by Wynona

Gender: TransFemale
Age: 23
Race/ethnicity: White
Location: Chicago, IL
Highest education received: Some college (not currently in college)
Occupation: Writer
Religious affiliation: A hybrid of Buddism, Taoism, & Veganism
How religious are you? Somewhat
Sexual orientation: Gay/Lesbian
How many hookup stories have you here posted before? None

My Vagina’s Maiden Voyage

How long ago did this hookup happen? One Night

How would you best classify this hookup? One-Night Stand

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? Her name was Amy. She was so fantastically hip with her harem pants, undercut, horn-rimmed glasses, and a job as a video editor for a national online news outlet. Her sense of humor was as precise and as sexy as the equations she had etched in ink on her right shoulder – something about speed of light or sound. Swoon! And she was MAJOR flirting with me!

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had just returned from Thailand with my shiny new, but still swollen & sore, vagina. Despite the pain, I was determined to take her for a test run. There’s no better girly hookup place than Cubbyhole in NYC (where I was living at the time)! So I gathered up my bestie and headed downtown.

Coming on strong has never been a forte of mine, so I was really thankful when Amy approached me with a drink and we started talking. Small talk flirting led to joke telling flirting led to little brushes and touches flirting led to lots of touching flirting led to forget about our friends flirting led to forget about the rest of the room flirting led to lip-locking in the backseat of a taxi cab on our way back to my place (she lived in Brooklyn, of course).

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? During the hookup I was incredibly wrapped up in whether or not she knew I was trans. There’s a lot of signs trans* people who are hoping to stay stealth know for which to look if we’re trying to decipher whether people “can tell” or not. How a person refers to trans* people, whether they ask you questions that are exclusively cisgender related, how a person refers to your childhood (ie “What was it like growing up as a lesbian?”) – stuff like that. Amy hadn’t really hit any of those topics and so it left her interpretation of me a little nebulous (or in hindsight: obvious).

On top of that, my vagina was less than 2 months old and I was still figuring out how to work it. So a lot of the hookup was making out, rubbing together with underwear on, and me going down on her.

She was a little more aggressive than I anticipated, but that was great! She was the instigator of every next step. I remember her and I being VERY kiss compatible. Just the right amount of tongue at the right time.

The sex melted into snuggling really seamlessly. We both felt satisfied, I think, and just found ourselves cuddled up.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t use any sort of protection nor did we talk about STI history – just blind trust and assumption.

What were your REASONS for having this hookup? I found her EXTREMELY attractive and had a desperation to share my body with someone else after spending a month in the hotel room recovering from surgery. I was proud of my vagina.

Were alcohol or drugs involved? If so, how much? We were beyond buzzed but before drunk.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Afterwards she stayed the night and in the morning she showered and headed to work.

I’m embarrassed to admit that I’m HORRIBLE at one-night stands (despite doing my fair share of practicing). I was super into Amy and was making plans to hang out later in the day or later in the week. The devastation was exceptional when I realized that it wasn’t going to be happening – that it was just a hookup for her and nothing more. Amy is still a super cool person in my mind. Her essence is that Brooklyn Lesbian brilliance that’s so often copied. I may or may not have called my mom after Amy left. I was so excited. My mom had spent the month with me in Thailand and we had gotten really close, so it felt right to call and share my first experience with her. She reacted very supportively and did a great Mom job of listening.

Was this a consensual and/or wanted experience for you? For your partner? It was definitely consensual and wanted from both parties.

Do you regret this hookup? If so, why? Absolutely not! It was such a wonderful learning experience and a wonderful sexy experience.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing was the confidence I gained as a viable person of interest in my community.

I don’t know that there was a “worst thing”. The least pleasant thing was feeling rejected in the relationship department when it became clear we weren’t hanging out more.

My night with Amy reaffirmed my inability to compartmentalize when it comes to one night stand sex and relationship sex. So I’ve learned where my weaknesses lie in that emotional area and I’ve worked on being better prepared for the “let-down” part I’ll go through after a one-nighter.

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

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

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