Bet Gone Wrong

That was another good sign and I kept licking and fingering her until with a shriek, her snatch grabbed my finger and she seemed to go into convulsions. Look, I'd brought her to orgasm before, but I swear, I'd never seen her quite like this. She almost sounded like she was weeping, and had her quim so firmly pressed to my mouth that it was hard to breathe.

Before too long, she slumped back onto the bed, releasing me, as she panted. I think she was easily as out of breath as I was. That was good, as far as I was concerned. I'd have spent the whole damned night licking her pussy, if it meant she wouldn't peg me. As she slowly recovered, I moved back up and renewed my acquaintance with her luscious breasts.

I moved back and forth between them, kissing and giving them love bites as I fondled that one I didn't have my mouth on. I heard her continuing to moan, though I knew from experience that it was hard to make her cum just from pleasuring her titties. I kept at it, until she grabbed me and brought me up to kiss me with the sort of passion she seldom shows.

We kissed for a long time before she rolled me onto my back and ranged over me. She lifted my hips and pulled off the panties she had me wearing, then lowered herself on me. I could feel my cock sawing around her perineum, as she resumed kissing me. Then she lifted her hips, reached down and guided me into her sweetness.

I don't much care who is on top, as long as my prick is in her pussy. In a way, it was nice having her on top, because it was easier for me. I fondled one breast with one hand, while the other hand caressed her ass. I wanted to make this last so I had to focus on something other than my dick in her snatch. She had a nice slow tempo which suited me just fine. There was no need to furiously pound.

We kissed as we fucked and as I toyed with her. and as we continued, I snuck a finger in her ass. She moaned, bit my lip lightly and did a funny little squirm. She obviously enjoyed it and had another orgasm shortly before I filled her womb with my jizz. She collapsed onto me and we both lay there panting as we came down from our respective peaks of ecstasy.

Pretty soon I heard her breathing change and it was clear that she had fallen asleep on me. The weight of her lying on me was not as issue so I let her snooze away as I drifted off to sleep, with my softening cock still partly embedded in her. Later, I felt her slide off me and we both slipped back into peaceful slumber. Yeah, I still had fake boobs glued on me and was in a nightie, but didn't care.

......................................................................................

I woke up in the morning, lying on my side with Susan spooning me and holding one of my breasts. She woke up almost immediately after and I rolled over and we kissed. I knew we both had to get to work before too long. I still had my breast forms glued on and wanted to get those off before I went in to work.

"Susan, dear, can we take these things off so I can get dressed and go to work?"

"Jamie, you're going to be a woman 24/7 for the week. I'll get you a nice dress to wear."

"Fuck, baby, please don't do this."

"Jamie, you lost the bet, and planned on having me either naked or without bra and panties all week."

"But people would not have known you weren't wearing panties."

"You also told one friend you wanted to put me in very short skirts and near transparent blouses. Folks would have known all right."

"You heard that, huh?"

"Yeah, so suck it up honey. You're a woman this week."

"But that was just something I was thinking about. I didn't want to really embarrass you."

"So you weren't planning on having your male friends over and having me serve drinks and snacks in the nude?"

"Shit."

"Take a shower, Jamie. I'll get you some clothes, then do your makeup after."

"Is there anything I can do to -?"

"Embrace your inner woman, and get that cute little ass moving."

I showered, trying to think of how I could appear to be doing what Susan wanted, yet still not humiliating myself. Could I hide a set of male clothes in my car, find a place to change to them, and change back before returning? That still left the problem of flattening my chest and redoing makeup before coming back. It seemed that Susan thought much the same.

I came out of the bathroom, to find Susan with a dress, bra, panties, and low heels for me. She also had something to say. "Jamie, just to keep you honest, I'll call you a few times today and every day. When I do, you'll need to shoot a pic of yourself dressed in this, with a proper time stamp and EXIF data for your office. You need to send it immediately and I should also be able to see your cube."

Okay, it is possible to photoshop that mess and alter the time and location codes, but it takes time to do and can be detected by anyone with some skill. I knew that she had tech savvy friends, so there's no way I could quickly do that shit and have it go undetected. Basically, I was screwed. I'd not only have to wear the clothes out, but 'prove I wore them all day.

