Sucker Bets

I woke up alone, which was both a little disappointing and a little relieving. I had enjoyed cuddling with Ted and feeling his arms around me as I drifted off to sleep, but I was still clueless about what I was doing. Either way, I couldn't help but smile when he came out of his closet with a suitcase full of clothes.

"These belong to my ex. I think some of them may fit. It's been six months, so I don't think she's coming back for any of them. Keep what you want. We can drop the rest at the homeless shelter on the way to breakfast."

The panties were a hard pass. There was just something inherently wrong about the idea of me wearing Ted's ex-girlfriend's underwear. Especially since I didn't know how clean they were. Most everything else, though, fit me well enough. I found a few pairs of shorts I liked and some jeans, tops and skirts. The veritable gold mine was shoes, a dozen pairs of heels, pumps, flats, and sandals. Those all fit like someone made them for me.

I enjoyed watching Ted's reactions to what I tried on as much as I enjoyed playing dress up. Mostly he liked that I let him watch me change, and that I hadn't put my bra back on. My forms weren't real, but they were expensive and, with the way the salon had glued them on, looked as if they were. With them hanging from my chest, I was as much a girl as if I had been born one. Well, not quite, but Ted seemed to like that part, too.

My eventual choice was a simple pair of khaki shorts, a cropped tank top, a sports bra I stole from his ex, and a pair of wedge sandals. Ted helped me gather my clothes from last night and I carefully packed them in the suitcase with everything I was going to keep. The panties we put in a trash bag.

"Here. These were hers, too." Ted walked up behind me as I was trying to fix my makeup, setting a purse with a satin pouch in it on the vanity next to me. Inside, in little pockets of the satin pouch, were items of jewelry, necklaces, bracelets, rings.

"Ted, I can't. This is all real."

"It's everything I ever bought her. She threw it in my face when she left. I'd rather see it make someone like you happy than pretty much anything else, and you can use the purse, right?"

"You're sure about that?" He smiled and nodded, putting his hands on my shoulders.

"Thank you." I looked through what was there and handed him a simple gold cross on a chain, letting him fasten it around my neck.

I pulled out two or three bangles for my wrist and an ankle bracelet with a small gold transgender symbol. "Ted, was she like me?"

"Like you're going to be, I think. You make a beautiful girl."

Yesterday, I was putting on Maggie's golf outfit to settle a bet. Today I'm wearing clothes that belonged to some girl I've never met. Her ex-boyfriend, the guy whose cock I sucked, the guy I just spent the night with, tells me he thinks I'm transgender. I even packed a small suitcase full of decisions that backed up his claim. A soft smile crossed my lips as I fastened the bracelet on my left ankle. He just might be right.

"I only did this to settle a bet." We both knew I was lying, and he called me on it.

"Then why did you bother to fix your makeup and pick out a cute outfit for this morning? Why the ankle bracelet?"

"I, um, I..." There wasn't really any purpose to furthering my lie.

"Because I like it." I sighed and looked down at the vanity, folding the satin pouch and putting it in the purse with my compact and my lipstick. There, I said it out loud. I had admitted it to someone else.

"I like it a lot."

Breakfast was more like brunch by the time we got to the café Ted wanted to take me to. Evidently, Sundays at this café were a thing for him and the group he ran with. One of the other patrons was a very large black man that gave me a very flirtatious grin that I recognized immediately.

"Miki, everybody. Everybody, Miki. Some of you saw her at Zed last night." He glared at the large black man. They both laughed. Ted's was genuine. The other guy's sounded a little forced.

There was a buffet we helped ourselves to. I overdid it on the eggs benedict and the biscuits and gravy, which, from a purist point of view, live at opposite ends of the brunch spectrum. Combined with a large quantity of bacon and some fresh fruit, I stuffed myself. I hadn't eaten since breakfast yesterday and I had played a round of golf, spent the afternoon at a spa, closed a dance club, and given my first blow job. That kind of activity makes a girl hungry.

"Dante. Nice to meet you." The large black man stole the seat next to me. "You broke my heart last night; you know that, don't you?"

"Sorry," I chuckled. "It was my first time out in public like that. I'm still learning the rules. It looks like you're healing nicely, though."

"First time, really? Most girls like you act like scared kittens the first time they come to Zed."

"Girls like me, so you knew last night, everybody knew?"

