My Ex’s Roommates Became my Personal Harem Part 2 - Overtime [M20s, F20s x5, F41] [Harem] [Sensual] [MILF] [Oral] [Slow Burn] [Long Story]
Sequel series to “My Girlfriend Left me Alone with her Roommates.” I really enjoyed taking more time fleshing characters out and building around their experiences. Enjoy.
PART 2 - Overtime
Helen’s marriage wasn’t the happy ending that most girls sought out from a young age. She didn’t exactly get her Prince Charming, her castle atop the hill or any of the other fairytale cliches.
It also wasn’t the abusive cycle that some women found themselves in, unable to pull themselves out of the never ending bog to solid ground. She was fortunate in that aspect, she supposed.
It was a perfectly middle of the road relationship that she and Danny had simply found themselves in. High school sweethearts that stayed together in college and were married shortly after. Two kids followed in an even shorter succession.
She often wondered if either of them had gone to a university out of state if things would have been different. If their love would have persevered and been made stronger or if they would simply fall out of love, fall out of touch, fall out of this manufactured relationship they had built.
Happiness in relation to marriage wasn’t a fleeting moment or puppy love between to horny, attractive people. It was a long lasting state of being that could only be achieved through deep satisfaction with a partner. Someone who made you whole.
It barely surprised Helen when she had found Danny with one of his interns in their bed. It hardly registered to her because she had known it was over for some time now. He didn’t touch her. He didn’t do the little things. He didn’t ever say “I love you.”
At 41 years old she had been cast aside for a 20 something year old like she was expired milk in the back of the fridge, like he only needed a quick trip to the store to replace what he had lost.
It was painful, regardless of how she felt about him prior. Seeing the naked form of a girl half her age writhe on top of him. Seeing his face, full of shock and embarrassment, realizing he had miscalculated how many days she would be gone visiting her family.
The divorce process was significantly worse, though. It hurt her far more than watching that blonde dismount the man she had committed her life to. The tedious, painful separation of years of thread that the two of them had knit together was almost unbearable.
She did her best to ensure the process went smoothly - she had no interest in trying to claim more than she was owed or make Danny’s life worse. Her lawyer had advised to seek the maximum possible return but she shook him off, wanting to simply get through it and make sure her kids were taken care of.
The youngest was 16 and he’d be affected by it the most. If only Danny could have kept his dick in his pants for two more years. Just two. Then, this wouldn’t be so difficult.
All of this felt like ages ago. The moment Helen had caught the adultery in real time was nearly a full year ago now but the proceedings had just wrapped up not a month prior.
That’s when she had gone on her first date. She waited until it was over and installed a dating app on her phone. Being conventionally attractive with fiery red hair and sparkling green eyes it didn’t take her long to get a match. But she soon found she was well over her head.
The first date was with a younger man, nearly a decade her junior, who talked about himself just about the entire length of dinner. She found it difficult to get a word in edge-wise and gave up after his fourth story detailing him and his “tech bros” scoring a big client.
Wealth with no worth meant nothing to her. She politely declined a second date when he reached out again, opting to try and find someone more her speed.
This time a handsome, dark skinned man who was only a few years younger than her. She was out of touch with how to date but even worse, how to flirt. How to communicate desire.
Helen had spilled a glass of red wine on herself while trying to seductively twirl it in her hand. Embarrassment had flooded her system and the man had been kind - offered to help clean her up, offered to pay for a cab home. Oh god. He thought she was drunk. 45 minutes into a date and she gave off the impression she was a drunkard.
Tears rolled down her cheeks as she now sat alone at home, darkness and a fresh bottle of wine as her only companions.
She was still in her stained dress, hand trembling as she silently cried to herself. Her shaky finger hit the “delete” button, erasing the dating app from her phone.
Helen downed a large sip taken directly from the wine bottle, small beads of maroon dotting the corner of her lip. She wiped them away with her already ruined dress. It didn’t matter anymore. It’s not like she’d be wearing it on a date ever again.
Whether it was the alcohol, the failed dates, the simple yearning for physical affection or a combination of all three, her heart raced as a new feeling started to slowly replace the sadness.
She was painfully aware of her physical needs still going unmet, her body craving a connection that she had lacked for many years even when she was with Danny. A connection that had fizzled out and been renewed for him - not for her.
Her breath quickened as she fumbled with her phone, clumsily pulling up an adult website. Danny had watched porn with her once before, a sort of no holds barred sexual encounter when they were much younger.
Outside of that one instance she had never watched pornographic content, certainly never on her own. But she needed relief and quickly.
