First Ever Touch From Older Woman

I want to share an experience that may be the most erotic of my life when I was younger. My parents worked a lot so they would hire a girl with a car to drive my two sisters and I to sports and appointments. One particular girl, Janet, was a family friend. She was 24, about 5' 5", 125 lbs, sparkling blue eyes, large breasts that hypnotized me and wavy hair that fell to her shoulders. She was a very pretty girl and very outgoing. She was a second grade teacher and also taught figure skating to my two sisters. She was also a perpetual flirt. I had an enormous crush on her. She egged me on by flirting with me. One winter my sisters and I were dying to go skiing. My parents couldn't get away so they asked Janet if she'd take us away for a night and a couple of days of skiing. My sisters both adored her so we were all excited when Janet said "Of course! I'd love to"! My mother made a hotel reservation for us and I couldn't wait to spend a couple of days with Janet! The first day, we drove a couple of hours north to get to a ski area. We skied all day and then headed to our hotel. The room had two double beds and we also got a rollaway cot which was set up between the two double beds. Since I was the only male, I got the cot. Janet was in one bed by herself and my sisters shared the other bed. We were all getting ready for bed and the one bathroom always seemed occupied. I got changed in the corner of the room when Janet was in the bathroom. I changed into my pajama bottoms but she came out of the bathroom when I had my shirt off. I played a lot of sports and I was in very good shape. She walked by very close to me and complimented my upper body. She was ready for bed and had on a very thin flannel nightgown. It was very obvious that her bra was off as her nipples made a large impression on the fabric. I couldn't tell if she was wearing panties but I couldn't see any lines. As she was moving around the room organizing her things, she would lean over in front of me. I'm sure this was intentional. I didn't get a peek at her nipples but I got some great views of her cleavage. We all got into our respective beds and after some TV, we shut out the lights and went to sleep. I wanted to jerk off before sleeping while thinking about Janet's breasts but the room was too crowded. Since we were all exhausted from skiing, sleep came quickly, even without a wank. That was not easy with my goddess laying three feet from me. Sometime during the night, I have no idea at what time, I felt a hand in my hand. It took me a couple of minutes to realize where I was and what might be happening. As you can probably guess, it was Janet's hand in mine. I was excited, scared and nervous at the same time. I moved my fingers on her hand but there was no response. I squeezed her hand and stroked it with my fingers but still no response. I didn't know if she accidentally grabbed me in her sleep or if it was something more. I wanted to find out. I continued to hold her hand but I rolled onto my side and reached out to her with my other hand. I touched her hair and lightly stroked her cheek. Still no response. I probably did this for five minutes while trying to decide what to do next. I got a little bolder as I woke up more. I ran my fingers across her face and put my finger between her lips. I had little experience with girls at this time so this was incredibly exciting. My finger went into her mouth a little bit but her hand still didn't move and she showed no other sign of being awake. My cock was fully awake though. It was telling me to try something else. I looked over at my sisters and they were both still asleep. I lightly touched Janet's shoulder through her nightgown. Those breasts I had fantasized about for so long were now inches from my touch. I got braver and let my hand drop down her body. I was very scared that she would suddenly wake up and discover what was happening. I also had conflicting thoughts that she was just pretending to be asleep and realized everything that was happening. My hand was now on top of one her breasts and I could feel the warmth, the heft and the softness through her nightgown. It was amazing. I didn't dare let my other hand release her hand in case it broke some type of spell. I was in an awkward position leaning over to touch her breasts but I needed to go a little further. I put my hand into the open neckline of her nightgown. I now had my hand on her naked breast. It was not easy to move my hand in the restricted opening but I managed to feel each breast and run my fingers over the first nipples I had ever touched. There was still no visible response or reflex from her. I reasoned that she had to be awake but I still couldn't be sure. I rubbed her tits for a few more minutes before it felt like my cock was going to explode. I lost my senses and rolled on my back. Janet's hand was still in mine. I moved my body up my bed and pulled my pajama bottoms down. I took Janet's hand and put it on my hard cock. This was the first hand to ever touch my erect cock. Her hand cupped my cock and I was hoping that she'd now end the charade and stroke me. She still remained motionless but her hand stayed on my hard naked cock. I decided to take matters into my own hands, pun intended. I put my hand around hers and moved it up and down my cock. I made her cup my balls and then continue to stroke me. She remained otherwise motionless as my hand directed hers to masturbate me. It didn't take too long before I came. I left her hand there long enough for my cock to go limp, savoring the moment. After my orgasm, I came to my senses and the nervousness returned. I was afraid my sisters would see something or Janet might actually really be sleeping. I cleaned up as best as I could, put Janet's arm back onto her bed, pulled the covers up and eventually fell back asleep.

In the morning, I was worried about her reaction and I was a little afraid about being alone with her. She gave no indication that anything happened during the night which confused me further. I didn't think it was possible for someone to sleep through everything that happened. We skied again that day and at one point while waiting in the lift line, Janet and my sisters were talking about boys. Janet looked at me with a slight smirk and said at least we know YOU like girls. I was speechless and tried not to give anything away by my expression. The conversation didn't go any further than that one line but at that point I knew she had been awake that entire time. I guess she needed to have some plausible denial just in case. Nothing ever happened like that again but as I got older and had more sexual experiences, I always wondered if she masturbated after I came and how far she would have let me explore that night. To this day I regret not pulling her covers back. She probably had her nightgown around her waist and her pussy would have been exposed and waiting for me. Although it was an incredible experience I wish hers would have been the first pussy I ever touched