A Strange Convention

Part 1

The hotel bar was not very busy. I'd just finished a round of golf and in need of a frosty beverage. I was pleased there were a few spots at the bar available. I immediately noticed a number of lovely ladies all around at tables and sitting near me at the bar. They were clinging together, as women usually do in the bar atmosphere. Most of the tables in the bar were full of them. Big hair and big dresses. Most of the ladies were of middle age, which was fine with me. A few looked to be in their 20s or 30s, but most were older. It must be a fashion show or a fancy, important party, I thought.  Three were tightly knit together at my right, talking and laughing. At my left were two more, also involved in their own conversation.  I am not an idiot. I don't live in a vacuum. I started to get the vibe here. The more I looked, the more I realized a lot of these ladies aren't ladies. Or at least, some of them weren't. I've dabbled on the internet with all sorts of fun and kinky things. I've seen plenty of transition videos including that cute little gal who got everyone at Bud Light in all that trouble. I think she is pretty cute, actually. I've certainly crossed into some strange areas like crossdresser and trans sites. Noone is bothering me. Everyone seems to be having a good time. I suppose I've never actually seen a trans lady for real before, in the flesh. I'm going to enjoy my beer just the same.  I ordered a tall one, leaned back and enjoyed it. I was in my own little world. Finally cooling off after a 5-hour round in the 90-degree sun. It was REAL nice. 

As I was ordering my next one, the bartender informed me it had been taken care of. This was the first time I realized I was the only guy in the bar. The three ladies at my right had stopped chatting and were looking down the bar at me. But none were indicating it was them. I turned to my left where the two ladies had stopped their conversation and were also looking my way. The one closest to me was smiling and glancing to her left, back at the girl behind her. And there she was. 

Janet was 35 or 40. Well, she was at least a little younger than me. I fell in love in love immediately with her bright green eyes and her big, friendly smile. Her hair was long, curly and bright red, like an innocent Irish lass. She was dressed in a fluffy green prom sort of dress. She was nervously running her fingers up and down the stem of her wine glass. White wine. Her expression was one of shy, hopeful excitement. She pointed to her friends position next to me and quietly whispered "Can I sit there?" I smiled and nodded. 

Things began to really sink in when the lady next to me stood up to change seats with Janet. I'm pretty tall, 6 foot 4, but in heels this lady was all of that. They quicky switched seats with Janet scooting her bar stool a bit closer to mine as she smoothly slipped onto it. She was sweet and polite. In a soft, quiet tone, she introduced herself. "Hello, I'm Janet."

"Hello, I'm Bill. What's a nice girl like you doing in a place like this?" I think I'm witty. 

"Well, I am a nice girl, most of the time. The real question is, what are YOU doing HERE today?"

"HA! Good question. I just finished golfing and needed a cold one. The shuttle drops you off here, and my car is in valet. So, here I am. "

"Oh. I'm sorry. I thought... Well, I thought you might be here because of the convention."

"I see. I was wondering. Are you all here together for something special?"

"Just a yearly get together. It's my first time. I live in Seattle and drove over yesterday with my friends. I'll be here till Monday. So, two more nights. But you didn't come here for that, did you?'

The look of disappointment was all over her face. I could tell she saw something in me she liked very much. It must have been difficult for her to reach out to me. A total stranger in a strange city. But she thought I might be there to meet some nice trans girls. But I hadn't. It was sinking in. I was just sitting there looking back at her with a blank face. 

"I'll let you finish your beer then. It was nice meeting you, Bill." Janet turned back to her friend, continuing the conversation they had been having before making her brave move. I noticed the ladies to my right turn away as well. Back in their world. I overheard one of them say "Ahhh... that's too bad." I felt like a heel. I suddenly felt alone. 

She had been so nice, polite and vulnerable. And what a pretty face! She smelled nice, too. The bustle of the dress was toughing my arm. It felt nice. Feminine. I sort of forgot she wasn't a real girl. But she sure acted like one. I suppose it's here attitude, the life inside her, that made me feel like she was a lady. I classy, sexy lady. And she likes me. "What the hell?" I thought.

