This post is sponsored by Trust.
What’s your gender? Transwoman
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 (and transwoman are women…just to put that to rest).
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? 1
Look in the Shoe!
How long ago did this hookup happen? 2012
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? Just for the record – this happened while I still identified as male (I transitioned late 2014)…
A few months prior, my ex, who was a few years younger than me, broke off our long distance relationship after stringing me along for quite some time. It ended up with her taking a trip I had planned for the two of us to Florida by herself. I was hurt, depressed, and angry for months following that. What followed was the summer of 2012, which I (not proudly) refer to as the “summer of hookups”, when I went through six different women in a period of about four months – everything from one night stands from a bar, to short relationships. “A” was in the later category. Met her on a dating site whose name references fishing…. “A” was an 18 year old pre-med student at an Ivy League school about 40 minutes away from my house. Came off as really intelligent and sweet when we chatted online, and she was also a ballerina and had been dancing since she was 6. I always had a thing for dancers and even if she wasn’t one – from her pictures at least, she was **stunning**. We kept chatting for a couple of weeks on and off, until I made an excuse to go to her city, so we could meet up.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was done with classes for the day around 11 and we agreed to meet at the library across the street from the building where her class was held. I was sitting on a step, looking away, and the next thing I hear is “hey, are you [my pre-transition name]?” I said I was, stood up and the next thing I knew we were twirling each other around and kissing. It was kind of corny (like out of a cheesy rom-com) but actually quite romantic. We were planning an impromptu picnic, but because it was so windy she suggested we grab food and head up to her apartment which wasn’t far away. Got the food, went up stairs, and hung out with her and her housemate for a bit while we ate, and she showed me some of her Youtube clips from her most recent production of the Nutcracker (the last thing she performed in). Soon her housemate left for class, and no sooner had the door closed we were all over each other, tearing our clothes off.
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 was just as stunning in real life, incredibly beautiful in a really elegant way, but I soon found hiding underneath the elegance was somebody who was incredibly sexual and highly insatiable. I sucked her nipples briefly before kissing various places on her body and going down on her (and she made it clear she REALLY liked this – I had never been with somebody so vocal before.) Eventually she stopped me and said “wooden shoe”, I looked puzzled before she said again “look in the shoe!” pointing to a decorative wooden clog that was on her desk. Inside I found condoms, grabbed one, climbed back into bed with her, slipped it on and she climbed on top of me. As a dancer she was highly flexible and was able to bend her body in ways I could never have imagined as she pushed me deeper and deeper into her, and used the same flexibility to tease me and keep me on the verge of exploding – hence she came multiple times and I had probably one of the most incredible orgasms of my life. We cleaned up, climbed back into bed naked and made out for over an hour.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, one
Did your partner have an orgasm? Yes, multiple
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? It was still relatively early in the day, “A”‘s housemate came back to us napping so we eventually got dressed and went to dinner together. Later in the evening we saw a friend of hers in a modern dance performance on campus (which was very good) while we simply enjoyed each other’s company, her housemate mentioned she was going to her boyfriend’s that night and “A” invited me to stay over. I had a conference to go to the next day but I told her I’d stay over anyway and just needed to leave early. Similar antics happened that evening – and I learned that her nipples were so sensitive, merely touching them drove her wild. She said to me “if you even accidentally brush against them, I’m going to make you look in the shoe!”
We got together several more times over the next month – I saw her in a production of Swan Lake and we went to a concert together. I didn’t have high hopes for her and I going anywhere as a long term relationship, due to the age difference (she was 18 and I was 25 at the time), turned out she also had a boyfriend in Minnesota and was cheating on him the whole time. I was hurt but got over it fairly quickly.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To feel more confident
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? Nobody
Did you get emotionally hurt as a result of this hookup? A little bit
Did your partner get emotionally hurt as a result of this hookup? Not at all
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? It was extremely enjoyable for both of us.
What was the WORST thing about this hookup? Being hurt by finding out I was essentially a way of mitigating her horniness. We all have needs, and for all I know her and her boyfriend might have had an open relationship, but I thought it would have been nice to have been told this up front.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I had wanted to have sex with a dancer for a long time at this point. Quite honestly, I think it stemmed from my (at the time) repressed gender identity, and the fact I always wanted to dance myself growing up, but was afraid to because I wouldn’t have been seen as “masculine enough” (remember, I was growing up in the 90’s and 2000’s – this is back when being gay or lesbian still had stigma attached to it, let alone being transgender – hence I tried very hard to be a “normal guy”, until at age 28 I realized that I just couldn’t keep up the act any more). Ironically, now being on hormones for a year and a half, and fully out for nearly a year, I still don’t dance. I’m just more free to be myself.
All things considered, how POSITIVE was this experience? Fairly positive
All things considered, how NEGATIVE was this experience? A little 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!