Brunette Bartender Emily

Author's Note: This Emily is NOT the same Emily as the stories about "Little Red Emily." This is a similarly petite Emily but she's a brunette and is one of the bartenders at a local chain restaurant. This is a story about a swinger couple who have sex outside their marriage. If that's not your thing, move on.

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My wife Dana and I have a history of giving each other sexual gifts for our birthdays and, on rare occasion, anniversary. We've been in the swinger lifestyle for a little more than 15 years and I've always enjoyed watching her give and receive pleasure. When she realized she enjoyed seeing me do the same, we searched out and found playmates we could enjoy. One of the things we've realized we enjoy most is when the playmates are very different from us. For instance, Dana is about five feet six inches tall and a very curvy brunette with a 40D chest. She keeps her pussy trimmed but never shaved. When she finds playmates for me who are smaller, built differently, maybe keep their pussy shaved, etc. the difference can add to the fun. That was the case when she gave me a redheaded young lady named Emily who was barely five feet tall, small framed, shaved smooth and had barely a B-cup chest. (You can read about that in the Little Red Emily stories).

Recently we were out at a local restaurant, one of the larger chains that are designed to mimic the highway-side roadhouses you can find coast to coast. The first night we were there for dinner and I saw Emily I commented to my wife how attractive the petite brunette bartender was. Her hair was long and pulled back in a ponytail, her jeans fit her perfectly and showed off her nicely rounded ass very well. I guessed her to be about five feet one inches tall and her wide mouth smiled easily. Emily was very friendly, standing and talking with us while business was slow.

Every few weeks we'd visit the place for dinner, sometimes sitting in a booth and sometimes sitting at the bar. Probably about 2/3 of the time we were there we ended up being served by Emily. It got to the point where she remembered our names and would ask us about work, travel, life, etc. when we were there. We learned about her ex-husband, her current fiancé and her daughter. I couldn't tell for sure but I felt like Emily was giving off that, "we could have a lot of fun" vibe. Dana said she thought so too but there was little that could be done about it in the middle of a restaurant and neither of us wanted to breach the subject, risking offending or angering a young lady we'd come to like quite a bit.

Then the night came along when Dana was on travel for work and I didn't feel like cooking dinner for myself. I knew it was an evening that Emily might be working so I decided to go get dinner, probably sitting at the bar, and hopefully able to see, talk to and/or flirt with Emily. I texted Dana to let her know my plans and she jokingly sent back, "Don't do anything I wouldn't approve of."

I replied, "If I do, I'll take pictures," and got some laughing emojis back.

When I got to the restaurant I was pleased to see that it was being a relatively slow evening and there were plenty of seats available at the bar. Emily was the lead bartender and she smiled when she saw me taking a seat. She looked around briefly and then looked at me. "No wife tonight?" she asked.

"Dana's on travel," I replied. "This evening you get me all to yourself." It was the kind of flirty comment that I knew wouldn't offend her, but she could take it as a joke... or not.

Her reply of, "Oh, goodie," was said with a smile and maybe just a hint of sarcasm. It put me off just enough that I wasn't sure I should pursue any more flirtatious remarks. "Where'd she have to go?" Emily asked.

"Philadelphia," I replied and then added, "for a few days."

"Interesting," she said. "That's where my fiancé is this week too."

I couldn't resist the sexual innuendo potential so I said, "Uh, oh... you don't think they set this up? Do we need to worry about them being up there together?"

Emily had a plethora of responses to pick from, running the gamut from serious to joking to flirtatious. What she said was, "Would either of us really care?"

To be honest, it kind of surprised me. Her entire demeanor said she really didn't care what her fiancé was doing or with whom. Past conversations had pretty much let Emily know that Dana and I had an open marriage as we regularly joked about dating or playing with others. I chose to not treat her question as rhetorical. "I wouldn't care," I said seriously. "If Dana found someone she enjoyed spending time with while she's up there, I'd probably get off hearing about it."

That brought a mild look of shock to Emily's face but the smile quickly returned. "Would Dana feel the same way about you finding someone to enjoy time with while she's gone?"

"Without a doubt," I answered, "since she told me to 'have fun' while she was away."

Once again there was that slight look of shock on Emily's face. "And you think she meant it that way?"

I knew it was time to be straight forward. I looked around to make sure there wasn't anyone listening in on our conversation. "Emily, Dana and I have been swingers for over 15 years now. I know exactly what she meant, and as long as I don't hide anything from her, I'm free to do whatever I want with whoever I want." She looked only mildly surprised as I added, "And she enjoys that same freedom... but she hasn't on this trip yet or she'd have either told me about it or sent me pictures." I figured if I was going to risk shocking her, I might as well not hold back. Her response wasn't exactly what I was expecting, but it was welcome.

