by Everett

Gender: Transgender female
Age: 28
Race/ethnicity: White
Current location: Worcester County, 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

Reconnecting On New Years

How long ago did this hookup happen? In the early hours of this morning…

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…)? 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? Get the full story my earlier posting “Let It Go” but in a nutshell… “M” and I met while I was working on my masters degree in 2012. We had a wonderful relationship for two years, she was truly my best friend and she stayed by my side as I began my gender transition. We became good friends again a few months after we broke up, and I ended up going to visit for New Years Eve.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Went to our local hangout for drinks and that time when we’d all ring in 2015 was starting to roll around. Her current boyfriend was working until 3 in the morning and she complained she had nobody to kiss. As I was getting us a bottle of champagne right after the stroke of midnight, she gives me a quick peck and we hugged for a few minutes. After downing a few glasses of champagne we headed back to her place.

Once inside she kissed me deeply and passionately, being that I still have feelings for her I couldn’t resist.

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? We drunkenly meandered into her bedroom and the clothes started coming off pretty quickly. She went down on me (but didn’t allow me to return the favor) before climbing on top of me and that was when I entered her. It was gentle but passionate with lots and lots and lots of kissing.

Did you have an orgasm? Did your partner(s)? She had two, I had none – doesn’t bother me at all, HRT changed my sex drive significantly and it’s not just about having an orgasm anymore, I still enjoyed it very much.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None… maybe we should have but as far as I know she’s been monogamous since we broke up.

What were your REASONS for having this hookup? I still love her very much, she made it clear that she felt the same way. Though we both kept things in perspective the entire time, and before we made love we discussed what we were feeling for each other and agreed this was two close friends and former partners who still love and care deeply about each other simply reconnecting.

Were alcohol or drugs involved? If so, how much? We were both quite imbibed on champagne and Dry Riesling.

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 left things in a good place, I don’t see this changing our current relationship – as much as in my heart of hearts I’d do almost anything to get back together with her (although given the distance we’re now apart and that we are both very different people from when we were together I can also be realistic… but who knows!)

I felt bad because she does have a boyfriend, they’re good for each other and I’m genuinely happy for the two of them. We agreed to not to say anything but what happened between the two of us probably needed to be a one time thing…

To whom did you talk about the hookup? How did they react? I’ve submitted how many stories here… Do I EVER talk about my sex life to anyone else? 😉

Was this a consensual and/or wanted experience for you? For your partner? Resoundingly yes on both accounts

Do you regret this hookup? If so, why? Only because of the aforementioned cheating issue, and I usually pride myself on monogamy and fidelity. On the other hand, it meant a lot to me to be in her arms again, and it’s not like I’m a random girl she met at a bar.

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? Reconnecting and rediscovering a past love, reaffirming that even though the nature of our relationship may have changed we still love each other very much.

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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