When a Woman in a Dress, Walks into a Tranny Bar, the Conversation Gets Interesting

Again, I was stunned.

I carefully put the drawings away and set the table.

"What do you think," she said as she came down the stairs in t-shirt and sweats.

"I think you're lovely," I said, "and I love your nipples too."

"Not that, of the drawings silly."

"Ah, no shop talk," I said as she gave me a kiss.

"Okay, but what do you think?" she pressed.

"Caitlyn, seriously. You don't cease to amaze me." I kissed down onto her smiling lips.

Chinese food was the standard fare. Beef fried rice, egg foo young, chicken balls with sticky red sauce, eggs rolls and fortune cookies.

Caitlyn watched as I unpacked the food. I could see that she was being very polite, forcing a smile on her face.

"I'm sure it will be lovely," she said as I spilled the little packets of soy sauce onto the counter.

"Have you ever thought about getting tied-up and then having sex?" she asked as we sat down to eat.

Where did that come from?

"What, do you mean bondage?" I asked I'm sure with a little surprise in my voice.

"Kinda. I guess," she replied as she scooped up some rice.

"Well no," I said, "the idea of receiving, or inflicting pain seems ridiculous. Why, is there a dark side to you that I don't know about? Is this a Goth thing? I thought that was just fashion."

"It is just fashion," she answered and then reflected for a moment before continuing, "well for me anyway. No and it's not about pain. I'm just curious about, oh, I don't know..." She ate a mouthful of rice.

"Tying someone up and then forcing yourself on them?" She was being coy all of a sudden.

"No, no," she answered with a mouthful.

"Having someone tie you up," I said.

She looked up at me with a bit of a leer on her face. So that was it. She wants to be tied up. "And have what done to you?" I asked studying her reaction.

She swallowed, thought for a second or two then answered, "I guess that's the point isn't it? You don't have any choice." Her leer widened into a smirk.

So she was asking me to tie her up and do what? Fuck her? Feed her my cum? She already does that. She did say it's not about pain. I couldn't see myself whipping her.

"Is this about forced orgasms?" I asked.

Mock innocent look, "Maybe."

Okay. This could get interesting. "Let me get this right," I said, "you want me to tie you up, restrain you somehow, and then force you to have multiple orgasms. Is that it?"

"Maybe," she answered her eyes on the ceiling above.

So that's a yes, I realized.

I sat contemplating what she had just asked. Did she want to submit herself fully and completely to my innermost depredations? If I did that would I lose an employee out of the deal and would the country squire scare her off too? I'm male and by definition a sick fuck, like all other guys. Does she have any idea of what she's asking?

But then she's fucked up too. Nipple rings and pussy rings. Gee. And her cum eating fetish. What the hell else is there about this girl?

I needed to find out.

And I knew she wasn't going to just tell me.

Okay. One step at a time.

"Only if it does not involve anyone else," I said, "it's just you and me."

With a very calm voice and a sincere expression she said, "I'm cool with that. I wouldn't want it any other way. Just you and me. No third parties."

Did I just agree?

"You'll have to give me a day or two to sort myself out."

She was beaming.

After dinner we cleaned up, watched some TV then we went to bed. I fucked her silly again and of course she needed a little dessert afterwards.

"Caitlyn, can I ask you something?" I asked as we lay in bed afterwards.

"What?"

"Something serious."

"What?"

"Am I taking advantage of you?"

She pulled on my soft cock.

"Yes you are."

Fuck. Is she serious when she said that? Seriously, am I? She's a fantastic employee, a fantastic cook and housekeeper, and a sex maniac. The reality is...I don't deserve this girl.

"I don't mean to be taking ..."

"Doug, you duffus," she gave my cock a really tight squeeze, "if anything, I'm the one taking advantage of you!"

I winced in pain a little, "How so?"

"You're the eligible bachelor, you're the good looking guy, you've got the steady income," she squeezed my balls, then gently rolled them in her fingers, "you're the one with the big heart, you're the sweet kind gentleman, which I'm working on," she switched back to my cock, "and you're the one with the big stiff cock."

Only it wasn't stiff.

"Happy cock," I said.

"It certainly makes me happy!"

I kissed her. Her tongue practically gouged me.

We sat for a moment contemplating the ceiling.

"Doug?"

"Yes?"

"Do you think I'm taking advantage of you?" Her voice was very timid.

"Of course you are," I said, joking.

Wrong thing to say. She started sobbing.

