Anal Cherry Poppin’

by Leslie

What’s your gender? Woman
How old are you? 39
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Asia
What country and/or city do you live in? Hong Kong
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Nurse
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Buddhist
How religious are you? Somewhat
What’s your sexual orientation? Mostly gay/lesbian
Any other term(s) that describe your sexuality or sexual identity? Having several “FWB’s” at the same time, all female. Having more male friends, but only having sex with women.
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? None

Anal Cherry Poppin’

How long ago did this hookup happen? Last Night

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

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

How long did you know the person before this hookup? For less than 6 months

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? We met in a dance class last Nov 2017. Been meeting up purely for sex once a week at my place or hers. She’s younger, just 22 this year. Young at heart, mind, soul, down to earth. She’s a bisexual, boyfriend, having discreet meets with me as she prefers sex with more matured women at times.

The sex with her has always been amazing, her skills are raw, eating pussy well and I definitely enjoy straddling her with my strapon.

She has always wanted to try anal. I’m not into it, but she wanted to explore so I agreed.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Last night, at my place. We were making out in the kitchen as usual over wine. We headed to my room after that, placed the drinks on the table and she was ready. I used my 7 inch strapon.

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 on her back on the bed, jeans off, ass up. I lubed the strap, licked her opening and then slowly pushed the dildo into her ass. Not as great as fucking her pussy, it was tighter but her moans were more orgasmic, a game changer. We went slow, gentle at first before upping the pace as I did not want to hurt her.

We ended the night laying and making out, change the play to her pussy once again and then she stayed the night.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? Woke up feeling fresh, kissed her goodbye. At least for the next meetups, we will have more in store.

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, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? Didn’t share with anyone. Not many women are open about anal sex. Same goes for me but I didn’t mind as I was the giver.

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

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? I have always enjoyed the sex with her. She’s one of the very few that I fuck on a regular basis and so far she is the longest one I’ve spent time with.

What was the WORST thing about this hookup? I was afraid that the strapon would have been too large for her ass that it could have been a painful experience. I kept letting her know are you sure you want to go through it. Imagine if her boyfriend saw her ass with a larger hole, he might have found it suspicious.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nah it hasn’t

All things considered, how POSITIVE was this experience? A little positive

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

Anything else you want to add about this hookup? For a while, I had been wanting herself and me to become partners. She’s not ready, also bearing in mind our massive 17 year age gap. She’s a sweet young thing, fit with a slightly athletic build, perky 34B cups, trimmed pussy.

What do you think about the Casual Sex Project? I guess it’s a good place to share experiences and stories that you can’t go elsewhere.

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