I’ve Had 75 Men - Jack Was 2nd

I was in the FL Keys, Duck Key specifically, at Hawk’s Cay Resort. I was in the Keys with my employer, Joe, who sucked me occasionally. His best friend Jack was there for a few months on his liveaboard boat. There were about 7-8 of us out for dinner that night. Lot’s to drink.

Somehow I wound up spending the night on Jack’s boat instead of the hotel. Jack quickly convinced me that we needed to give mutual massages. I knew what was going to happen and was quite happy to go through with it. He made me take a shower then he massaged me while I was wearing only a towel. It didn’t take long for the towel to come off as he massaged my ass, causing it to move uncontrollably under his touch.

Next he move me into his bed. After sucking him for a while (my first cock ever) he wanted to fuck me. So not knowing exactly what to do, I went head down ass up, but he said no, and put me on my back with my legs up on his shoulders. He used Vaseline lotion to lubricate me, and then slowly pressed in. I had had my share of dildos and homemade anal toys so I was ready. It was the most incredible experience I’ve ever had. At the age of 26 I was taking cock that I had fantasized about taking for probably 15 years.

Jack fucked me hard that night as I moaned like a sissy whore. I remember thinking…’Is this who I am…it feels so right’. He came big in my ass. I felt his load pump into me. He wanted me to fuck him but I was too drunk. In the morning I was hung over and couldn’t believe what I had done, but I was hooked. It would be the start of a life of cock-taking.