Bartender Gets His Fill

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Rookie bartender gets a lesson in BDSM.
1.7k words
4.23
44.3k
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Part 1 of the 2 part series

Updated 09/22/2022
Created 07/23/2001
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I started bartending because I though it would give me a great opportunity to get laid. From all of the stories I have ever heard bartenders seem to get the most action, maybe I got the idea from watching "Cheers." Anyway I was a senior in college and had plenty of action with the sorority girls, but wanted to get with some more mature women and experience new things.

I had been on the job for about a month and noticed that there was one woman who came in all of the time. I knew what she liked and always had her drink poured before she even sat down. She frequently the most stunning outfits that seemed to cling to her figure. She had beautiful 36d tits that screamed to be freed from the tight clothing; she was about 5'9'' and always wore the highest of heels and the shortest of skirts to show off her long legs.

After a month of her coming into the place I noticed that she turned everyone down no matter what their line was or what they looked like. My curiosity got the best of me one day and I started having more of a conversation with her then just the usual. "What'll you have?" I asked her what she liked about his place since she was not looking to hook up whenever I saw her. I just re She coyly replied back that she was looking for someone to, "hook up" with and smiled at me as she made the quote signs. Embarrassed for acting immaturely I blushed. She went on to say that she was just waiting for me to approach her. I asked her," Why?" and she told me, "I'm just following orders."

I looked at her confused and she shook her head saying, "Don't worry about it." She then asked if I would like to come to her apartment after I got off work. I tried to stay cool and reply yes, but I'm sure it came out like a schoolboy overly anxious about his first time. In a lot of ways this would be my first time not only with an older woman, but now as I look back I realize that I was still very inexperienced in many ways. The rest of the night I battled with my hard on unable to control my thoughts about what I was going to get later that evening. I wasn't even close.

She waited at the bar until it closed and drove me to her house, we shared small talk while I continued to try and hide my hardon, which was pretty impossible now that I had my apron off. She told me her name was Brandi and had been scoping me out from the first night she had walked into the bar. She then smiled at me and began rubbing my 8" cock through my pants telling me it wont be long now.

When we arrived at her apartment, which was more like a loft, one huge area with the bed right in the middle. She kissed me and told me to take my cloths off and wait on the bed. I stripped quickly as she went into the bathroom and jumped on the bed. Being so anxious about what I thought was coming up the black silk sheets and candles never clued me in what she was into, but when she walked out of the bathroom in a white leather bra and panties I began feeling like I had no idea what I was doing. I've never been into the whole D/s thing, but was about to get a valuable lesson that opened my mind to a wonderful option when it came to sex.

When Brandi asked me if I had ever been tied up, I giggled as I said no. She smiled as she instructed me to lie on my stomach. She then chained each of my arms and legs to the four corners of the bed. The chains were long enough to allow some movement, but I felt extremely anxious realizing I was totally in her control. She then grabbed a black silk scarf and asked if I new what it was for. When I said No she laughed as she blindfolded me. My mind was racing, here I was lying on my stomach not able to see anything or free myself, this was already the most exciting sex I had ever had and we had not even really done anything yet.

Brandi told me to relax and that I would have the most intense experience I had ever dreamed about. I took a deep breath and waited for her to do whatever it was she was going to do. Then out of nowhere I heard her say, "Did I do good Sir." I was about to respond when I heard another voice in the room say, "Yes slave you did very well." I was terrified; there was another man in the room while I lay there naked and helpless. He then went saying, "You, are now my slave as well. You will refer to me as Sir and will follow all of My directions. Do you understand?"

I was terrified. I couldn't speak. All of the sudden SMACK, I yelled out in pain as my bare ass was spanked my by what felt like the biggest paddle in the world. I heard him ask me again if I understood and I cried out "Yes." SMACK, I was spanked again this time even harder. A tear fell from my eyes as I screamed "Yes Sir!"

Even though the spanking was extremely painful I also felt a shiver all over my body, I could feel that my cock was as hard as ever under me, and I realized that I was getting even more excited. Now I know why those Frat boys like paddles so much.

I have never been with another man, but had always been curious about what it would be like. As I was thinking this I felt a tongue slide down my crack and lick my ass, it must have been Brandi. The Master ordered me to lift my ass, which I did immediately knowing a spank would be forthcoming if I didn't. He said, "good slave" as he slapped my ass. Feeling Brandi's tounge playing with my hole at the same time as having my ass slapped sent another wave of conflicting sensations all over my body. I thought to myself, "This is what I happens when I followed directions" I was not about to disobey even though I was nervous about the possibility of having another man having sex with me.

He asked me if I had ever sucked another man's cock before, when I told him, "No sir" I felt him slap my ass harder this time. This was definitely not as painful as the paddle, but it did sting. Brandi had now positioned herself underneath me and was sucking my balls taking them in her mouth. The feeling of pleasure from this caused me to hesitate when I was asked if I wanted to suck his cock. SMACK, I fell forward into the headboard as he paddled me. "Yes Sir," I screamed before he paddled me again, not realizing what I had just agreed to until a second later when it sunk in that he wanted me to suck his dick. I had received numerous blowjobs, but I had never given one, and I wasn't sure what to do. I realized he was climbing on to the bed. "Open your mouth," he ordered. I did so.

I felt the head of his cock against my lips and I when I wrapped them around his cock. He told me "good slave" he pushed his cock deep into my mouth gagging me. He cock was bigger then mine, probably 9inches, but his cock was also extremely thick and I had to stretch my mouth to get him in before he pulled it out. "Do you like that slave?"

"Yes Sir" I quickly responded realizing that I wasn't lying I really did like it. Especially feeling Brandi continue to suck around my balls then around my ass again. She still had not touched my dick. God, I was hoping she would.

He asked me, "Do you want more of my cock?" I said, "Yes sir" and felt a slap against my face. He had just slapped my in the face with his cock. I was embarrassed and confused when he stated, "beg for it slave."

"Please Sir, may I suck your cock." I felt it touch my mouth again and I opened my lips around it, twirling my tongue around his head before he pushed it deeper into my mouth. I was more relaxed this time and refused to gag as he pushed deep into my throat Brandi was sliding her tongue into my ass as he began to fuck my mouth going in and out. I moaned deeply feeling her tongue in my ass and his cock in my mouth. I knew the master was happy, he started fucking my mouth harder and faster, grabbing the back of my head pushing as deeply as he could deep into my throat.

"Are you going to swallow my cum, slave" I knew I didn't have a choice but really did want to. I grunted assent as he fucked my mouth faster and faster. My tongue feeling his shaft as it moved in and out. Brandi pushed a finger into my ass and it was all I could do to control my self. My cock had not even been touched yet and I was feeling more pleasure than I had ever felt. The master began cumming. I felt his hot load shoot deep into my throat causing me to gag again. I kept my lips closed tight around his cock feeling it pulse in my mouth shooting cum out of his cock. I had never paid attention to the amount of cum I had ever shot out, but I knew it had never compared to this. I kept swallowing it squeezing my lips tight around his cock milking everything I could out of it. I had never tasted anything so wonderful.

Brandi stopped fucking my ass and the Master had finally pulled out of my mouth. He told us once again, "Good Slaves."

I still hadn't had an orgasm, but felt exhausted anyway. The master ordered me to lie there and wait.

There was definitely more to come.

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