Confessions of a Slut Ch. 23

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A 24yo woman moves to Florida and finds her way.
1.8k words
4.61
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Part 25 of the 29 part series

Updated 06/10/2023
Created 12/14/2020
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Derek's cock pulsed and unloaded into my mouth. As I swallowed his cum I couldn't help but feel a tinge of disappointment. I enjoyed sucking dick. I enjoyed sucking Derek's dick. But Derek and I hadn't had sex in nearly three weeks now. There were plenty of blow jobs but no sex and I was growing frustrated.

I had woken up this morning to find Derek asleep, yet hard in my bed. I pulled off his underwear and woke him up with a fantastic blow job. Too fantastic it turned out as he barely lasted three minutes. He laid there, not moving or talking until he came. He had no ability to hold back when I blew him. My hopes for sex would have to wait.

"Thanks babe," Derek said as he looked down at me between his legs and pat me on the head.

I wiped the saliva off my mouth and managed a fake smile to hide my disappointment.

"What time do you work today," he asked.

"I work the early shift. The early football games and then I have the night off. You coming over tonight?"

"No. I work the night shift tonight."

"Okay. We'll I'd like to see you again soon so let me know the rest of your schedule this week once you get it."

He got dressed, gave me a kiss on the forehead and left.

No more than five minutes later Courtney's moans could be heard through the walls. I had been woken up in the middle of the night to these same moans. The fact that her and Mark were now enjoying a second helping made me jealous. I grabbed my black dildo and decided to have some fun of my own.

*****

The bar was fairly empty for a Sunday during football season. Courtney was sitting at the bar. In a turn of events she had quit her job bartending for an office job. She wanted to align her schedule with Mark's so they could spend more time together. She had brought Mark with her to the bar, as well as his friends Donnell and Robbie. Donnell was a half-white and half-black. He had cappuccino skin and a mustache which made him look older than his twenty-three years. He was six foot four inches and a former Division Three basketball player. His hand swallowed mine when he grabbed it and kissed it during our introduction. Robbie was also tall, around six feet one inch. He had short cropped hair and a goatee. He was hot and he knew it. If I didn't already have a boyfriend Robbie was definitely someone I would date.

The games were uneventful and customers scarce. It gave me plenty of time to talk with Court and her friends who were drinking at a steady pace. Courtney caught me eyes with hers and nodded to her right. I looked over. It was Bill. I walked over to take his order.

"What can I get you Bill?"

"Scotch on the rocks kiddo."

I hated when he called me that. It transported me back to his hotel room when he told me to leave after swallowing an ungodly amount of his cum.

"Blow jobs aren't cheating kiddo, but you should leave regardless."

Those words from nearly a year ago still irked me.

I served Bill his drink and walked to serve other customers. I overheard Donnell talk to Courtney and Mark.

"Hold up. She sucked that dudes dick?! He's gotta be fifty!"

I spun and angrily eyed Courtney. Her gossiping about my sex life with others was wearing my patience thin. There were a lot of things Courtney had been doing lately which rubbed me the wrong way. We would talk about this later.

Courtney and her crew paid their tab and left over my objections. They were all fairly drunk, but Robbie said he was sober and promised to get everyone home safe.

My shift ended soon after and despite Bill's best effort to convince me to come to his hotel room again, I had climbed in my car to head home. I was once again at the familiar stop light. Turn left and go home or drive straight and stop by Jimmy's. This time I turned left.

I arrived home to find the party had moved from the bar to my living room, only the party had begun to crash. Courtney was laying down with her head in Mark's lap. Robbie was sprawled out in the other side of the sofa. Donnell was sitting at a table behind the sofa sipping what looked like bourbon.

"Are they crashing here?" I asked Courtney.

She didn't answer but Robbie did.

"If that's ok. We've all had a bit too much to drink," he said either sleepily or drunkenly.

"There's blankets in the closet and a spare bedroom upstairs."

Without saying a word Donnell stood up, put his glass in the sink, and followed me upstairs.

I could feel his eyes on me as I had all night.

"The spare room is there to the left. But..." I hesitated. "You could stay in mine if you want."

