Earlier I wrote about how I had gone to see my friend Jane at the college she attended in Massachusetts and ended up being tricked into losing a game of pool, with the result that I had to strip for her and her sorority friends. 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. She was tall for a woman, being about 5'8" and though she weighed about 150 pounds, she wasn't fat. She had soft brown hair that she wore just shorter than shoulder length, and big brown, doe-like eyes that would sparkle when she smiled, giving her a bit of devilish look. She also had a great figure with prominent, but not overly large tits that she would often accentuate with button up blouses that were a bit on the tight side. Her hips and legs were very shapely and she would sometimes where heels that really showed her legs off well. More than once I felt my cock responding as I watched her walking down the halls of our high school. The year before this particular summer we had taken a school trip to New York and were walking on Broadway when a young guy walking passed us the other way, leered at Jane and said, "Now that's eating pussy."
Jane looked at me and asked, "What did he say?"
I totally agreed with him, but was too embarrassed to repeat for her what he had said. Actually, at that point I hadn't had the pleasure of licking a pussy and so I truly didn't know if I agreed with him, although later I'd find out that eating pussy is an incredible turn on for me and something that I would always do for a woman.
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, so it was just Jane and me. 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. We lived in a small town about 90 minutes west of Boston. 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 said, "It's such a nice day today. Let's 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 and started to take off her shoes.
I was feeling really self-conscious, I've since learned that I have social anxiety disorder, and not at all sure about the idea, but since she appeared to be undressing, I went ahead and undressed down to my underwear.
Standing there in my Fruit-of-the-Looms white briefs with my cock pushing against the front of them, I looked over at Jane who was standing with her hands on her hips and one of those big devilish grins on her face wearing a one-piece bathing suit. 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, my cock rapidly engorging with blood. 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.
Breaking the surface of the water, she came up with them, shaking the water from her head and laughing loudly as she threw them up toward shore where they landed in a tree.
