined my SO who was still being licked and fingerblasted to oblivion, cumming constantly, mostly touching her and kissing her while gently playing with myself, still absolutely loving everything that was being done to her. Eventually she had her last orgasm and she laid there a shivering wreck.
**Winding Down (not really, this isn’t actually the end. Keep reading)**
The guy who’d been going down on my SO insisted on offering her a drink, and disappeared to the bar to get her a whiskey and coke. He came back up and we had a really good long chat and we soon decided to go to the jacuzzi to wind down. I was so thrilled by how confidently she de-towelled to get into the jacuzzi and she stroked my dick while we were in there, though I was thinking it was out of politeness rather than horniness. As it was closing time, I was extremely satisfied with the night and was content to just have a wank when I got home.
**The Fun Recommences**
Boy was it not just politeness. We drove home, chatting and laughing all the way and got straight into bed, ready to wind down and go to sleep, but we instantly started making out. My hand wandered down to her clit, which I treated very gently, though a little lube was much appreciated, and she started playing with me. I still thought she just felt obliged to get me off, so I’d have been happy to stop but she decided she wasn’t done with firsts tonight.
My SO doesn’t like the idea of anal. That’s fine by me, I’ve never enjoyed giving it myself (I enjoy receiving though), much preferring the feel of fucking a pussy, but I recently got into my head the idea of double-penetrating her – having me inside her pussy while another guy fucks her ass. I’d mentioned it to her quite recently, and had suggested a way for us to get into it. When I first received anal, I didn’t enjoy it, but when a guy once started playing with my dick while fucking me, I fell in love with it – having both stimulated was utterly ecstatic and I find it very hard not to cum very quickly in that situation. So I suggested that could I fuck her and, once she’d had an orgasm or two, I could put my teeniest butt plug inside her and carry on fucking her.
Well, tonight was the night. She said that she was still feeling really naughty and wanted to try it. So we eased our way into it and did exactly what we’d discussed and, I’ve got to say, she took it like an absolute champ. She got into it really quickly and I was teasing the plug out with each of my thrusts and slamming it back into her honestly quite hard and she said, although she couldn’t really feel it, as her pussy was feeling so intense, she loved it. We didn’t last much longer at this point, as it was ridiculous o’ clock in the morning and were quite happy to just finish up and pass out.
**Debriefing**
We discussed everything in the post-nut clarity, and we’re both eager to continue doing this, to try more things, continue going to the sex club when we can and uh, yeah, we answered our question – I’m pretty sure she can be completely assured that I am ok with her having a ladyboy hooker in Amsterdam.
Source: reddit.com/r/gonewildstories/comments/v0l9wr/me_and_my_so_group_popped_our_swinging_cherry_at