First time for everything [MM]

All this Isolation stuff had me thinking back to when I was 20 as I was commission only back then in a sales role and wasn’t making much money. Now not being able to work and still being commission only its very similar (although now I am a lot better set up so its not a huge issue yet.

I started a new job and as mentioned it was purely commission based. Knowing that if you didnt get any sales or deals across the line you wouldn’t earn any money but the chance to earn a lot was a great incentive compared to the salary role of the same nature. the first few months were up and down and was doing enough to live and pay rent, notreally save anything. Then about month 6 things started to slow down a lot and it was getting a lot harder to get by. we were living off my girlfriends wage alone which was putting a lot of stress on our relationship.

I had started looking for new jobs and went and spoke to my boss. He was a well built fit guy in his 40s, short salt and pepper and married. My girlfriend used to always say he was hot and couldn’t wait for me to go grey like him.

I went and spoke with him and explained the situation and how I was going to have to leave as I wasn’t making enough money and was struggling. He asked if I could hold off a week and he would see if he could come up with a solution. I agreed.

A few days later I was closing up the store and it was just me and the boss left. He asked if he I could come to his office once everything was locked up, nothing strange as we often had beers after work. I went in there and we started talking about the work situation. He said he had come up with a solution if I was interested but it would be off the books and had to stay between us. At this stage I was very confused. He was sitting next to me and told me that he would be willing to cover my rent and a little bit extra if I was willing to do something for him. I asked him what it was. He looked at me with a coy smile before grabbing my hand and placing it on his dick which was already hard in his pants.

I freaked out as I had always considered myself straight and had never even thought about doing anything with a guy. He obviously saw the look on my face nd said I didn’t have to give an answer straight away. We finished our beers and left for the weekend.

I couldn’t stop thinking about it all weekend and got more and more excited about it. I went into work the next week and every time I saw or spoke to the boss I got excited. Friday came and again it was just the 2 of us left. I locked up and went and had a beer in his office. He was on the phone to his wife so I sat there and basically drank it on one mouthful and got another. I was halfway through the second when he got off the phone. we started chatting and then he asked about what we had discussed. I told him I couldn’t stop thinking about it and was in. He asked if I was ready to start tonight, I said yes already hard in my work pants. My boss stood up from behing his desk and I could see the bulge in his pants. He took his short off and started undoing his pants. He had a reasonably hairy chest and stomach but quite fit.

He removed his pants and underwear to reveal a manicured cock about 6-7 inches and cut, quite thick.

He walked over to me lifted my shirt over my head. It now occurred to me that we hadnt actually discussed what was involved in all of this and I stopped him. He told me all he wanted was a Blow Job and he would cover my rent and some living expenses but he just wanted to see me naked while I did it. So I took my shoes off and he undid my belt and pants and pulled them off. releasing my rock hard cock, hairless and cut and around 9 inches.

I never thought I would be naked in my workplace but here i was with my boss both naked, I told him I had never done this before and he was like thats ok. He had a couch in his office so He sat down at one end with one leg up on the couch and invited me over while he stroked his cock. I was so nervous as i sat down, I could feel my legs shaking. I started to play with my own cock. He grabbed my hand and placed it on his cock. It felt so hard and thick in my hand, i strted stroking it as I stroked my own, he moaned in pleasure.

I hesitated, composed myself and let in to sucka cock for the first time in my life. I slowly kissed the tip and then opened my mouth and took the head in, it felt great in my mouth and I started to go deeper, which wasnt very far (and if I’m honest i gagged a couple times) I started working his shaft with my mouth and hand and he was moaning and holding the back of my head.

He told me he was getting ready to cum, I started working faster with my hand and I felt him tense up as he squirted his warm cum into my mouth, it was salty but not disgusting like I thought it would be. I let it dribble out my mouth and down his shaft onto his balls an pubes. He started to go soft and was relaxed and told me I could cum if i wanted to. Isat up and blew my load all over myself and the couch in a few seconds.

We sat there in silence for a bit and then he got up got us another beer and some paper towels to clean up. We sat there naked drinking our beers and discussing what had happened.

we got dressed and parted ways for the weekend. I received a message from him asking for my bank details as he was out of the office for a few days. I sent them through and a couple days later $500 appeared in my account. My share of the rent was only $200 so I was grateful. I told the girlfriend that I had just got a good sale that week.

This continued on exactly the same every Friday night sometimes other nights as well. Same amount of money. Even when my sales got good again amd didn’t really need it.

To be continued ….

Source: reddit.com/r/gonewildstories/comments/g2um2a/first_time_for_everything_mm