Steve's ENM journey

[Tinwen]

Hello, everyone. Thanks for writing down all your wisdom. I still didn't bring anything up with her as my wife suggested that the mere act of discussing anything related to sex when she doesn't want to might seem coercieve.

Kailtyn doesn't let me touch her boobs or other private parts, not even over her t-shirt or skirt. On the other hand, she freely gropes me and plays with my cock (through my shorts), and if I try to touch her anywhere that is not her waist or face, she gently pushes my hands away.

I took @Tinwen 's suggestion a very seriously I guess. I don't want to talk to her while we were making out but there is always this sexual tension between us and I am trying to find a good time to talk. We currently have privacy only in my truck but the moment we are alone she starts making out.

Start the talking where you're at, that's fine.
Next time you can tell her you'd like to talk a bit before making out, and just ask her current preferences and limits. You don't have to talk about piv just yet, if you don't want to - for example, you can ask what body parts are off limits and where you can touch freely. You can ask whether she's avoiding your touch because she's afraid it would be an invitation to fuck her. You can assure her you won't overstep the boundaries she sets unless she herself wants to go further. People are able to relax if they know their limits won't be overstepped.

Of course, if you're not ok staying at this level of intimacy until she herself wants to go further, maybe date someone more experienced.

You can tell her limits of your own too, like maybe you don't like her touching your cock if you're about to drive (or not at all yet), or whatever.

 

[Magdlyn]

This is definitely the case. I never had to talk about sex with any of my previous girlfriends. We just knew when we wanted to have sex and the clothes came off. I grew up in a fairly conservative environment. So this is all a bit new for me. And it feels weird to talk about sex with someone whom you have not had sex with... I can openly talk to my wife about sex, but with Kaitlyn, it feels weird. She still feels like a stranger.

I will ask those questions while we are on a hike and I will ask her to slow down if she wants to distract me.

When I began my poly-dating journey, I was extremely open with my dating prospects about my sexual preferences, right upfront. Not the gory details (not always, anyway), but in general. I think most polyamorous people would concur that this is the best practice. After all, the first rule of polyamory is communicate communicate communicate. That means talking openly and honestly with new potential partners, not just with your established partner, if you have one.

You do (both) carry the responsibility to not conceive a pregnancy, or spread STDs. That's the big one. But right now, that's a bit moot, since you're not sure she's in any way ready for actual PiV intercourse. She isn't communicating non-verbally (like you and former partners seemingly did) that she's ready to fuck, right now, here's a condom, let's go.

I wouldn't want to have sex with an entire "stranger," myself. I'd prefer to talk about boundaries, safer sex, kink preferences, if any, first. And I don't think you just wanna bone her in your truck, anyway... right?

Sigh... I kinda wish you had a nice over-40 lady to date, who didn't seem like such a neophyte. Someone who knows what she wants, and isn't afraid to say it and seek it and get it. But it is what it is.

 

[Stevek]

I totally forgot to mention that sex with my wife is amazing again. While Kaitlyn gets me all riled up (sorry for the cheap description), my wife is very happy to take care of me.

 

[Stevek]

I have a quick update about my relationship with Kaitlyn. We continued just hanging out while bouldering and some small hikes. I didn't pressure her about sex or anything. I am just happy to be hanging out with someone who has similar interests. Of course there are those make out sessions, which then graduated to full on grinding against my genitals, but I did ask her if she wanted to take things further and reassured her that I was totally okay with how things were evolving. Finally she replied a few days ago that she is ready, and most likely it will happen next week. Patience pays, I suppose. Thanks y'all.

 

[Magdlyn]

So, she must be a virgin?

 

[Tinwen]

So, she must be a virgin?

I would not infer that, and I suggest Steve not tell us! The internet should not know. It's not impossible she finds this blog some day :/

 

[Stevek]

So, she must be a virgin?

I never asked her but she did tell me unprompted sometime ago that she was twice in relationships before.

 

[Magdlyn]

I would not infer that, and I suggest Steve not tell us! The internet should not know. It's not impossible she finds this blog some day.

I'm just asking, not for my own information, but as part of my recommendation to get to know each other's sexual experiences before actually going for it, since she's young and seems quite inexperienced.

After all, there may be bleeding, just for example. If I were about to be someone's first time (any person of any gender) I'd want to know...

 

[Magdlyn]

I never asked her but she did tell me unprompted sometime ago that she was twice in relationships before.

One never knows what "a relationship" means to someone else, and to what level it went.

