Development of any sex life is important to prevent it becoming predictable or even boring!! As some may know I like to try new things! On Saturday we discussed having triple anal sex again. We have ticked Triple Anal on our list so I suggested Quadruple Penetration. Obviously not Quadruple Anal because I would not think that possible. I went on to say I would like to try Double Anal, Vaginal and Oral. We have 3 males in our group so one of the girls will control the dildo in my pussy. We discussed bringing another male into our set up however decided against this.
You can of course go the route of adding more and more stuffing, sure, but you could aldo branch out into different (anal) areas.
As you said, ever more simultanious penetration will run into logistical problems. But you could go for depth play with long, flexible toys.
Another option is adding more mental aspects (as the brain is the biggest erogenous zone): Roleplay, BDSM elements or rituals, or perhaps challanges among your group.
Just as an example, challange Tiff to eat your ass as well as your boyfriend does. Put on a blindfold once she’s gotten good and try to tell the difference (though his beard might give him away 
).
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You’re 19, have sex with two extra couples and are already talking about the dreadfull “boredom” issue. Please be carefull with that, cause constantly searching for new kinks is an unstopable monster.
Sometimes, taking a step back is new. Don’t overdo it.
We are all close friends and keep an eye on each other to keep each other relatively grounded. I just love sex and anal / oral are my chosen vices! Yes I’m only 19 but have experienced more than most people will in their lives. That is my choice and I’m lucky to have friends who share my perversions!! If you were to meet me at university, you would think I was just like any other 19 year old and in a lot of ways I am.
We don’t really do a lot of BDSM stuff and nobody has mentioned it as a session. I like the idea of being tied up and blindfolded while the others are having a good session. The sounds would drive me wild, being left out. I bet boys would be giving a running commentary it to torture me lol and the girls would be so loud. When they let me out they better run like hell lol!
That’s exactly the mental kind of fun I mean. You don’t have to dress like stereotypical leather daddies and dominatrices, but instead see where your imagination takes you.
Then, you communicate with your partner(s), see what’s feasible and fun for everyone, and go to town.
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The other week we were at Karen and Corry’s house. I turned up in tracksuit bottoms and a Suicidal Tendencies T-shirt. I looked like a proper skanger. But a bit of make-up and a butt plug in my ass. All ready