Helen spent a few unwelcome seconds scrolling past a number of videos that she had no interest in, stumbling across one of a female teacher and male student.
Something she couldn’t quite identify pulled her to it, clicking on the video and watching the opening minutes with an intense curiosity.
Corny. Hacky. Terrible acting, worse dialogue. She knew the stereotypes but this was worse than she could have imagined. Until the sex started.
It wasn’t graceful nor particularly erotic in itself but she was glued to the screen, not breaking as the pornstar sloppily gagged on the “student’s” shaft.
A wetness alerted her of her body’s reaction to the scene, her hand gently and unsurely making its way down, moving her underwear to the side. Her slick folds welcomed the touch and she audibly gasped as she felt her own swollen clit. She was far too pent up.
With a hand that was far too under-practiced in such measures, she slowly began rotating a small circle around her sensitive clit, slow motions slowly becoming slightly more vigorous as she picked up steam.
Her heart beat faster and her breath deepened while small, nearly inaudible moans escaped her lips as waves of pleasure radiated up through her nervous system.
She continued to work her hand as she watched, the woman taking the entirety of the man into her mouth before standing up and instructing him to fuck her. It was brash, crude. Not a real representation of sex. But she couldn’t help but be extremely turned on by it.
A wave of embarrassment shot through her, heat pulsing through her chest as she began picturing herself as the teacher. And the student… Michael.
The young man from the office she had been mentoring, whom she had confided her marital troubles to, who she had spent several late nights talking and joking with in the waning hours after the work day.
The same one who had shared a story about having spontaneous sex - group sex, at that - to get over his cheating ex girlfriend. A story he told her in confidence. One that only someone with a broken heart could relate to.
A deep breath escaped from her lips and she found herself reaching climax. The tiny fire of pleasure had rapidly ignited to a roaring fire as her fantasy took over, pushing her over the edge and soaking her underwear.
Helen knocked her phone to the ground as she came, choosing to save the wine bottle instead.
As she sat there breathing heavily on the couch, the raucous sounds of love making played from her phone’s speakers. Her heart thumped loudly in her chest. She knew what she wanted. For the first time in years, she knew.
_
Michael bumped into Elba as he hurried out of his room in a not-so-pleasant attitude.
“Oh man I’m sorry, didn’t see you.”
“Uh-huh, you weren’t just trying to make an excuse to hang out with me were you? I’d soooo hate it if you came out thrifting with me.”
Shit. He’d drop everything to go with her if it had been any other time but he’d just been summoned by Helen. He couldn’t leave her out to dry, not with the way she had so generously treated him.
“You actually caught me at a bad time, I gotta go into the office and help Helen with some contracts. Next time?” He tried to sound apologetic and sincere without being condescending.
“Hm.” Elba looked him up and down, her dark eyes scanning his body for any signs of distrust.
“I thought you were making an excuse but you really have to go, don’t you?”
“Yeah, if it was anyone else I’d pretend I didn’t see it until tomorrow. But she’s already going through a lot and if there’s a deadline that has to be met so she doesn’t get in trouble I’ll help her any way I can.”
“Alright, fine. But that’s a big IOU. Like, a big, fat one that I’m probably going to parlay into you buying me lunch.”
“And dessert.” He added.
“Promise?”
“Promise. Whatever you want.”
Silence hung in the air as he kept his eyes locked on hers. He’d let her take the dessert comment whichever way she wanted. He’d happily oblige to either meaning of the double entendre.
“Lunch and dessert at my place of my choosing. And it has to be this week.”
“Deal.” He nodded.
“Good. See you around, have fun.” A smile that could melt icebergs from Elba as she bid him goodbye, disappearing out the front door.
He breathed out, rushing to collect his things as Elba spun around in his mind’s eye. If there was anyone he wanted to get closer with, it was her.
Before long he had the essentials for an office run and potential late night powwow with Helen - some light snacks, essential toiletries and a change of clothes. It had only come to an overnight stay once before, a rush to meet an important quarterly deadline but that’s all it took for him to be prepared every time he clocked in after 5pm.
Michael tossed his go bag into his car, climbed in and set his playlist to shuffle. The waning afternoon sun kissed him goodbye as he left the complex, turning onto the highway and headed to the office.
_
Elba perused the small thrift store’s wares, running her hands over pairs of jeans, t-shirts and boots as she thought of potential outfit combinations. There were so many boots. Why were there all these boots?
The clothing items were nothing more than a distraction at this point instead of serving at the primary focus of her afternoon as originally intended. She couldn’t help but let her previous line of thinking storm its way back in, Michael’s face appearing in her mind’s eye.