 

[Stevek]

I am a bit ashamed to ask this here but Kaitlyn hinted about having sex soon and while discussing the logistics, I suggested we go to hotel but she is refusing as she said going to hotel makes her feel like a hooker. I am not sure if that is a valid complaint but she is kind of right that we can't go to hotel every time we want to have sex. She is okay with us having sex at her place but she lives with three other girls and the walls are thin. I am not joking, the other day, we were in her room to just make out and I could hear every thing in the kitchen. I am not like a shy guy but it feels kind of weird. I don't want to subject the other girls to some trauma but I also do not have any other option. I asked Kaitlyn if the other girls ever brought their boyfriends and she told me that one of them is single and the other two are in LDRs and they exclusively go to their boyfriend's place. So she will be the first to bring a guy.

I discussed this with my wife and she suggested that she will take the kids away for a few days but this is just a stopgap and I am not sure what the long term arrangement would be.

 

[Evie]

"I am not sure if that is a valid complaint but..."

No buts, man, she said how she feels and that's very valid. There is definitely a stigma around hotels or motels.

Try suggesting an Airbnb or similar. There has to be something between paper thin wall flat and hotel. Honestly, it could make all the difference.

 

[Magdlyn]

This is a problem as old as time. Whether it's roommates, the kids, your parents, etc., most of us have had to learn how to have quiet discreet sex. Here is a list of some ideas I got from a quick google.

12 Tips, Times, and Positions to Have Quiet Sex

Silent sex can be thrilling and intensely pleasurable. It also facilitates intimacy between partners, which can be beneficial when you’re around kids, parents, or roommates. Here are 12 tips to do it right.

www.healthline.com

I would add outdoor sex to the list. I have had sex right out in nature (in the woods or even in the water), in a tent, or in my mini-van (back when I had one).

Having hotel sex is actually one of my favorites. I consider it a treat. No distractions, no real need to be quiet, a private bathroom, clean fresh sheets, the excitement of variety... I have found them all to be a turn-on. I like Evie's idea of a BnB as seeming less sordid and more homey. You could also bring a bottle of nice wine, a small bouquet of flowers, or a scented candle to add romance and ambiance. The downside, of course, is it's expensive!

 

[MeeraReed]

I do think these things are related to the age difference. I can understand why a 19 year old girl going to a hotel with a married 38 year old guy might feel like it connotes the idea of a "hooker" and makes her uncomfortable. It probably wouldn't be an issue for a woman in her 30s, or if Kaitlyn was having a romantic hotel night with a guy her own age.

So, that might be something to talk about with her. Or about the married/poly aspect of it.

It makes sense that a 19 year old lives in a thin-walled apartment with multiple roommates. Young people have to get creative about where they have sex.

 

[Stevek]

I am not sure why I am writing here but we will finally have sex on Friday. Kaitlyn told me that she is finally ready. I am both exicted and somehow this feels very different than my two previous encounters. I had uninstalled all the apps and I was exclusively seeing her for the past few months. The NRE is still off the charts. I I know that I sound like a douchebag but this is the longest I had to court a girl.

The other day she asked me if I am seeing anyone else (other than my wife and her) and i said no and she also told me that she is just seeing me. I thought she would say more but she didn't bring it up again.

The kids will be at grandparents' and I will spend the night with Kaitlyn and my wife (Emma) is also happy to see me with K.

Wish me luck!

 

[Magdlyn]

I'm sure several of us are glad to get the update! I'd thought this had been consummated weeks ago. But maybe finding just the right location was part of it, as well as just general trust and readiness. So you're going to get to use your own house, it sounds like.

Good luck and have fun. Sometimes patience pays off!

 

[Stevek]

I think I messed up. I was just hanging out with Kaitlyn yesterday evening, and we had some dinner at her place. I went home and was hanging out with my wife. Kaitlyn texted me that two of her house mates are away and the other one will only be coming back late in the night and I understood that she wanted to have sex yesterday evening. The kids were already asleep and I asked my wife if I can meet Kaitlyn. She was totally cool with it and I got into my truck and rushed to her place.

We started with making out and it turned into a 45 minute foreplay where I made her orgasm thrice. It was turning out to be a great night when I realized that she didn’t have any lube. We tried anyway and I couldn’t even get the head of my cock in after almost 10 minutes. FWIW, I am girthier than average and the lack of lube was most likely the problem. We stopped and I performed oral on her again for half an hour. We tried again but I couldn’t penetrate her.

We decided to just call it a night and go to bed. She woke me up in the morning by kissing me and we decided to try again. I was able to penetrate a bit more but she shrieked and pushed me away. I needed to go to work and reassured her that we can try again with lube. She seemed frustrated and disappointed.

I tried texting her since a couple of hours ago and she still hasn’t responded. She usually responds to my texts immediately (unless she is in a class) and I know that she is free this morning. I tried calling her but she is not answering.

