Dive into this bold episode of "Late Night with Sylvester" titled "Yes, Daddy," where I share insights from my day and my complex feelings about oral sex—navigating the love-hate dynamics of intimacy. Additionally, I recount a striking interaction with a woman on 34th Street earlier this year, highlighting everyday life's unpredictability and raw h…

Join me on today's episode of "Late Night with Sylvester." I open up about a familiar frustration—recruiters not taking the time to read resumes thoroughly. I also reflect on a challenging therapy session that heightened my sensitivities, offering a glimpse into my personal growth journey. Plus, we dive into a more intimate discussion on the dynami…

In this fresh episode of Late Night with Sylvester, I dive into the ups and downs of my day and why I'm craving a getaway. I also chat about embracing my inner 'bad bitch'—a journey of confidence and self-expression. I'll take you back to the fun and food at our June BBQ with friends, sharing some memorable moments. Join me as we unwind, laugh, and…

In this episode of "Late Night with Sylvester," I'm saying goodbye to the Jerrod Carmichael show on Max. I'll share my take on Jerrod's influence and what his comedy has brought to our screens. We're also tackling the big news of President Biden stepping down—what this means for us and what's ahead. Plus, I discuss why I choose to steer clear of an…

In this episode of "Late Night with Sylvester," we delve into the political arena as I discuss Kamala Harris and her potential presidential run. What does this mean for us, and what can we expect? Plus, I share a personal story about a recent interaction with a close friend, sparking a conversation about boundaries and self-awareness. Was I overrea…

This episode of "Late Night with Sylvester" takes a comedic turn as I share a funny story about a recent interaction I had with a 25-year-old. We’ll laugh over the quirks and surprises of being 25, reflecting on how times have changed—or maybe haven't changed at all! Join me for a light-hearted look back at youth, filled with chuckles and a bit of …

Tune into this episode of "Late Night with Sylvester" as I gear up for the upcoming debates and highlight the importance of your vote. We all need to engage and help shape our future! I also dive into the enduring love connection between Martin and Gina from Martin Lawrence's iconic show. Don’t forget to subscribe, Like, and give me my 10’s in the …

Join me for a roller-coaster of emotions on this "Late Night with Sylvester" episode as we dive into the quirky YouTube show 'Full of Love or Pop the Balloon.' Watching live audience reactions and candid judgments was hilarious and nerve-wracking. We'll also discuss Jerrod Carmichael's comedic brilliance, sharing some standout moments from his perf…

Hey, late-night fam! Big shoutout to each of you for stopping by and tuning in to another episode of "Late Night with Sylvester." Happy Valentine’s Day, everyone! Tonight, I just wanted to come and chop it up with you guys, share some laughs, and spread the love. On a more serious note, I want to address something important. If anyone out there is …

Thank you for stopping by and listening to another episode of Late Night with Sylvester. I open up about my journey with Daddy W. But that's not all – a special shoutout to Magic Mind for sending over some incredible products! Tune in to discover more about the exciting goodies. Don’t forget to subscribe, Like, and give me my 10’s in the comments! …

Happy Birthday to ME!

Thank you for stopping by and listening to another episode of Late Night with Sylvester. Joined by the fabulous Derrion (x: @_imbluntsmokeme), we're diving headfirst into the New Year, sharing the deets on my upcoming 34th birthday, and spilling the tea on a recent s**party adventure. And hey, in true late-night fashion, we're also getting real abo…

It's all about the Pink Friday vibes! 🎀 So, buckle up as I take you on a journey through the past couple of months. From the chaos of moving into my new apartment to the unexpected plot twist of getting laid off, it's been a rollercoaster ride, to say the least. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSyl…

Welcome back to another captivating episode of 'Late Night with Sylvester.' In this episode, we embark on a thought-provoking journey through the ever-evolving realm of sexual health, delving into the shifting narrative surrounding gay men engaging in consensual encounters at parties. PrEP (Pre-Exposure Prophylaxis) and its transformative impact on…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. In this episode, we find ourselves talking randomly about a few things. We talked about my situation that I got going on with Shawty and Heavy. I went to Dallas for the weekend to turn up and get away. I hope you enjoy it! Don’t forget to subscribe, Like and gi…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. In this episode, we delve into the world of single parenting in the U.S. Explore the realities of juggling work, childcare, and personal well-being, while uncovering the policy support available. Shout out to all the women and single parents! I'm still very muc…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode I talk about the iconic show Sex in the City. I'm celebrating all the "Samantha's" out there! This episode is dedicated to empowering and giving a special shout-out to every strong, independent, and adventurous Samantha in the world. I talk about f…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode, I talk about my trip to Dallas, TX for the Juneteenth and Pride weekend. I had a blast and I walked you through the weekend. In particular I went to a mansion pool party but it wasn't a mansion and there wasn't a pool. Don’t forget to subscribe, L…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode, I had an eventful day at work to a professional networking event, and a surprise date, I was booked and busy, honey. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Email: LateNightwithSylvester@gmail.…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode, I discussed Kim Kardashian's attendance at the Usher concert in Vegas. It was an exciting event that caught the attention of many. Additionally, I expressed my gratitude for city workers and highlighted the important role they play in our communit…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. Can we have a conversation about having a seat at the table? What do you do in that position? In this episode I talk about my recent experience with having a seat at the table and putting it to use. I'm still trying to find my way through it all, and I don't ha…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. We're in the month ofJanuary, it's MLK day and it's time we talk about diversity, equity and inclusion. I talked about my struggle with my sense of style in the workplace and wanting to be respected no matter what. My friends called me "extra" this past weekend…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. Happy Holidays, this episode I talked about my fun fact about our Supreme Court life in power, I talked about these men keep inviting me over to their place and the place is a mess, why? Then I asked an important question, do we protect women as a society? And …

