Wrestling Contest

by Suejrz

 

Wrestling-Part two. Patti goes out on a double date.

The next day I was nervous with anticipation. Although I had been with Mike and Tom the previous day, it was a casual, chance meeting. Tonight would be a lot different. Tonight would be a dinner date with a guy I hardly knew while my wife was doing the same thing with an old high school friend of hers. By late afternoon, Judy showed me the two outfits she choose for us to wear that evening... Both dresses were neutral, summery colors with spaghetti straps. With our summer sandals we would each look like the picture of femininity. She hung them up for me to iron while she went to take her bath and begin getting ready for our big night. So while she was soaking, I stood at the ironing board and carefully pressed our dresses. I had difficulty believing that I would really be wearing this very sexy, summer dress in a few short hours. I wasn't crazy about Judy wearing her dress either but I was much more worried about me wearing mine. Somehow I finished my chore and rejoined Judy in our old room as she was seated at her vanity.

"Judy, I finished ironing our dresses. My dress is so short and revealing. I will never be able to get away with wearing that all night. I really don't think I can go through with this tonight. I just can't go out on a date with Mike wearing that outfit. I will never be able to act as a woman all night." Practically in tears I begged Judy one last time. "Please, just let me stay home tonight. Please!"

"Patti, you know I can't do that. First of all you will look stunning in your dress and so will I. Secondly, both guys will be here and they're expecting two girls, not one. If you don't go it will ruin everything. And if you ruin my evening I promise you I will ruin a lot more than just your evening. Believe me, I will tell them everything if I have to. And I'm sure you can act as a woman all night especially since you'll be in quite a pickle if you don't. I have to start getting ready and I suggest you do the same if you know what is good for you. Your nails are a mess and need to be polished too."

"So I returned to my room to begin my preparations for my date, my first date as a woman. I took a hot bath, shaved my legs and underarms and polished my nails before donning my robe and returning to my bedroom. Like Judy I sat down at my dressing table and began my transformation. I applied my makeup carefully, more carefully than ever before because I knew I had to look my best this evening. Every step was done with extreme care from applying my foundation to outlining my eyes and lips. I took extra pains with my hair making sure every strand was perfectly situated before I sprayed it lightly to hold it in place. With my hair and makeup completed, it was time to begin dressing. I stepped into my thong panties and hooked my matching bra in place. After removing my robe I opened a new pair of sheer tan pantyhose and slipped them up my smooth legs. Standing there in my lingerie with my hair and makeup done, I looked like any other women dressing for a night out on the town. But looks can be deceiving since I was certainly not any woman. No. A mere few weeks ago I was a regular guy and now I found myself completely made up as a woman getting dressed for a date. I sprayed some perfume on my legs, arms and hair before removing my dress from the hanger. I gingerly stepped into it, pulled it up and zipped up the back. I slipped on my open toed sandals and then stood back to look at my image in the mirror. The image that appeared was decidedly feminine. From head to toe, the image was demure, soft and womanly. Although my image was feminine I still had to deal with my inner, masculine feelings because despite my reflection, I still knew who or what I really was. My legs may be sheathed in nylons, my feet encased in high heels and my body wrapped in a pretty summer dress but inside I was still a man. I would have to keep all those traits hidden all evening unless I wanted my secret exposed.

I gave myself one final glance in the mirror, checking my hair and makeup. Grabbing my purse, I went downstairs to see how Judy was doing. She smiled when I walked into the room. As I entered she looked me over carefully from head to toe. "Wow, you look really nice in that dress. It fits you perfectly. I see you did your nails too. You even gave yourself a pedicure. You look very nice, very sweet and feminine. Perfect."

It was only then that I realized how beautiful Judy looked. It was a long time since I've seen her really dressed up. She was generally pretty casual but not tonight. Her dress was a more provocative than mine. It was a bit more fitted, cut lower in the bosom, and definitely shorter. And like me, she was made up beautifully. She certainly looked like she was going out on a very important date.

"Thanks. You look very nice too. In fact, I wish you were wearing something a little more conservative."

"Not a chance. I haven't had a date in years so why would I dress conservatively. I want to have fun tonight and you should too. After all, we're just two girl cousins out for a good time, right Patti?"

"I'm not too sure of that. We may be acting like we're two girl cousins but we know the truth. I mean not too many married couples go out on double dates with two men! I can't believe you are making me do this. It wasn't enough to have me running around as your maid, now I have to go out on dates with you. You know this isn't easy for me to do."

