Sugar Daddy Diaries - Shaye the 18 year old
- Jul 3, 2025
- 22
- 137
- 28
I’m a year into a sugar dating experiment and it’s fucking fun. I’m writing about my experiences for my own titillation, and maybe the SF boys will enjoy too.
Instalment #2 - Shaye, the 18 year old
If there was ever a platform for unrealistic dating experiences, it’s the sugar daddy websites. Sure, you can pay to lay down with any aged woman from 18 through to 50+ for an hour at a time at a brothel. But actual “be seen in public” dates with a girl far outside your norm? Only found online.
Seeking Arrangements has a monthly charge on my credit card, and that’s where I found Shaye, a sweet carefree brunette that was only 18 years old.
Shaye was fresh out of high school and enjoying the freedom of friends and fun with no commitments. And when I say fresh out of high school, we first met in late January after her 7th form year finished a month or two earlier!!
My strategy on these sites is to put out a reasonable message to any profile that ticked my search parameters, and then talk to them from there. If they could produce more than one line replies, they were worth pursuing to see where the rabbit hole led to.
Shaye displayed a willingness to engage back, even if the discussion wasn’t much more than expected of a high schooler. She was not a future Harvard graduate, but not a painful airhead either.
Shaye’s parents worked in the city, so we arranged to meet at Britomart one afternoon, after she got a free ride with her actual daddy into town. She was obviously nervous upon meeting in person some random guy from the internet, twice her age, who she was aware wasn’t just there for the coffee.
I approached the date carefully and respectfully so I didn’t scare her off. I knew enough about her thoughts, hobbies and interests from a week of messaging to keep the conversation flowing. After a bite to eat we went for a walk towards the Viaduct and talked some more.
I found her youthful shyness a fun challenge. Was I a predator, preying on a young gazelle fresh from the safety of high school kids? I’m not gonna lie, I did have moral doubts for a moment, but they were definitely brief. She was legal after all, and SHE had signed up to a sugar daddy website all by herself.
Moral doubts aside, when we were in a quiet spot on the waterfront, I asked Shaye if I could kiss her. She smiled back and touched my arm to say yes. First base unlocked.
Shaye never asked for money, but on the walk back through Commercial Bay we stopped into some shops. Shaye picked a perfume and a bodywash she liked. I guess receiving gifts was her love language. Did she yet know every man’s love language is physical touch? Haha. We said our goodbyes and little Shaye walked back up Queen street towards daddy’s office. As I watched her blue jeans and Glassons top walk away, I wondered if I would ever see those clothes on my bedroom floor.
The next day I was out and I got a Snap from Shaye. She was trying on some clothes with a friend at a mall. She asked me whether I liked the tight top she was trying on, cleavage showing, just below her long kissable neck, and sweet smile looking at me in the changing room mirror. Her friend was in the picture too. Smiling with a teenage grin, full set of braces showing. I shook my head thinking wtf was this fantasy I was delving in to.
I agreed to send Shaye the money for the top she just showed me, hopeful the investment would soon pay off. She agreed to let me see what I had paid for the next day. And she wanted me to see it at my house!!!
Saturday morning arrived and Shaye’s grey Nissan Primera pulled into my driveway. I had made sure to clean up the bachelor pad and change the bedsheets, ever hopeful of soiling them later that day. Shaye gave me a big hug on arrival and asked if I liked her new top. She told me to lean in and smell what I had bought her from Mecca at Commecial Bay a few days prior. Sweet heaven, is this what being a hero felt like??
Shaye sat next to me on the couch and giggled away in the afternoon sun. We were now into week 2 of messaging, second date, and a lot of snaps back and forth. She had reached comfort levels already and was following her carefree spirit. After laughing at one of my lame jokes, Shaye looked me in the eyes, jumped over to straddle me, then started kissing me.
She wasn’t an experienced kisser. They weren’t the passionate tongue teasers you get from an escort that’s paid to do this 20x a week. They were gentle, youthful, inexperienced kisses. They were nice. They were different to what a guy in my age bracket is used to.
