Straight Trippin: My First Psychedelic Trip

I tried mushrooms for the first time about a month ago. I don’t have any prior experience with psychedelics up until now, but I’ve been intrigued especially after reading posts like this one. I guess you could say I’m searching for something. I’m seeking ways to help expand my mind. I can be a stubborn one. I’m halfway through reading How to Change Your Mind by Michael Pollan. Let’s just say curiosity got the best of me, and I wanted to see for myself. The other reason my curiosity got the best of me is because I’m doing some hypnosis work. I want to see if psychedelics have any effect on my hypnosis sessions.

It was a Saturday morning, and I had the day to myself. I made my usual oatmeal with peanut butter, cinnamon, and hemp seeds, and I sprinkled 1g of mushrooms on top. I lined up some ginger tea just in case any nausea crept up on me. I can’t say I had any intentions set, but I was just looking to see if anything happened. After about an hour I still didn’t feel anything so I went outside. I did notice my senses heightened, especially my hearing. I could hear all the birds chirping more pronounced than usual. The spokes of bicycles passing by was distinct. I could hear the train chugging past me. As far as visuals go, the color red was very bright. After a 30 minute walk, I went back inside. It seemed that would be all at 1g for me. But it was a good first test.

I started looking into getting a trip guide, but I knew it would take me a long time. I’ll say that it takes a long time for me to forge relationships with people, but when I do they are solid. I settled for telling someone I already have a good relationship with that has some experience with psychedelics. Unfortunately this person is half way across the world so we agreed I’d text her once I took the shrooms, and she checked up on me periodically to see how I was doing. If it is your first time, a trip guide/sitter is definitely recommended. I will say even before I tell my story, I think I would’ve been able to trust and let go a bit more if I had a guide.

I woke up early last Friday morning and cleaned up my place. There’s an emphasis on Set and Setting in the psychedelic community. Set being the mindset during the trip. Setting being the physical environment and space for the session. So for setting, I cleaned up, positioned the one piece of art work I own, let some light through my ceiling to floor windows, and put on my Calm Whale playlist. As far as my mindset, I didn’t really have any intention for the trip. I just wanted to see where my mind took me. I did have some questions from my hypnosis coaching group handy just in case. Something along the lines of, “What kind of man do I want to become?” “What’s stopping me?” “How will I know I’m making progress?”

At 10am I measured out 3g of mushrooms, crushed them up and sprinkled it over my peanut butter/cinnamon oatmeal. I made a cup of ginger tea, again, just in case I experienced any nausea. At 10:48am my throat started getting phlegmy and I started feeling sleepy. At 11:15am I tried to go outside, but didn’t make it past the door. I started feeling wobbly and drowsier. I decided to write the last words in my journal before I started tripping. As I wrote the page got brighter, and when I closed my eyes I could see what looked like jellyfish. I grabbed the blind fold that I usually use for my lovers, and started to drift off.

Once I had the blind fold on the patterns got bigger. Sometimes the patterns would change to the rhythm of the music. I don’t know what this means but I saw eyes looking at me. The other peculiar image that I saw was myself, a woman who’s face I could not make out, and what I’m guessing was our baby. I don’t know who the woman was, and I couldn’t tell if it was Midwest or not. Other than that I just saw lots of patterns. If I started to see something that looked like it might be scary, I’d open my eyes.

It felt like waves of drunkenness. When I started feeling drowsy I’d close my eyes to see what the psilocybin was trying to show me. I tried venturing outside a few times, but I was afraid I’d catch a wave and I wouldn’t be ready for it. I went from smiling to tearing up for no reason. The patterns in the tiles moved and danced like I was in an animation. I have one painting in my place that Midwest painted recently. I spent about 30 minutes deciphering it as its shape shifted like clouds in the sky.

After about 3 hours of an intense experience, the psilocybin was letting up and hunger kicked in. I went to the grocery store to pick up a few items and to take in this heightened experience. For some reason I get approached a lot, and today was no different. I ran into this older lady, beautiful I might add, and she spoke to me like she knew me. Like I was her son. I ended up asking her for help because my hands were too dry to open the produce plastic bags, and I stood there for about 5 minutes intently trying to find the opening. We had a good laugh as she teased me. I felt so close to her even though we had never met until then. Then I went for a late lunch. On my way back I was overcome with an ineffable joy. I was grinning from ear to ear. I have no other way to explain it. It was like a sudden wave of gratitude and an overall appreciation for where I am on my trip, where I am in my life.

This was my first trip.

Eyes Bigger Than My Stomach

Midwest did the deed. She slept with the guy she was seeing. This happened right before she went out of town. She didn’t tell me until she got back, and we were in person. While she was away, I got up to my own trouble. I went on three dates. I managed to pull one back to my place the same night I met her, but I couldn’t pull the trigger.

