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Baseball Annie's Big Mistake Author: Quillpen Date: 11 August 2026 Job/Place-of-work, Consensual Sex
![]() Author’s Note: A “baseball Annie” is a woman who desires sexual intimacy with professional ballplayers. They have been lingering around the game practically since its foundation as a paying occupation, long before players became millionaires. These women are are basically status-seekers. The phrase gained widespread public attention in 1949 after 19-year-old Ruth Ann Steinhagen infamously shot Philadelphia Phillies first baseman Eddie Waitkus in a Chicago hotel room. Media reports at the time began using the expression "baseball Annie" to describe obsessed young female fans who stalked players. The quaint term has become a part of baseball lore; it was later documented in baseball memoirs like Jim Bouton’s raunchy, groundbreaking book, Ball Four, back in 1970 when it was first published. Part One My name is William (Will) Harvey. When I was 27 years old in 1983, I got a job as the travelling secretary and statistical analyst for a minor league baseball team. I won’t mention the club’s name, but it was a well-known team at the AAA level of the sport, which is just one notch below the major leagues. Except for those few major league players who are demoted because they have been disappointing on the field, or because they are rehabilitating from injuries, there are no millionaires in the minor leagues. In fact, ballplayers, even those in AAA, are not making a fortune. They are mostly chasing their baseball dreams. Very few realize them. I acquired my job with the team in December 1982. It was a fortuitous accident. I was attending a large Christmas party at the home of a friend. As was our habit, the host and I were discussing sports, principally baseball. That was our primary interest. Slowly, a few other males overheard what we were talking about and joined in on the conversation. One middle-aged man seemed to be especially interested in picking my brain. He was fascinated by the statistical minutiae I had memorized about so many major league players. I told him that baseball stats were badly underused in many ways. I was way ahead of my time. Long before the movie Moneyball was made, I opined that studying stats could be a very effective way to predict players’ potentials and, if employed properly, could be an extremely helpful and effective tool to a manager during a game. As an example, I mentioned to him that I thought stolen bases were highly overrated and basically not worth the risk unless you were considering a speedster who was successful in his attempts at least 95 percent of the time. “I favor the three-run home run, just like Earl Weaver does. The stats prove him right.” At that time, Weaver was the famously fiery manager of the Baltimore Orioles who preferred to play for big innings rather than manufacturing one run at a time. “Would you be interested in a front office job with my team?” he asked me out of the blue. I had no idea at all who he was. “Huh?” I said brilliantly. “Who are you?” Shaking my hand warmly, he introduced himself as Thomas Miller, the general manager of the Triple-A team that played in a neighboring city. I did know his name and I had seen his picture in the local newspaper on occasion. I just didn’t recognize him away from a baseball setting. He said his team was looking to replace its traveling secretary who had just retired. He said I could have that job as well as a consultant’s job where I could put my baseball knowledge to practical use. Considering I was pondering a career change, this was an ideal offer. I swiftly accepted. I didn’t even ask about the job’s salary or accompanying benefits. I began work the next day. Part Two To my delight, I absolutely loved my new job, especially during the offseason. I learned the traveling secretary’s duties rather quickly. I didn’t have all that much to do until the season approached in the springtime. However, Mr. Miller gave me free rein to broaden my statistical knowledge of the players he expected to be on the team’s roster for the opening game of 1983—and the most noteworthy of our opponents. I was getting paid to study baseball stats! What a great job this was! Of course, as a fan of the game, I did know about “baseball Annies” and their long history. I thought they were amusing peripheral figures associated with the sport. I could understand why typical ballplayers were drawn to them: easy and plentiful sex with very compliant young women. I could not have imagined that I would be a beneficiary, however. During the team’s first homestand toward the end of April, I was exiting the ballpark after our team’s third consecutive victory. I was in particularly high spirits as the club’s field manager, Jerry Smolinski, heeded my advice regarding when and when not to make substitutions on no fewer than four occasions—all of which paid off. It had been arranged that I would be just a phone call away from Smolinski during every game. He was skeptical at first, as most baseball people are when exposed to something new and different, but when my hunches proved to be strong ones, manager Smolinski began to exhibit considerable faith in me. “You’re making me look like a genius, Will—and I greatly appreciate it!” he told me immediately after our team’s solid 7-2 win that day. I