After 20 mins of kissing, and dry grinding on the couch, Shaye asked where the bedroom was. I showed her the way and she popped into the ensuite bathroom. My heart rate was racing a lot by this point. The BPM jumped even further when Shay walked out, only in her bra and undies, with a mischievous smile on.
We went to the bed and kissed some more. Shaye helped take my own clothes off to match her own lack of fabric. “I like dad bods, the boys at school were always too skinny”. Nervous chuckles from me.
We rolled around further and my kisses moved from her lips, to her neck, to the tops of her tits still covered in a small bra, and then to her stomach and inner thighs. I could smell sweetness a few centimetres away.
I asked Shaye if I could lick her pussy. She smiled and nodded in agreement before I removed her undies. Staring back at me was what I could only describe as vaginal perfection.
18 year old, white girl pussy. No large skin flaps, a perfect inney. Completely shaved like she was not yet a woman, but plenty of stubble from inexperience at grooming down there. The light touch of her own juices at the bottom of her opening, visible in the sunlight. Slightly enlarged clit, but still nestled under its hood.
I showed her a few tricks I had learned over the years and managed to make her orgasm. No fake moaning you get from the paid companions. She was quiet as a mouse, only a small moan and muscle jerks when the little fireworks went off.
Here’s where the train of delight started to derail. The train driver wasn’t on his best game. I was failing to get hard myself. What the actual fuck!? Why was my anatomy letting me down during this moment of… unbridled teenage corruption?
A lovely 18 year old girl was in my bed, no panties on, wet as fuck and my member wasn’t performing. The pressure of the situation, combined with the absolute mismatch of age, background, and normalcy, had got to my head. Sure I had fucked girls younger than me before, but never had I had some girl so young, in my own home, in my own bed, with no clothes on before. I was actually nervous about the situation! And my dick was limp. The embarrassment of it all.
I asked Shaye if she would give me a blowjob, not letting on that this flaccid state was entirely unusual and disappointing to me. “I’ve never done blowies before, I don’t know what to do”. Oh well, this isn’t a moment for me to teach you that skill sweetheart.
We returned to laying down. I wiped my mouth and went back to kissing her, and playing with her pussy. She was so young and naive, she was just going with the flow of things. What was a personal failing of mine must has come across as gentlemanly pacing. No rushing to fuck her flower. She must have thought real men took their slow slow time!
Then I remembered something spectacular! Hidden in the depths of my glovebox was an old mostly empty pack of blue pills. Kept there for when I wanted to fuck more times than the body would naturally allow. I hadn’t used them in a year or so, but I was pretty sure at least one was left.
I made an excuse to get us both a drink and popped into the garage. Found what I needed, downed the full 100mg available, and returned to the 18 year old laying in my bed.
Every fairytale has a happy ending, and half an hour later, I was plowing my now raging erection into this young girl. I took it easy and didn’t want to completely break her pussy in. I didn’t want to her driving home so sore she never returned. But the blue magic had done the job, and I was good to keep going for quite some time!
Shaye was a young starfish. She didn’t really know what she was doing, and her inexperience did show. She told me she had had sex a few times with boyfriends during high school. But nothing serious. She told me how those boys only ever lasted a few minutes and usually couldn’t make her cum.
Shaye stayed until it got dark and she noticed a bunch of missed calls from mum. I laid next to her when she called back to say she was at a friend’s house, and she would be home soon.
Over the next few months I never did teach Shaye how to give blowies, as she called them. I was content letting this little teenage starfish lay back while I did all the work. Once or twice a week Shaye would send me videos of her trying something on with friends at the mall. I would send her whatever amount the price tag said. Shaye would come over on the weekend and show me what I had bought.
Once we went to St Lukes together and I followed behind her from shop to shop, enjoying the little fashion show, knowing that in a few hours she would be coming back to my place to let me fuck her.
It was never going to be a long term or serious thing, and in June (last month) Shaye departed with some friends for some backpacking adventures. All in all she would have parked her Primera in my drive way around a couple dozen times. Hard cash never exchanged hands, but I definitely paid for the fun that was had in other ways.
Was Shaye really 18 or was she like the 18 year olds on escort sites (meaning in her mid 20s). I definitely saw her insta posts with her friends in red-crested Mahurangi uniforms only just last year in 2024. We never used condoms, but she did assure me she was on the pill.
