Bet Gone Wrong

Note - story includes cross dressing and humiliation.

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I should know better than to bet on sports. I'm Jamie, and my girlfriend and I lived together and our hometown football teams were meeting in the playoffs. My hometown team was a three point favorite which I made the mistake of bragging about to my girlfriend. She looked pretty pissed about that, then had a wicked smile as she looked at me.

"So let's bet on the game. I won't even ask you to spot me the three point edge your team has."

"So what do we bet?"

"If your team wins, I do whatever you want, and if my team wins you do what I want."

"For how long?"

"How long do you think it should be?"

Since my team was the favorite, I relished the idea of her doing whatever I want, so I made the mistake of getting cocky about it. "How about for a whole week?"

"You're on, dude."

I began thinking about what I'd want. Maybe have her naked around the apartment for the week, then minus bra and panties any time we went out. Maybe have her wear a collar, and have her on a leash at home. Of course I'd expect her to suck my cock every day, and maybe give me a rim job too. Have friends come over and have her serve us while nude. My imagination ran wild.

We sat down at home to watch the game and agreed that the week would start as soon as the game was over. My team started hot and got three quick touchdowns to go up 21 to nothing. I was so looking forward to a week of having her doing whatever I wanted. On the next drive, her team got an interception and ran it back for a touchdown.

That was kind of a drag, but we were still up 21 to 7, so I didn't worry. Then her team did an onsides kick and recovered on our side of midfield. They then proceeded to get a touchdown to narrow it to 21 to 14 at halftime. I was a little concerned, but I'd rather be up at halftime than trailing. Her team got the ball to start the second half, and ran back the kickoff to tie the game.

Now I was getting nervous. My team had done nothing offensively since the first quarter. Both defenses stepped up and there was no more scoring in the third quarter. In the fourth quarter, my team managed a drive for a touchdown to go up 28 to 21 and I was slightly relieved, until her team matched that to tie the game again.

Late in the game, my team had the ball with only about two minutes left, but deep in our own territory. We needed a couple of first downs to run out the clock and go into overtime. We ran the ball and made a first down only to have the running back stripped of the ball with her team recovering. They were about at our 30 yard line, but our defense stepped up and kept them from getting a first down.

It was fourth and 5 from the 25, when her team lined up and kicked a field goal to go up 31 to 28 with less than 30 seconds on the clock. They kicked off and had a super kick that went through the end zone, keeping us from running it back. My team completed a few passes to cross midfield. When we dropped back to pass once more our quarterback had to scramble and was sacked as time ran out.

I lost the bet and was really bummed about it. I was really bummed when I found out what my girlfriend had in mind for my week. She had me go in the bathroom and shave my face and every bit of hair from the neck down. I only had a little bit of back hair and she shaved that off. Then she had me shower with floral body wash.

She had me dry off then we went in the bedroom. I am a little taller than her but we are close to the same weight. She was fully prepared for her victory and handed me a pair of pink gaff panties. I had to push my nuts up inside me and tuck my dick back between my legs and put the panties on. Once I did, it almost looked like I had no cock.

She then had a pair of breast forms and adhesive and glued them to my chest. I was appalled. "How the fuck am I supposed to go to work tomorrow with these things stuck on me?"

"I guess that means Jamie, the girl goes to work."

"I can't go to work in drag."

"You'll have to."

"You can't do this to me, Susan."

"Like you wouldn't have humiliated me big time if I'd lost."

"Please don't do this."

She handed me a lacy pink bra. "Put on your damn bra, Jamie."

"You are so fucking cruel."

"Are you fucking kidding me? I heard you telling someone that you were going to have me spend most of the week naked."

"Only here -- not at work."

"And bring your friends over and have me serve them drinks and such while nude. You seemed to take great glee in what you were planning."

"You sure topped that."

"Look, Jamie, if you do what you're told, you'll get to have plenty of fun with me. If you don't, your ass will be cut off till I get over it. And that may take a while."

I slipped the bra on my arms and over my fake boobs. I couldn't manage to get it hooked in back. Susan came over and hooked it for me, then gave me a skirt that stopped above the knees, which I put on, then a top, which if I'd seen her in it, I'd have thought was cute. It was cut low and showed the cleavage I now seemed to have, and left a bit of midriff visible. I wasn't as thrilled with it on me though.