"I'm joking!" How could anyone's emotions turn on a dime like that?

"No you aren't."

"Of course I am Cate, you're crazy. Actually that's not true. I'm crazy. About you!"

She let go of my cock and balls and gave me a big hug.

"I'm crazy about you too," she said.

I wiped the tears from her face with my fingers.

"Cate, you drive me nuts. My biggest fear is of losing you."

She squeezed me again and started crying again. After a few minutes of licking her tears from her cheeks, cuddling her and kissing her softly I slipped my hand onto the nipple ring of her right tit.

"Caitlyn, what do you want in life?"

"I don't know, what about you?"

"I don't know. I just want to be happy."

"Are you happy now?" she asked.

"With you, yes," I answered, "very happy."

"I'm more than just happy ," she said as she adjusted her position on the bed to give me a big, solid kiss. "I...I...lo..."

I kissed her suppressing the words she was trying to stammer out. I knew I loved her. I couldn't let her say the word. It was too early. I couldn't let her back herself into a corner, just to regret it later. If she said she loved me, I know how I would have reacted. I would have smothered her with affection. She was my employee. And my fuck-buddy. Had I heard her say, "I love you,' to me in a meaningful way, I would have broken apart. I would have been on my knees kissing her feet and asking her to marry me. To have my bambinos.

That would have surely scared her away.

I bit my tongue. Or rather I bit hers.

"Caitlyn, I am taking advantage of you. And I'm enjoying every minute of it."

She broke out into a huge grin and squeezed me tightly.

"And I'm taking advantage of you, and loving every minute of it too."

"You're so sweet," I said, "now turn off the lights and let's go to sleep."

She did. And in no time we were snoring.

*

The next morning, Friday, I had Caitlyn drive to Frank's to deliver the light fixture drawings. There was no sense in me going. That was her baby. I was proud of her. I could see she was a little apprehensive as she stepped into my pick-up truck.

"How did it go?" I asked when she returned.

"He wasn't there," she answered, "the secretary said he'd be back in an hour, but I didn't want to wait. Apparently his meeting with the client got moved to Sunday."

"That's okay, he's going to be blown away by the drawings."

She grinned at me.

*

The game plan for Caitlyn's coming out was dinner that night at Giovanni's Ristorante, a cozy overpriced little place in town. Caitlyn wanted to make a grand appearance to surprise me with the dress and all.

As arranged I dropped her off at her parents that afternoon together with her dress and everything she needed. She would take a cab and meet me there. Her Yaris was parked at the shop. Understood of course, but not spoken was that she would come back to my place and I would fuck her silly.

I didn't get to meet her parents, they weren't home when I dropped her off.

I picked up some lumber supplies and headed back to the shop to unload, shave, shower and get dressed. The reservation was for seven thirty. My intent was to get there a few minutes early.

I don't know where the time went, but I was running late. Not a lot, but just enough for me to be pissed off with myself.

There was a light drizzle as I sped along to the restaurant. I was trying to figure out how to ask Caitlyn to move in with me permanently. I hadn't even told her that I loved her. Nor had she told me. With any luck I could tell her that in the cozy restaurant and then ask her to move in with me. I wondered too if there would be a mental association formed, like a bond, between dressing femininely and being told 'I love you.' But then again, maybe she didn't really feel that way about me. Maybe she wasn't about to say 'I love you' last night. And of course there was the real possibility that I'd just be scaring a very good employee away. I knew I had to tread carefully.

There's never a great time to get a flat tire, but it only ever seems to happen at the worst possible moment. I got one. On the front passenger side.

I phoned Caitlyn to let her know I'd be late. She was already in the cab on the way to the restaurant.

It wasn't so much the dirt that I got covered in while I retrieved the spare from under the pick-up truck, or the dirt that I got on me as I pulled the flat off and hoisted the spare on. It was the constant spray and splashing from traffic on the road that completely covered me with oily dirt. I was too far from home to turn around.

I went straight to a Moore's shop, a chain menswear store. "Fix me up gentlemen, I'm already late for my date." They graciously let me use the staff washroom to wash myself as they selected clothing for me.

Within a few minutes and just within two hundred and fifty dollars, I was sporting a new set of slacks, nice shirt, socks and a sports jacket. They had the forethought of giving me a plastic carrier bag to sling over the driver's seat.

I was only an hour and twenty minutes late getting to Giovanni's.