Shaye was a fun time for a few months that will be etched into my wank bank of memories.
Instalment #2 - Shaye, the 18 year old
If there was ever a platform for unrealistic dating experiences, it’s the sugar daddy websites. Sure, you can pay to lay down with any aged woman from 18 through to 50+ for an hour at a time at a brothel. But actual “be seen in public” dates with a girl far outside your norm? Only found online.
Seeking Arrangements has a monthly charge on my credit card, and that’s where I found Shaye, a sweet carefree brunette that was only 18 years old.
Shaye was fresh out of high school and enjoying the freedom of friends and fun with no commitments. And when I say fresh out of high school, we first met in late January after her 7th form year finished a month or two earlier!!
My strategy on these sites is to put out a reasonable message to any profile that ticked my search parameters, and then talk to them from there. If they could produce more than one line replies, they were worth pursuing to see where the rabbit hole led to.
Shaye displayed a willingness to engage back, even if the discussion wasn’t much more than expected of a high schooler. She was not a future Harvard graduate, but not a painful airhead either.
Shaye’s parents worked in the city, so we arranged to meet at Britomart one afternoon, after she got a free ride with her actual daddy into town. She was obviously nervous upon meeting in person some random guy from the internet, twice her age, who she was aware wasn’t just there for the coffee.
I approached the date carefully and respectfully so I didn’t scare her off. I knew enough about her thoughts, hobbies and interests from a week of messaging to keep the conversation flowing. After a bite to eat we went for a walk towards the Viaduct and talked some more.
I found her youthful shyness a fun challenge. Was I a predator, preying on a young gazelle fresh from the safety of high school kids? I’m not gonna lie, I did have moral doubts for a moment, but they were definitely brief. She was legal after all, and SHE had signed up to a sugar daddy website all by herself.
Moral doubts aside, when we were in a quiet spot on the waterfront, I asked Shaye if I could kiss her. She smiled back and touched my arm to say yes. First base unlocked.
Shaye never asked for money, but on the walk back through Commercial Bay we stopped into some shops. Shaye picked a perfume and a bodywash she liked. I guess receiving gifts was her love language. Did she yet know every man’s love language is physical touch? Haha. We said our goodbyes and little Shaye walked back up Queen street towards daddy’s office. As I watched her blue jeans and Glassons top walk away, I wondered if I would ever see those clothes on my bedroom floor.
The next day I was out and I got a Snap from Shaye. She was trying on some clothes with a friend at a mall. She asked me whether I liked the tight top she was trying on, cleavage showing, just below her long kissable neck, and sweet smile looking at me in the changing room mirror. Her friend was in the picture too. Smiling with a teenage grin, full set of braces showing. I shook my head thinking wtf was this fantasy I was delving in to.
I agreed to send Shaye the money for the top she just showed me, hopeful the investment would soon pay off. She agreed to let me see what I had paid for the next day. And she wanted me to see it at my house!!!
Saturday morning arrived and Shaye’s grey Nissan Primera pulled into my driveway. I had made sure to clean up the bachelor pad and change the bedsheets, ever hopeful of soiling them later that day. Shaye gave me a big hug on arrival and asked if I liked her new top. She told me to lean in and smell what I had bought her from Mecca at Commecial Bay a few days prior. Sweet heaven, is this what being a hero felt like??
Shaye sat next to me on the couch and giggled away in the afternoon sun. We were now into week 2 of messaging, second date, and a lot of snaps back and forth. She had reached comfort levels already and was following her carefree spirit. After laughing at one of my lame jokes, Shaye looked me in the eyes, jumped over to straddle me, then started kissing me.
She wasn’t an experienced kisser. They weren’t the passionate tongue teasers you get from an escort that’s paid to do this 20x a week. They were gentle, youthful, inexperienced kisses. They were nice. They were different to what a guy in my age bracket is used to.
After 20 mins of kissing, and dry grinding on the couch, Shaye asked where the bedroom was. I showed her the way and she popped into the ensuite bathroom. My heart rate was racing a lot by this point. The BPM jumped even further when Shay walked out, only in her bra and undies, with a mischievous smile on.