She sat me down and made me hold still while she painted my fingernails and toenails. Since my Adam's apple was visible, though it isn't as prominent as some guys, she put a choker over it. Then she made me sit still while she put makeup on me. I knew it always took her a while to get ready, but never really understood how much effort went into makeup.

Of course she finished it off with bright red lipstick, then she went to the closet and got out a wig that she'd used for parties and put that on me. Of course, even then she wasn't dome, but put a necklace and some bangle bracelets on me as well. After that, she had me look in the mirror and I didn't even recognize myself.

I had expected to look like a guy in not very good drag. Instead, I seemed to look like a cute girl. It blew my mind and when I thought about it, I was really disturbed. I don't want to look like a cute girl, or any other kind of girl for that matter. When I saw how I looked, it made my stomach queasy. It was bad enough having to dress like this, but I didn't want it to look right.

Susan grabbed my keys, wallet, and such and put them in a purse and handed me the purse. Okay, I had held her purse for her more than a few times when she needed me to. It's different when effectively it's my purse with my stuff in it. I felt like it was a snake that was about to bite me and wanted to drop it or throw it across the room.

"Okay, Jamie, let's go."

"Go? Go where?"

"To the mall, silly."

"You want me to go out like this?"

"You're not spending the whole week just hiding in the apartment."

"Why not?"

"Because I said you're not, remember, you lost that bet. Now get that cute little ass moving, Jamie."

"Like I want someone telling me I have a cute little ass."

"Better than saying you have a fat ugly ass. Outside, now. And I'm driving."

We went out and she opened the car door for me, which in itself felt weird. I got in and she came around and got in the driver's seat. Appropriate, I guess. She was really in the driver's seat for this week. The worst part was that nearly all the week was still to come and I already regretted making that stupid bet. It was too late now though.

"Jamie, dear, you need to keep your knees together getting in the car."

"I didn't notice."

"The neighbor did, and got a good look at your panties."

"Fuck."

"Tom just might. I've heard he swings both ways."

"Hell, no."

"Then don't advertise it, girl."

"Shit, I want out of this bet."

"After your week is over, and not until. You were the ass who wanted the bet, because you wanted me naked for most of the week."

"Please, Susan, I'm begging you."

"How quick would you have been to let me out of the bet if you'd won?"

What was I supposed to say? Sure I'd only have had her naked at home, but sans bras and panties the rest of the time. I would not have wanted her to welsh on the bet and would have tried to hold her to it, even I had friends come over to see her bare body. Honestly, I'd almost rather have been nude in public than dressed as I was.

I suppose the only consolation was that I looked so different that I hoped no one I knew would recognize me, if we ran into them. Still, I prayed not to run into anyone I knew. Susan drove us to the mall and parked. Of course the open parking spaces were near the far end of the lot, so I had to walk through the parking lot, dressed as I was, to the mall.

There were some guys who saw us and whistled and made comments. I was in a skirt, though Susan was in jeans, and one guy yelled out that I was cute in that skirt. I wanted to get far away from anyone, but definitely far away from that guy. I was shaking as we got to the mall entrance. Susan held the door for me, then took my hand as we wandered into the mall.

At least in the mall, I felt I wouldn't have men yelling at me, so I calmed down somewhat. We had only been in the mall for a few minutes when we ran into two of Susan's friends, Emily and Cynthia. When I saw them I wanted to hide, but Susan had a tight hold on my hand. They walked up and hugged Susan and looked me over carefully.

"So who is this little cutie?" Cynthia exclaimed.

Emily replied. "Don't you remember Susie telling us about her bet on the football game?"

Cynthia looked me up and down with her mouth agape. "Fuck. This is Jamie. I'd never have recognized you. Damn, girl, seeing you like this, I want to eat you up."

Susan piped up about this time. "I bet Jamie would love that, even if she hates that I made her do this."

I know I had to be blushing, since I could feel my face burning. Cynthia walked around me looking me over carefully. Then she ran her hand over my ass, which shocked the hell out of me. She came back in front of me, getting only inches away from my face. For a moment, I wondered if she was going to kiss me, but she just smiled and stepped back.

"Well, Susie, you'd better keep a close eye on this one or some guy may try to steal her away."

