• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • The Bar Pt. 01

The Bar Pt. 01

123

The Bar
(and My First Lesbian Lover)
By MadQuill

Please remember this is a copyrighted work and all legal disclaimers apply.
Though this is the first of two chapters it is a work of Fiction and stands on its own.

*****

I slept with a Lesbian a week ago. It was a remarkable night of sensual sex. It was a first for me yet it opened my mind. She was in town visiting the Foundation and we crossed paths in the restroom. There were no other people using the ladies on my floor and she stopped as she dried her hands and just look at me and I knew.

"I don't think we've met. I'm Darra," she said walking toward me.

She stopped near the stall that I had opened. "I saw you from the Atrium."

I smiled and considered her flirt, "Yes my office is on the north wall." I hadn't moved.

"You've got a nice smile."

I looked down at my heels, "My parent insisted on braces," I pursed my lips.

"What division are you with, Jessie right?"

My name was on my pass but it was partially covered. I had to be careful for I was really happy working at the Foundation.

"Ah, yes, Darra. I need to pee, excuse me please."

I heard her leave the space.

Twenty minutes later near four-thirty she walked into my office.

"The view across the Atrium and to City is marvelous Jessie." She sat down across from me. "The team I'm working with had to settle a matter. I'm free. Do you want to get a drink?"

I studied the outfit Darra wore. Power heels with a strong thick heel, chunky, but not sexy or too tall. The leather was a matte grey. Her legs were covered in very sheer nylons. I could just see her knee as the hem of her skirt had risen a bit as she sat. The ribbed black material of her skirt was elegant. A belt held her soft beige blouse which had a strong collar accenting Darra's lovely long neck. Her makeup was strong for an office meeting but maybe she did this to conceal her sexuality. She looked a little to femme. There was no shade line on her ring finger. In fact on her right hand she wore a diamond on her middle finger. Darra had soft almost strawberry blonde hair but it was up and I could see subtle hints of grey.

I looked at her face for long enough for her to understand yes and then checked my clock, "Sure. Say we meet at the bar around the corner, its called Espirit. I need another twenty minutes Darra."

She sat a moment longer and I saw her tongue moisten her lower lip. "I'd like that Jessie."

At five I entered the busy corner bar. I had been here three or so times since it opened last year. It was a pleasant crowd. Not too many sports TV's on. Just the unit over the bar and it was tuned to CNBC. I looked about and saw her in a quiet spot in the corner.

Sitting down I noticed that she had changed for now her blouse seemed to expose a white chemise with lace. She had removed her bra. I paused before taking a seat and starred.

"I'm glad you've noticed Jessie."

A little fluster I put my bag beside hers on the unused chair and I could see the strap of the bra partially exposed at the bags zip.

"You must excuse my stare Darra." I sat down. "I'm not accustomed to meeting women at the Foundation. There are no rules but most of the gals are married and after talking about their kids and husbands I guess I get bored and, I'm nervous, a little."

"I've ordered you a Pinot, there's the waiter. Thanks,"

"You've guessed right. The red will be nice."

We talked of my legal work at the Foundation and she shared that she was in town for just two days. She lived near Detroit and the non-profit she was with had requested some aid. She wasn't married nor in a relationship. Twenty minutes later I needed to clarify myself.

"I'm truly flattered that you find me attractive Darra but no one mentioned?"

She smiled, "My eyes are a good read and your legs are just so sexy Jessie."

I considered her pass. She had missed that I wasn't all female. I had to share my secret.

I looked into her eyes intently as I spoke the words.

Her smile never wavered, "You're saying you don't want to go to bed with me Jessie?"

Maybe she didn't hear the words correctly due to the hum of the bar's patrons, "Darra, I'm a woman who would love to go back to your hotel but I'm, transgen , "

"Oh, what did you "

Now she understood yet her face didn't fall, "Oh Jessie you're testing me." She paused and considered me.

"Seeing if I'm paying attention," but my statement settled into her mind.

Ten seconds passed and her eyes never left mine.

"Okay, so that's a surprised. Yes Jessie. You're really not a girl?"

I started to get up, "Wait, please. Let that idea, I mean to say, don't leave Jessie."

I shifted slightly and looked into her eyes and then sat again. I looked back to Darra.

She pursed her lips, "I'm a little unsure Jessie,"

Without her eyes leaving mine she slowly reached across the table to my hand.

"Yet I'm more open minded than most, especially most lesbians who live in the mid-west."

