Sucker Bets

Unpacking and putting everything in its place was cathartic, especially filling my underwear drawer with my new panties and bras. Somehow that made it all seem normal, almost. The last thing I put away was the golf outfit. Another skort, this one red. The top I'd selected was a white cropped tank that would show off my tummy.

I couldn't help but wonder what Eddie was going to think. We'd known each other for years, been college roommates, shared our conquests and abject failures over too many beers to count. I knew I'd see him at the golf course. I just didn't know how he was going to react to seeing me dressed again, and by choice.

The other question was whether Ted was going to be there and what he would think. I hadn't talked to him since Sunday night. It suddenly hit me that over a quarter of my closet was now feminine. My boxers were in a bag after I replaced them with bright colors and satin and lace. My sock drawer now held a collection of stockings and pantyhose, along with a few garter belts that matched some of my new bra and panty sets.

What was happening should have made me nervous, but it was just the opposite. It should also have taken a lot longer than it had. Maybe it was like an addiction, but I didn't see myself as having an addictive personality.

When I first started playing golf, I took lessons and found time for at least nine holes every day. I did it until I felt comfortable that I wouldn't get laughed off the course.

When I took my first programming class, I spent hours and hours fine-tuning my programs. I learned more advanced concepts, doing everything I could to make sure each of them was perfect.

Maybe I just liked to be good at the things I did, and this was no different. Maybe that was why I had sucked Ted's cock three times last Sunday, too. I wanted to be sure I did it right. Or maybe I just liked all of it a lot more than I ever thought I could.

I got to the golf course early to see if I could figure out how to swing a club with tits. The pro must have liked the way I looked when I bent from the waist to tee up my balls because he gave me a free lesson.

Maggie smiled when she saw me. Eddie did a double take and gave me a funny look. We were already on the first tee when Ted showed up. I got a hug instead of a kiss and he rode with Eddie since Maggie and I were hitting from the ladies' tees. There were no side bets, just the standard twenty dollars plus a dollar a hole. What else did I have to lose besides cash? My masculine pride was gone.

With the pros' help on my swing, no pressure from any insane bet, and getting to hit from the ladies' tees, I was on fire. The only thing that seemed out of place was that the friendly banter we had all enjoyed with Ted the night we met seemed gone. Ted was standoffish and almost rude to Eddie a few times, and Eddie was behaving the same way.

It got so bad, Maggie and Ted switched carts, Ted riding with me and Maggie with Eddie.

"He called me and told me not to come." Ted finally opened up to me. "But I promised you I'd be here. I don't get it. We all got along so well and it's like he thinks he's protecting you from me or something, like he's almost afraid of something."

"I'll try to talk to him. And I am glad you're here." I leaned over and kissed his cheek. This was just so easy. It still made no sense, but it was easy.

Other than Eddie, the rest of the round was uneventful. It felt like he was the newcomer, not Ted. He just seemed irritated with everybody and everything. When we got to the clubhouse, he tossed Maggie a hundred-dollar bill and just left.

That was the last straw. He was going to tell me what was bothering him if I had to drag it out of him.

I didn't even knock. I used my key and let myself in, finding Eddie on his back porch drinking whisky. "What is going on with you today?" I grabbed his glass and took a sip. "Ted said you called him and told him not to come."

"I'm jealous, ok. I don't want to lose my best friend to someone else and the way you two were at Halftime really bothered me. You still have the nails and the hair, and then you show up today, well, like this." He pointed at me. "I know the bet is over. What the hell is going on?"

"You and Maggie seem to be a thing now, and that doesn't bother me."

"That's different. We've both had girlfriends before. I know how to deal with that. But this, you dressing like a girl, you liking guys; it's like you're becoming a different person."

"I don't know what to tell you, Eddie. I like this. It feels right. And I like Ted in a way I don't completely understand, but I don't want to lose you either. You know me. When I get into something new, I go all in until I figure it out. So, maybe I have a boyfriend. Ted hasn't even called me. If he did, would that be so much different from a girlfriend? And would I really have to choose between you and him? I'm still mostly the same person I've always been, well, sort of."

That got a smile from Eddie.