We went to the bed and kissed some more. Shaye helped take my own clothes off to match her own lack of fabric. “I like dad bods, the boys at school were always too skinny”. Nervous chuckles from me.
We rolled around further and my kisses moved from her lips, to her neck, to the tops of her tits still covered in a small bra, and then to her stomach and inner thighs. I could smell sweetness a few centimetres away.
I asked Shaye if I could lick her pussy. She smiled and nodded in agreement before I removed her undies. Staring back at me was what I could only describe as vaginal perfection.
18 year old, white girl pussy. No large skin flaps, a perfect inney. Completely shaved like she was not yet a woman, but plenty of stubble from inexperience at grooming down there. The light touch of her own juices at the bottom of her opening, visible in the sunlight. Slightly enlarged clit, but still nestled under its hood.
I showed her a few tricks I had learned over the years and managed to make her orgasm. No fake moaning you get from the paid companions. She was quiet as a mouse, only a small moan and muscle jerks when the little fireworks went off.
Here’s where the train of delight started to derail. The train driver wasn’t on his best game. I was failing to get hard myself. What the actual fuck!? Why was my anatomy letting me down during this moment of… unbridled teenage corruption?
A lovely 18 year old girl was in my bed, no panties on, wet as fuck and my member wasn’t performing. The pressure of the situation, combined with the absolute mismatch of age, background, and normalcy, had got to my head. Sure I had fucked girls younger than me before, but never had I had some girl so young, in my own home, in my own bed, with no clothes on before. I was actually nervous about the situation! And my dick was limp. The embarrassment of it all.
I asked Shaye if she would give me a blowjob, not letting on that this flaccid state was entirely unusual and disappointing to me. “I’ve never done blowies before, I don’t know what to do”. Oh well, this isn’t a moment for me to teach you that skill sweetheart.
We returned to laying down. I wiped my mouth and went back to kissing her, and playing with her pussy. She was so young and naive, she was just going with the flow of things. What was a personal failing of mine must has come across as gentlemanly pacing. No rushing to fuck her flower. She must have thought real men took their slow slow time!
Then I remembered something spectacular! Hidden in the depths of my glovebox was an old mostly empty pack of blue pills. Kept there for when I wanted to fuck more times than the body would naturally allow. I hadn’t used them in a year or so, but I was pretty sure at least one was left.
I made an excuse to get us both a drink and popped into the garage. Found what I needed, downed the full 100mg available, and returned to the 18 year old laying in my bed.
Every fairytale has a happy ending, and half an hour later, I was plowing my now raging erection into this young girl. I took it easy and didn’t want to completely break her pussy in. I didn’t want to her driving home so sore she never returned. But the blue magic had done the job, and I was good to keep going for quite some time!
Shaye was a young starfish. She didn’t really know what she was doing, and her inexperience did show. She told me she had had sex a few times with boyfriends during high school. But nothing serious. She told me how those boys only ever lasted a few minutes and usually couldn’t make her cum.
Shaye stayed until it got dark and she noticed a bunch of missed calls from mum. I laid next to her when she called back to say she was at a friend’s house, and she would be home soon.
Over the next few months I never did teach Shaye how to give blowies, as she called them. I was content letting this little teenage starfish lay back while I did all the work. Once or twice a week Shaye would send me videos of her trying something on with friends at the mall. I would send her whatever amount the price tag said. Shaye would come over on the weekend and show me what I had bought.
Once we went to St Lukes together and I followed behind her from shop to shop, enjoying the little fashion show, knowing that in a few hours she would be coming back to my place to let me fuck her.
It was never going to be a long term or serious thing, and in June (last month) Shaye departed with some friends for some backpacking adventures. All in all she would have parked her Primera in my drive way around a couple dozen times. Hard cash never exchanged hands, but I definitely paid for the fun that was had in other ways.
Was Shaye really 18 or was she like the 18 year olds on escort sites (meaning in her mid 20s). I definitely saw her insta posts with her friends in red-crested Mahurangi uniforms only just last year in 2024. We never used condoms, but she did assure me she was on the pill.
Shaye was a fun time for a few months that will be etched into my wank bank of memories.