She lightly placed her hand atop mine, "You definitely fooled me."

I pulled back and she did as well. "But I didn't try to, I mean you,"

She interrupted, "I understand, but you don't look, I guess I want to say that you look so feminine."

"Of course I do, I'm a woman. Just not quite a GG."

"A what? Oh, yes, I get it, a gender girl."

She looked at me, "You are to my eyes still attractive," but I wasn't sure what she was thinking. She seemed unconvinced until she smiled warmly.

"Will you come with me to my room?" I nodded.

"Come on, in fact let's go."

The waiter saw her hand and I sat while my new friend paid and we stood to leave.

Coming close her hip touching mine, "Jessie, I want to kiss you."

The bar was now crowded and some other girls had taken our table.

It was a soft sensual kiss on my lips. One of the women hooted, "yeah, I'd take that one too,"

Pausing I said, "That was nice, Darra."

She took my hand, "I've got a bottle of wine at the room. We'll share the evening. The hotel is a five minute stroll."

The lovemaking with Darra changed how I thought of myself. There was no penetration or toys involved. She started in the hall with the door to her suite open kissing me. She liked the risky public kisses but her hand had slipped into my dress and she caressed my right breast gently rubbing the nipple as her tongue took control. I was shorter though we were both wearing heels. Darra was slim but not skinny. I'd have guess she had five pounds and two inches on me.

"I like to lead Jessie, " the kiss paused and she took my hand and we closed the door.

Once the door closed I pulled her to my mouth as her hands released my dress and she pushed it down to my hips. The slip followed and her fingers felt that the bra I'd wore was a front clasp, "Tricky little bitch is holding what I want," she softly said as she pulled my breasts free.

I smiled as she looked at me while dropping slightly to slowly lick at my left breast and teasing the right nipple in her fingertips. I moaned, "Yes, yes, Darra."

I pulled her upward to my mouth again, "More kisses please," she had a powerful tongue and it was still sweet from the wine. Her hands cupped both of my naked breasts. She smiled and pressed them together.

"This a quite a rack Jessie and I love to play with my lovers tits." Her right knee was between my thighs and she pressed my sex, "and your mons is quite flat for a girl, well you know."

Her face was inches from mine as she smiled and that tongue again assaulted my lips. My hands had pulled her skirt up and my fingers played along her butt cheeks,

"Where are your panties?" I said as I pulled back a bit from her kiss.

"Humm, took you long enough to find that out. In the purse Jessie. I'm naked for you and my juice is running down my inner thighs."

I dropped to my knees and saw her pink bare lips and the glistening drops of her nectar, "Oh Darra, " my mouth covered her mons as my tongue slid down to her clit.

"Wow, that's a surprise too," I said seeing her clitoris. It was engorged and nearly a quarter of an inch in length. I'd never seen such a big one.

"What a beautiful clit sweet Darra," as I licked along the side. The hood slowly receding as my licking stimulated her.

"Oh god yes Jessie, lick me, please," I pushed my long digit into her vagina as she moaned.

"Two fingers girl, deeper," She was moving her hips in a subtle circular motion as my tongue wrapped about her clit and my fingers slid in and out of her wet pussy.

I looked up to her face to watch her; eyes closed and her hands caressing her own breasts.

I paused my licking sensing her peak was near, "Are you so wet because of my sex or my loving tongue?"

"What? Get your tongue back to work Jessie! Yes, it's the idea that you're so feminine that I missed that you've got a, I mean, yes, that's so good, ahhh," She grabbed my hair and held my head tight to her pussy.

My third finger retracted but my long one had found her spot, "Oh Jessie, yes there," My tongue sucked on her clit as I slowly rubbed my finger on her inner wall.

"Ohh fuck, ohh fuck, Jessie, Oh ahhhh, " she climaxed as I varied the pressure on her clit while holding her pussy. She released my hair, "Oh stop, no stay there, oh, oh sweet Jessie!"

We had room service bring a dinner as we sat and drank the Bordeaux. Sitting naked beside her she told me of a lover in Michigan. I asked about her visits to the City. "I'm an avowed lesbian but I want to see you again."

She sipped her wine, "But I'm glad I kept you with me tonight. That first orgasm will be noted in my diary."

"Most lesbians would have walked away at the bar but I was too strongly attracted to you and just a bit to horny to let a little penis get in my way." She reached to my sex, "and you keep it tightly concealed."