I met her, Med-School, on a rainy evening in a restaurant. Right away I noticed she was a quirky girl. I guess it’s true, I’m attracting my “image match.” She’s a talkative one, but good. Less I have to say. We kept the conversation pretty light as the tables were close to other patrons, and I felt it would be weird trying to have intimate conversation with her. We were able to keep up the small talk, and I think that the fact we both spoke Spanish was the thing that kept the vibes flowing. She said I reminded her of a good time in her life, and kept raving about my Spanish. I always question whether I should show this side of me. For some girls, it’s a big turn on. For others, that grew up speaking the language in question it can be a turn off. They think I’m trying too hard to impress them. It’s something I’ve mainly done for myself, but I get it.

After we finished up at the restaurant, I invited her back to my place for another drink. As we wait for the wine to chill, the conversation is still pretty innocent, but I can feel underneath her thighs getting warmer and warmer as I press my leg up against her. Then we finally broach the topic of drugs. She says she’s only ever tried weed and the occasional cigarette, but thinks she wants to try Molly. She thinks it fits her personality. I agree. That somehow led to the topic of dancing. I took her for a spin, and while we were close I just leaned in at some point and kissed her. She doesn’t have much lip to kiss, so it feels a bit awkward for me. She is enjoying herself though.

We start stripping, but I can’t tell that I’m getting aroused in anyway. I tell her this is normal for first encounters where I’m in my head and that it’s OK. We can just explore each other’s body. I can’t say I was into her body much. Small breasts, and chubby waists. Some girls surprise me when they take their close off (even Midwest), but this experience was mainly underwhelming. I’ve done better. I should be doing better. There was also a faint scent of cigarette. Initially it mixed in with her perfume, so I couldn’t tell but it became more apparent that it was cigarette smoke as the night went on. I couldn’t get it up. I let her stay until the next morning, but I still couldn’t do anything. She gave me head as a last resort, and then she left. We both agreed there was no chemistry, and there was no reason to see each other again.

Now back to Midwest. When she told me she slept with the guy, I had no reaction. I kind of expected it. She said it wasn’t about the guy, she just wanted to see if she could do it. Well, she did. The weirder thing for me was that she was more lovey-dovey than usual. She wanted to spend more time with me, etc. She also said she wasn’t going to see the guy again. She said she would only explore with someone else if there was an undeniable chemistry, instead of seeking it out. I like that idea, but I was still very much in hunting mode, so I continued to look around. I had another date. I knew immediately I wasn’t into her, and I dragged out the date even though I knew I wasn’t into her at all. I think she could feel that, and ended up calling me out on it. Midwest called later that night to see how things went. I told her that I’m not going to see this person again, but for whatever reason she started crying. She said she doesn’t want to do this (open relationship) anymore. As things were pretty heavy, and I was ready to admit I didn’t know what I was doing, I agreed to close things off. More than anything, my brain hurt.

I realized I’m trying to do too much, and too soon. My eyes are bigger than my stomach. I’ve always been told that. I was trying to bulldoze my way through, but I’m not there yet. While I’ve definitely made progress within the last year, there’s still a big gap between where I am and where I want to be or where I think I should be. That’s OK. It’s time to pause and reassess where I’m going and what I want. Midwest is now saying that she wants a family. And with me, at that. We have spoken about it a bit… I think about it. I’m coming up on my mid 30s, so I still have time. I’m in no rush. When I’m with her I can see it, but as soon as I’m around other women I can feel that pull, that desire to flex my skills to see if I can make something happen. The pull feels more pronounced since we’ve closed things off. And while I can see it with her, I don’t know if it’s right, or if it’s the right time or how to properly assess a woman (This probably means I should hold my horses). She’s also recently saying she wants to travel until the end of the year, so I’m not sure how that would even work. I’ll join her for 1 or 2 months, but after that if she decides she’s going solo I’m not so sure how things will end up. Initially I balked at the idea of her traveling solo, but I’m going to take the time to work on my body and mind. I’ll have a lot more time, now that I’m not on the hunt. I’ll continue to train hard, and I think I might’ve found someone who can help me with improving my mindset. I’m going to give it a shot. At this point, that’s the main thing holding me back. I have nothing to lose, and lots to learn. Despite a couple rough months, we’re still having fun. I’m willing to let this play out and see where things go, given we slow allll the way down and just enjoy the moment.

I’m pumping the brakes for now, but thanks to everyone that gave me advice on this. Sometimes I try things the hardest way, even when there are better ways. If you can, and you understand where you are, choose the way that’s better for you. I’ve been pushing the limit to see where my boundaries are, since I’m not quite sure exactly where they are in practice.

