Let It Go…

by Everett

Gender: Bigender (male assigned at birth)
Age: 28
Race/ethnicity: White
Current location: Boston
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Web developer
Relationship status: Single
Religious affiliation: United Methodist
How religious are you? Somewhat
Any other term(s) that describe your sexual orientation/sexuality better/best? Attracted to women, regardless of my gender presentation or mood
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 4

Let It Go…

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…)? Non-Sex with an Ex

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? “M” and I met on a dating site while I was in grad school, and we clicked instantly. We ended up being together for two years, getting engaged and living together. I loved her so much and she was one of a few people I felt emotionally safe with, comfortable enough that I was finally able to be honest with myself and in turn her about my gender identity. She went out of her way to affirm me as female when that was how I was presenting and was my rock throughout the early stages of starting hormones. She was my best friend and soulmate, and I would have done anything for her.
In June I accepted a new job in the Boston area that would have allowed us a better future together. I moved in early July with the idea she would follow in August after our lease expired. After I left, she realized she didn’t want to move and decided it was better we went our separate ways. I was devastated but fully respected her decision.
Fast forward to now, I still had several things of mine in storage in upstate New York where we formerly lived and I wanted to close out that chapter of my life. M and I had stayed in touch ever since we broke up and she invited me to stay on her couch instead of with a friend two hours away. I still trusted her and though I never went out there with the intention of winning her back but I still considered her a friend and genuinely wanted to see her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I arrived and we went out for food and live music at one of our old hangouts (bittersweet but I used to go there even before we got together, so I likely would have gone anyway if I was in town). We came back several hours later and both got ready for bed, and she invited me in with her. I had already decided going out there that I wouldn’t want to have sex with her (too emotionally painful) and I knew she wouldn’t try anything. I couldn’t pass up cuddling though…

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? Nothing really, we didn’t even fool around. We just cuddled. I was presenting ambiguously female that day so we were both just girly and cute.

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? We didn’t do anything sexual so it was never discussed. I don’t know if she’s seen other people since we broke up…

What were your REASONS for having this hookup? Closure, a need for physical intimacy, enjoying being in the company of somebody I loved and still love with all my heart.

Were alcohol or drugs involved? If so, how much? A beer earlier in the evening but we weren’t 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? The next day I met with my old gender therapist (I needed a letter for HRT at my new doctor) and then we had lunch. She offered to come with me to help me get my things out of storage. On the ride we finally had a chance to discuss what went wrong and where we stood. Nothing went wrong, we just wanted different things out of life and weren’t the best fit for each other anymore. She felt genuinely sorry that it didn’t work out. I always suspected this but hearing it from her meant a lot…
My hope is that her and I can continue to be involved in each other’s lives. I want nothing but the best for her and she’s said several times that she wants the same for me.

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 on both counts

Do you regret this hookup? If so, why? Only because for a day I felt like her and I were together again and things had gone “back to normal.” Remembering that really we weren’t back together was really hard, I balled my eyes out most of the drive back to Boston.

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? Crying the whole way home was really tough, but after I dried my tears I realized I finally was okay letting go and starting the next chapter of my life.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!