Games We Play Ch. 02

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If you read my first Games we Play Story you know how I like to play a crossdressing game with my wife. It starts with me sending her an e-mail telling her what I want to wear and do the following Saturday. For the week leading up to Saturday she orders me to perform a variety of outdoor activities while wearing women’s clothes. If I perform every activity she requests dressed appropriately with pictures as proof then I’m rewarded with an entire weekend of crossdressing. Of course I also get to enjoy the entire week of dressing up while I perform the activities.


The game has rules like if during the week I don’t perform any of the activities my wife orders me to the game ends. My wife’s not into my crossdressing but tolerates it so her incentive is to order me to perform activities that I’ll be too embarrassed to do so the game ends. However, the rules limit what she can order me to do so the activities only give me a chance of being seen. After all it would be unfair if she could just order me to go grocery shopping in lingerie to end the game.

I guess I lose all control of my senses when I’m horny but after last month’s game I didn’t think I’d ever be horny enough to want to play again. But here I am one month later willingly playing the game. Of course I’m hornier than hell because my wife ensured it.

A month ago I was kneeling alongside a highway off ramp dressed in a bra, garterbelt, stockings and high heels in front of two men and my wife and the only way home was to give the men blowjobs! I know it was my own fault for telling my wife my deepest darkest fantasies but she didn’t have to make them come true.

I’m straight and never had sex with a man before that day.

Only after I’d sucked off both men and swallowed every drop of their cum did my wife let me in the car and drive me home. But before she did, she had me put my panties back on then handcuffed my hands behind my back and when I got in the car she put the seatbelt on me. It wasn’t to make sure I was safe or we didn’t get a ticket from the Highway Patrol. It was to make sure I was very visible sitting in the front seat just wearing lingerie with no way to cover up or hide.

Needless to say she drove slowly on the freeway so trucks would pass us. Since she drove in the middle lane the trucks passing on the right had a perfect view to me. Only a couple of trucks passed us without slowing but the rest slowed and enjoyed the view of me – a lingerie clad slut. Little did they know I was a man or I’m sure their reaction would have been much different!

When we got home my wife helped me out of the car and into the house where she told me to stand in the living room and wait for her. I didn’t have much choice since she hadn’t removed the handcuffs. She went into our wine cellar and got herself a bottle of Chardonnay then poured herself a glass. I could really have used a glass myself to wash the lingering taste of cum out of my mouth but she didn’t offer me any and I wasn’t about to ask for some.

She sat down still fully dressed and looked at my lingerie clad body, took a sip of her wine and smiled. Then she said “I was only making you do what you had begged for numerous times in the past. And based on the hard-on you had most of today I’m guessing you enjoyed being exposed, having strangers dominate you and giving your first blowjob. So tell me, did you?”

I had to be honest “Parts of today turned me on immensely but other times I was totally embarrassed and humiliated. And I don’t think I ever want to give a blowjob again.”

She drank some more wine then said “You know today was the first time I ever truly enjoyed your crossdressing. I never realized just how submissive you are when you’re dressed up. You’ve always want me to dominate you and order you to do things you wouldn’t normally do. But until today I had no idea you’d do absolutely anything I told you to no matter how humiliating it was for you. Guess what? It turned me on! I got so horny when those two men started dominating you. And then when you sucked them off I almost came without even touching myself.”

She continued “Now that I know this, going forward I’m going to enjoy your crossdressing as much as you. Every month we will play your game but from now on I’m going to truly push your limits and there won’t be a safe word for you to use. You will do anything and everything I tell you to no matter what. My goal is to have an orgasm without touching myself but just by watching you do things all the nasty kinky things I can think of to embarrass and humiliate you.”

“Public activities that don’t just give you a chance to be seen but guarantee you’ll be seen by lots of men while you’re dressed in very feminine outfits. I’m guessing having you dressed as a schoolgirl and dropping you off at a shopping mall for an hour or two might attract some men’s attention. But what if I order you to dress like a hooker and abandon you at a Home Depot parking lot around 10 AM on a Saturday morning and don’t güvenilir bahis return to pick you up till noon? Or better yet, I drive you to one of the gay areas of San Francisco early one evening and order you out of the car only wearing lingerie. Don’t worry I’d pick you up sometime the next day. How does that sound slut?”

