Jason found me still sitting on the bench after many of the other players had already headed home. "Hey, Bailey, don't be so hard on yourself - it's just a game!" He stood above me, resting one foot up on the bench next to where I was sitting.
"Yeah, I know. I just can't believe how different it is to hit those slow pitches - guess I'm still used to the rhythm of the fast-pitch game, even after a few years away from playing!"
"Well, I can tell that you're a very talented player - so it's just a matter of getting your timing down. You need to be a little more patient than you're used to, the ball just isn't coming at you as fast. I'd be happy to stick around for a while tonight if you'd like to work on your rhythm?"
I looked up at him, was once again pulled in by his genuine smile, and nodded, smiling back, taking him up on the offer.
We hung out at the field for at least another hour, Jason or I occasionally breaking down into laughter at my ridiculous swings, until I finally started to feel comfortable, hitting a few solid ground balls, ropes out to the outfield, and even, finally, a home run over the right-field fence.
"On that note, Bailey, why don't we call it a night."
"Thanks so much, Jason, I really appreciate your taking the time to do this!"
"Hey, my pleasure. After all, we can't have our cleanup hitter swinging through every pitch, can we?"
*-*-*-*-*-*-*
What started out as a fairly innocent office crush quickly became an all-consuming passion. Not only was I seeing Jason at work, but every Tuesday night for practice, every Friday night for games. And I was in uncharted territory. Throughout my high school and college years, I'd always had guys falling all over me, always had a date - or more - whenever I wanted. I was the successful athlete with the great body, who looked equally good - and knew it - sliding into second or dancing at the club. Now, I was the one drooling over the cute, successful guy. And although we were spending lots of time together, and he was perfectly charming, he either wasn't interested, or was playing hard-to-get. And it was driving me up the wall: I had never had to practice the techniques of trying to win someone's affections, and I sucked at it!
Jason was in his early 40s, had enjoyed great success in business, but not at the expense of his personal life - he was well-liked by employees and business partners alike, and enjoyed life to the fullest when he wasn't working. He was an avid runner, skier, active in many local community causes, and rarely said 'no' to a fun night out, whether a trip to the symphony with some of his wealthy older colleagues, or a visit to the pub for a few beers after a hard day of work.
My first attempt to send him signals that I was interested in more than just catching his balls, was to select a few of my more revealing outfits to wear to the office, and then find excuses to be passing by his office or meet him as he got off the elevator. Whether it was my favorite red silk blouse which showed off my perfect breasts, or a short black skirt which left little of my long, athletic legs to the imagination, I rearranged my closet so that anything I picked would show off my great figure. Rather than putting my hair up, as I often did for work, I let it down, showing off my long blonde locks. Similarly, although I often wore glasses to the office, knowing I'd spend several hours working at the computer, I began wearing my contacts instead, showing off my big blue eyes.
Let's just say, it backfired. Not that Jason didn't notice - he did. I felt warm and tingly each time I felt his eyes moving over my body, enjoying the view that I was so eager to show him. And not that Jason didn't appreciate - he did. But even as he asked me out - after enjoying several days worth of these outfits - I was once again feeling out of my element: rather than having him wrapped around my little finger, I was wrapped around his.
"You know, Bailey, you don't need to dress like that to get my attention. It's much more effective to leave something to the imagination. And if you're going for a sexy office look, you should really stick with the glasses. But hey, I appreciate the effort. What time should I pick you up Saturday night?"
"Um, really? I mean, um, how about 7?"
We had a delightful time that Saturday evening, went out for dinner and drinks and then to a dance club, where I discovered that among his many other talents, he was a great dancer. After enjoying ourselves on the dance floor, we talked for an hour or so over another round of drinks, and then he drove me home, walking me to the door of my apartment.
"Well, Bailey, I had a lovely time, you're great company."
"I had a wonderful time, Jason. Best night out in a long time. Would you like to..."