A Frayed Connection

The cost of opening our connection for my freedom was bursting our love bubble. I went back and forth on the decision to remain open so many times that I lost Midwest’s trust. She couldn’t take the push/pull. One moment, pulling her in close to me. The next, pushing her into a den of hungry wolves. In the end, she decided to stay in the den of hungry wolves. She told me it was the den or nothing. I will have to earn her trust again, if that’s even possible. There’s a look that women give when they no longer trust you, and even the way they treat you is different. Maybe I’m dumb, but I’m going to ride it out. I decided to join her. Not because I’m afraid to start over, but mainly because I’m not ready to give up on our connection just yet.

When I met Midwest I knew we were in a similar place, but we were probably talking past each other. I remember us both dancing around the, “So, what are you looking for?” question in my kitchen on our 4th date. And her blurting out, “If you want something casual, just tell me.” But also blurting out that she likes me that same night. I kept quiet. I was never really good at setting up casual. At the same time I hadn’t been anyone’s boyfriend since my late ex-wife. I wanted something in between, or what I would call a lover, but didn’t quite know how to phrase it or how to give off that vibe. I went into proper boyfriend mode, and didn’t even realize it.

Midwest is awesome. I don’t think I’ve ever had a girl that was so into me, or at least pretended to be. She took most of what I said as fact. When I give her tips about things I’m good at, she actually takes them into account and uses them. She wanted me to lead her, and I did a poor job. Initially, she was doing this for me. She thought she had to do this to win me, and I can only imagine that’s why she was pissed when she realized I was a novice in the game. Part of me says I should have stopped all of the “open” talks as soon as I realized this was something more than sex for me. It’s not everyday I find a person that I want to be around as much as her. The other part of me says she was curious and wanted this anyway.

Either way, it was a mess. Not smooth at all. I lacked a lot of composure during the last few weeks and my inexperience showed. I should have asked for help/advice. I appreciate Nash’s comments. There’s no turning back with Midwest at this point. I’m not going to sever our connection, but I can tone down how much I tell her, and try to get the focus back on me and her. I don’t think all is lost, just yet. When it fades out, I’ll most likely leave what didn’t serve me from the whole “open” concept behind for the most part. As for new connections, I’ll have to tighten things up and stop spilling my guts. I’m not giving up though. Not yet.

Feeling Free

It’s getting warmer. The days are getting longer. We’re all getting antsier by the day. Before last week, even though we had opened up our relationship in February, we did the opposite of see other people. We saw more of each other. I was enjoying it. Apparently it has been eating away at Midwest, because she’s been trying to mentally prepare herself for what our new relationship would look like. Two weeks ago, she asked me again if we were still doing this. I almost backed out. I told her, “Things are good the way they are. Let’s keep doing this.” She immediately rolled her eyes. She actually told me, “No, you’ve been pushing for this for so long now I feel like we have to go through with it.” I get that at this point I’m coming off as indecisive. I didn’t know it bothered her so much though. I was having a good time, just the two of us. I tell her, “Fine, let’s follow through on this.”

The next day, I pinged Yams and Thai Smile. Funny enough, on two separate occasions they both contacted me out of the blue a while back, but I wasn’t trying to make anything happen. I couldn’t get Thai Smile out. She still feels very receptive via text though, so I’ll keep her on my radar. Yams responded immediately. We set something up for the weekend. I told Midwest I was going to see Yams. It felt kind of weird telling her, but at the same time liberating. I wasn’t sneaking around or hiding anything, yet I was free to seek another potential lover. I’m freeee!! Yeah, that’s what I felt. Seeing Yams was good, except there wasn’t anything there. We felt like two friends catching up, which we are. But nothing more. I ended up telling her about Midwest, and she told me about her guy, who she was probably seeing the first and last time we fucked. We’ll definitely keep in touch though. Midwest left for the weekend, and when she got back in town I gave her the rundown. Mainly just for reassurance. Nothing happened.

I also had to get back on the apps, of course. I immediately got good response this time. 15 decent looking matches in a week is good, for me at least. At this point, I told three women I was only interested in open relationships. One took the bait. I didn’t like her look or her personality once we met in real life, so I enjoyed a drink with her and let her go. Maybe when I have more experience and balls, I’ll be able to leave if I’m not feeling it. I knew immediately I wasn’t into her. Damn photo filters are deceiving! I’ve since tried a combination of putting “ENM” (ethically non-monogamous) on my profile and just disclosing before inviting them out. If I disclose on my profile, I’m not going to get any matches. If I don’t I can at least chat a bit to warm them up before telling them. It definitely slims down the opportunities, but being direct and transparent feels good. No one has responded negatively, even if they’re not into it. I tried this based on xbtusd’s post on The Red Quest’s blog on setting the frame from the beginning of the interaction/relationship. Just reading reddit posts, this seems to be the norm in the ENM community.

