This is a very hot topic and something which has happened to me a lot actually. Here's one that happened while I was in college:
During college I rented a room in a large house with several other students. One of my housemates was Caroline, a 20 year old Communications major who happened to go to the same school as me. Since we had the same schedule we would usually meet after class and walk back to the house together.
After class one day we walked home and were talking about a course we had both taken, and for whatever reason I followed Caroline into her room to continue the conversation. As we continued to talk I noticed Caroline getting out her workout clothes and laying them on her bed.
At this point, Caroline interrupted our conversation to say, "I have to go out for my long run before it gets too late. Do you mind if I change into my running clothes."
"No, go ahead, " I responded, thinking she would go to the bathroom down the hall to change.
There was an odd sort of pause and I thought I heard Caroline give a short sigh before she reached down and started to pull her sweatshirt up over her head. She set the swearshirt on the bed and I expected her to leave. Instead, she started to casually take her t-shirt off, then her shorts, then her bra, her panties, and even her shoes and socks.
My jaw dropped. In less than a minute Caroline had gone from being fully dressed to standing in front of me barefoot and bare assed, making no attempt at all to cover herself.
Whether I intended to or not, I could feel my eyes darting all over her suddenly naked body, taking in every detail of her anatomy. Caroline was slightly taller than me, about 5'9", and despite having large breasts and wide hips, her stomach was very flat. She was naturally light skinned, but was lightly tanned with barely visible tanlines around her chest and nether regions. She had shoulder length golden blonde hair which framed her face beautifully but did not hide her breasts. Her breasts themselves were very large and full, sagging only slightly without a bra. Her nipples were small and pink.
After taking a moment to view her nudity in its entirety, my attention focused almost immediately on the space between Caroline's legs. Since I had met her, I often wondered if she was a natural blonde and whether or not she shaved her pussy. Well, I did not get an answer about her natural hair color because her pussy was shaved bare.
I tried to keep talking and not just stare at Caroline like a pervert while she dressed in her running clothes. Altogether she was naked in front of me for about two minutes before she left to go on her run. It took me several minutes to compose myself after Caroline had left. Watching her casually strip down to a state of total nudity in front of me was both shocking and erotic, certainly not something I would have ever expected from my her.
Back in my room I made a vain attempt to open my books and study but spent the next hour thinking of how to handle what had just happened. Was Caroline disrobing meant to be an overture to me? What if it wasn't? Was this something she had done around our other housemates? Maybe she was just more casual about her nudity than I expected her to be?
Downstairs I heard the front door open and knew it was Caroline back from her run. I decided that I didn't want to be creepy, but I did want to find out just how far this could go. So, coming up with an excuse, I walked down the hall and poked my head into Caroline's room.
"Can I borrow one of your theory books?" I asked. "I need another source for a paper I'm writing."
Caroline invited me into her room to look for the book and while I searched her bookshelf I asked about her run: where she went; how far she ran; if there were any races she was getting ready for; trying to stall for what I hoped would come next.
After a few minutes of this Caroline announced, "Well, I really do need to shower."
"Go ahead," I told her.
There was a moment's pause where it looked as if she was waiting for me to leave the room. When I didn't, she let out another little sigh and began peeling off her workout clothes until once again she was standing butt naked in front of me.
After that, she grabbed a towel from her closet and then walked naked down the hallway to the shower, never covering up once, despite the fact that some of our other housemates were also home and could easily have seen her. By now it was clear that Caroline had no problem with me seeing everything.
Despite my desire to see where things might lead after her shower, I decided not to push my luck any further and returned to my room.
The next day, there was a slight awkardness in our conversation as we walked to class.
When we were leaving the campus, I finally asked Caroline, "Can we talk about yesterday?"
"What about it?"
I decided to try being straightforward and told her, "I was really impressed when you took your clothes off in front of me yesterday. I was impressed with how comfortable you were being naked, and I was also impressed with how good you look naked. "
I looked over and noticed Caroline blushing slightly. "I never expected you to just undress in front of me like that, but," I looked over and saw that Caroline was blushing an even deeper red, "with a body like yours, you have every reason to show it off."
She was silent for a moment and I began to worry that I'd said the wrong thing.
Finallly, very softly she said, "I was impressed with you too."
After another pause, she added, "Please don't tell my boyfriend. "
After that, Caroline was casually naked in front of me almost every day for the rest of the year that we lived together; she would dress in front of me before class in the morning; she would undress in front of me before her run and before she showered; and she even tried on outfits and asked my opinion before going out on dates with her boyfriend.
Towards the end of the year she got bolder; by then she was always naked in her room and would invite me to study with her sometimes; she would even walk out of her room naked to my room at the other end of the hall just to talk or hang out. During spring break when the rest of our housemates were out of town, I even convinced her to answer the door naked.
As far as I know she never did this with any of the other people we lived with. She also, unfortunately, stayed with her boyfriend the entire time we lived together. This was very frustrating for me but I think also part of the fun for her.
In the end we had a very fun, sexy, complicated friendship.
Although we did not live together after the year was over, Caroline and I stayed friends and eventually she broke up with her boyfriend which led to many much more adventurous experiences with her.
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