[F]rom Instant [M]essaging to Spanking and Fucking – Part 2!

[Part 1](https://www.reddit.com/r/gonewildstories/comments/jzoc7u/from_instant_message_to_sexting_and_coffee_date/) .

Don’t worry, it gets dirty quickly:

One of the first things I like to do with a new partner is communicate. After we decided to get a hotel on that park bench and I knew sexy stuff was coming, I started asking her about what she liked. It was clear already from our flirting and sexting that she was a kinky submissive baby, albeit inexperienced, and she was very drawn to me as an older, dominant Daddy. The photographer and professor bit helped too;) To be clear everyone, especially guys, nothing is sexier than consent.

She was uncharacteristically shy about telling me what she wanted so I told her let me tell you what I want to do and stop me if anything gives you pause. So I told her a story and she visibly squirmed in her seat as she imagined me about to do what I was saying. After about 10 minutes she got over her shyness and she said, “Daddy, you need to stop talking now and start going down that fucking list.”

[F]rom Instant [M]essage to Sexting and Coffee Date.

I was scrolling through my Instagram feed the other day and stopped on a profile suggested to me by the algorithm of a beautiful young model. As a photographer this isn’t unusual, I tend to get a lot of suggestions based on photography, art and dogs. I love dogs.

What was different this time was that I spent an inordinate amount of time on her profile, not just looking at her sexy photos but the style as well. The photos were all quite artistic beyond the rather boring fashion stuff one sees all the time. I soon discovered they were all self-portraits. I clicked on her story of the BTS of her shoots and was very intrigued. I moved on and was doing other things when I got an instant message. I had followed her feed and I guess she also saw that I was viewing her story.

She had viewed my photos and showered me with compliments, I in turn complimented both her work and beauty. I was rather effusive and we went back and forth for a couple days. Eventually I asked if I could photograph her. And I know, I am sure she gets tons of older photographers hounding her constantly but one never knows and one never knows if one never asks.

Wife in the morning, Babygirl in the afternoon [MF][MF]

Yes, my wife knows, she loves to see the photos I take… And no, I didn’t fuck them at the same time. I started sugaring mainly because the Mrs likes to watch and I like women younger than myself, my wife is 10 years my junior.

Anyway, when she knows I will be seeing my bby, she gets super horny. She doesn’t come and watch much anymore but Loves the idea of what I am doing. I am truly lucky.

So last weekend she knew I was going to see my baby and she woke me up in the morning with her mouth on my cock. I am 48 and cumming more than twice in one day is not as easy as it used to be. But we are very sexually compatible, even after 15 years. I came down her throat and she slowly licked everything up that escaped. She then smiled at me and told me to have a nice afternoon.

That afternoon I met my baby at a hotel in NYC for our normal afternoon of fucking and play. We usually spend 2 or 3 hours together and like I said, if I can cum 3 times it’s a good, good day. She really likes to get me there and sees it as a personal challenge, especially since the 3rd one takes some work.

Happy Ending [MF]

I used to go to this amazing massage place in Manhattan. It was quite upscale and the women actually gave you a massage before the happy ending. It was around the corner from the train station and about once a week I would treat myself during lunch. I have gone to places like this off and on for some time now, a nice hand job is often just the thing one needs.

Usually the salon posts on their blog who is available, with photos and times. I loved calling up and just saying, “give me someone petite”. I loved the unknown element. Sometimes it was better than others but very rarely did I ever leave thinking it was a terrible hand job.

One time I met “jane”. She was an actual American college student, not an eastern European woman pretending to be a college student or a girl next door. She was brunette and petite as well as very chatty. We hit it off immediately. We talked about a lot of things, mostly sexual stuff. She told me all about being head hunted for the place in a coffee shop, and that at first she was very suspicious. But she soon grew to really like it and the money. I told her about my life as well and the first time I told her about my sugar dating she just stopped and looked at me.