The next day, Midwest tells me she’s meeting up with someone. I don’t know what to think, but I tell her to have fun. I didn’t hear from her that night. By the next morning I was pissing my pants, but trying to play it cool at the same time. Did she fuck someone already? She said she didn’t want to go on the apps, so she reached into her rolodex of backups, and voila! A dick on demand. She seemed hesitant to tell me about what went on that night, especially since she could hear the jealousy in my voice. I knew this was going to be hard for me, and easy for her. I just didn’t expect everything to happen so fast. Apparently, they didn’t have sex, but they fooled around, of course. She wants to see him again. I spent the weekend going back and forth. Do I tell her to keep going or to stop and close things off?

We spoke again a few days later, and I told her I didn’t want her to see him again. I wanted her to be exclusive to me. Dickhead move, I know. I probed a little bit more, and she gave me more details. I felt relieved, but at the same time I didn’t like how I felt last week when I knew she was out with another guy. I was on edge. I couldn’t sleep. She didn’t give me much fight about closing things off, but she was annoyed again by my indecisiveness. I felt weak for going back on my word, too. So I told her if she feels like seeing him again, then go ahead. That night was weird. I went from jealous to horny. When I spoke to her the next day, it sounded like the same happened to her. Or rather, she was just hornier. We fucked like rabbits that night, and the next morning. I made sure she got every drop of my juice. Then I told her to go see her new friend if she wanted to. I don’t understand the psychology of what just happened over the past couple of days, but it was wild. I wonder how I’ll react after I hear what naughty things they do next.

I’ve come to accept that it’s going to be way harder for me to get something going. Midwest even told me it was hard hearing me go on dates without her, but once she went on one it didn’t really bother her. Especially since her date was more eventful than the two that I had. She’s more worried that when I do find other lovers, they will be more long term situations, and it will take away from her being my favorite girl. I doubt it, even if they’re hotter… but who knows. I think she’s also getting to know a side of herself that she didn’t know existed, or didn’t want to admit exists. I know she wanted this though. She was just waiting for someone to make it happen. I think she’s going to continue seeing him, so I’m going to face my fears. I decided I’m going to try my best not to worry about it. I’m selling our exploration into non-monogamy as a growth opportunity for both of us. I’ll use the pent up tension to continue working on my goals, and to hunt for new lovers. I’m free.

Goals 2021

  1. Train
  2. Read
  3. Approach Putting myself out there
  4. Level Up at Work


My main goal is still training. Last year went very well. I think it’s safe to say I’m not skinny anymore. I didn’t put on any weight, but I have more muscle mass and definition in my upper body. I probably did lose weight since my legs shrunk a bit though. I also eat at maintenance. I either meal prep or months I don’t feel like cooking/tired of my cooking I order prepped meals. I don’t calorie-count. I just listen to my body. If I’m still hungry I devour every banana/nut/prune in my kitchen. You can put on muscle without bulking. I train hard and rest hard.

  • No cardio has helped massively. My body is finally starting to hold on to the muscle and I’m getting stronger. Lucky for me, before the pandemic happened I was mainly doing calisthenics and I had everything I needed for my home gym. Current workout looks as follows:
MondayUpper Body
Warm up 30 min (Stretching/Band work for Upper & Lower)
Skill Training – 5 Planche push ups
3 Planche leans
Front Lever Training

Weighted Ring Dips 4×4 +45lb. plate (3 min. rest between sets)
Weighted Chin Ups 4×4 +45lb. plate
Back to wall handstand pushups 4×3 with Elevated Pike push ups to failure
Horizontal Body weight rows 4×10 (weighted vest sometimes)

TuesdayCore + Legs
Hanging Crunches 5×20 (Superset)
L-sit crunches on Rings 5×10 (Superset)
Front lever Advanced tuck hold 5x10sec (Superset)
Lying Hip Extensions 2×10
Knee Strengthening Routine
ThursdayCore + Legs
Hanging Crunches 5×20 (Superset)
L-sit crunches on Rings 5×10 (Superset)
Front lever Advanced tuck hold 5x10sec (Superset)
Lying Hip Extensions 2×10
Knee Strengthening Routine
FridayUpper Body
Warm up 30 min (Stretching/Band work for Upper & Lower)
Skill Training – 5 Planche push ups
3 Planche leans
Front Lever Training

Weighted Ring Dips 4×4 +45lb. plate (3 min. rest between sets)
Weighted Pull Ups 4×4 +45lb. plate
Back to wall handstand pushups 4×3 with Elevated Pike push ups to failure
Horizontal Body weight rows 4×10 (weighted vest sometimes)

This is the most exciting part of my day. If I can do this, the rest of my day is a piece of cake, even if it’s not. Since I’ve added the 45 lb plates, I’ve skipped a few Tuesday’s or Thursday’s. The extra weight definitely puts a toll on the central nervous system. Some days I’m wiped. I get the same feeling sometimes when I haven’t done heavy deadlifts or squats in a while. しんどい。Last year I did the same routine without the extra weight.

