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MILF Waitress

"A lonely mom and housewife takes a job to break up the loneliness. She finds new ways to break that loneliness"

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My name is Dawn. I am forty-two years old and a mother of two. My daughter and son are now out of the house and away at college. My husband works at a distribution center and recently was promoted, which was nice since it was more money and helped with two kids in college. However, the downside to his promotion was that he had to go to the night shift.

My husband would work all night, stay up all day and do what he had to do. He would then go to bed after dinner before returning to work. Because of this, I was always alone and bored. I kept talking about getting a job at night to keep me busy and have some interactions with others. That is when a friend told me that Murphy’s Bar was looking for help. I knew Murphy’s was a bar with a customer base of mid-twenties to early thirty age group. My friend told me they also make a lot of money in tips.

For the next week, I thought long and hard if I wanted to commit to a job or not. Finally, one night at dinner, I spoke to my husband. I told him I was always alone, which would get me out, and we could enjoy the extra money. He listened and said that if I wanted to, he would support me, and I should go for it.

The next day I went to Murphy’s Bar and asked for the manager. We sat and discussed what the job would entail. He told me about working nights, which I knew would be necessary. He told me their servers had to wear the uniform they provided. He told me they had to wear a black skirt and white shirt or a pair of black shorts. They have no regulations on shoes, but most servers wear white sneakers since they are on their feet so much during a shift. My interview went well, and I spoke for about forty-five minutes with the manager. He seemed very nice, although I probably could have been his mother. He told me I would know either way as soon as possible. I thanked him and left.

As I walked out, I noticed all the staff were young. The servers were in their mid to early twenties. I thought they would never want a woman as old as I am. Then, I noticed the uniforms the manager talked about, and I thought, “Wow, those uniforms are short and tight.” Now I was not afraid of wearing something like that since I have always worked out religiously, and I would not worry about seeing my five foot eight, one hundred and thirty-pound body in a uniform. However, I might be a little nervous about my 38DD tits since most of the staff were smaller than that. I worry, should a woman my age be seen in a uniform like that?

I left thinking to myself. It’s not going to matter anyway. The manager probably thinks I am too old for this place. So I went home and thought, “Oh well, I gave it a shot.” A few hours later, I received a call from the manager telling me the job was mine if I was still interested in it. I felt a little proud that I got this job. I accepted, and he told me to come to pick up my uniforms tomorrow. Hanging up the phone, I was so excited that I got it.

I told my husband at dinner and was disappointed that he was not as excited as I was about the news. Guess I shouldn’t have been that surprised since our relationship has suffered over the past few years. Between work-related issues and the financial strain of two kids in college, his stress has been affecting his mood and our bedroom fun.

The next day I went to Murphy’s and was introduced to Mary. Mary was the same age as my kids. She was a pretty blonde with a nice body. Mary took me into the back and gave me all the needed uniforms. She was adorable and friendly as she welcomed me to the staff. I confessed to Mary how surprised they hired me since everyone else was so young. She assured me that I would do fine here.” You are so beautiful the customers will love you, you will make out in tips without a doubt. Just be friendly with them and play the game.” Mary showed me around the place and gave me some insight into my duties. Before I left, she showed me the schedule, and my first shift was on Tuesday. Mary told me I was put on Tuesday, Wednesday, and Thursday to help me get comfortable since they are slower days than the weekends.

I went home and tried on my uniform. I stood there in front of the full-length mirror. I smiled as  I saw myself in the uniform. The short black skirt helped accent my long legs, and my ass looked great in the skirt. The white top was low cut, and I showed a lot of cleavage with it. I thought, “Well, this should help with tips.”

Tuesday came, and I admit I was excited to show up for my first shift. I was working with Mary as she was going to train me for the first few shifts. Mary looked at me as I walked over to her. She whispered, “Do you remember when you told me you did not understand why you got the job, you thought you were too old?”

“Yes, I remember.”

“Well, look in the mirror. You look great, and you’re going to do great here.”

I smiled at her and thanked her. I have to confess it gave me some confidence as she took me over to my first table. I observed how she was so friendly with the people and interacted with them. Of course, she would flirt a little with the guys as they would with her, but she did not take it too far.

