Submitting to a Gurl

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Young man experiments with sex, submission, and a gurl.
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I ran the last block to the bar on the corner of 12th and Locust. Arriving seconds after the clouds opened up and the rain came pouring down. Quickly ducking into the doorway, I was in the downpour less than ten seconds, but that didn't stop me from becoming drenched through. My clothes stuck to me like a second skin. Thick strands of my rain soaked hair were blocking my vision and dripping into my eyes. I could feel the little droplets running down over my face. I wiped my eyes clear of the water and looked around.

A little out of breath from the dash I made down the last half of the block, I took a second to catch my breath. I'd reached my destination of the "X Barr", but not before the storm got the best of me. I tried to pull at what a few minutes ago was a crisp white shirt, but it was hopeless. I laughed at the thought of having taken at least an hour to dress and get ready to go out. What a waste. Shaking my head in despair of any chance to improve my appearance, I ducked inside to escape the rest of the downpour.

The rain pelted against the stained glass windows and the sliding doors at the front of the building. I looked around. It was the first time I'd ever been in this place. I've walked by it thousands of times, always thinking of it as another neighborhood bar. It wasn't until it came up on my google search that I discovered it was primarily a gay bar. Not that I was surprised, the neighborhood is considered the rainbow section of Philly.

Looking around, it looked like a nice place, clean, neat and well kept. I liked the look and feel of it and that put me at ease. I also liked the old world, colonial architecture,the exposed brick, and the huge wooden bar with brass accents. It had a comfortable, friendly atmosphere that helped to calm my jitters.

I had never done anything like this and I was nervous. I still couldn't believe I had googled this place, let alone actually come here. I typed in a number of different terms before Google helped me to find what I was looking for...this bar happened to come up on the search and I liked the web site best.

Of course, I googled it from my friend Jen's computer and then deleted it from her history. I don't know why I felt the need to delete it. Her searches include everything from aberrant sexual behavior to zoophilia. As a doctoral student in PENN's sexual psychology tract, she has read or heard things that most of us don't even know exist.

When I told Jen about some of the things I've been thinking about recently, she didn't even blink. My little fantasies didn't shock her a bit. In fact, she ended up helping me come to some level of acceptance with my fantasies. According to her, curiosity and sexual experimentation was normal. Though, I'm not sure everyone I know would agree. Still, I didn't tell her everything.

I wanted to protect my privacy. I didn't want anyone to know what I was planning. Besides, there's no easy way to explain why you are googling, "Places to meet crossdressers in Philadelphia." And, if there is, I'm not aware of it. Not to mention, I wasn't prepared to be met with a dozen questions about it, not even from my best friend.

Jen and I talk about almost everything in our lives. She's the only person who knows even the smallest of details about my secret fantasies. She's been the only one I've felt comfortable enough to talk with about my dreams. Jen's the sister I never had growing up. Still, I wanted to keep most of this to myself for now.

Keeping things from her made me feel a little dishonest and maybe ungrateful since she's always been so helpful, but for now, it's what I needed to do. Jen's always been a great friend and has encouraged me to examine my feelings and talk about them.

At least, Jen calls it encouraging, sometimes it borders on interrogation. But, I know she does it with love and that makes it a little more palatable. On occasion, she even gives me suggestions on how to explore and deal with them. I suppose I'm lucky that she's in her final year of her doctorate studies in psychology. A few more months and I'll have to call her Dr. Jen, lay on a couch, and pay a high price for 50 minutes of her time and her words of wisdom.

"Need a towel, handsome?" A voice broke through all of the random thoughts that were running through my head.

"Yeah, thanks," I said, and reached for the towel.

"Let me do it." Her voice was soft, but her words were direct and a little demanding.

"Ahh, okay, thanks," I said and tried to clear the rest of the rain from blurring my vision. She took my glasses off and gently wiped my forehead and dabbed the towel softly over my eyes. Then she did the same over my cheeks and the rest of my face.

Standing there, I felt like a little boy being cared for by his mommy. Who did this? What kind of person wiped the face of a stranger in a bar in downtown Philadelphia? I asked myself. But at the same time, I realized I liked her touch. I enjoyed being cared for, if only for a minute. And, it had been way too long since anyone cared for me.

