Mom Helps Bi Son & Friend Explore: Story Thread

[ready2cuck]

Mom Helps Bi Son & Friend Explore

A fellow Lit member and I started a fun story we wanted to share, and hopefully get some help on from other writers. Here's the setup, and the first few sections, which switch back and forth between the Mother and Son's perspective..

INTRO:

Samantha is an attractive business woman in her late 40s/early 50s. She works part time at a lawyer's office and always dresses professional but with a hint of reserved sex appeal - often accented by some hot heels and thigh high stockings. Her 5'5” body is in good shape from some light exercise twice a week, and she has beautiful eyes, short-ish brown hair with youthful highlights.

She and her son James have been living together for the past 10 years – ever since her and her husband got divorced. Her ex is pretty much completely out of the picture, leaving James to slowly graduate into the man of the house as he grew older. Now 26, and working on building his own law practice (hence the reason he’s still living at home with Mom to save some money), he handles all of the yard work, house repairs, and other masculine duties that a husband normally would.

Samantha and James are incredibly close – sharing a loving, fun, and playful relationship with a hint of innocent teasing and flirting. It’s harmless enough, but being a young man with raging hormones, he has always found himself attracted to her at times, and every once in awhile, would throw her into one of his masturbation fantasies while laying in his room at night - especially the days she dressed particularly hot for work.

James has had about 3 serious girlfriends while living at home with his Mom, and they have always been very open about their dating lives. Samantha will have a date offer every few months, but she never seems to spend more than a few months interested in any particular man. After her divorce, she’s incredibly wary of getting into another relationship with the wrong man – and is content with just having some attention, and perhaps a few nights of passion, with the gentlemen she’s approached by.

She’s usually much more interested in her son’s relationship status. Who he’s dating, if it’s serious or they’re “just friends,” and whether or not she thinks the blondes he tends to bring home are even good enough for her son. She’s always known how handsome he is, and has been stopped cold a couple of times as she’s glanced him doing yard work with his shirt off. This is why she was so incredibly shocked when she came home late from work one night, and heard the slow moaning of two men coming from living room..

 

[ready2cuck]

James:

Mike and I have been friends since college, and have shared great memories together - some of the best and most exciting of my life. We've been to plenty of strip clubs, had lots of drunken nights out, and have shared lovers and even girlfriends from time to time. There's always been a great connection between us, but it wasn't until recently that I realized I might have a real attraction to him.

We're both in our mid to late 20s, relatively recent law school graduates, and are working on starting a practice together. This is nice because Mike got engaged to his girlfriend recently, so our hangout time has been cut a little short as he's focused on planning his wedding. We still get together every Wednesday night at my house though, to talk about our business, have some beers, watch TV, and plan for his bachelor party.

It was on one of these Wednesday nights where our friendship took a big turn. We were in the living room of the house I share with my Mom, having couple drinks and streaming random videos online through the smart TV. Being a couple tipsy and horny boys, I eventually went to a porn site and started surfing around. We’ve both always had a thing for hot moms and older women, so I click on a milf video and let it play in the background while Mike and I talked about his bachelor party plans.

The porn site grouped similar videos together and played them on a loop, so new clips of hot moms being fucked by young studs kept cycling through. Eventually a very special video popped on the screen. This one showed a very attractive brunette milf with two well-built young men. Mike and I kept chatting until he stopped me and said, "Whoa man, that chick looks just like your mom! Check it out, those two guys are going to nail her!"

I turned around to see the screen, and he was right. The lady in the video did have a striking resemblance to my mother. I had confessed to Mike that I always harbored a secret sex fantasy about Mom, and he always said he was jealous that he wasn't her son - although Mike's mom is a pretty hot piece of ass herself! I was transfixed by this Mom lookalike on screen as the two studs laid on either side of her, sucking her tits and kissing her. However, things took a strange turn as the milf pushed the two boy's faces together and encouraged them to kiss...which they did eagerly.

"Holy shit," Mike said. "I've never seen anything like this before."

"Me either," I said back, a little shocked.

