The Rule of Two…

by Linkle

What’s your gender? Trans woman
How old are you? 29
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Worcester County, Massachusetts
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Web developer
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Gay/lesbian
Any other term(s) that describe your sexuality or sexual identity? Attracted to women
How many sexual partners have you had in your life (including oral sex)? 13 (12 pre transition, 1 since)
How many hookup stories have you here posted before? 0

The Rule of Two…

How long ago did this hookup happen? A month ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I met somebody, we’ll call her “cool pansexual lady” on a popular dating site that rhymes with OJ Stupid. Oddly enough, since I came out and started dating as a woman over a year ago, she was the first person to actively initiate contact with me and to make it past the awkward getting to know you phane. She messaged me, made it clear she actually read my profile (where I put in big bold letters “I’M TRANSGENDER”) and seemed really cool. And did I mention she was cute… Like super cute? Short brown hair, a gorgeous smile, curvy in all the right places, and she was a singer too… all plusses in my book! We met up for karaoke one night, and then for dinner a week later. And it was awesome… good chemistry and we were taking things slowly.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Our third date was at my place, Netflix and dinner. I made a calzone and we watched a movie. This was followed by making out and a trip ten feet away over to my bedroom… And yes… my first sexual experience as a woman.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? It started somewhat awkwardly, she was super cool about consent and making sure I was okay with everything she was doing was okay with me but once we figured all that out we simply explored each other and things went from there. Lots of cuddling and kissing, she went down on me, let me finger her (no penetration, but we were both totally okay with that) and then we ended up falling asleep cuddling, me as the little spoon.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We had coffee the next day, left things on a very good note and made plans to get together soon. Drinks a week later and then another karaoke night followed by similar antics. After that we sort of fell out of touch, which might have been for the best. She had just gotten out of a long term relationship and I was developing very strong feelings for another trans friend of mine (who I am now in an aforementioned romantic friendship with). She taught me that a simple fling with no serious long term expectations is an okay thing, and more importantly that I’m not the but ugly untouchable trans woman I once thought I am. I hope her and I do remain friends though.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Discussed STI testing history, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Hoping or expecting it would lead to something more

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? One friend… They were happy for me.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? That it’s okay, and there are people out there who find a woman like me attractive.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

You have a hookup story to share? Submit it here!

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