My Life in a Tennis Skirt - Part 1

PART 2 | ALL STORY LIST 

I play tennis at a private club. I'm a pretty good player, but not great. I'm in a men's doubles league from 7:00 p.m. until 9:00 p.m. on Mondays.

After we're done, we sit around, talk, drink beer, and watch the next group play. We watch them play because they are all better players than our group.

And they are all girls. These are the best female players at the club. They're all in great shape, they all play a mean game of tennis, and almost all of them are really hot-looking.

There are a few ordinary ones or ones who seem a little 'butch', but most of them are really pretty. So imagine how I felt when I was done with my game and was walking off the court when Lisa, the cutest one of them all, asked me if I could play because they were one short tonight.

Well, first of all, I'd get a chance to play with these wonderful, beautiful women. And secondly, it would be great tennis, because they were all better than I was. So, of course, I said 'yes'. We played a great match, and it was a lot of fun.

At first, the guys watching us were making comments like, "Who's that ugly girl on court 3?" or "Hey, babe, you forgot your skirt" when I missed a shot. But it was all fun, and I really didn't even notice because I was concentrating on the game so much.

When we were done, Penny, who runs the league, asked for my phone number!

I hoped it was for something more than just to be on the'subs' list, but I didn't argue. Sure enough, I got a call next week on Monday, just before I left for the club.

"Lee? It's Penny," she said. "Hi there," I replied. Duh.

Not too smooth.

"Listen, Joanne has a sore knee and had to drop out at the last moment. Do you think you might be able to sub for us again tonight?"

"Sure thing!"

I said. And just as last week, I had a great time, played some great tennis with beautiful women, and only had to put up with a few taunts from the guys. Better yet, when we were done, the girls asked me to stay and have a drink with them, which I did, of course.

Whereas the guys drank beer, the girls brought bottles of wine, which I also happened to like. I had a great time. In three of the next four weeks, I ended up subbing again at the last minute. I had no problem with that; it was all great to me. But at the end of the week, I got another call from Penny. "Lee, we need to talk," she said.

"Sure, think. What can I do for you?"

I asked.

I was getting to know her now, and I felt a lot more comfortable talking to her.

"Well, we have two problems. First of all, do you remember when Joanne hurt her knee?"

"Yes," I said. Poor Joanne. She had been struggling to come back and was the weakest player on the court last week because of it.

"Well, she went in for surgery, and she is out for the rest of the season. We can't find another woman at the club with our skill level who can make it on Monday nights, so we took a vote and decided to offer you a chance to join us full time."

I didn't even have to think. I accepted right away. "Hold your horses there, Lee. Before you accept, you have to know that some of the girls said that they feel uncomfortable with a man in the league. They don't like playing with someone who might be looking at them as a sexual object, now a tennis player."

"But I'm not like that!" I protested. "I know that, and you know that. But some of the girls said if you join, then they would quit. So we'd be down 4 players instead of back even."

 "I don't want to cause trouble," I said. "If it's like that, I just won't play."

"That's sweet of you to say. I know that you're a caring person like that. So that's why I was able to convince the holdouts to give you a chance, under one condition."

"What's that?"

I asked. "They want you to do something overt to show that you are not after them sexually.

They want you to do something to show that you're in with us as a player instead."

 "And what is that?"

I asked.

"They want you to wear a skirt."

I was stunned. Wear a skirt. One of those little tennis skirts that shows off a woman's legs and makes her hips and her rear look so appealing?

Am I in one of those? No way.

"I don't think so," I started.

"Look, its not so bad. I know it might be hard for you to consider, so please do this for me. I have set up court time on Saturday morning, at 7 a.m., for just you and me. I checked, and the place is empty until 9.

We can go out and hit, with you wearing my skirt. If you don't like it after half an hour, we'll just call the whole thing off.

"What do you say?"

She asked me to do something for her as a favor how could I say anything but yes?

I showed up Saturday at 6:45 a.m., awaiting her appearance. She showed up at 6:52 and handed me a bag.

