by Doublecontralto (formerly Everett)

Gender: Transgender female
Age: 28
Race/ethnicity: White
Current location: Boston, MA
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Web developer
Relationship status: Single
Religious affiliation: Reconciling Methodist
How religious are you? A little
Sexual orientation: Gay/Lesbian
Any other term(s) that describe your sexual orientation/sexuality better/best? Attracted to women
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 5

First Time As a Woman

How long ago did this hookup happen? Yesterday

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? First of more (I hope…)

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 identified as bigendered since December 2013. Recently, I realized I wasn’t bigendered but simply a trans woman. Around the same time I began seeking a full transition, I met “E” on a forum. She was local so we met in person and started hanging out regularly. Her confidence, and the fact she went through the same transition process I am going through now was a huge attraction for me, along with her beautiful brown eyes, long hair and smile. I felt so safe with her that I was finally able to start presenting in public as myself and not someone wearing a male mask.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I asked if she’d accompany me on a weekend back to upstate New York to visit some friends. We made it to Binghamton and went out to a bar I used to frequent. After an evening of unconditional love and support from pre-transition friends we got back to my friends apartment as I was feeling on top of the world.

We went back to my friend’s apartment to get some rest and ended up cuddling.

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? She had figured out by this point I had a crush on her. She was honest, told me I didn’t fit her usual type and she wasn’t sure what she was looking for right now in terms of a relationship but was open to seeing what would happen. We ended up cuddling, kissing, and fooling around. Since we were sleeping on a friend’s couch, she didn’t want to go any further but we continued our girlish fun and exploring each other’s bodies until we were tired out and fell asleep in an embrace.

Did you have an orgasm? Did your partner(s)? No

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No bodily fluid was exchanged so it wasn’t a concern.

What were your REASONS for having this hookup? I’ve had a crush on “E” since we met, circumstance allowed us an evening of enjoying each other’s company and bodies.

Were alcohol or drugs involved? If so, how much? None. We had some drinks earlier in the evening but we were both sober by this time.

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? We woke up several hours later and went about our next day in Binghamton. Of course I am still very much attracted to her, hopefully we’ll continue to explore our friendship together and see where things lead.

To whom did you talk about the hookup? How did they react? Nobody

Was this a consensual and/or wanted experience for you? For your partner? Yes

Do you regret this hookup? If so, why? No

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? My first sexual (even if we didn’t have sex) experience as a woman was affirming and wonderful. It was a perfect end to a perfect evening. I really really like her and am excited to see where things lead.

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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