Crazy Tall and Pigtails

This is a fictional account with everyone over eighteen.

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I was out the door so fast Monday morning that I don't remember eating breakfast or even dressing. Though, it's possible it had nothing to do with how I hurried to work; rather my brain still trying to unravel my feelings for all the women I suddenly had in my life. The irony was that a month earlier, I was a virgin with no women unrelated to me in my life, and now I had three beautiful women I couldn't wait to see more.

I thought just a week ago Anna was the love of my life and I could be happy forever with her. Then along came Monica and Katie and my new world was upside down. Anna might still be the love I wanted, but events and new relationships had brought doubts to what I thought would always be solid ground with her.

Monica was back home and just a half hour drive seemed like the other side of the Earth. I couldn't get her smile or body out of my mind though. Katie was much closer, but her bond with Darci built obstacles around that going much further. Each new relationship had baggage that made the complexity of the situation seem enormously complicated.

All this scrambled through my mind as I laid down the lines on one of the softball fields. I looked back towards home plate from first base to see how straight I'd held the line. Not my best effort and I would need to concentrate a bit more as I finished.

I'd hoped to see Anna at the main office of the park district as I punched in that morning, but my supervisor immediately assigned me to the sports fields five miles away for the day. I'd done this work for a couple years and was one of the best at preparing the fields for play later that day. The field I was working on now would be used by the evening men's softball leagues. I had six more fields to line, set bases on, and groom before finishing in time for all the leagues, men's, ladies, and mixed to begin.

I tried to drive the jumble of feelings I felt from my brain so I could concentrate on my work. I always worried that if I did a bad job it would reflect back on my mom. That was actually a greater detriment to me than what my supervisor thought. Therefore, I was one of the best workers and my boss, Kevin, felt confident sending me out alone to work. Most of the other kids needed closer supervision.

My mom told me that Anna and Penny were working out well. They worked with the pre-school kids enrolled in summer day camps and other events. With the girls constantly on the move like me, it was rare I ran into them. I saw Zach more often as he worked the fields and grounds the same as me. My mom was famous for getting my friends and the neighbors' kids' summer jobs as the park district hired many. The pool alone hired a bunch of lifeguards. That was the best job, but you needed to be certified.

After I got home, I showered before dinner, and dialed Anna's cell. My intention was to meet her for a quickie in the garage like she called me for yesterday. I was feeling horny again after thinking about nothing but the three women since Katie left me last night satisfied for the moment. I called her stretched out on my bed, naked, with only my damp bath towel covering me. I could feel my dick already liking the idea from under the towel.

"Hi, Anna...how you doing?"

"Hi, David. "I'm doing ok, but quite tired."

"Oh, yeah?"

"Yeah, the little kids ran Penny and me silly today. I'm exhausted. I think I'm going to eat something and head to bed after I shower."

"Really?"

"Yeah...sorry, did you want to get together, Babe?"

"Sure," I declared hopefully.

"Sorry...rain check, huh? I'm beat."

"No problem."

"Maybe I'll see you tomorrow?"

"Not likely, I'm doing the Cook Street Park fields tomorrow," I said.

"Well, have fun with that. See ya soon."

"Ok, bye," I replied dripping with sadness.

'God, I hadn't had to satisfy myself in a month,' I lamented as I pondered the thought while lying on my bed. Before that first blowjob from Anna at my birthday party, my hand was my closest friend. It seemed incredibly sad to be going back to that necessity again. I was just deciding whether to do it now or after dinner, when there was a knock at the door. It opened quickly and Darci walked in. Thirty seconds later and it could have been extremely embarrassing.

"Hey, quick knock and entry!" I exclaimed making sure the towel covered parts of me.

"Oh, might I have interrupted something?" Darci asked with a knowing grin. "Lock the door."

"Maybe, you never know."

"I can go out and come back later?" Darci said smirking.

"Not necessary."

"Where's Anna?"

"Tired."

"Oh well, looks like you're stuck with me."

"Your hand?" I proposed smiling.

"You wish. You'll never guess who I ran into today?" Darci said and then offered up before I could even guess. "Ellen...you remember her, right? She and I used to hang out a lot in high school. She was over here lots of times."

"Yeah sure, I remember Ellen."

