by Rachelxd

What’s your gender? Genderqueer / Nonbinary
How old are you? 34
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Scotland
Highest education received: High school diploma
What’s your occupation? Construction
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Lady in training
How many sexual partners have you had in your life (including oral sex)? 37
How many hookup stories have you here posted before? 0

My 1st 24 hours as a cross dressing tart

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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 text a gay chat service on TV and got a reply from an older guy who sounded nice and he loved cross dressers, so we met at my house that night without even seeing a picture of each other.  But he was lovely and had travelled a lot and knew what he wanted – but I was a bit nervous and topped myself with bit of wine which helped loosen me up.  I got myself looking really feminine, got an expensive wig and a nice dress full makeup high boots, and when he called at my door I towered over him in my 6″ heels.  I thought, “shit what do I do, take the boots off or leave it?” but he was really turned on and wanted me to walk round the room so he could watch me stroking his already hard cock.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We started texting in the morning and I was up early – my housemate was away for the weekend, so I had a shower and took out my best dress for a morning of cross dressing, doing makeup.  I started getting a bit horny and thought, “Wouldn’t it be great just to talk to a guy and see what happens?”  I had never tried anything like that before and then when we got talking it was all sexual banter which just boiled over and we had to meet that day; it was a must.

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? I had never been with a man before and certainly not while dressed as a girl so it was daunting at first but when we met we just had a good snog (as you do) while he was groping my bum cheeks and kissing my neck.  Then he sat down and unzipped his jeans and pulled them off.  I just got down on my knees in “worshipping his cock” position and looked him in the eyes while I slowly leaned to his big thick dick and put my lips around it and slowly sucked up and down until he was ready to explode.  He then reached to his pocket and pulled out some lube and condoms.  He then lubed his fingers and started rubbing it on my bum and I knew I was about to get pumped.  I was real horny by this point and I just put the condom back in his pocket and sat on his hard cock.  We stared real slow and it felt magical with his throbbing raw cock in my ass, and oh my god we both came together and he filled me with his cum.  I could feel it rushing out of him inside me – it was a feeling like no other.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one.

Did your partner have an orgasm? Yes, one.

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? We never spoke again after our hookup but I will always remember that day.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, to feel better about myself, I was feeling lonely, submission/relinquishing power

How intoxicated were you? A little tipsy/high.

What substances did you consume? Alcohol, marijuana, hashish.

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? I told my ex-girlfriend and she didn’t mind; she actually wanted to know all about it.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

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? Great 1st time gay sex dressed as a girl.

What was the WORST thing about this hookup? I can’t remember his name.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all, I would do it again.

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

All things considered, how NEGATIVE was this experience? A little negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? It’s not something I make a habit of doing often

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

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