I [M] had sex with the [F]airy bartender (long)

Hello everyone, I know it’s been a while since my last story time. Work has been… let’s just say special. Here’s one more of my between marriages tales.

The season was beginning to slow down at work and while my company had no intentions of doing lay offs, hours had been cut. I found myself in need of supplemental income. I had a friend who said the bar he worked at was looking for a gimmick to keep people coming in the doors. I suggested a weekly music night.

His boss turned that idea down. But a week later, I get a call asking if I wanted to mc an open mic night. One night was all it took and now I had an extra weekly check until Christmas. Things were good. I got to tell jokes, play music, and listen to all the local talent. I got along with all the staff and soon it became the highlight of my week.

There was one bartender there who I got along with exceedingly well. Long legs, soft freckled skin, and hair the color of sunrise. For the sake of this story (and the fact that I’m listening to an 80’s playlist) we’ll call her Eileen.

Eileen was a joy to be around. Her bubbly personality and flirty comments always left a smile. She had a mild Irish accent that would become more pronounced the more tired she was or the more drunk she was. But the most fun thing about her was the fact that she would come to work in a different halloween costume each shift that October.

We got to see the busty bar wench, the lusty witch of the east, and the best one of them all, which is where the sexy stuff starts.

October 30th. I’m setting up my equipment for the nights festivities. In she walks in her street clothes shouting her greetings to me on her way to the employee bathrooms. My friend there bartender asks me why I haven’t asked Eileen out yet. I’m about to answer when she steps back into the room and my brain melts. There she is… in the tightest tinkerbell costume that exists. Complete with a little set of wings and breasts that are fighting to escape.

Now, I’m not usually one for the Disney costumes, but seeing her made me super happy that my costume was “super tall Kevin Smith.”  Baggy jeans and a trench coat hide erections very effectively.

I do my first set, introduce the next acts, and proceed to step out into the cool autumn air for a smoke. Eileen follows me out and bums one from me. “You look beautiful tonight” I tell her. She smiles and thanks me.

“What are ya doing after this? ” she asks me. I try not to stare at the glorious cleavage in front of me. “I didn’t really make plans tonight.” She smiles and takes a drag. “How about ya coming over and watching some scary movies with me?” I think I answered yes a little too quickly.  “Wonderful,” she said, “I didn’t want to do it by myself.”

The rest of the night why by painfully slow. Finally, it was time to pack up and head out. Eileen, still in her costume, collected her things and followed me to my truck. We got to her apartment and I helped her carry her stuff in. I figured she’d go and change, but instead she sat down on the couch and started asking me which movie to start with. We settled on the nightmare series. About halfway though Elm street 2, I could tell she was losing interest in the movie. I, for one, had not been watching the movie at all. How could I with this gorgeous ginger in a fairy costume beside me.

“So,” she started, “how long has it been?” She knew I had been married young, and divorced. We had talked on the matter of me trying to date. I even told her about the very short lived relationship right after my divorce. “How long?” I answered her question with a question, I know it’s lame. “How long has it been since you’ve been out on a date?” I told her almost a year and she laughed. “Ya mean to tell me ya haven’t been out with a woman for almost a year, what about all those ladies I see flirting with you at the bar?”

“It’s just not been that important, I’ve got my job, the bar, my kids.” She had begun to look at me like I had three eyes. “Well, what about sex?  “What about it?” I asked ” yeah i miss it, but I don’t have to have it.

“Oh, I have got to do something about this.” She turned off the tv. “Kiss me.”

“Wait, what?” I stammer. “Ya heard me, it’s been too long since you had any and frankly, I’ve been looking for an excuse. Now kiss me!”

With that, I pull her in and kiss her like I’m going to war. Her soft lips on mine, our tongues gently meeting at first then filling each other’s mouths. She climbed on to my lap and I began to kiss down her neck and collar bone. “Yeah, that’s nice.” She says. I grab her hips as she begins to grind on me. I continue to kiss just above her cleavage. She guides my hands from her hips to her back, “help me get out of this.” I unzip the back of her costume and help her pull it down. With her full and beautiful tits now exposed, I began to kiss around her pink nipples. She grabbed the back of my head and moaned as I nibbled and sucked each one.

She pulled away and stood up. I leaned in to pull her dress the rest of the way off. I slowly kissed my way down her belly as the fabric fell revealing a lovely red landing strip. I kept kissing the soft skin as my fingers gently grazed her lips. She sighed and moaned as my finger tips found her clit and I began to massage her. The bite of her lip telling me everything I needed to know. Her body began to tremble as I found my way inside her. She rocked her hips to match the motion of my hand. Looking up at her beautiful face, I pumped my fingers in and out until she couldn’t stand it anymore. She put her leg up on the couch beside me, giving me a better view of her glistening pussy. She pulled my head closer, my tongue found its way to her throbbing clit and I lapped up every bit as my fingers and tongue helped her to a mild orgasm. I removed my fingers painfully slow as she pushed me back.

Though wispy breaths, she said,  “if I knew ya could do that, this would have happened sooner.” She sank back down on my lap and kissed me with renewed vigor. She reached and helped me take my shirt off then slid down to the floor in front of me. “Your turn now” she smiled. In a quick motion, she unbuckled my belt and pulled my jeans completely off. My cock already at full mast, she took it in her hand and gently stroked me. She kissed the tip and licked all around the swollen head before taking me into her mouth. She began to bob up and down gently. Her lips glided along my shaft leaving rings of lipstick. Her hand going from stroking me to lightly massaging my balls. I almost came just from the sight of it.

She knew I was getting close, so she climbed back on top of me and guided my cock in place. “What about a…” I began to say.  “I’m on the pill.” She reassured me. (Truth be told, a quick procedure I had already took away that risk. I’m used to being responsible.) She started to rock her hips slowly until I was all the way in. Being inside her pussy was amazing. I reached back to grab her ass as she began to bounce on my lap. “Kiss my tits again.” I had no trouble with that request. My lips went back and forth to each nipple. “Oh god,” she screamed as her insides suddenly gripped my cock. I pulled her close to me and buried my face between her breast as she came. My cock began to twitch and I let loose, completely filling her already drenched pussy.

We both lied there, unable to move or even think. She slowly climbed off of me and lied back down on my belly. “How was that?” She asked. I couldn’t even speak at that moment. “Looks like we made quite the mess.” She went down on me one last time and, god help me, I yelped from the post sex sensitivity. She burst into laughter with my cock still in her mouth and that’s how my halloween started that year.

Source: reddit.com/r/gonewildstories/comments/j7jrs9/i_m_had_sex_with_the_fairy_bartender_long