Her stomach dropped as she considered the implications of her latest obsession. With her untimely separation from Josh, romantic pursuits of any kind had not crossed her mind. However, that night of indulgement, that night she kissed Michael and turned their apartment into an orgy had sparked something inside of her.
Her soul had collided with his in a way only the two of them could understand and since that moment, she couldn’t shake him.
It was wrong to say she was in love; that was a far advanced version of what she felt. Or at least she thought so. It was an emotional and physical lust that drove her to be around him whenever she could.
Ugh. Was that just what love was? A lust of the soul and of flesh? She didn’t mind seeing him with the other girls. It was fun to dive into a completely untapped sexual pool and explore opportunities she never would have normally.
It was fun to have sex with him, to watch him have sex with the others. It was fun to be around him.
Fun wasn’t exactly something she would have described her general lot in life before these last couple months. Her relationship with Josh was like a part time job, her school work was like a full time job and her part time job was like… well it was like having a part time job on top of two other jobs.
Everything in her life had felt like work until recently. She relaxed, she had fun and she finally found someone she wanted to be around.
Ugh. Maybe she was falling for him. But it was so soon, far too soon to admit that she was. She wanted to bask in this new feeling and just have fun.
Soon, Rylah would graduate and the house would be down another. Blaire and her were next, Emelia a year behind. The college experience was slowly coming to a halt and there was no reason for her to rush into a relationship. Especially if she shackled herself to Michael.
That would put some kind of ownership, a fence around him that she wasn’t ready for. She wanted that freedom for an orgy to break out after they had all had too much to drink. She wanted to hear Blaire and Emelia giggle about moments like the sauna yesterday. She wanted to see Rylah have that deep hunger in her eyes as she approached him.
There was something so fascinating and so alluring about their current complex arrangement that she didn’t want to upset the balance by introducing a new element.
If she had feelings - which she was beginning to realize she might - a lot of that fun becomes more complicated. Messy. She didn’t want that.
If there was any chance of her and Michael having a genuine shot with one another she didn’t want it to be complicated. It had to be clean, pure. At least mostly pure.
“That was it,” she thought. She promised herself there and then, in the corner of a small thrift shop, that she would stay friends with benefits with Michael until she graduated.
No use in making things complicated. Have fun. But. But. Make a move immediately if she still felt this way a semester from now.
Elba exited the store and drove straight home. She already had a far more productive day than she had set out to have.
_
Helen sat behind her desk, tapping a pen on the flat surface in front of her. Her other hand fidgeted with her skirt, tugging at the bottom of the already short material.
Her heart raced. Maybe this was a mistake. Having Michael come in to complete something she very well could have had him do the next day might not have been the best way to handle things.
She took a deep breath. In, then out. Her cleavage was very visible, she made sure of that, and her skirt was far too short for normal comfort. Helen kicked herself and realized she had been far too inspired by that teacher porno while half drunk on wine.
This was silly. Unrealistic. She’d call him now and cancel, he was probably just now leaving his place.
Ding.
The elevator let her know someone had made it to the second level. He was early. Of course he was, he probably wanted to get this done with and back home. To enjoy his Sunday evening. Oh god, this was going terribly already.
Another deep breath as she shifted in her chair, Michael’s figure rounding the corner.
“Whatcha got for me today?” He called out, slinging a bag into his hardly used office chair before entering her office.
“Just stay calm. You got this.”
She gestured to the chair in front of her and slipped into her comfortable professional mindset, explaining the two contracts she needed revised to meet a deadline. She just failed to specify the deadline wasn’t until Tuesday at noon. But she’d get to that later.
The thought of her spilling wine on herself came back to her and caused her to physically cringe. She walked herself back from the metaphorical edge, completely shedding the embarrassing memory to try and stay in the moment.
While the two worked on the language and structure of the contracts she made sure to bend forward whenever possible, a gratuitous view of her breasts on display. She even got up once and bent over to pick up a pen she discretely kicked away, her skirt hiking up as she did so.
Helen was sure that he had looked at her cleavage at least once, possibly twice. But she might have been delusional about the second time. Maybe not.
By the time they were done she was sure he had picked up on some of the signals she was flaring. At least she hoped so. She was scared of coming on too strong too fast and pushing him away so it was best that she kept it relatively subtle.
“You look nice. Date tonight?” Michael offered. So he had been looking.
Helen shook her head, a hot flush coming to her cheeks.
“Thank you, I’m glad you noticed but no - no dating for me. Not for a while. Not after what happened last time.”
He raised an eyebrow. “Oh? You didn’t tell me you went on a date, what happened?”
She unloaded the gory details of her back to back failed dates, the professionalism act dropping as soon as she was in gossip mode as it had many times before.