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode I talked little bit about my new car and the holidays coming up. I also tried to figure out how to be a supportive friend when your friend(s) may lack confidence. Finally, I talked about Sandy Hook, gun ownership and the race war in our country and…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is dedicated to Cookie Tookie, let her soul rest in peace. I talked about being prepared for dead, getting ready for my new year. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Email: LateNightwithSylv…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode I talk about a new friend that I low-key want to see outside, lol can we go outside? I give my little two cents on the club scene in NYC and all gay clubs across the world. Also, I shared some thoughts on the criminal justice system and where we ca…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. In this episode I talk about going to Spelhouse Homecoming 2022 and I have some feedback for the committee and I talked about having fun being a single man. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Email: Lat…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is part 3 to "Daddy Bu**y & This is Still Daddies Bu**y" where I talk with my boy Raleigh about sex. eduction and housing authority. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Guest Twitter: @ralei…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is part 2 to "Daddy Bu**y" where I talk with my boy Raleigh about where we know each other, sexual freedom and politics. Important Links: sam.gov defense.gov fiscaldata.treasury.gov Affirmative Asylum Eligibility and Applications Don’t forget to su…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode I sit down with my brother and homie Raleigh, as we talk about sexuality, life and politics. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Email: LateNightwithSylvester@gmail.com Music: Too Big (Atjaz…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. Khia MotormoufTV Chasing: LA Cutie in dior LOL Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Email: LateNightwithSylvester@gmail.com Music: I Guess So by twenty weeks *I do not own the rights to this song. Love an…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This is episode 1 of season 5, I'm changing a couple things up and I hope you like it. Special shout out to all my listeners, Late Night with Sylvester has over 10,000 downloads, so thank you! Don’t forget to subscribe, Like and give me my 10’s in the comments!…

Welcome to Season 5! This is just a quickie a.k.a Season 5 trailer. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Email: LateNightwithSylvester@gmail.com Music by: Passion Over Money by A. Cooper *I do not own the rights to this song. Love and Peace!

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time and Ms. Monkeypoxs is trying the girls in the streets. I talked about my girls getting their lives on the apps, me not having a car and a lot more. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @L…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time and life is good y’all. I talked about the Monkeypoxs, the passing of my younger cousin, the gay caribbean experience and embracing my new fetish. This episode got real hot and sexy, hide the kids. Don’t forget to subscribe, Li…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time and I talked about biases we have in this world, the girls are acting up on public transportation and cleared pathed on the Path Train, literally (LMAO). My prayers go out to everyone that has lost someone to gun violences. Bad…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time and life is good y’all. I’m happy, the boys are loving me and kissing all over me, haha ;). So sit back and relax and enjoy the show. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time and I talk about Bill Cosby, my experience at Trax nightclub in Nashville, TN. So sit back and relax and enjoy the show. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Email: LateN…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time and I break down the rules about airplane etiquette. I got a juicy story for y’all about this situation that I found myself in, sit back and relax and enjoy the show. Don’t forget to subscribe, Like and give me my 10’s in the c…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time and I’m back Y’ALL! I took a little winter break, but I'm here. I’m talking about the requirements of being a host, my new attitude on life and I don’t give a f**k, so come on in and enjoy the show. Don’t forget to subscribe, L…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time “The Birthday Edition” where I talk about turning 32, my Ikea experience on my birthday, voting, and the Build Back Better plan. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Emai…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time and it’s the day after Christmas 2021 and I’m just on the mic and talking shit. I talk about narcissism and my new barber. Come in...relax and vibe out with me. Don’t forget to subscribe, Like and give me my 10’s in the comment…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time where I go DA F**K OFF! LMAO! Come on in and enjoy the show. #BuildBackBetter Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Email: LateNightwithSylvester@gmail.com Music by: Makai…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time where I talk about the Kyle Rittenhouse and Ahmauh Arbery trial, Friendsgiving in D.C. and it’s time for Boundaries, Balance, Building and Business in my life. Don’t forget to subscribe, Like and give me my 10’s in the comments…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time where I talk about being single now, Social Media, the Government and the rights of Women. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Email: LateNightwithSylvester@gmail.com Mu…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time where I talk about the Dave Chappelle special on Netflix called “The Closer”. I share my opinion on white media and how they treat black individuals in the media. Dave Chappelle was trolling the fuck out of the world and I love…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time where I talk about SlayTV's new web series called "FOR THE BOYS" on Youtube. Where on episode 8 (FOR THE BOTTOM BOYS) of the show, they talk about preparing to bottom and teaching the girls some new things. Click here for the f…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time where I give y’all a story about work and this beef with my manager. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @ LNwithSylvester Email: LateNightwithSylvester@gmail.com Music by: Ketsa - Revea…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time where I talk about my crazy week at work. I hope y’all enjoy it. My prayers are with everyone affected by Hurricane Ida. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @LNwithSylvester Email: LateN…

Thank you for stopping by and listening to another episode of Late Night with Sylvester. This episode is a Dear Diary time where I talk about my experience seeing Ari Lennox and the girls fighting at the club. I hope y’all enjoy it. Don’t forget to subscribe, Like and give me my 10’s in the comments! Twitter @ LNwithSylvester Email: LateNightwithSy…