"Not everybody, probably not even most, but girls like you are why I go to Zed. I guess that means my 'daddy' comment wasn't exactly welcome then, was it?"

"Well, not totally unexpected either. I mean, Maggie and I owned that room last night. We were the goddesses everyone else bowed to, even you." I winked. "It only makes sense a man like you that was used to being the alpha would try to assert himself." I laughed. "But you meant it literally. Oh wow, I guess I surprised you when I reacted like I did."

"Never been shot down like that before. Kind of bothered me for a while, but I'm a big boy. And that was the first time you went out dressed like that?"

I gave him the short version, stupid golf bet exacerbated by another worse golf bet, me in heels and a dress, dancing, history. "My car's at The Gables. Ted offered to give me a ride. When we got to my car, I remembered my keys and stuff were in my golf bag in my other friend's trunk. He let me crash and steal some clothes from his ex, so I didn't have to do the walk of shame thing."

"Does that mean I wouldn't be stepping on his toes if I asked for your number? Maybe we could go dancing at Zed again."

"Maybe a little. He's in the lead on hero points, but I just met him last night, too." I couldn't believe I was even considering this, but the feeling of confidence I'd had last night came rushing back. "This may be crazy, but what the hell, based on this weekend, crazy seems to be the new normal in my life. I think I'd like that." I took his phone and added my number. He'd probably never call, anyway.

Dante and I talked until Ted came back and suggested we go find Eddie or Maggie to get my stuff. The tone of his voice sounded like he was marking his territory.

"Later." Dante winked at me and stood up, putting his hands up like he was surrendering. There was suddenly some very obvious tension between him and Ted.

Ted was right. Without my phone, keys, and wallet, I was in a world of hurt. We tried Eddie's house again. No Eddie. Then we tried the spa, and they couldn't help me get in touch with Maggie, some privacy stuff that I guess I had to accept.

It finally occurred to me it was Sunday. I knew exactly where Eddie was. Ted and I found him sitting at Halftime watching the game, flirting with Ricki, our regular waitress.

"Oh my God, Mike?" Ricki recognized me immediately. "I never knew you were trans, too. When did you come out?"

"Wait, what? Come out?" I shook my head and gave her a strange look. "Trans, too?"

"Yeah, I thought everybody knew. I used to be just Rick." What followed was as cathartic as it was strange. Ricki told me her story, how her bestie, Jenn, had tricked her and everything had escalated from there, even meeting her husband, Victor. It was an amazing story.

I gave her the same abbreviated version I had given Dante at breakfast.

"No wonder you haven't been answering your phone. I've been trying to call you all morning. I thought you and Ted were just, um, busy." Eddie laughed.

"Yeah, busy trying to find you and Maggie so I can get my stuff back." I didn't laugh, but I couldn't say I was mad, either.

"Well, pull up a seat. She's on her way, and she's been trying to find you, too."

We sat down and ordered drinks. Ted didn't even try to leave, and I didn't ask why. Just like the clothes I was wearing, having him around had become comfortable.

"Cute outfit. Looks like you went shopping." Maggie smiled at me when she walked up to the table.

"Yeah, in Ted's closet. These belonged to his ex. My keys, phone, and wallet are in my golf bag in your trunk."

"Oh..." Maggie gave me a sheepish grin.

We waited until after the game. That turned into after the second game, a massive plate of chicken wings, more drinks, and a very interesting trip to the bathroom. Ricki was at the waitress station near the door and sort of followed me into the girl's room. "You and Ted, is that a thing yet? He seems to be really into you."

"We just met last night, but I enjoy having him around. It's kind of like I'm a slightly different person in these clothes."

"And you like it more than you ever thought you would, don't you?"

"It just feels right. What else can I say?" I think the way I blushed tipped Ricki off.

"Wait, you did it already, didn't you?"

"I kind of gave him a blow job last night. He was being so nice and then we started kissing. One thing led to another, and he gave me one. I felt like I owed him, but I got into it, and I didn't want to stop."

"It gets better. When I had sex with Victor for the first time, it was amazing. Just use tons of lube." She laughed. I shuddered. I hadn't even considered that what she was suggesting could be a natural progression from what I had already done. The ground under my feet was crumbling.

