tagTranssexuals & CrossdressersCharlie Takes Charge

Charlie Takes Charge


There she was behind the counter, the same place I first saw her and the same place I find myself needing to return to, to just to catch a glimpse of her. My eyes wouldn't release themselves from Lauren's dark hair, it was long and straight, the two things that guaranteed a hard-on. Her voice was deeper than most women, a thicker, sexier, 'I'm going to fuck you and you'll like it' kind of voice.

I would see her at the bank while making a deposit or getting some quarters for the washing machines and dryers in my building. There was no doubt in my mind she was transsexual, she spoke deeply but tried to reach a higher pitch, a feminine pitch. When I first met her, her hair was shorter and she was just working into her female self I thought. We'd have short conversations about life, football or she'd try to sell me something the bank was promoting, either way it got me her attention and she got all of mine.

Lauren was 30(I was 40 at the time) about 5'10" in heels, big brown eyes and an ass you wanted to spank. Shapely legs and growing B cup breasts filled her out just right. That day she was wearing a black skirt with matching jacket and white blouse underneath which hung low enough that a bit of the seam between her breasts could be seen. As she handed me my money, Lauren smiled and flipped her dark locks over her right shoulder. If I was right, that was one of the non-verbal flirting signs for woman, but did it apply to transgender?

I said goodbye, not truly wanting to leave but eventually it would have gotten awkward had I just stood there and stared. Flirting would have been obvious but I was never good at figuring out if woman were actually flirting with me or just being cordial.

The day went by as it normally did, running a few errands here and there till I got hungry. There was a small bagel shop/deli up the street so I stopped in for a sandwich. Upon ordering I hear, "Well hello stranger," which made me spin in the direction of the voice.


"Long time no see." Lauren joked.

"Yeah, what brings you here?"

"Lunch, it's not far from the bank and they make a good sandwich. I'm starved." She winked and looked me over. "What are you going to eat Charlie?"

"Oh I don't know, probably a turkey on rye with mayo, nothing major."

"That sounds good, order two, lunch will be on me," she said.

"Are you sure?" I asked as she got closer.

She nodded and as I'm about to order after turning to face the counter, she whispers in my ear, "plus your kind of cute."

Obviously I turned red instantly, hoping no one heard her. Open signs of affection weren't my thing. She retreated to the refrigerators to get two bottles of water and come back to the counter. While putting the bottles down, she rubbed one of them along my ass. I felt it but refused to acknowledge it for now. The woman brought out our wrapped sandwiches and rung us up. Lauren paid the 10 or so dollars for our purchase.

"You want to go to my place to eat? I've got an hour. It's less than a mile away." She walked towards her green Mazda.

"Sure, why not." It took me awhile to come up with an answer since I didn't expect her forwardness but admittedly I did like it.

It took less than 10 minutes to get to her place, it was huge. It wound up being a loft with 3 bedrooms, one and a half baths (the full bath had a huge Jacuzzi tub), dining room, etc, all separated by movable walls.

"I thought you were just a teller," I laughed while gazing at every inch of the room.

"Oh no, I just fill in if needed. You like it?" She put our sandwiches down to the four chaired table in the kitchen.

"Yeah, it's real nice. Roomy."

"Thanks. Sit down." She smiled and pointed to a chair.

Not many words were said as we ate. I was more afraid of spitting my food when I spoke, so I wasn't taking the chance of embarrassing myself. I'd look up every now and again to just look at her, admire her; our eyes would meet once or twice which then followed with a mischievous grin.

Once our sandwiches were done she asked, "So tell me about you, handsome?"

"Me? There isn't much to say. Moved up here a few months ago after I got laid off and trying to find a job, taking some classes online. That's about it." I took a slug of water.

"You have a girlfriend or wife?"

"Oh no, been there done that, crashed and burned. Not doing it again." After the words left my mouth, I couldn't help but look at her body, from her spiked heels to her ample hips, Lauren's chest to the dark locks that reached between her shoulder blades.

"You want one?" Lauren rose from her chair to stand directly in front of me, turning my chair forward so she could stand between my legs.

"Don't know, you asking?" I teased her.

"You know don't you."

"Yes and I don't care." I shook my head and shrugged my shoulders, I truly didn't. She was simply too hard to resist.

"Show me," she stated.

My hands went to her skirt, unhooked it then let it gracefully fall to her ankles. My lips would put soft kisses to her belly once I lifted her blouse. With each peck Lauren would let out a small hum or moan. "You know what your doing don't you Mr. Morris."

My hands grabbed her hips to pull down the black g-string panties, they rested upon her skirt. There it was in front of me, dangling as much as it could while being hard. My tongue would tease the tip as Laurens hands got a firm grip of my hair. I knew I was Bi since being with Amy and was about to take another cock into my mouth. I didn't hesitate as much as I did the first time. In one breath I let it reach the back of my throat and have it sit there for a few seconds so I could adjust to its length and girth. I'd then start a sweet rhythm of going back and forth on it. With each swallow Laurens grip got tighter as she would try to lead me down and away from her cock.

"Suck it baby, please suck it."

I did as she asked while squeezing her ass for balance. A few more times back and forth, slurping on the pre-cum that oozed from Laurens clitty and she was nearing an orgasm. Now she was forcing my head down and keeping it there, my chin tapping her balls, the warmth of my mouth extracting the cum from them. Lauren's body shook once her cum reached its breaking point. I choked and gagged a little, refusing to show her that I was barely a beginner. Pulling away, my tongue licked up the few droplets left on my lips as I looked up to her.

