Does It Fit?

It was a warmer than usual day. I was wearing shorts and a button down short sleeve shirt with sandals on my bare feet. I was walking down the street and I bumped into an old high school classmate of mine. She was standing outside of a downtown boutique store she worked at. Being mid day on a weekday the business was slow as not many people came into her store that time of day. She saw me and perked up with a smile and said hello. She asked where had I been and what was I up to these days.

It was difficult for me to answer her twenty questions while staring at her small frame body dressed in a mini skirt and half button white blouse. She stood in the doorway of the shop fanning herself as if it were hotter than hell out. It wasn't hot, just warmer than usual that day. She asked if I had some time to step inside and chat with her awhile. I looked down at my watch and said sorry I have a meeting I have to get to down the street and could not stay. She ushered me into the store and then into the managers back office.

As she sat down on the chair I could see that her skirt was so short that it did not have enough fabric to lay under her butt as she sat in the chair. Instead it hung down freely behind her chair. She began another twenty questions about whether or not I had any deep feelings for her back in high school. Instead of answering her I asked her what that line of questioning was all about. She said it's been years since we have seen each other, and may be years before we meet again. She didn't want to wait until then to find out the truth from me. She reminded me that I had a meeting to get to and didn't want to beat around the bush. She just wanted to know if what she had been thinking all these years was true or not. I asked her what exactly was she thinking all these years. She replied that she thought we would have made a good fit with each other. She then winked that special wink with a devilish smile. I took the hint and replied that I thought it would have fit perfectly fine, as I smiled and winked right back at her.

She took the tone in my voice to ask what exactly did I mean by that. I reached down and adjusted my growing hard on in my shorts and said it would fit just fine, I am sure of it. She said she wasn't too sure herself and asked what we could do to find out if it fit or not. Stunned by this, I began to ask if she would please clarify herself but was cut off by what she did next. She spread her legs apart and hiked up her tiny skirt to reveal she was not wearing panties and her neatly trimmed landing strip pointed at her tiny pussy. She says if that, pointing at my dick, would fit in here, as she points her finger into her pussy lips.

I was heating up at the sight before my eyes. I said there is one way to find out and went to unbutton my shorts. The shorts took a clue from gravity and fell to the floor. I stepped out of them and started to gently stroke my cock as if to prepare it for what was about to happen. I stopped after the third stroke and held my cock at the base and gently squeezed while pushing it out to make it grow all that much more bigger in front of her face. She stood and with a twist of her thumb and fore finger at the waist of her skirt the skirt fell to the floor. She sat back in the chair. leaned back and raised her knees towards her head. She reached down and with the three middle fingers she stroked her pussy as the middle finger dipped deeper into the folds of her lips.

As I leaned into her to insert my cock into her small framed pussy she reached out and pushed me back and asked, what no condom? Sorry my dear she says but you are not entering me with a loaded cock without some form of protection. She said she did not want to get pregnant. I informed her it would only be a quick in and out anyway as we just wanted to see if it would fit or not. Plus I told her I am kind of seeing someone now and I wouldn't cheat on her. Sticking my dick in to see if it fits is not considered cheating if we are just taking a measurement. (Gotta justify it somehow, right?)

She then sits upright and says she is an expert at jacking guys off and she will unload my cock before I stick it in her. She wraps her small hand around my engorged cock and starts to stroke it. She then reaches up with the other hand and makes a complete circle around my cock and she now looks like she is warming her hands over a fire, rather than stroking my cock. Her small frame body matches the small hands and her gentle touch is enough to cause me to lose my load within about thirty seconds of her stroking. My cum flies up over her head and lands on the floor behind her, it hits her chest and arm as the last spurts dribble out and land on her leg. She smiles and says that's the best part of stroking a guy off, then says she will clean it up later.

I gently push her back in her chair and stick my finger into her pussy and can tell she is wet and ready for my cock to enter her. I lean in to put my dick in there.

The alarm clock goes off and wakes me up, the dream is over.