Okay, so I’m a 20 year old cisgender lesbian, and I’ve only ever had sex with other cisgender women and that’s only consisted of oral and fingering.

I’m not super sexually experienced and have never orgasmed with a partner. I also find fingering very uncomfortable. I was looking through past posts in this sub on the subject of penetration, and a lot of commenters brought up vaginismus. Personally, I use tampons, have fingered myself, and have inserted toys before, and none of those cause discomfort. Additionally, the insertion of the fingers itself when other people have fingered me isn’t uncomfortable at all. I think it’s because I’m a very large woman, but the women I’ve been with have fingered me very roughly. I had this one fwb, and she would ask if the fingering felt good, and if I said yes she would immediately switch what she was doing to pounding super hard. She tried working me up to taking a strap on, but when she fingered me with 3 fingers it hurt too much, so we ended up not doing that.

Anyway, fast forward to now. I met a woman online and we agreed to hookup. I am nervous as hell though because she’s trans and I’ve never been with a trans woman before (I told her this and she said she’ll be patient with me). I’m just nervous that it’ll hurt especially since neither of us can host so she agreed to pay for a hotel room and I’d just feel so bad if she went through all of that trouble only for me to pussy out. So any tips for easing pain with penetration (also I heard commenters on other posts mention lube, but how do I know what kind to buy)? Also if anyone could just tell me what to expect in general I would appreciate it.

3 comments
  1. I would say just take it slow, and be very honest with how you’re feeling physically and mentally. If you’re really nervous you could try using toys and stuff leading up to the meeting. It might hurt at first, but is very pleasurable once you get used to it. My husband and I recently tried uberlube which is a little expensive but it’s amazing for penatrative sex, and mixes greatest with spit for handjobs. Good luck on your journey I hope it goes well!

  2. Buy some water based lube just go to the store and you will be met with lots of options. I really suggest lots of forplay. Don’t rush any sort of penetration wether that be fingers or a penis. Also if she is taking hormones that can effect the bodies ability to cum, stay hard, or libido. So you also my need to be patient with her. Lastly penetrative sex can be really enjoyable when you can be relaxed as possible. I’d recommend you trying being on top and grinding your hips: it’s not all about bouncing up and down. Anyways I home the helps!

  3. You really don’t have to do the PIV, it’s not “pussying out” if you change your mind. If you feel like you’ve committed to it and that you ought to follow through, you’ll be nervous and it will be more difficult, even if you do really want it.

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