As the night went on, Mary had me serve my first table and just observed me. It was a table of four guys. They were very friendly, and my bubbling personality shined as I interacted with them. I have to admit it was fun. As they paid the bill, Mary came over to me to say. “I’m going to have to observe you. Those guys gave us a thirty-percent tip. You are a natural,”

I enjoyed the night and had a lot of fun meeting the new people I was working with and all the customers. Everyone seemed so nice. Every time I went to the bar for a drink order, a man was sitting at the bar and would have a comment directed toward me. I mentioned it to Mary, and she blew it off, telling me that is just Barry. He is a regular here. Barry is a nice guy and is harmless.

I felt a little more relaxed after that, and when I did go to the bar and Barry had a comment, I would have a rebuttal for him. However, he appeared to enjoy our flirting, and I admit I did.

Barry was a handsome man in his mid-twenties who dressed in some expensive clothes. However, he always dressed very nicely, and it was apparent that he also worked out often.

The following week went well, and I enjoyed working at Murphy’s. I felt more and more comfortable completing my duties and was more relaxed when serving customers without Mary being there. The one constant just about every night was Barry sitting at the bar.

Barry always had a few compliments for the servers and would be caught checking them out often. I have to admit I didn’t mind that. On the contrary, I was flattered that a guy who was ten to thirteen years my junior would still show some interest in me.

A few weeks passed, and I learned that Barry was quite a lovely man, and it didn’t help that he was good-looking. I was probably a little more invested than I should be. There were nights I would go home alone, reach into my nightstand, pull my vibrator out, and fantasize about being with Barry.

One night the place was dead. We had hardly any customers, and I only had one occupied table. As the night went on, there was no increase in customers, so my manager told me to leave early. He told me to wait until he found someone to walk out with me (Murphy’s had a rule that no server went out to her car without being escorted).

Barry spoke up and said that he was heading out after this drink. If I didn’t mind, I could be her escort. My manager looked at me for an answer. I looked at him and told him that would be fine with me.

I sat with Barry, waiting for him to finish his drink. We discussed many different things, but he couldn’t believe it when he found out I had two children in college. “Wait, you have two kids in college? Pardon me for asking, but how old are you?”

I had no problem telling him that I was forty-two. “Holy shit, I can’t fucking believe that. I thought you were in your late twenties.”

Barry was always one to flirt with the servers, but it was all fun and games. However, Barry seemed to change when he was talking to me at that moment. He seemed to have more sexual interest in me.

He finished his drink, and we left the bar as he walked me to my car. Barry walked me to the parking garage, where I parked on the third level. My car was the only one there. We strolled and talked about so many things. When we reached my car, we continued to speak, neither of us being in a hurry to leave. I have to admit I loved the interaction with another man. I felt like I had a purpose again. I didn’t even mind that Barry couldn’t take his eyes off my legs and tits. I was flattered since I got none of this at home anymore.

Barry took me in his arms and kissed me. His lips to mine were intoxicating. I softly moaned. I did not protest. It turned me on, and Barry could sense that it did. He held me tighter and kissed me more passionately. It was the first I was in a man’s arms in quite a long time. I didn’t want it to end. At that split moment, I decided I wanted more.

My hands moved up and down Barry, caressing his back and butt as they did. Barry didn’t waste any time as he caressed my body and our tongues explored each other’s mouths. Barry’s hand moved to my tits as he caressed them. Again, I didn’t protest. I just moaned louder. Instead, my hand moved between us as I stroked his hardening cock over his pants.

Getting brave, I unzipped his pants, grabbed his cock, and pulled it out of its prison. Our kiss continued as stroked his cock. His cock was an improvement from what I was used to having. I broke our kiss and smiled at Barry. Not saying a word, I squatted onto my heels. I looked into Barry’s eyes as I wrapped my lips around his cock. Taking him into my mouth until my lips were at his base. My lips held Barry’s cock at the bottom of his cock. I worked my tongue up and down his shaft and around the base, where my tongue darted out to lick his balls.