"That is so fucking hot," she said, and I swear her eyes glazed over with desire. "You let her fuck other guys and she sends you pictures?"

"I not only let her fuck other guys," I replied, "but it was my suggestion. I love watching her let go to her slut side and enjoy all the pleasures she can get or give. And yes... one rule we have is that she HAS to send me a picture of her naked, taken by her playmate, before they fuck. If she can't, I get pictures afterward. But either way I know about it beforehand or immediately after. We never hide anything from each other."

Emily leaned over the bar just a little bit and looked around before meeting my eyes. "So if I invited you in the back for some quick fun, you'd tell her about it?"

I looked at Emily in a new light. There was the real possibility I would get to play with her and my cock was nearly rock hard at the thought. "What I'd probably do," I said, sounding as serious as I could, "is take a picture of your pussy riding my cock and send that to her inviting her to 'guess who'."

Her entire demeanor changed, as if she'd been hit with an invisible hammer. She went from flirting bartender to woman about to get fucked like a wave of energy flowed through her. "Give me three minutes," she said, "and then meet me by the office door behind the bathrooms." I nodded and she walked away toward the kitchen. About a minute later one of the servers showed up behind the bar and I knew she was the temporary fill in. She checked that the few of us sitting at the bar didn't need anything and then she leaned against one of the coolers to watch one of the several TVs that were on. I waited another minute and then got off my stool to head to the bathrooms. As I approached the men's room, the door at the end of the hallway opened. Emily was standing there with a big smile on her face, her work apron gone and several buttons on her shirt undone. She held the door open for me and I stepped through with a big smile. She closed it behind me and I heard her slide the bolt into place.

"I'll only say this one time," I said as I turned to face her, "I don't want to get you in trouble with your job, so we can always do this another place, another time."

She took me by the hand and led me over to the desk which had little on it beyond a letter tray and a blotter. "I won't get in trouble and I want to do this now."

She stopped at the desk, turned to perch her butt on it and pulled me to her. Her legs were slightly spread, and she held my hips as I put my hands on her shoulders. On the one hand I knew we didn't have a lot of time, but on the other hand I didn't want to be overly aggressive with Emily. I wanted to let her take this at her own pace of comfort. She took her hands off my hips and I felt her find my cell phone, taking it out of my pocket and putting it on the desk before she moved her hands to undo my belt, before unbuttoning and unzipping my jeans. That gave me a hint as to her pace. I reached down and started to unbutton her shirt more but she said, "No, just my jeans." Nodding I stepped back just a little and unsnapped and unzipper her jeans. She had gotten mine undone and was pushing them down my hips. She was nice enough to be careful as my jeans and underwear moved over my stiff dick, not dragging on it too much. I stepped back a little more, even as her little hands reached for my length, grasping and stroking it. She stood up so I could push her jeans off and she wiggled her hips to help as I pushed them down over her hips and butt, making sure they were well down past her thighs before I let them go.

Emily bent over to push her jeans the rest of the way off and took my cock in her mouth as she did so. We hadn't so much as kissed even though our passion was obvious. She wanted to get fucked and I was eager to feel her tight wet pussy around my cock... to be buried in her balls deep. For the few moments it took her to push her jeans off both feet, kicking off her tennis shoes as she did so, she kept my cock in her mouth, working slightly up and down, swirling her tongue around the swollen head. When her jeans were off, she stood up, leaving my now spit-slicked cock bouncing in the cool air.

She moved back so she was sitting on the desk and spread her legs open for me. She reached up to put her hands around my neck and pulled my face to hers for a kiss. As our lips met and our tongues tasted each other, I reached a hand between her spread thighs to feel her wetness... and wet she was. Her pussy was soaked and felt pretty ready for some cock. One of her hands moved to my length, stroking it and then pulling it toward her sex. I broke our kiss long enough to ask, "Condom?" She shook her head no and kept pulling my cock toward her, lifting her legs and spreading herself open farther for me.

I moved closer and the swollen knob of my cock touched her wetness, moving up and down as she moved it with her hand. I let her determine how things would proceed, at what pace, and just enjoyed the sensation as she kept rubbing my cockhead up and down her slit. It was so wet I wondered if she was puddling on the desk blotter. Then I felt her line my cock up with her hot opening and pull me in. I did as she silently directed, kissing her as my manhood just barely entered her pussy. Her hand left my length and went to my hip, pulling me toward her. I gave her what she wanted and pushed my shaft into her, stopping when I met resistance, pulling out slightly and then pushing back in. About three strokes later I had my length buried in her wetness and we were grinding together.