"I just wanted to reassure you. Trust your feelings on this. Go with what feels right, but be careful. Not everybody is going to understand. You look amazing and act so comfortable. I thought you had been dressing like this a lot longer than a few days. Whatever happens, know you can always call me if you need to talk."

"Thanks. If I let myself think about it, it gets overwhelming." I smiled.

"Then don't think about it. Just do it."

We went back to the table, and it occurred to me I really needed my phone. I wanted Ricki's number and really wanted Ted's. I mentioned it to Maggie, and she agreed. It seemed like the most natural thing in the world to get Ted's keys, even though Eddie and I were practically neighbors. I moved my clubs and put my phone and stuff in my purse. Maggie also gave me a bag I recognized from the spa. Inside were my makeup, hair care supplies, and the pink golf outfit that started this whole thing.

"I figure that's yours now." Maggie laughed when I pointed out the golf outfit.

We all exchanged numbers and headed home. I couldn't tell you what games we watched or who won, but I'd had a wonderful time.

The way Eddie and Maggie kissed goodbye answered my question about where he had been when Ted and I tried to find him last night. I looked at Ted and smiled. He smiled back and pulled me into a passionate kiss. Eddie gawked. Maggie didn't look surprised at all.

"You're my ride, you know that, right? I still need to go get my car." Ted just grinned and kissed me again.

The parking lot at The Gables was empty when we got there, which made sense for a golf course. Ted helped me load my clubs while I put my suitcase and the stuff from the spa in my back seat.

The note on my windshield asked me not to leave my car overnight as there was no security and no cameras, and the course would not be liable for any theft or damage.

"What's it say?" Ted closed my back hatch and came up behind me.

"Just a warning that there's no security and no cameras in the parking lot, so the club isn't liable for anything that happens." I smiled and dropped the note on the ground. "No security, and no cameras." I repeated as I dropped to my knees and my hands moved to unfasten his pants. Ted just smiled and leaned back against his car.

"Thank you for driving me everywhere today." I looked up and licked my lips as I pulled his cock free. Kissing it gently before flicking the tip with my tongue and slipping it into my mouth. This was so much easier than it had been in his car. I didn't have to support myself with one hand while I worked with the other to keep his cock in my mouth. All I had to do was relax and enjoy and explore. I could kiss and lick the bottom of his shaft and I could worship his balls. I could do all those things girls had done to me. All the things I had enjoyed so much.

Ted's moans, his hands on the sides of my head as I bobbed up and down his shaft; I felt so in control, yet so wanton. I didn't stop when he filled my mouth the first time, so I just kept going, sucking, and licking, kissing, and caressing his shaft and sack, teasing his cock with my tongue. Three times I made him spew his seed into my mouth before he softly begged me to stop. Kissing his exhausted soldier one last time, I smiled up at Ted and let him help me to my feet.

"Do I get a turn?" He kissed me hard and slid his hands across my body toward the button on my shorts.

"Um, I already came." I blushed, remembering how hard it had been to keep my focus on Ted as the shudders of pleasure ripped through me, filling my panties with warm, sticky goo. What kind of person has an orgasm from giving a blow job? Whoever they were, I guess I was becoming one.

All the way home, I ran the last two days over in my head. I enjoyed all of it, especially saying goodnight to Ted just a few minutes ago. Even, or especially, giving him that blowjob. I had cum in my panties, had an orgasm, shot my wad, jizzed my jeans. You get the idea; and did it while sucking his cock. I had enjoyed some intense fantasies while I masturbated before, but this was off the charts.

'What would it feel like if he were inside me?' I almost ran off the road when that thought drifted through my mind.

Monday morning was tough. I had stayed up late unpacking and putting everything away and doing stuff like organizing my makeup. When I got in the shower, I just stood there, letting the weekend run through my mind until the water turned cold. Getting mascara off is a bitch, and my forms, well, I'm glad there was solvent in the bag from the spa or I'd still have them on.

I had almost made it through the entire day when Vanessa, the girl in the cube next to mine, leaned over and complimented my manicure. "Are those acrylics?"

I laughed. I couldn't believe I had forgotten about my nails. There wasn't much I could have done, anyway. Acrylic nails are as much trouble to take off as they are to put on.

"Um, yeah. Carryover from a golf bet. To be honest, I forgot I still had them on."

"Well, bright pink is definitely your color." We both laughed. What else could I do? "Was it just the nails?"