"Well, Katie and I ran into her downtown. She was with her younger sister, Megan. Megan was in your class wasn't she?"

"Yes."

"Did you know her much?"

"She was in a couple of my classes, but we never really hung out a great deal."

I remembered Megan alright. She was my second crush in high school next to Anna. It might have been because she reminded me of Anna in many ways. Long brown hair, cute hazel eyes, or were they green, I was never quite sure, and a lithe, slender body, taller than Anna and more like Monica. She was smart, very smart, and I think I heard through others that she was going to Penn, another Ivy League school for science; I couldn't remember which kind though, chemistry or what.

Darci was talking again, "We all grabbed a coke together and caught up on old times. At one point, Ellen, Katie, and I were dominating the conversation, so to include Megan, I asked her about some of the people I knew from your class. You'd be surprised how many of my friends had brothers or sisters in your class."

"True, I learned that a while ago from talking to all your friends when they came over."

"So, we're talking about kids in your class and I told Megan we live next door to Anna. I asked if she hung out with Penny and Anna in high school."

"She laughed and said no way! When I questioned her why that was funny, she just said they were in a far different crowd."

"She's right about that," I agreed.

"I guess so, but the way she said it left me thinking," Darci proclaimed.

"About what? Anna was the head cheerleader; she hung out with all the jocks."

"I don't know, but get this. Katie joked about always seeing Anna and Penny in pigtails like little girls. Megan laughed again and said that's the club. Guess what she said when we asked what club?"

"The cheerleaders club?"

"No...The sex club."

"Really?"

"Yeah, Megan didn't know much about it, but an old boyfriend of hers once told her he heard they were hot for sex when they wore pigtails. And that several girls from other high schools were in the club too."

"Seriously?"

"Yeah, and remember I told you the three of them all had their hair in pigtails and a little messed up looking yesterday."

"Yeah."

"Well, I'm just wondering is all," Darci said. "I thought you'd find that interesting."

"It is," I admitted, but didn't say anything more.

"I'm off then...I'll leave you to yourself," Darci said jokingly.

"Funny."

"Hey, get this...Katie thinks you might be packing."

"What! What did she tell you?"

"Oh, nothing much really. Just when we were in the pool the other day she said you brushed up against her. She thought she felt something big going on," Darci exclaimed with amusement.

"Yeah, well, get out of here so I can get dressed."

"Maybe I should just see for myself," Darci said, and grabbed the corner of my towel on my chest and tugged slightly.

"Hey...get out of here! I yelled loud enough to be heard downstairs.

"What...you won't even show your darling sister?" Darci squealed with delight. "I want to see if my little brother is really my big brother."

"Get," I exclaimed, as I tried successfully to pull the end of the towel away from her while making sure the part bunched at my groin remained there.

Darci laughed merrily as she let go and walked towards my door. My mom called from downstairs, "Hey, you two, dinner."

"Another time then," Darci stated jovially and closed the door behind her.

My frame of mind was even more confused now as I got up and dressed. The near exposure that Darci almost caused me was enough to jumpstart my heart in a different way, my dick somewhat too. However, the new comments by Megan, and Darci's suggestions, had me thinking all over again.

It was like everything became crystal clear at that moment. I actually felt stupid for not seeing it earlier...or was it wanting to see it. The whole thing came together in one solid image. It became one gigantic reality. The single crystallizing thought that stood out in my mind came from me fucking Anna the previous morning. When I was pulling her pigtails, fucking her fast and hard, very hard, and she loved it, wanted more, begging me to do what I thought would have hurt her. That image galvanized all the others for me.

Darci kept smiling at me over dinner. Mom and Dad carried most of the conversation. That Thursday was Fourth of July and we had our normal plans to use my Uncle's shore house for the week. They always went away to visit relatives from my aunt's side of the family over the holiday and it was a tradition for us to utilize the house then. It was a great house, walking distance to the beach, and both Darci and I had many wonderful memories of our vacations there. Katie and some of my friends had often come down for all or part of the time. The place could sleep ten people if pressed, like many of the houses along the Jersey shore.

I tried to stay with the conversation regarding the exact plans, but my mind wandered continuously back to Anna. I perked up when I heard Darci talking and caught how she wanted to have Katie come down Thursday to Sunday. She was off from Victoria Secret then. That little gem of information registered with me and I clearly missed the silence that followed after my mother asked me if I planned to bring anyone too. Darci was nearly laughing at me as I came back into the conversation.