I've been married and divorced 3 times. I've never done anything bad to the women in my life. But I never did anything good either, I suppose. I just went through the motions. Flirting, fucking, marriage, boring sex, boring life, divorce. And so on. Never much passion. Or respect, either way. If this lady wants to buy me a drink, I'll let her in. What could happen?

Janet was startled when I touched her shoulder. She jumped a little bit. She had been involved in a pretty intense conversation it seemed. But when she looked over her shoulder at me, it was obvious she had been crying a little bit. Did I do that? Fuck! She swallowed and attempted to regain her composure. "Did I upset you? I'm so sorry!"

"Not you, my friend. I've just had a few bad times and I was hoping this weekend would cheer me up. Getting away for a few days and hanging with my like-minded friends. But as I'm sure you know, It doesn't matter where you go, there you are."

"Well, I wanted to thank you again for the beer. And I was hoping you'd let me get you another glass of wine in return. I've got some time today and I can't think of a better way to spend it than right here."

Janet blushed. It was sweet. "Of fucking course you can buy me another wine. Actually, can we make it a martini?" She winced like she suddenly realized she shouldn't have said that, like that. 

"Ha. Sure, we can make it one for each of us." I summoned the bartender and soon we were on our third. 

Janet works for Microsoft and now it's almost all from home. Some sort of fancy programming manager. She has an apartment overlooking Pike Place Market and the sound. She confessed that she wasn't actually in any sort of transition. Some of her friends weren't either. They just enjoy dressing up and having fun with it. But she pointed out a few of the ladies who were serous and going through the process to womanhood. "I don't do any hormones and haven't had any enhancements or surgeries." I confessed I thought she was very feminine and pretty anyway. I told her I liked her perfume. I was trying to be nice and supportive. She liked that. 

"I might need to Uber home. I'm fine now, but I don't think this will be my last one."

"I've got a room." Her shy and nervous expression returned. "You don't have to do... anything. I'm just offering. As a friend."

"Well, as a friend, let's get two more of these for the road and check it out. I've never stayed here. The room must be nice?"

She leaned back in surprise. Had her patience paid off? Am I going to join her in her quiet, private room for the rest of the afternoon? And maybe all night? She smiled. "Sir, two more please!"

Most of the ladies at the bar were gone. But a couple of them who were still there made some sort of comment as we walked out together, spilling out drinks as we stumbled out. But I didn't care.

One martini went all the way over in the elevator. Crashing and plashing all around our feet. We stumbled and fell closer to each other. I put one arm around her waist with the other trying to find the 12th floor button. I realized she was about 2 inches shorter than me in her 4-inch heels. They were now dripping with vodka and vermouth. The glass had not shattered, luckily. But now my attention moved. Her face was right in my face. She looked at me, deep in my eyes, carefully sipping the remaining martini. She put the rim of the glass to my lips while she was licking hers. I finished the drink. My hand moved from the back of her waist up to the middle of her back, pulling her in. The soft silky fabric felt nice. I noticed the outlines of a corset or a longline bra under her dress. My dick twinged. Who doesn't love some sexy lingerie? Then in I went. 

Her kisses were warm, wet and very passionate. She sighed several times like this was something she had been dreaming of her whole life. Her lips tasted like peaches. My fingers were wrapped around hers still holding the now empty martini glass. She was gently sucking my tongue deeper into her mouth. But then, suddenly and abruptly, the bell rang, and the elevator door rumbled open. 

A couple of people were waiting in front of the door. They looked away in embarrassment. I whisked Janet out, quickly passing the people. One of them called out to us. "Have fun!"

Embarrassed and out of vodka, the realization of what I was doing was sinking in. The room key was being difficult. This was my chance to politely thank her for the drinks and the kiss and go. But I just stood there, holding her purse like the husband. Inside the room with the door locked she quickly disappeared into the bathroom. "I've gotta pee. Sorry!"

This left me in the beautiful room alone for a few minutes. "Wow!"

"Yeah, I know!" I hear through the bathroom door. "Make us more martinis. The bar is open!" Then I hear the shower running. I look back to the beautiful, opulent room. The bar is not your typical hotel mini bar. There aren't any little bottles of anything. There is a fully stocked liquor cabinet and 2 dozen beers and any mixer you'd ever want in the cooler. I find a couple martini glasses and fill them from the vodka in the freezer. Very classy!