Barry’s hands moved to the back of my head, holding me there as he started thrusting in and out of my mouth. His cock slid over my lips faster as his cock disappeared into my mouth. His moans intensified. I could see he was getting close, and I wanted him. I wanted to feel his cock explode in my mouth and feed me his seed. Barry’s hands tightened on the back of my head, and with one last thrust, I could feel his cock shoot stream after stream of cum into my mouth. I sucked and swallowed every last drop of that huge load.

Just as we finished, there was a noise on the other end of the parking garage. It was some kids with their skateboards riding around the garage. I tucked his cock back in his pants and told him I better get home. Barry was stunned. “Wait, what about your needs? I want to make you as happy as you made me.”

“There are too many people around here, maybe another time.”

Barry asked if he could have my phone number so we could talk outside of the bar. I gave him my number, and he dialed it. My phone rang. He told me, “You have my number as well.”

He didn’t want to leave, but I pushed the issue and told him I did have to go home, but we could not tell anyone from the bar about this. He agreed to keep it our secret.

I got in my car and drove away. Driving home, I relieved the night and couldn’t believe what I had done. I didn’t have any guilt over it. Quite the opposite, I was so turned on that not only did I take control of my sexual frustrations, but I also was adventurous. I couldn’t believe I sucked a cock in public like that, where there was a chance of getting caught.

When I got home, hubby had already gone to work, so I went to bed. I got naked as I crawled into bed and thought about what I had just done. I was so excited that I reached into my nightstand and took out my vibrator. Before turning it on, my hands caressed my tits. I closed my eyes as I thought of Barry’s cock. I thought of it sliding in and out of my mouth. I wanted more of him and his cock deep in me.

I picked up the vibrator and no sooner turned it on when my phone rang. I couldn’t guess who would be calling me at night. I looked at my phone, and it was Barry. I answered it to hear Barry apologizing because I had to go home without satisfaction. You got me excited, and you are about to satisfy me now, I said with a chuckle. Barry asked what I meant. I went on to tell him how that was out of my character, but he was very excited. I couldn’t stop thinking about it on the way home. Now that I am home, I will be doing something about that.

Barry asked me what I meant. I didn’t answer; I just turned on my vibrator. You can hear the excitement in his voice once he realizes what I meant. “Oh My God, that is so hot.”

He then asked if I would face time with him so he could watch. I turned my camera on, as did Barry. His video popped up with him sitting on his sofa, still dressed as I was lying naked on my bed. “Wow, you are so hot. Oh god, I wish I was there right now.”

I didn’t waste any time. I turned my vibrator on as I spread open my legs and rubbed my vibe against my clit. My left hand moved back to my right tit as I caressed it, and my right hand stroked my vibe over my wet pussy. I watched as Barry undressed and lay on his bed as well. As I worked my vibe over my wet cunt, Barry’s hand slowly stroked his cock.

Our moans became louder as my legs opened wider and slid my vibe between my lips. “Yes, do it, fuck your pussy, my dick ramming in and out of you; oh yes, you feel so good.”

As he watched me, I worked my vibe faster and deeper into me. Barry watched my vibe disappear deep into my pussy. He kept cheering me on and watched as my hips raised, taking my vibe deep in me. Barry watched as I screamed, telling him how I was cumming. He couldn’t take it as his hand slid fast up and down his cock. Once I came, Barry exploded his cum shooting over a towel he had on his bed.

I had a wild orgasm, contributing to the fact that Barry was watching as I pleasured myself. Something that no one had ever seen me do before. We both remained naked in our beds as we continued to face time and talk. I felt like a teenager on her first date. I didn’t want it to end, and felt like I was on cloud nine being with Barry.

We both decided to hang up and sleep since morning would be here soon. However, before Barry hung up, he told me,” I almost forgot why I called in the first place.”

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“I asked why did he call.”

“He went on to ask me if I was working next Wednesday?”

“No, I am not. I have Wednesday and Thursday nights off. Why?”

“Well, next Wednesday, I am meeting with people after work for happy hour. Would you want to meet me at seven and I will take you to dinner? Our happy hour is right down the street from Bella Casa restaurant.” Bella Casa is an upscale restaurant that has had great reviews. I have always wanted to try it.