"I'm not too sure about that. You certainly make it look easy. You look more feminine than most of my girlfriends. You've been dressing as a woman for almost two weeks now and you look and act the part very well. Face it. You're a girl. And just remember that this evening. I don't want any problems tonight. I told you that tonight we are two girl cousins having a good time. And we will have a good time if you know what is good for you."

Our conversation was cut short by the ringing of the doorbell. I felt a twinge in my stomach as Judy went to answer the door and greet our two male companions. "Hi guys, you're right on time. Patti, Tom and Mike are here. Its time to go."

Time to go? I wanted to go and hide. I wanted the floor to swallow me up right then and there but I simply smiled and joined Judy at the door. After the guys complimented us both on how nice we looked, we were off to the restaurant for dinner. Tom was driving so Mike and I were relegated to the back seat. This was the first time I ever had to get in the back seat of a two-door car while wearing a short summer dress and high heels. It was a lot more difficult than I ever imagined. I somehow managed to situate myself but not before giving Mike a good look at my smoothly shaven thighs. I could feel my face blushing as I smoothed my skirt under me and tried to regain my composure. Mike's smile didn't make me feel any better knowing that he enjoyed the show and probably thought I was just being flirtatious with him.

The drive to the restaurant was uneventful although I was extremely nervous trying to carry on a conversation mainly with Mike since Judy and Tom were talking about their high school days. Once we arrived and parked I had to treat Mike to another even more revealing leg show since I could feel my dress ride up as I slid across the seat to the open door. Even worse Mike held my hand and helped me extract myself from the confines of the backseat giving him a clear view up my skirt. Even Judy gave me a little smile as she watched me struggling to modestly pull my dress back in place.

Surprisingly, dinner was fine. Actually it was almost enjoyable especially after a glass of wine. As I sipped my wine with dinner I was able to relax a little but still remained fairly quiet. I figured the less I talked the safer I would be in my role. I breathed a big sigh of relief when the guys paid the check and I assumed we were on our way home. My relief, however, was short lived. Little did I know that we were going into the lounge for an after dinner drink. Before we went into the lounge, Judy wanted to use the ladies room.

As soon as we were in the ladies room, Judy glared at me. "Are you purposely trying to ruin my evening or are you just stupid?"

"No. Why are you saying that?" I questioned.

"Why? You haven't said more than a dozen words all night. You practically ignored Mike all during dinner. I'm so worried about you two that I'm ignoring Tom. I warned you that I wanted to have fun tonight and you're ruining it. And let me tell you, if it continues I'm going to ruin your night big time. So you better use all your little charms on Mike when we get back there. I want you talking to him, dancing with him and just to make sure you feel like a woman, kissing him. If not, I'm spilling the beans."

Judy, you can't tell them about me. Please don't do that. I'd die." After finishing using the facilities, I rejoined her at the vanity to check my makeup.

"So, what's it going to be? Are you going to make sure Mike enjoys the rest of his evening or will we all have a good laugh at your plight? The choice is all yours but if I were you, I'd do my best to show Mike I'm interested in him." Judy reapplied her lipstick and then sprayed some perfume in her hair. Turning to me, she asked if I wanted to use it too. "I would. It may help heighten Mike's interest in you."

Knowing I could not risk being exposed I nodded my assent and Judy sprayed me liberally with her perfume. "Ok Patti, let's go. It's show time."

As I walked across the room I was suddenly aware of my vulnerable position. The sway of my dress, the clicking of my heels and the aroma of my perfume all made me very aware of my feminine appearance. I would need all of this and more to keep my secret from being unmasked. Somehow I would have to not only be feminine, but enticing. Mike would not only have to think of me as a woman but a woman to whom he is attracted to; a woman he would want to dance with and kiss. For me this was unexplored territory. Before tonight I have never really been out with a man, never have danced with a man and certainly never kissed a man, except my father when I was a child. And I knew Judy request wasn't for me to have a father son type kiss with Mike. And if I didn't' do this, I risked total emasculation with Judy telling them both the horrible truth. So I was left with two horrendous choices. Either, be exposed as a man to both Tom and Mike or to be found to be a desirable woman by Mike.

While neither choice was desirable, I knew being exposed would ruin me. I couldn't deal with those two guys discovering I was really not a woman especially after spending so much time with them already. Mike may even react violently since his manhood was impugned. My only choice was to become even more feminine and sexy to keep my secret safe. I smiled at Mike as I slid next to him at the table. My conversation was more animated than before as I tried to show him I was interested. I was also drinking a bit more to help calm my nerves and give me the courage I needed.