She held my glasses up and then began to clean them off too. I thought she was going to hand them to me, but instead, she stepped a little closer and placed them perfectly on my face. She didn't get them caught in the thick curls of my hair or poke me in the ear. With perfect precision, she placed them on my face.

I felt myself feeling a little uncomfortable. Not because it was such an odd gesture, but because I really liked it. It was unusual for me to be affected like this, but it was more unusual to have someone do a kind and generous act for me. It didn't hurt that it was all being carried out by a very attractive woman.

It all seemed odd to me, considering my reason for being here in the first place. Had I met this woman a few weeks ago, maybe things would be different. Tonight, I had a different purpose in coming here. And meeting a pretty lady wasn't it, well, not exactly. I was here for a totally different experience, but I also knew I wasn't immune to the female touch. In fact, I greatly enjoy the feminine side...of all people...men and women.

She smiled at me and asked, "How's that?"

"Great, thanks," I said, and now that I could see clearly, I couldn't help but take in her attractiveness.

She was tall. In fact, we were close to the same height. I'd guess without those heels on, she stood about five feet, nine inches tall. Now, I was almost looking eye to eye with her. I admire a woman who can walk gracefully in high heels and not kill herself. I think it's a special talent some women have. I know I'd fall and break something if I had to wear them.

This tall, beautiful blonde stood there and continued to smile at me. Tilting her head from one side to the other, she examined me more closely. Then she winked at me.

"I thought you'd be taller," she said.

I shook my head and adjusted my glasses, even though they were in perfect position to see her clearly.

"I'm sorry, have we met?" I asked.

"You are David, aren't you?" she questioned.

"Yes, and you?" I tried to figure out where I knew her from. The closer I looked, the more familiar she became, but I couldn't place her.

"Picture me with brown hair," she said.

Again I looked at her. Tall, blonde, pretty green eyes. Full lips that were made for kissing and other fun things. Still, I couldn't place her.

"I'm sorry. You look really familiar, but..." I hesitated. Holy shit! Are you kidding me?

Her full lips turned up in a smile and she winked at me again. "By George, I think he's got it," she teased and tapped my nose with the tip of her finger as she smiled at me.

"Ann Marie?" I questioned, totally unsure.

This time, I looked her over from head to toe. She was really an extremely pretty woman. I don't think anyone would think twice about that fact. Her hair was medium length and blonde. I had only seen her as a brunette when we video chatted a few times. Her eyes were bright, beautiful, and they smiled with her when she smiled. I would have never guessed her secret.

She stood almost six feet tall in those heels of hers, but she didn't shy away from her height at all. She stood proud and strong. You were able to see she worked out because she was so tight and fit looking. She carried her frame straight, had great posture, and long, lean muscles.

I couldn't help but stare at her bust. Everything looked perfect to me.

"Just Annie. Please, call me Annie." She took my hand and started to lead me to one of the side tables. "I wasn't sure if you knew or not," she said. "But feel free to continue to take inventory if you like. I don't mind."

"I didn't. I'm sorry. I should have...but you're..." I didn't know how to fill in the rest of that sentence without sounding like a total ass.

"You didn't what? Why are you sorry? And you should have, what?" she asked in a somewhat teasing, somewhat serious tone. "Oh yes, and the most important one, I'm what?" she asked. "Please, don't stop there. I definitely want to know what the rest of that sentence holds."

She sat across from me and stared directly into my eyes. These weren't rhetorical questions she was asking me. She wanted answers. I wanted to crawl under the table.

Instead, I took a deep breath and calmed myself. I closed my eyes for a second and tried to center my thoughts. I wanted to get rid of my nervous energy before it overwhelmed me. I wanted to meet her. It was my idea to meet in real life. The website wasn't enough anymore. I wanted to get to know her beyond the internet.

"I'm sorry if I sound like an idiot," I said and totally meant it. "I didn't recognize you. You look different blonde." I explained and hoped it was an acceptable answer. "I should have known you and I'm sorry I didn't. I hope I didn't offend you." I said apologetically. "And, I don't want to sound like a complete ass, but I want to be honest with you. What I was going to say was...you're not what I expected."