The knee strengthening routine is there because between pistol squats and trying to get into lotus pose, I tore something in my knee last year and it’s been bothering me lately after taking a battering from the waves at the beach. I’m ready to get back in the gym though. Doing bodyweight exercises is fine for upper body, but I’m not keen on doing hundreds of squats. I’m going to check out my old gym to get back to dead lifting and squatting soon.

As for skills, I’m slowly working on front lever, planche, and handstand. I say slowly, because these can cause joint and connective tissue pain or other injury if you progress too fast. I have a decent handstand (10 sec), so I’ve been working on trying to do the same on parallettes. I think my favorite thing about calisthenics is the progression. Every movement can be made easier/harder by changing the lever. A reasonable goal of mine is to be able to do at least 3 full chest-to-wall handstand push ups by late summer. How am I going to get there? Progressions. I started off doing push-ups, then decline push-ups. When those got easy, and I wanted more pain I started doing pike push ups. Want more pain? Elevated pike push ups. Even more? I recently started doing half-reps of back-to-wall pushups and then elevated pike push ups to failure. I’m breaking down the movements until I’m strong enough to do the hard/cool looking ones.


In 2020, I read a shit ton for me. I still have a lot of new books that I haven’t read on my new bookshelf. So keepin on.

Last year I read:

– No More Mr. Nice Guy
– The Red Queen
– Mating in Captivity
– State of Affairs
– More Than Two
– Cheap Sex
– Sperm Wars
– Intimate Communion
– The Essential Guide to Neuro Linguistic Programming
– The Simple Path to Wealth

Now on my plate:

The Revolt of the Public
Clean Energy reading

It’s a lot, but I’m playing catch up. Who knows how much I’m retaining, but I’m getting exposed to the words and ideas so maybe something will stick.

Putting myself out there

The approach goal is gone. I can count on one hand the times I tried to approach last year. I’ll resurface it if things change, but my energy can be better used elsewhere for the time being. If there’s a cutie at the supermarket, I’ll definitely give her a smile with my eyes and invite her too cook a meal with the ingredients in her cart. Other than that, I’m good.

A theme that has kept coming up for me is trying to find somewhere I belong. I need to double down here. Being a lone wolf is cool, but it will only take me so far. So I’m trying to get involved in different things.

Last summer, I started Muay Thai. I did this, yes, to learn how to fight, but also to see if I meet some cool guys. I was consistently going twice a week up until the holidays. I’ve been traveling a bit, so I haven’t been back since. We only did bag work, but it would be cool to do some sparring. I haven’t been in a fight since I was 9 years old, so I’m likely to shed a tear after getting kneed in the abs or boxed in the face.

I’m also about to start a motorcycle class. A fun idea of Midwest’s. Now I’m actually thinking of going all in and getting a used bike to ride this summer once I pass the exam. I’m considering a 300cc bike. I wanted to go electric, but I think the torque on those will fling me into oblivion with a simple flick of the wrist. I went shopping for gear the other day, and the sales rep was telling me about the biker community. I’m down to check it out.

I also signed up for a few business organization memberships recently. I’m just trying to get involved any way I can and see what sticks.

I also reluctantly got on IG.


Work is still last. I took advantage of some good opportunities and got some visibility here. I made a mind map of a potential path I could take, but I don’t know if I want to follow through other than the fact that I don’t know what else I’d be open to doing. Work is funding my personal exploration though, so I trod on.


A Ramble about the Scene

I remember the first time I went to a salsa club as an adult like it was yesterday. I was excited. I had been practicing my basic with some Youtube videos, and tired of dancing by myself I decided the only way to learn any more, I’d have to go step on someone’s toes. Why salsa? I’ve had a love affair with salsa that goes way back. It kept popping up in my life during my travels as teenager. I had never danced it before then, but the bassy notes still get me every time. Why dance? At that point, I had been separated from my ex for a while, and I was ready to get close to somebody. I didn’t know how to go about it any other way.

So I go out for the first time. I take a lesson, and afterward I remember standing by myself, moving to the music. Then an older lady comes up to me, and she asks me with a grimace, “Do you know how to dance?” I tell her no, but I’m learning. She gives me a look, and walks away before I can come up something to say. I stayed for a while. I might’ve danced with a few people but the first old lady really killed my vibe. After that, I went back to practice mode. I went into monk mode for another month before I went out again.

I pushed myself to go out again to another venue. Another fun lesson, but when the music started, I went to an empty part of the room and started moving by myself. Another old lady sees me, and approaches me. She says, “You look like you want to dance.” I probably told her something like, “Yea, but I can’t.” Instead of making a mean face like the first old lady, she hands me a flyer for a weekly salsa event. I attend the event the next week. The instructor announces he has a team, and everyone is welcome to try-out. Then and there I decide I want to be good. Shit. I have to be good if anyone’s going to take another look at me. I sign up.

