Link to eighth post: https://www.reddit.com/r/gaystoriesgonewild/comments/1br23zc/the_path_to_becoming_a_sex_slave_28m_part_8/

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When we were done they let me cleanup and we spent the rest of the evening hanging out. Before leaving they signed my pelvis just above my cock with their names and took a picture. I nearly forgot to put my clothes back on when it was time to leave. They reminded me and I giggled given them both a kiss before I left.I couldn't wait for our next session now having lived out the fantasy of being with two guys at once.

Age Recap 25-26, 42 and 45

Part 9

My two new Masters were a dream. I would go over every week and occasionally spent a weekend with them. If I typed up everything good that happened with them we would probably be into 50 parts so I am going jump around to some highlights and pull out some notable points in between.

The first three months were straight forwarded. I spent everyday locked and got cleaned/shaved once a week when I was with them I had been forbidden from touching my cock and all maintenance was done by them. Otherwise I spent a lot of time with fingers, toys and dicks in my ass and mouth.

At the start of the fourth month I pulled up to the house like usual and went in. I usually had a bin by the door to put my clothes in but today hung next to it was a a skirt, tube top and collar with a note saying "your outfit for the night." I put them on knowing I looked a little ridiculous, I could never be considered to have a feminine body but still the change from simply being naked and the humiliation of my appearance turned me on.

Walking in I met my Masters and was told we would be doing something different tonight. They spent some time making me pose while they took pictures all while I wondered what was happening. Soon they showed me a Grinder that advertised a "CD Slut Taking Cock all Night." My Masters explained they would be choosing some guys for me to hook up with so they would get some "blackmail material" in case I ever misbehaved. We had talked about this in our initial agreement but I always thought it was just going to be me covered in cum or getting pounded. Now I realized it was going to be me poorly cross-dressing fucking strangers.

The first guy arrived and was just an average looking dad type (40s I'd guess). After some less then good make out time he fucked me doggy style on the floor. After he left I told my Masters that I hope they could find better then that or else this would be a boring night for all of us. I was was punished with a hard slap to my ass and I remember being told if I wanted it to be more embarrassing fine. Fred brought out a ring gag a toy I had never experienced.

By the time the second guy showed up I was drooling not being able to shut my mouth to swallow. This guy looked a bit younger likely in his 30s. Evidentially they found someone more aggressive as when he walked up to me he grabbed my hair and slid his cock out. I barely had a second to prepare before he jammed it to the back of my throat. He spent the next 10 minutes viciously fucking my face. He is still the roughest throat fuck I've experienced. While he came in my mouth all my gagging made sure most of it was leaking down my chin. Bill came over after to clean me up a bit and asked if that was exciting enough.

I fucked 3 more guys that night. After I cleaned up they brought me over to the living room and tied my hands behind my back. I was one of my usual dildos on the ground in front of the TV and I was made to straddle and sit on it, something I was very used to. Kneeling over it on the ground a happily sat all the way down to the base.

Fred came and unlocked my chastity cage before flipping on the TV and it showed the camera feeds from me fucking the strangers. While none of it was too shocking I now knew it was recorded but what caught me off guard was Fred began jerking me off. His hand was too big for my cock so it was only with his thumb and index finger. This was surprising because while I was in chastity 24/7 I had been allowed to jerk myself off in front of them every couple weeks. It didn't take me long before I came, my ass tightening around the dildo a feeling I hadn't had since I started my slavery.

Fred then told me something I remember clearly, "I hope you enjoyed that because it is the last time you will be allowed to cum this way. From now on you can only cum through your ass." I was excited in the moment but later realized I had not fully achieved that yet and it seemed like an impossibility. Getting off my dildo my legs were shaking I was put in a new chastity cage. It was one of the flat ones.

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