As we continued to kiss I began fucking her with long slow strokes, pulling my cock out until only the head remained in her and then pushing back in until my balls were pushed up against her asshole. As I pulled out on one stroke she broke our kiss and reached over to pick up my phone. Handing it to me she said, "Take that picture... let me see you send it to Dana." I think she got off on the idea even more than Dana or I did.

With my cock positioned about half way into her pussy I took a couple pictures. Emily's creamy white pussy juice was easily visible on my shaft and her neatly shaven lips were slightly red and swollen. I started stroking shallow again as I picked the best picture, prepped a text to Dana that said, "Guess whose pussy is enjoying my cock?", attached the picture and then showed it to Emily before I hit SEND.

I set the phone down and went back to focusing on the fuck, and it was quite enjoyable. Emily's pussy was tighter than Dana's, but that wasn't a surprise. Dana had years more experience at sex and, no doubt, had enjoyed a wider variety of cocks than Emily had. I increased the speed of my strokes as Emily and I started kissing again, finally getting to the point where I was slamming my cock into her, listening to our flesh slap as we moved together in the most ancient sexual dance.

My phone chirped beside us and I slowed only enough to show Emily the message from Dana. It said, "Fuck her good and tell me about it later!"

"Oh my god," Emily said with a moan. She started pulling on me and humping her hips at me. "Do it... do what she said... fuck me good and tell her about it later!"

Putting my hands on her hips I did as both my wife and my playmate had said. I fucked her as hard as I could, battering the petite woman's sex as I plunged my full length in and out of her as hard as I could. Emily came twice like that, each time having to bite back her sounds of pleasure. After her second orgasm passed she pushed me away, turned around and bent over the desk, presenting her ass to me. It was beautiful and sexy but I didn't think she was asking me to take her backdoor. She merely wanted to be fucked from behind.

I lined my cock back up, slid into her wetness, grabbed her hips and started fucking her hard again. I wanted my orgasm and knew I wasn't being selfish. Emily had meant for this to be a quicky and it was probably already taking longer than she had originally expected. "Fuck me," I heard her say in a whimper. "Fuck me and fill me," she said with a whine.

I increased my pace and the ferocity of my pounding. Her ass cheeks started to look like she'd been spanked but it was from my pelvis and lower abdomen slapping against her as I gave her the hardest fucking I could manage. Somewhere in the back of my head I worried about bruising her where the front of her legs and hips were against the hard desk, but I figured she'd say something if it mattered... so I just kept fucking.

She came again before I got mine and when I felt my balls start to tighten I moaned out, "Oh, baby... I'm gonna cum."

"Do it," she hissed back at me, humping her hips with more vigor, keeping me moving within her even as I tried to slow the pace. "Fuck that cum into me."

That answered any question I might have had about whether or not I could cum in her, so when my orgasm set in I pulled her hips back as hard as I could, pushed my hips forward with equal strength and kept my full length buried as my cock spit hot thick ropes of my cum into her. I moved just enough to keep the orgasm at its peak for as long as possible, reveling in the pleasure as I felt my cock twitch in the final spasms of my climax.

When I was done I pulled my softening cock out of her as she reached down between her legs, cupping her hand under her sex to catch my cum as it ran out of her. I looked around for anything I could give her to catch it... a towel, napkins, anything... but saw nothing. I backed up another few steps and pulled my pants up. Yeah, I knew my sticky cock would end up stuck to my underwear when my cum and her juice dried, but I wasn't about to complain. It was well worth it.

Squatting where she'd turned next to the desk, she kept her hand cupped under her sex and looked up at me with a smile. "Wow..." she said, "That was probably the best quicky I've ever had. We'll have to do it again sometime."

I chuckled as I zipped up my jeans and got them buttoned before fixing my belt. "Oh maybe not a quicky," I said. "It can be even more fun with a bed and plenty of time."

"Definitely," she said and then she shocked me by putting her cum-filled hand to her mouth. She licked and sucked my cum out of her hand and then put it between her legs again. As I watched she stuck two fingers into her sex, stirred them a little and then pulled them out, raised them to her mouth and sucked them clean. When she was done, having seen the look on my face she said, "It's better than having the smear in my panties for the rest of my shift... and besides, it tastes good."

I smiled and waited as she stood up and got herself put back together. "You go out first," she said, "and I'll follow you in a few minutes." All total, I don't guess we'd been in the office 15 minutes. I did as she said and five minutes later I was back on my barstool and she was back behind the bar. For the most part, neither of us looked like anything had happened at all.

I ordered another beer and when it was done, I paid for my tab. As she brought me my receipt Emily said, "I get off in two hours. Should I come over then?"