"Go into the locker room and put these on," she said, smiling at me. I went in and took off my shorts. In the bag was a white tennis skirt, in a large size, with an elastic waistband. It looked like it would fit me.

There was also a pair of silky white tennis pants. I had forgotten that the girls didn't have pockets in their skirts, so they had to wear special pants with side pockets to hold the tennis balls. I'd have to put on pants too.

I stepped out of my boxers and into the pants, which felt strange since there was no fly in the front. They were very soft and smooth. Next, I stepped into the skirt, which felt very strange and alien.

As I walked, I could feel it lightly swishing against me. It surrounded me in all directions and made me feel strange and uncomfortable. And for some reason, I got very hard. I had to wait a minute for my erection to subside before I walked out to see Penny. She was already on the court, stretching.

I joined her, pulled out my racquet, and we got started. The first strange thing I felt was reaching under my skirt to put a ball in the pocket of the panty. It felt so weird! As I moved and bounced around, I felt the skirt lightly touching me—again, a foreign sensation.

But there was one thing I had not expected: whereas shorts felt constraining, I felt somehow freer in the skirt. I felt like I could stretch out further, run better, and get to more balls. In fact, I don't think I ever played better tennis than I did that morning.

And do you know what?

After about twenty minutes, I didn't even really notice the skirt anymore. I just concentrated on the ball. When we were done, we had a juice together at the club bar.

We sat there and talked, and I guess I lost track of time because soon the place was filling up with people. I had to walk back to the men's locker room wearing a skirt. I got some strange looks, but I really didn't care.

 I was getting along well with the girl of my dreams, and I was about to join the most awesome tennis league in the club.

 When Monday finally arrived, I was nervous as I played in my league.

What would the guys say when I came back on the court with the girls wearing a skirt?

When we were done, I ran to the locker room, put on my pants and skirt, and then flew back on the court, hoping the guys wouldn't notice. It didn't take long before the catcalls started.

"Whooo!! Look at those sexy legs in that skirt!" yelled one guy. "Hey, babe, how 'bout a kiss for luck?" said another. "Don't listen to them," said Candy.

"They're just jealous."

"Yeah!" I said back to them.

"You're just jealous that it isn't you."

 They shut up because it was true. Just as on Saturday, I think I played better tennis in the skirt than I did in shorts. But I also learned a few things. My partner for the first set was Patty.

Her first serve went into the net, and I bent over to pick it up, just like I normally do. She walked up to me and whispered in my ear.

"Don't bend over from the waist like that," she said.

"Your pants show that way, and everyone stares at your butt."

I had seen many women use their racquets to pick up balls off the ground. I had thought they were just being lazy, but come to think of it, wearing a skirt would make you have to adjust how you do some things.

I hadn't thought of that before. From then on, I remembered to pick up balls with my racquet, just like the girls did.

And just like before, after playing for 30 minutes or so, I was concentrating so much on the game that I didn't even notice the skirt. I felt so free in it! I moved so much better without being constricted.

I almost raised the level of my game to that of the girls. When we were done, we sat around, drank a bottle of wine, and talked. How could I have a better day than that? There were 16 girls registered for the league, so with 4 on each court, that meant that there were 4 courts of doubles going on.

After a few weeks, I had played with and against all of the different women in the league. Some seemed OK with me being there, but some didn't like it. I could tell by the way they treated me.

One of the girls, Melody, didn't seem to like me at all. After we played, she went over to Penny and said something to her. Penny kept nodding but didn't seem to be happy with what she was hearing. I got a call from Penny a couple of days later.

She said that Melody had pointed out a club rule that I was in violation of. It stated that all players in the women's league were required to wear bras because some members had once complained about it being obscene for women not to be wearing one while on court.

Since I was playing in the league, I had to abide by the rules. She said that she was coming over, and we would talk about it more. I didn't like the sound of that. Me, wear a bra?

 No way! The doorbell rang, and I opened it. It was Penny, looking more lovely than ever with her long hair flowing.

When she played tennis, she pulled her hair tight around her into a small ponytail, which she wrapped around into a bun.

