I Never Had a Chance

The following is an absolutely true story. It doesn't have as much sex as many others, but it was wildly erotic for me and my Mistress. Some parts may seem a bit hurried because I don't remember everything as vividly as I would like.

*

"You're going to lose a bet tonight."

That's how it all started. My fiancée uttered those words that sounded so much like a strange fortune cookie.

"You're going to lose a bet tonight."

Now, you should know that we don't have an entirely conventional relationship. At my request, Sam has taken the reigns in our relationship. It's not 24/7, but if she demands something, I must do it. So when she told me that I would be losing a bet, I had a feeling that the odds would probably be in her favor.

In other words, I knew I'd be losing a bet tonight.

"See, Jeremy, I hate that I can't talk to my friends about our sex life. They tell me about theirs, but our life is too out there for me to mention. So I've figured out a way to have a little talk with my friends. But, for that to happen, you're going to have to lose a bet. We're going to meet Allyson and Nikki at the bar in an hour. But for this to work, you're going to need to go get us some alcohol for home, first."

On that cryptic note, I went out to get some Vodka and Tequila, Samantha's favorite booze. I was incredibly worried, because it was at my request that she didn't talk about our sex life with her friends. On the other hand, I was willing to do whatever it takes in order to have permission to have an orgasm. It had been 5 days since I'd last been allowed release, but without her having to go to law school, they had been very difficult days. She'd spent much of the time on her back, with my head between her legs. And when I wasn't pleasing her, she was teasing me. We'd watched every one of those HBO specials about sex or hookers while she slowly rubbed my cock. She'd bring me to the edge and then stop. And this had happened for 5 straight days. So I was ready to do whatever her bidding, regardless of how embarrassed I was.

When I got home, she complemented me on my choices of alcohol. Then:

"Take off your clothes."

I stripped off the clothes, including the panties, and stood there in my CB-3000. She pulled a key from around her neck and unlocked me.

"There you go, Tiger. But don't go thinking you're going to cum anytime soon."

I started to get dressed again but she stopped me.

"No. Don't put on those panties. You can wear your boxers tonight."

I was surprised, but was not about to complain. She'd made me wear a different pair of panties each day since her last final and I was happy to wear something a bit more comfortable.

"Now, I saw a story recently that says that University science and math programs have begun to be dominated by women. There are simply more women in science and math then men. This is, of course, quite a change from even a few years ago. However, when we get to the bar, you are going to bet the opposite -- you're going to pretend to be a chauvinist and you're going to go on and on about how men are better than women in math and science."

"But, sweetheart!"

"Shh. No buts. That's all you need to know. Now, let's go to the bar."

So we walked the 4 blocks to our bar. We sat there for probably 15 minutes before Allyson and Nikki walked in to find us. Both girls are gorgeous and, if I hadn't been so wildly in love with Samantha I would have tried to convince Sam to have a threesome with either girl. But I didn't want to screw this relationship up, so I didn't.

Allyson is 5'6 and brunette, with a cute little pixie haircut and small breasts. Now, I know I'm the exception to the rule, but I prefer smaller boobs. Especially since it meant Allyson rarely wears a bra. Nikki is closer to 5'9 and blonde, with large and perfect breasts. Both were cute, but neither was in the same league as Sam.

We talked and had about 2 drinks each when Sam gave me my cue:

"You know, I read an article today that said that there are more women in math and science now than ever before. Jeremy, have you found that to be true among your students?"

I knew better than to veer off track. "No. I think men simply have a better aptitude for those fields. Look at it. Men do better in Chess and in music, both fields which need an intuitive grasp of math. Women just can't do it."

That got the girls going. Nikki almost shouted "Are you kidding? I'm better at math than you are, I'll bet. Let's do some math!"

I dug my grave deeper. "No, Nikki. As much as I like you, I'm just better at math than you guys are." I did my best to be as chauvinistic as possible. "Really, men are simply better at thinking than women. You guys are better at other stuff, like giving birth and peeing sitting down, but men are..."

"Ok, smart guy. Let's make a bet. If we are right, we get to show you what it's like to be a woman. If you win, you can have anything you want." Sam said.

"What's the bet," I asked.

"If there are more women in college math and science courses, I win. If there are more men, you win. Deal?"

"Fine," I said. "The house is a mess. If I win, you three all have to clean it from top to bottom -- in just your panties."

Nikki and Allyson blanched, but Sam soothed them. "Guys, we won't lose. And when we win, we'll make him do whatever the hell we want to teach him a lesson. Really, if we lose, I promise to give you both one thousand dollars. But it won't happen."

Allyson asked "You read this already? In a magazine?"

Sam said "Yeah. Just today. I'm not wrong. The bastard will lose this bet. Just think of some things we can do to him."

Nikki said "I'm in."

We all looked at Allyson.

I said "That house is really a mess, Al. I can't wait to watch you clean it."

Allyson looked me dead in the eye as she said. "I'm in. Let's go."

We paid our tab and went home.

Ch. 2

When we got home, we went right for the computer. Sam sat down and looked up the article online. It only took her a second to find it. She was right, of course. I had lost the bet.

"Jeremy, go and make us some drinks. I'd like a shot of Cuervo and a Vodka tonic. Girls, the same?"

The two girls nodded their agreement.

They sat down in the living room and whispered to each other as I walked in.

Allyson said "Listen, Jeremy. We need a minute to discuss your fate. Go across the street and get some mixers for our drinks."

I did as I was told, worrying the entire time about what was going to happen when I got back. I briefly thought about going back to the bar, but knew they'd find me. And Sam would make everything 1000 times worse for me thereafter. And the 5 days of not cumming was making me more pliant than usual.