was in especially good spirits when I headed to the staff parking lot which the players also used for all our home games. Because of that, I could understand the misconception that was about to occur between me and a “baseball Annie.” When I was about five feet from my vehicle, I was approached by a very attractive female, whom I figured to be about 22 years old. She stood perhaps 5’5” tall and was nicely busty. She also had a cute face, and shoulder-length, shimmering black hair. Those were nice attributes to have—especially the assets she possessed on her torso. With a smile she asked me, “Are you a member of the team? You must be if you’re allowed to park here.” “I am indeed!” I replied. “Did you have a great game today?” was her next question. “That seems to be the prevailing opinion,” I said. I also told her my name. She told me hers. It was Hailey Dudhope. Hailey wasn’t much on small talk. She preferred to get right down to business. “Will,” she began, “would you be interested in coming to my apartment right now? We could have a very intimate night together. Does that sound appealing to you?” As I had no present love interest and I was a normal, healthy male in my twenties, there was no way I could reject such an enticing offer with such a comely young woman. “Lead the way, Hailey!” I responded. She did. Hailey got into the passenger seat of my car. I drove her a short distance to the nearby public parking lot where she had left her car. From there, I proceeded to follow Hailey to her apartment building that was perhaps a 10-minute trek away. During my drive there, I had a smile plastered across my face. I could scarcely believe my luck. Hailey lived on the second floor. We rode the elevator up one flight. Within seconds of her unlocking her door, she led me to her couch which contained a pull-out bed which was already pulled out. I could tell Hailey wasn’t big on romance nor sexual foreplay as she quickly began to disrobe. I followed suit, of course. By the time I had removed my clothing and tossed everything onto a chair, Hailey was lying in the center of her bed with a naughty expression on her face. She was sexily fingering her shaved vagina. This was definitely the fastest-moving relationship I had ever been involved in! I gave my stiffening dick a few helpful yanks to get it standing tall and then I happily joined her. Unlike by bedmate, I was always the romantic type. Thus, I figured I should begin our carnal get-together with a few long kisses, despite the obvious physical charms that Hailey possessed. As we kissed, Hailey began to caress my testicles and shaft with her right hand. I got the impression she wanted to get down to business very quickly. I wasn’t about to object, so I went along with her tacit plans willingly. Hailey’s lovely breasts rated a perfect 10-out-of-10 score from me. That’s a difficult feat to achieve because I’d admired girls’ boobs since towheaded and vapid Martha Kramer started wearing a brassiere late in the fourth grade and liked to flaunt her prominent chest at the boys. Hailey’s goodies were round, firm, and culminated in excellent nipples. I envied any babies these jugs might eventually feed. They really were magnificent sexual objects—and I greedily placed them in my sweaty hands. I merrily groped them until her nipples were nearly as hard as my manhood. Hailey’s tits were so inviting that the next obvious step for me was to suck on them. I moved steadily from one to another, licking and sucking them for several minutes. I eventually straddled Hailey to give her a titty-fuck, something I always liked to do whenever I had a busty and compliant bedmate. (Hailey was certainly both!) I enjoyed that sex act and managed to withhold my cum shot somehow. When I didn’t ejaculate, Hailey seemed somewhat surprised so she put her lips around my shaft and gave it a good licking. This girl was certainly unabashed about her sexual desires—and I was enjoying all the benefits that went along with it. Knowing that time was not my ally, I removed my dick from Hailey’s warm mouth and put it where it truly belonged: deep inside her pussy. I could tell I wasn’t the first male to visit Hailey’s pleasure palace, but it was an enjoyable stay while I lasted. I gave her a series of vigorous thrusts. With an ejaculation imminent, I pulled my dick out of Hailey’s pussy with a few seconds to spare and sprayed a sticky, messy load of three semen ropes across her lower abdomen. I couldn’t help but utter a genuine groan of satisfaction as I came. “All you baseball players certainly do enjoy fucking,” Hailey told me, obviously speaking from much experience on the topic. I took that remark as a compliment. I wasn’t going to correct her misconception yet, so I played along with it. “In pro baseball, you don’t come across too many women in the workplace. Some of us get lonely for female company. Hailey, thanks for providing companionship for me today in the best possible way.” “There’s another game tomorrow. Isn’t that right, Will?” Hailey asked me. I nodded and succinctly replied, “Yep!” “Okay, ” Hailey stated. “Tomorrow, I’ll meet you by your car again about 45 minutes after the game ends and we can have another fuck, Will. Here’s something you don’t know about me: I don’t attend the games; I just listen to them on the radio as background noise. I really don’t fancy baseball as entertainment, but