Tom Gets Naked for Jane

Earlier I wrote about how I had gone to see my friend Jane at the college she attended in Massachusetts and ended up naked for most of her sorority sisters. I should really have been smart enough to suspect that I was being set up because Jane had a history of getting me naked for her and her friends' pleasure. The first time that Jane got me naked was the summer before we headed off for college. There were four of us who had known each other for about 12 years and had hung out together, 2 guys and 2 girls, pretty much just friends even though I did like Jane and hoped it might become more. Jane was about 8 month older than me, but physically she was always mature and easily could have passed as being in her early twenties. The year before we had taken a school trip to New York and were walking on Broadway when a young guy walking past us the other way looked right at Jane and said, "Now that's eating pussy."

Jane looked at me and asked, "What did he say?" but even though I agreed with him I was too embarrassed to repeat for her what he had said. Actually at that point I hadn't had the pleasure of eating pussy and so I truly didn't know if I agreed with him, although later I'd find out that eating pussy was an incredible turn on for me.

Well that summer Bob left town to start college early and Robyn went to spend the summer working as a nanny for relatives out of state. One day Jane phoned and told me to come over to her house. Her family had just moved into a new house out in a wooded area of town. Her father was an executive at a woolen factory in town and they had a big new house built on a large piece of property. When I got there Jane was outside and said, "Let's take a walk in the woods."

We followed a path from the back of her yard into the woods till we came to a small secluded pond and Jane suggested that we go for a swim.

"I'd like to but I don't have a swimsuit," I said. I was embarrassed because the truth was that the thought of seeing Jane in her underwear or better yet naked was getting me excited.

But Jane said, "That doesn't matter," and sat down to take off her shoes.

I was feeling really self-conscious and not at all sure about the idea, but since she appeared to be undressing I went ahead and undressed down to my underwear. When I looked over at Jane she was standing with her hands on her hips and a big grin on her face wearing a one piece bathing suit. Jane was cute and had a very nice body. She was about 5'8" with muscular legs and big tits. Her bathing suit was very tight, low cut and came up high on her hips. She had large nipples and they were very visible as she stood there grinning at me in my underwear. She ran to the water and jumped in calling for me to follow. Jane was a really good swimmer having had lessons most of her life and also having been on a swim team in Worcester. I was barely adequate at best. I'd had some Red Cross lessons, which back then meant I learned the crawl, back stroke and side stroke, but I seldom had much opportunity to practice.

While we swam Jane would dive under the water and swim around even going between my legs several times. Once she went under for a long time and I was starting to get nervous when I felt her behind me grabbing my underwear and starting to pull them off. I pulled my knees up to try and grab them but since she already had them down past my knees that just helped her to pull them off more quickly. She came up with them, laughed loudly and then threw them up toward shore where they landed in a tree. She dove under a few more times again swimming between my legs, a couple of times she even touched my balls. I wasn't sure if it was accidental touching or not. Then she swam to shore and walked up to where her clothes were. She stood there with her legs spread and used her hands to wipe the drops of water off her body, which made her boobs bounce and her nipples stand up. Watching her I thought she was really beautiful and started to get an erection. After a couple of minutes she called to me to come out. By now I had a full on chubby and so was even more reluctant to come out. I stood far enough out so that the water came up past my waist hoping my erection would go away.

"You'll have to come out eventually," Jane said and so feeling more embarrassed than I ever had and keeping my hands over my cock and balls I walked up to where Jane was and stood in front of her. Jane looked up at me and smiled then reached up and moved my hands away from my crotch looking at my cock and balls. Having her look at me just got me more excited and my cock, which had started to go soft, stiffened standing straight up along my abdomen. After looking at me for a bit she put her hands on my hips and twisted as she said, "Turn around so I can see your ass."

When I was facing away from her she put her hand between my legs, pushed on the inside of my legs and said, "Spread your legs some more."

I moved my left foot to side a bit, but she said more and pushed harder on the inside of my thigh. Her hand was very high on my legs, almost touching my balls and I was really aroused.

After Standing there for a couple of minutes, she said, "Bend over."

I bent forward a bit, but again she said, "More. Put your hands on your knees and your head down by your knees too."

She slid her hands to my ass cheeks and pressed lightly spreading my cheeks. After a minute or two she turned me again. While I was standing there with my hard cock bobbing up and down she took my hand and put it on my cock. She then slowly took my fingers and wrapped them around my cock and then started to move my hand up and down. She stopped and so did I.

But she said, "Don't stop. Keep going."

Then she took my other hand and turned my fingers and pressed them against my balls. I was really excited and within just a couple of minutes I had the strongest orgasm I had ever had - almost hitting her in the face with my come.

Jane smiled and laughed and I could feel myself getting red with embarrassment. We stayed there for awhile longer with me still naked and doing different things for her. Once she made me walk and then run back in forth in front of her. Then she had me get on my hands and knees facing away from her, and again she told me to spread my knees very wide. As I knelt there with my legs spread I felt her lifting up balls and looked between my legs to see her using her foot rub my balls and cock. I was fascinated by the sight of her pretty foot massaging my balls and quickly got hard again. She moved up to the side of me and told me to masturbate again. As she was to the left of me I used my right hand to stroke my cock so that she could see everything. As I neared climax I closed my eyes and lifted my head and just then I felt her hand come around from behind, grab my balls and squeeze them lightly. Just as she did I had a very powerful orgasm. As my orgasm subsided I put my head down in the sand and lay there. I was embarrassed to think of myself lying with my ass up in the air and my legs spread for Jane to see, but was to overcome at first to change my position.

Finally we got dressed and left. I didn't understand why I would do everything she asked of me even though I found it embarrassing, but I did and that wasn't the last time I was naked in front of Jane.