 

[Magdlyn]

Thanks for sharing! I am sure that felt disappointing. We still don't know if she is a virgin or not... Was her hymen in the way? Was it your girth? Was she extremely nervous and experiencing vaginismus (unusual contraction/tightening of the vagina)? Did you penetrate her with one finger, or more? Did she seem extra tight compared to other women you've been with?

I don't think you, yourself, messed up. You both gave it a good try. She's obviously worth the wait to you. First, you had to wait months for her to even want to have intercourse, and now you've attempted it, and penetration was nearly impossible and hurt her. I hope lube, or trying other positions, help. Does she use a dildo for masturbation that is smaller than your cock? If not, maybe buy one and use it to gradually stretch her. That works for anal, I know.

 

[Stevek]

We still don't know if she is a virgin or not..

She said she's been with a couple of guys. I didn't really ask anything else as i didn't want to think about her sexlife that much and hence I assume she is not a virgin.

Was her hymen in the way?

I don't think so.

Was it your girth?

Most likely this is the case. I use lube everytime I am with my wife.

Was she extremely nervous and experiencing vaginismus

She seemed nervous but she was the one who invited me. I just didn't think too much about it.

Did you penetrate her with one finger, or more?

Just one and it was tight.

Did she seem extra tight compared to other women you've been with?

Yeah. But she is also the much younger than my wife/other women I've been with.

Does she use a dildo for masturbation that is smaller than your cock?

Wow! haha. this is not the question i was expecting lol. I don't think she has any sex toys but I will ask her about it.

We only tried missionary yesterday. any other positions that can help?

ETA: She still has not replied to my texts.

 

[Magdlyn]

She said she's been with a couple of guys. I didn't really ask anything else as i didn't want to think about her sex life that much and hence I assume she is not a virgin.

I think you should think, and talk, about her sex life. A lot.

I don't think so.

Didn't you look? Or feel it?

Most likely this is the case. I use lube every time I am with my wife.

Well, I hope this helps. I guess neither woman produces much of their own natural lubrication? Or maybe they do and it's just not enough.

She seemed nervous, but she was the one who invited me. I just didn't think too much about it.

I think you should think and talk about it. But of course, she's not talking now... It might be the moment has passed. She's probably feeling a lot of shame.

Just one finger, and it was tight.

If just one finger was tight, I wonder what would have happened if you'd inserted two? The middle finger and the ring finger, facing upwards towards the g-spot.

Yeah. But she is also the much younger than my wife/other women I've been with.

Tightness is not correlated with age. A hymen is correlated with virginity, although some virgins have minimal hymens, or they are broken through non-sex-related activities.

Wow! haha. this is not the question i was expecting lol. I don't think she has any sex toys but I will ask her about it.

I'm guessing if she's got vaginismus, she doesn't insert dildoes. You might purchase one though.

We only tried missionary yesterday. any other positions that can help?

Yeah, all of them. Doggie, side-lying, her on top in control, etc., etc.

She still has not replied to my texts.

I hope she does.

If she allows more experimentation and nothing works, she should probably speak to her doctor. Or you could speak to yours. Get used to talking about sex. I can tell you are both shy to talk, extremely embarrassed. You won't solve this without opening up more. Heh

Have you ever measured your length and girth erect? If the girth is far above average, it can be difficult for some women. I am not sure how many women you've had intercourse with. It sounds like your wife handles it fine with lube. It was a shame you didn't bring lube with this girl! But even if you had, it seems like she might have struggled.

There's a lot of info about this on reddit. A quick look brought this up.

https://www.reddit.com/r/relationship_advice/comments/9s90g/my_penis_is_too_big_for_my_girlfriend

 

[Stevek]

Thanks Mags. I got worried that she is not responding and drove to her house in the evening. I rang the bell and her housemate let me in. I wentto her room and she was a mess. She looked like she had been crying the whole day and I felt very bad for her.

I asked her why she was crying and she told me that she felt ashamed. She said that she felt very bad for making me wait for so long and in the end, I didn't get to have sex with her. I tried to be more direct and open with my questions. She confessed that i made her feel good (with my mouth) and she was able to cum close to a dozen times but i didn't. I chuckled and for the first time in my life, actually had a talk about what I like sexually with someone other than my wife.

I told her that yesterday was eqally pleasurable for me. I told her that performing oral sex on her was was good for me too, as I really like eating her out. I further added that she doesn't ever have to reciprocate as I don't get lot of pleasure from blowjobs and never came from them. She was looking at me like an alien. I just kissed her forehead and she drifted off to sleep.

She woke up later and I told her that she had a long day and we needed to talk and asked her not to stop texting. I told her that we should be communicating openly and even though it is difficult, we should use words and be on the same page.