"Are you a slut or dominant?" I said bluntly. She leaned on me to keep from falling as I got to my feet; my shirt came off over my head.

"I'm a slut Charlie." She said while regaining her strength.

"Good I prefer that as well." I got a good handful of hair and yanked her head back, pulling her down to her knees. Bending over to put our first slow lustful kiss to her lips I said, "You'll do what I want, when I want it, where I want it...Understand? There will be no turning back from this moment girl."

"Yes Sir," she said with conviction.

"You have no idea what deviant things go through my head Lauren. Are you sure you do not wish to have a day to think about my proposition?"

"No, I want you to do as you wish with me."

Looking deep into her brown eyes I put one more kiss to her red lips then stood. "Get the biggest bowl you have, fill it with water, we shall start slowly. Your head will need to fit in it completely. Then bring me what toys you own, I will choose my weapon."

With a childlike enthusiasm she got to her feet and ran to the bedroom to gather the dildos, butt plugs, lube and such. Going into a closet she pulled out a bucket, not too big, not to small. It was originally made to hold ice so a few beers can get cold. The bucket held about 4 gallons of water, more than enough to suffice my aquatic fetish and certainly wide enough to immerse her head.

Going through the small bag I found something interesting and useful, a riding crop.

"Put the water on the counter, put your head over it and spread your legs for me whore."

She did as was commanded, finishing with, "Yes Sir."

Standing on her left side, my hand reached for her head and shoved it under the water, holding her there for a good 10 seconds. Giving her a chance for a breath I shoved her under again, going for another 10 seconds. Laurens hair was now soaked and hanging over her face. Her body trembled from nerves.

"You will do that on your own now. When I say 'under' you'll stay underwater until you are in need of air, if I do not see you panting for breathe, I'll make sure you need it. Understand whore?"

"Yes Sir," she replied softly

"Under," was stated clearly and she put her head into the water. It would now allow both my hands to work over her slick, hairless body. The implants she had for breasts felt more real than I anticipated. Each hand reached around to cup them from behind as my recovering cock poked at the crack of her ass. She moved the moment I released her tits. Air rushed into her lungs, then back under she went. Her immediate obedience wasn't something I expected, but was a pleasant surprise. Taking a step back, my hand gripped the handle of the riding crop and administered a quick whack to her left ass cheek then the right.

"Thank you Sir may I have another," came from Lauren while taking a breath. So I did exactly that, but I reared back a bit more to make the sting a touch harsher. Bubbles flowed about her hair to come to the surface as she let out a yelp. The next round would be a bit more punishing. I'd use my right hand this time while the other slid into the bucket to hold her under sternly. Going back then coming thru my hand left an imprint on her cheeks as she squirmed in my left hands grip. Yanking her up, she yelled, "GOD... FUCK..... AGAIN...... PLEASE!"

Drops of pre-cum fell to the floor from her stiff drooling clitty. I'd change my target this time. The tip of the crop was patted to the inside of Laurens leg enticing her to spread them even wider and she obliged. The tip then touched her balls, rubbing over them. Taking the crop back a few inches, I tapped her balls gently as her head pushed against my hand.

"Enjoying this aren't you whore?"

"Yes Yes Sir....Please, please can I cum for you? I need to cum for you; it hurts to hold it any longer Sir." She had no clue how hard I had become by just seeing her wet hair, I wanted to wrap my cock in it.

"Stroke yourself off and I shall watch a whore cum. But you had better stay in the bucket or it will be the toilet bowl next," I said. She cooed from the possibilities. With her own hand on her cock and her head underwater, I started to stroke myself. Lauren's sweet hips would sway back and forth as she got closer to letting out her load. Bubbles went from small to large and exploding with screams of need. Taking a step to her, just as her legs shimmied I put a hard slap to her ass. Her juice squirted onto the floor and the cabinet below. Lauren screamed so loud, water splashed out of the bucket. Coming up, she flung her hair back, wetting me and the walls behind us, bringing another satisfied smile to my face.

With seconds to react, the tube of lube was used to lather up my cock. Taking a hold of Laurens hips, I thrust my cock into her pussy until my balls slapped hers. The water dripped onto the floor from her hair, neither of us cared as I was now fucking the rest of the energy out of my whore. Her feet squirmed forward to get to the counter; she knew my rules. Back into the bucket her head went, the slut's hair now covered the entire surface of the water. Keeping a firm grip of the counter with her hands, it allowed me to penetrate her even deeper.

"You are a sweet wet whore."

"Thank you Sir, thank you, please fill me. Use me as our whore, your slut, your personal cunt."

With her words, the water and the excitement, it didn't take me long to fulfill her needs. While on my toes, I could feel my cum fill my cock and creep slowly forward, spewing from the tip into her pussy. As Lauren came up from the bucket, she gasped for air loudly.

"Clean it," I demanded.

Slowly and carefully my whore got to her knees, put her red lips to my throbbing softened cock and cleaned it perfectly. Pushing my hips forward purposely, I'd make her gag; the sound was music to my ears.

"Call work and tell them you need the rest of the day off. I think we will lay in bed for a bit to recover for your next lesson."

"Yes Sir," a grin snuck thru her soaked locks.

Report Story

byRhynovampire© 1 comments/ 14843 views/ 4 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartAkhiljha, cock_ryder_69 and 2 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (1 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (1)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: