My Barista: Gratuity

(Dear Lit Reader:

The inspiration has been flowing since I introduced a new barista to the storyline. Here is the next part of the saga. Thanks to Slave, Magical Hands and the others who have read it for me.)

*

Since the interlude we shared in my apartment, Charlene and I had been friendly. Not as friendly as her sister and I were those years ago, but friendly enough that she looked to me for support. There were times she called me to ask advice about guys. There were also times when she would call when something made her cry about her late sister. There had only been a few times when she came over for physical reasons. The times we did get physical were nice, but it was apparent that Charlene wasn't very experienced in sexual things. Charlene was surprisingly predictable although she was very beautiful. As a friend with benefits, it was difficult for me to offer ideas on variances in our sexual routine. That was the way it was until one particular Sunday morning.

At the coffee place she worked at, Sunday was otherwise known as Lingerie Day. This day was a bit risky just because the town we lived in was more conservative on Sundays. It was one morning when I was awakened by my doorbell. As I looked through the peephole, I saw Charlene wearing a brown trench coat on the other side. I looked down at the ragged white T-shirt and dark boxers I wore and thought nothing of it before opening the door. Charlene walked in and hugged me just as the beginning of an erection began awakening.

"Good morning, Hun," she said in her fake Southern drawl she used to squeeze more tip money from her overly horny clientele.

"Morning? What did you wake me up for?" I replied forgetting for a moment what I was doing.

"Well, I can always call you later, but then it will be too late."

"Too late?" I asked. "Too late for what?"

"Too late before I lose my nerve," she answered before she undid the belt of her coat and opened it before dropping it to the floor. There Charlene stood before me wearing a blood red corset that squeezed her breasts tightly. She wore a black G-string to cover her pussy as well as matching blood red stockings that were hooked onto her garter belt. A pair of black heels finished the outfit. My awakening stiffness became fully aroused at that moment.

"Lose your nerve to wear that outfit? It is gorgeous, Charlene."

"No, the other thing. You see, there is a tradition at the shop that if you worked on Sunday, you not only wore lingerie. You also had to get freshly fucked before you arrived at work."

"That seems to be no problem, Angel. It seems as if a part of my body already is willing to assist in your conundrum."

"No, not yet. You see, today is my first Sunday which means....." She began to struggle for a way to explain her problem without using the crudest of terms, but failed.

"Sunday virgins have to take it up the ass!!"

The way she said her last statement almost caused me to climax immediately. There Charlene stood looking like the sexiest creature on Earth and actually confiding in me that she had to take some of my semen up her rear entrance. Just the thought that Charlene might have been an anal virgin was already causing ideas to form in my mind. As I thought about the possibilities, Charlene stood for a moment before she walked into my kitchen.

"If I knew you'd have that kind of reaction, I'd just not work today," she angrily huffed as she reached for my bottle of Jack Daniels. As she poured herself a shot and attempted to swallow it quickly, I walked over to her right before she began to shiver from the shot. I walked behind her and wrapped my arms around her before I began to kiss the nape of her neck. I felt her hand reach for my arm as I took a little skin and began to suck on it, eliciting a moan from her. She turned towards me and planted her lips onto mine before we started kissing deeply.

She then pulled back for a moment before she reached down and pushed the G-string down to the floor. As her panties reached the floor, so too did her knees as she began to reach into the fly of my boxers for my cock. Her velvety hands pulled my member out slowly before she slowly began to lick over the head. I leaned against the bar as I watched her mouth slide over my knob. I felt over half of my member sliding between her lips before her eyes looked up at me. As she allowed my dick to slide out all shiny with her saliva, she gave me the naughtiest of smiles.

"We have to hurry. I need to be at work in an hour," she said as she rose up and ran off to my bedroom. I followed soon behind her grabbing a condom and a bottle of lube before entering. By the time I reached my room, she already assumed the position on the bed. I saw her naked rosebud framed by her delectable ass just waiting for her rite of passage. I knelt behind her and began to lick her pussy from behind.

"What are you doing?" she asked.

"Angel, taking this gift from you requires some preparation. Firstly, I need to get you ready. If I just ritually shove my dick in, not only will it hurt you but it can also do some damage also. I need to get you ready first." I started the prep by allowing my tongue to slide up from her juicy box and slide over her rosebud. It started to open a little as my tongue slid up before I lowered it again to her box. I started licking her pussy and bringing some of her juices up towards her ass to help things along. I could feel her wriggling from the attention.

"Would you like to lie on your stomach for a little while, Hun?" I asked before she simply allowed her knees to give, but kept her legs spread open. I continued my oral assault, taking my time until I felt that she was ready for the next step. I stood behind her and walked to my nightstand where I kept an anal plug from when my wife and I were exploring each other. I took it into the bathroom for a quick rinse before I dried it off. I then walked to where Charlene had her head.

"Okay, Angel, you need something to distract you while I prep you more." With those words, I sat on the bed and guided Charlene's mouth onto my cock while I scooted her ass within reach. As she took my cock back into her mouth, I applied some lubricant onto the toy and slowly began to slide it inside her. I could feel it taking effect as her mouth began swallowing more of my cock as I slowly inserted the plug. It was soon to the point where the plug was all the way inside Charlene's rear and I felt the resistance ebb away. I could feel my knob hardened to the point I knew it needed to be. As I slid off the bed, Charlene looked at me.

"Don't worry, Angel. Just getting this condom on."

"No," she said. I looked at her.

"Are you sure? We've never done it without..."

"Please, fuck my ass. Cum in my ass. Please."

With the last request made, I slid in behind her as she propped her rear up high enough so I could see the plug. Slowly, I began to extract the plug as she moaned. A few moments later, the plug was completely out exposing a nice hole to slide into. As I poised my dick near the opening, I asked her again.

"Are you sure?"

"YES!!!!" she yelled as she backed into me until my dick slid into place in her prepared rectum. Slowly, I waited until she was use to the invasion until I slid in again.

"WHAT ARE YOU WAITING FOR? FUCK MY ASS!!!!!" she commanded before I slammed all of my length inside her and began to stroke. I watched as her head thrashed back and forth partially in ecstasy. She turned to look at me with a fierce hunger in her eyes as she started talking even filthier. She kept telling me to fill her ass as I furiously stroked inside of her. It soon became apparent that I was about to climax when she started thrashing herself in front of me again. Three more strokes and I felt my cock shoot powerfully inside her enclosed bowels. She seemed to cum right after that as I sat there reveling in the thought of what had occurred. As I slowly pulled out, I could see her collapse on the bed. I quickly grabbed a nearby towel just in case as I crawled onto the bed. It was then she turned her eyes to me with a weary smile.

"I forgot to tell you my first Sunday shift is next Sunday," she whispered before her eyes closed. All I could do was laugh.