As I returned, Nikki called me over. "We've decided the best way for you to learn your lesson is to see what it's like to be a woman. So we've decided we want a little fashion show." She was slurring her words a little bit.

Sam continued for her. "But you'd look terrible in a skirt right now, so we've decided to have you shave your legs. Go into the bathroom and take a shower, and make sure you don't have a hair on your legs when you come out."

I took the shower, but wasn't sure how to shave my legs. Getting the knee-pit was hellish. But I managed and 10 minutes later I got out of the shower.

I heard Sam's voice call "Jeremy -- no need for you to get dressed. Just put on a towel and come out here."

Nervously, I came out with the towel around my waist. Sam said "No, no. This will never do. A lady wears the towel around her chest. And you didn't shave your chest!"

"You didn't tell me to!" I protested.

"A woman would've figured it out," Nikki volunteered.

As I lifted the towel up to my chest, the girls began feeling my legs.

"He missed a spot." "Oh, no, this will never do."

"Girls, I think our new girl needs some help," said Sam as she yanked the towel from around my waist. From Nikki and Allyson's reaction, I could tell that the girls had agreed to this while I was in the shower. My erection was straining, but none of the girls commented on it. They just pretended like this was something we often did.

"The first thing we need to do is wax her. She looks terrible." Nikki ran her finger up the inside of my leg.

Unfortunately, I have a bit of body hair and it took awhile to wax me fully. I'll spare you the details, but the girls really seemed to enjoy inflicting the pain for my earlier "chauvinism." They kept drinking during the waxing, and seemed to be enjoying themselves. For my part, the pain of having the hair ripped out managed to shrink my penis down to flaccid.

"Ooh, look at little clit!" squealed Allyson, as they flipped my back over so I was face-up. "It was so hard earlier, but now it's like a little turtle. It's gone into hiding!"

"Now, we girls are pretty open with each other, but we don't walk around naked. Here, I picked out some clothes for you...Jenny." And that was that --I was now named Jenny.

I picked up the clothes that Sam had laid out and began to get dressed. First, I put on the black thong. Then, I pulled the black skirt up. It reached my legs. I had some trouble putting the bra on, so Allyson helped me. Finally, I put on a sheer satin blouse. It was almost as red as my face.

The girls, by this time, were in hysterics. And, for my part, I was very clearly excited. My panties and skirt didn't do a very good job of hiding my throbbing erection.

"Next lesson: How to be a girl!" Sam practically squealed as she said this, so I knew two things: 1. That she was excited and 2. That this was going to be bad.

Chapter 3

"One of the most important things all guys want is to have their dick sucked. Every girl has to know how to do it. Why, you ask me all the time to blow you."

This wasn't true, of course. Sam hadn't put my cock in her mouth in months, though I'd eaten her out at least 4 or 5 times per week. I didn't interrupt her, though.

"So you'll be pleased to know that I have a dildo for you to suck on! It's not as good as the real thing, but it'll do. It's just too bad that I don't have a strap-on so that it would be more realistic."

"Maybe next time," laughed Nikki.

Sam held our small training dildo out in front of her crotch and told me to get on my knees. I pleaded with my eyes.

"You lost the bet, Jenny. Now get on your knees!" Called Allyson from across the room, where she was making herself another drink.

I complied. I sucked the dildo in front of Sam's friends. I wish I could've said no, but it was really my idea that she take charge. So I did it.

"Lick the sides!" instructed Nikki.

"Deep throat it!" called Allyson.

At that, Sam began to thrust her hips, pushing the dildo deeper into my mouth. I started coughing and gagging. She pulled it out.

"Well, girls, I think Jeremy's learned his lesson. I don't think he'll be making any more chauvinistic bets anytime soon. I think the night should come to an end."

Allyson protested. "But real girls need to know how to take it in the ass!" Nikki laughed.

Sam said "Maybe next time. But I think the poor boy has had enough for the night. And I think none of us will ever look at him the same again. She reached down and stroked my cock once for effect. "Besides, I have to have sex right now or I may explode."

The girls said their goodbyes, thanking Sam for the entertainment. "Bye Jenny!" they called as they stumbled to their waiting cab.

As soon as the girls were gone, Sam told me to go to bed and lay down. I complied, of course. She put base of the dildo in my mouth and told me to be still. She slowly impaled herself on it as her ass slowly closed onto my nose. I couldn't see anything, but I could hear her talking to me over the hum of her vibrator, which she was using as she lifted up and down on the dildo.

"You did such a good job tonight, sweetheart. And I love your hairless body. I have such a good surprise for you in the other room. Let me have my orgasm and then I have such a surprise for you!"

She continued to thrust, faster and faster until she cried out, collapsing forward so I could feel her hot breath on my straining cock. After a moment, she got up.

"No touching, Jeremy! I need you just as you are for your surprise. She then took the tie I'd worn to work that day and tied it around my head as a blindfold.

"I'll be right back!" she called as she left the room.

After a few moments, I heard her enter the room. She told me to open my mouth so she could take the dildo out of it. I did so, but as soon as the dildo was out, I felt her wet panties being forced into my mouth.

"You'll need something to bite down on" she said. She then pulled out our ropes from under the bed and secured me so that I couldn't move. Seconds later, I felt a bag of ice being applied to my cock. I screamed in pain, but couldn't free my hands to stop her. It took a few minutes, but then I was soft and back into my chastity cage.

The lock clicked, she left the room to hide the key, then we spooned until she fell asleep.

We get married in May!