He interrupted me before I could finish what I'm sure was an obvious question, "I'd better be going, Bailey. See you at the office on Monday." He leaned in, put his finger on my chin to raise my lips to meet his, and kissed me, warmly and softly, and then was off without another word.
I let myself into my apartment and collapsed onto the sofa, confused. It was a perfect evening, and yet I was doubting myself. Let's just say, no man had ever left me at my doorway with just a kiss after a great night out before. I may have left a guy, gone back to my place on the excuse of homework or a game the next day, but anytime I invited someone in, he unfailingly accepted.
Strike one?
*-*-*-*-*-*-*
We began to see each other regularly outside of work - and softball - over the next few weeks, always having a wonderful time in each other's company, yet never progressing beyond the occasional kiss, embrace, or playful touch. After several of these encounters, my frustration growing, I decided it was time to try another tactic. I'd learned enough about him to venture an educated guess about what he might like in terms of playful dress-up, and I planned to surprise him on our next encounter.
He was going to pick me up at 7:30 on a Saturday. Earlier that day, I made a trip to the mall to pick up the things I'd need to complement what I already had on hand, and by 7:15, I was dressed and ready for him. I'd found my old high school cheerleading uniform, which still fit - although my breasts had grown fuller since high school, so the top looked as if I'd chosen it specifically to show off my tits. My high school colors were blue and white, the uniform's top was a blue sleeveless v-neck, and the skirt was white, pleated, with blue trim. My trip to the mall had added to my wardrobe a matching blue bra and thong panties, as well as blue hair ties which I used to pull my hair up into ponytails.
At 7:25 - Jason was always punctual, so I knew he'd arrive exactly at 7:30 if not one or two minutes earlier - I left my apartment, walked down the hall, right out the front door of the building, and stood on the sidewalk, waiting for him. If it wasn't such a quiet neighborhood, I probably wouldn't have risked it - but fortunately, as I'd guessed, Jason was the first person to see me when he arrived a few minutes later.
He got out of his car, spotted me, and paused for a moment, taking in the view with a smile. He walked over to me, took me by the arm, and walked me back towards the building, saying, "let's get you back inside, shall we?"
I eagerly followed, hoping that my bold move had the desired effect, and he was taking me inside to ravish me, but I soon realized I was mistaken.
"Do you have no patience, Bailey?" His eyes were still smiling, but his voice was all seriousness once we were back in my apartment.
"Um, but, don't you like it?" I twirled around, my skirt rising up as I did so, giving him another great view of my tight ass.
"Of course, Bailey, you're adorable. I just think you still have a lesson to learn about showing a little discipline. You don't always swing at the first pitch, right? Anything of quality in life is worth waiting for, that's all I'm saying."
"Well, um, yeah, but..."
"Well, then, let's go out, enjoy a nice evening. You should probably change first..."
Strike two?
*-*-*-*-*-*-*
I know I've shared this already, but it bears repeating. I was completely out of my element, utterly confused and frustrated. Yet at the same time, I was having the time of my life. I was dating a great guy, enjoying
my job and the camaraderie of the company softball team. I just couldn't understand why he hadn't made his move yet. I kept thinking about what he'd said that night, about anything of quality being worth waiting for. I did agree, really I did, I'd just never had to wait for sex before!
I should catch you up on the progress of the softball season. In the midst of all this personal drama, the team had done quite well, and we were in the game for the league title. My teammates made sure I knew that they'd never done this well before, and that they credited me with much of the success, which obviously filled me with some pride, but it was still Jason's approval I was ultimately seeking.
The title game was a neck-and-neck one, each team responding with an equal number of runs after the other team would score. Finally, in the top of the ninth, we'd pulled ahead by two, and it was just up to us to hold the lead through one last inning. Jason struck out a weak hitter to start the inning, one down. He then gave up a hit and a walk, then got the second out with a pop-up. Two outs, two on. With our teammates cheering, we began what we hoped would be a quick last at-bat before we could begin our celebration.