I knew I had to go to work, and I couldn't see any way to do it while dressed normally. Susan helped me into a bra, and had a clean pair of gaff panties that hid my junk. I asked her for slacks, but she insisted I wear a very feminine dress. She had no intention of making this easy. She put makeup on me including eye shadow and bright red lipstick. I still had on nail polish from last night.

She was not at all trusting, though I didn't see a way to escape this. She walked to my car with me and checked to see that I had not stashed any male clothes there. Obviously, that wouldn't keep me from buying something but there was no way I'd recreate the makeup and I didn't think I could fake the photos decently.

I shook as I drove to work. I'm normally in a cube by myself and don't necessarily work much with others during the day, but there was little chance of going unnoticed. I parked and went in a door that had fewer people around, then acted normal as I walked to my cube and sat down. I logged onto my computer and began to work.

Of course it couldn't last and about half an hour into the day, my boss walked by, looked in my cube and saw me. "Who the fuck are you, and why are you in Jamie's workstation?"

I turned around to face him, not that I wanted to, then replied. "I can explain."

His eyes got big and his face turned red. "Jamie, what the holy fuck is going on?"

He was loud, and almost immediately, several people gathered to see what was happening. I was shaking, as was my voice as I spoke. "I lost a bet, and have to be like this for a week."

"You got to be shitting me."

"I wish I was. Believe me, this isn't what I wanted to do."

I could hear some snickers and I even heard a wolf whistle from one of the half dozen people gathered around. I suppose there would have been more but that was about as many as could get some kind of look at me. I could feel my face getting hot, so I know I was blushing, though the makeup hid a little of it. If there was somewhere I could have crawled to hide, I would have.

My boss was as red faced as I felt. "What the fuck am I supposed to do with you, Jamie?"

"Let me work."

"What the fuck bathroom do you expect to use?"

"I wish we had a unisex bathroom, but since we don't I was avoiding drinking anything. I planned to go to Lorenzo's for lunch since they have single person bathrooms."

"I sure as fuck don't want you in the men's room like that, and I can't imagine the women want you in their restroom."

"I don't want to go in either one."

"So how often do you dress like this? Is this some kind of permanent shit?"

"I never dressed like this before losing that bet, and it's only supposed to be for a week."

"Honestly, I'm not sure I even want your ass in the office dressed like that, but we have too much work to let you take off."

"Could I work remotely?"

My boss shook his head and glared at me. "You know we don't like to do that, but I'll talk to my boss."

He left in a huff and several of the other people wandered off as well. I just wanted to be left alone, or better yet to work remotely until this week was up. Finally the crowd was down to one guy. I tried to go back to work, but he stepped into my cube as leaned over and spoke softly. "That's some nice lipstick you have there, doll."

"I'm no doll, and I'm only wearing this because I lost a bet with my girlfriend."

"Yeah, I'll bet. You know what I want?"

He was getting creepy and I wanted him out of my cube and away from me. "I don't care what you want."

"I want that lipstick smeared up and down my cock."

"You sure as hell aren't getting that."

"Right. You're just a little slut. I bet you'd rather have my cock in your ass."

I was really getting shaken now. "Leave me the fuck alone."

"I want to feel your ass grab my cock as I fill your butt with my cum."

"Get out of my cube."

"I'll see you later, slut."

I sat there shaking before I could get back to work. Even then, I found myself looking over my shoulder and too often seeing that same jackass walking by and looking in my cube. I was a nervous wreck by the time lunch hour arrived. There was a little restaurant near our office, and when it looked clear, I rushed from the office and quickly walked to the restaurant.

I grabbed a table well away from everyone else, and ordered some food. I was constantly looking to make sure the jerk wasn't there. Earlier, I'd said I was going to Lorenzo's but I was afraid he overheard me so instead I went to Schwartz Deli. They just had standard men's and women's restrooms but I figured no one there would know I was in drag.