At that point, I had to speak. "I'm not into guys, and don't want some guy messing with me."

"There's more than a few women who would glom onto you too."

Susan pulled me closer. "At least for now, she's mine only."

"So what's up, girl?"

"We have some shopping to do."

With that Susan took me by the hand with Emile and Cynthia following. She took us to a kiosk, where they had a variety of jewelry. She looked through the wares and picked out a pair of one inch gold hoop earrings. She talked with the clerk, then sat me down in a seat and before I even knew what was happening, the clerk pierced my ears and put in the gold hoops.

I couldn't believe she'd had my ears pierced and earrings put in. I was almost livid, though I kept my voice down to avoid attention. "What the hell are you doing?"

"Just adding a finishing touch."

"Pierced ears?"

"After this week, you can take the earrings out and the holes should close back up."

"This is outrageous."

"You lost your bet and have to do what I say this week, so don't get your panties in a wad."

"It's bad enough you have me in panties, a bra, and a dress."

"If you want to be a bitch and give me a hard time, then you'll pay."

With that, she talked again to the clerk, who came back over. Susan lifted the bottom edge of my top and the clerk pierced my belly button and put a small fake jewel in there. Emily and Cynthia had been looking at jewelry and came over to look at my belly button piercing. They had big grins as they looked at me, and Cynthia did a funny little squirm.

"That is so sexy. Jamie, you'll have all the boys wanting you now."

"I don't want any boys wanting me."

Cynthia continued. "I'll bet it's a little sore, otherwise I'd be licking that once we're somewhere more private."

"It is still tender."

"Maybe I should kiss it and make it better."

Susan laughed. "Maybe I should turn Jamie over to you for a few days."

"We could have a nice threesome with me, Jamie, and my boyfriend. Carl is bi and likes girly boys."

I know my voice was shaking. "Fuck, no."

Susan looked at me. "As long as you behave and don't give me a hard time, I won't."

The women finished up at that kiosk and decided to get some dinner. Of course we could not go home where I'd be out of public view, but had to go to a restaurant there in the mall. There was a young man as our waiter, and he said he was lucky to be waiting on four such beautiful ladies. That just made me want to hide, particularly when Emily spoke up and pointed at me.

"Well, most of us have boyfriends, but Jamie there doesn't have a boyfriend."

I'm not sure how I had the aplomb to speak up but I did. "Silly, you know I don't have a boyfriend because I prefer women."

Cynthia piped up about that time. "I still say you need to give boys a try."

"Not happening, girl."

The women ordered wine and I asked for a beer. We were all under 30, so the waiter, Jeff said he needed to see ID. The women produced their ID, but I decided I was not going to show him ID with me as a male.

"Oh damn, I left my ID at home."

Emily spoke up about that time. "I thought it was in your purse."

"No, I forgot it. That's why Susan had to pay for my new earrings. I'll pay her back though."

You know my idea of paying her back, would not be anything she'd like. Susan said she'd told me not to bother paying her back. I told her I had to, because I certainly couldn't be indebted to her for something like that. While we were trading comments, Jeff had gone off to get drinks for the others. Clearly all three women were having fun at my expense.

After a while, even though I wasn't drinking much, my bladder got full. What the hell was I supposed to do? I sure as hell couldn't go into the men's bathroom looking like this. I was afraid to go to the women's bathroom. I knew I couldn't hold it until I got home, but I was sure there were no unisex bathrooms. I leaned over and whispered my problem to Susan.

Susan stood up and took my hand drawing me to my feet. "Ladies, we need to visit the facilities. We'll be back shortly."

I was still quite uncertain, and saw smirks on the faces of Emily and Cynthia. Before we reached the restroom, Susan quietly told me to just be cool. "Just go in a stall, close and latch the door. Pull up your skirt, and sit on the toilet. Don't stand to piss the way you normally do."

"What if someone -- "

"Don't take it out and wave it around. Just pee, put your clothes back. Wash your hands and leave."

"I've never been in a women's bathroom before."

"There's toilets and sinks. No urinals. Just try not to be too weird. And don't perv on the other women."

"Why couldn't you have just let me dress like a guy?"

"And miss all this fun?"

"Fun for you -- not for me."