"All I know for sure is when I got out of the shower to get dressed this morning; when I put my makeup on, glued my forms to my chest, I wasn't putting a costume on. It was like I was taking it off. Eddie, you're always going to be my best friend. More than anybody else, I need you to understand. At least for now, I think this is who I want to be."

"What about your work, and shit, your dad?"

"I kind of already outed myself at work. The girl that sits next to me noticed my nails, and I figured what the hell, so I showed her pictures of last Saturday, golf and Club Zed. She kind of spread the word. The company and most of the people there are fine with it. I'll find out Monday what they think of the full deal, I guess. As for my dad and the rest of my family, I don't have a clue, but I have until Thanksgiving to figure it out."

Over the next few weeks, Eddie did his best to understand while he and Maggie got more and more serious. The guy at work that sent the flowers apologized profusely. He was trying to be nice and thought the pansy comment was funny, not offensive. He knows better now. Golf got rained out three weeks in a row. With Eddie spending time with Maggie and no word from Ted, all I did was play with my clothes and makeup and slip further and further into an entirely new world.

Ted finally called, and we went on actual dates, making out like teenagers and swapping blow jobs in the back seat of his car. I slept over a few times, and he did the same at my apartment, but it never went further than the oral sex.

It had been two months since that first bet with Maggie. I was living my life almost exclusively as a girl and loving all of it.

Then Dante called.

I was dating Ted. I don't know why I did it other than it was just supposed to be dancing, but I said yes when he asked me out. Something about him had gotten under my skin. He was imposing and maybe a little dangerous. I thought about the 'Daddy' thing and how it made me feel. There was that confidence and his powerful aura. He was just hard to say no to. We had seen each other a few times at Sunday brunch, and he had been nothing but polite. Ted would be out of town for the weekend anyway, so no harm, no foul. It was just dancing, after all. Just dancing.

I should have known when Dante showed up with flowers that this was more than just a casual dancing date for him, but I had spent hours getting ready. I wanted that feeling of power I had experienced when Maggie and I had first entered Zed. Dinner was over the top, too, and Dante had had his car, a BMW 7 series with all the extras immaculately detailed. He wanted more than just dancing. He wanted me. I could feel it. I should have called an Uber from the restaurant, but I didn't.

Zed was electric and as soon as we walked in the door, I felt it. Every eye in the place on me and Dante. I could feel their jealous eyes burning into me. Just like before, the guys all wanted me, except for the few that wanted to be me. And the girls? I smirked at the way the daggers shot from their eyes.

Dante commandeered a booth for us and ordered drinks. We sat for a few minutes before we hit the dance floor. I was on fire. The music, the pheromones filling the air; it was electric. Dante's body so close to mine, his hands rubbing up and down my sides, occasionally caressing a thigh or one of my fake breasts was so primal. When he kissed me, I melted into his arms. The voice in my head screaming at me to stop. I couldn't. I was too lost in the moment, too lost in his lips.

The fire in Dante's eyes was intoxicating. He took me by the hand, down the hallway, past the restrooms to a storage room. Leading me inside, he locked the door behind us and pulled me into his arms again. We kissed and my hands lost themselves under his shirt. His massive chest was silky smooth and covered with sweat while his tongue invaded my mouth, and his massive hands grabbed my ass and squeezed.

Up my body to my shoulders, a slight pressure was all it took. I dropped to my knees and clawed his cock from his pants. Already dripping clear liquid, I licked and kissed his glans, letting my tongue explore and tease the soft purple head before I took it in my mouth.

"I knew you'd be mine. Nobody tells me no, especially sissy bitches like you. Now suck your daddy's cock, whore." Dante's laugh was more of a roar. Everything in me told me it was wrong, but I did it anyway. Driving him as far into my mouth as I could, worshiping his heavy balls, licking, and kissing his slobber covered shaft.

My mind went to that first time in Ted's car, that uncomfortable, so awkward first time. I thought about how special it had been and how Ted had treated me after. Then I thought about that Sunday when he finally got me to my car and how I thanked him. This was so wrong, and I knew it. Dante was strong and huge and powerful, his very aura so dominant. It was like he just willed me to submit, and I didn't have a choice. But he wasn't Ted.