I learn by doing and repeating until I can do something well. So this worked better for me than taking a bunch of random lessons where you do a different routine every time. We worked on a routine for four months with the same people. By the end I had a partner. We were all working together to not look like total noobs by the performance date. Right before our first performance, I really found my groove and everything, movement-wise started clicking for me. Let’s just say, my partner and I were put up frontman/woman of the show.

I’m going to stop the story there for now. But I did that for a couple of years with mainly the same people. We got over our fear of being on stage together, we traveled together, we ate together, we partied together, we did a lot together. I still compartmentalized that part of my life from everything else. Dancing was light, and it was fun. I’m light and fun when I’m dancing. My life outside of dance at the time wasn’t. At least I thought so. I didn’t want to bring the heaviness of my life into the group. I assumed people wouldn’t want me around if they felt my heaviness, and my thirst. If I had game, it might not have been a problem. Without game, you just come off as a creep. I was trying to avoid that at all cost. Lots of guys were getting called out for harassment at the time, even “top guys” in the community. There was also so much that I was blind to; I was clueless and too nice to go for what I wanted, and in a cool way. Girls told me they didn’t date/sex or whatever with people they dance with. I thought it would be the same if I tried to join other circles. Now that I look back, I just wasn’t as cool as I thought I was. Girls don’t say stuff like that to the cool guys in the group. I didn’t see guys struggling to get girls, but I also didn’t see how they got girls (if they did), so I was afraid to ask. I was afraid to look dumb. Hell, other people thought I got girls, and I played along. Only thing is I knew it wasn’t true. I still wasn’t ready to be honest with myself about where I was vs. where I wanted to be. If I couldn’t be honest with myself, there’s no way I’d be ready to initiate the honest conversations I wanted to have.

Things Open Up

It’s been a while since I’ve written anything here. I’ve had a lot of thoughts, but no real desire to write them down. Also, I think since things have been moving a lot slower I’ve been waiting to see how things pan out before I speak too soon. I’m still seeing Midwest. I’m surprised myself. This is longest I’ve seen anyone since I was married.

In my last post, I wrote about how I emailed her and told her about my interest in exploring non-monogamy. Since then, she’s brought it up a few times but I kept the conversations general and not about us. Mainly because I didn’t know what to say. That’s until I read Breeze’s post where he mentions Blackdragon’s Ultimate Open Relationship Manual. I bought the manual that same night. Blackdragon outlines a nice framework to set things up.

Very early into meeting meeting Midwest we foresaw the winter months being tough, and started talking about a trip to somewhere warm to escape the deep freeze. I’m sure most would not agree with taking this trip with someone you barely know, but I’m living my life. We spent two weeks being lazy beach bums together, and I only speak for myself here, but I enjoyed every moment.

Not even half way through the trip Midwest wanted clarity on what we were doing. My initial plan was to save this conversation until after we returned, but I had also already told her what my stance was, so I figured what did I have to lose? So I told her. Taking a few notes out of Blackdragon’s manual I told her something along the lines of “I really like you, but I don’t see myself being monogamous long term.” I told her I’d let her process it and she could get back to me when she was ready. It was not as short, and not as smooth but I verbally told her. As we walked back to the place we were staying, I can’t really tell what she was thinking. I could only sense that she was feeling heavy, and I gave her space to be by herself for a bit. I was nervous. I didn’t know if she was going to react negatively, and then the rest of the trip would be spoiled or what. An hour later she came back to the room, showered, and I rubbed her sunburned body down. Then we did what lovers do. I figured I was in the clear. She seemed to have had returned to her jovial self.

Two days later, we’re sitting at lunch, and she follows up. She’s down to explore non-monogamy with me. In the back of my head I’m dancing because I can’t believe this is real. To anyone who experiences this on the regular, this is child’s play. To me though, I feel like I’m unlocking new a new level… like I’m entering a new world. I can’t believe this shit works. In that moment I realized I didn’t have to be exclusive with her to get to this point, but I needed better frame from the beginning. This experience helped me recognize that. This experience broadened my map of what is possible.

She wanted to know what non-monogamy would like for us. I postponed that conversation for when we returned so that we could just focus on where we were at the moment. One of the things she’s worried about is what her friends and family would think. My initial thought is to tell them, “you’re dating” as a somewhat discreet response. Do you give your girls a script or do you leave this entirely up to them?

We’ve since had a conversation about what our open relationship will look like, but ultimately I think we’ll have to figure this out as we go. Funny enough I haven’t had the desire to see anyone else or open up the can of worms online, but maybe that will change as things warm up.

