(Apologies, DM is closed now as I am too busy with work and not looking currently).

 Who: This post is about me and one of my FWBs.

 What: Break-Up Sex (Unless I can prove my worth for a reason to stay?)

 When: This happened about a week ago, so it's still fresh in my mind.

 Where: A beautiful hotel room with a King Size Bed in the GTA.

 Why: As the saying goes at work, different people call it different things. It may be “lessons learned,” a “hot wash,” “introspection,” or “retrospection” (yes, if you are in one of those Agile / DevOps type shops, hehe 😊). But in r2rToronto, I suppose you would call this a success story.

 

 And the story begins here ...

“Daddy”

 I am no stranger to Reddit for asking random questions, but the concepts of personals and hook-ups were completely new to me until about five months ago. After this discovery (born out of disappointment and failing relationships), I met my first Redditor IRL, whom I will call “Daddy.”

 

“Daddy” is actually younger than I am, but because of the dominance he exerted over me, I loved to worship and fear him. One of the first few pictures he shared with me showed him holding a paddle, and another holding a belt. This put me—a submissive and a brat—into instant drooling mode.

 

Pre-Meet

 “Daddy” and I had been chatting a lot and hooked up a few times until he decided we were looking for completely different things and daddy wanted to break it off (to my disappointment).

 

I came to realize that “moving on” is involuntary and inevitable, but I wanted to have one last rendezvous on my own terms. It was late Monday night when I told him how sad I felt about where things were going and asked if we could meet up again—perhaps for one last time. He granted my wish. Immediately, I decided to book a hotel. He was surprised by how quickly I moved ahead and needed to check if he had any work meetings on Wednesday. While waiting for his confirmation, I looked through my collection of toys to decide what to pack for this “staycation.”

  

The Meet

 On Wednesday afternoon, after some delays with work, I was able to trek on the bus and walk to the hotel with my treasure trove. As soon as I walked into the room, I was so excited by how it looked (with a separate seating and bedroom area) that I sent pictures back to Daddy. I took a shower and put on nice lingerie with a short skirt over it. I proceeded to lay out all my toys (paddle, flogger, cuffs, vibrators, mask, etc.) neatly onto the bedside bench.

 

I was almost ready to go down to the lobby in my high heels when Daddy came to the door around 7 PM (we surprised each other). Since Daddy loves swimming, I asked him if he wanted to use the hotel amenities first before we got into our acts. Daddy was just as horny as I was. After giving me a hug and pinching my butt cheek, he took a quick shower and we went straight to the bedroom.

  

The Sex…

  

Part 1 – Teasing with the Toys

 This was the first time Daddy saw that I had brought all these toys. Immediately, he pushed me onto the bed face down. Daddy put the wrist cuffs on me and made me cross my arms behind my back. He then had me bend my legs with my feet up, kind of like a hogtie without the spreader bar. After inspecting the implements, Daddy stuffed my pussy with a pink vibrator, and after glistening my chrysanthemum with some lube, he inserted a blue butt plug into my tight space. Immediately, I felt exhilarated but fearful at the same time.

 

Daddy then proceeded to hit me with the paddle, then with the flogger, and then with the riding crop. I was screaming for Daddy, my butt cheeks turning red, the soles of my feet twitching a little, and my thighs worrying whether they would come between the instruments or Daddy’s dick.

 

Daddy was holding the riding crop so hard that the feathers at the handle all fell off (a shame, I just bought this toy lol). I did not get any tickles or light teasing; instead, the whole time, I was moaning and yelping like a puppy, begging for Daddy. Begging for him to hit me, this little slut, this little bad girl. As I confessed to Daddy and asked him what I should do, Daddy "DP'd" me by pulling the butt plug and the vibrator in and out in tandem. I was so excited. My ass rose up and down, waiting for him to spank me again.

  

Part 2 – Monster Cock

 Daddy has an 8-inch, girthy, uncut cock that would make any tiny woman feel fearful if they had never tried one before. While I still had my wrists bound and my legs up in the air, Daddy made me “bow” and held my head to assist in worshipping his dick by bobbing up and down. Daddy had me start licking him, pleasuring the tip of his head and the frenulum, licking up, down, and around the shaft like my favorite lollipop, and then licking his balls. Daddy smelled of fresh bubble bath and virility. When I did well, Daddy would praise me. But I enjoyed it even more when Daddy spanked me while I was sucking him. He made me bring my feet together so that my butt would be pushed out and even meatier for spanking.

 

Daddy gave me a break and released my wrist cuffs so that I could hold his dick while going tabletop in front of him. Daddy fondled my breasts and twisted my nipples (my favorite tease) while I continued to suck his dick and get flogged. I was wearing a submission mask, so I couldn't see how pleased Daddy was; I just had to rely on his spanks and praises.

 

After a short tease, Daddy was ready to let me ride his cock. I carefully rolled the condom onto his huge cock (his foreskin was now peeled back, revealing the plum, flushed head), and I lowered myself cowgirl-style onto this handsome man. I tried going up and down a little but eventually changed to a rocking motion back and forth. Daddy was squeezing my small boobs and slapping them, driving me to rock even harder. As I started getting tired, I gripped the headboard with both arms so that I could fuck Daddy hard. Even though Daddy didn't have time to work out with me in the gym, I felt like I was getting a full-body workout.

 

Daddy wasn't satisfied with the front view, so next, I did reverse cowgirl. With the butt plug still intact, I turned around and sat on his cock. I knew I hadn't been doing enough squats and glute exercises, which is why Daddy made me practice hard, slapping my ass when I didn't go fast enough. Thank you, Daddy.

