Eddies Sexual Adventures

"UHHHNNN....OMG!!! Cum on my ass!!!" Heather squealed as Eddie pulled out his cock and shot a copious amount of cum all over ass. He noticed that the first blast had went the furthest which got on the costume Heather was wearing which led to this unexpected encounter after they had closed the costume store. To be fair, it was not completely unexpected. There was sexual tension building between the two over the last few weeks. Eddie was caught off guard when he walked to the back of the store and found Heather sitting on top of the dressing room counter wearing a naughty schoolgirl outfit. The sight of her was incredible. The white blouse tied up in a knot revealing her naval and allowing enough buttons undone to give her perky tits a bit of cleavage. She uncrossed her legs revealing no panties underneath her skirt with only the knee-high stockings and little black shoes to complete the ensemble. Never mind the fact that her petite 5'4" frame allowed her to rock the look in a way that really sold the look. She opted to wear her own glasses instead of the costume pair which was a great choice since she looked sexy in them anyway.

The next 30 minutes were a blur for Eddie. He had been wanting to hook up with Heather for the longest time and he was finally doing it; in the workplace no less. Heather took off the blouse to examine the load of cum that had gotten on the back of it. Her tits were incredible and her tattoos between them and her neck looked a lot more sexier. "What do you think? Shrinkage?" Heather smiled as Eddie laughed. "Yeah, we might want to dispose that ourselves," came the reply. Heather found her t-shirt and put it on before locating her panties and sliding them on under her skirt. "I guess you're keeping that," Eddie said as she finished collecting her things. "Of course, it would be a waste of a perfectly good "fuck me skirt," Heather replied. Eddie couldn't argue her logic.

They exited the store and after it was locked up, they shared a deep, passionate kiss. "Call me sometime," Heather said as she turned to her car. "Wait, you're not showing up tomorrow?" Heather looked back with a grin. "Nope. I don't want things to get awkward." Eddie couldn't help but smile and shake his head. She had a point. The store was done for the season and that night was the last of the discounted sales before the remaining merchandise was packaged for pickup. He would have probably opted out himself, but he liked working and he liked being paid. To say that he would be leaving that place with a bang would be an understatement.

ONE WEEK LATER

Eddie found himself at a local dive bar called After Hours. He had found it by happenstance when he was driving around late one night after finishing his last shift with the store. The bar was unique in a way that rivaled most other bars. It had a good central location and it was common to see hookers, strippers and bartenders from other establishments show up just to blow off some steam and be a customer after serving others for several hours.

"What are you drinking, honey?" came the question from Mia the bartender.

"Bud. Draft," Eddie responded.

Mia was the owner of the After Hours bar. She had acquired it after her dad passed away and left it to her in his will. She made a few changes to the place which included changing the hours to really capture the feel of an after hours establishment. She had a small staff of beautiful servers who took care of the room but she was in charge of the bar. It was her baby.

Mia was young but driven. She had just turned 23 and had really made a name for herself among the nightlife crowd, especially those who stayed out late. She was incredibly attractive too. She had shoulder-length hair that was fiery red and her freckles she sported on her shoulders served as her beauty marks. She was 5'6 with a noticeably fit body. Her breasts and ass were her signature assets. Mia preferred wearing revealing outfits while she worked. She claimed that it was easier to stay cool that way. The tip jar behind her suggested otherwise. On this night, she was wearing a tube top that was probably a bit small but she wanted to make her breasts appear bigger. She wasn't shy about her body. The top left little to the imagination and one could see her nipples and her piercings. She completed the look with a pair of short shorts that showed off her curvy ass.

"So, what's up with you tonight?" Mia inquired as she handed him a beer. "Notta, getting ready to start this new job next week," Eddie said, referring to a marketing job he had landed earlier in the week.

"Is that the one you were talking about with the evening hours?" Mia asked.

"Yeah. Monday through Friday 4-midnight. Not a bad gig," Eddie said with enthusiasm.

Mia smiled. "Well, that allows you to keep coming back to see me afterwards, right?"

Eddied agreed. The bar was closed on Monday and Tuesdays but with the 6PM to 6AM hours the rest of the week, it was an ideal stop after working eight hours. Eddie continued with his thoughts until Mia snapped him back to reality.