This never happens but it happened to me…twice [FM]

You read a lot of college student/professor things here and I am sure a lot of it is far fetched. Except for mine of course:) I have been an adjunct professor for 15 years now at two different schools and although there are often sparks of interest, professors are really, really afraid of loosing their jobs for anything seemingly inappropriate. I no longer have an office to myself, we have to share so that there is never anyone alone with a student. It certainly makes this popular fantasy harder to realize for most I would assume. Almost 10 years ago [this](http://reddit.com/r/gonewildstories/comments/f1ubz6/propositioned_by_a_student_and_i_said_yes_fm/) happened with a former student, That was the first time. The second time was this past weekend…

One school I work at is back in person, sort of. A hybrid system with students in the dorms and living in town. Office hours and most classes are now conducted by Zoom and Google Duo. But I teach art and sometimes there is no substitute for in-person meetings. One of my critique classes is meeting in person, socially distanced, and it’s going pretty well so far.

My Masseuse asked me to spank her and be my Sub [FM]

I know what you are thinking, this is not a story from one of those “massage parlors”, although, I have a couple of good stories about those, too;) No, this was something organic that happened with an actual massage therapist I had been using for back pain. Read on… This might be a long set up, so skip to the ***** marker below if you just want to read the juicy bits.

A few years back I started going to a legit spa in my manhattan neighborhood for lower back spasms. I had a couple different therapists work on my back and then I met A. She was my 3rd therapist at this spa and after meeting her I requested only her, and eventually she started making office/house calls.

A was petite but strong, I remember being impressed at how good her technique was for such a small woman. She was about 5′ 2″ or so and maybe 100 lbs or so. Anyway, she was and probably is still, a very good massage therapist. I saw her professionally about once a week for 6 months and then non professionally about once a week for another 4 or 5 months. I wish it had lasted longer but I love the memories of what we had.

A [F]ormer student of [M]ine

Yesterday, out of the blue, a former student of mine texted and asked if I still had office hours. I haven’t talked to her in a long time. Years. She is moving back to NYC soon and wanted to know if I was interested in private tutoring. LOL. Stay tuned.

[MF] Fucked my Sugar Baby in the back of my minivan

Quarantine be dammed, picked her up and parked near the woods. She got on your hands and knees in the back, pulled her skirt up, showed me the plug she had in already and said, “Take out my princess plug Daddy and put your cock in”. So I did:) It was a quick, intense fuck and after I came she put my dick in her mouth to clean me off. She is so dirty. Then I took her home.

F27/M48

My Sugar Baby Threesome [FFM]

[F20/F21/M45]

A couple of years ago in between sugar relationships I signed up for SA again and started the huge process of weeding out crazies and pros to find possible SBs. Usually it takes a few weeks of constant messaging and possible meet and greets to find potential babies. I had been chatting with a woman that I liked and seemed to like me too, so we picked a day and time to meet for coffee.

We decided to meet at a hip coffee shop in the Chelsea neighborhood of Manhattan. I got there early, secured a good table and waited for her to show up. She was 20 and quite petite, a mix of white, black and american indian gave her amazing coloring and long, straight black hair. I saw her walk in of course but she was with someone and she was holding her hand! Although it’s never happened to me before, I had heard some women always brought a friend to the first meeting for safety but this was a new one. She said hello and then introduced me to her girlfriend saying, I figured since you two might be sharing me I wanted us all to meet. Her girlfriend said hello, they sat down and I ordered us all coffee as we started chatting. They were so lovely and cute together and we ended up chatting about NY and Seeking Arrangement and Art School for over an hour. Her girlfriend, a slightly taller and older blonde woman asked me a lot of logistical questions about the proposed arrangement and clearly liked the idea of her girlfriend having a sugar daddy.

The famous actress I met on a sugaring site [M][F]

To be fair, she wasn’t famous at the time…. not yet. She was in her early 20s and had a supporting role in a Broadway Show. I had signed up for Whatsyourprice, the smaller sister site owned my Seekingarrangement.

She messaged me and asked for an amount for a Meet and Greet first date and I accepted. We made a plan and started messaging each other on KIK as our coffee date wasn’t for a few days.

Long story short… She had/has a thing for funny, dominant older men, and I fit the bill. We clicked so well that while we were having coffee she asked me to get a hotel room so I could fuck her.

And fuck we did. From the moment we got into the hotel room she was insatiable. She was Really, really turned on by the naughty secret of doing what she was doing.

Over the next few weeks I would get a room in Times Sq and we would meet during her breaks. It was a whirlwind that I knew would end as her show was a limited engagement and then she was back to LA.