Although, I must admit that being a bartender was pretty cool. What made the job so great was talking and getting to know those who sat at the bar and drank. Some were regulars, others were just passing through. Either way, I learned a lot about the people who sat at my bar. Sharon, for example, was a forty-something year old cougar who was divorced and a single mom to a daughter who had just graduated high school and would be starting college in the fall. Sharon was a nurse practitioner who worked the night shift. On her nights off, she would come and sit at my bar, drink her Chivas Regal on the rocks and hangout for a few hours.
One night after I got off work, I was walking out to my car and Sharon stepped out of her car and waved at me "Hi there," she said as she walked towards me.
"Oh, Hi," was all I could say. I was taken a bit by surprise.
"I was wondering if you would like to go get a drink. Considering we have wonderful conversation when I sit at your bar, I figured maybe we could continue some place where you could have a drink and not be working," she explained.
Wow! She was asking me out! This hot, classy older woman was asking me out. Given the shit I was having to put up with in the situation with my ex-girlfriend, someone asking me out felt really good and I wouldn't have to go back home right away. "Sure," I said with excitement, "Do you want me to follow you?"
"No, just hop in my car. I'll drive." She smiled.
I got in and she drove to a close-by tavern. We went in and sat at the bar. She ordered her Chivas Regal and I ordered a beer. She started talking about her daughter. "I'm out and about tonight because my daughter is having a party. And you know how that goes. Teenage girls don't want their parents around. She's having a sleepover with her girlfriends. It's a graduation/birthday party. She just turned eighteen." She explained.
Then she continued, "I bought them some alcohol as she promised me that everyone was sleeping over and no one would leave."
"That was cool of you," I stated.
"Yeah but I'm not sure it was the smartest decision, " she stated, "But I know she will be faced with the alcohol issue when she goes off to college, so I just want her to be prepared."
"She should be fine," I tried to make her feel better.
I could tell that she was stressed about her daughter going off to college. She took another drink of her Chivas. "She used to be a bookworm. Then she just blossomed. She was a late bloomer, I guess. All she used to do was study. She never had much of a social life. She never really dated. Then midway through her senior year, she just came into her own. She traded her glasses for contacts, let her hair grow out and her body really filled out. Now she's got a nice little figure and I see the way guys look at her when we are in public."
She took another drink and sighed, "She went from a dork to a hottie in six months." She bluntly stated.
At this point I really didn't know what to say, so I didn't say nothing. I just let Sharon continue. "I told her that she needed to get a job this summer. I'll pay for the tuition, she pays for her apartment. She didn't want to live on campus in a dorm, so if she wants an apartment she's going to have to pay for it."
She finished her drink and ordered another one then looked at me and smiled, "I'm so sorry. I'm just going off and ranting. Enough about my daughter. Lets talk about you. Are you dating anyone?" She asked rather directly.
I was caught off guard, but I told her about the situation I was in. She empathized with me but used it as an opportunity to flirt, "A young stud like you doesn't stay single for very long. I would think of it as an opportunity."
"For what?" I asked.
"To be free and do whatever you want to do with no strings attached," She smiled and said.
I was picking up on the insinuation, but I was still a bit unsure what to do. Then she looked at me, "So you want to get out of here and go some place that's a bit more quiet?" She asked.
I asked her what she had in mind, then she put it all on the table, "I gave a hotel room down the road. We can go back there and continue our conversation."
I was strangely excited by the invitation from this hot MILF. So I accepted. We drove to the hotel and as soon as we walked into the room, Sharon turned around, leaned in and kissed me. I reciprocated and next thing I knew, we were making out pretty hardcore. It was hot! This was not only the first woman I've been with other than my Ex in three years, but the first time with a woman so much older than me.
I am blessed with a nice ten inch cock and at that moment, it was hard as a rock and trying to break free. Sharon was all over me. We were still standing in the entrance of the room. She was whimpering slightly as we continued kissing and petting each other, "Every night I leave your bar, I go home and play with my vibrator, pretending that you are fucking me!" She confessed.
"Well, you don't have to pretend anymore," I whispered.
Just then she dropped to her knees, unbuttoned my jeans and pulled down the front letting my hard cock pop out. Her eyes widened, "Wow!" She exclaimed, "That's the most beautiful cock I have ever seen!"
She gripped my hard rod and put her mouth around the head and started sucking me as she stroked with her hand. She took more and more of my cock in her mouth with each stroke. Oh she was so good at sucking cock. As she sucked me, she stroked the shaft with one hand and massaged my balls with the other. She took my cock out of my mouth and started sucking my balls, taking turns with each one while her hand jerked my hard dick. Not wanting this to end too soon, I pulled her up from her knees. I then pulled her shirt off. She unclasped her bra springing free some nice, perky C-cup tits. She was taking off her pants and panties as I stepped out of my jeans that were around my ankles. Sharon laid on the bed and spread her legs, inviting me to her pussy. "I want to feel every inch of that cock inside of me!" she cooed as she rubbed her clit.
I crawled towards her on the bed and propped up on my knees. I teased her pussy with the head of my dick, parting her wet pussy lips. I rubbed my cock head against her clit a few times before sinking it into her already dripping wet hole. She gasped as I went in a few inches. "Ooh easy, Baby. Nice and slow," she cooed.
I worked my hips, giving her few more inches at a time until I was all the way in. Pulling her knees back a little, she spread her legs a bit more. She rubbed her clit as I slowly fucked her hot moist pussy, "Oh that's it. Give me all of that cock!" She moaned.
I stayed on my knees giving me full view of her hungry pussy devouring my cock. I would pull my dick out and tease her clit, then slide back in her hole balls deep. This drove her wild. "Oh you're such a tease." She whimpered, "You're going to make me cum if you keep doing that!"
I fucked her for few more minutes, then she flipped me over onto my back. "It's my turn to play," she said as she mounted my hard cock that was already glistening with her pussy juices. She pressed her hands on my stomach and looked down at me while she rode my dick. "Oh your cock is so big, I love the way it stretches my pussy out," she moaned as she kept slamming down on me.
She increased her pace as she started to cum, "Oh yes! Mmmm! Oh fuck! That's it! I'm going to cum," she squealed as she rode me.
I moved my hips in rhythm with hers until she exploded. She didn't slow down and continued to ride me. She came so hard, creaming all over my cock. I knew it wouldn't be long until I would cum, so I flipped her back over on her back, shoved my cock all the way in her pussy. I could feel my orgasm building. So could she, "Oh yeah, you're going to cum aren't you?" She taunted.
I didn't respond, I only kept pounding my cock into her. "I want you to cum all over my tits," She instructed.
Just before I exploded, I pulled my cock out if her box and she immediately grabbed it and jerked me off. My cock erupted in ropes and ropes of cum that squirted all over her tits and stomach. She stroked me until there was nothing left. Then she pulled me close and took my cock into her mouth and sucked & licked me clean. I fell to the side of her and laid motionless on the bed trying to catch my breath. Then, without realizing it, I drifted off to sleep. I awoke the next morning alone in the bed and the hotel room. Sharon had left. No note, no phone number or anything. So, I got out of bed, got dressed and called a cab to take me back to my car.
Two weeks had gone by and I had not seen nor heard from Sharon. Oh, well. It really didn't bother me too much. Maybe she was just a cougar on the prowl and got what she wanted. I had no expectation of a dating relationship with her. Besides, I had my sight set on this hot chick that recently started waiting tables at the restaurant where I worked. Damn, she was hot. She was about five feet, five inches tall with long brown hair, a rocking body, perky tits and the perfect ass! Her name was Beth. Apparently, I wasn't the only guy there who had similar thoughts about her. Just about all the guys had asked her out, except for me, and she turned all of them down. They started calling her the "Ice Queen."
