Sugar Daddy Diaries - Kelsey the single mum
- Jul 3, 2025
- 8
- 46
- 13
I’m a year into a sugar dating experiment and it’s fucking fun. You can’t easily tell your mates you are paying to shag girls off the internet, so maybe the SF gents are interested in the experiences.
I’ll try to break these up into instalments. If you don’t like what I’ve got to say, just know I’m doing this for my own titillation more than yours. Make of it as you wish!
Instalment #1 - Kelsey, the single mum
My first sugar baby experience was with a young single mum, living in West Auckland. Kiwi girl, mid to late 20s, with two school aged kids to different baby daddies.
Why sugar dating? I’m mid 30s with a pretty successful professional life. I found out a long time ago that sex was the best drug around, but I was not made for boring monogamy.
I read a post online where someone said sugar daddy websites were better than escort websites. Why not give it a go? After all, I must have spent a small fortunate on escorts over the years. By the hour interactions were becoming old.
I’m not Brad Pitt, and I haven’t seen a gym in a decade. But I’m likeable enough, average build, with sufficient possessions that a young girl in Auckland would think makes you wealthy. House in leafy suburb, modern European car, small boat, nice clothes. Not fuck off money though. Maybe these sugar baby girls might be fun?
After signing up to Sugar Daddy Meet and messaging a few prospects it became plain that this was more admin heavy than I thought. But what the hell, nothing like putting your sales background to good use.
I stumbled upon Kelsey’s profile. We messaged back and forth on the website for a day or two before we changed to Kik, that app that all the cool girls use.
Kelsey was easy to talk to, but unsure of herself in this sugar dating world. She wanted to earn some money to help her kids, and sounded like she enjoyed sex. Her story was one of failed baby daddy relationships that locked her into single mother poverty. She didn’t want to be an escort, but a friend told her sugar dating was an option. She did nails on the side from home, but I guess our taxes funded the rest.
Kelsey could hold a conversation and the back and forth flowed, so we eventually decided to meet, all the way out in Muriwai. This was about 10 days in to messaging, and several phone calls deep. I had not seen a real photo of her yet.
When I arrived at the beach and looked around, I saw this hourglass figured blonde girl standing where we were supposed to meet. Beautiful dress, nice long blonde hair, excellent make up, smelled good. Why the fuck was this lady not being hit on by every guy in a bar? Single mums don’t go to bars after school, that’s why.
We discussed the arrangements while walking along the beach. All she wanted was $300/week to “help her kids out” and she wanted to meet up once a week. She liked our messaging and didn’t mind keeping in contact. She was almost apologetic in asking for money.
A few days later after her kids went to school, I arrived at her small 3 bedroom home near Muriwai for our first home visit. She greeted me again in a hot dress, short, tight and looking flawless again. Most escorts don’t bother with this much effort.
To cut a long story short we moved from talking on the couch to the bedroom within an hour. She had a great body and almost no evidence of having kids. Maybe the odd mark, but otherwise a wow body! Reasonable tits, not overly sagged, great curved ass. Excellent.
We fucked about 3 times during the day in what felt like some teenage passion. She told me she hadn’t had proper sex since her youngest’s daddy walked out a year ago. Kelsey was making up for lost time.
Kelsey knew how to fuck, she really went all in bringing my cock back to life for each round, and she didn’t have a condom in sight. Pull out method seemed to be her go to, but I could tell that probably wasn’t fool proof for her. Failed at least twice before it seemed!!
Over the course of two months Kelsey and I went from once a week to twice a week. Always a good four hours of romp and laughter before the school bell rang. We broke her bed one time, so I paid for an upgrade from warehouse bed to farmers bed. She was fun and I felt like a 20 year old stud again. Well a stud that now had two decades experience working my way around a woman’s body.
In month 3 Kelsey was becoming more and more attached. I was too. Afternoon fuck sessions graduated to the first overnight stay. At mine this time while grandma baby sat at Muriwai. It was nice, flowed easy and felt good.
Then it hit. Reality set in. Kelsey no longer saw this as pay to play and she was locking in. We were mid fuck, heavy breathing, ball slapping, wet bodies going hard. “Don’t pull out. Cum inside me this time baby. I want you to.”
Fuck.
Fuck.
I wasn’t about to let a good bang go to waste, but I decided to enjoy watching her tits get smeared with my white love another time. Baby daddy #3 life was not for me.
Another few weeks passed and I knew the end was in sight. The deal was sealed one night when Kelsey had made herself free again (thanks Muriwai grandma) but I was already engaged. Why pay the sugar daddy site subscriptions if you just stick to one girl??
I finished dinner that night with a lady (to be glorified in a future instalment) to find a stream of messages from Kelsey, upset that I hadn’t made the time for her. The full transition from hot sugar baby to future crazy ex was complete.
I tidily let Kelsey down and cut the strings that were becoming attached more than desired. A beautiful young lady that could satisfy almost any man. Becoming a step dad just wasn’t part of the plan.
My first experience with sugar dating was bliss. At times I had to pinch myself and remember I was fucking a hot young lady, 12 years younger than me, on a regular basis, more passionately and lovingly than any escort I had ever met, and all for only a few hundred dollars a week.
