I had been going to a local motel to meet up with differnet men for over a year. 

Since my first Craigslist hook up Miss M had me posting ads every thursday in hopes I would find a weekend man to please.

She was very clear that my purpose in going was to give dominant men the release they needed and to prove my sissyhood.

But even if I just posted ads and flirted and sent pictures I was being a good sissy exploring my desires.  

I was still being allowed reprives evey few weeks and would be unlocked but it was rare I would service a master unlocked.

There was one very hunky and powerful dom I served named Ty, he was from Atlanta and was working in LA

We had met online and I had gone to see him a 2 times already when he asked if I could come service him unlocked.

I was really scared that I would cum too soon or he would try to stimulate my sissy clitty and I'd cum and miss M would be upset.

She saw how terrified I was and it seemed to make a wicked look in her eye. She unlocked me and told me to go and not to cum.

I went and Ty was a bit rougher than he had been with me and my liberated cock was rock hard and I kept reaching down and pinching my own balls to try and stop myself from cumming. I knew he would tell her and Id be in big trouble.

I gave him great head and I could see he was very pleased with me. I turned around and he pulled my plug out and spit on my sissy hole and inserted himself.

He was one of the larger men I serviced and I often had to realy hold back from cumming in my cage until he was done.

This time him sliding into me felt so amazing, I wasnt errrect when he entered me but quickly was hard as steel again.  

the pressure from trying to get errect in the cage makes it easy to sissygasm, so it was actully nice not to have it on. 

He liked to slap my balls usualy when he fucked me but this time he was slapping my entire swollen sissy clit.

I felt strange, like i shouldnt be allowed to do this or that I was breaking some sissy rule. I really liked it but was confused.

He kept going and with his huge hand began to crush my cock and balls and it felt somewhat like being caged

It felt so good that I became concerned I would sissygasm and begged him to let go, which he did. but then grabbed me again

This went on for a while and then finally as he squeezed me extra hard he came inside of me with a big grunt and burst of cum

I was so proud of myself for not cumming, I hopped off his cock and got a towel and cleaned him off and he stroked my hair.

This went on for 4 more sessions with Ty servicing him without my cage on (one of them I did accidentaly cum, sorry Miss M)

After my cum misshap I was afraid to see him but really like the way he fucked me and treated me as a sissy whore.

I had never really had longing for any of the men I serviced but this one I was becoming a bit attached.

I saw him 2 more times while caged and begged Miss M to let me see him with my cage off.  She Refused and I complied.

Then one night when i was at the motel with him he broke the awful news to me. He was moving overseas.

I was so sad and I started crying, I had never really felt attached to a daddy the way I was to Ty.

I serviced him so well that night, he came twice in my mouth and once in my sissy hole where I plugged it to keep his seed.

When I got back to Miss M's house the next day I was still crying. She told me it was best I found a new man as soon as possible.

She invited over a few men durring the next week to help get my mind of Ty but I think it took 3 months for me to finally let go.

I still fantasize about him sometimes but never have I heard from him again.

Ty if you read this please know how much those nights meant to me and how special your cock is.