Caitlyn looked lovely perched up at the bar waiting for me. The dress was a wrap around pinkish floral pattern with a plunging neckline. She wore a pearl necklace and pearl earrings. The nose ring was gone. She had light pink lipstick, eye make-up that wasn't just black. Her light pink leather shoes had a high heel to them and her clutch purse matched. Her legs were crossed as she smiled up to me. She looked delicious.

The only thing that ruined the whole picture was the stupid tattoo which stood out in strong contrast.

She toasted me with an empty martini glass. "Hi Doug."

"Caitlyn, you look lovely," I said, "I'm so sorry I'm late."

Before she even spoke another word, I could tell she had indulged in more than one martini. "You look handsome too," she slurred slightly.

Oh boy.

I stood her up onto her feet and gave her a nice kiss. The restaurant wasn't full. "I'm sure our table will be ready," I said.

The maitre-d showed us to our table. I held on to Caitlyn the whole way.

"Is it so bad," I asked as the waiter approached us with menus, "getting dressed like this?" The waiter was a middle aged man with a long nose and slicked back dark hair.

She smiled at me.

"Good evening," the waiter said as he handed us the menus, "may I get you something to drink from the bar?"

"Thank you," we said in unison, Caitlyn was about to say something when I added, "we may have something with dinner."

"Very well then, I'll give you a moment." The waiter whisked himself off.

"It's not so bad is it?" I asked again.

"Doug, let me put it this way. The next time you do something stupid, you're going to be the one wearing a dress and I'm taking you to a tranny bar," she said a little too loud. The people at the next table glared at us. Then, slurring, she added, "The hour and a half wait will be so much fun. I bet you won't have to buy a ffuckin' drink the whole night."

Oh dear.

"So Caitlyn, how many martinis did you have while waiting for me?" She held up one finger. Then a second. Then a third.

Oh boy.

"You should have seen the look on my mum and dad's ffaces as I came downstairs. They wouldn't let me leave until they took a photograph." She slurred the last word a bit.

"I'll bet they were shocked." I said lowering my voice, hoping that she'd get the hint.

"Ffuckin' right they were shocked. And I think they want to give you a medal." She didn't get the hint.

We were disturbing the people at the next table. I studied the menu. I needed to get some food into her right away.

The waiter came by with a little basket of different breads together with a plate of olive oil and balsamic vinegar. Thank you lord.

"Anything to start?" he asked. What's quick I thought.

"Would you like some soup Caitlyn?"

"No thanks."

"Can we just get a quick antipasta to share?" I asked the waiter.

"Certainly sir, antipasto for two," carefully correcting my pronunciation.

"With lots of ssseafood in it." Caitlyn interjected.

"Certainly madam," he smiled, "Are you ready to order, now or would you like a little more time?"

"I think we can order now," I said smiling to Caitlyn, hoping to get this whole thing moving along.

"I'll have the ffishhh," she said.

The waiter took it in stride with a sardonic smile, "We have fresh red snapper, fresh mackerel, tuna, swordfish, sardines and I believe codfish, which would madam prefer?" He glanced at me with an understanding look.

"I'll have red snnappper please, grilled."

"Ah, very well madam, with a little pasta and sautéed vegetable?"

"Yes, please."

"And for you sir?"

"Is there osso buco?" I asked.

"Yes, sir there is."

"I'll have that with potatoes and vegetables."

"Very good. And the wine?"

"Would you like a glass of water Caitlyn?" She glared at me.

"I'll have a glass of Pinot Grigio please," she said to the waiter but stared at me.

"I'll have a glass of red, whatever your house red is."

"Montepulciano d'Abruzzo" he said.

"Perfect." Off he went.

"Bread?" I held the basket out to Caitlyn. Thankfully she took a piece and dipped it.

I leaned in a little towards Caitlyn, hoping she would too.

"Are you trying to look down my top?" She leaned back pushing her chest out, then leaned forward pulling the front of her dress out with her pinky fingers, breadstick still in one hand. "Well here you go, have a look!" I heard cutlery drop at the next table. She sat back up.

"Caitlyn."

"They're still there."

"Caitlyn."

She bit into her breadstick again and smiled at me.

Was she doing this on purpose or was it just three martinis talking? Either way it had to end. I thought about when the power was out during the ice storm. That was the only time I'd ever seen her a little drunk. Then, she demanded that I eat her pussy and then whipped off her red t-shirt. Maybe alcohol affects her that way. If so, I was in trouble.

