When I was a young boy, I started to find a fascination with feminine things. Not sure how it started, but one day I found myself trying on some of my Moms things and enjoyed the feeling. The issue I found early was that my Mom was very vanilla in her things, so I started to explore with an Aunts things, one I spent a lot of time with, as her son and I were very close. She had very sexy panties, bras, slips and pantyhose, so I would sneak them into the bathroom at her house, put them on and masturbate in them. I did this for some time, but found the desire to actually walk out of the bathroom in the things, pushing myself to do so.
I decided one night, late at night, to go to the bathroom, put them all on and come out to walk around the house a bit, as everyone would be asleep. I went to the bathroom and pull on her lacy panties, silky pantyhose, lacy bra and short slip. I took a deep breath and opened the door, quickly cut the light off and started to walk down the hallway. I could barely walk, as my legs were shaking so much with excitement and fear, as I knew the further I got away from the bathroom, the more likely it was I could get caught. I got down to the living room and sat in the chair for a bit and started to masturbate, feeling so thrilled, yet so scared at the same time.
Just then, like a flash of lightning, the lamp came on and standing there was my Uncle, just staring at me. I was mortified and started to get up to leave, but he told me to sit down, so he could take a look at me. There I was sitting in the living room in my Aunts sexy things, with my Uncle looking me up and down, raping me with his eyes. He told me that he suspected something was going on for some time, as he heard noises from the bathroom at times. He then asked me if I wanted to be a girl, which I answered by saying I sometimes wanted to feel what they feel. With that, he walked over to where I was sitting and pulled his semi hard cock out of his boxers and said that if I wanted that, then I should touch a mans cock. I lightly touched it and it jumped when I did, starting to get harder as I touched it. He then said, that I was now to put it in my mouth, which I said I did not want to, but he said that he knew better, since I was in all these girly things. So, feeling I had no choice, I opened my mouth and he pushed his cock into my mouth and told me to wrap my lips around it and suck it gently, which I did. He started to moan and piston it in and out of my mouth and I started to enjoy what I was doing for him.
He then stopped me and left the room for a bit, returning with a jar of Vaseline, telling me that I was now going to feel what a woman does when a man fucks her. I said that I had never done that and was not really into it, but he said that if I was going to wear his wife's things, I was DAMN sure going to do what she does. What could I do, as I was in no position to argue at that point. So, he told me to bend over the couch, which I did, then I felt him come up behind me, start rubbing my ass through the slip, hose and panties. I then felt him push the slip up on my back and slowly pull down the hose and panties, asking me if I like it. I just kind of whimpered a bit, which made him giggle, then I felt a greasy feeling finger start to enter my virgin hole. Slowly he pushed in one, then two fingers, with me whining a bit and pulling away. He just kept pulling me back to him as I did, telling me to stay still, as I felt his fingers pull out. Then, I felt what I knew was his cock and it felt like it was going to rip me open, but that did not stop him, as he just told me to shut up and be the girly boy I wanted to be. Once the head got past my entrance, he held it there a bit and slowly pushed the hole thing in me, telling me how tight and nice I felt. He then started to fuck me harder and harder, with an occasional smack to my ass cheeks, telling me to ride him harder, until he told me he was going to cum. He shoved one last, HARD, time in me and I could feel his cock swell even bigger and then pump what seemed like gallons of cum in me.
He then, without saying a word, pulled out of me, put his boxers back on and walked back to his room. I was there, bent over the couch, slip on my back, panties and hose down around my knees, cum dripping out, not sure what to do. So, after a few minutes, I pulled them back up, walked down the hall and took things off in the bathroom.
We have NEVER mentioned that to anyone since then, but he smiles that special smile at me every time I see him now, with only us knowing of our one special night.
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