"Did you ever talk to that girl again?" Eddie had told Mia about his carnal rendezvous with Heather during one of his first visits and for the life of him could not figure out why. Mia appeared to be a sexual person herself and enjoyed stories like that. All Eddie knew was that he rarely spoke to a female about his sexual exploits.

"I've texted her a couple of times. She's been busy," Eddie wasn't too concerned about it. After all, he didn't want any attachments and casual sex was fine by him. He was teased by her however when she responded to a text with a pic of her in the skirt and her arm covering her breasts.

Mia nodded and wiped down the bar before taking an order for a nearby table. Cari came over next to Eddie to pick up the tray of drinks for her table. "Hiya," she beamed as she picked up the tray. Cari was one of two servers on Mia's staff. She had a bubbly, girl-next-door personality and was very sweet. Cari had been a stripper after starting college to pay her way but upon learning about the job at After Hours, she applied and ultimately quit the strip joint. It was reasonable to assume that grinding on a bunch of random dudes was not the way to go.

"Hey, get your hands off me!" Cari yelled.

Eddie turned around to see a couple of guys taking terms groping her ass as she served them her drinks. "Oh come on darlin'...you know you like it." "No...no I don't," Cari responded, visibly shaken. The two drunks would not relent. "Don't be like that. I remember seeing you at Club Paradise and you had no problem with being felt up."

It was at this time Eddie got up and approached the table. "The young lady said no." The drunks looked at him and laughed. "Oh...is this your girlfriend? One of the men asked mockingly. "No, but I'm not going to sit here and allow you to disrespect someone like that." They both stood up in a confrontational manner. "Boy, you done made a big mistake," The drunk closest to him took a swing which was avoided. Eddie countered and dropped him with a right hook. The other drunk attempted to hit Eddie with a beer bottle but his arm was stopped by Byron, the bouncer. Byron was a big hulking black man who dwarfed many a man when he stood up. This time was no exception. Byron put the other drunk in an arm-bar and tossed him out the door. He came back for the one still laid out on the floor and tossed him out too.

"Are you alright?" Eddie asked Cari. The young waitress evaluated her condition, still visibly shaken. "Yeah, I'll be fine," she said in a low voice.

Mia took Cari to the back while the second half of the staff, Leah, cleaned up the mess. Leah was slender with long legs, an olive complexion and long dark hair. She was personable but Eddie couldn't get a read on her. A lot of things about her suggested she was a lesbian but he wasn't sure.

Byron came back inside and looked at Eddie. "Am I gonna have a problem with you?" Leah interjected, "Leave him alone B, he stood up for her." Eddie gave a half smile before thanking him for keeping his head from being introduced to a bottle. "No big deal man," was the bouncer's response.

Eddie pulled out some cash and paid his tab before exiting. He had to get some ice for his hand and the only place he wanted to be treated for it was at home.

CHRISTMAS

The day before Christmas, Eddie walked into After Hours and took a seat at the bar. Mia smiled at him and poured him a beer just as he sat down. With the holidays in full swing, the bar was going to observe special hours so it would be closed in the middle of the week. Mia was definitely dressed for the occasion as she was rocking out a naughty Mrs. Claus outfit. It was form-fitting and revealing; Eddie was noticing the stares and open mouths of some of the guys at the bar.

"Hiya handsome!" Cari came up from behind him smiling brightly. She was small with blonde hair and perky tits and a round ass that were all being enhanced with the elf costume she was wearing. "Hey, Cari. Looks like you're Santa's little helper." Cari smiled and coyly asked what gave it away. Eddie just winked at her. "Hey, Mia is letting me off early so I figured I would sit and drink with you." Eddie chuckled. "Sure, I'd love that." Cari squealed with delight before returning to the floor.

"She's really smitten by you," Mia said as Eddie turned back to the bar. "No one has ever stood up for her like that and quite frankly, I'm surprised you two haven't hooked up yet." Eddie just shook his head. "You're telling me you wouldn't want to sleep with her?" Mia looked shocked. Eddie just smiled and said, "It's not like I would be opposed to it. It just hasn't been the right time." Mia looked at him. Eddie offered a quick explanation. "What? I didn't realize I had to hook up with someone immediately after coming to their defense."

Mia laughed. "Look, don't pass up a good opportunity. She's a sweet girl."

Eddie looked bewildered. "Well duh".

After an hour, Cari came up and sat next to Eddie at the bar. "What are you drinking young lady?" He asked.

