These stories are based on and inspired by experiences with the real life Captain O'Malley, a beautiful and sensual woman who taught me much. I'm using as many stage names as I can so that only those people that were part of the story are able to tell true identities and changing real names where no stage names are available.
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"ROMANCE WARS. A great way to meet new friends this festival season. Woo your target and try to find who's wooing you."
"Sounds interesting Radu, how many people you got signed up? It's gonna be pretty boring if there's only five guys doing this." I said as I read over the flyer.
"Actually there are only five guys signed up so far, but over thirty girls signed up including the Wenches Guild. I'm having trouble finding guys that can keep up with them." Radu replied mischievously.
"Wenches guild? I'm in. I can handle anything they throw at me." I grinned. The Wenches guild was known for their beauty - the fullest bodices and corsets, and a flirty streak ten miles wide.
"Just get this back to me tomorrow. The wars start next Saturday. I hope you survive." I heard Radu chuckle a little as he left the flyer and signup sheet me with and walked away.
It was the first week of Faire and everybody was catching up with each other on events over the year, getting to know the rookies and generally getting into our roles, not only in the kitchen we all worked in, but also in the characters that we played at Renaissance Festival. Doug, one of the rookies wasn't very excited about the idea of romance but liked the idea of a possible booty call during Festival. The other rookie in the kitchen, a cute little blonde we'll call Foo, was very excited. She had never had a boyfriend and we got the feeling that she would fall madly in love with whoever she got paired up with, which I hoped wasn't going to be me. Me, I was single, playing the field if you will. I had a couple girls lined up if I wanted to go out and have some fun, but nothing romantic going on. I was still trying to deal with how things ended with my late fiancé, and thought Romance Wars would be a good distraction from her. Little did I know the ride I was about to embark on would be one of the wildest in my young life.
I was 20, relatively fit aside from my chronically scrawny arms. The rest of me was solid muscle and I even had a six pack. I had been with several girls and had never failed to bring them to orgasm. I felt quite confident in my bedroom skills, and admittedly a little bit cocky. I was about to find out there's a big difference between girls, and women.
I filled out my signup sheet answering questions like my favorite colors, favorite animals, music and movie preferences, how long and where I worked at Faire, so on and so on. I found it interesting that it asked a lot of questions about me, and absolutely no questions about what I was looking for in a romantic partner. I found myself wondering about how Radu was going to pair people up without knowing what they were looking for.
On the back of the flyer were the rules, at the top, and in big bold print was: "No trading." If you had problems with the person you got paired with then talk to Radu and he would make a decision on changes. Only he would know who was wooing who. We could keep our identities secret if we chose, but had to reveal ourselves at the cast party at the end of the year. You must make contact by the first weekend of Romance Wars and at least once every week after that. No stipulations were made as to how you made contact. Roses from the flower girls would be discounted and could be delivered by the flower girls that roamed the faire, but tipping of the girls for the delivery was required. The Wenches Guild would also make deliveries and tips were required for them as well. Ok simple rules, not so simple a game.
The next week I got a signup sheet back from Radu. I was hoping to get a member of the Wenches guild but wound up with an 18 year old girl who actually worked just one booth over from me. This would make it easy to deliver my presents, but made discovery an ever-present threat as I was planning to keep my identity a mystery until the cast party at the end of the season, a little more mystery and romance that way. And it gave me an exit option if I didn't end up liking her.
I found that Abby liked Limp Bizkit, gargoyles, romance movies, and her favorite colors where Orange and Blue. Obviously her favorite sports team was the Broncos. Well at least we had one thing in common. The biggest advantage was that she was a rookie; she wouldn't have figured out the various social circles and wouldn't know who was working what booths. I already had several contacts that I could use for scouting and observing and she would be none the wiser, at first. I would have to develop some new contacts so that she didn't see the same people hanging out around her booth for no particular reason. She didn't work a food booth and someone constantly looking at chainmail would have aroused suspicion, especially when little gifts appeared along with them. I decided to go with the Gargoyle thing and add in a few witty poems to go along with them, see what happened. If she didn't like it, I could change my approach. I wrote a poem, bought a gargoyle and had a friend deliver it. I arranged the time for delivery so that I would be there to watch her first reaction. I could go by once, maybe twice before she figured out I really wasn't interested in armor.
Her first reaction was rather bland and to be honest, I wasn't all that flattered by her as well. Way to much the punk rocker chic and I really wasn't into her that much. Oh well, play the game out. Heading back to my own booth I was caught off guard when I noticed Doug point me out to two very beautiful women. One was a tall, very well put together blonde. I didn't know her that well but I had seen her around faire a few times and knew she worked the ticket booth. The other woman was a flat knockout. She looked to be about 30, strawberry blonde hair, long muscular legs and boots with just enough heel to show them off, but still be comfortable to stand in all day. Her breasts, though tightly confined in her corset where round enough to show that they didn't need help being held up and were quite naturally large. She looked at me and looked at a small wooden box. The look in her eye told me it was meant for me, I hoped it was from her. I found myself standing straighter and tried to nonchalantly pull my sleeves down to cover my scrawny, nearly sun burnt arms, cursing my Irish complexion.
"Are you LLiam?" the strawberry blonde asked.
"I am, and you are?" I asked while taking her hand and giving it a gentle kiss.