The waiter came by with two glasses of wine. Great.

Caitlyn took a sip then stuck her tongue out at me.

Oh boy.

I held the breadbasket out to her. She took another piece.

I felt her shoe on the inside of my leg. She smiled at me as she bit the bread.

Oh no.

"Stop that," I whispered.

"Something wrong?" she said with mock innocent eyes as her hand reached under the table and touched my knee. "You have something I want."

Oh no.

"Maybe I should have ordered ssausage? Big, sspicy Italian ssaussage." She said too loudly then giggled to herself. I held my forehead in my hand, elbow on the table.

The waiter brought the antipasto. Thank goodness maybe the food will keep her mouth busy.

She tucked into it with a relish. It certainly was good. Grilled shrimp still in their shells. Two types of grilled clams, sautéed squid. Cheese, black olives, green olives. Grilled red peppers and grilled green beans. It was all laid out with Italian parsley as a garnish.

The problem was that by the time we finished it, she had finished her glass of wine.

She wiped her fingers off on the white napkin. "Excuse me for a minute," she said, "I need to fsresshen up," she grinned at me. I stood up to help her up but she was up before I had a chance. Off she went with pink clutch purse in hand, a little wobbly on pink high heels. After three steps she stumbled, just a little, "Whoa!" but recovered her balance. She stood for a moment rocking on her pink high heels. Her feet were shoulder width apart and her arms extended to the sides horizontally, clutch purse in right hand. The whole restaurant watched intently.

I sat with my head down after she disappeared from sight.

Her trip back a few minutes later was somewhat less eventful. The waiter had just cleared the antipasto plate and side dishes away. He asked if the young lady would like another glass of wine. I said no.

"I'll have another glass of wine please," she said to the waiter as she approached the table.

She smiled at me as she sat down. Her light pink lipstick had been freshened up.

"Better now?" I asked.

"Yes," she said as she held out something pink and lacy, "these were killing me." She carefully laid out her panties on the white tablecloth, pressing all the folds out with her pink fingernails. I looked up to her. She had a massive smirk on her face.

Now she was taunting me. Rather than snatching them up in embarrassment I took a sip of my wine and laid my glass on the panties. Two can play this game.

I flipped the little size tag on the panties and whispered to Caitlyn, "Why they're just a medium, you said you have a fat ass."

"Fffuckk off."

The waiter did a double take but graciously set Caitlyn's wine glass down, not on the panties, without saying a word or batting an eye. The epitome of savior-faire. What a pro. He was definitely getting a good tip.

She gazed at me with those mock innocent eyes.

The waiter dropped the bill off to the table next to us. Thank goodness for that.

"Bald...hairless," she said trying to keep a straight face, "not even a tiny stubble."

"Is that a first for you?" I asked in a low voice.

"Yup," she said, sipping her wine while grinning at me.

"Let's have a quick peek then," I said. It was my turn to taunt.

"What here?" she gazed around, her expression had changed. The drunk twit actually took me seriously. She kept glancing around. Her expression turned to a wide smirk.

Oh no! She was going to do it! She placed her hands on the table and started standing-up.

"Noooo!" I yelled, pushing her shoulders down.

"You thought I would do it! Ah ha! ha!" Everyone in the restaurant was watching.

With my face in my palms I wondered if we were about to get kicked out of the restaurant.

The food came. Again, the waiter did not bat an eye as he lay the plates down but asked, "Are we celebrating something tonight?"

"No," I answered.

"Yes," she answered. We both looked to her. "The public humiliation of Caitlyn Progue," she slurred.

"And of Doug Jenner," I added quietly.

"Very well then, please enjoy your meal." He didn't bat an eye.

The food was excellent. Thankfully she enjoyed hers too. At least it kept her mouth busy. But not her foot. She kept that busy trying to play footsie with me while smiling.

The waiter came by to ask if everything was I fine.

"It's great," I said.

Caitlyn said the food was great and added with that mock innocent face, "But I don't think Dougie is having a good time."

I smiled at the waiter and said, "I'm having a wonderful time."

His sardonic smile said it all.

The waiter didn't even ask if we wanted dessert. The bill came moments after we finished our last mouthfuls. He certainly was a pro.

There were four martinis on the bill. At nine bucks each. I paid the bill and left a generous tip.

I retrieved Caitlyn's long black coat from the coat check. She flashed me her bare pussy before I could get the coat to her. No one else would have noticed.