"Ah...I might," I said with little real conviction or obvious forethought.

"Well, let us know soon dear so we can plan everything. We've invited the Bartlett's and the Terry's down for Saturday and to stay over the night. You could invite Anna if you wanted?" Mom added, more as a question and offering at the end. "We probably won't have room for many more at least on Saturday then."

"Ah...I ah...she might already have plans..."

"She doesn't go anywhere without Penny," Darci intoned with a smile.

"True," I agreed, but my mind was again racing.

The conversation at that point changed back to meal plans and packing so Darci and I excused ourselves. I could see in my Dad's eye a twinkle at me and also that he could do without the heavy planning my mom was famous for. She loved to be prepared and regretted when she left something behind she should have packed.

"Are you going to invite her?" Darci asked more seriously as we went to our rooms. "I bet Mom and Dad will have you sleep in different places."

"Dad might not care, but Mom will. Especially if she thinks Anna's parents would expect it."

"True," Darci confirmed. "Well, it might be fun, but then again you can have fun with Katie and me too."

At that point, we parted and went into our separate rooms. However, the tone of Darci's voice seemed more pointed than matter-of-fact. I wondered about that as I threw my huge length across the king. God, I felt like I was still growing. My body was back to aching every so often and I would swear my shoes felt tighter again. 'Damn,' I affirmed to myself, I really didn't want to get any bigger.

I slept intermitted that night. One side of me wanted Anna to go more than anything. The other side kept replaying Darci's words about Katie and her. Also, Pete and Zach, had been down the last several years for some part of the vacation. I tried to balance in my mind who I wanted and when, or if at all.

I was tired as I went through the motions of lining Cook Street Park fields the next day. A nap might be necessary when I got home from work. However, I was anxious to see Anna too. I'd decided to invite her for the weekend, minus Penny, and see if she would come. I'd ask Zach and Pete to take a few days off from work and come down Monday to Wednesday. Most rentals along the sure were Saturday to Saturday, but my Uncle didn't rent out his house so we usually stayed a full week with how the holiday fell.

When I finished, I puttered around for a while, cleaning up the equipment before heading back to the main office to punch out. As I parked and walked to the entrance, I spotted Penny saying goodbye to a group of pre-schoolers getting off a bus. As they dispersed I reached Penny. I had to admit my friends were right, she looked hot in her short, white shorts and park district logoed, maroon shirt. The shirts weren't normally what you would call sexy, just a plain collared shirt. However, Penny had the bottom of the shirt tied in a knot off her right hip. The result was a small portion, just enough to be sexy without being inappropriate for work, of her firm tummy showed. Her red hair was back in a small ponytail, most likely due to the heat.

"Hi," I said.

"Hey, Davey...how's it going?"

"Good...you?"

"Not bad...we had a fun time today with the little guys."

"Where's Anna?"

"Her bus is a little behind us. She should be here soon."

"Well, I'm punching out. This heat drained me doing the fields at Cook Street today. I'm thinking about a nap when I get home."

"Not a bad idea or a swim," Penny stated, more it seemed as a wanted invite to our pool.

"Yeah, that might be nice to later," I replied.

I turned to head inside the building to the timer box to punch out. Penny suddenly left the departing kids and walked with me.

"I'm punching out too. Hey, I spoke to Monica earlier on my cell. We couldn't talk long, but she caught me when the kids were all playing the game and I was sitting watching. She says she had a great time when she was here."

"She did? She's nice...your cousin."

"Pretty hot, huh?"

"Yeah."

"She's like a taller version of me don't you think?" Penny asked with a knowing grin.

"There are many similarities," I agreed.

"Ha," Penny laughed. "Ones you like?"

"Of course, I think you look pretty hot today and I'm not talking heat," I told Penny, not holding back a compliment and remembering her tight body.

"Nice...thanks. Hey, maybe we could get together with your friends again tomorrow. I'm going away to Monica's for the weekend, but I wouldn't mind a small party with the boys before going."

"That could be fun. I'm going down the shore for a week starting Thursday."

"Nice...I'd rather do that than go to my Uncle's lake house. Monica's family has a house in Pennsylvania on a lake. Lily Lake. We'll be there most of the weekend."

"Anna going too?"

"Not this time, not enough room as my other cousins are coming too."

We had punched out and Anna still wasn't back as we emerged from the building. I thought about waiting, but was really tired and wanted to take a nap bad.

"I'll call you guys later," I said to Penny as we reached the parking lot.

"Ok."

We said goodbye. I think it was one of the most normal conversations I could remember with Penny. It was like she didn't need to play the jokester when Anna wasn't around. Maybe she felt that was necessary around Anna somehow to maintain her closer friendship. It was only a thought though.

At home I showered, almost a cold shower, and let the water run over me for a little. After drying, I crawled back into my unmade bed. My mother hated unmade beds and since we were around ten it was our job to make our own. Darci was better about it than me, but I still managed to do it most days I wasn't running late for somewhere.

Somehow my mind relaxed and I think I was out in less than five minutes. The next thing I remember was Darci jostling me awake for dinner. It was about seven, but still very bright out with daylight savings time. We had ham and baked macaroni. My mom made great baked macaroni. I ate like a giant hog. With my constant growth, weight was never an issue no matter what I ate or how much.

The table talk was still about vacation. Mom asked if I talked to Anna yet. I noticed Darci's interest peak at my answer.

"Not yet, but I decided I would. I'm going to invite Penny and her over for a swim later and I thought I would ask her then."

"Won't that be awkward with Penny there too?" Darci astutely asked.

"It would, but I happen to know she already has plans to go to her Cousin Monica's house on the lake in Pennsylvania for the weekend. A family thing she has to go to."

"Oh," Darci and my mother said the same.

After dinner I called Anna. I'd let her call Penny if she wanted to come over. Her cell rang like seven times before Anna answered.

"Hi, David."

"Anna, what's up?"

"Napping."

"Still tired?"

"Yes, but the nap helped."

"I ran into Penny earlier. We talked about getting together here for a swim. You up for it?"

"I could...sounds like fun. When?"

"Whenever you're ready."

"I just need to grab a bite. Want me to call Penny?"

"Sure."

"About a half hour then?"

"Great."

After goodbyes, I changed into my swimsuit. I had just pulled it on when Darci knocked and then opened the door quickly again. I had barely cleared getting my butt into the suit. This was becoming dangerous.

"Hey, don't you want to wait for a reply first to your knock," I scolded.

"Lock your door if you want privacy, Little Brother," Darci said with a grin. "Why did I nearly catch you indecent?"

"Yes, very close. I'm going swimming."

"With the girls?"

"Yes."

"Lucky guy. I bet lots of guys would love to be caught between those two in a pool."

"I suppose."

"Would you rank it ahead of being caught between Katie and me?" Darci queried with pensive interest.

Now this was one of those questions I realized immediately that guys always fall for. Like does this dress look good on me? There were few right answers or actually maybe just one.

"Two equally lavish guy dreams for sure," I stated proudly.

"That's nice. Quick, Brother. Maybe I should invite Katie over for a swim and we can see which you like better," Darci said jokingly.

"Ah..."

"Don't worry, Nut-head. I'm not going to do that. Have fun," Darci said before leaving.

I grabbed the biggest clean towel I could find and went out early to lay in the waning sun. Even at just after 7:00 pm it was still quite light and felt good. I closed my eyes, but couldn't sleep. The anticipation of seeing Anna and Penny soon, plus the wicked option Darci had proposed, kept my thoughts excited almost to the point of physical reaction.

Probably closer to eight, Anna and Penny showed up. Each had a small bag with them, which I assumed held their towels. They looked like goddesses in tiny bikinis as they noisily came around the corner of the house. Penny was talking to Anna, but I couldn't make out the words, and she stopped as they neared. Both wore big smiles and pigtails to match.

My eyes drank in the two beauties as I rose to greet them. Anna first, then Penny, and then back to Anna, my eyes swept like rotating orbs someone just spun around. Anna's hot red bikini, what there was of it, accented her dark hair and body like a vision in red from the song. Penny wore an aqua blue tiny bikini that set of her pale skin and red hair perfectly. They both looked like they were walking off the set of a Sports Illustrated swimsuit model photo-shoot.