When a slow song played, I told Mike it was one of my favorites. Fortunately, he took the cue and asked me if I'd like to dance. I quickly agreed. He held my hand as we made our way to the dance floor and I realized I never danced as a woman before. My right hand met his left and he slipped his right hand around my waist. I've always enjoyed dancing so I just closed my eyes and followed his lead. Surprisingly, I felt more at ease then than I did all evening. I wasn't sure if it was the music, the alcohol or Mike's strong arms but I felt relaxed. So relaxed that I actually rested my head on his shoulder as we swayed to the soft music. When the song ended, I sexily told Mike that I enjoyed the dance very much as I gazed into his eyes. Deep down inside me I was so embarrassed trying to act sexy with some man but I knew it worked as he looked deeply into my eyes and began to move his lips towards mine. He gently kissed me. As I responded to his kiss, he kissed me more deeply. "I enjoyed it too, Patti. I enjoyed both the dance as well as the kiss.

"

As we made our way back to the table, I wondered if I made the right choice. Each decision I made recently was taking me further and further into femininity. Perhaps it would have been better to let Judy tell them the truth so I could regain my male status. Sure it would have been embarrassing for the moment but it would have ended this charade. Instead, I now had to endure the discomfort of knowing that I just let a man kiss me right in front of my wife. I had to deal with his inevitable advances since he now thought I was interested in him. I had to continue to play the demure, feminine woman as my wife did the exact same thing. So many emotions were raging through me at the same time, fear, jealousy, and worry.

As we rejoined Tom and Judy at the table, Judy smiled at me and said, "Looks like you two are getting along very nicely. How sweet." At that point I knew she saw Mike kiss me on the dance floor. So I also knew my secret was safe.

Knowing that, the rest of the night was pretty calm, at least as calm as possible. Perhaps the drinks had an impact on me as well. All four of us danced a few fast numbers and then we each danced one slow number. Fast dancing was better but it still felt strange to be out on the dance floor dancing in open toed high heels and a sexy dress. But even with those clothes I still had to keep reminding myself that I too was a girl that night. Actually wearing high heels and pantyhose was the best reminder of the role I was playing, but despite the heels and the hosiery, inside I still felt somewhat like a man. It was a strange, strange sensation. I was caught between two very different worlds and those two worlds were surrounding me. And they were about to collide

After another round of drinks we decided to call it a night and we all piled back into the car. I practically fell into the back seat and started laughing as I realized my dress was almost up to my waist. Mike was getting quite a show and I'm sure he was thinking that he would like to slip his hand up my dress but I knew that could not and would not happen. He'd likely kill me if he discovered my secret hidden safely in my thong. My laughter soon turned to reality as I felt his one arm behind my back and his other hand resting above my nylon clad knee. During the drive home, Mike pulled me over to him on one or two occasions and kissed me tenderly. As our lips met again and again, I felt strangely excited. I always enjoyed kissing but I never kissed a man before. My excitement was tempered by the knowledge that my wife was sitting very close to Tom in the front seat. I had the feeling that Tom had his hand on my wife's leg but I couldn't be sure. I was very sure, however, that they kissed at one traffic light. Their long kiss was only stopped by the sound of a horn honking after the light changed to green.

As we parked into front of our house Tom got out of his seat to hold the door open for Mike and I to exit. Judy told me she'd be in shortly so Mike walked me to the front door.

I thanked him for a lovely evening and prepared myself for the inevitable good night kiss which by now was nothing new. Mike took me in his arms and kissed me tenderly. As we parted, he told me he would call me.

Once inside the house I breathed a sigh of relief. I could finally let down my guard and relax. I sat down on a chair in the foyer to await Judy. After a few minutes I heard her and Tom on the front porch and I was positive he kissed her goodnight too. Then the door opened and Judy came in as well.

"Wow. That was some night. I can't believe we pulled that off." She said with a sigh.

"What do you mean we pulled that off? I think I was the one on the spot all night. You're used to being a girl. I'm not. And knowing that, you didn't make things any easier. I can't believe you made me dance with Mike and kiss him too. You don't know how awkward that was. I hated it although you sure seemed to enjoy your kiss. I can't believe you let Tom kiss you right in front of me like that. I'm surprised that you didn't let him pull off your dress too. And I know he had his hand on your leg too. Didn't he?"

