Giving Away My Anal Virginity



What’s your gender? Man
How old are you? 22
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
What country and/or city do you live in? India
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Student
What’s your current relationship status? Single
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Bi-curious
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? None

Giving away my anal virginity

How long ago did this hookup happen? This happened around three months back with a man I met on Grindr ..

What was your relationship status at the time? Dating casually

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’d tampered with my asshole pretty often,inserting all my five fingers and even small deodorant bottles. I needed some real cock this time. Had been on Grindr twice before and chickened out. Was in no mood to chicken out this time.

Found a man on Grindr who stayed 10 miles away. He was average looking and pretty short. Like 4-5 inches shorter. He had a 7 inch cock. I thought cock size would be enough and physical attraction was not necessary.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I invited him over to my place. I lost my anal virginity on my parent’s king size bed. No planning as such apart from lube and condoms.

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 entered the empty house and I guided him to my parents room. The room was air conditioned and I locked the door. We looked at each other awkwardly and I told him it’s my first time and so I was nervous. Without wasting any time, I started unbuttoning his jeans and pulled it down. Pulled down his underwear and started sucking his cock. It was horrible, nothing like I imagined. Licking it at first was okay but sucking it was horrible. He fucked my throat for nearly a minute and I gagged multiple times. I wasn’t enjoying this one bit.

He then ordered me to take off my clothes and I did. Then he wore a condom applied ample lube on my hole and condom. I was in a doggy position and he was on the edge of the bed. Smoothly, his dick entered my asshole and he started pumping. He told me to look into the adjacent mirror and I could see my asshole being taken apart. He fucked me for a few minutes then changed position. Made me lie on my back putting pressure on my neck and my knees touching my shoulder, he fucked me harder. There was not too much pain to be honest and I was finding it decent. The only time it hurt was when he took his dick out and then pumped it all the way in.

There were small slight shit stains on my bed which was surprising cause I’d cleaned up pretty well. I watered them quickly and then we proceeded for round two. I lay a newspaper just to avoid any stains. He went again with the above two positions and tried another side by side position. He pumped me vigorously in the end and I told him it’s hurting and he told me just a few more strokes. He came for the second time soon.

In between he fingered my ass, putting all five fingers in. Kissed all over my body and sucked my boobs. He kissed my lips but I stopped him henceforth. He came twice and I wasn’t even erect. I enjoyed the anal only to a certain extent.

How sexually satisfying was this hookup? Not at all

Did you have an orgasm? No, not even close

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? My expectations were drowned. I blocked him on Grindr and uninstalled it. Stayed away from gay sites and have only thought about it again now. I think I need a good looking man to make it a sexually satisfying experience.

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, Learning new things, experimenting, Thought it was an important experience to have, Submission / Relinquishing power, Just happened, I don’t know why, just went along with it

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? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

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. And I never will.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? I don’t know / I’m not sure

Do you regret this hookup? Somewhat

Why do you regret this hookup? I should have lost it to a good looking and fit dude.

What was the BEST thing about this hookup? The anal was okay.

What was the WORST thing about this hookup? Sucking his cock. It tasted horrible.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yeah. Pretty apprehensive now.

All things considered, how POSITIVE was this experience? Not at all positive

All things considered, how NEGATIVE was this experience? Fairly 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? I wish India was more open to it.

What do you think about the Casual Sex Project? Great initiative. Love the stories here. Kudos!

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