Again, I drank as little as possible, then hit the women's room after I finished my meal. Mercifully, no one was in the women's room when I went in, so I just went in a still and latched the door. I sat, since I was afraid to stand and pee in the women's restroom. As I was washing my hands after, a woman came in but she paid little attention to me.

I'd already paid, so when I was done, I quickly left the deli. I was almost paranoid, looking around constantly on my short walk back to the office. I was halfway to my cube when the jerk came around a corner. He stepped in front of me, blocking my way, and I backed away from him, looking around for another route to my work station.

He sneered at me. "Well, doll, you got away from me this time, but I'll have that ass before this is over."

He came toward me, and I backed up against another cube as he went by. Once it seemed like he was by, I rushed away, though not before he patted me on the ass. I no more than sat down, before I had a text from Susan, wanting a pic of me. I quickly shot one and sent it to her, then tried to get back to work. A little later I was called to my boss's office.

"Jamie, if it were up to me, I'd never see you in this office again, however you dressed."

"I swear, it's only a week."

"And you think anyone will forget it, even if you dress normally?"

"I can hope."

"I asked my boss and was told you can't work remotely. And since we're starting month end, you can't have time off either. And don't think you can call in sick."

"I get it. But there's a guy who is harassing me and making lewd suggestions."

"The way you're dressed, what do you expect?"

"Can't you make him stop?"

"You dress like this, Jamie, you put up with the shit that goes with it."

"But isn't that sexual harassment?"

"You may dress like a woman, but you ain't one, so suck it up."

"So that's how it is?"

"This shit is your doing, when you come in here dressed like some tranny faggot."

"But this isn't -- "

"It's what you chose to do. Now get your ass back to work."

He was right, in one sense. I had too much damn work not to be working. I just never expected the kind of shit I was getting. I think the jerk came by several more times, but I was too busy working to notice. What I did notice was that my boss told someone that they needed to get to work instead of loitering around my work station.

I suspect that was the jerk, and think he steered more clear of me after that. I suppose I should be glad my boss did that much, though it was less for my benefit than to get that person doing what they were paid to do. I had more than enough work to do and stayed past my normal quitting time, but that meant there were fewer people around.

That was good and bad. With fewer people, I had less grief, but also less protection if someone decided to make problems. I did get another request for a pic from Susan, which I sent. I decided I wanted to leave the office before it was dark outside, so I shut down and left as quickly and quietly as possible. No one bothered me on my way to my car, but there was a note on my windshield.

I know it was from the jerk, and it said he would have my ass before long. I got in my car, locked the doors, and drove off, checking around to make sure I wasn't being followed. I got back to the apartment and rushed in hoping that none of the neighbors saw me and realized that I was in drag. Once inside, after locking the door, I just slumped on the sofa.

When I felt comparatively normal again, even if I still looked weird, I checked my personal e-mail. I had a message from a recruiter, asking if I was open to new job opportunities. I quickly replied that I was, and forwarded my resume. I suspected that even after my week of drag that I'd still get a lot of shit at my current employment.

Susan got back shortly after. I stood up, still shaken from my day. She walked over and hugged and kissed me. That was the reassurance I needed and I eagerly kissed her back. We stood kissing for a time before she led me to the sofa and we sat down and continued to kiss. I stroked her back and found her stroking mine. After my day, any love and warmth was wonderful.

"Well, Jamie, it seems you were a very good girl today."

"Please tell me you're going to give me a break and cut this short."

"Sorry, babe, you owe me a full week."

"You have no idea the shit I went through today."

"Probably just a more intense version of the shit that every woman goes through in her life."

"I don't think I can take it."

"After showing up in drag today, do you think showing up in male clothes tomorrow everything will be wonderful again?"

"Not wonderful, but probably better."

"Maybe, maybe not. At any rate, I expect you to do what you promised, just like you'd have expected that of me if I'd lost."

Susan was the best thing in my life -- by far, but she was putting me through the worst that I'd ever suffered. Maybe she was right. Maybe women did suffer the same things. I hadn't done those things to women -- at least I didn't think so. Why did I have to atone for the sins of a lot of incel jerks? Wasn't it enough to try to do right by women myself?

