A Beautiful Nightgown Made of Silk

For as long as I can remember, I always wanted to wear girls clothes and would indulge that desire whenever possible. I would always sneak to try on my girlfriend's lingerie, which was usually very boring cotton stuff. One weekend during spring break from college, I was staying at my uncle's vacation home on a lake, and met some neighbors. They invited me to join them for an afternoon of water skiing. Joe, the boat owner, was in his late thirties and was alone for the weekend. He was married, but his wife was at their town home. I had a great time with them on the water, and Joe invited me to a party that night where I stayed very late. The house was full of people sleeping everywhere, and I ended up in Joe's bed. I had a bad sunburn, so he offered to rub lotion on my back. I thought it was a bit strange, but it felt really good until his hands started to wander to parts of my body that were not sunburned. I guess there was fear but also curiosity as I let him play with my private parts until I ejaculated. He then wanted me to reciprocate but I pretended to fall asleep.

The next day was more of the same water sports and partying. That night I was a little drunk and ended up in Joe's bedroom again. I looked in the closet and saw a beautiful nightgown made of cream colored silk and lace. I couldn't resist the temptation to put it next to my body and feel the smooth coolness caress my skin. I was so lost in the sensation that I failed to notice Joe enter the room. He startled me by asking if I liked the gown. I said it was beautiful and that his wife had very good taste. He asked me if I wanted to try it on and said it would feel good on sunburned skin. He said go ahead and wear it to bed that he would lock the door and no one would see me. I stepped into the gown and it felt so incredible that I started to get erect.

In bed Joe took up where he left off the night before. He started to caress my body through the smooth fabric of the gown. His hand moved up and down my torso and legs until he found my cock and started to play with it. This time however he stopped and told me he wanted me to play with his cock like his wife does when she wears that nightgown. I was very turned on by his caresses, and he was already hard when I reached down. His dick was larger than mine and covered with big veins supplying blood to his turgid member. I jacked him for awhile and was enjoying the way he reacted. Then he started to move up on the bed so that his dick was in front of my face. He asked if I would lick the shaft to make it slippery. This was going further than I had ever imagined and I was genuinely reluctant to go further, but he was very persistent. So I licked the head of his penis while jacking the shaft, but he wanted more and told me to take him in my mouth. I had never imagined going this far, but there I was in a sexy woman's nightgown holding a warm hard cock, so I gently started to suck the head. He groaned with pleasure and started to urge me to take more in my mouth until I was bobbing up and down. He grabbed my head and thrust deeply - choking me and then he groaned and shot his load in my mouth. It was a strange sensation and I was a little disgusted, so when he pulled out I spit, but the unique taste of his cum remained. He rolled over and fell asleep. I couldn't get to sleep thinking about what had happened, I felt both ashamed and excited.

I finally got to sleep, but was awakened by his spooning me as he kissed my neck. I could feel his erection pressed between my ass cheeks, and I guess he dreamed I was his wife. He woke from his slumber and caressed me while humping me thru the silky fabric. He was very horny and wanted to fuck me, and asked if I wanted to feel like a real woman. I was unsure about going that far, but did not put up enough resistance. He rolled me onto my stomach and started to play with my ass by gently circling my anus with his finger. He licked his finger and slowly inserted the tip which felt strange at first, but I slowly became accustomed to him playing with my anus. He got some lube and finger fucked me, and it started to feel something like taking a dump. He told me to relax and I started to enjoy it. He was massaging my prostate and I came gently wetting the bed. This caused my sphincter to relax and he inserted another finger. After the third finger, I was ready and willing to be dick penetrated. And thats how I lost my virginity.