In my early 20's a work friend and I used these tiny and new at the time digital cameras to secretly set up and take pictures or short videos of girls we had sex with or sometimes sneak pics and videos of them getting in the shower.
That was our little secret at work. What he didn't know was I had another secret. I had been cross-dressing for about 5 or 6 years. It started out, that I only did it when I masterbated. Soon I was changing into panties, bra, thigh high stockings, and nightgown as soon as I got home from work. I even slept in that if I didn't have company over. I started getting more adventurous and wearing them under my clothes when I went to the store or gas station.
I was able to set my camera up and got a unbelievable great video of me finally fucking this girl I had went out with a couple of times. She was a screamer and the camera placement was perfect for once.
I told my work Buddy about it and he was excited to see it. We didn't hang out after work or anything. We usually just showed each other the pics on the tiny camera screen.
I forgot the camera in my car when I got to work the next day but promised to show him the video soon. He knew the girl so that's all he talked about all day. I was going to show him after work but in a hurry to get home and put on my "other clothes" and watch the video on my TV screen, I drove off. Once home I changed. I decided to go to the gas station for cigarettes. I put my jeans on over my panties and stockings. A t-shirt and thick sweatshirt was enough to make the bra I was wearing, undetectable. My mistake was I put my low ankle socks back on. They were fine when I was standing but I noticed in the car that seated. The black silky nylons I was wearing were visible. I thought about turning around to go get higher socks but decided against it. Another mistake.
I ran into my work Buddy at the gas station. I was completely caught off guard and terrified. I had never had been this close to someone I knew with women's clothes on underneath my regular clothes. He asked if I had the camera with me? Still in a panic I answered truthfully yes. He said "follow me to my place. We can watch it on my TV." I knew if I said no that he would want to come to my house. Where there is a awful lot of panties bras and assorted colored pantyhose laying in the open. I agreed to follow him.
His place was a lot like mine. The only tv was in his bedroom. That way if any girl was brought home. If they wanted to watch TV it would have to be on his bed.
He took his shoes off before he went in his bedroom and told me to do the same. It's the only room in the house with carpet. If I ruin it I won't get my deposit back. I carefully took my shoes off and stood by the bed. He started the video and said you can sit down on the bed.
I tried to sit down as quickly as possible into the crossed legged Indian style so that I would be sitting on my feet and no possible way to see that I was wearing nylons under my clothes. Being so nervous I nearly fell off the bed and my leg raised. So did my pants leg. Halfway up my calf. My face turned red and his eyes got huge. He acted like he didn't see it and got up real quick to adjust something on the TV. I was frozen. Sitting tight on my feet now. He stood in front of the TV saying wow, watching me fuck this girl he knew on the screen. She was moaning and starting to yell a bit. He turned and walked back to the bed. This time before he sat back down he took his socks off. After he got comfortable on the bed. He said without looking at me. If you're gonna sit on the bed, take your dirty socks off. I was trying to think of a excuse to tell him why I had what I had on but couldn't think of anything. I knew if I went to get up he would see. I just started talking about what the girl on the TV screen was going to do next. I pretended like I didn't hear him say anything about taking socks off. While I was talking he grabbed under my left knee and pulled my leg towards him. I fell onto my back. His thumb slipped in between my sock and ankle and slid it off. I fell silent. For the first time in my life someone seen my nylon covered foot. He remained calm. Like nothing out of the ordinary was happening. Leaving my left leg close to him. He reached over my body and pulled my right leg to him to do the same thing to that sock. When he did my left leg was pushed against him and I could feel he was hard. Once the right sock was off. He started rubbing his hand up and down my ankle a bit. He said I always liked the feel of pantyhose. I put my hands over my face. I could feel myself wanting to cry. He asked if I was wearing panties? I just nodded. My hands still over my face. I felt him unbuttoning my pants. He tugged gently until they were off. He raised me back up and lifted my shirts up and off of me. I dropped onto my back once more covering my face. Laying there in front of someone I knew wearing only thing highs, panties and bra. I heard him say it looks good on you. I felt the bed bounce a few times but kept my hands over my face. When he pulled my hand away. I seen he was up on his knees with a cock larger than mine just a few inches from my mouth. His thumb gently pushed on my chin until my mouth was open and he leaned forward guiding his cock into my mouth. His precum slid and settled on my tongue until I swallowed. He couldn't get all of it to fit in my mouth without me gagging. I went from having going in and out of my mouth at his rhythm to going after it and sucking. Trying to take more of it in.
He pulled it out of my mouth. Reach into the top drawer. His hand came back with a condom and lube. He handed me the lube and opened the condom. He said if I'm going to have my first gay experience. It's not just going to be a blowjob. I opened the lube. Poured some into my hand and rubbed it as far as I could inside my ass. His waist made my legs spread wide. It was a strange position to be in. It must have taken 20 minutes of little pushes at a time to get what now felt like a massive cock inside of me. He eased it back just a bit and pushed back in. Each time he would pull back just a bit more then slowly push all the way back in. Each push forced a little moan out of my mouth. I always thought girls just did that to sound sexy. Then he pushed in a little faster. I moaned louder. He pushed harder. I got louder. I could see my pointed toes jerking in the air each time he pushed. Then I could see it in his face. The moaning had him wanting more. He leaned back. Grabbed my hips and jerked me hard towards him. By my ankles, he put my feet high in the air. He started pumping short but fast. Then the weirdest thing happened. Those painful pushes started feeling good. Really good. I started pushing back towards him when he was going inside of me. Seeing my own feet in the air. Feeling him fuck me. Was so exciting. Without even touching my dick. I came harder than I ever had. My own cum shot all the way up to my face. He threw my legs over his shoulder s. Leaned his weight on me and thrusted harder and faster than I knew was possible. It was that good pain all over again. I couldn't stop myself from screaming.
He finished pretty quick after that.
He went to the bathroom. I dressed and left. We rarely talked after that. About a month or so later he quit and moved. It was embarrassing but great sex.
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