First Experience

My fetish started in the late 80's when pantyhose were a thing. I remember my college girlfriend wearing them every time I saw her. She oozed sexiness every time I saw her and I relished the chance to rub her legs and feet. My curiosity got the best of me when I was a senior in college, when she left a pair of laddered pantyhose in my trash can before she went back home. As soon as I slid them on, my cock became rock hard. I looked in the mirror in my bedroom and soon stroked myself to one of the most intense orgasms I had ever encountered.

That night I tried to clear my mind, but couldn't stop thinking about wearing pantyhose. After class that night, I drove to JC Penneys to buy my own pantyhose. I nervously walked through the lingerie aisle and picked out 4 pairs of pantyhose, 2 pairs of thigh high stockings and 2 pairs of panties. The pantyhose were black and tan, along with the thigh highs. My panties were red and blue.

I lived in a house with my own bedroom, so I began to wear panties and pantyhose under my jeans more and more at school and at my job. I enjoyed the feeling of femininity and the taboo of it. My job was at a Magazine/Newsstand. I worked 3 nights a week (closing shift) and worked alone most of the time. My boss, Mike, was a single guy, who I couldn't tell his sexuality. He talked about dates, but never gave details. He owned another business in a town 90 miles away as well, so he traveled a bit. He hinted about how good looking I was on occasion, but I didn't take him seriously because he only said it when I bailed him out on a shift.

I was working on a Thursday night. We were getting snow, so I wore my winter boots but brought a pair of black slip-on shoes to wear behind the counter. That night I wore black pantyhose and my red panties under my jeans. My shift went smoothly, and I began my closing procedures. I locked the front door, counted the register and brought the money back to the safe. I shut the safe and went to the breakroom to put my boots on, I slid off my boat shoes and decided to use the bathroom first. I figured no one was around and I decided to walk in pantyhose feet to the bathroom. I used the bathroom, and was walking back to the Breakroom when I heard the backdoor close. I tried to run to the breakroom to put my boots on but Mike was in there. I stopped and he said "I have some good thoughts on this place, wait are you wearing pantyhose?"

I froze, here I was, my feet covered in black pantyhose with a reinforced toe completely exposed. I just nodded and he said "Interesting, I suspected you had some fetishes, the way your girlfriend dresses, but I didn't see you as a crossdresser. I have to admit it's kind of sexy." I blushed as I walked in the breakroom,

Mike looked at me and said "How many people know about this secret?" I looked at him and said "only you." Mike replied "Not even your girlfriend?" I shook my head. Mike walked over to the backdoor and locked it. He walked back in and took off his pants and stood there in his underwear. His cock looked hard under his boxers.

"If you want to keep this a secret Chris, I suggest you take your jeans off." All this was overwhelming, but I was semi hard in my pantyhose. I slid my jeans down and stood in front of Mike in black pantyhose and red panties. He smiled and said "This does excite you, I like that" Mike walked over to me and put his hand on my thigh and moved it slowly to my ass. He began to breathe hard and he brought both hands to my ass.

"You have an incredible ass Chris, especially in panties and pantyhose." He pulled his boxers down and grabbed my hand and moved it to his cock. For the first time in my life I had another man's cock in my hand. His cock was rock hard and I gently stroked it. He put his hand on my hips and turned me towards him, he then put his hands on my shoulders and pushed me down.

I knew what I was to do, standing there in my pantyhose and panties, precum leaking into the crotch of my pantyhose. I knelt down on the cold floor and moved my mouth to his cock. I opened up, he thrusted his hips and his cock was in my mouth. Mike gently spoke to me "Chris, suck and make sure you don't drag your teeth". I reached up and stroked him as I began suck his cock. Mike continued with encouragement "Very good Chris, are you sure this is your first time? I bet your girlfriend would love to see you in her pantyhose sucking cock" I reached down with my other hand and stroked my rock hard cock in my pantyhose.

Mike began to breathe heavily and put his hands on the top of my head. "Here it comes Chrissy" he blurted out as cum shot into my mouth. With no experience I pulled my mouth off and cum hit my nose, chin and began spurt onto my thighs, soaking my pantyhose. I slid my hand inside of my pantyhose and jerked my cock until I shook and I unloaded the biggest load of my life into the crotch of my pantyhose.

I stayed on my knees for a second, processing what happened. MIke came back and handed me Kleenex. I cleaned up my face, and nylons as best I could. Mike was in the breakroom as I put my jeans back on and put on my winter boots. Mike looked at me and said "I think there will be a dress code for you now Chrissy, unless you want your secret out there."