She pushed the thong aside and my penis was exposed. It wasn't very big when I wasn't aroused.

"It's a nice bit of cock Jessie," as she held me, "Can I see it hard?"

I pulled her to a kissed, "Leave that alone Darra. You said you would help me understand girl sex. Playing with my toy will only get us into trouble."

She smiled and her hand let go of my penis. I re-tucked and settled the thong.

She was sitting cross-legged on the bed, "There may be others, I mean some women may be interested in you. Your honesty was an important part of my decision to sleep with you. You just need to meet some other lesbians Jessie."

She leaned close and kissed me. Our naked breasts were rubbing, "That feels nice," she shifted her hips and her body started to rub mine.

With my sex tucked and covered by my thong she began to push and rotate her hips, slightly banging her pubis against mine. "You can enjoy this right?"

"Yes" I closed my eyes to relish this new sensation. I could feel my body, not stiffening but aroused by the contact.

She was sliding her body aggressively now and she lifted my right leg to nearly straight up, "Oh Jessie, this is going to get me off."

"I can, I'm not hard but this feels wonderful Darra." She was bumping our sex.

I saw her caressing her nipples and brought my hands to my breasts, "Your nipples are sensitive?" she asked.

"Oh god yes!" She was grinding me and now she reached to caress my breasts.

"Play with me too Jessie, my nipples."

But I wanted to have Darra's pussy. I shifted her about on the bed and pressed my tongue into her slit.

"Oh, but, Jessie, oh yes. Right, right there, yes,"

She came again and I moved to kiss her, "Your pussy is all over me." I kissed her, "And my thong is a mess. I squirted."

Later she wanted to get me to fully orgasm but I didn't want to ruin this girl-girl night. "Maybe on your next visit Darra."

Before I returned to my apartment we sat in the Lounge of the hotel for a few minutes.

"I meant what I said Jessie. You stunned me at the bar and now you've loved my body beautifully. I've met a few transgender girls, you know at parties mostly. The Mid-west, their not as free to be public and most have a tell; tall, over dressed, an adams apple. You know right?"

She had shown me how to climax by simply scissoring another woman.

She had said earlier, "You will only be a girl for me Jessie. Others may want your toy in their pussy but I met a girl."

Now she held me and said, "I fucked you girl."

She touched my breasts through the blouse; I was braless. "You know your implants are quite amazing. I've felt my share of fake tits. Yours are soft." She touched my nipples lightly.

She walked me to the cabstand, "How long a ride?"

I turned and kissed her, "Less than six minutes," and I hugged her and squeezed her bottom. "Until next time Darra."

As the car moved north I considered the evening and Darra's suggestion. I needed to explore more. She had taken a chance and we'd had some great sex. She would be back in the City in a few weeks.

Each evening over the next few days I planned to visit a different bar or club but I chicken out at the first two nights. On Thursday night I went to the Village to try a widely known gay hangout. I arrived just past seven dressed in my ratty gap jeans and a simple white top with three quarter sleeves. I'd worn a pair of three-inch natural wedges and had on only my bracelet and pinky ring. Getting dress was tough; I'd pulled my hair into a ponytail after twenty minutes of misery and removed my makeup twice. I ended up smearing the eye shadow to mute the look and used a soft pink lip balm since I wasn't planning on being kissed.

I was a bit early but sat at the bar with a glass of red wine hoping to not cause a stir. The place didn't fill up though. After a pleasant hour during which I spoke with two guys, a lesbian couple and an evident male-to-female I paid and left. For the first fifteen minutes I had felt uncomfortable but I settled down and just watched quietly the action and various groups.

At the terrace one of the waitresses offered, "Please comeback soon. Usually after nine is better."

Turning toward her voice I said, "Sure, good night." She smiled but I quickly stepped passed.

I was happy I'd ventured out and though I couldn't be certain I don't think I was read. I would comeback, maybe tomorrow after work. The later hour might be interesting and more crowded.

Of the fifty-two women working at the Foundation I had a few girlfriends but only one that cared to spend time with me. I'm not positive but I'm pretty sure everyone knew I was transgender. The married women were just too busy with family issues but they were all nice to me. They saw their goal of eight hours and out as a rule; little to no lunchtime outings. There was one guy who was attracted to me but I wasn't into him.

Linda called and asked if we could head to Bryant Park for lunch. "We'll get something at the deli and just sit in the sun for thirty minutes."

I told her of my evening with Darra but I didn't share that she was a woman I'd met at work.

"I'm not surprised that she couldn't tell Jessie. You don't show any sign of your male past. I'd say getting on to hormones at seventeen sure help though. Look, you don't even seemed to have a bump on your neck."

"You mean an Adams apple?" I chuckled.

She giggled, "Yeah one of those."

"How was the sex? I mean I've never been with a woman, so was it different?"

I told her about the woman's orgasm, "So you didn't climax with her?"

"TMI Linda, but not really. It wasn't one-sided though. She was specific before we got to her room. Girl sex was new to me so I'm glad she was into me you know?"

On the walk back to our building a guy swore at me when I'd tripped on a concrete edge and almost fell into him,

"Dumb bitch. Watch where you're walking!"

That incident fueled the conversation the remaining two blocks. Linda said, "That's a good statement of your gender read Jessie. There are few people who would guess."

"I know but last week a teenager said something when I was at Bloomie's. I was wearing Levis and boots. She said I was 'underdressed' for a girl."

Linda giggled, "Tough review but I think she was just jealous. Your butt in jeans is so sexy."

I punched her arm, "You're looking at my bottom? I was going for the andro look that day. I won't try that again."

Friday night I decided to visit that same bar in the Village but I chose a leather pant and pumps. I didn't change my office makeup look but just touched it up. It was nearer to nine when I arrived.

As soon as I walked up to the bar a guy and girl started up a conversation. I didn't think they were a couple. My voice sometimes broke from the feminine timbre and it did at that moment. I was nervous but maybe the noise of the other patrons had drowned out the error.

The woman was slightly younger and good looking. She was carrying a few extra beer pounds. "I haven't seen you here before, Jessie right?"

So she had heard me but just didn't comment.

"Yeah I've only been here once. It's busier tonight. What did you say your name was?"

She hadn't actually so Tom her friend said, "It's Jane and she does that all the time. Bad with names so she tends not to ask for them."

He was tall. I'm only five-seven but in my pumps I was almost five-ten. He looked to be six foot. Jane was cute, with a dimple on her chin. She was just shorter than me due to the flats she wore. We spoke of the crowd and local stuff when Tom slipped away.

Jane saw a bar stool open and she gently directed me, "The next one will be mine Jess." Now we could speak without the distraction of the crowd.

"I love the mix this place attracts. Tom and his pal, they say their not a couple but. Well they tend to leave together."

She looked at me, "Do you have a girl? Oh or a guy maybe?"

Jane looked a bit uncomfortable, "I can be so rude. I was almost married once. I'd used him as cover."

I didn't know how to answer that, "I'm rambling a bit Jess," she said.

I smiled and raised my hand to get the barkeep, "No problem Jane. We're finding out about each other. No to the girl or guy thing; unattached but looking for love."

"We'll have another round please. Thanks." Jane said and watched her leave, "Marie, she's a sweetie but in love."

I turned slightly to avoid an obvious look, "She looks likes she nineteen! Surprisingly fem huh?"

Jane giggled, "A few of them here tonight."

Clearly she hadn't read me for I was usually dressed femme. She turned to the bar entrance hearing her name called.

"Oh there's Sam and Charlie," she waved at the two women.

Whispering though they were yards away, "They're a new couple and both are old friends from the University."

There were hugs and kissed as the two came to the bar. Marie brought our drinks and Sam ordered for Charlie. I studied them subtly as they caught up with my new friend. Charlie was clearly beautiful and tall. Her long hair was up in a knot and she wore a dress but in flats. Sam or Samantha was in khakis and a vest. Her makeup looked rough, as if she was trying for a new look.

Charlie smiled at me as her lover continued to speak with Jane, "So Jessie, Jane is introducing you to the other barflies?"

I laughed softly, "I'm new to this crowd and having someone say hello was good. We just met thirty minutes ago."

"Okay, then you've got passed all the posturing and questions already. I hate visiting a new queer pub. Sam and I met here, almost three months ago. We're not a true couple though. Maybe, but we'll see." She seemed a little frustrated.

I said to her, "I'm new to the idea, I mean I normally don't get out much and this place may change that. I'm enjoying meeting others."

She was standing quite close as the bar was now packed, "So you're working in law?"

I shared my non-profit job and she told me that she was studying for the Bar exam the following month.

The stool next to me opened and she sat though Sam was at the other end. "I wouldn't wish that on anyone." I frowned with the memory.

123
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • The Bar Pt. 01

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 18 milliseconds