The two boys kept making out with each other, and then with the milf, before things gradually heated up. The woman laid back on the bed while one of the boys ate her pussy, and his friend sucked his cock. Then the woman begged to be fucked, and got pounded hard. After she was satisfied, the two boys then took turns on each other, with the hot mom lying back watching them fuck each other’s asses.

The whole scene was new to me and Mike, and yet incredibly erotic. My cock started to strain against my jeans as I discovered myself surprisingly turned on by the bisexual lovers on screen. My eyes were glued as the scene became even dirtier and dirtier. Lost in the moment, I stopped to turn around, and saw that Mike actually had his cock out and was stroking it. He and I had jerked off to porn together a couple times before, but it was always to women.

Without saying a word I pulled my cock out too and joined him in jerking off. I pushed my chair next to his and we stroked our shafts in unison. One of the men in the video started giving the other guy a sloppy blowjob, and my own mouth started watering. I kept glancing down at Mike's cock and for the first time noticed how beautiful and delicious it looked. He caught me looking at it and stared into my eyes lustfully. It was an unspoken invitation, and I got on my knees and for the first time put a cock in my mouth.

I had no conscious idea what I was doing between my best friend’s legs, I was just overcome with lust. It felt so naughty, so sexy, and so passionate. I became more eager and started blowing Mike just like a porn star. I was so lost in the moment, I wasn't thinking about anything else other than these new feelings coursing through me. I hadn't even noticed what time it was, and that my own mom would soon be home..

 

[ready2cuck]

Samantha:

My ladies night was a dud and I came home an hour earlier than normal. I knew the boys were hanging out so I thought I would sneak in and not let on that my big night out had been a bust. My girlfriend was to bring this cute guy and only showed up with her date.

I had been looking forward to a little action, especially since Betsy had been building this guy up for weeks. I had on a thin white blouse, cut low and open and a black skirt that wrapped around me nicely. I was not wearing a bra and feeling very sexy. I had a few drinks before Betsy and Tom arrived and the disappointment was fairly obvious.

I excused myself after a few more drinks claiming a head ache. Really I just wanted to get home to old reliable waiting patiently in my night stand.

I slipped in the side door and poured myself a vodka. I slipped off my shoes and walked towards the stairs. The light from the living room caught my eye as I passed, but that is not what stopped me in my tracks. On the screen of the TV was a woman who looked almost exactly like me. In front of her were two young studs fucking. I nearly dropped my glass.

I watched for a second, then looked to the left where the boys usually sat. My mouth opened as I saw my son giving his lifelong friend the most intense blow job ever. I sipped my vodka and watched as Mike's face was intensely enjoying my son James’s work.

I was shocked, never imaging my son was bi. I mean he has been with a lot of girls. Not that there is anything wrong with it but he is so masculine and sexy and well I guess I just never saw him like this. But seeing him now I was super turned on. I had seen him with girls before. Spying is one of a mother's favorite things. He is a good lover. I have taught him well, never in the flesh but you know – suggestions of what a woman likes and tips. I’ve also spent many a night after giving him advice with Mr. Reliable, my vibrator, upstairs with my dirty mind.

"I am gonna cum" Mike said as my son had his entire cock in his mouth and was sucking and moving up and down the full length of what was a really nice cock. My son did not shy away as Mike stiffened and groaned with pleasure as he released his cum. Sucking every drop and milking his cock until Mike pushed him away my son was all smiles. He sat back in his chair smiling at mike who was dumbfounded by the best blow job he had ever gotten.

My glass was empty and body was aching for attention as I continued to watch.

 

[ready2cuck]

James:

I sat back on the carpet and looked into Mike's brown eyes, anxious to know what they'd tell me post-orgasm. Would he be mad? Would he feel embarrassed or awkward? We maintained eye contact as he caught his breath, then his mouth curled into a devious satisfied smile.

I crawled over to him in his chair and put my hands on his thighs, then looked up at him like a naughty little slut and let some of his cum drizzle out of my mouth down my chin and onto my chest. He moaned at the sight, which only made me want to turn him on more, so I opened my mouth wide to show him his white creamy load coating the inside of his best friend's mouth. I took my time and swayed my tongue back and forth so he could watch me pushing his cum hungrily around my mouth, savoring the taste of him.