They shared a laugh over her wine story and he teased her for being careless. They were in high spirits. It was the only chance she might get.
“Listen… Michael…” she chose her words carefully as if she were picking her way through a bush of thorns.
He blinked, silently waiting for her to continue.
“Ever since my ex-husband… I, you know, I haven’t… I haven’t had my needs met. I’ve been in this insane spiral and dating wasn’t for me, drinking alone is depressing and I’ve just hit a rut. I need something. I need a jumpstart, to feel alive, a reset button or, or something, I don’t know -“
Michael stared at her and she could feel herself fumbling, feel herself getting flustered.
“I need you. I need help the way you-“
Her sentence didn’t finish. Michael’s lips pressed against hers and heat swept through her body. Flesh on flesh. It excited her.
Slowly, he pulled his lips away and met her gaze.
“I’ll help you. But it can only be that, just help.” He said in a soft tone. She nodded. He returned the nod now that they were at an understanding.
“Okay, good. And to be safe…”
He closed her office door and locked it. They were now as isolated as they could possibly be within these walls.
“ I want- I want to try something, if that’s alright.”
“Of course, anything.”
She bit her lip as she put her hand on his crotch, gently rubbing and teasing. His hot breath expelled on her skin. She started to kiss his neck with a loving softness, bright red dots of color left behind.
Then, slowly, she sank to her knees, looking up at him and letting her shoulder length curls of ginger fall. A quick undoing of his button and unzipping of his pants allowed her to tug the cumbersome clothes off.
Just his underwear remained. Images from the porno she watched flashes in her mind, the woman taking the man into her mouth with such lewd ferocity and eagerness. She wanted to do the same.
Another tug and Michael’s half erect member now sat in front of her face. A radiating heat washed over her again as equal parts anxiousness and excitement flooded her body.
Helen took it in her hand and closed her mouth around the tip, slowly stroking her head back and forth as it twitched in her mouth. She felt him hardening as she sucked, filling her mouth even more.
It tasted so good. His natural scent, the smell of sex, the skin of his member pressing against her tongue. It felt like she was in a trance, picturing herself as the naughty teacher going down on their student.
A hand pressed against her red curls and she realized her eyes were closed, opening them to look up directly into his. She moaned around his cock, the sight of him looking down at her just another turn on in the moment.
Her hand got involved now, running up the length of the shaft that was free, her mouth still suctioned to his head. She began to drip with excitement as she went down on him, moving faster and faster as her body ached for pleasure.
She moaned and sucked, stroked and licked.
“H-Helen, I’m gonna…”
She kept going, her heart pounding ferociously in her ears, taking in his length deeper and deeper.
“I’m getting close, I’m gonna -“
Faster. Faster.
“Helen I’m cumming-!”
Michael managed to force out and she pulled away. But it was too late, her excitement and focus in the moment had sent him over the edge, hot white ropes coating her chin and open cleavage.
“O-oh no, I’m so sorry,” she breathed. “I didn’t mean to…”
Her skin was warm with the feeling of his semen and it turned her on even more. Still, she was disappointed that she had finished him so quickly.
His dick hung in her face limply, softening when it had just minutes ago been doing the opposite for her.
“Stand up,” he said softly. “And lay back on your desk. We’re not done yet.”
Helen did as she was told, lying down on her back and lifting her legs up for him. He took them over his shoulder and slid her underwear down off her body, lifting one leg and then the other to fully tear them from her form.
An electric shock made her gasp as his tongue found her clit, a far more intense feeling than when she had simply touched herself. It had been so long. She needed this.
Helen’s hand reached out and grabbed the back of his hair, pushing him in more, his tongue exploring her slick folds and engorged clit. It sent tingles of varying levels of pleasure that emanated from her groin out to her legs and down to her toes. They curled as she tensed at his touch, moans showering down on him, each one its own individual compliment.
“Keep… going.” Her labored breathing could not stop the words from spilling from her lips and only cause him to intensify his efforts.
Suddenly she felt something at her entrance. A finger. It pushed into her tight, wet walls and sent a shiver up her back. It also made her cum instantly.
A series of tense twitching and contracting made its way through her lower half as stars dotted her vision. It had been far too long since she experienced penetration of any kind - and it showed.
“Oh fuck…” she groaned as her body surrendered to him. Another finger.
The tightness she felt inside her pussy increased as both of his fingers now curled back toward him, brushing against her G spot. A shudder.
His tongue hungrily serviced her clit while his fingers constantly pressed against her most sensitive area, bringing her closer and closer to the brink a second time.
