The end of our sophomore year was approaching we were all focused on our studies and had slowed down how often we all fucked. It was becoming clear that emotionally Kate and Emma were dating and Sarah and I were dating. On top of that the four us still fucked and still had some level of emotional relationship between the four of us but we were all now in a comfortable rhythm. Part of that rhythm was the continued dominance of Jon. Sarah had handed off her key to Emma and now Emma and I enjoyed brutally dominating him together.
Over the months our domination of him had become complete and he spent large amounts of time in our suite simply being near us. All four of us would tease him and we enjoyed making him wear thongs over his cage. Our most recent step has been to make him our maid. Now this was a total maid thing but he had expressed his interest in cross dressing and as a result when we did a big clean of our apartment we had surprised him with a maid outfit which he happily wore while he helped us clean.
It was time for the next step according to Emma. So her and I brought him out with us to go shopping. We bought a new and much smaller cage for him as well as a remote controlled butt plug. We switched out his cage and put the new plug in in the mall parking lot and entered. We helped him pick out several pairs of nice underwear and some sexy ones that looked good on his nearly hairless body. We also helped him pick out a basic make up pallet and a few skirts and blouses. When we finally got back to the suite we did his make up and started the fashion show for Kate and Sarah. They both loved it especially some of the lingerie we got. As a reward we made him cum in his cage using the plug. Like a good like slut he caught most of it in his hands and ate it up at Emma’s command.
That then began the habit where Jon spent at least four night as week cross dressing at our suite before going home. Until of course Emma finally encouraged him to wear it out. One Friday night we all got ready wearing our thongs and doing our make up and hair. We all wore plugs and teased one another constantly, especially Jon. We each dressed really cute and found our way to a frat party. When we got there we each got hit on more than once until one guy approached Jon and hit on him. He seemed neither interested or disinterested until the stranger leaned in for a kiss. We all watched excited as they briefly kissed before Jon broke it off claiming he wasn’t ready just yet.
As a reward for cumming out that night Emma used the plug to make him cum in the bathroom. The night ended and we all went home and fucked. Jon also got in on it but his cage was not removed, though he did get to cum two more times. To end the night we tied Jon to the spare bed in Kate’s room and tied a wired vibrator to him just under the balls. When we woke him in the morning there was a small puddle on cum on his stomach. He told us that he had cum four times before he passed out from exhaustion and that the puddle had grown since. This seemed to both anger and please Emma. She informed him at as punishment it would be a while before he was unlocked again and that he was no longer allowed to wear boxers but instead had to wear panties everyday. To top it off she got a dildo and make him suck his own cum off of it for a few long minute in the morning as we all watched.
He seemed to be enjoying himself and together Emma and him developed the outline of a plan to have his first gay experience. Over the next week he enjoyed being in our apartment even more and cross dressed almost every time he went out with us. He moved on from our loser and slave to our sissy and cumslut.
Source: reddit.com/r/Erotica/comments/11k25s8/take_of_two_friends_part13_ff_college_ffm_femdom