I was hooked. I am still hooked. The journey was just beginning.
I’ll try to break these up into instalments. If you don’t like what I’ve got to say, just know I’m doing this for my own titillation more than yours. Make of it as you wish!
Instalment #1 - Kelsey, the single mum
My first sugar baby experience was with a young single mum, living in West Auckland. Kiwi girl, mid to late 20s, with two school aged kids to different baby daddies.
Why sugar dating? I’m mid 30s with a pretty successful professional life. I found out a long time ago that sex was the best drug around, but I was not made for boring monogamy.
I read a post online where someone said sugar daddy websites were better than escort websites. Why not give it a go? After all, I must have spent a small fortunate on escorts over the years. By the hour interactions were becoming old.
I’m not Brad Pitt, and I haven’t seen a gym in a decade. But I’m likeable enough, average build, with sufficient possessions that a young girl in Auckland would think makes you wealthy. House in leafy suburb, modern European car, small boat, nice clothes. Not fuck off money though. Maybe these sugar baby girls might be fun?
After signing up to Sugar Daddy Meet and messaging a few prospects it became plain that this was more admin heavy than I thought. But what the hell, nothing like putting your sales background to good use.
I stumbled upon Kelsey’s profile. We messaged back and forth on the website for a day or two before we changed to Kik, that app that all the cool girls use.
Kelsey was easy to talk to, but unsure of herself in this sugar dating world. She wanted to earn some money to help her kids, and sounded like she enjoyed sex. Her story was one of failed baby daddy relationships that locked her into single mother poverty. She didn’t want to be an escort, but a friend told her sugar dating was an option. She did nails on the side from home, but I guess our taxes funded the rest.
Kelsey could hold a conversation and the back and forth flowed, so we eventually decided to meet, all the way out in Muriwai. This was about 10 days in to messaging, and several phone calls deep. I had not seen a real photo of her yet.
When I arrived at the beach and looked around, I saw this hourglass figured blonde girl standing where we were supposed to meet. Beautiful dress, nice long blonde hair, excellent make up, smelled good. Why the fuck was this lady not being hit on by every guy in a bar? Single mums don’t go to bars after school, that’s why.
We discussed the arrangements while walking along the beach. All she wanted was $300/week to “help her kids out” and she wanted to meet up once a week. She liked our messaging and didn’t mind keeping in contact. She was almost apologetic in asking for money.
A few days later after her kids went to school, I arrived at her small 3 bedroom home near Muriwai for our first home visit. She greeted me again in a hot dress, short, tight and looking flawless again. Most escorts don’t bother with this much effort.
To cut a long story short we moved from talking on the couch to the bedroom within an hour. She had a great body and almost no evidence of having kids. Maybe the odd mark, but otherwise a wow body! Reasonable tits, not overly sagged, great curved ass. Excellent.
We fucked about 3 times during the day in what felt like some teenage passion. She told me she hadn’t had proper sex since her youngest’s daddy walked out a year ago. Kelsey was making up for lost time.
Kelsey knew how to fuck, she really went all in bringing my cock back to life for each round, and she didn’t have a condom in sight. Pull out method seemed to be her go to, but I could tell that probably wasn’t fool proof for her. Failed at least twice before it seemed!!
Over the course of two months Kelsey and I went from once a week to twice a week. Always a good four hours of romp and laughter before the school bell rang. We broke her bed one time, so I paid for an upgrade from warehouse bed to farmers bed. She was fun and I felt like a 20 year old stud again. Well a stud that now had two decades experience working my way around a woman’s body.
In month 3 Kelsey was becoming more and more attached. I was too. Afternoon fuck sessions graduated to the first overnight stay. At mine this time while grandma baby sat at Muriwai. It was nice, flowed easy and felt good.
Then it hit. Reality set in. Kelsey no longer saw this as pay to play and she was locking in. We were mid fuck, heavy breathing, ball slapping, wet bodies going hard. “Don’t pull out. Cum inside me this time baby. I want you to.”
Fuck.
Fuck.
I wasn’t about to let a good bang go to waste, but I decided to enjoy watching her tits get smeared with my white love another time. Baby daddy #3 life was not for me.
Another few weeks passed and I knew the end was in sight. The deal was sealed one night when Kelsey had made herself free again (thanks Muriwai grandma) but I was already engaged. Why pay the sugar daddy site subscriptions if you just stick to one girl??
I finished dinner that night with a lady (to be glorified in a future instalment) to find a stream of messages from Kelsey, upset that I hadn’t made the time for her. The full transition from hot sugar baby to future crazy ex was complete.
I tidily let Kelsey down and cut the strings that were becoming attached more than desired. A beautiful young lady that could satisfy almost any man. Becoming a step dad just wasn’t part of the plan.
My first experience with sugar dating was bliss. At times I had to pinch myself and remember I was fucking a hot young lady, 12 years younger than me, on a regular basis, more passionately and lovingly than any escort I had ever met, and all for only a few hundred dollars a week.
I was hooked. I am still hooked. The journey was just beginning.
Last edited:
