Gregory’s Humiliating Feminization Experience

After many years of fantasizing about seeing a Mistress, I finally researched those in my area and made an appointment for a several hour session, I wanted to experience what feminization was like.

She first shaved my genital areas, then dressed me in a garter belt, thigh highs, matching bra and panties. I put my own pants and shirts.

We went first to a lingerie store, after selecting a couple of pairs of bras and panties, I had to take the items to the woman cashier and first ask her if she thought the selected panties would fit my 34″ waist, and then ask if she thought the bras would fit around my chest. So, so, so embarrassing.

Next we went to an upscale adult store. We would select an item then I had to ask a clerk something about it that would ensure they knew what was going to be done to me.

I had to ask if she thought the cock ring would fit my small cock. Then if the nipple clamps were for men as well as women. If this dildo would be too much for an anal virging. What was the best anal lube. We also purchase some cheap, slutty lingerie. All paid for, we asked if we could use the dressing room.

She had me strip down to lingerie, then put the cock ring and nipple clamps on. She bent me over the chair and ass fucked me with the dildo while I masturbated and came hard into my sheer panties, and cum leaked through and ran down my legs.

Then we drove to a large mall and parked in a fairly empty area. Down to lingerie again! She spanked me hard, making me beg for more. Used the dildo again, she jerked me off this time, making me cum in the panties again.

We drove to back to her house-I had to sit with just the bra, garter belt and panties on, and I know some drivers looked and saw.

I had never been so embarrassed and humiliated, and had never orgasmed so hard.

In her house, well I had 3 more hours scheduled, but that is a story for another day.