There were two other women, when we went in. I tried to look inconspicuous and scurried into a stall, closed and latched the door. As I did, one of the women looked at me funny and I was worried that she knew. Even though I desperately had to pee, I was so uptight that it took a while to relax and let that happen. I finished and Susan was waiting and we left and returned to our table.

The other two were snickering as we sat back down. Emily piped up. "So how do you like your walk on the wild side?"

"I just want to walk on the side I normally do."

"So has that taught you anything about betting?"

"Don't bet if you can't afford to lose."

Everyone had a good laugh at that. We finished our meal. Damn, I wished I could drink, though I did sneak some sips of Susan's drink when I thought I could get away with it. I suppose it was good. I'd have been inclined to get really drunk, and that could have caused some major problems. A little took some of the edge off, while I was still in control of myself.

After a while, with the food and company, I almost forgot how I was dressed. When I had time to think about it, I wondered why I was putting up with this. I'm straight, I like girls, I'm not interested in boys. I had no attraction to cross dressing, Still, I allowed her to dress me up, and make me look as much like a girl as any of her friends.

I realized that I really like Susan. I mean she is both nicer and better looking than I otherwise might be able to get. Hey, when you're a nerd who isn't very tall or athletic, and who isn't wealthy or especially charming, it's hard to attract the attention of the prettiest girls. Yet, I seemed to have one of the prettiest. My friends told me she was way out of my league, but she liked me.

Beyond that, I lost my bet, Susan got to dress me up, but I wanted payback one of these days. If I welshed on my bet, first I'd be sleeping alone on the sofa for a while, and second, she'd never follow through if I got the upper hand. Also I wondered if I had a mild submissive side. There were limits as to what I'd do, but I'd let her make me do a lot of humiliating things as part of this bet.

It was Sunday evening, so all of us had to go to work the next day, otherwise, Emily and Cynthia made it clear they would have me go out dancing in drag. The stores in the mall were closing so we said our goodbyes and Susan and I headed home. As soon as we got home I felt relieved. I figured I was free of the humiliation for a while.

"Thank God. Now I just want to get out of these clothes."

"Jamie, dear, you forget, you're mine for a week. You're dressing like that till I tell you otherwise."

"I can't take off this lousy skirt and blouse?"

"They're hardly lousy. They actually are quite nice. But of course you can take them off. I have a sexy nightie for you to wear.

"Oh, fuck."

Susan came up to me and kissed me. "If you do what you're told, we just might."

She had me take off my skirt, top, bra, and panties, but there was no relief in that. She had a frilly pink nightie with another pair of gaff panties. My fake boobies were apparent through the nightie, since it was sheer, and the panties were thong style, so I just had a narrow strap up the crack of my ass. She had me keep my wig on, and I felt even stupider than I had just in skirt and blouse.

She took my hand and led me to the bed, where she pushed me down on my back. She climbed onto the bed, pulled up my nightie and began to suck on one of my faux boobs. She acted like they were real ones then kissed and sucked first on one, then on the other. I really felt weird and of course there were no nerve endings in those fake titties. Still there was some strange thrill in having her suck them.

After a while, Susan paused and looked at me. "I wish these were real."

"Not happening, honey -- not ever."

"You're so narrow minded."

"If you want a woman for a lover, I'll leave and you can find one."

"Don't get your panties in a wad, Jamie."

"If my panties are in a wad, it's because you have me wearing panties."

She rolled off me, took off her bra, and told me it was my turn. I love her boobies and have no problem with enjoying them. I spent quite a while kissing, licking and sucking on them before I paused. I looked at her and she spoke.

"If you can make me cum, I won't peg you."

I don't want anything stuck in my ass. I slid down her body and lifted on her hips. She raised them from the bed and I pulled her panties off. She is usually shaved down to a landing strip above her pussy, which is how she was that night. I like cunnilingus and felt sure I could bring her to orgasm. I started dimply by licking her slit. I got my tongue in her and then followed with a finger.

I heard her begin to moan, which meant I was doing something right. As I licked, her clit peeked out of its hiding place. I know she enjoys having that licked, but can't take too much direct stimulation. I I got my fingers deep in her and found her g-spot. I stroked that as I continued to lick her sweet pussy. Pretty soon, she had her legs around my shoulders and was pushing her cunt into my face.