Sucker Bets

Some bets you just don't make. Just like some things you just don't say out loud. That's what put me in my current predicament. My best friend Eddie and I are avid golfers. We play every Saturday on different courses all around town. Competitive doesn't even come close to describing our games. We bet on everything, dollar a hole is just for starters. Who's going to be closest to the pin on the par threes, who will have the longest drive on the par fives? Who'll make a put or get out of the sand? It never ends. We even make bets on other players we don't even know.

I don't know if it was the amount of the bet I made with Eddie or that she heard me make it. She responded with a bet of her own. I knew hers was a sucker bet the minute she proposed it, but the stakes if I won were worth the risk. Maggie had joined us one Saturday. She was a single, stunning, tall athletic blonde with legs for days, crystal blue eyes, and an ass that probably stopped traffic every day. The pro asked if she could join us, and we agreed. Who wouldn't?

"Texas rules?" She grinned at Eddie and me as we teed up on the first hole, taking the first jab. Texas rules state if a man's drive doesn't clear the ladies' tee, he finishes the hole with his dick out to prove he's a man. Eddie and I laughed and agreed.

It went on like that every hole, some sexual innuendo or joke. She was killing us, making us laugh and openly flirting. We were giving it back to her in spades.

On the tenth tee, I made my fatal mistake. "You think I've got a chance, man? I'll bet you a buck I can get into her pants." I swear I thought I whispered.

"You think so, cowboy?" Maggie heard me. "I'll tell you what. You're up by two right now. You beat me and I'm all yours. But..." she smiled at me, "if you don't, you still get into my pants. The difference is that you wear everything I'm wearing right now, and I mean everything, next Saturday, for the entire round. I'll even get you some fake boobs."

Eddie roared, and well, I couldn't resist. Maggie was smiling at me and licking her lips seductively.

"You're on." I teed up my ball and hit it out of bounds. Shit. we were even off the tee. To my credit, I recovered my composure, and it turned into a great round. Maggie and I were super motivated, and Eddie didn't want to be left behind, so we all upped our game. No one could pull more than a single stroke ahead of the others, and that was usually only for a hole or two. We went into the short par five eighteenth, all tied.

Three perfect drives right down the middle. I took a chance with a fairway wood and rolled my ball up onto the green. I was putting for eagle. It was a long putt, but it put all the pressure on Maggie. She laid up and then hit a perfect wedge right to the middle of the green. Eddie was also on in three.

I must have been channeling Jack Nicklaus because I rolled my putt to about eight inches from the hole. I could make an eight-inch putt in my sleep. Worst case, Maggie made hers and we tied. No harm, no foul. Eddie put his close and putted out, leaving all the pressure on Maggie. She rolled her put around the cup and then tapped in for a par. Her ass was mine.

I took my time lining up my put, double and triple checking my line. Relaxed and confident, I looked at Maggie and smiled. She licked her upper lip with the tip of her tongue as seductively as she could and blew me a kiss. I did the same thing she had done. My spirit collapsed as my ball rolled around the lip of the cup, stopping just two inches away. Dammit.

She grinned at me and winked. I reached over to tap my ball in. We had tied. I might not be getting into her pants, but at least I was off the hook for next week.

We went to the clubhouse to settle our bets and have a beer. Maggie joined us at the table in a T-shirt dress tight enough to almost prove she was naked underneath. Smiling, she handed me a bag containing the clothes she had worn for the round of golf.

"Just throw them in with your regular laundry. They'll be fine." She giggled. "I'll have your boobies with me next week."

"Excuse me? We tied." I looked at her incredulously.

"Exactly, you didn't beat me. That was the bet. Not that I had to beat you, but that you had to beat me."

"She got you, man." Eddie was laughing so hard people were looking at us.

With our scores being the same, I ended up making a few bucks off Eddie on some side bets and that was about it; enough to buy a beer. I just had to dress as a girl next Saturday. I guess the upside was that Maggie wanted to keep playing with us. She was a lot of fun and a very good golfer.

I'd like to say I waited until the last possible minute to put on Maggie's clothes, but I found myself mesmerized as soon as they came out of the dryer. It was her panties that did it. Everything else was plain - pink, but plain. Pink compression shorts skort with a matching pink polo with a subtle floral design and a slightly softer pink sports bra. Even the little balls of fluff on the back of her ankle socks were pink. There was nothing overtly sexy about any of that; it had been her body that made it all look so hot. We were about the same size, so I was pretty sure I could wiggle into them. But her panties. Satin and lace, tiny, almost a thong but not quite, maybe what they called a cheeky.