Maybe he felt the subtle change in the energy in the small room, or maybe he just wanted to exert his true dominance. Just as I pulled him from my mouth, Dante grabbed the sides of my head and drove his cock down my throat, face-fucking me with every inch of his manhood. I gagged and coughed, gasping for air every chance I got. He was relentless.

"You're my little sissy bitch now. You know that; don't you?" He laughed again as he shoved his cock all the way into my throat and exploded into my stomach. Dante pulled his softening cock from my mouth and wiped the slobber and cum all over my face. I fell back on my knees and cried.

Dante just laughed harder. "When I get through fucking that ass of yours, you won't even be able to spell, Ted."

Ted. He was jealous of Ted. Ted got me and he didn't. Dante was just a fucking bully. It was my turn to laugh. It was a hysterical, almost maniacal laugh.

"Why did I ever agree to go out with a loser like you?" I stood up and faced him. "A pathetic little man like you, when I already had someone like Ted, a real man that knows how to treat a woman? And I let you cum in my mouth like a cheap whore. What the fuck was I thinking?"

I moved toward the door. Dante grabbed my arm, spinning me around to face him again. "Nobody tells Dante no, nobody." Fuck, he was referring to himself in the third person now. I could see the passion in his eyes slowly turn to rage. The charming gentleman I had talked with at Sunday brunch was gone. He was showing me his true self.

"I'm taking that ass. You know it, I know it, and when I'm done, everybody else will know it, too." He lunged, and I dropped, rolling into his legs. Divine inspiration maybe, or just dumb luck, because his pants were around his ankles. Dante tripped over me and fell flat on his face. While he was trying to get up, I unlocked the door and scurried back to the table. I grabbed my purse, and made my way out of the club, asking the bouncer if he could get me an Uber, and fast.

"Where do you think you're going?" Dante barged out of the door and grabbed my arm again.

"Problem here, Dante?" The bouncer put his hand on Dante's arm.

"No, I got it under control. My new sissy just needs a reminder of who's in charge." He grinned.

"I'm not your fucking sissy, you jerk." I yanked my arm free and slapped him as hard as I could.

Another bouncer appeared, followed by a third. They were all standing next to me, facing Dante.

"I think you'd best call it a night, Dante." The first bouncer finally spoke.

Dante glared at me and then at the bouncers, pacing back and forth like a caged cat. "Fine!" he spat. "I'll deal with the bitch later."

I climbed in the back of the Uber and the driver handed me a box of wipes that I used to clean the mess off my face. I made sure to tip him extra.

A tall, absolutely gorgeous man with long brown hair and big brown eyes answered the door. It was obvious I had woken him up. "Is Ricki home? I'm Miki." On the verge of tears, I didn't know where else to go. I couldn't go home; Dante was probably waiting for me there. Ted was out of town and would probably never want to see me again once he found out what I had done, and Eddie and Maggie just didn't seem like the right choice. Eddie would want to hunt Dante down, and that would get ugly. Maggie would probably have encouraged him. My parents didn't even know what was going on, so I went to Ricki's. I needed someone that would understand.

"I've heard a lot about you. Come on in and I'll go get her." Victor gave me a kind smile, leading me into their kitchen. "Tea? It always seems to help me."

"Thanks." I just watched as he put the water on to boil, turning and leaving me there while he went to get Ricki.

Ricki and I talked. Victor just listened, leaving us alone long enough to make a phone call. When the police arrived, I told the story again, admitting that it had all started with my consent. Well, at least I hadn't said no. I could ask for a restraining order, but I didn't think a piece of paper would stop Dante. At Victor's urging, I got one anyway. Maybe he'd cool down and it would all just blow over. At least there was a police report of the incident.

I spent the night in Victor and Ricki's guest room. I didn't sleep at all. Everything that had happened ran through my mind, all the way back to that first stupid bet with Maggie.

Victor took me home and stayed for a while to make sure Dante wasn't around, or more likely to make sure I was comfortable being by myself in my apartment. I took a long bath and just let my mind wander. When I got out of the tub, I packed Miki away in her suitcase and in some boxes I had in the garage. Replacing my earrings with the simple gold studs I had gotten when I had them pierced, I went to get my nails done.

The bright red nails went away, replaced by a simple, clear coat. The extensions in my hair stayed, and I had my hair dyed a little more strawberry than before. I guess I wasn't completely giving up on her, but I needed a break.