Poco a Poco

The last couple weeks have been interesting. A few weeks ago Midwest and I decided not to use condoms. Or rather, our bodies decided for us. I don’t know what it is about her, but very early on I was curious to feel her skin against mine. I generally always use them, but I was noticing that especially during initial encounters I’d always get a little soft when I reach for the condom. This is the first time I actively pursued not using one with someone I’ve just started seeing. I think partly because I might have been a little worried about getting soft, but mainly because it just felt right. We briefly touched on both having been tested, but I find it difficult to for it to hold any weight. We’ve both been out here in these streets. I took the plunge anyway. Damn, it feels good to shoot my load inside of her again and again.

I think we both had our concerns. Mine were mainly around if her birth control really works, and hers were more if I habitually have unprotected sex. One thing that stood out from one of our conversations is that she said she wanted me to be honest with her, even if she didn’t like what I had to say. Up until now we had both been dancing around different what we’re doing and so on, and I can’t help but think that she’s only mimicking the behavior I’m displaying towards her. I’ve been battling with this before I met Midwest. To be upfront and honest, or to be vague and “mysterious” with my intentions. I think I have scared girls away with being too honest in the past. So I’ve definitely been doing more of the latter, but I’m not sure that works for me. Just like I found out this year being super gamey doesn’t really work for me. Especially because for whatever reason a lot girls either automatically think I’m a player or that I’m married, or worst case scenario, that I’m some weirdo. It might work for short term success, but I don’t know if it will work for the girls I want to keep in my life. The funny thing is right before we had this conversation I was reading Honesty is an Ideal, and other good posts on Kill Your Inner Loser. These posts helped push me in the direction of honesty.

Since Midwest and I were already broaching certain topics I decided it was time to tell her. In my last post we decided to see each other exclusively and then I turned around and tried to awkwardly and vaguely tell her that we should keep the relationship open. When it comes to vulnerable topics especially, all of my smoothness goes out the window. I’m stuttering and choking on my words, and this doesn’t really help sell the idea. So I decided to write her and tell her the truth, my truth. Without getting into too much detail, I finally told her that I was interested in exploring non-monogamy and that I was scared of how she’d react had I told her earlier. I was actually surprised by her reaction, but that could also be because it’s not fully real at the moment. She’s open to having that conversation if/when the time comes, she says. Maybe it will be something we explore together. The main thing is, now she knows. It’s no longer a weird conversation we have to dance around, and I can gradually keep bringing it up, if I choose to.

I think this is a good step for me. It’s taken many iterations to make one step, and will take many more. I’ve come from sporadic casual encounters, to getting consistent dates, to now seeing one person consistently, and being able to share with that person that I at least want to explore non-monogamy. It wasn’t easy for me to say the first time, and I’m sure I might stumble over the conversation again. The main thing is the conversation is out in the air. Exploring exclusively with Midwest is giving me a lot of insight that I’ve not been able to get with the short, casual relationships I’ve had in the past. It’s also laying groundwork for the self-reflection and the internal work I think I’d need to do to create the type of non-monogamous lifestyle I might like to have in the future.

New Territory

It’s been an interesting couple of weeks with Midwest. Last week I decided to see Midwest exclusively, and I dropped my other lead Thai Smile. Thai Smile seemed enthusiastic about me, and even though I found her physically attractive, something else was off for me. Can’t quite put a finger on it. Or it could simply be that I just wasn’t into her that much.

From around our third date almost a month ago, Midwest has been pushing for exclusivity. I was hesitant, but I gave in last week. I was already contemplating dropping everything and taking a break if nothing worked out because all of my experiences were basically hit and runs. We had what I would consider a really good session, and in my fuzzy minded state I told her I wanted to be exclusive. It is what I want right now, but I probably could have danced around the topic a little longer.

I have my reasons why I made that decision. One is that I decided that if nothing worked out I’d keep my head down and focus on my fitness and career goals. I’m making good progress and want to continue following through to see more substantial progress. Especially from a physical aspect I am transforming and the ladies have been noticing. The fewer distractions the better. Two is that nothing else has been consistent. Sexually speaking, it’s difficult for me to learn much when I’m changing women so often then going in long periods of drought. Every women is different, and if I’m not seeing any one of them consistently I’m not getting much from the surface interactions. Or maybe I need to learn faster. Three, I genuinely enjoy Midwest’s company whether we’re having sex or not. That’s enough for me to keep her around. I don’t feel drained when I’m around her.

A couple days after I told her I wanted to seal the deal, I got cold feet. We didn’t really have a conversation about what our exclusivity meant and I definitely wasn’t trying to be put in the Mr. Serious Boyfriend category. I called her and clarified. I told her I like her, and I like exploring with her but marriage is not in the cards for me in the near future. (She recently threw the marriage thing at me one night during one of our conversations, and she’s running out of time.) I weakly suggested that if she was still exploring sexually or that marriage was something she’s looking for that we keep things open. I could hear the frustration in her voice turn into tears. I don’t know why, but I felt shitty in the moment. She told me she felt that I was backing out, but instead of saying so I was trying to put the pressure on her. I’m fine with my decision. If things don’t work out I can always restart the pipeline. I think she doesn’t want to deal with the fact that I’m putting the truth in her face.