I was just checking to make sure they fit, honest. Yeah right.

It was the way they kissed my butt cheeks, the way the lace trim tickled my ass when I moved to admire them in the mirror. From the back, they were so fricking sexy, from the front, that bush of hair just ruined everything. It stuck out the top and out the legs. It was gross. Of course, if I got rid of that, my shaved crotch would look silly, especially with my hairy legs and stomach, and that would..., well, an hour later, I had shaved myself clean from my nose down.

When I slid the panties back into place, I almost came just from the sensation of them moving up my smooth legs and nestling against my bare cock and balls. Fifteen minutes after I resolved that minor issue, I had completely dressed myself in her clothes. My research showed that pushing my now flaccid penis between my legs took care of the tent in the skirt. It also showed that two pairs of strategically wadded up boxers were the most comfortable option to give me boobs.

Don't ask me why I thought that was important because I couldn't tell you. Maybe I was trying to see how I'd look with boobs next Saturday. Perhaps it just made the look feel complete. Like I said, I couldn't tell you. I just did it.

Primping and preening in front of the mirror in my room for hours, I even took my hair out of my little man bun and played with shaping it around my face, making little pouty faces and stuff like that.

Rather than change, I ordered a pizza and just stayed home. I wore the damned outfit all day Sunday, too. Every time I walked past a mirror, I'd look and could almost see it. It was there in flashes and so hard to catch instances, the feminine figure in the mirror.

It was like a drug or something, and I was hooked. I couldn't get enough of that feeling, that excitement that only comes from something new, something exciting, on the edge. I'd felt it when I got my first sports car and again when I took Carol Murphy to the prom, convinced I was going to get laid.

Every day when I got home from work, I put the golf outfit back on and frolicked around my apartment. Like I said, I just couldn't get enough.

Eddie couldn't help himself. When I showed up on the course Saturday, he doubled over laughing. I completely understood why, too. That didn't mean I wasn't a little offended, though. I mean, sure, I was a guy in drag, and while homely, I thought I looked enough like a girl. Especially with the matching pink visor I had picked up to replace my standard golf hat.

Thankfully, the boobs Maggie brought weren't over the top comical. They were modest but obvious, and I thought fit my body. With the tacky backing helping to keep them in place and as tight as the bra was, they weren't going anywhere.

"So, Miki, you still want to get in my pants?" Maggie laughed.

"Always." I fired back.

"Double or nothing, and you can hit from the ladies with me." There was that sardonic smile again.

From the ladies? Hell yeah. I'd kill her from the ladies. "You are so on. What's the bet?" I laughed. God, I was stupid.

"You win, you get me. I win, you go out dancing with me tonight, as a girl. I'll take care of making sure you don't look like a clown, and besides, it looks like you already shaved."

Do you have any idea what boobs do to a golf swing? Well, I didn't either until then. I had possibly the worst round of golf in my life. I didn't win a single hole. Not only did it cost me a fortune, I had tonight to look forward to.

"So, what's the plan? Am I going to pick you up? Are you going to pick me up? What?" I almost sounded as unexcited about the prospect as I was.

"Oh, no." Maggie shook her head. "You have the basics, but to get you over the line is going to take some effort and some help. Leave your car here and just come with me. Girl, we have things to do."

"Like what?" I felt like something was sucking my soul out of my body as resignation to my fate washed over me.

"That is up to you. All you have to do is let me dress you up and go dancing with me. But, if you don't want to be laughed at, well, we need to make sure you pass as a girl and that is where the effort and the help come in. Your call, but you are going dancing, and you are wearing the dress I have picked out for you. How much can that ego of yours take?"

Not only had I lost the bet, she made it a challenge, a dare. Damn my ego and competitive nature. I looked at Eddie - as if he could save me.

"You made the bet, man." He was laughing again.

"All right dammit, let's go."

"Club Zed around nine-ish." Maggie turned to Eddie and smiled.

I glared at Eddie and just before he could say whatever it was he was thinking, got out a very stilted, "shut up, just shut the fuck up."