The only thing standing between us and victory was the other team's best hitter. Oh well, victory isn't as sweet when it comes easy, right? After weeks of catching Jason's pitches, I began to remember a little of the feeling of playing in a high-stakes game. My pulse picked up a little, and I became ultra-aware of my surroundings. Strike one. Ball one. Strike two. Jason then motioned for me to visit him on the mound.
I got up out of my crouch and jogged to meet him.
"You've got him, you can strike him out!"
"I didn't call you out here to talk about softball, silly," Jason said with a wink.
"Oh, what then?"
"It's been great throwing to you tonight, watching you totally in the zone. You're much sexier when you're not thinking about your appearance and trying to impress me with skimpy outfits, you know. You've been very patient, and I think you've finally earned the best sex of your life."
"Oh, really," I quipped, "and what makes you think you'd be the best I've ever had?"
"Did that sound as ridiculous to you as it did to me, Bailey?"
I couldn't help but giggle as he called my bluff.
"Now, let's get this guy out. And don't you dare think we can sneak off right after the game. We've got to celebrate with the team first. But don't worry, we'll go back to my place afterwards. Just a little more patience, Bailey."
I'd never felt hot and bothered while wearing all of my catcher's gear before, but in that moment, it was all I could do to concentrate long enough to get back behind the plate and catch the ball Jason threw for the third strike. Our team met up at the pitcher's mound, high fives all around to celebrate, and then we piled into various cars for the short drive to our hangout pub a few blocks from the field. Jason had given me a ride to the game that night, so I rode with him to the pub.
"Unzip my pants," he commanded as soon as we were on the road.
"What, now?"
"Yes."
I did as I was told.
"Now, put it in your mouth. I want you to suck my cock until we get there."
I immediately followed his directions, unbuckling my seat belt and leaning over, both hands working to free his cock from his uniform and boxers, before taking him into my mouth. His soft cock quickly grew hard, and within a few moments I was straining to keep his full length inside my mouth. Knowing that we must be almost to our destination, and trusting he would stop me when we arrived, I began bobbing up and down on him, eager to satisfy. Just moments later, he stopped me.
"Good girl, that's nice work. Now, let's go enjoy the company of our teammates." He quickly zipped up, his erection disappearing as he put on his company boss hat and marched into the pub to congratulate everyone on the victory. Knowing that I would be rewarded for patience, I poured a beer from the pitcher at the nearest table and began mingling, going so far as to ignore Jason while I talked to the other folks there.
About an hour later, I felt a hand on my shoulder and turned to see Jason behind me. He whispered to me, "It's time, but let's not make it obvious that we're leaving together. Why don't you go first, wait in my car, and I'll be there in a minute."
I nodded that I understood, and after saying a few quick goodbyes, made my way out to the parking lot and let myself into his car. My mind racing with the thoughts of his big hard cock buried deep inside of me, I watched the clock on his dash as about five minutes went by, before he finally came out to join me.
"OK, Bailey, here we go. Are you excited?"
"Oh, yeah."
"Did I mention how sexy it was to watch you behind the plate tonight, waiting to catch each of my pitches, and throw it back to me, getting into a rhythm? I couldn't help but imagine what it would be like to be with you tonight. You're not tired from crouching, are you? Because I was hoping we could put you in that position a little longer."
"Actually, I am, maybe I could just go down on my knees for you?"
"That works for me."
A few minutes later, we arrived at his house, helped each other out of our uniforms, and were soon in his bedroom, naked.
"God, you're gorgeous, Bailey."
His hands moved all over my body, squeezing my breasts, pinching my nipples, briefly cupping my pussy, before he asked whether I was ready to get on my knees and continue what I'd started in the car a few hours earlier.