It felt like I decided on the spot, but I had been working on this all weekend, longer actually. In the back of my mind, I had been thinking about what would happen if someone saw me dressed ever since I first tried on Maggie's golf outfit. I just went with what had worked all weekend. I owned it.

"Nope, check this out." I showed her the pictures Maggie had sent me of golf Saturday morning and then from the club Saturday night. Then I explained the bet, letting her know I had paid the price for my misogyny in full.

"Ooh, send me that one. I need to meet the guy you're dancing with." It was a picture of me grinding my ass into Dante. "I can't believe those are all of you."

"Me either. You might say I got a little out of control." The next picture was of me kissing Ted. I didn't share that one and was so glad there were no cameras at the golf course.

"I have to be honest with you Mike, that looks like a lot more than just paying off a golf bet."

"Yeah, well, I'm trying to figure that out."

By Wednesday, everybody at my office knew about my weekend. Some guys and two girls even asked me out if I'd dress up like that. Fortunately, I had a policy of not dating where I worked, and they all accepted it. The meeting with HR on Thursday was a surprise. They just wanted to get ahead of the curve and make sure no one was harassing me. That, and that I knew about the resources available through the company if this turned out to be more than paying off a golf bet.

The meeting with HR had made me think, though. When I got home, I changed into another outfit, relishing the feeling of peace it brought with it. Friday morning, I almost dreaded getting dressed to go to work. I never made that appointment with the spa to get my acrylics taken off or my extensions removed.

When I showed up at work to find an enormous arrangement of pansies on my desk. The card was unsigned and said, 'Pansies for the pansy.' My situation confused me enough and now I had to deal with crap like this.

I dropped them off at HR and took the day off. They said they would investigate.

"Can you talk?" I called Ricki and gave her a quick rundown. She was the only one I knew that could understand what I was going through.

"Sure. I'm off all day. Victor bought me a massage. You want to come along? I'm sure they can fit you in."

"Are you sure that's a good idea? I mean, what about Victor?"

"You sound so stressed right now. I think a massage is the perfect idea, and Victor trusts me. Besides, we won't be in the same room, silly." I had to laugh. "Just get pretty and wear something comfortable."

"You really think me dressing up is a good idea right now?"

"I'm just guessing, but I have a feeling part of the problem is that you haven't been dressing up all week. If I'm wrong, well, you enjoyed it last weekend, so what's the worst that can happen? Meet me at Le Madeline by Central Market at noon, and we'll have lunch first."

That gave me just over three hours to get ready. I took every minute. A hot bath with some scented bath oils from the spa came first. Doing and redoing my makeup until I was happy with it followed close behind the bath. Picking out the perfect outfit from the selection Ted had given me was last. A cute skirt, and a lightweight, sleeveless sweater. I put the adhesive for my forms in my purse and let the forms settle into my bra, thinking if I glued them on, I should do that after the massage. Frilly ankle socks and my sneakers, and I was ready. And, of course, if Miki was going out, she had to wear the ankle bracelet.

It also occurred to me I needed to go shopping. I only had two pairs of panties and one of those still carried reminders of my saying goodnight to Ted last Sunday night. Maybe Ricki could give me pointers on getting the cum out of my panties.

Maybe it was the process and maybe it was the result, but I felt a thousand times better when I looked in the mirror and saw Miki looking back at me.

Lunch was great. Ricki and I talked about what had happened at work and she told me how she got fired for coming out and then about how her family had reacted. "At Jenn's wedding, Victor helped me understand that the only people whose opinions matter are the ones that love and support me. I miss my parents, but I can't be responsible for their ignorance, because that's what it is. They just don't know any better."

I hadn't even thought about my family. What would my father think if he saw me dressed like I was now, and what would he think if he saw a picture of me dancing with Dante, or kissing Ted? Fortunately, I had almost three months to worry about it. For Ricki, everything had come together in a little over a month. Piece of cake.

I was a nervous wreck all over again. Thankfully, the massage was a good one.

Ricki went shopping with me and I bought a lot more than just underwear. I even bought a new outfit to wear for golf on Saturday morning. If I thought about what I was doing and tried to analyze it, none of this made sense. But here, shopping with Ricki, trying clothes on and buying more lingerie, it just felt so right, so natural. Then there was that face in the mirror, the way she smiled back at me. She was so relaxed, so at peace. How could I deny her that?