I [F23] made a bet to my boss [M35] during the IPL Finals and gave him a blowjob in front of my colleagues [MF] #walkofshame

Warm greetings to my fellow readers. I’m Aparna, 24, working and an independent lady living in Mumbai. I hope you all watched yesterday’s CSK vs SRH match cause I did. I also managed to watch Sunday’s CSK vs RCB in person with my boyfriend. I was talking to my boyfriend on the way home and it reminded me of that one time I made a sexual bet during IPL 2019 Finals and lost it. So I’m here to confess one of my sexual encounters that happened 2 years ago.

About my body, I’m 5ft 4, brunette hair and brown skin, a pretty oval face, beautiful 36C cups, sexy legs and a plump ass that I didn’t appreciate back in the day.

I’ll give you some context before I tell the actual story. I love, love cricket. Growing up in a family that always watches cricket matches, I eventually grew to love the sport and watch it all the time. This happened during the Indian Premier League Final 2019. For westerners who have no idea what it is, it’s like the Superbowl of India. I was 23 at that time and working for a big firm as an intern. I managed to get a ticket for the IPL Final at Hyderabad. I even booked plane tickets and was excited to see the match. But work got me occupied. What’s worse is that I have to attend a meeting in Delhi with my team on the day of the final match.

I was pissed that I didn’t get to watch the finals, but I’m a responsible woman and work comes first. My team consists of 2 girls and 3 guys with me being the youngest. It was Pooja, the team lead, me, the intern, Rakesh and Krishna. But the guy we need to focus on is Ravi, our manager/supervisor. He was old, about 35 if I remember correctly, had a beer belly, going slightly bald and hairy all the way. I have a love-hate work relationship with him. He makes awesome decisions and works smart but annoys me all the time. It also didn’t help that he was borderline sexist and misogynist.

Anyways, the team knew about my situation and wanted to help me. We scheduled the meeting in the evening and decided to watch the match together at the hotel afterwards. The company that I was working for was nice enough to make us stay at a nice hotel. The company booked 3 rooms. 2 small rooms for Pooja and me and a bigger room for the guys. We got done with the meeting pretty early, so Pooja and I decided to take a shower and slip into something comfortable. Pooja changed to her PJs and I slipped into a baggy low cut black tank top and comfy pink shorts and went to meet the guys. Rakesh and Krishna were nice enough to get some beers and snacks for us to enjoy the evening. Ravi quickly stared at me as I was walking into the room. His eyes gave away his perverted thoughts but didn’t say much besides sexist comments.

The final match was between Chennai Super Kings (CSK) and Mumbai Indians (MI). Everyone was cheering for MI, except me. I’m a huge fan of CSK and I wanted them to win. If anyone had watched that match, you know that it was hectic. The stakes were high. We were all arguing about who’s going to win the finals and I was up against 4 people who are hardcore fans of MI. Ravi came up with a cool idea that got us entertained. We make quick bets on how many runs will be scored in an over. It wasn’t illegal, just casual bets between friends. Ravi was a sore loser in these bets and the rest managed to make some quick cash from him. This made him pissed off, especially I made him since I stole the most from him. This got us into a heavy argument. Ravi said,

>”Come on, Aparna. You’re gonna come in and make small bets. How about we make a big bet? Just between us.”
>
>”What???”
>
>”You heard me right. I bet Rs 2000 that CSK will lose this match. Willing to wager your odds?”

I was a bit sceptical but CSK had a pretty good 1st innings and they had a chasable target. So, I said,

>”Really, Ravi? Do you want to lose more cash? I’m up for it. I bet Rs 2500 that CSK will win.”
>
>”Stop being naive, Aparna. MI will always win.”
>
>”We’ll see about that.”

I was serious about this bet. Ravi annoys me all the time and this was my chance at getting back at him. As the match went on, we raised the bets and it even reached up to Rs 10000 (roughly 150 dollars). I really wanted to humiliate him, so I said,

>”Looks like MI is about to lose.”
>
>”Shut up! It’s too soon to say anything. MI can still win.”
>
>”I think they’re gonna lose.”
>
>”No, they’re not.”
>
>”Really? Wanna raise the stakes?”
>
>”Sure, cause I’m gonna win.”
>
>”Okay then. Besides the cash, if you lose, you have to streak across the hallway.”
>
>”What???? Are you insane?”
>
>”Why the sudden shock? If you’re gonna win, then it doesn’t matter.”
>
>After a minute, he replies. “Well then. If you lose, you have to suck my cock for 5 minutes.”

Pooja interrupted and said this was inappropriate which turned into a big argument. Yes, it was, but I was drunk and confident in my bet. It did surprise me and I’m not really into him, but my drunk ass said,

>”Okay, fine. I’ll suck your cock if I lose.”
>
>Pooja intervenes and says, “Are you insane, Aparna?”
>
>”It’s fine, yaar. I’ll win for sure.”