"So what if he did? It's my leg, not yours. And yes he kissed me but not as much as Mike was kissing you. I only asked you to kiss him as a test. I never thought you would do that. But you surprised me again. And then did you just kiss him once? Not you. You practically made out with him the entire night so don't you lecture me, Missy. If anyone should be upset it's me. But this entire episode really proves what I suspected all along. You're a natural at this. I mean how many husbands could have done what you did tonight? Not too many. I mean some guys may look ok in a dress but you looked and acted good enough to fool two men all night long. Some men may know how to mimic some feminine actions, but you were able to sit, talk, eat, dance and kiss a man all without a hitch. And most men would never be able to sit quietly and watch another man seduce his wife but not you. You just sat quietly making out with your date so don't you dare lecture me about anything I did. And yes he did touch my legs and you know what? I liked it. So, you just better remember your current role as the maid in this household. You're the maid now. You're no longer the jealous husband and I'm still the boss. Do you understand me, Patti?"

"Yes. I remember my role. It's kind of hard not too considering all I've been through."

"I'm going to bed. Starting tomorrow things are going back to normal so make sure you are properly dressed in your uniform. And don't make too much noise. I may sleep in a little late. You can have my coffee ready around nine or so though. Good night."

Sleep was difficult that night. I had a lot to mull over: my dating adventure, my kiss, my wife's dating adventure and kiss, my continuing role as a servant and everything else running through my head. I awoke the next morning and after dressing and getting made up, I picked up my dress and lingerie from last night and picked up Judy's as well. I did some laundry and then made some coffee and fresh juice for Judy. She arose around 9:30 and joined me in the kitchen. "Good morning, Patti. You can pour me a cup of coffee. I left a few outfits on the bed that I need you to iron. I'm having lunch with Tom today and I'm not sure which outfit I want to wear so you'll have to iron both of them. Oh, and when I'm gone I want you to give my bedroom and bath a thorough cleaning. Fresh sheets, spreads, the new curtains and bath set. I need a change."

She needs a change. What a joke that is. I'm the one who needs a change. I'm running around as her maid and she needs a change. She's having a lunch date and she needs a change. I'll be cleaning and scrubbing her room and bath and she needs a change. I wanted to scream and rebel but I couldn't. I wanted to tell her she couldn't have lunch with Tom but I couldn't' so I just said, "Yes, madam." I finished cleaning the kitchen and most of the laundry then decided I better iron her clothes for her lunch date. She selected two summer outfits, two skirts and two summer tops. One skirt was short and one was long. While I enjoyed ironing most of the time, I felt extremely emasculated today as I stood ironing her clothing. I mean ironing is one thing but how many husbands iron a skirt and top for their wife to wear out on an afternoon date? Not too many!

By the time I finished with her clothes, Judy was finishing her shower and starting to get ready for her luncheon date with Tom. It was like a repeat of last night's preparation. Much time was devoted to her hair, her makeup, her body lotions, her scent and finally her outfit. And while she was doing all of this I was on my hands and knees scrubbing her bathroom tile and floor. When I came out to get the mop, she was finished dressing. As I expected, she selected the short mini skirt with the light beige shell top. Summer sandals and her tan legs completed her sensational look. And her perfume filled the entire room with a sexy scent. She looked refreshed, pretty and alive. I felt sweaty, tired and drained.

"So, how do I look?" She said as she stood in front of her full-length mirror.

"You look very nice. That outfit is most becoming on you.

"I agree. Tom seemed to like my legs last night so I figured I give him a little more of a good thing. Can't hurt plus it's warm today so this will be cooler. I left the new bed linens and curtains on my chair so you can put them on after you finished cleaning, dusting and vacuuming. Is that clear, Patti?"

She just had to get that one dig in about her legs but what could I say? Nothing at all.

"Yes. Your rooms will be done to your satisfaction when you return."

"I'm sure they will, Patti. I'm leaving now so you should have plenty of time. I don't think you'll need to prepare dinner tonight. A light salad will be fine for me." With that, she turned and left the room. I stood silently as I watched her sashay across the room.