What the hell were we going to do that was going to take eight hours?

The first hour was a full body wax. They did my face, too. I only thought I'd shaved close. The next hour was a full body massage, and that was amazing. Then four hours in a chair while a stylist did something to my hair and some other people messed with my feet and hands. I had earplugs in my ears and had zoned out, listening to some soft jazz, so I didn't have a clue what they were doing.

When they were done, my dirty blonde hair was a soft strawberry blonde and cascaded down past my shoulders. My fingers and toes were bright pink, and I had gold studs in each of my ears. Mesmerized, I let them lead me to a seat in front of a mirror surrounded by lights. Over the next hour, I worked with a girl on how to do makeup. I didn't recognize myself when we were done.

The dress Maggie had picked out was called a bodycon. Skintight, it accented the breast forms they had now glued to my chest and hugged my lithe body down to about halfway up my thighs. Stockings and garters matched the panties and bra Maggie gave me and I got to practice walking in heels on the way to the club. Even with my modest hips, I was fucking stunning.

I used to think that men were the predators. When two gorgeous amazons, Maggie and I were just over six feet tall in our heels, walk into a club, everybody's world stops. They watch them float into the room, claiming their kingdom, taking control of everything they survey. Maggie and I could have had any man in the room we wanted, and quite a few of the women. We danced with most of them, including Eddie.

Some massive black guy tried to dominate my time, running his hands all over my body and pulling me close. "Baby, let daddy give you what you need. You know you want it." He ground his engorged cock into my crotch. I put my hand on his chest, smiled, winked, and gently pushed him away, only to grab some other random guy and kiss him full on the lips. I think I heard the words 'fucking bitch' as I left him standing there. My new partner lasted a few dances before I went to find Maggie, leaving carnage and frustration in my wake. I'd never felt so powerful, so alive.

As a guy, I'd have been lucky to get a dance or two. I had been here over three hours, hadn't left the dance floor once, and hadn't said two words to anybody; I'd just danced.

"Holy fuck, this is amazing." My face was beaming as I slid into a chair at the table Eddie and Maggie had found. "I feel like I own this place." I looked back at the dance floor. No less than a dozen guys had followed me to the table with their eyes.

The guy I'd kissed physically followed me. "I just want to thank you for the dance and the kiss." He blushed. "Can I buy you a drink or something?"

"Sure. Um, scotch neat and a bottle of water." I winked.

"Wow, scotch, most girls in here get cosmos and stuff like that."

"I like to think I'm not most girls." I looked over at Maggie and Eddie and grinned. "My friends call me Miki. You can join us if you'd like." I offered my hand.

Ted came back with a double and the bottle of water I'd asked for, and it was good scotch, too.

"Miki, that's different, too. Short for Michelle?"

"Nope, Michael. I told you I wasn't like most girls." I'd given up caring hours ago and what the hell, I'd probably never see this guy again, anyway. "Dressing like this is for when I go dancing, or sometimes when I play golf, but the boobs kind of mess up my swing."

I just had this 'I don't give a fuck' confidence. Nothing could hurt me tonight.

Maggie and Eddie laughed; Ted looked at me, confused. I explained what had gotten me here, and he relaxed.

"I love to play golf." Ted grinned. Maggie and Eddie smiled at me. None of us knew it yet, but our foursome was complete.

We talked and drank and danced and danced some more until the bar finally closed. Both elated and exhausted, I hadn't given a thought to what tomorrow was going to look like.

We were standing next to Eddie's car. We only lived a few blocks apart, and I figured I'd just ride with him rather than make Maggie go out of her way. "Shit, my car is still at The Gables."

"I live right by there; I can take you to your car?" Ted piped in.

Eddie and Maggie gave each other a funny look. I was too elated or too tired to care. "Sure, let's go."

Riding with Ted wasn't quite awkward, but it wasn't comfortable either. It almost felt like I had just had a fight with my girlfriend or something. Something needed to be said, and neither one of us knew quite what it was.

"Thanks." I smiled at him as I opened the door to get out of the car.

"Miki, wait." He put his hand on my arm. "Can I kiss you again?"

Boom. The other shoe dropped, and it was enormous.

Like everything else that had happened since I made that stupid bet with Maggie, I just went with it, leaning across the car and letting Ted's lips find mine. It was soft, gentle, sweet, like that first kiss in middle school after the graduation dance, full of innocence and promise.

"Ted, I don't know about this. In the club, I, well, I kind of was using you to get away from another guy."

"I know. I was actually on my way to rescue you." He smiled down at me.

"But, I'm..."

"Shhh." He kissed me again, this time more passionately. I surrendered. We made out in his car like teenagers. His hands slid over my body, fondling my fake breasts, and caressing my thighs as our tongues fought in his mouth and then mine.

It was all so strange, yet familiar, so intense. It was an extension of the energy I'd felt on the dancefloor when the guys I danced with ran their hands over my body and ground their cocks into my stomach. I didn't know what it was, but I wanted it. I craved it.

My dress slowly rode up, exposing my legs as he explored. I wasn't even aware of what I was doing, but my legs slowly opened, giving Ted access to more and more. When he slipped his hand into my panties and pulled my cock free, I just leaned back and moaned. My dress around my waist, I submitted to his advances, letting him take me in his mouth and suck me dry.

I didn't know what to say. I just sat there looking at him as he sat back up, his hand still fondling my softening member. The bulge in his pants was obvious, and I sort of felt like I owed him something.

"Ted, I... I don't know what to do."

"You don't have to do anything." He smiled at me and gave my cock one last squeeze before he slipped it back into my panties.

"I kind of feel like I owe you."

"You don't owe me anything." He smiled at me.

"Part of me wants to..." It was almost a whisper.

"Then just take it slow. Do what comes naturally and it will be fine, I promise." He pushed his seat back and reclined it to give me room.

Fuck, he was supposed to tell me no again.

It wasn't sexy or graceful or anything like that. I ended up on my knees, my ass in the air as I leaned over the console in his car, just like he had. One hand fondling his cock and balls while the other pressed against the edge of his seat. I explored. Ted pulled my hair back while I figured out how to bob up and down on his cock without pulling a muscle or breaking something.

When his body shuddered and he spewed in my mouth, I just kept going, licking and sucking until I was sure he had finished. I think I swallowed, but I wasn't sure. I took a minute or two to lick him clean, smiling with an odd sense of satisfaction as I settled back into the passenger seat of his car.

What an insane day. I had played golf and gone dancing as a girl and had the time of my life. I had just given my first blow job and was proud of it. And there was a guy looking at me with those eyes, the ones you reserve for that someone special, and I liked that, too.

Ted walked me to my car, admiring the way I adjusted my dress to pretend to be more ladylike.

"Shit!" I literally screamed.

All I had in my small clutch was my lipstick and a compact to touch up my makeup. My damned keys were in my golf bag along with my wallet and phone, and that was in Maggie's trunk.

Ted was kind enough to drive me home, but Eddie had my spare key. We tried his house. He wasn't home. I could ask him to take me to Maggie's, but I didn't know where she lived.

"My place?" he offered. I just shrugged and nodded. I'd figure out tomorrow, tomorrow.

Ted's house was neat and clean and definitely a guy's place. A simple craftsman style with a detached garage on a nice lot with a huge TV, gaming console, a massive leather couch and a matching recliner. It spoke of a man that took care of himself. It was a lot neater than mine or Eddie's.

"I can set you up in my guest room. It's not the Ritz, but the bed is comfortable." Ted was being a gentleman. I figured I'd already sucked his cock, so what did I have to lose? I set my purse down, stepped out of my heels and turned my back, pulling my hair out of the way so he could unzip my dress. Letting it fall to the floor, I took his hand and led him toward the bedroom.

"Do you have a t-shirt I can borrow?" I smiled as I unhooked my bra. My forms weren't going anywhere, and my bra was bothering me almost as much as the heels had been. One more piece of the trail from his door to his bed. I sat on the side of the bed and slipped my stockings down my legs, dropping them and my garter belt next to my bra. My panties might be next, but he'd have to take those off, unless he was as tired as I was.

He gave me an old ZZ Top shirt from their Legs album. I smiled at the implied compliment, pulled it on and climbed into bed, waiting patiently for him to join me. Tired won out with little resistance, we cuddled and kissed a little before I let out a massive yawn. Rolling onto my side, I pulled his arm tight around me as he spooned behind me and held me close. He was a cuddler, and I liked that, too.