I certainly do fancy baseball players as bedmates.” “Hey, everyone has different likes and dislikes,” I replied philosophically. “Be that as it may, no sane male would refuse that kind offer for more great sex tomorrow, Hailey, ” I added. Then we kissed and cuddled for a while. I showered shortly thereafter and went on my way, still not believing my fantastic luck about Hailey’s fortuitous misunderstanding regarding my role with the team. Part Three Things went exactly according to plan in every way. The team won its fourth game in a row. I did well by suggesting a timely pitching change and a pinch hitter to manager Smolinski in two critical spots in the game. We won. It was a thrilling, 4-3 squeaker. Hailey showed up as scheduled afterward and we eagerly traveled to her apartment for a sexual sequel. I was euphoric over how well I was doing at my new job, how my insights were helping the team, and the unexpected fringe benefit I was getting from my personal “baseball Annie.” I told a few of the players about Hailey. They all thought the situation was hilarious and encouraged me to keep screwing her until she figured out I wasn’t a professional ballplayer. I concurred. Accordingly, I decided to give Hailey a world-class, aggressive fucking (after, of course, enjoying her stunning set of mammary glands to the fullest). I rammed her frontwards backwards, sideways and even while I was standing up and holding this comely sexpot in my arms. This time when I came, I made a point of covering Hailey’s breasts with my thick blast of jism. It was a sexy sight, but I helped her clean my deposit from her chest with some paper towels. Of course, that was just a convenient excuse for me to continue to fondle Hailey’s prime assets! As we engaged in a post-coital cuddle, Hailey innocently asked me how I had done today at the ballpark, “I wasn’t paying much attention to the radio description of the game, as usual,” she admitted. I answered, “Manager Smolinski praised me for being a great help. He gave me plenty of credit for making some important decisions.” That was a completely honest but usefully vague answer. I was proud of myself for coming up with it. Then the truth started to emerge when Hailey asked me how many hits I’d had in the game and if I’d fielded my position perfectly. She knew more about baseball than I imagined she had. Having had two great fucks with a sexy twenty-something, I decided to come clean and face the consequences of being completely forthright with Hailey, whatever they might be. I took a deep breath and ruefully said, “Hailey, I’m not a baseball player. The last time I had a baseball uniform on, I was 14 years old and playing in a boys’ league. Yes, I’m part of the team. I work in the club’s front office in a special position that was created for a unique talent I possess. My official job title is Statistical Analyst, Traveling Secretary and Special Consultant. I basically crunch the baseball stats of our players and their opponents. Then I make suggestions via telephone to Manager Smolinski during the game whenever he calls me. Sometimes I take the initiative to call him when I think my numbers can help him make good tactical decisions. So far everything has worked out quite nicely for me—and the team as a whole, of course.” Hailey listened intently to what I uttered—and then she became angry. “So, Will, you’re telling me you’re not a professional athlete at all? You’re basically a numbers geek instead?” she barked at me. “Yeah, that’s about the size of it,” I said. “Hailey, had you looked through your copy of the team yearbook that I know you have, you would have known that. My listing says what I do. I’m not going to apologize for it because it is a dream job for me. I’m very good at what I do and I’ve become an important cog in the machinery of a strong baseball team. Some guys are on the team to hit home runs. Some guys are on the roster to be pitchers. As for me, I play with statistics until they tell me something that helps the team. Is there a problem with that?” “Yes, there is, Will,” Hailey declared. “I only want to sleep with baseball players, not office personnel. I don’t think I want to do this anymore with you. I want to be bedded by up-and-coming professional athletes. I might get lucky and end up bedding a future Hall-of-Famer. Anyway, that’s my sexual fantasy and I want to live it. They appeal to me. Number geeks don’t fit anywhere into my plans.” I was tempted to call her shallow and remind her that she had mistaken me for a pro ballplayer both before and after we’d had sex, but I accepted Hailey’s unshakable verdict on the matter. I barely said a dozen more words to her before I left her apartment for the second and last time. The phrase “All good things must end” ran through my mind as I drove home. I never encountered Hailey Dudhope again. Within a week, three different players had replaced me as Hailey’s bedmate—at least that was the scuttlebutt I overheard. Interestingly, two of them began to slump and were demoted to Double-A baseball. The other one was traded. On the other hand, the club won the league title for the first time in 22 years. On Opening Day 1984, I received a gaudy championship ring for my contributions to the highly successful 1983 season. 94 32 15906 10 Leave your commentSign Up and leave comment
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