I’ll skip some parts of the story and explain them briefly. We did raise our bets where I asked him to streak across 2 floors and record them. He asked me that he’ll record me sucking his cock until he cums. Eventually, CSK lost and so did I. I tried to slide my way out of this bet but Ravi and the rest of the guys were pretty hard on me going back. So, I had to hold my part of the bet. I asked him to do it in private, but he wanted me to do it in front of everyone as the post-match presentation was going on. I really messed up and got caught in a messy situation.

Ravi was sitting on the couch with his legs wide open. I tie my hair to a bun and kneel in front of him. I remove his shorts to see a hairy, soft and small uncut cock. I grab his cock and started stroking it slowly. Rakesh and Krishna were watching and it was so embarrassing. Eventually, I started sucking his cock. I bob my head up and down and got him fully hard pretty quick. He wasn’t that big, about 4-5 inches but definitely an average-sized cock. My hands played with his balls as I go down on his cock.

After a while, Ravi picked up his phone and started recording his POV of me giving him a blowjob. He even has the audacity to send it to me with the caption, “This is what happens when CSK sluts bet against a MI fan.” I was pissed off but turned on at the same time. The humiliation was what turns me on and I wanted to be humiliated more. The thought of it really made me wet.

As I was sucking his cock, Ravi’s hands went to my boobs and started caressing them. He also noticed that I didn’t wear a bra. Ravi teased me about it which was really working on me as I was turned on by it. He gave his phone to Rakesh and asked him to record it. His hands went to the hem of my top and tried to pull it. My submissive side kicked in as I raise my hands and he removed my top. My upper body was completely naked in front of everyone and I didn’t mind. For whatever reason, it turned me on.

As soon as the post-match presentation was over, Pooja left the room and went to sleep. Soon after, Krishna went to his room, so it was me, Ravi and Rakesh who’s recording me giving head. Rakesh even asked if I could suck his cock, to which I gave him the middle finger. Rakesh eventually leaves and it was me and Ravi all alone. I’m really good at giving head but at that time, I can’t make him cum. I tried deepthroating him, sucking his balls but nothing worked. Ravi breaks his silence and says,

>”What? Can’t make me cum?”
>
>”Just shut up and wait. I’ll make you cum.”
>
>”I don’t think you’re close. Maybe if you ride on my cock, you can have a chance.”
>
>”Fuck off. That was not the bet we had.”
>
>”But you did bet that you’ll make me cum.”
>
>”I won’t ride on your cock.”
>
>”Ugh…. fine. Just lay down on the couch and open your mouth.”
>
>”Hmm…, whatever.”

I did as he said and lay on my back with my head hanging out. He got on his knees and placed his phone on the table facing us. His hand went under my shorts and felt my wet pussy. He had a weird smile before shoving cock in my mouth and starts throat-fucking me. His hairy balls were slapping on my face as he fucks my face and fingers my pussy. It really got me worked up and I really enjoyed this position. The throat fuck did the trick as he was close to cumming. He stood up and was stroking his cock fast. After a few seconds, he shot thick ropes of cum all over my face, my hair and my tits and stomach. It was a big load and I was covered in thick cum. He got his phone and captured a close up of me.

After catching my breath, I went to the bathroom but Ravi got hold of me and asked me to clean myself in my room. I said fuck off and grabbed my top and got out of his room. I put my face down as I had my walk of shame across the hallway. As embarrassing as it was, it was hot at the same time. I wish I did it with someone I found attractive, but it is what it is. I went to my room, threw my top and shorts to the side and cleaned myself. I went to my bed naked and checked my phone to see Ravi sending me clips of me sucking his cock with filthy captions. I did reply to him saying “Fuck you” and “You’re a POS” but I was also fingering myself watching my skills in action. It was a wild moment for me as I had an intense orgasm and slept peacefully.

A few days went by and Ravi approached me at work. He said he was sorry for what happened in Delhi and was ashamed of himself. He even deleted all the videos in front of me. I didn’t believe him cause he could have made a back up somewhere else. He even gave me the 10K back and apologized to me properly. I took his apology with a grain of salt and we ended our sexual encounter on good terms. I eventually left that job next month to pursue my passion projects.

….. and that’s my story of how I lost a bet to my boss and had to give him a blowjob in front of my colleagues. It truly was a wild ride for me. I’m sure you have a lot of questions in your mind, so be sure to ask them in the comments. I’m not that responsive on DMs but I’ll definitely reply to your comment. So be sure to give me your thoughts on my experience. Any writing tips would be great as well.

Thank you for reading my confession.

P.S. My birthday is coming up, so be ready for a special story soon, featuring my wildest event.

Source: reddit.com/r/gonewildstories/comments/n0x8i4/i_f23_made_a_bet_to_my_boss_m35_during_the_ipl