 

Finally, Daddy was ready to show me who was boss. He made me bend down with my ass sticking up so that we could enjoy doggy style. Daddy proceeded to ram his cock into me while I rubbed my clit and begged for more. Knowing my clit was getting bigger and my tasty lips were engorged and plump, he removed my hands, made me squeeze my cunt harder, and—with his hands grabbing my butt cheeks—rocked me back and forth even more so I could enjoy the full depth of his cock while begging and moaning.

  

Part 3 - The Finale

 Daddy figured we both needed a slow treat, so he lay on his back, half-seated, with his beautiful cock pointing to the sky. I proceeded to lick his cock all over while wearing my submissive hood, so all Daddy could see were my slutty, luscious lips ferociously licking his cock and balls, sticking out my tongue like a helpless puppy to catch every drop of pre-cum.

 

Daddy and I enjoyed this quiet moment a lot, so instead of loud slapping, he rewarded me by grabbing my boobs and twisting my nipples. My nipples are like joysticks that respond to pressure and the right amount of twisting; they were flushed with blood, getting harder and darker. Even without a dildo or cock inside me at that moment, I could just imagine how amazing it would feel if there were one.

 

Finally, Daddy rewarded me with spanking again. He made me go doggy style, face down, ass up. My ass was getting so red and blushed by the riding crop, and my moaning grew louder. I told Daddy, “Please spank me, I am a fucking whore… yes Daddy, yes Daddy, please…” Daddy rocked his cock even harder while my butt plug remained intact, making me feel so stimulated and wishing I had brought a thicker plug.

 

Finally, Daddy made me go back to sucking him. As I licked more and played with his balls and perineum, Daddy was about to come. Without me even trying too hard, squeezing, or twisting, Daddy exploded inside my mouth with his full load of cum. I felt like a satisfied slut. I was fed. Once Daddy regained his composure, I came up to put my breasts around his mouth so he could suck on my nipples, making me feel like a worthy slut who received a gentle closure.

 

Post-Sex

 I had already brought some takeout from the fridge with Daddy’s favorite food, ready to reheat in the microwave. Daddy figured I was such a hardworking slut that he needed to top up the takeout with some more fast food. We enjoyed the food, had our small talk, and channel-surfed a little. Daddy is an avid movie watcher and noticed a movie with Matt Damon and Chinese stars, whereas I know nothing about movies. The night was getting late and Daddy needed to wrap up some work, so he proceeded to enjoy his office desk and chair with his laptop (yes, I feel like that’s the perfect nerd setup with the TV and couch all in close proximity, a perfect Man Cave), while I went to the sleeping alcove.

 

The Morning After

 To my surprise, Daddy and I did not have a chance to go for a morning round. Daddy had his alarm set for 6:15 AM or so with no time to snooze. He got up and ran right into work meetings. Given the white noise of his work meeting (even though it wasn't too loud), I couldn't fall back to sleep. So, I got up with my laptop and worked a little bit after I showered and enjoyed the steam and bath gels. Unfortunately, due to his meetings and business, neither of us got to try the jetted tub, which I thought would be a treat for Daddy. We went according to plan with breakfast around 9 AM, and then shortly after, we checked out and went our separate ways once Daddy dropped me off at the bus stop.

 

What I Learned (In No Particular Order):

 

1. I still have a hard time separating my upbringing from coming to grips with my sexuality and enjoying BDSM. During this whole experience, I realized I truly enjoy spanking, crying, and feeling helpless (when done right—neither too light nor excruciatingly painful). I turned all my silence into actual cries and yelps, and it had a wonderful cathartic effect.

2. My sexual desire is sometimes fulfilled just by watching, imagining, and writing down the experience. The idea of planning what to bring, the journey getting there, and the moments spent waiting—from the hotel booking to getting naked—is just as important as the sex itself.

3. I am not good at deep throating. The position where I am perpendicular to the guy with my head thrown back while he drives his cock into my throat... while that view is beautiful for the guy, I haven’t been able to cope with the gag reflex.

4. I have always hated breaking up with people and have a hard time facing rejection. It felt like, at least for the first time, I could actually talk about it and plan around it a little more than I did in the past.

5. I snore when I sleep. I didn’t know I did that, but now someone has proof. Maybe I should go to a sleep clinic and see if I need a CPAP machine.

6. After this whole experience, I realized my desire to get back with my ex and the attachments I felt were all smoke and mirrors. It was like… I was hungry, and then I was no longer hungry. I can finally be at peace and focus on myself, my work, other pleasures, and new adventures.

7. I consider this meetup to be a 90% success, but it could still be better. For instance, maybe I could be more prepared for Daddy and bring the right supplies. If I knew the room was going to be so big, we could potentially plan for group play and bring in another couple(s). I also could have talked more about what I wanted for my own pleasure—for example, I enjoy nipple play, being caressed, and perhaps receiving oral. But I felt like this time I put so much focus on just being a good submissive for my Daddy, u/friendanni (tagged with his permission) , because this may be the last time I see him IRL.

 

Now please share your lessons learned and thank you for reading! Appreciate gentle comments and constructive criticism too and sorry again I cannot take any DM. 😊

Hi there, I visited a lifestyle club yesterday and 4 cute South Asian guys were chatting me up. Unfortunately, the prospect of playing with someone so young felt a little weird with me and it was also getting close to home time. So we had a good rapport but nothing steamy beyond that.

They said they are around 25 years old, working professionals, some have been living in Toronto for a few years now, but some less time. Most importantly they are all looking for play but didn't have much luck.

They are in the same field of work as me, and a newcomer also, so naturally I feel a little sympathetic for their struggles ( as I was once like them years ago).

I asked them if they know about Reddit personals and they seem to not know anything about it.

Appreciate any comments or suggestions on, how to introduce them to this sub, and if there is any good template to follow in order to create a good bio draw more invites?

Thank you so much.