My wife (Allie) and I (Rory) have been together for a little over three years now, she is quite aware that I'm the kinky, weird one out of the two of us. We are both in our late twenty's with fairly successful careers thus far. Soon after we started dating, through casual talk, she informed me, that in every relationship she was the controlling one. Why she didn't feel it necessary to be that with me I may never understand. For the first couple of years she satisfied my fetishes on my birthday with random sprinklings throughout the year as well. Lately though, I have been fairly pushy about one subject in particular, chastity.
Before continuing I'll give you a brief description of ourselves as something to put in your head. I myself am average height at 5'9" blonde hair, blue eyes, a little on the chubby side nowadays. I'm not small by any means and have the body type of somebody who was once in shape and now enjoys a bag of Cheetos every now and then. Allie is a little shorter than me at 5'7" dark red hair, brown eyes, 36C's into wide hips but keeping that sharp slant inwards at her stomach. Thick enough that jeans are tight but still has the athletic form from playing soccer through school.
One day we are both on the couch watching TV, I "casually", or so I thought, brought up chastity again.
"So, you remember that weird thing I wanted to try a while ago? The chastity one? Have you thought anymore about it?" I blurted out.
Allie just rolled her eyes and picked up her phone to continue whatever she was doing. I took it a step further this time and brought up a picture of one for sale on my phone.
Sheepishly I said "Well here's what they look like just to give you a point of reference..." When I showed it to her, she looked weirded out but didn't immediately turn away.
"That is much smaller than what I thought it would be, wouldn't it hurt you?"
Admittedly I got very excited, solely at the fact that she so much as acknowledged what I just showed her! "No! It won't! Remember how small I am after a workout or mowing the grass? That's how small it should be, no room for erections at all."
She snickered at that "Well in that case it can't even be that big." She said it in a forced plain way. I could tell though; she was amused a little bit "Anyway we can't be spending that kind of money right now."
I couldn't believe it, was she actually caving on trying this? What could I do to convince her if money was the only obstacle "What if I cut my eating down to come up with the extra money, me not eating extra stuff all the time would pay for this in less than a week!" I was obviously in desperation mode at her giving me the slightest hint she might do it.