One night I was hanging out at the restaurant on my night off. I was sitting at the bar having a few beers when Beth came up to the bar and slammed her servers apron and notepad down. She was obviously pissed off about something. "Is everything OK?" I asked.
She shot me an irritated look and snapped, "No, everything is not OK! Since it's a slow night, I just got sent home and I don't think I have even twenty dollars in my pocket! How in the hell am I supposed to save up for school if I don't even make twenty dollars in a shift?!"
"Yeah, it's that time if year where everybody is saving for school, so you're not alone," I said, smiling at her.
She didn't smile back, "Is that supposed to make me feel better?" She snapped again.
I just shrugged. She pulled out her cell phone and called somebody who didn't answer and she hung up. "Great!" She said sarcastically to herself then noticed me still looking at her.
"What?" She snapped a third time.
I finished off my beer then stood up from the bar, "Come on. I'll buy you dinner," I said a I started for the door.
She was taken aback by that. "Are you seriously asking me out on a date?" she asked, still with the attitude.
"I'm offering to buy you dinner. You can call it whatever in the hell you want," I returned.
"I'm not looking for a boyfriend," she stated, wondering if that would change my mind.
"Who said I was looking for a girlfriend, especially one that will going off to college in a few months?" I retorted,"Look, I'm going across the street to that restaurant over there and getting me some dinner. You are more than welcome to join me if you want. If you don't, no big deal."
And I turned towards the door and walked away. I was almost to the door when I heard her say, "Alright, I'll join you."
We walked across the street, went in to the restaurant and sat at a nice booth. "Look, I'm sorry for being such a bitch, but since I've started waiting tables, I'm constantly being asked out by the guys. I just want to do my job and go home," she explained.
"You should feel flattered," I smiled.
She gave slight smile, "I am, I guess. But why get involved when I'm leaving for school in a few months?"
"You can have fun without getting involved," I stated.
We ordered something to eat and we had a great conversation. She told me that she was going to Georgia Southern University and couldn't wait. She picked my brain about college life after I told her hat I graduated a year ago. I also told her about my internship, then getting laid off, which led me to my current job of bar tending. The Ice Queen was warming up. We talked and laughed and talked some more. The restaurant was closing but we weren't ready for the evening to be over. We were out in the parking lot and she looked at me, "I'd love to buy you a drink but I'm only eighteen so I can't get in to any bars," she said.
Before I could respond, she yelled, "Hey, I have an idea!" I could practically see the light bulb go off in her head,"Come over to my house. I have some beer and liquor, so we both can have a drink," she suggested rather excitedly.
"Don't you live with your parents?" I asked.
"No one's home tonight," she said.
I accepted the invitation and followed her to her house. It was dark inside then Beth turned on some lights. She grabbed two beers and tossed one to me. "So where is everybody?" I asked.
"My mom's at work and my dad, well. . . He's not in the picture," she explained, taking a sip of her beer.
I was a little surprised to see that Beth liked beer. Most girls her age don't. They would rather have a wine cooler or some fruity drink. I watched her as she drank the brew. She noticed me watching her and said, "My mom lets me drink as long as I do it in the house and I don't drive. That's cool, I guess."
I nodded and she continued, "My mom is obsessed with making sure I'm prepared for the types of situations I will be exposed to in college, like alcohol for instance."
"That's smart, actually," I said, not making the connection.
"Yes, but she can't possibly prepare me for every single situation I might face," she stated.
She had a point. We moved into the living room and I sat down on the couch. Beth plopped down beside me. We talked more about college life. We were on our third beer when the tone of the conversation turned flirtatious. She gave me a smile then stared at me for a few seconds as if something was on her mind. "What?" I asked.
Her smile got brighter and she asked, "So, what's YOUR story? Do you have a girlfriend or dating anyone?"
I told her no and that I just got out of a three year relationship that didn't end on the best terms. However, I did not tell her about still living with my Ex.