But in her street clothes, she wore them down, and it made her look even more enchanting than at the club.

When playing tennis, her short skirt showed off her long, smooth legs, but now, in a full-length skirt, she somehow looked even more sexy.

"Hey there," she said as she sauntered in.

"How are you today?"

I asked. "Would you like something to drink?"

"I'll take some juice if you have any," she said. I poured us glasses of cranberry juice, and we sat down on the couch.

She was carrying her purse and a shopping bag with her. She pulled out something from the bag a sports bra. I looked at her with wide eyes as she handed it to me.

"Don't worry, it won't bite," she said as I took it from her hands.

"You'll find that this type of bra is actually quite comfortable. A regular bra can kind of dig in during the day sometimes, particularly if you have big boobs like me, and the underwire can make you sore too after a long day. It has a racer back, and you don't have to do anything to close clasps on the back, so it is very easy to put on."

"All that sounds hard," I said, "about wearing a bra."

"Men who are so crazy about big boobs should try having them," she replied, "That would make them feel different about those poor girls at Hooters.

I felt the soft fabric of the bra's liner and tried to imagine having to wear it. I wasn't too sure.

"Go on, try it on!" I went into the bathroom, took my shirt off, and put the sports bra on. It felt so weird! I never wore a bra before, and having something wrapped around me like that with straps over the shoulder was just alien to me! I put my shirt back on and looked in the mirror. It was a black bra, and I had a white shirt on, so you could see it under my shirt.

I walked into the living room, feeling embarrassed. "There, it wasn't so bad," said Penny with a grin on her face. "Yes, but you can see it under my shirt."

"Then you need to wear a dark shirt so it doesn't show," she said. "You know I'm a traditionalist. All my tennis shirts are white."

 "That's why I also bought you this," she said, pulling a dark blue women's tennis shirt from the bag. It had a gray strip going at an angle but was otherwise dark. A bra would not show under the top. She handed it to me, and it seemed so small! There were no sleeves!

The neckline was cut low! I couldn't wear this thing! But she talked me into just trying it on. I went back again, took off my shirt, and put on the tennis shirt. It fit me tightly, but it was made of lycra, so it stretched.

I went back to see her, feeling strange.

"Hey, it looks good on you. Try it with your skirt!" she said, and I went to my bedroom to put on my skirt. I looked in the mirror and saw myself fully dressed in women's tennis clothes. I went out to the living room, and Penny made a big fuss about me.

"You look so cute! The girls are going to love it. Please promise me you'll wear it! Please!"

 "I don't know," I said.

"Well, how about we hit again on Saturday morning, so you can see how you feel about wearing it when you play?"

 I thought this over and agreed. We had a 'date' for Saturday. We talked for hours, and after a while, I didn't even notice that I was wearing women's clothes because I was so enchanted with her. Saturday came, and I was again nervous and shaky as I walked out of the men's locker room and onto the court.

But I found that, as with the skirt, the women's top was actually a benefit to my playing. Without sleeves rubbing on my arms, they flowed more freely, and I was actually able to hit the ball better!

We had some great rallies, and I realized that this was the best I had ever hit the ball in my life.

So I could not help but agree to wear it on Monday. Monday, walking out of the locker room, in front of all the guys, and onto the court with the girls, was the hardest thing I had to do in my life.

My first time in public was fully dressed like a girl, wearing a bra and everything. They really made fun of me, but Penny came to my aid.

"He lost a bet," she said, "and you're just jealous that you don't get to hang out with all the girls. Come on, Lee, let's ditch the guys and go hang out with the girls."

We walked on the court and they could do nothing but gape and drool as I went onto the court with all the beautiful women, who were all fussing over me.

Most of the guys couldn't get the time of day from the girls, but here they were all surrounding me, giving me attention, and treating me like I was a big deal. And when the guys watching me saw how good I was playing (better than any of them), it just added to their amazement.

"Hey, you play better in a skirt!" yelled out Mike, the league captain.

"You know what? I like this better. I quit. I'm not playing in your league anymore.

Now go on home. I have tennis to play."