There's floor to ceiling glass in front of an elevated king size bed covered in fancy pillows and throws. But the view takes your attention and your breath away. We are perched on the 12th floor overlooking the second largest lake in the state. This was no entry lever room in this hotel. There was a full bar and a living room with a see-through fireplace in the wall between the living and bedroom. There was an office area in the other room. This place is amazing. 

The sky was blue but beginning to turn pink and orange as the sun slowly drifted over the tree covered mountains. The lake was changing colors with the sky. I was mesmerized. I've never seen the lake from this perspective. I gaze at the beauty, sipping my ice-cold martini. This is nice. 

From behind me, she touches my arm. It's a good thing the room was so amazing. It's a good thing there was much more hooch in the bar. I didn't have time to think about what might be happening next. Looking over my shoulder I smile. She is in sexy lingerie and nearly nothing else. Over the black and purple corset and girdle is a long sheer robe tied tightly with a black sash around her waist. The corset and girdle are very fancy, like vintage lingerie I've always admired. The corset has large cups full of something that could be real boobs, or not. But it didn't matter. They look great on her. The tight sexy purple girdle with garters is long and of the open bottom sort. 5 or 6 garter straps on each leg are seductively holding up her black, lace top stockings. I look her up and down like an inspection. Her smooth hand feels nice on my bare skin. "I should shower too."

"Please don't. I'm not waiting for another kiss. I can't wait."

I turn toward her and again we embrace. But this time there won't be any elevator doors or curious people interrupting us or catching us at play. It's all or nothing now. I'm not even close to knowing what will happen. All I know is her kisses are wonderful. I love it. So does she. I can tell. Her hands are running up and down my chest. My shirt is lifted up over my head. I feel her fumbling with my belt and unbuttoning my shorts. They drop to the floor. "Bill, I'm going to do my best to make you happy. After that, the rest is up to me."

Humm?

There is a sinister look in her eyes. "Get on the fucking bed, Billy boy."

She leans in. I fall back sitting on the beautiful bedding with her on top of me. She quickly slides down between my legs, spreading them. Her head is in my lap. She sucks my cock up into her mouth with a sigh and a moan of pleasure. She is sucking so hard it almost hurts. She is loving my cock very much. I am loving this too! My head falls back as I get close. I gaze at the widows and the amazing lake view. I catch a glimpse of us in a wall mirror. Such a beautiful sexy lingerie clad woman performing the perfect act of love and affection. I'm in heaven!

You know once a guy gets all riled up and ready, a good BJ gets him off pretty quickly. And I'm no exception! She gripped and squeezed and stroked and sucked and tongued and did it all so well! 

Part 2

I laid there for what seemed like an hour. She was in pajamas, drinking and working on her laptop. When I came out of my daze, she asked if I'd like to be HER bitch. I looked at her with a silly look on my face, I'm sure. She tipped her drink at me and asked again. "Will you be my bitch, Bill?"

I'm a polite sort of guy. But I didn't know what that means. I don't want to seem stupid. Everything else seems pretty good so far. "I guess you could show me."

"Good. I appreciate that. There is a collar on the table. Put it on." She wasn't asking. This feels weird. Well, it all feels weird. Sitting up on the side of the bed I slowly buckled the heavy black leather dog collar around my neck. 

"Tell me, how does that feel?"

"I'm not sure how I'm supposed to feel. I guess I feel... stupid."

"Good. Then it's working. Put the cuffs on and we will get started. "

Next to the bed were two leather wrist restraints. I looked back at her questioning the motive. She was standing up by the desk with her pajama top half open. Underneath was a sexy white lace bra. She hadn't just changed out of the lingerie into pajamas, but her underwear was new too.  She was opening it wider and rubbing and squeezing the boobs in the large round, D cup bra cups. I still haven't played with those, I thought. 

The cuffs were not all that simple to put on. But I finally managed. 

"Now, tell me, Bill. How do those make you feel?"