"Young?" Cari asked sheepishly. Eddie kinda dated himself with the question. He was pushing 40 and buying a drink for a girl half his age. Before he could respond, Cari said she would have a beer. They toasted and began drinking. The conversation between them was interesting. Mia got involved when Cari asked about him hanging out with a younger woman. Mia grinned. "I doubt the age difference is really a concern for him," she opined. Cari looked at him with confusion. Eddie didn't blink. "Look, I've hooked up with women younger than me." Cari seductively smiled at him. "She was 24 and this was nearly two months ago," Eddie said before she could ask the question. Mia just rolled her eyes.

"Do you think of yourself as a sexual person?" Cari asked. Eddie thought for a moment. "Well, I'm not terribly bad-looking and I've been known to be charismatic and even charming at times. So, maybe." Mia couldn't help herself. "Man, it's getting deep in here," she quipped.

"You don't think so?" Eddie asked. Mia leaned in, giving Eddie an eyeful of her cleavage. "Let's make a bet. You travel to five random places and hook up with someone there. Take a picture of you in bed with them. Clothes have to be off to be taken seriously."

Eddie gave her a look. "Are you serious?"

"Very," came Mia's reply.

"Okay, and what's at stake?" Eddie implored.

Mia thought for a moment. "Half of my tips for the first month after you come back. If you lose, you have to be my personal servant for a month." Eddie thought for a minute. "Are there any other rules?"

"No longer than three days at each place. No prostitutes." Eddie shook her hand in agreement. "Here is my number to text me the pics." Cari looked a bit stunned. "Are you really going to do it?" she asked. "Well, it's that or be Mia's bitch for a month. I'm not exactly digging that prospect." The three continued talking and drinking for a few more hours.

It was nearly 4:30 in the morning when Eddie felt it was time to leave. Cari was hanging on his shoulder and he asked if she wanted him to take her home. "Yessss...," came the slurred response. Mia gave him Cari's address which was in walking distance. Cari had a little bit of difficulty standing and walking straight but Eddie kept her upright. Cari held onto him tightly, pressing her head against his chest as they continued to her apartment.

When they got to the door, Cari stood on her toes to gently bite Eddie's ear lobe. "You smell soooo....good," she mused. She pulled back and looked at him. "I want you to fuck me."

Eddie was hesitant. Any other time this would be a no-brainer, but he had reservations about taking advantage of someone who was drunk. He unlocked the door and helped her inside. Cari stumbled a bit into her living room before disappearing into a room. Eddie followed her. He found Cari passed out on the bed; the alcohol finally subduing her for the remainder of the early morning hours. Eddie went over and pulled her up to the pillows. "Eddie...," she drunkenly murmured. Eddie took her shoes off and placed a blanket on top of her before leaving the bedroom.

He was headed for the door when he realized that his keys were not on him. Mia had taken them from him after he slipped off his chair at the bar earlier in the evening. He felt the mishap was due to him not paying attention instead of the alcohol. Nonetheless, Mia asked for them. He would have to wait to until the morning since the bar closed early for the holiday.

Eddie decided to crash on the couch. He saw a blanket on it that he could use. He took his shoes off and stretched out on it. "Fuck, this thing is soft," he thought to himself. He pulled the blanket over him. It smelled like Cari's perfume. He stared in the dimly lit room for several minutes before he began to drift to sleep. He hoped Cari wouldn't be mad at him for staying there.

The honking of a car horn awoke Eddie from his sleep. He looked around, momentarily confused as to where he was before remembering the chain of events just a few hours prior. He checked his phone. It was noon. He sat up on the couch. Surprisingly, his head wasn't as foggy as he thought it would be. "Up yours hangover," Eddie smiled to himself as he stretched before standing up. He thought about checking on Cari before heading out. It was uncertain if she was still sleeping but the one-bedroom apartment was quiet enough to suggest that she could have been.

He heard a door open and looked to see Cari walk out wearing a red Ms. Claus bra and micro-skirt set with red heels and Santa hat. The bra was sheer but did cover her nipples a bit. She walked towards Eddie and paused for a moment to let him soak in the sight in front of him. Eddie's jaw dropped. "Holy shit," he said. "Oh no handsome. You mean Merry Christmas," Cari said as she resumed walking towards him. She stopped in front of him and gently pushed him back onto the couch. She straddled his lap as she leaned forward to grab a remote from the table behind Eddie. Suddenly, AC/DC's "Shook Me All Night Long" began playing. Cari traced her finger back across the side of Eddie's face as she got up and began dancing in front of him.

