A Life-Changing Experience, Part Six
I could not decide what to do. Kerry obviously knew I was inside, and I surely did not want to try to deceive him, after everything he had done for me. But, notwithstanding our afternoon session, I did not want to go to the door in my current state of dress – or undress. I managed a, “Just a minute,” then went into my bedroom. Suddenly, walking in the heels was not that big of a problem. I figured the quickest solution was to take off the heels and put on a baggy sweatshirt and pull some jeans over my lingerie-clad body. I did so, hid the heels and wig in my dresser, and slipped on some loafers. I took a look around my apartment to make sure everything was in order, then looked myself in the mirror in the bathroom to make sure what I was wearing underneath my clothes was not visible. I went to the door and took a deep breath. As I opened it, I tried to act as casual as possible. “Hi, Kerry,” I said as I stood in the open doorway. He was wearing the same clothes as when I first met him earlier in the day. Kerry gave me a slight smile and looked me up and down – starting from my shoes to my eyes and back down again. I noticed that his gaze lingered on my shoes on their way back down, and my eyes instinctively followed. To my shock and horror, I noticed that you could see a little triangle of black stocking between the hem of my jeans and my loafers. Kerry looked me straight in the eyes, smiled a bit more broadly, then said, “Well, hello again, Andrew.”
Kerry walked past me into my apartment. As I closed the door, he said, “Well, either you had more experience with crossdressing than you let on to me earlier today, or you already found the little present I left for you in the desk and have tried it on.” He waited a moment for me to respond.
“I found it,” was all I could muster.
“And you tried it on?” Kerry ventured.
“As soon as I opened it, I had to,” I admitted.
“Very good, Andrew,” Kerry continued. “And how did it make you feel?”
I thought for a second. “Amazing,” I offered.
“Amazing in what way?” Kerry inquired.
“Well, I love how the stretchy, lacy fabric feels against my skin.”
Kerry took a half step toward me, so that he was now just one arm’s length from me. “And?” he asked.
“And,” I continued, “the way the garter straps pull at the tops of the stockings. It is so . . . so intoxicating.”
“Yes,” Kerry responded, pausing, obviously waiting for more.
“The high heels, with the stockings on, make my legs and calves and my whole body feel so sexy. So feminine,” I offered.
“Yes, they do. Are you still wearing it under your man clothes?” Kerry asked, still looking deeply into my eyes. I nodded. “Everything except the wig and heels?” I nodded again. “Where are they?” I cast my eyes in the direction of my bedroom. “Let’s get them,” Kerry directed.
I started toward the bedroom, mesmerized by the power Kerry had over me without really seeming to try. Kerry followed close behind. Electricity coursed through my body in anticipation of what might happen next.
As I opened my dresser drawer, Kerry sat down on the bed and crossed one leg over the other. I pulled out the wig and heels and placed them on the bed. Kerry looked at me and firmly stated, “I want to see you in it.” My heart skipped a beat, but I had no ability to demur.
I reached for the wig. But as I did so, I immediately heard Kerry say, “No, all of it.” I thought I understood what he meant, but I looked at Kerry and motioned to my sweatshirt and jeans. Kerry nodded slightly. So I proceeded to slip off my loafers and jeans. Every now and then I snuck a look at Kerry, who was overseeing my actions approvingly. I took off my sweatshirt, so that now I was fully exposed in the bra, garter skirt, nylon panties and stockings I had been wearing under my street clothes. Kerry seemed to drink in the sight of me. “Now, put on the heels,” Kerry directed.
I did as I was told, trying to be as natural as possible. However, as I placed the left heel on my foot, I felt my cock starting to stiffen and strain against the panties. I could not figure out if that was a good thing or bad thing. But before I could decide, Kerry softly stated, “I can see you are enjoying this as much as I am.” I looked back at Kerry, and observed that he had removed his shirt to expose his perfect, shaven chest. My cock immediately extended to its full length.
I put on the other heel and stood up to my full height, tightening my calves just a bit to accentuate them. “Yes, very nice, Andrew. Now the wig.” I reached for the wig and placed it on my head, the black locks falling to my shoulders. “Mmm, hmm,” was all I heard from Kerry. I walked over to him, still seated on the edge of the bed. Kerry spread his legs so that I could get between them. He reached around to my ass with both his hands and maneuvered them under the garter skirt and began to caress my taught butt cheeks. Meanwhile, he placed the side of his head on my chest, his right temple resting directly between the cups of the bra. Kerry breathed in deeply several times as he continued to knead my butt and caress the backs and outsides of my thighs. I felt my cock against the stretch nylon of the panties, and felt the light pressure of Kerry’s chest against my cock.
Kerry deliberately took his hands from behind me and leaned back on the bed, propped up by his locked arms behind him. Kerry looked at me and asked, “Andrew, do you enjoy masturbating?” I was slightly embarrassed by the question, but I was certain he knew the answer already, so I just nodded slightly. “Good,” Kerry intoned. “I want you to masturbate for me.”
To be continued . . .