For a little context, my boyfriend is in his early 20's and I'm early 30's. Despite the age difference, we've had a pretty solid relationship and been together for a few years now. We're best friends, do everything together, and talk about nearly everything. We're not currently living together, but want to in the future.
**How it started*\*
About 2 months ago, my boyfriend and I started talking about trying a 3rd or swinging after a big conversation. For himself, he's able to separate feelings of sexual desire from romance. And so he's always thought it would be nice to try things with various people he trusted, or involving his partner if he was in a relationship. He had casually asked me a little in the past when we'd be talking sex things we'd want to try, to which I said that it makes me uncomfortable and we'd drop it. The big conversation came about because a virgin friend was casually talking about how she's kinda horny and touch starved. He thought how it'd to nice to suggest her trying a few intro things us with, providing a safe space for her and it'd be fun for us. But he halted his thoughts because he knew I would be uncomfortable and didn't want me to force myself. Then he started feeling guilty and picking himself apart because he keeps having these thoughts/desires. He values our relationship above trying a new fun sex thing or this possible part of his sexuality, but worried about the possibility of his desires growing over time. He opened up to me finally after some prodding.
**My initial feelings*\*
I'm his first relationship. Other than a little bit of touching through clothes, I've been his only sexual partner. Hearing his desires and views on on sex with others made me feel a little like perhaps by being locked into a monogamous relationship with me, that I'm depriving him somehow. I have insecurity and anxiety issues. And so even if he didn't say this, my brain worried that this would lead to our relationship breaking over time if I didn't provide this. I agreed we could give it a try. To which he was still very worried about me, especially because I have a bit of trauma from a previous partner guilt tripping me when I said no to this very thing. I told reassured him that this was different because of my level of trust in him, how it was being approached, and that I could always find that I'm more ok with it than I think. Truthfully, I wasn't ok with it but my brain was panicking and also trying to convince myself. It seemed like a burden had been lifted from him and he was a little excited.
**Our first attempt*\*
During the next week, we talked a lot and very thoroughly about boundaries. He thinks he'd be comfortable with whatever as long as it's concentual and everyone is enjoying themselves. For me, I wasn't comfortable with any of this. But I suggested start with touching, maybe move up to toys. He discovered he didn't like the thought of a dick being inside me in any capacity, and so we agreed that dick/vagina insertion was off limits for both of us (happy he was fine without penetration on a girl, was a little confused why he didn't previously consider me with a guy). My mind was full of buzzing anxiety bees, which I expressed a little but tried to hide. We reached out to that one friend, but they politely declined. We then asked two close friends that are a couple, which is also experienced in swinging. It was agreed we'd start with touching and move forward from there. After the agreement, he asked me again if I was sure, to which I broke down crying for the next hour. Group stuff was never something I was comfortable with, but going from 0-100 in a week was too much for me.
**Battle plan*\*
We tabled for the time being for my well being. But through more talks, I found that this still seemed important for him to try. I suggested we give it another go, but laid down rules for starting very slowly. He said that it'd be difficult to not always hope for a little more than expected to happen, but my comfort was first. I started therapy with a relationship/sex thearapist, because I wanted someone to talk to about this but also wanted to tackle my poor self esteem and relationship insecurities that I've dealt with for years. I also started talking with the other couple a lot to learn about their experiences. We agreed cuddles would be the good place to start. Casual light cuddles are something we're both comfortable with our friends, but I wasn't used to seeing him like that with others in person. Then maybe parallel. We agreed to space out our experiences a little, it was ok for me to linger on a step or two, or place boundaries down as we go.
**Second "attempt"*\*
We hung out with the couple mentioned a few weeks later, let's call them M & T, with M being female and T being ftm transgender. I was asked how I'd feel about anything happening, we agreed cuddles would most likely be our limit. We already had a joking flirty relationship with several of our friends, and we went hard on that. Lots of appearance compliments, fun spanking as walking past, etc. I was a little taken aback when my bf ended up sitting between T's legs on the floor leaning back during most of the movie, because I'm not used to seeing that. They checked in on me a couple times, and I surprised myself by being able to confidently say I was perfectly ok with it. At one point after the movie, M & T made out for about a minute. My bf lightly initiated making out with me and although very shy, I was again surprised how ok I was with it. Though clothes, I was also ok with his hand on my breast in front of others. Things calmed down and we returned to watching shows. M fell asleep, T and I cuddled on either side of my bf. T had showed off a trackwheel toy for fun earlier because they had just bought it for M, and it was funny cause I had just bought the same that week for us. While watching tv and T/ I cuddling my bf , T got out the track wheel and just absent mindedly moved it up/down on my bf's arm. I at first experienced a tinge of jealousy, but was able to successfully distract myself by using my own wheel on my bf's leg. I think it ws helped the fact that he held me close to him, the wheel thing was so small, and that it was done absent mindedly like. I had no issue with my bf getting a hard on, but it was odd knowing that others could see it too (afterall, it's usually a private thing). After M/T left, my bf and I went to the room and had very loving sex. Overall, I had a good night. I got to see good friends. I was proud of myself and was surprised to find that I might be perfectly fine with ast elast same room parallel play. I also felt so reassured by how non-pressure everything was and how people checked on me regularly.
**Going forward*\*
So it's been almost 1.5 months since. My bf and I's communication has leveled up. He's learned to handle his spiraling negative thoughts about himself better and to handle patience more. And I've learned to be more bluntly honest with my feelings and where I'm at with things. He initiated an apology a few weeks back after seeing some negative experiences that redditors had after their partner suggested group stuff. He said although he's excited to try things at a slow pace, he wants things to be at least a little enjoyable for me and to let him know if I'm not at any time. He also apologized for his negative spiraling thoughts about his own self worth as a partner in the beginning inadvertently making me feel pressured. It was a really good moment for us with lots of love expressed. We've since agreed that the next time we try things, that we'd be up for same room parallel play.
**Why I need you guys*\*
But although I had a positive first time and we've had great communication no pressure since, I can feel that blanket of anxiety sweeping over me again. My brain can't help but think about the things beyond parallel. We agreed full on sex is a big no, and he seemed open to oral sex and kissing also being off the table. Which would leave hands, toys, mouth on non-genitalia body parts. We're not even there and will probably stay on parallel for a bit, but my brain keeps thinking about the steps that come after. My bf has no interest in dating anyone else, this is something he wants to do with me. Plus the other couple is solid with each other too. But I still have insecurities like he's going to be disatisfied with where my final boundry is when we hit it, that he'll end up wanting this way more often than me, that I'll eventually bore him, that somehow he'll be taken away from me, etc. Things where he's reassured me a thousand times and I honestly don't know how much more supportive/reassuring he could be to help.
How can I keep my brain from thinking like a slippery slope and getting too far ahead of itself? How can I soothe my anxiety/insecurity that clearly stems from my poor self esteem?