Virginity Lost Casually to Older Guy

by Kaykay

What’s your gender? Woman
How old are you? 23
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Africa
What country and/or city do you live in? South Africa- Cape Town
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Student
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? 0

Virginity lost casually to older guy

How long ago did this hookup happen? 1 month ago-still ongoing

What was your relationship status at the time? Single

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

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? He was 34, tall, brunette with blue eyes. I knew him for about a month and a half before we actually had sex. A week before we had sex we did oral on each other. I met him online in an online game that had a chat option. We chatted for 9 hours that night and it lead to sexting. We spoke about many things before the hookup so we could get to know each other, we discussed my virginity and he made me feel very safe and comfortable in my body.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began when i invited him over to my home when my parents were out of town. Sexting, and chatting online lead to the hookup. My need and want to lose my virginity, the longing for intimacy and the feeling of loneliness lead me to the hookup as well. Major planning was involved as i still live with my parents and have no privacy, it had to be when they went on holiday. I instigated the hookup when i told him that i wanted to lose my virginity.

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? First of all he rubbed my boobs and inner thigh when we first met. A week after that we did oral on each other. The hookup took place at my home, which started out with me giving him oral on my balcony. During the hookup he went down on me, fingered me, vaginal, 69, general missionary position. It was extremely painful for me, being that it was my first time. He was amazing, he always asked if i was ok durning the deed and tried to make me feel comfortable. He was a good lover, very sweet and was very worried about me and my needs. That hookup ended with him cumming and me in pain.

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, 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? After the hookup we chatted everyday and have since hooked up again and have gone on a few dates. I felt i was on cloud 9 the next day, finally someone wanted me! Unfortunately i feel myself getting a bit emotionally attached to him but a while ago he told me he doesnt want to be in a relationship. Currently im developing feelings for him and i just wish he would stop talking to me day and night if he doesnt want a relationship because he is confusing me.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely

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? I spoke to my friend- she felt sorry for me that i had such a painful experience.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Somewhat

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? The best part was that i finally lost my virginity!!

What was the WORST thing about this hookup? The worst part was the excruciating pain

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Sadly its made me feel a bit like a common cheap whore but thats just societies pressure. In general i think that casual sex is a great way to learn new techniques and i wish that it didnt have such a bad stigma about it.

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

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

Anything else you want to add about this hookup? This hookup it still ongoing, just wish he would feel the same way about me as i do him

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 think casual sex is a good thing, but its also risky, unfortunately i have already had a pregnancy scare. It is also risky emotionally. I just wish it could be a bit more acceptable in society as more people should feel comfortable to do anything they want and be themselves without the dictation from society.

What do you think about the Casual Sex Project? Its an amazing space to share your story, free from judgment and its nice to read other peoples stories

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