She laughed and it echoed through a mostly empty bar. We were now sitting at the table and she reached over and took my hand. For one second, I was unsure of what to do. Hold it, the voice in my head yelled at me. What's wrong with you? This is why you're here. You came to meet her. Don't fuck it up.

I held her hand and she brushed her thumb over the top of my hand as we sat and started to chat. The waiter came over and took our drink order. Annie ordered an appetizer for us to share.

"Matty, would you bring us the Hummus platter, please?" she asked.

"Sure, Annie. Give me five," he said like they were old friends.

"You must come here often," I said.

"I guess you could say I'm a regular," she said. "It's comfortable and I feel safe here."

"Safe?" I asked. Then realized how stupid I was.

"Yes, safe. It's not easy to find a bar where you're accepted and safe as a crossdresser. Most of the designated gay bars are great, but this is less crowded and CD friendly. Not every man who comes here is gay. In fact, many come here for the same reason you did. When a man checks me out here, I know exactly why he's looking." She smirked, "And it's not because I'm a curiosity to him. It's because he see me for who I am and he's attracted to me." She had the most serene look on her face as she said it.

It struck a chord for me, in me. I wanted to feel that way just once in my life. I was tired of always having to play part of a role to fit into my environment. At home with my family. At work with my colleagues. Even when I was out with friends. I wanted that feeling of serenity she had on her face. I wanted to be accepted for who I really am.

"No one here cares which bathroom I use." She laughed, but it was not a humorous or happy laugh. It was more of a laugh that has been practiced to cover up true feelings. I know that laugh. I've used it most of my life.

A few minutes later, we had our drinks and our hummus platter.

"David," she said. "I know you might be uncomfortable for a while. But I want you to know, even when you're unsure of what to say, just be honest with me. That's all I ask. Just be honest with me. Okay?"

"Okay," I said. "So, being an ass is okay, as long as, I'm an honest ass."

She laughed again. This time it was a real, happy, belly laugh. "Yes, an honest ass is okay."

"You're very pretty in person," I said, "especially when you laugh from your heart."

"Thanks," she said and then questioned me. "What do you mean especially when I laugh from my heart. What other kind of laugh is there?"

"The one you used earlier," I answered. "The one you use when you are covering up something hurtful or painful, but you don't want to show it to others."

"You sound like you know that laugh." She looked in my eyes a little deeper. Her head tilted and I knew she was watching me very closely to see if I'd lie. I promised to be honest and I was a man of my word.

"I do know it. I know it all too well," I said. I knew she wouldn't let me off the hook that easy.

"And..." she said. "You don't think I'm going to let it go at that, do you?"

"I was kind of hoping," I said and popped a cucumber slice full of hummus in my mouth.

"No chance, handsome. Give it up."

"Umm..hmm...can't...mouth full," I said and smiled back at her.

"I'll wait. We have all night."

She had that determined look on her face. I recognized it from some of our chats online. Like the last one when she asked if I was sure we should meet. I got the impression she'd been hurt before and was trying to avoid it from happening again.

"Damn," I mumbled as I finished chewing and took a drink of my beer. "I was hoping that wasn't going to be your answer."

"You may have been hoping, but you knew my answer."

"I did," I said. "Okay, here it is. I do know that laugh. I've used it to hide behind on more than one occasion. When I lived at home and my dad would say something derogatory about something he saw on TV or heard on the news and I'd use that laugh to cover my feelings. I shivered when he used the word, 'faggot,' when I was a kid. I never really understood why. I just knew I didn't like it. But that laugh was my only response. I couldn't say anything. I just laughed."

"Me too," she said. "I felt the same way. I used to say it was a generational thing, but sadly, hatred and bigotry transcends generations. It's not limited to an age or an era. It's simply narrow mindedness and lack of compassion."

"It's that and more," I said. "I see it all the time and I don't stand up against it. I can be at work and hear a snide comment and I don't defend the person who it's made against. I don't say, shut the fuck up. I just pretend to go along or to not hear it. So, I'm responsible too," I said.

"Yes, I'm not giving you a free pass, but it's different. I've done it too. It's more a protective mechanism than anything else though. It's not initiating hate. I'm not sure what it is, but I have an understanding of it."