I found it difficult that day to concentrate on my chores. Everywhere I turned that day I was surrounded by her things. Her nightgown was on the bed, her makeup on her vanity, her clothes strewn about the room all were reminders. And all the while, I knew she was out with another man enjoying herself. I could see her holding his hand, laughing at his silly jokes and kissing him romantically. I could not believe she did this to me again. Last night was bad enough but at least I was there to see what was going on. That wasn't easy but today proved much more difficult. Not knowing what was going on was much worse than knowing. And as each hour passed my imagination became more involved. I just knew they were having sex in the park or that they rented a room or that he seduced her in his car. I could feel his hands touching her legs and removing her panties as she eagerly awaited his excited shaft entering her. And I knew he was very well endowed. She looked lustfully at his engorged organ, dying for it to penetrate her and bring her to fulfillment. And when she was sated, she would take him in her mouth, kissing his shaft and sucking on his manhood until his mighty orgasm filled her with his love potion.

These were the thoughts filling my head as I turned my attention to Judy's bedroom. Somehow, dusting and changing linens didn't seem that important but I knew I had to finish or I would be severely disciplined upon Judy's return. The two rooms took me hours to clean and prepare and I didn't finish the final touches until nearly 5 pm. I even lost track of the time and was surprised that Judy's luncheon was nearly four hours long. Finally, about 5:15 I heard her car pull into the garage.

When she entered the house, she didn't really even greet me. I was met with a question. "Did you finish your chores as I expected?"

"Yes, I just finished your bedroom and bath. I'll make your salad now."

"That won't be necessary but you can make me a cup of tea and draw my bath. I need to unwind. I am exhausted from my day. Patti, put some scented oil in my bath too I want to feel fresh."

 

I realized then that she would not provide me with any details of her day. And I knew if I asked she wouldn't tell me. So, I simply said, "Yes, madam." I ran her bath and then prepared her tea, which I brought upstairs. I knocked on her door before entering since she made it clear to me that I was to always respect her privacy now. She told me to come in and bring her tea into her bathroom. I sat it down next to the lighted candle as she dismissed me "Patti, please take my soiled things downstairs to be laundered."

 

I turned and picked up her skirt, top, bra and panties and went to place them in the hamper. I couldn't help but notice the stain on the crouch of her panties and wonder if she really did have sex with Tom or if she was just excited to be with him. Even though either choice wasn't that great, I hoped it was the latter.

During the next few days, things went slowly back to normal. Judy spent a bit more time on the phone. I assumed it was with Tom but I wasn't sure. She also was talking a lot to her sister Anne. Anne and her husband Harold lived in a very exclusive section of Connecticut. Harold owned his own consulting company and was very successful and very rich. He was also very annoying and snobbish.

I was pleased that Mike called me once too but he said he would be away on business for the next few weeks. In a way that was a relief. I had enough things to worry about without planning to go on another date. However, my worry load was about to increase when Judy spoke to me the following morning.

"Patti. I have both good news and bad news for you. The good news is we'll be getting away for a few weeks vacation. Well, I'll be vacationing. The bad news is you'll be working for most of the time. I was talking to Anne and she told me Maria their maid had a family emergency and had to go back home for a few weeks. It couldn't have happened at a worse time for poor Anne and Harold. It seems Harold has a few parties scheduled at their house for some of his key clients and they really depended on Maria. So, you will be Maria's replacement until she returns."

"What? Please tell me you're joking. You know I can't stand Harold and now you expect me to go there and replace their maid. I can't have Harold see me like this. I will never live it down. Never." I could feel my eyes welling up with tears as I pleaded with Judy not to make me go.

"Oh stop your crying. Everything is all arranged. Remember servants have no say in these matters. Besides my sister needs us, and she's always been nice to you. So, consider this our way of saying thank you for her generosity in the past."

"Anne's fine." I cried. "But Harold is such a superior person. He's always looked down on me and now you're going to make me go there dressed like a woman to be a maid. I will never live this down. You're horrible!"

"Patti, one more outburst like that and I'll be calling Mike and a few other of your friends and coworkers to introduce them to Patti. So who do you want to know about you? Do you want Harold or Mike to know? Since Anne knows already, I think you know the right answer."

She was right. Although I hated the thought, it would be easier to have Harold and Anne see me. They lived a few hours away and we certainly didn't travel in the same class. Reluctantly, I agreed to Judy's plan but in reality I had no choice.

"Good. We're leaving tomorrow so you'll need to pack our things tonight. We'll need to bring at least enough clothing for three weeks. You can get our suitcases and bring them upstairs. And make sure you pack all your uniforms. I'm not sure if Maria's uniforms will fit you." Later that afternoon, I realized just how much I had to pack. There was lingerie, shoes, uniforms, nightgowns, robes, slippers, cosmetics, wigs and other paraphernalia. I needed two large suitcases for each of us.

  

  

  

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