First Day As A Sissy

by CassieSue

What’s your gender? Genderqueer / Nonbinary
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Cleveland Ohio
Highest education received: Some college (not currently in college)
What’s your occupation? Chef
What’s your current relationship status? Serve all men
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly gay/lesbian
Any other term(s) that describe your sexuality or sexual identity? Sissy
How many sexual partners have you had in your life (including oral sex)? 100
How many hookup stories have you here posted before? 0

First Day As A Sissy

How long ago did this hookup happen? 35

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 3 years

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? Handsome, first time, grew up together, best friends

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Friend caught me in sister’s clothes and makeup, my house, no planning, He did

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? He pushed me to my knees and pulled out his cock and said, “sissy suck it,” and then he did anal sex to me, dominated me, treated me like the girl I wanted to be. I became his sissy bitch.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? Enjoyed it, it never stopped for me

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, Learning new things, experimenting, Emotional intimacy, closeness, connection, To feel better about myself, To feel more desirable, Submission / Relinquishing power, Didn’t want to disappoint my partner, Just happened, I don’t know why, just went along with it, It was easy / convenient

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? Female friends, Older Sister, they approved

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? Being treated as a girl, lost my virgie

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, I’m transgender mtf and it’s the true me

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I have became a cumslut, sissywhore for men

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? Sissys and transgenders become accepted by all

What do you think about the Casual Sex Project? Great way to share and to see how others except what you are

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