"I heard. Are you ok?" were the first words Ted said to me when I picked him up at the airport. Not 'hi', not 'hello', not 'you dirty slut,' he didn't even comment on my lack of makeup and boobs. He just asked if I was ok.

"It was supposed to be just dancing." I shook my head no and fell into his arms.

We ended up at Halftime talking and eating. I told him everything. He just listened. When I dropped him off at his house, he pulled me into a passionate kiss.

"I can't believe you don't hate me for what I did." I nestled against his chest.

"You made a mistake and I know Dante. I've seen him do that to others. It's why I wanted to rescue you that first night we met. I should have warned you, I guess." Damn, he was blaming himself. He hugged me a little tighter.

"Did he really refer to himself in the third person like that?" He chuckled. I had to join him. As scared as I had been and as bad as I felt, that was funny. We kissed again, and I assured him I was ok.

"I just need some time to find my bearings. I'm just glad you're not mad at me."

"And I'm just glad you're ok." One last kiss and he disappeared into his house.

Me dressing as a woman got all kinds of attention at work, going the other way, not so much.

It was Wednesday when I found Eddie outside my apartment waiting for me when I got home from work. "Best friends, huh? You almost get raped, and I find out from Maggie? You go to a waitress we barely know instead of me?"

"I didn't want you to do anything stupid, like try to kick his ass. Besides, Ricki understands what I'm going through."

We stood there and glared at each other for what felt like hours. "I've got beer in the fridge."

"I could take him, you know." We were well into the second six-pack. "I just worry about you with all you're going through."

"I love you, too Eddie. You're a better friend than I deserve."

"You love me? Does that mean you want a threesome with me and Maggie?"

"No." I laughed. "I think it means you're sleeping on my couch again."

I had to admit the idea of a threesome with Eddie and Maggie was appealing. This whole thing had started with a bet I could get into her pants, after all. If I had to suck my best friend's cock to do it, well, I had now officially done worse. Knowing Maggie, it would cost more than that, and I wasn't ready for anybody to fuck me yet. I smiled as Ted came to my mind. We drank the rest of my beer and talked. True to form, Eddie passed out on my couch. He was gone when I got up to go to work.

Thursday was tough. I took mild relief in knowing Eddie's hangover was probably worse than mine.

Friday, when I got home, there was a black BMW 7 series parked in front of my building. I kept going. It pulled out and followed me. I called Eddie, Ted, and Victor. Victor had the best security, so I went to his apartment. Ted and Eddie were waiting for me outside. The BMW didn't stop.

"Leave your car here. I'll take you home to pack. You are staying with me until this Dante thing is over." Ted wasn't taking no for an answer. Eddie followed us and helped me pack, making sure I remembered my golf clubs. I packed the suitcase Ted had given me, too.

I had spent the night several times, always as Miki. Now I was moving in as Mike. Ted felt my apprehension and set me up in his guest room. That lasted less than thirty minutes after we went to bed. I couldn't sleep and went to his room. Without a word, he pulled the covers back and invited me to join him.

Saturday, Ted found me in the guest room, just staring at my suitcases.

"Are you going to let him win?" He came up behind me and put his arms around me. "Let him chase you back in the closet just because he's a jerk?"

"I don't want to, but the whole thing scares me. There are other people out there like him, and what about my family? What if he hurt you or Eddie or Maggie? I don't want to be afraid all the time."

Ted moved behind me, wrapping his arms around me. With a massive sigh, I pulled them tighter.

"Everybody's afraid of stuff." He nuzzled my ear and half whispered. "The trick is figuring out how to do it, anyway. You conquer fear by facing it, not running away from it. That's what my fortune cookie said the other day, anyway." I couldn't help but laugh.

We caught up with Eddie and Maggie on the third tee. My outfit was a light gray golf skort with red accents and a red diagonal striped top. Ted and I took bogies on the first two holes as a penalty for being late, and I still tied Maggie two strokes behind Eddie. Our little golf outings were getting expensive for Ted.

We spent the afternoon at Halftime watching football. Victor showed up and the six of us talked about what to do about Dante.

"Speak of the devil." Maggie whispered. I looked up to see Dante and three of his buddies come in the front door.