Helen couldn’t believe how Michael was devouring her, that this type of sexual encounter existed outside the world of internet pornogrpahy. She loved it.
The barrage of intensity from his fingers and tongue eventually caught up with her, shortening her breaths and pushing one simple phrase from her lips:
“I-I’m cumming~”
An explosion of pleasure and fluids erupted from her, a fuzziness taking over her vision while her body went completely taught then utterly slack, legs helplessly hanging over his shoulders.
Helen knew in that moment that she had been truly satisfied for the first time in many, many years. All without taking him inside her. She lay there, panting, hardly registering that he had unlocked the door and opened it.
Within seconds he had appeared at her side again holding a plain white tee.
“Here, it’s an undershirt I always have packed. Better than paper towels for, uh, you know.”
He offered a smile as he handed her the shirt. She gratefully accepted and wiped his still warm fluids from her face and chest.
“I, uh - thank you. Thank you. I needed that.”
Helen said, allowing the shyness to melt away from her, trying to gain the confidence in herself she had once had.
“Sorry I finished you so early, guess I was caught up in the moment,” she laughed.
“Honestly, it was so good I couldn’t help it. You really took me by surprise.” The two of them both blushed slightly but without the awkward tension there was before.
“I guess… I guess that’s that, then.” She offered quietly. “Please don’t make a fool of yourself, Helen. It’s just casual sex. It’s normal. Completely normal.”
“Well if you ever need this again, I’m uh… I’m more than happy to help, I just don’t want to jeopardize our professional relationship, you know?”
She hesitated. Of course she’d thought of that but hadn’t cared enough to think that far ahead in the moment.
“One time thing,” she promised. “Really, thank you. I think I just needed to break out of my shell… and honestly we’ve shared so much…” she didn’t have to say more for him to understand.
“Well, listen, if you ever need something like this and are willing to get a bit more experimental, I know a couple of girls who give great massages. Just tell ‘em I sent you.”
He handed her a scrap of paper with the name “Blaire” next to a phone number. Interesting. Perhaps she’d be getting a massage in the near future.
“Oh - I requested you work in the office tomorrow. Don’t go to the worksite early. In fact, come in late if you need. One time benefit.” She smiled warmly.
He smiled back, nodded and packed his things.
“See you tomorrow, Helen.”
She was alone again. This time, a little more satisfied and a little more hopeful.
_
I’ve got the craziest story to tell you when I get back. Wait up for me.
* *
You got it. :)
Elba estimated Michael had about 15 minutes left before he was home based on the time stamp of his message. Her heart skipped a beat when he texted her privately and not in the roommate group chat. It always meant just a little more when he did that.
She was right and he walked in through the door a little under a quarter of an hour later. It was about 8pm, late enough to be dark but not overly late. She’d hope to get some hot gossip from him, maybe a new plot twist in Helen’s divorce proceedings or better yet, she’d found a new man.
Michael gestured for her to follow to his room and he flopped on his bed, patting the seat next to him. She gladly took it.
“Wait, what’s that smell? Stop. Don’t tell me…” her mouth gaped as the familiar scent of sex lightly wafted from him. His face, in particular, smelt of recent copulation.
“Oh yeah. She wanted me and I dunno, I obliged. She was adamant that it was purely to get her frustrations out but get this - she made me finish before I ever got inside her.”
Elba took in his words and breathed heavily, her head laying on his shoulder.
“Oh yeah?”
“Yeah so she wanted to try and seduce me I think because she wore this insane low cut top I’ve never seen before and this super short skirt-“
Her hand interrupted him, moving up and down his crotch, her attempt at coaxing his member back to life.
“Oh, uh, I'm actually not sure if I can physically get it up agai-“
“Shhhhh.” She whispered and interrupted him again. “Just keep telling me about it.”
He did just that, describing Helen’s eagerness to go down on him and how that eagerness led to him finishing early.
Elba stroked him outside his pants, made her way inside of them, finally pulling out his member and putting her mouth on it. It tasted like sex. Like when she shared it while Rylah.
“Mhmmm.” She murmured in acknowledgement as he continued to go into detail about the sexual encounter, Elba going all out, sloppily taking his cock into the back of her throat again and again.
She managed to not only get him hard very easily but to cum again for the second time in about an hour’s worth of time. She welcomed the hot load down her throat, the saltiness a mere byproduct of her deeds.
Elba pulled her head up, swallowed, then winked and lay against his shoulder again. He sat wordless for the first time since he arrived home.
The two talked and giggled as the night wore on, falling asleep as the darkness deepened.
Two souls that found solace in one another.
Two like minds that drifted off to the same dreamscape that night.
END PART 2