I smiled as I replied, “I would love to. I have always wanted to go there.”

“That is great. I will make reservations. We can meet outside the restaurant Wednesday at about six forty-five then.”

“It’s a date, I said; I will be there.”

Wednesday came, and I was so excited that I was like a kid waiting for Christmas. I was preparing for days. On Monday, I had my wax, so I was sure I would be nice and smooth for Barry. This morning, I went to get a mani-pedi and prepared the outfit I planned to wear.

I served dinner earlier than usual, hoping that hubby would eat and go to bed a little earlier than usual so I would have a little extra time to get ready.

It worked. Hubby ate and told me he was going to go to bed early. I could have screamed with joy hearing that. Instead, I finished cleaning up after dinner. By then, hubby was asleep. Once I finished cleaning up, I went upstairs to do my makeup and hair. I wanted everything to be perfect, so I payed great attention to detail.

I wore a short black pleated skirt, a tight-fitting black sweater that hugged my tits, and a pair of heeled sandals. I wore a sheer black lacey bra, but I did not wear any panties. I stood there looking in the mirror. Although my worst critic, I stood there smiling, thinking I looked hot.

I left the house and drove to the restaurant. I was a little early, so I stood outside the restaurant waiting for Barry. I kept looking in the big window on the storefront and couldn’t believe it was me. My confidence grew even more as guys would walk by, and I would catch them checking me out.

I spotted Barry walking toward me, and as he got closer, I could see the smile on his face and a hurry in his step. When he reached me, he was beaming and told me,” Wow, Dawn, you look gorgeous.”

I thanked him as he kissed me and escorted me into the restaurant. We were seated in a back corner, which was fantastic because we had a private table that allowed us to talk and enjoy public affection without everyone staring at us.

Dinner was delicious, and the company was even better. When we left the restaurant, Barry asked if I wanted to come back to his place for a drink. I thought, “Oh, I would bet there will be more than drinks. I would love to.”

Barry asked where I was parked, and I told him in the lot. He proposed that we take my car. His is parked in the garage at work and can come and get it tomorrow. I felt that would be the best thing for both of us, and I agreed. Once we got to my car, I asked him to drive since he knew where he was going. I was impressed as Barry opened the door for me. I sat, turned to get into the seat, and caught Barry checking my legs.

As he got in and started the car, I leaned over, kissed him on the face, and whispered in his ear, “So, are we going back to your place just for drinks?”

“Well, I hope not.”

“Neither do I,” I said as my handed rubbed his cock.

“Maybe, I should get the party started,” I said with a chuckle.

Barry started the car and pulled out of the garage. I continued to be next to him with my hand on his cock. I undid his zipper and pulled his dick out of his pants. I smiled at him and whispered, “I think I know just what you need.”

My head lowered into his lap as I wrapped my mouth around his dick and swallowed him into my mouth. As I bobbed my head up and down on his cock I felt Barry’s hand hike my skirt and caress my ass. Not only have I never given road head, but I also have never been this aggressive in going for what I wanted. Although, I have to admit I do enjoy this newfound confidence.

Barry’s moans got louder, and my head bobbed up and down on him faster. Finally, I felt Barry’s load flood my mouth with one loud grunt. I tightened my lips around his cock and sucked him to every drop.

My head moved up from Barry’s crotch. I kissed him again on the cheek and whispered in his ear. Best dessert ever.”

A few blocks later, we were pulling into the garage at Barry’s apartment. He parked in the garage, and we went to his apartment. I was taken aback as we entered. I knew Barry had a good job, but his apartment was terrific. He had a view of the city that was breathtaking.

As I walked to the window and looked out onto the city, I felt Barry’s hands take hold of me from behind as he kissed my neck. I smiled and turned my head to give him access to my neck before I turned, facing him.

“You didn’t tell me you have a view like this.”

Barry said, “The view just got much better,” before he kissed me.

Once he broke our kiss, he took me in his arms and carried me into his bedroom. My excitement was off the charts. I wanted him to lavish me all night long.