In spite of my begging and pleading, she wouldn't give an inch. I tried taking a macho stand and just refusing. She got up and went in the bedroom and began gathering clothes.

"What are you doing?"

"I'm taking all my stuff and going to stay with my sister for a while."

"How long were you going to be gone?"

"Probably forever."

"Why?"

"If you won't pay off your bet, then I have no respect for you. And I won't stay with a guy I don't respect."

"Susan, please don't go."

"If you want me to stay, you have to fulfill your end of the bet."

"Can't we work out something different?"

"That wasn't the terms of the bet."

"Susan, you won't make me have sex with men."

"I promise I won't. And we can make love every night."

Shit, so my choice was either dressing in drag for a week, or losing my knockout girlfriend. All my requests were for naught. I told her I'd do what she wanted, then she took me to bed and we had some of the best sex I'd ever had before we paused for dinner. Of course, she ordered food for delivery, and I had to take the delivery dressed as a woman. At least it was only one person who saw me.

...............................................................................

So basically I was stuck in drag for a week. I went into work the next day, and while I was scared on Monday, on Tuesday, I was angry. Sure enough the asshole came by my cube later with his usual nonsense.

"I want to see my cock in those bright red lips of yours."

"Try it and I'll bite that goddamned thing off, and even if the doctors reattach it, it'll never work right again."

His face turned white and he got the hell out of there immediately. A little later my boss came by and stuck his head in my workstation. He looked angry and almost snarled at me.

"Did you threaten to harm another employee?"

"He's been sexually harassing me and you haven't done a damn thing about it, so don't give me any shit if I responded."

My boss's face turned very red, and he stomped away from my cube. There was a woman, Rachel, who works in the cube next to me.

She came over, leaned down, hugged me, then kissed me on the cheek. "Chad has been pulling that shit on women around here for a long time. It's about time he got a taste of his own medicine."

"I'd had just about enough of his bullshit."

"Jamie, if you need to use the restroom, let me know. I'll make sure you don't have any problems in the women's room."

"Thanks, Rachel."

She gave me another kiss on the cheek and went back to work. A bit later in the morning, I was called into the office of the vice president who was my boss's boss. He had me sit down, then gave me a hard look before talking.

"What happened between you and Chad?"

"He threatened to sexually assault me, and I told him I'd hurt him if he did."

"He said he was only joking."

I still had the note that was on my car yesterday in the purse Susan had me carrying. I pulled it out and put it on his desk.

"Does that look like a joke to you? That was on my car yesterday, after he pulled the same shit then."

He looked at the note and shook his head. "I understand your anger, but -- "

"No buts. I understand he's been pulling that on women around here for a long time. If you don't do something, at the least, you'll have suits for allowing sexual harassment."

"I should have known you were a troublemaker, Jamie."

"Who the hell is the real troublemaker? Him for the bullshit he's pulled, or me for not being willing to take it?"

He dismissed me and I went back to work. Just before lunch, I looked up to see Chad standing by my cube, looking at me. I said nothing, but I glared at him and pointed a finger at him. He rushed off.

There's a little Thai place not far from the office that I liked to go to for lunch. I went there and they seated me, and while I was waiting on my food, I got a call from the recruiter who had e-mailed me the previous night.

"So Jamie, are you serious about another position?"

"You bet. I'm more than ready, particularly if the money is decent."

"I know I can get you ten thousand more than you're currently making."

"That sounds great."

"You need to go by there for an interview after work today."

"Today? But -- "

"Jamie, I have friends. I know how you're dressed and so do they, and they have no problem with it, but they want to move on this."

"Shit."

"Do it. You know it's turning toxic where you are. This will be better, and pay you better too."

"Fine."

"I'll text you the info."

About that time, my food arrived. I began to eat, when Susan wanted another pic. I did another selfie in the restaurant, so she could see that I was doing what she wanted. I ate my lunch, stewing over having to go to a job interview in drag. I went back to the office to see a smiling Rachel, along with grim faces on a few men.

"Well, Jamie, they canned Chad. You're a hero to the women, and a villain to a lot of the men."