Popped My Anal Cherry

by ItsElle

What’s your gender? Woman
How old are you? 30
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Australia
What country and/or city do you live in? Maroubra
Highest education received: Post-graduate degree (currently pursuing)
What’s your current relationship status? Single
How many sexual partners have you had in your life (including oral sex)? 4

Popped My Anal Cherry

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than a year

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? This follows a previous story about a new partner. We met in my current workplace and he is 2 years younger than me of middle eastern descent.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met again a week later one Friday afternoon. He messaged me if I wanted to come over I said yes.

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 went over to his place after work and waited to come inside. We went to his room and laid down on his bed where I had laid towels down because I was at the end of my period. We made out and took our clothes off and his dick was already hard. I sucked on his cock and he recorded me from his phone. I gave him a blow job and then he got a condom out and we fucked missionary until I came. Then, he got a toy with lubricant and inserted it into my butthole to stimulate it before he inserted his dick with heaps of lubricant. I told him to go slow as it was my second time and didn’t have a good experience previously. I let all my pain out by crying a little. I moved too many times and had to keep still to avoid waking his roommate. He asked if I was ok which was nice though and I did end up having multiple orgasms. It was an intense but enjoyable experience with someone who was gentle. Having a toy really helped rather than inserting it straight, so I liked this time better.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? I don’t know

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 hugged and made out for a bit more and then we went our separate ways as he had to go somewhere later that night. I felt really good. We couldn’t be together romantically but remain workmates with a fuck buddy arrangement and thought it would be better that way.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have

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? no one

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? Popping my anal cherry with someone new. Fucking him again and orgasming several times.

What was the WORST thing about this hookup? We couldn’t be together but it’s all good.

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

All things considered, how NEGATIVE was this experience? Not at all 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? Im enjoying it until I find a new potential love interest.

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