Barry lifted my sweater over my head and stood back, admiring my tits cupped in my bra. As he admired, I undid the buttons on his shirt and pulled it off his shoulder. His body was incredible. I leaned over and kissed him softly on his chest. As I did, his hands moved behind me and unclasped my bra. It fell off my arms and dropped to the floor. Standing there with my tits exposed to him, my hands went to my skirt, and I quickly undid it, and it fell to the floor. Barry did the same with his pants. We both stood in front of each other, totally naked as we couldn’t stop looking at each other’s naked bodies.

What seemed like forever but was in real life only a few short minutes, Barry moved to me, took me in his arms, and passionately kissed me. My body tingled as our naked bodies were tight together.

Once our kiss broke, Barry laid me on the bed and hovered over me. He leaned down and softly kissed me on the lips before moving down to my neck, then to my tits, where he kissed and licked each nipple before he sucked them. Barry’s mouth and hands were electrifying my body. I couldn’t believe how good I felt.

When Barry moved down and kissed my stomach, my breathing became shallow as my excitement built with anticipation. I watched as Barry continued lower. Finally, I opened my legs wider to give him access. Barry looked into my eyes as his tongue licked up my wet pussy and flickered it over my clit.

I moaned so loud I thought the neighbors might hear us. Barry sucked my clit into his mouth and sucked it as my hands moved behind his head as I ground my hips into his face. Then, when Barry slid a finger into me and massaged my particular little spot, I forgot how good it was to have my pussy licked in such a way. My body squirmed around the bed and into Barry’s face. I was building, and Barry knew it as his mouth and fingers did wonder on my pussy.

Barry moved his tongue off my clit and wiggled it into my pussy with his finger. He knew I was there as he darted that tongue in and out of me. I ground harder into his mouth. My moans became louder, and my breathing became heavier. Finally, my body tensed as I screamed to Barry, “I’MM CUMMING!”

Barry climbed up on top of me and kissed me. I could taste my pussy juices on his lips and tongue. I kissed Barry hard and passionately as our tongues went wild in each other’s mouths. Our hands explored each other’s bodies as we kissed. I could feel Barry’s hard cock resting on my stomach as our kiss continued.

Our kiss breaking, Barry told me that he wanted to be in me. Looking deep into his eyes, I whispered, “Yes, put it in me, put it deep. I want you to fuck me like I need to be.”

He reached over to a drawer in his nightstand and took out a condom. When I started to open it, I stopped him. “No, please don’t. We do not need it.”

Barry didn’t know that after our daughter was born, we both decided there would be no more kids, so I had my tubes tied.

Barry threw the condom back on the nightstand and smiled down at me. Lay there looking at him with my legs bent on the bed and my knees up. He crawled between my legs. Slowly with his dick in his hand, he guided it to my wet pussy. I smiled at him, “Yes, fuck me, baby.”

I closed my eyes and moaned as the tip of his dick opened and worked into me. “Oh, god, it feels better than I remember, I thought to myself.”

Barry thrust his cock in me, my hands caressing his back and butt. Then, finally, my hips started to rise to meet his thrust. Barry’s mouth met mine as we kissed hot and passionately. We moaned into each other’s mouths as he pounded deep into my pussy. The sound of our skin smashing into each other’s filled the room. I kept begging him for more.

Barry’s rhythm picked up. I knew he was getting close as I was on edge myself. Thrusting my hips higher into him, I felt him deeper. I was breathing heavier as I kept begging him for more. My body started to shake as my orgasm approached. Finally, my body tensed as my moans turned to screams, and I exploded on Barry’s cock.

As I rode my orgasm, Barry pounded harder and deeper into me. He was close. Finally, Barry yelled, “Dawn, I’m going to cum. Where do you want e to cum?”

“Cum in me I screamed. Fill my cunt with your hot thick creamy cum, baby. Give it all to me!”

I lay there limp as Barry lay next to me. We lay motionless for a while before I laid my head on his chest and started caressing his body. “Oh, that was nice, I moaned.”

“That’s for sure,” Barry responded.

We lay there touching and caressing each other as we talked. We discussed our likes, dislikes, our lives, and our fantasies. I don’t think I felt so close to a guy; I just fucked as I did right then and there.