"Any chance we can lighten this conversation up a little?" I asked. "I was hoping to get to know you better and to have some fun conversation."

She smiled. "Sure light, fun conversation. Matty, bring us two shots of tequila and some light conversation, please," she yelled to the waiter.

"How about a bottle of Senor Cuervo and you figure out the rest?" he called back.

We laughed. A few shots of tequila later and we were laughing easily and much more relaxed with each other. Neither of us was anywhere close to being drunk, but the mood was much more laid back.

We talked about what we loved about living in Philly. We shared what we did in our free time and what made us happiest. We discovered we both enjoyed going to Long Beach Island and she shared her secrets with me about how she occasionally went in a ladies bathing suit. It sounded like a lot of work to me, but it was very interesting.

"I hate to sound silly or dumb, but you said be honest." I was feeling very comfortable talking about everything with her now, so I continued with my thought. I couldn't help but stare once in awhile. "I was wondering about your boobs. I would have sworn they were real when I first saw you tonight."

"They are real," she said. "I paid a lot of money for real looking boobies. No cheap gel chicken pads for this gurl. These are top of the line boobies," she said and cupped them with her hands. "Want to feel?" she asked.

One question and my cock jumped to life. Did I want to feel? Was she kidding?

"Is that a rhetorical question or are you serious?" I asked. "Because I've wanted to feel them from the second you said, 'Need a towel, handsome?' "

She laughed and slid into the chair next to me. "Go ahead, feel them."

Taking my hands, Annie cupped them under her boobs. Then she moved my hands up and down in a jiggling motion. Her hands caressed over mine and we both started to massage over her boobies.

"You like?" she asked.

"Yes, I like very much. They feel very natural."

"They better! Like I said, I paid a pretty penny for them," she said. "Now it's my turn."

"Sorry, no boobies here," I teased.

"No, but you have something else I've wanted to feel for some time now," she said and moved her chair closer to mine.

"I do?" I asked as if I had no idea what she was talking about.

"You do," she said and looked directly between my legs. "May I?"

Leaning back on the hard wooden chair, which wasn't the only hard wood I was acutely aware of at that moment, I spread my legs a little and said, "Be my guest."

A huge grin crossed her face. I smiled back when I saw her lick her lips in anticipation. God, I was so nervous. I couldn't believe I was finally doing something like this. I'd been dreaming and fantasizing so long about moments like this, I didn't want it to be a disappointment for either of us.

Her hand reached over and rested on my leg. She caressed up and down my thigh as she whispered to me. "Relax, David. It's okay. You're safe."

Her hand moved closer to my inseam and I could feel my cock getting harder. Fuck, I wanted her to touch me so badly. My cock was right next to her fingers. Lying just inside the leg of my pants and resting against the inner side of my thigh.

"Do you want me to touch you?" she whispered in my ear. She was playing with me and I was enjoying it.

"Yes," I said in a voice that was more a whimper than a word.

"Ask nicely," she teased.

Turning to look at her, I realized what she was going to do. Playing with me, she was using my words to tease me. Using things I'd told her during our chats online about how I liked to be tempted, teased, and given direction. Fuck, she was going to torture me with my own confessions.

"Please touch me," I said.

"Is that how you ask? That doesn't sound like you're asking for what you want. Ask for what you want, David."

"Annie," I said and took a deep breath. "Will you please touch me?"

"A little better, but not exactly what I'm looking for, try again," she said as she dragged her nails up and down my thigh barely grazing my cock in the process.

"Annie, will you please touch my cock." I sort of growled it out in a pleading voice, if that's possible.

"Much better, but I'm looking for what you really want. How do you want me to touch your cock? What do you want me to do to it? Be specific, David," she teased as she kissed my ear and sucked my earlobe into her mouth before drawing one nail up the length of my swollen cock as I felt the pre-cum leak onto my thigh.

I moaned at her words and at her touch. "Fuck, Annie. Please," I begged.

"One more time," she said. "If you're a good boy and do it right," she said and let the words hang unfinished for a moment. I looked at her and knew what she was going to say before she said it. She gave me a wicked smile and repeated herself. This time, she finished her sentence.