"Absolutely, Jason," I smiled, going down to my knees and pulling his entire cock into my mouth with one smooth stroke. I cupped his balls in my left hand, rolling them between my fingers, tickling them, as my right hand grasped his shaft firmly and worked together with my mouth to establish a regular rhythm. As I worked, Jason gathered my long hair in his fingers, grasping it into a tight ponytail, and used it to control my motions on his hard cock. He then began encouraging me with his words.
"That's it, Bailey, stroke it, long smooth strokes. I've watched you every time you've come up to the plate, bat in hand. Do you realize how naughty it looks, your routine with your bat? You hold it up with your right hand, stroke it up and down with your left, before every swing. Every time I watch you I imagine what it would feel like to have those hands around my cock."
Even just a few minutes in, it was clear to me that Jason's stamina was impressive compared with guys I'd been with in the past. I'd actually prided myself on being able to get a guy off in just a few minutes, but it was obvious that Jason knew how to last, how to enjoy the build-up to his climax that much more. Just as my jaw began to tire, after sucking him off for several minutes more, he let me up for air.
"Let me help you up, Bailey, your knees must be tired. I think you've earned a turn at a little pleasure."
He encouraged me to lie down on the bed, and spread my legs wide apart, before kneeling on the floor next to me. He slowly explored my inner thighs with his tongue, with long, wet strokes, before finally reaching my pussy lips, spreading them apart with his big, strong fingers, and beginning to lick me, my juices already flowing. I moaned and arched my back in pleasure with his first touch to my clit, and then cried out in delight as he plunged one finger deep into my pussy.
His touch was expert, nothing like the guys I'd been with in the past who had blindly rubbed away on me, just hoping to make me wet enough to fuck. Jason actually knew how to bring a woman pleasure. My eyes were closed as I enjoyed the touch of his tongue and fingers, so it wasn't until I felt his movement that I realized he was shifting positions. He kept one finger active inside of me as he climbed up onto the bed, straddled me in a 69 position, and thrust his cock in my mouth as his tongue once again found my clit. As I continued to writhe in pleasure beneath him, I focused all the attention I could on him, pulling his balls into my mouth and sucking them, one by one, as my hands were busy stroking his shaft.
I once again pulled his cock into my mouth, sucking in as much length as I could and holding it there, as he sucked my clit into his mouth and massaged the e
ntrance to my pussy with two fingers. After just a few moments more of this extreme pleasure, I came, a powerful orgasm wracking my body as I moaned around his big cock, still buried in my mouth. He kept up his calm rhythm as I rode out this pleasure, before finally pulling his weight up and off of me, sitting down next to me on the bed and watching as I fondled my own breasts, enjoying every moment of the ecstasy he'd brought me.
When I finally came back to reality, I saw that Jason had been stroking himself as he watched me, and was once again rock-hard and ready for action. "That was incredible, Jason. Best orgasm I've ever had. You were right, patience has its rewards."
"You sound like you think we're done..."
"Oh, no, I can see you're ready for more."
I smiled and sat up, crawling over to him and straddling his legs as he let his head and shoulders fall back against the pillows. I rubbed his rock-hard cock against my pussy lips, moistening it with my juices, before finally positioning myself over him and lowering, slowly, until I had him fully inside. I remained there for several moments, just rotating my hips slightly, enjoying the fullness, and then finally began moving up and down just a few inches with each stroke.
He reached up and grabbed my breasts as I rode him, kneading and pinching my nipples. After several minutes in this position, he spun me around into a reverse cowgirl, grabbing my hips to encourage my motions as I continued to bounce up and down, the strokes deeper and faster now. I cried out with pleasure at the sensations of this new position, encouraging him with every stroke with louder and louder moans of pleasure.
After riding him for what seemed like hours, Jason pushed me up and off his cock, and we both climbed off the bed. He took me by the hand, led me to the foot of the bed, spun me around and embraced me from behind, whispering in my ear, "put your hands against the bed frame and spread your legs, I want to fuck you from behind until we both cum."
Filthy Daddy's Taboo Erotic Sex Stories Page 88
