How One Message Resulted In $100K

By Steve USA

Jun 22, 2018
What if I told you an unsolicited, well-crafted initial message led to a $100,000 total value windfall arrangement for a Sugar Baby of mine?

This is a true story and it illustrates the power of a well-written and sincere (well sincere sounding anyway) message on SeekingArrangement. Pictures can catch the attention of a Sugar Daddy like me. However, a meaningful note will engage him. And in this case, it resulted in a year that netted this particular beautiful (and very smart) young lady about $100K in total value. A nice bonus on top of her entry-level administrative assistant job at a medical office.

So you might ask, how can a single message turn into $100,000?

The First Exchange

Her message arrived in my SeekingArrangement inbox out of the blue – a thoughtful and relevant note related to my profile. Maybe it was a canned message she sent every potential Sugar Daddy that caught her eye. However, it felt bespoke to me.

I immediately checked out her profile and profile picture which was only a partial face and body shot. While I could sense she was pretty, I was not overly attracted to the photo. All I could really tell was she had blond hair and was likely in her twenties. Had I been just browsing pictures, I would have likely passed on even opening her profile. But because she initiated contact I checked out her description. I  found it well written and thorough. That was and always is, very attractive to me for sure.

I responded to her note and her prompt reply was also very appreciated. We exchanged photos and she complimented mine (another nice touch). I found her photos attractive but she was still dressed modestly and I could not get a real sense of her figure.

Getting Hooked on Her

Frankly, with a lot of potential dates in the mix and a very busy schedule, I was on the fence on pursuing her. We had a little more back and forth setting up a potential first non-expectation meeting. She was charming and I was intrigued. I was busy traveling as usual and a week went by before I responded to her last message (I had mentioned that it would be a few days before I could respond due to this travel).

In my follow up note I asked how she was doing and she quickly responded: “Better now that I have heard back from you”. She had offered the bait with her first message, and this response set the hook!

That single savvy phrase sealed the deal for me. I had to meet this woman and she went to the top of my meeting priorities.

The Meet and Greet

She suggested a local bar to meet for a drink and kept in touch as the date approached. The evening we met, she was even more attractive in person and whip smart too. Again, conservatively dressed I could tell she had a nice figure but her attire still left plenty for the imagination. Drinks lead to dinner and that led to some making out and I got a taste of her sensuality. I put her in an uber home and texted her – “when can we do our first real meet?”

That happened a week later. We had a nice dinner and got to know each other better. It was fun but still just a little bit awkward. As we walked back to the hotel she took my hand. That was a very special move on her part.

Once in the room, we kissed gently. I poured her a gin and she sipped it. It was her request. I kissed her again and she stepped back and started unbuttoning her blouse.

I watched intently.


As button after button was released, she stared me in the eye with a seductive smile. I could, for the first time, see her breast cleavage and I was enamored.

Finally, I helped her take the blouse off and kissed her again while gently guiding her down on to the couch of our suite. I ran my lips down her neck and then across her bra and breasts and down to her firm tummy slowly kissing her perfect skin.

She had a skirt and heels on. I went to my knees and kissed down her leg to the cleavage of her toes and then removed her pump and placed her big toe in my mouth. She moaned and looked at me with seductive green eyes. I then undid and pulled her skirt down as she lifted her cute behind to help and took stock of her in just a lacy bra and skimpy panties.

It was then that I realized before me was one of the most beautiful women I had ever seen – and until that moment I had no idea. I also discovered a spectacularly designed tattoo on her inner thigh that ran up to her belly button. That surprised me a little, but there were many more surprises to be had in the months ahead.

Moving into Something More Serious

As we began to date, I found her attentive, intellectual, positive, gracious, grateful, funny, honest, plus grounded and mature beyond her years. And, of course, gorgeous. We did a lot together including taking amazing trips to New York, Miami, Phoenix, Las Vegas and a number of other cities. We ended up dating for about a year before she headed off to medical school.

In case you are wondering, we started off on a Pay Per Meet (PPM). That turned into a monthly allowance and random spiffs using Venmo and many fun gifts which I loved giving. After about 6 months I went exclusively with her by my choice to concentrate my time and resources with only her. And no, I did not ask her to be exclusive with me. Our arrangement even led to some other creative financing that worked out very, very well for her.

Better to Have Loved and Lost

When she left for medical school I reminded myself of Dr. Seuss saying – “don’t be sad it’s over – be happy it happened”.

So I happily went back through my financials and between first-class airfare, 5-star hotels and resorts, meals, excursions, gifts (I loved buying her gifts) and direct cash to her the total value was about $100,000. I was surprised and even taken aback by that amount but, I did not regret it whatsoever. I actually wish it could have been even more.

She brought me all the things a Sugar Daddy could ever ask for with attention, affection, friendship and fond memories that I will carry for the rest of my life.

The lesson? Write often and write well.