I jerked off with my Boss in his office
So i worked at this small store because it was close to my house and it was really easy work, all I really did was restock the shelves. There were a few other employees, all women besides the owners being a guy (the boss) and his wife also working the store. Everyone was really nice to me when I had started, but I always noticed the owner had a habit of looking at the employees asses when they walked past him. I think that’s why he had them hired, near christmas I remember him asking one of his employees to come in with her holiday outfit she had posted online, and she did. I noticed he would stare at her cleavage and ass. (To be honest, I wasn’t any better I was doing the same but I just noticed him doing it.)
I think he started to catch on that I was also doing it and one of the times we both glanced to see if we both were looking and caught each other, he smiled and I looked away. This kinda kept going on til one time he brought it up, he asked if the new girl had a nice ass, and me being caught off guard i was like uh yeah! and continued working. One of the last incidents that I saw was him scrolling through of one the girl’s social media looking at her photos, that’s when I knew he was a huge old perv. (I do the same to be honest)
Eventually me and him had to close the store and I was counting the money and he was behind me reading papers or something. That’s when he asked me if I thought his wife was attractive. I admitted yes, and he laughed saying that he caught me glancing at her a few times the past few weeks, and I brought up that I caught him glancing as well! We both started talking about the glancing and then eventually started talking about the girls. So every night that we closed we’d chill in his office while he counted the money to talk about the other employees, the conversations slowly turned out who we’d fuck/ like to get a blowjob from.
One of the days he asked if I would like to see his wife’s tits, and he did just that. I remember being so hard cause of course I’ve always wanted to see it, it was really nice us bonding over something so pervy. From that day on, he showed me whatever nudes he had, and I asked if I could keep one and he joked that for what? Jerking off? We laughed but he knew that was exactly it was for, he did a compromise where he’d give me his phone to jerk off with since he did promise his wife not to send/show anyone. I was really hard after he mentioned that, and I asked him if he was also hard (pretty bold of me haha) and he admitted he was but he would let me have my privacy unless I didnt mind. I told him I didn’t so we both sat in the chairs side by side while he showed his wife’s nudes on the phone. He asked if I was really okay with this and if I was actually comfortable, he tried to make sure I didn’t feel pressured but I thought it was hot so I was okay with it.
We both agreed to pull down our pants at the same time so that’s what we did. We counted down and we did, I looked at his and he looked at my cock. Mine (6 inches) was a bit bigger than his( i think it was 4.5 or 5) his was much hairier, he was cut and I was uncut. He said Nick cock and I complemented his back. We both sat side by side again, and started jerking off together, we jerked off to the other employees as well, talking dirty about them and telling each other our fantasies. He asked if he could get naked and I didn’t mind, so he did. My heart was beating fast cause I’ve never really done anything like that before. We kept saying stuff we’d do and that kept us super hard and leaking pre cum. He said he was going to cum but I wasn’t there yet. So he ended up cumming first, he apologized for that and said that now it was my turn to cum.
He showed me pictures of the girls and I showed him porn of Harley Quinn, and other porn I liked. It was hot to see him talk about how hot the porn I liked was. Eventually we returned back to the employees and he was with me stroking his soft cock talking about how hot it would be if I fucked them. He offered to jerk me off with I was comfortable and I accepted and he jerked my cock faster and faster to their pics and I couldn’t hold it anymore so I ended up cumming but since we were sitting in front of each other at this point I ended up cumming on his thigh. I apologized but he was cool with it. We cleaned up and got dressed! I think it was an awesome experience and I’d love to talk about it with anyone reading this.
Posted Mar 14, 2026, 12:29 AM UTC