We chatted for about forty-five minutes to an hour. My head was still lying on his chest with occasional strokes of his cock. It was showing signs of life again. As I stroked it, I could feel it getting harder in my hand. Finally, I moved my head off his chest and straddled him as I leaned down and kissed him.

As we passionately kissed, I sat on Barry and could feel his hard cock as my pussy took his cock between my labia. I ground down on his cock, rubbing it against my clit. My pussy was so wet. Finally, I broke our kiss and whispered in his ear, “Oh, baby, I want you. I want to feel you deep.”

I reached back, took hold of his cock, and hiked my hips until I felt his tip as my wet opening. I lowered onto his cock. Moaning as I felt him go deeper into me. Kissing Barry again as I moved my hips up and down on his cock. Riding harder and faster as our moans became louder as we moaned into each other’s mouths. Finally, I couldn’t get enough of Barry’s cock and rode him hard and faster, his dick deeper with every thrust. Riding Barry so hard, my tits were bouncing all over the place as I thrust down on his cock.

My body tensed as I clamped down on Barry’s cock. Finally, I exploded on his hard dick. Seconds later, Barry pushed up into me as. I felt his cock twitch and throb as he filled my cunt again with his hot thick creamy cum.

After cleaning up, we snuggled into each other. Then, finally, we fell asleep and slept for a few hours. Guess we both were so exhausted that we passed out.

I woke up and looked over at the clock on the nightstand. It read 3:00 AM. I knew I had to leave soon to be home before hubby got off work and came home. I wanted Barry again. So I slowly and quietly moved to Barry’s cock and started licking him. My lips wrapped around his cock as I sucked and licked him. His dick grew in my mouth as I sucked him.

Barry started squirming and moaning in his sleep. My mouth sucked him more, and suddenly Barry’s eyes opened. He looked confused before he realized what was happening. Taking my mouth off his dick, I smiled at him and said, “I am going to have to go soon, but I want some more of this cock before I left, so I thought I’d get you ready.”

Barry moved his hands down and started caressing my tits, then moved them lower as his finger slid into my slit. I was soaking wet already. My hips raised into his fingers. Oh god, I wanted him in me.

He positioned himself between my legs and went to enter me. I stopped him,” No, not that way. Fuck me, doggie style. I want you to take from behind.”

He moved off the bed and stood next to it. I quickly positioned myself on all fours with my knees on the edge of the bed. Barry stepped into me from behind and guided his cock to my wet opening. He felt his hands grab my hips tightly and buried his cock deep in me with one hard thrust.

I gasped loudly as his cock thrust deep into me. “Oh, God, your dick feels fantastic in me, fuck me, fuck me, hard baby!

I kept thrusting back to meet Barry’s cock with every inward thrust. Finally, I heard a loud smack. It took a quick second to feel the sting on my ass as Barry spanked me. “That’s it; take it, you slut. Take all my dick.”

I was not only shocked to feel the sting of the slap but to hear him call me a slut. “Yes, fuck me, fuck me like a dirty slut. Harder, deeper, give me all that cock.”

I begged for more. Barry pounded hard into my cunt. My body started to shake as I screamed at him. I was cumming. He continued pounding into me as I rode wave after wave of my orgasm.

Barry then took hold of me and flipped me onto my back. He continued to stand next to the bed. With my ass on the edge of the bed, Barry raised my legs, pushing them behind me with his hands, and opened them wide. He rammed his dick deep in me and continued to pound his cock hard and deep in me.

It was so hot looking up at Barry, his impressions as he fucked me, and watching his cock thrust in and out of me. I have never been fucked this hard and loved the pounding Barry gave me. His expression turned to one of determination when I saw his eyes close, and with one final hard thrust, he stayed buried in me as I felt his cock throb and filled me with his hot cum. Between the feel of Barry’s dick so deep in me and watching his face and cock ramming on and out of me, I screamed yet another time as I orgasmed.

After cleaning up, Barry and I said our goodbyes. I headed home before my husband arrived. As I drove home, I felt so satisfied. I felt like a woman again. At that point, I vowed that I was not returning to the way it was. Instead, I would do whatever I had to feel like I do right now.

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Written by Soccermom
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