He needed no more prodding. He came into my room and shut the door. I had been left frustrated this morning and this was the result. The embarrassment of my lack of self-control was eclipsed only by my belief that Derek and his inaction had pushed me to do this.

I took off my shirt and unclasped my bra. My impatience combined with my neediness had me wanting to get right to it. I was feeling sultry and I wanted to lead with my best asset.

"Damn," Donnell said as he made his way over. His lips engulfed mine as his large hands molested my breasts.

He was too tall to keep kissing like this so I sat him down on the bed. I lifted his shirt over his head to expose a well-defined physique and climbed on the bed next to him. We playfully rolled around on the bed - one second me laying on top of him kissing his chest, the next second him on top of me doing the same. We took turns unbuttoning and removing each other's pants, all while making out. Multi-tasking at its finest. His hands reached down and I could feel his long fingers sliding deep inside me. They went incredibly deep and a moan escaped from inside of my mouth and into his as we kissed more passionately. Things were progressing rapidly and I had no intention of stopping it.

He now had four fingers inside me and the finger fucking I was receiving had made me soaked. I could hear the wetness building more and more. I pulled my mouth from his, gasping at how good this felt and embarrassed at how wet the sheets had already become beneath me.

I closed my eyes as his fingers brought me to climax. I pushed his fingers out of me and took a second to gather myself. I reached down and grabbed his dick and did a double-take at its growth. It has looked like a normal limp dick when I had taken off his pants earlier but had since grown impressively. He wasn't thick but he made up for it in length. It was huge; about eight and one half inches I guessed.

He laid on his back with his head on my pillow. I held his long, skinny cock in my hand unsure of what to do next. It was hard but not rock hard. It had some flexibility but gained firmness as I slid my hand up and down its length.

My indecision was interrupted by his oversized hand cradling my head and guiding it down to his dick. I opened my mouth and sucked the head. I was buying time. I was scared. I knew where this was leading and I was intimidated by his length. He was over and inch bigger than Jimmy and sex with Jimmy sometimes scared me. I worried what this dick would do to my vagina given the chance.

I came up with a plan. I would make him cum with my mouth. I was so nervous about his size that I didn't see the obvious solution in plain sight.

I tongued the head of his cock as if I needed to make him cum to survive. I eagerly took two, then three, then four inches into my mouth. I made sure it was the wettest, sloppiest blow job he had ever received. I took five inches and then sucked back up to his tip. Then I took six inches and back to the top again. I pushed myself even further taking seven inches down my throat.

His hand pushed down on the back of my head and my gag reflex kicked in. I pushed my head up, his dick still in my mouth, my eyes now watering. Again, his powerful hand pushed my head down further on his dick. I gagged again, this time forcing my mouth open and expelling a cough. It had turned into a tug of war. His hand pushing my head further down while my head fought back in an attempt to stop from gagging on his length. The battle resulted in my head bobbing up and down as it would during a normal blow job but with a puddle of frothy spit now at the base of his dick as a result of my gags.

The blow job was no longer a blow job, but a mouth fucking. Donnell now had both of his hands on my head and was pushing down harder. My throat was in survival mode and had instinctively relaxed enough to take most of his cock for short periods. My gags didn't seem to phase him and, if anything, made him pump harder.

I wasn't sure how much more I could take. I stared up at him through my watery eyes and managed to pull his dick out of my mouth.

"Are you close?" I asked.

"Yes, very," he gasped.

I returned my mouth to his dick and his hands found my head once again. It was the final stretch and I was ready. I moaned with a mouthful of his cock, hoping it would encouraging him to cum.

It worked. I took what had to be eight inches of him and he came in my mouth. I swallowed each of his loads fairly easily.

I smiled up at him hoping he didn't judge my inexperience at sucking a dick as big as his. The base of his now receding dick was covered in my spit. Embarrassed, I walked to the bathroom and grabbed a wash cloth to clean him up with. I examined myself in the mirror. My eyes were glossed over and streams of tears had traced lines through my makeup.

I still wasn't over his length. If it had been even average thickness my jaw would have undoubtedly become unhinged by that mouth fucking. It stood in stark contrast to the blow job I had given Derek that morning and the more I thought about what had just transpired, the more I liked it. I would have to try it again. Soon.

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