I could tell he loved watching me, which only encouraged me more. I felt like one of the porn stars we had just seen, and all I wanted to do was perform a good show for him. I remember some of the tricks my ex-girlfriends would try on me, and slowly got up and sat down on his lap facing him. I leaned forward and put my throat next to his ear and swallowed what remained of his load as loudly as I could, then gasped out loud with a satisfied "Mmmm."

I pulled my head back and our faces met again. Neither one of us had spoken yet - we were still going on instinct. His eyes got soft and he gave me the most tender look, which put my whole body at ease. I leaned in with my lips parted and our mouths touched for the first time. His tongue went in hard, like he had to devour me. He swirled it in my mouth passionately, and I could tell he liked the residual taste of his semen - because his cock was already completely hard again.

It was all such a strange feeling for me. I'd fucked plenty of girls, had some amazing sex, and even been in love a few times - but I had never felt such lust before as I did in this moment with Mike. I was completely enraptured with these new feelings...

"James," I heard a familiar female voice shout from my right side. "James, what is this? What are you doing with...with Mike?"

I was suddenly frozen solid as I sat naked on my best friend's lap with my arms around his shoulders, glowing from the first gay experience of my life. And of all people, my own mother was now standing next to us staring right into my eyes..

 

[cybal]

Samantha

My emotions were as out of control as my mind spun with what was in front of me. Somehow, even a fairly open minded experienced woman can come unglued when her son is involved. I try to steady myself as I look at my son and his buddy naked and basking in the after glow of an illicit event.
"You boys are bad" I said as my eyes slowly moved from James to Mike's. I had a hard time denying how turned on I was with my blouse unable to contain my nipples.
"What would your mother say Michael?" I ask trying to keep my eyes from roaming over his perfect body.
"And you James? You sucked that cock like a cheerleader at homecoming!" I heard myself say as the combination of the vodka and primal desires swirled in my head and body.
"I don't know what to say" I finally said and stared at the two beautiful grown men in each others arms. I felt a pang of jealousy as well. They were perfectly at ease with each other. None of the normal couple fears and questions. They knew each other and knew what each wanted and how to give it. There was only one thing they were lacking, acceptance.

 

[ready2cuck]

James:

It was impossible to describe what I was feeling at this moment. Here I was, kneeling on the floor in front of my best friend Mike - his pants down around his ankles and his cock slowly softening after his orgasm. My mouth was stained with the sharp flavor of his cum, my body coursing with an electricity of sexual excitement I had never experienced with any of the girls I'd had as lovers. I was on fire with a craving that had been laying dormant my whole life... And it had all been replaced in an instant with paralyzing fear and deep-seeded embarrassment as I heard my mother's voice.

She was standing right in front of me now, looking directly in my eyes as she spoke - asking for an explanation as to what she had just walked in on. I could barely form the words to answer her.

"M-Mom, I...I don't know...what. I, I'm so sorry Mom. I'm sorry..."

I just kept stammering. There were no words to explain myself - how does it even begin to make sense? It all just happened in a daze, propelled by a flood of repressed desire for something I didn't know I wanted. I had just performed my first sex act on a man...my best friend...on an impulse. Because of a look he gave me. One that told me to give in to my carnal cravings and feast on his cock. To make love to it with my mouth until he was satisfied...and to beg for more.

"Mom. I can't explain, it just...happened," I managed to say.

She just looked down at me, then over to Mike again. In her hand was an empty glass, which she swung back and forth slowly.

"James, I don't even know what to say to you. How long has this been going on for? I thought you liked girls, I'm shocked," she said

"This is the first time, I swear Mom. I've never even thought about.. Mike, tell her, tell her it was the first time," I said as I looked over at him terrified.

"Holy shit, yes. It just happened, I don't know how to explain it. I'm so embarrassed Mrs. Stone, I'll leave...just, just don't tell my Mom, please. It won't ever happen - you'll never see me here again," Mike pleaded as he pulled up his jeans.