Fast forward to today. We spend the day together and have another good time even though we’re both exhausted from our long weeks. Initially she touches on how I made her feel when I called her and suggested an open relationship and how she doesn’t like how I’m already doubting us, and blah blah blah. I somehow reassure her and everyone’s happy again. Later on we’re talking about how our relationship with sex has evolved over the years. She shares that only recently she’s entered an exploratory phase and how she’s learned the most about her sexuality with casual sex. She says that casual sex has given her the freedom to be selfish and to get pleasure on her terms. In contrast, in a relationship she has to think about the other person’s needs and she tends to try not to be as selfish. Going off on a tangent, but to my note above… as a good looking guy casual sex has not offered the same eye opening revelations about my sexuality. Casual sex makes me feel disposable, and I feel like I’m being thrown away most of the time. If my first performance is poor, I generally count on not seeing/hearing from the chick again unless for some other reason she really likes me and/or has no better options.

Later on in the conversation I ask her what she wants out of a relationship. We’ve had this conversation before but we were dancing around the truth, or more than truth, the realness. This time one of the things she said sounded an alarm. She said she wanted a “safe space” in a relationship. I’ve been reading a lot of Esther Perel lately and I think one of the questions she asks is, “Can desire be ignited/maintained in a safe space?” I ask Midwest this. She knows where I’m going with this. I then ask her, “where would you go to be sexual if you didn’t feel fully comfortable expressing your sexuality within that safe space?” We start discussing the pros and cons of monogamy vs. keeping things open. For her and I’d say for me too, a pro of monogamy is knowing or thinking that you are only having sex with each other. A con being once this “safe space” develops and extinguishes the flames, we either treat each other like roommates or we move on to greener pastures. She actually started listening to me, and asking me what an open relationship might look like between us.

This was enlightening because I’m seeing for myself how women play both mating strategies. Midwest basically told me that she’s been keeping things casual until they’re not. In my head that means she still wants to explore, but she’s in conflict with herself because she’s also thinking about the fact that the clock is ticking for her if she wants a family.

She wants to table the open discussion for now. We both decided we don’t want to share. I could tell she was feeling heavy about all of this. I did make sure to nip it in the bud that before anything else, we are lovers. At first I felt bad for bringing it up… now, not so much.

2nd Date with Thai Smile

Thai Smile just left my place not too long ago. We did not do the do, but it was good night. She showed up with good vibes. She was wearing a halter top with this flowy pants/skirt bottom and smelling delicious. She has a very chirpy personality, which makes her fun to be around. She is a few levels more chirpier than Midwest, but I can handle it in doses. I sense a little anxiety underneath the chirpiness. At this point we’ve all been through some shit. She wasn’t afraid to share.

Early in the date, I leaned in to smell what fragrance she was wearing. While doing that I read she was ready to be kissed. Lovely lips. Thai Smile is very into playing her own version of the question game. She likes to ask a lot of questions. This makes it easy easy to ask questions in return. Most of which I either make up based on the flow of the conversation, or I’ll go to some of the questions from Daygame Mastery or Magnum’s First Date questions. At some point during the night things got heated, and I took a few licks of her clit, and I asked her, “How do you like to cum?” She likes it slow and sensual. This is another reason why I like her and Midwest. They like it slow and sensual. Midwest likes a build up too. A lot of the other chicks I’ve been with this year just want a hard slam. I get anxious with those. When I’m able to take my time I can last longer and actually give the chick some satisfaction…if she’s into that slow, build up kind of sex.

Thai Smile said she wanted to go slow tonight. I pushed as far as I could, and once I read she was at that point I chilled out and we chatted until she had to go. Beautiful body. Smaller upper body, maybe a handful of breasts and a nice round ass. Smooth, supple skin. I want to see her again. I want to learn more about her.

Two points I want to reflect on:

  • Fragrance
    • Since around August I’ve been getting back into upping my fragrance game. I haven’t bought or worn a cologne/fragrance since my ex-wife took mine when she left. One thing that stopped me was I don’t like the way sprays irritate my respiratory system. I recently found some roll-on oils that I like, and all of the chicks I’ve been with since then have mentioned they like it. They only ever tell me this once we get intimate, but I imagine this is one thing that’s pulling them in on the first date. Even this older Italian lady in my building stopped me a few weeks ago to get a whiff. I mention her because she’s very aware of these type of things, and she’s not shy to say it like most women my age probably are.
  • Ideal Situation
    • I feel like I’m going back and forth with what I want everyday. Last post I said one girl would be good. Now I’m thinking two different, consistent girls would be ideal. Two different girls I could see on the regular might help quench my thirst for variety and consistency without being a glutton and neglecting my goals.