Hey all, so a short backstory. I'm a sissy, straight, who's really into humiliation. Not for everybody, but it floats my boat.
About 3 years ago, I started going to a Massage Salon near my house every month or so. Usually 6-8 girls working, mostly Latina and Asian, with the occasional Eastern European girl in the mix. This is one of those places where it's obvious that "Extras" are on offer, for the right price--beyond just a "Rub and Tug."
Now, when I go for a massage, I'm always wearing my bra and panties under my "Normal" clothes, and I'm always in my chastity cage. Most of the girls would chuckle a bit, give me a massage and try to ask about extras--but with my member caged there wasn't much they could do.
That was until Ewa showed up, about 2 years ago. Ewa was a stunning young (19-year-old) Polish girl with long blonde hair (Usually in a pony tail) small pert little breasts and a perfect round little ass. Honestly, if she was a little taller she could have easily been a model.
I was immediately smitten, and asked if she could handle my massage that day.
Ewa took me into one of the rooms, and told me to undress. She laughed when she saw my underwear, and told me to take that off as well. The look of amusement on her face when she saw my little chastity cage was SOOO embarrassing (And SOOO hot!)
She came over and crouched in front of me "May I touch it?"
"Yes Ma'am."
As she pulled and twisted the cage "Interesting, do you like wearing this?"
"Yes, Miss Ewa."
"OK, then. Lay down and we will do massage."
I lay on my stomach, and Ewa began giving me one of the best massages I've ever had. Firm strokes that relaxed and put me in a near trans state. After about 20 minutes "Turn please."
I looked around for the towel, the usual covering for the turn.
Ewa laughed "You don't need to cover. There's nothing to see anyway!"
I turned over, and Ewa gave me an equally relaxing massage on my front side, ignoring the (Rather small) elephant in the room. After about 15 minutes, Ewa leaned down and asked me "Do you want to cum?"
I groaned "Of course, Miss Ewa--but it's locked up!"
Ewa laughed "Turn over again. We'll see what we can do."
I obliged and Ewa began massaging my buttocks, quickly working her way into the crack. She slowly began massaging my anus with one finger, and squeezed way more oil on it than usual. The finger quickly worked it's way inside, and in short order was joined by another 2 fingers.
I felt a tremendous rush of horniness when she began massaging my prostate, and came in only a couple of minutes. It shocked me that I could cum that quicky while soft and caged, and from only ass-play!
Embarrassed, I gave Ewa a very generous tip, and started to head to the door. Ewa stopped me.
"Did you enjoy today?"
"Yes Ma'am." I nodded quickly.
"Good, me too. I have lunch now, you buy me lunch." It wasn't a question, but I was delighted to take her to lunch.
At lunch we talked. Ewa was from Lublin, in Eastern Poland, and had come to the US to live with cousins 3 years earlier. She was smart and funny, but she really wanted to push me.
"So...why bra, panties, and a cage?"
"Well," I blushed "I'm really a bit of a sissy, I enjoy humiliation, having beautiful ladies laughing at me. And I wear the cage partly for the same reason, and partly to keep from playing with myself all the time." My face was bright red at this point, but Ewa looked like she was discussing the weather.
"So, no girlfriend then?"
"No, no girlfriend."
"So, how do you decide when you get to cum?"
"Well, I guess I just decide. I cum when I want to, but the cage makes me think about it."
"And how often do you play with yourself?"
"I guess every 10 days to 2 weeks, it really depends on how I feel."
"Do you want a woman to control that?"
"Yes, Ma'am, but I've just never met the right woman, I guess."
Ewa laughed "Do you have the key with you? Can I see it?" It wasn't really a question.
I quietly pulled out my key chain and pointed THE key out to Ewa.
She shook her head, and held out her hand "Take it off the keychain and let me see it."
I nervously did, and handed the key over with some trepidation.