I felt like time had stopped as Mom kept standing there not saying anything. Mike got dressed and went to get his shoes on, before she finally spoke again.

"Hold it Mike. Wait, please," she said. "I'm not mad at you two. It's...I'm just startled, boys. This was the last thing I imagined coming home to tonight. It's been a long day, my date cancelled on me, I'm tired - I just wanted to go upstairs and relax.. And then I walk in the door, and my son and his friend are...doing things to each other that I haven't even done to a man in years."

There was a pause as she tried to compose herself, realizing what she had just said.

"James, I love you, and will always support whatever it is you want - whether you want to date girls, or if you're gay...or bi...or everything in between. What.. What I'm trying to say is I'm not mad about what you two were doing, just maybe...MAYBE be more private about it in the future, okay? There's another person living in this house James, your mother, and you don't need to make me any more jealous of everyone around me having sex. You, Betsy, everyone but me," Samantha said breathlessly. She stopped and took some air - knowing that what she spoke was inappropriate, but true. It felt good to admit it to someone, and gave her a little twinge of excitement that it was her own son.

Mom looked upset, but also...I don't know, horny? I had never considered that she could have her own pent up frustrations, her own desires that weren't being fulfilled. I was confused. Was she actually not mad? Would she not tell Mike's mom all about this? Was she really jealous of me sucking Mike's cock? Of my efforts being rewarded with a nice load of young cum?

She continued, "I know what it's like to be your age and be curious about things. I mean, Mike's own mother and I, after your father left, well...I understand you wanting to experiment with things that feel good. Maybe, maybe I can even help, if you two are really curious about this?"

She walked to the kitchen to refill her glass, then drank another shot of vodka down quickly. What the fuck was she doing, she thought to herself? She WAS horny, and frustrated. She WAS jealous of her son. But then seeing that raw lust between Mike and James before her eyes also made her wetter than she had felt in years...and she wanted desperately to make the most of this situation, despite knowing how wrong it all was. She felt sexually powerful for the first time in a very long while. She poured another vodka, and sat on the living room couch, crossing her legs which were still clad in the black thigh highs and fuck-me heels meant to seduce her date.

"James, Mike. Sit down. Relax, it's okay. I swear I'm not angry, please," she said, with the boys following her orders intently.

Mike and I sat down on the couch next to my Mom, who had a strangely calm look on her face, and a hint of a naughty smirk. Was she actually enjoying this?

"Let's pick up where you left off. James, that was...wow...quite the performance! But oral sex, blowjobs, could just be the start for you two, if you're still curious about each other there's so much more for men to explore. From the looks of things, you were just beginning to heat up...and...well maybe Mom can help you figure out if this is really just a one time thing, or if it's more?"

My cock was starting to twitch as it grew hard, what was Mom doing? Was this really happening?

 

[cybal]

With a boy on each side of her Mom's head spun. Between the alcohol, the lack of sex and the scene she just witnessed there was not much she would deny them. She also knew they would be shy, even if attracted to her.
"So Mike, were you going to repay James for his kindness?" she said looking at the young man she had known since he was little. Without waiting for the blushing young man to answer she turned to James and said "Take it out. Better yet strip completely, both of you." There was a moment of hesitation but the vodka quenched that. "Go ahead, it's not like you have anything I haven't seen before" she said draining her glass and putting it on the coffee table.
"I am going to put on something more comfortable" she said getting to her feet. She was feeling no pain but managed to walk straight to the stairs. She stopped with one foot on the step and turned. "When I come back I expect you to be naked boys" and with a wink walked up stairs.
She was too far gone to second guess herself as she had two built, horny young men downstairs. She stripped and looked at her body in the standing mirror. "Not bad babe" she said to herself as she ran her hands up her abs and cupped her full D Cup tits in her hands. "They are going to suckle these like they did when they were kids" she said then grabbed her thick white terry clothe robe and wrapped it around herself. She flipped her hair up and out of the robe so it laid down her back then walked barefooted back down stairs.