"I am Captain Elsbeth O'Malley of the Wenches Guild, this is my First Mate Donna, we have a present for you" and held out the little box. Opening it I found a note tied with two pieces of ribbon, one maroon and one teal, "A Romance Warrior has requested your company for a chaperoned dinner tonight. Return teal to accept and maroon to decline. Your messenger will have the details regarding when and where to meet me. You may wear your street clothes but I would feel more comfortable if you attended in costume as I will be in mine." Thinking it was quite sudden but curious, I took the maroon ribbon and tied it to my dagger, retied the note with the teal one and with another kiss on Captain O'Malley's hand told her that I accept the invitation. She told me to meet her and my warrior in front of the ticket booth after closing cannon and things would go from there.
As she was going along to chaperone, I was told that not being a proper gentleman would have rather dire consequences. One of the other things the Wenches Guild was known for was being the best armed women at faire as their characters all revolved around pirate women. Captain O'Malley was wearing a cutlass, and three separate daggers on the outside of her costume, no doubt several more hidden discreetly in strategic places, waiting for some poor dumb fool to do something stupid. Donna was similarly armed. After Donna flirted with Doug for a few more minutes the two of them departed and left Doug a clue as to whom his warrior may be. Opening his clue he discovered a nautical telescope wrapped in a treasure map with an X next to a heart.
"Wonder if my warrior is the Captain," Doug mused.
"The First Mate was in charge of Navigation on pirate ships cluedart," I replied, "Donna's your warrior."
"I've always liked blondes, and she is definitely a top notch girl."
"They've done nothing but break my heart; you can keep her if you can get her. I'm more curious about mine."
"What about your date with the captain? She's a bit old for you."
"Captain is only the chaperone. I guess I'll be finding out who my warrior is tonight. I doubt she's a member of the guild though. A wench wouldn't need a chaperone. She'd have no qualms about running me through right there in the restaurant if I wasn't well behaved."
"Hope you survive the encounter, that captain is definitely the kinda girl to do just that."
I couldn't help but wondering about Doug's frequent use of the word 'girl' when referring to Captain and Donna. Keep that up Doug and you might be the one getting run through I thought to myself.
After a cannon blast announced the end of the Festival day, I quickly cleaned myself up and started to make my way down to the front gates. I was still wondering who my warrior was when I spotted Captain O'Malley waiting by one of the gift booths. Walking up to her and announcing my presence, (it's not only impolite to walk up behind someone and startle them, it's also hazardous to your health to startle a woman as well armed as the captain), she turned to look at me.
"Well LLiam, you certainly are prompt, I appreciate that in people."
"Thank you Captain, My eldest sister is chronically late and it annoys me to no end. Maybe as compensation I try to be on time if not early," I replied.
"Well then, I have good news for you and I'm afraid I also have some bad news," she said with a serious look in her eyes. Uh-oh, this isn't going to be good. "The good news is that a chaperone will not be required this evening, unfortunately the bad news is that your warrior has had an emergency and will not be able to join you for dinner."
Well shit I thought, I had already sent my carpool home, and though I had asked my folks to bring my Jeep up, they wouldn't be here 'til much later this evening. I was stuck.
"Does this cause problems for you LLiam?" Captain asked. I noticed the green in her eyes as she looked at me, her concern was actually genuine. I explained my predicament and she understood.
"Well Captain O'Malley, do you have any plans for dinner? If you have a car, I'll buy."
"Is that your normal method of asking someone on a date lad?" Captain O'Malley asked, "I must say that it's not very original."
I could feel the red hue in my cheeks as I found myself blushing, "Well not my best approach, but I must admit that it has served me well in the past."
"Honesty and confidence, a touch of humility, and general good looks. I can work with this. I accept your offer LLiam, give me a few minutes to conclude ship's business and we shall be away."
She chatted with Donna for a few minutes while I waited a respectable distance away, a couple quick glances in my general direction their only acknowledgment of my presence, although I did distinctly hear Donna mention something about 'your new cabin boy' which piqued my curiosity. They finished their discussion and Captain O'Malley turned to walk to me. I took a few steps forward and held out my elbow for the Captain to hold on to.
"My pickup is down in tent city. We'll be able to leave once they open the gates." The campground on the Festival site was where most of the performers and merchants stayed during Festival. Most of them traveled state to state following the fairs as their main source of income. Most of them had very nice RV's ranging to custom made tour buses fit for a movie star. Cast and crew could also camp there overnight as we came from all over the state and the drive home could be hell after a hot day. A lot of people chose to stay in tent city. Captain O'Malley was about six feet tall in her boots and I figured she would about five nine without them. Strawberry blonde hair and emerald green eyes, I would come to lose myself in those eyes time and time again in the months to come. Her facial features were delicate yet had a seriousness about them that made her flat out beautiful.
Her shoulders were slightly wider than you would expect to find on a woman her size yet exuded a confident femininity. Her walk was that of a woman who commands the respect of those around her. Walking down there with Captain O'Malley on my arm I felt ten feet tall. Instead of a date with a probably twenty something or teenage girl, I was actually going to dinner with a magnificent example of womanhood. I had always had a thing for redheads and on a scale of one to ten, this one was a twenty. We walked into what I would come to know as wenches' camp, most of the women in the guild were there and in various stages of undress. There were at least a dozen of them but they all seemed to be gathered around one RV in particular.
Captain pointed to a small Toyota pickup, "That's mine. Wait for me there will you, I have a few more items of ship's business to check on and then we'll be ready to go." She walked over to the RV and spoke to a petite blonde.