I couldn’t help it. My wife was pushing all my right fantasy buttons and I was getting horny again. My cock was getting hard inside my panties and the bulge was obvious. Unfortunately for me it’s the ultimate lie detector test and my wife knows it.

I said “The thought turns me on a little but I’m not sure I’m up for it.”

She replied “Well that bulge in your panties tells me this turns you on so going forward your crossdressing is going to be about me trying to have an orgasm at your expense. Do you understand?”

I knew at this point my wife had finally accepted my crossdressing but it was going to be on her terms. I had told her in the past I was submissive when crossdressed and I had this need to be humiliated but I don’t think she ever truly understood. Now she did and I could only think of the saying “Be careful of what you ask for.” All I could say was “Yes Mistress.”

“Very good slut. From now on when I order you to perform an outside activity no matter how many people will see you all dressed as a woman you will not hesitate. And if I tell you to suck a cock, you will get on your knees and do it immediately and swallow every drop of cum. Trust me; you will be doing plenty of both for my enjoyment!”

What can I say? I was dressed in lingerie and in a very submissive mood and everything my wife said she was going to make me do turned me on. At this point I didn’t want to wait a month I wanted her to start right now!

FYI — I’m normally a very masculine guy that has a dominant personality. Not one of my friends or co-workers would ever believe I like to crossdress and am a sub. Also, I have no desire to crossdress and live as a sub fulltime. It’s just about once a month I get this urge and it won’t go away till I’ve dressed up in women’s clothes and gone out in public. And it’s not to be seen but just to have the adrenaline rush of possibly being caught.

A few times in the past I have been caught in public dressed en fem by men. Either they were cool and actually engaged me in a conversation asking why I was dressed the way I was or they laughed their heads off at me which was very humiliating.

I actually got turned on when guys caught me and talked to me. I would force myself to stand there in my very sexy outfit while I answered all their questions. What’s more embarrassing to admit is how much more I got turned on when I was caught and the guys would laugh and make rude comments to me.

I guess I have to admit I am a submissive crossdressing slut. But 99% of the time it’s the fantasy that gets me off not the reality. And now it looks like my wife is going to turn my fantasies into reality. I’m scared but turned on at the same time. Yes, the types of things my wife has promised she’s going to make me do are things I’ve fantasized about but never actually thought I would do.

“So what game do you want to play next month?” asked my wife bringing me back to now.

Normally I have weeks to think about it but without time to think I just blurted out “I want you to take me to a mall and drive me around the parking lot giving a few people a chance to see me as we pass them.”

“OK, that sounds like a fun game. Come here so I can remove your handcuffs. Then you can get me another glass of wine and let me give it some thought on how I can make this game memorable for you.” She said with a smile.

I went and got her more wine then returned and handed her the glass. She looked my lingerie clad body up and down and said “Take off your panties then stand five feet in front of me with your feet shoulder width apart and your hands clasped behind your back.”

I took off my panties and stood as she had directed. My wife has seen me naked a thousand times before but now standing in front of her in this position while she was fully clothed sipping wine and looking me up and down made me feel more exposed than ever.

After what seemed like an eternity she finally spoke “You look a little pale. You know, like you need to get out in the sun. For your next game I think I’m going to have you wear white lingerie and I’d like you tan to make the white color really stand out.”

I wondered how this is going to happen since it’s not summer and it’s too cold to lay out and try to get a tan. I shouldn’t have bothered wondering as my wife had the answer.

“For the next four weeks till the game begins you will go to a tanning salon twice a week to get a tan. However, to tell if the tanning beds really work I want to see some tan lines. So you’re going to wear a women’s two piece bikini and I have just the one for you to wear. Remember the leopard print bikini you bought me a few years ago with türkçe bahis the tanga bottoms and full coverage top? That should give you some very sexy tan lines. What do you think?”

