ISF #3. An Epic Brunette Cigar Girl Closes Down My Evening


It had been quite a first day at the Iowa State Fair back in 2006.  I had scored a bounty of classic sightings over the course of about 10 hours and maintained a pretty good consistency of impressiveness over the course of the day, rarely going an hour without an impressive sighting. If I had ended the evening at 9:30, it would have been a great day, but I always prefer to end the day/night with a bang it if at all possible, and I decided to press on past my foot pain to see if I could end on that elusive high note.  But nothing could have prepared me for what lied in store for me as I approached that 10 p.m. hour…

Sighting #77 of the day came when I was heading to the east side of the grounds, set up on a steep hill. I saw a bright red cherry in the hands of shapely college-age girl only a few yards to the east and began to follow and admire the body of this girl concealed in tight jeans and skimpy halter top. The overweight and unattractive girl accompanying her (who wasn’t smoking at all) made it easy to focus all my attention on the shapely brunette. It took me a couple of moments in the dark of night to notice, but I eventually discovered that this girl was not smoking a cigarette, but a rather a pretty good-sized tiparillo cigar. For me, there is no sexier novelty than seeing a pretty girl smoking a cigar, particularly in a public setting like a state fair rather than some seedy bar.  The small cigar trend was by and large in its infancy in 2006, at least in the Upper Midwest, so this was one of the first cigar sightings I was fortunate to take in, and in this case, with as perfect of a vantage point as possible.

After this bombshell revelation, I began to follow at even closer range, enabling me to ingest as much secondhand cigar smoke as possible. Every pungent whiff felt as though it was heaven-sent as it splashed me in the face. From there, the already astounding sighting got even better as the two girls stopped at a lemonade stand to purchase a beverage. There she stood, cigar in hand, buying her lemonade. I couldn’t tell whether the young girl in the booth took notice of the cigar-wielding babe she was serving, but I was thinking to myself that I would have given anything to be that girl in that lemonade stand selling a drink to this cigar-chomping hottie…..

After the lemonade purchase, the girls proceeded up the hill to a crowded area near extreme rides. As they weaved their way through the crowd, a number of people took a second look upon getting a noseful of cigar smoke coming from this attractive young lady. As if it was the most normal thing in the world, she stood amongst this crowd dragging on her cigar without the slightest hint of self-consciousness. Standing there admiring her with her shameless chutzpah for this incredibly public cigar-smoking display, I was extremely close to approaching her and requesting a date. I’ve never been good at that sort of thing, but a situation like this comes up so rarely that I nearly forced myself to proceed. Then I started to evaluate this situation a little more closely. Here we have a butch looking girl in the company of a female cigar smoker….not exactly the most heterosexual union I’ve come across in my day. The more I thought about it, the more I feared tremendous embarrassment if my date request was met with the revelation that the girl didn’t swing my way so I think I made the right call, not that I was in any way assured of finding the nerve to ask her even if not for the lesbianism observation.

Determined to go out with a bang, this unpredictable girl carefully snuffed out the cherry on her two-thirds smoked tiparillo and then stored the remainder of it in her the back pocket of her jeans (don’t ask me how it even fit back there as tight as the jeans were), apparently saving it for later. Moments later, the girls turned around and walked away from the scene, passing me at close range and providing me one final chance to ask the girl out that I let pass. I kicked myself for weeks for letting this opportunity slide, but my instinct was probably right and I was able to relive the scene in my fantasy for months to come.

Not only did this sighting allow me to wrap up my day at the Iowa State Fair in style, it also gave me one of my best cigar sightings of my life, and definitely the best at the Iowa State Fair.  I realize they’re not for everyone, but something about cigar sightings points to a girl with a deliciously naughty streak that I find irresistible, and this girl was near the top of that list.

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