Every Boy’s Fantasy



What’s your gender? Man
How old are you? 17
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
What country and/or city do you live in? Singapore
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

Every Boy’s Fantasy

How long ago did this hookup happen? 15

What was your relationship status at the time? Single

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? She was my tuition teacher. She was 28yrs when I was 17yrs in college. I was struggling in Maths. She was mature and professional as a tutor, very kind and caring. She had shoulder-length hair and was short and shapely. She was usually in casual jeans and blouse. I did not feel much about her in the first few months because she was very focused and professional. After more tuition sessions and we became more comfortable with each other, she starts to appear very attractive. I started to notice what she wears, fantasise about what she is wearing underneath her clothes and how she looks without. There’s always a secret guilt when I catch a glimpse of a loose bra strap or a vpl. I feel safe and comfortable with her, like I can share all my problems. She turns out to be quite the big sister I never had.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The very first time was during a tuition session and was unplanned. Neither of us instigated but I felt both of us wanted it to happen. There was no sex involved, only mutual masturbation. We started because she read my personal journal which she thought was my Maths notebook. We subsequently had oral sex in the next session and penetrative sex soon after. We did it where we could have privacy – her room, my room where we had tuition, hotels, on vacations.

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 excused myself to get drinks for us on that warm afternoon. When I returned, she was reading my personal journal in which the last few entries had my thoughts about sex and recorded my fantasies about her. I thought she was checking my Maths notes, until she looked up at me, face red, and when I realise what had happened I turned red too. I apologised and explained as well as I could. I said I respected her a lot but cannot help having a crush on her. All that I wrote were in my mind and I would not have acted on them. She asked me if I am allowed the opportunity, would I do so, to which I nodded my head. She excused herself to what I felt was a long time to the toilet. When she came back, she corrected my misconception about her, female and male sexuality, masturbation etc. She said I was masturbating wrongly. I replied by asking her if she can educate me about all these. That day, we had a discussion about male and female masturbation and we practised. She said we need not fantasise and can just watch each other to get off. I wanted to touch her and asked if I could help. She gave me directions and that day was the day of many firsts for me. I saw her moaned in orgasmic ecstasy of which later on in our relationship she revealed to me that that orgasm was the benchmark for her from then on. That day, she taught me how to jerk off and that it doesnt only involve just wildly tugging at my junk. She guided my hands in finishing me off and that scene of her in her white panties, opened blouse with her tits almost falling out of her white bra cups, sitting in a chair in between my widespread legs, was an image that I will never forget. Before she left that day, we kissed goodbye and our lips lingered on each others’ for so long I had to jerk off again after she left. We didn’t talk much about that afternoon after. Just confirmed the next session. When we met next, we performed oral for each other. The following two sessions were similar, and for each of these sessions, she became more casual and adventurous with her clothes. She came in a bright orange sports bra and tight yoga pants and brought her sex toys on the fourth session. While we had been kinky and sexual in these sessions of tutorials, we had also been respectful and thoughful to each other. It was clear by that time though, Maths tutorial was second on the agenda. She gave me work after each session and I would do them and she would correct them at the start of the next session. It was clear that I had already caught up with my subject and can manage with only a little help from her. On the fifth session, we finally had sex. We didn’t plan for it. For the past sessions we will take about half hour with my work, and she’ll end the consultation, whereby which I’ll then draw my chair close to her to cuddle and make-out. That day, she was in the middle of fondling my private parts when I blurted out if she wants to fuck me. She straddled and rode me hard on my single seat sofa, her blouse over her head, her black half cups barely keeping her tits in. Her nipples were peeking over the laced seams. As she bounced, her ample C-D bosoms followed her rhythms. She seemed to know it as she enjoyingly watched me fixate on them and occasionally rubbed them in my face while holding onto my shoulders for support. She came first. I took a while longer because I was nervous and she said it’s good cause it was still hard. She whispered for me to cum in her. I buried my face in her cleavage and pumped up her gyrating hips. I caressed her back in one hand and tugged on her half taken off panties at the thighs with the other hand. She later told me that she never had felt cumming in her and wanted to try on me. It turns out she had been planning it and was on the pill for some time. Our time together lasted for a year or so until I graduated. We did it at her place, on long weekends in hotels and on holidays overseas. We knew it had to come to an end so we decided that before I enlisted, we will end it. We lost contact for quite some time until when I was in my last year of university and a couple of failed relationships later. We ran into each other on the street and our desires reignited. It finally ended 2 years ago when her on-off boyfriend eventually proposed.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? I feel very blessed to have had this very special relationship with her. We only keep in contact through messaging over seasons and birthday greetings. She is my go-to fantasy when my gf is not available and it’s even more wonderful to know that I’m actually remeniscing and drawing up on my memory, not just a childhood fantasy. Like how she taught me when I was 16, that there are only some ways I could touch myself that no lover ever I could. I wish I could tell her in future that she was that someone which could touch me the way I touch myself.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, Condoms, Birth control pill / patch / ring / injection / implant, Fertility awareness (days counting, temperature)

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

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? Not at all

Do you regret this hookup? Not at all

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