“I think it will give me feminine tan lines but will prevent me from doing some things I have planned. So I really don’t think that I should wear it.” I stated hoping to get out of doing it.

“What do you have planned?” she asked

“Well Dan and I are planning on playing racquetball every week starting this Wednesday and how can I change clothes in the locker room? Plus, I have my routine semi-annual doctor’s appointment coming up in three weeks.”

My wife replied “Well if that’s all you’re concerned about, you will wear the bikini to the tanning salon. I know a way that no one in the gym will pay any attention to your tan lines and as for the doctor’s semi-annual visit; they never make you take your clothes off. No worries.”

Now I was worried.

My wife’s expression turned serious. “Challenging my directions is exactly the same as not immediately complying with anything I order so you need to be punished.”

“Each time you go to the tanning salon you will wear the bikini underneath your women’s jean shorts and women’s blue polo shirt vs. putting it on once you get there. If no one looks too close when you arrive or leave they won’t notice the pink stitching on the shorts and know they’re women’s shorts. But I wonder if they’ll be able to see outline of the bikini top under your shirt?”

After letting that sink in for a minute she continued “Don’t ever challenge my directions again or next time your punishment will be much worse. But that’s what you want isn’t it slut? You want me to punish you with much more obvious and humiliating outfits and activities. Don’t you slut? You don’t have the balls to do the things that turn you on, but if I order you to do them, you have no choice and you’ll do willingly do absolutely anything won’t you?”

“The more I push your buttons the more turned on you get. And the more turned on you get the more receptive you are to doing anything and everything I tell you to as long as it exposes you to people in women’s clothes and humiliates you. Isn’t that true slut?”

My wife was now staring at my lie detector and it was hard as a rock. No wonder she had me remove my panties and stand with my legs apart. She wanted to judge my real reaction by hard my cock got.

I sheepishly said “Yes, the fantasy turns me on but the reality is not always as much of a turn-on. In fact it’s down right humiliating at times.”

She laughed at me and replied “Once upon a time I might have believed that. But hell, you even got hard sucking a cock today!”

I really hate my cock sometimes! If only it would get hard just when I wanted it to not give away what I’m feeling.

I replied “Yes, I get hard when you order me about but I have no explanation for getting hard while I gave a blowjob.”

“Well since your hard cock admits you want me to punish you, how can I deny you? Let’s make getting a tan more humiliating. Instead of your women’s blue polo shirt you are now going to wear your women’s white polo shirt with the very feminine pink emblem on the front. I wonder if it’s sheer enough the leopard print bikini top will show through.”

“And you are going to stuff the bikini top with some padding to make it more obvious. In fact each time you go to the tanning salon you will add another layer of padding to the bikini top so by the third week your tits should be sticking way out and obvious to everyone.”

“During the fourth week I’m going to have you replace the padding with your old C-cup breastforms. I don’t even know if crossing your arms over your chest will be able to hide these.”

“And just so you can fantasize about your punishment if you don’t go to the tanning salon twice a week in your bikini with more padding every time, I will glue your 40DD breastforms on your chest before you put on your bikini top and then I’ll drop you off at the tanning salon in just your bikini. No top, no jean shorts, just a 2 piece bikini with your DD breastforms and high heels.”

My cock was sticking straight up and my wife said “I can tell you really like that idea.”

No I didn’t! My fantasizing cock did but there was no way I could ever be seen dressed that way.

My wife continued “And since you seem so eager to start on your tan, go put on your bikini, shorts, top and sandals and let’s go to the tanning salon now.”

I wondered when my wife’s bikini became mine. I went into our bedroom to change clothes. I dug out my wife’s bikini from her dresser drawer (yes, I know which drawers hold her lingerie and other clothing I might want to try on when she’s not home) then I got out my women’s shorts with the pink stitching and white polo shirt.

I put on my wife’s bikini bottoms after I tucked my hard-on back between my legs otherwise it would have stuck out the top. The bottoms were not very big and when I looked güvenilir bahis siteleri at my ass in the mirror I saw the tanga cut left half my ass exposed. These tanga cut bikini bottoms were going to give me a very feminine tan line that I couldn’t explain if anyone ever saw it. A tan line from a thong bottom would have been a lot easier to explain.