I was wondering if this was some sort of psychological inquiry. "They make me feel... (I didn't have to think too much. I knew how they made me feel.) I feel like your bitch."

"Exactly. You take direction well, Billy Boy. Get on the floor, on your knees, baby."

What the fuck? I slowly slipped down off the bed onto the soft white carpet. My stomach was turning in nervous waves. Once I was on my knees, she quickly stepped up to me taking my wrists by the cuffs and locked them together with a paddle lock. She held my hands up under my chin and used another paddle lock to attach my wrists to a link on the front of the collar. 

"Now, that is much better."

Kneeling in front of me, she began to kiss my face, neck and lips. Things are getting back to normal, I thought. The pajama top opened. She pulled my face between her soft, full breasts. The bra was very lacey and smelled like perfume. She rubbed my face between them. I started to kiss and lick the bra. A finger skipped one cup aside exposing a large, warm sweet breast.

"I lied. I did have one enhancement. Do you like them?"

Her big perky pink nipple slipped into my mouth. "Suck really hard, baby. I love that."

I worked the tits with my sucking mouth until her bra was off her shoulders and both of her full breasts were glistening wet. Her huge pink nipples were hard and erect. I was hard all over again, too. She took a moment, reaching down to check on my excitement. "I'm glad you still like me, baby."

Another item joined in. She took a strap sort of thing and wrapped it around my cock and balls. It was really tight! "Ouch!"

"Oh, good, I want it to hurt a little bit. But don't worry. It's all part of your training."

I stopped licking a nipple. She was staring down at me. I was starting to get nervous again. I wiggled against the cuffs and the collar. They aren't going anywhere. "Training?"

"It's OK, baby. I'll be gentle. Get on the bed."

She pulled at my arm, lifting me back to the bed. I was struggling not being able to use my hands or my arms to balance or support myself. I fell on my side on the soft, silky sheets. She sat me up with my legs hanging over the side of the bed. Another set of cuffs were buckled around my ankles and locked together. "Be a good boy and do what I tell you. Okay?"

I nervously nodded.

She moved back a bit posing in front of me. Her long, tall body was quite impressive. Her breasts were pretty spectacular too! She moved slowly side to side, carefully removing her bra. Now she was naked from the waist up. Beautiful, I thought. "You're beautiful!"

She blushed and smiled at me. With that, her pajama bottoms dropped to the floor. Under was a full white lace garter belt with straps holding up white lace top stockings. Very sexy. But the lingerie was just a side note, of course. her long fat cock was hard to ignore. As a matter of fact, I barely noticed the garter and stockings. Her cock was nearly fully erect, the tip glistening in the dim overhead lights. I just sat there, petrified. I couldn't move. I knew this was part of the deal, but holy shit. I've never seen one angry, pointing at me. My mouth was dry. I couldn't speak. What do you say?

She seemed pleased I didn't completely freak out. She slowly walked up to me, rubbing her fat cock against my chest. It was just under my cuffed hands. "Take it in your hands, baby. You'll like touching it"

Looking up into her beautiful eyes I still couldn't make the connection that she wasn't a girl. But this cock? She slipped it between my hands and helped me wrap my fingers around it. It was twinging and pulsing. I've never touched another cock before. I felt like this was an appropriate response to her being so nice and blowing me earlier. She was moving closer and up to be sure she had it in the right position for me to stroke it. I gently squeezed it.

"The tip is waiting for your kiss, baby."

There was cum leaking out. Some was already dripping halfway down the shaft. I opened and tasted it. I sucked the tip a little bit. Her hands were on my head rubbing her fingers through my hair.  I loved the taste of her cum already. I wanted her to blow a load for me. I sucked harder and squeezed a little bit more too. The whole moment was very seductive and romantic. 

"Tell me you love me, baby."

I was following all of her leads. I answered then went back to tasting her sweet cock. "Yes, I love you, Janet."

"Tell me you want to be my bitch, baby."

Now I know what she means. Things have switched around a little bit. Well, a lot, actually!

"Yes Janet, I want to be your bitch."

It seemed add to say it, but it seemed right, too. I just kept answering her requests and sucking her fine, fat cock. I was in heaven. 

Bill