"Last night, I wanted to give you a present. But circumstances changed and you were quite the gentleman. I'm glad you stayed the night." Cari turned around and began grinding on Eddie's lap. He was getting turned on and there was no way to conceal it. "I feel your cock getting hard," Cari whispered seductively as she leaned back into him. "Soon."

She stood up and grazed his chin and nose with her breasts that were nearly popping out of her top. Eddie was enchanted by her moves and for a fleeting second, regretted not ever checking out the strip club where she worked at just a few months prior. But this...this was something else. A personal lap dance that was going to involve him getting laid.

Cari moved back to straddling his lap in a reverse cowgirl position. She took his hands and placed them over her breasts. "Touch me," she said as he gently squeezed the firm and perk breasts that were now in his hands. She began grinding his now erect cock while helping him massage her breasts as she moved to the music. She slid down to the floor and turned around. She looked up at him as she began unbuttoning his pants. She pulled out his rock-hard cock and admired the meaty 10 inches she held in her hand. She began stroking him and running her tongue along his balls. Eddie was smooth and shaven down there. Cari was going to enjoy this. She continued jerking him off until she stopped to pull down his pants. She ran her tongue along his shaft while massaging his balls. Cari briefly sat up straight before taking Eddie's cock into her mouth, deep-throating him. Her saliva dripped down his shaft onto his balls. Eddie let out low moans of pleasure.

Eddie felt that if he let her continue, he may blow early. When Cari came back up after taking his cock deep down her throat again, he picked her up and sat her on the couch. He slid off her skirt and admired the bald, hot pussy in front of him. He began to gently lick the lips of her snatch. His beard adding more sensation as he let his tongue explore her private area. Cari moaned her approval as she held his head. "Oh fuck!" she cried. Eddie continued to lick her pussy as she squirmed around in ecstasy. "Fuck me, Eddie!! Fuck me now!" Cari demanded.

Eddie climbed up towards Cari, kissed her lips and slid himself inside of her. She was tight. Her pussy was warm and wet. Cari had a death grip on his ass cheeks as he thrust inside of her. He started off with slow, rhythmic gyrations before increasing his speed and force. Cari was overwhelmed by it all. Eddie stopped and sat her on his lap. She slid herself carefully onto his cock and began riding him. Eddie removed her bra and took her breasts into his mouth. Cari moaned loudly. "Oh yes, baby. God yes!" She continued milking his cock, the two of them sweating profusely in the warm apartment.

Cari stopped and looked into Eddie's eyes. She leaned in and kissed him passionately, her pussy clinching his cock. "I've wanted you for so long," she said. She got off him and got on her hands and knees propping herself up on the couch. "Take me from behind." Eddie obliged.

He got up and removed his sweat-drenched shirt before taking his hand and massaging Cari's pussy. He added some saliva but she was so wet it wasn't needed. He entered her pussy and thrust himself deep inside her. Cari moaned. This was heaven. Eddie looked at the wall in front of them. He saw Cari's little perky breasts moving rapidly with his thrusts. Eddie felt himself getting close. Cari felt it too because she said, "Not yet."

Eddie slowed down the pace but when Cari began rubbing herself, he knew she was close. He began to increase his speed again. Cari's pussy was dripping now. Eddie thought he saw her squirt but he couldn't be certain. "Cum on my face," Cari requested before dropping down on her knees in front of him. She leaned in to lick his balls but as she did, Eddie blew a load that hit her in the middle of her forehead and into her hair. He let out three more generous loads before Cari was able to lean it and lick the head of his cock.

"Holy shit," she said. "You mean, Merry Christmas," Eddie said, trying not to laugh. They collapsed on the floor laughing. Cari looked at the time and saw that it was nearly 2PM. "You're going to be late," she warned. "No, it's fine," Eddie replied. "I called out." Cari smiled and her eyes got big. "I need to clean up." Cari got up and disappeared into the bathroom. A few seconds later she poked her head out. Looking at him she said, "Are you going to join me?" Eddie smiled and got up. He spent the next several hours fucking Cari before they both left for Mia's so he could grab his keys.