Next I put on the bikini top which tied in the back and behind my neck. I added some padding as instructed and again looked in the mirror. It hit me like a ton of bricks! I no longer cared about trying to explain tanga tan lines on my ass. How the hell could I ever explain the bikini tan lines on my chest if anyone ever saw them?

I put on my women’s jean shorts and white polo shirt. I was almost afraid to look in the mirror. As well as the shorts being skin tight, they were low rise and only had a 3 inch inseam. If a woman was wearing them I know she’d look hot — but not me. The top was made of a material with some stretch to it so of course my wife had me get it one size smaller than I normally wear when I bought it.

Needless to say it was form fitting and even with minimal padding it looked like I had small A-cup tits. It also wasn’t quite long enough to reach the top of my shorts. There was about a one inch gap of skin showing that definitely made the outfit look feminine. If I looked close I could see the leopard skin pattern through the top. I sure hoped no one else got to look that close. I put on my sandals and left the room to join my wife.

She made me drive to the tanning salon so she could reach between my legs and rub my still hard cock and under my top to play with my sensitive nipples. I was totally turned on by the time we got to the salon. Before we exited the car she told me I was not allowed to cross my arms in front on my chest and hide my little titties.

We entered the salon and there were a few patrons waiting. My wife told me to follow her to the counter so she could inquire about setting up tanning sessions for me. The saleslady behind the counter offered to allow me to prepay and set up guaranteed times so basically all I’d need to do was walk into the salon and to my reserved tanning booth.

My wife thought for a minute then said “No, he’ll be coming at random times and you can’t tie up a booth because he might be there. If the booths are all full he can just sit in your waiting area takes till one is free. And he might as well pay as he goes.”

My wife turned and smiled at me. We’ve been married long enough she didn’t need to explain her thought process. Her goal was to make me go in and interact with the saleslady each time with my ever increasing bust size. She’s also hoping each time I go to the salon the booths will be full so I’ll have to sit in the waiting area embarrassing the hell out myself by the way I’m dressed.

While my wife and I were standing there I couldn’t help but wonder if the saleslady behind the counter could tell I was wearing a bikini top or if the patrons behind me in the waiting area could identify the lump under my shirt as the knot of a string bikini. I was both humiliated and turned-on at the same time.

I eventually got into a tanning booth where I stripped down to my bikini and laid down in the tanning bed. I laid there waiting for the timer to go off and could only think about the tan lines I was getting.

I didn’t dare take off the bikini before getting in the tanning bed and get an overall tan for fear of the punishments my wife would heap on me. I couldn’t imagine what they would be but I knew for sure they would be much worse than what kinky thing she had planned for exposing my tan lines in a month.

Eventually the timer went off and the tanning bed shut down. I put back on my women’s shorts and top then met my wife in the lobby and we went home.

When we got home she told me to strip naked and stand in front of her so she could see my cock’s reaction while she told me a couple of the ground rules for the month. First thing she told me was I to keep my body totally shaved the entire time with the exception of my feminine landing stripe of pubic hair and my head. The landing stripe was to be narrower than my bikini bottoms so when I was naked there would be my tan line and then a small strip of white skin on either side of my pubic hair and my pubes were to be kept exactly a quarter inch in length.

I could picture how feminine this would look and how humiliated I’d be if anyone saw it. I couldn’t control my little head’s reaction and my wife smiled as I got hard.

Then she handed me a bottle of bright red nail polish and told me I was to paint my toenails. She told me three coats of polish should do it to begin with and I better fix any chip immediately as she’d be checking every night.

I knew my wife was going to make me show them off at some point just to humiliate me and I got harder still!

On Tuesday I was to meet Dan right after work to play racquetball. I wouldn’t consider Dan a close friend but he’d been over the house few times and my wife liked him. Dan was single and would flirt a little with my wife and had the body of a gym rat. There was an obvious physical attraction between the two but that was all.

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