Author: HBG_SD

Nerdy MILF [MF]

In between sugar flings, I got bored and decided to try my luck on Hinge. After a few days I matched with a cute, nerdy MILF who was a couple years younger than me. She was about 5’4 with reddish brown hair and a slender frame. Her profile made it clear how nerdy she was – waited in line for the 1st showing of every Marvel movie, loved to cosplay and preferred hard sci-fi novels. I’m not going to lie, the cosplay pics on her profile (don’t ask me to name the characters she dressed up as!) were the deciding factor that led me to message her.

My initial message led to some innocent flirting, and by the end of the day I had her number and a date set for a few days letter at a local wine bar. Wine and appetizers was the plan, but we stayed for dinner because the spark was obvious from the start. Before I knew it, the staff was putting chairs on top of tables in a subtle hint that it was time to leave. Read more »

Colombian/Brazilian Escort [MF]

As I mentioned in my first post, before switching to the sugar lifestyle, I would occasionally hire escorts. I had come across a website for an agency that advertised latina escorts. When I saw Sheila’s profile I was hooked. Dyed blonde hair, 5’5, big perky fake tits and a perfectly round ass. Each girl’s schedule was located on the profile. I had to wait a few months for her to pass through my city, but when she did, I was quick to reserve my spot (if you ever book with a traveling pro, best to take their first appointment slot).

On the day of our appointment, I was so excited I could barely focus at work. I made an excuse after lunch and left early. Instead of going home to deal with my “headache”, I went straight to the nice hotel downtown. I texted the middleman and was given Sheila’s room number. Now at this point I was fairly new to nice hotels and was totally unaware that only certain elevators would go to certain floors and key cards were needed to access the top floors. After a few befuddled minutes, I texted that I was stumped by the elevators and was told Sheila would be down to get me. Sure enough, a few minutes later the elevator doors opened and my jaw dropped as I laid eyes on Sheila in person for the 1st time. She was just wearing jeans and a shirt, but my god was she gorgeous. Read more »

Two Sugar Babies in 1 day [MF]

I had just started seeing Caitlin a few weeks before. She was 22, blonde, 5’7 and had the best ass I have ever seen (Top 3 – Caitlin, Erika, Rose…stories on the last 2 are upcoming). It was clear she did squats daily. She was a little more transaction than I usually like, but I forgot about all that when she bent over in front of me. Plus she liked it rough. Not spank me a little rough, but spit in my face and call me a whore rough.

Caitlin was due to come over for a lunch date in a few days, when I got a text from Jenny. She was also 22, but was brunette. She had perfectly perky B cups and a nice fat ass (probably #4). Jenny was making a trip home from college and wanted to hook up. We had spent the summer fucking at least once a week and I really wanted to see her. She was only available the same day as my date with Caitlin. I considered cancelling with Caitlin, but said fuck it, why not fuck both? Read more »

Will travel for creampie [MF]

At the time I met Emily, I was 31 and she was 21. I was having a trouble finding a suitable sugar baby in my area so I widened my search area. I am about 90 minutes from a major state university and figured if I want to fuck a college girl, go where they are. My search resulted in a lot of good candidates, but I picked Emily. I’m a sucker for girls with dirty blonde hair and curves. We made plans for the following week. She didn’t want to risk being seen out with an older guy, so she suggested just getting a hotel room. I did not hate that plan.

When the night came, I drove up to the college town and checked into the hotel. I texted her to see if she was ready and she replied with her address. When I got there, I parked and saw her walk out of her front door. God damn, I was in for a good night. She was all done up and wearing a tight black dress. She got in the passenger seat and her dress rode up revealing her toned thighs. Normally when I take girls to hotels, I try to use side entrances to avoid prying eyes, but this time I proudly paraded Emily through the lobby to the elevator. The front desk attendant gave me a “I know what that is” look, while the guy checking in gave me a “you lucky motherfucker” look. I just smiled and hit the up arrow. Read more »

Taking my sugar baby’s anal cherry [MF]

My last post was about my first sugar baby, this one is about my current one. We’ll call her Georgia. She is a hippie-ish white girl with wild blonde hair and a slender build. We had already been on a few dates that I really enjoyed.

When she got to my house, I practically jumped on her as soon as she entered the door. I was in a mood and she was looking great as always. I threw her bag down and rushed her up the stairs to my room. We kissed as I pushed her back on my bed. She seemed to feed off my energy and her clothes were off in no time. I moved her to the edge of the bed, knelt down and started eating her delicious little pussy. I slid a finger in as well. My tongue and finger worked together to make her moan and squirm until I finally felt her cum. With her satisfied, I stood up, freed my cock and got it lined up. Georgia is a good girl and lets her daddy fuck her raw. She gets super wet, but is so tight, I still have to patiently push into her. Once I finally got balls deep, I grabbed her legs, held them against my chest and proceed to give her little pussy a good pounding. I hadn’t cum in a few days and I knew I had a big load to release. When I got close I pulled out and starting shooting. The first two ropes of cum hit her right on her chin, which took us both by surprise. She took it like a champ though, and laughed it off as I got a towel to clean her up. Read more »