The Lollipop Girl

by Alex

What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? Southeast Asian
What continent do you live on? North America
What country and/or city do you live in? Los Angeles
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business Owner
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? No
How many sexual partners have you had in your life (including oral sex)? >25
How many hookup stories have you here posted before? 1

The Lollipop Girl

How long ago did this hookup happen? 3 years ago

What was your relationship status at the time? Single

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? “Stacy” was a bratty but gorgeous 18 year old curvy brunette with white skin who wore glasses. She also was a teenage mom. I met her on a popular sugar daddy dating site and was a little apprehensive at first as she was so young. But I did check her ID.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met up only once before just to chat over coffee and then texted for a few months to set up our first real date. Then one summer night out of the blue she says she wants to see me. Her text read “let’s just forget dinner tonight and fuck”.

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? When I picked her up from her mom’s house, she was wearing a white jeans skirt, white sneakers, a simple brown top and hair pulled back. She was also sucking on a red lollipop. OMG I thought. This girl is READY. Since we couldn’t do it at her house, we decided to go to a park. But on our way there, we passed by a mega-mall with a huge parking lot. I immediately turned into the lot and drove all the way to the back near some trees. We hopped into my backseat and it was ON. I start kissing her and she grabs me close to her. I run my hand up her thighs to find that her panties are already soaked. I proceed to lift her top up and her breasts pop out. She is moaning really loudly at this point and so into it, which turns me on even more. I unzip my pants and she strokes my hard cock and then licks every inch of it. After a while, I lay her flat on her back and rip off her panties. She spreads her legs wide and up to reveal a beautiful pink little tender pussy. I feel a bit strange at this point because she looked so young with her little legs spread and sneakers still on. But she urged me on and said, “fuck me hard”. With my cock close to her pussy, I grab a condom. Cock throbbing, I decided to just put it inside her bare to feel her for just a bit. Immediately, she grabs the condom and throws it on the floor. I bury myself deep inside her and thrust hard and fast. As I’m fucking her, I’m thinking that this is the parking lot high school sex that I never had! As she moans more, her body starts to convulse and she keeps saying “harder, harder.” I feel her wetness run down my leg and I’m ready to explode too. But before I do, I pull out and come on her belly. We’re both panting hard and giggling at this point. I start to kiss her while scooping up my cum and putting it on her lips. Afterward, we got dressed, which took forever fumbling in my backseat. We didn’t say too much to each other as I drove her home. When she got out of the car, she said goodbye and said simply “text me tomorrow”.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? It felt great. One of the best pure sexual experiences in my life. I expected that we would have a summer fling and I’d support her with her bills a bit. I was a bit concerned about her young age and getting her pregnant. We ended up seeing each other that summer and then lost touch as we both met other people.

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, Power / Dominance

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

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? The adventurous sex

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 found that younger girls are having a lot of casual sex these days.

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

All things considered, how NEGATIVE was this experience? A little 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 believe that we should all have more sex! People are so uptight in their jobs, their families, their priorities. Sex is good for the body and soul.

What do you think about the Casual Sex Project? Love all the stories!

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