AsshantiyAsshantiy
iamhorny943iamhorny943
MissteriousMeMissteriousMe
AmidaAmida
AprilSilverAprilSilver
Dasha_01Dasha_01
0bedientSlut0bedientSlut
Swipe to see who's online now!

A Disappointing Night Turns Around

Story Info
One thing leads to another with my best friend's mom.
2.9k words
4.39
90.4k
47
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was a fairly normal night out on the town. My best friend and I had gone out with the intent to seek willing women, as always.

Vinny was my best friend. We've been through everything since day one of high school together. The only major difference between us was Vin had it easy with women as I always had to play off of his better luck. Usually we would get in to a group of women and once he had one secured around his little finger he would big me up to the other ladies and I would then try my luck. Mostly Vin got pussy as easy as breathing and I was lucky to get a pity kiss before I went home alone.

Tonight my luck seemed to forget I was on the pull. Vin found a stunning woman who wasn't interested in anything but taking Vin back to hers and after ten minutes of seeing them entwined I resigned my attempts at pulling and made my excuses.

Vin reminded me as I made my escape from the new couple that I was staying at his tonight and threw me his house keys. The walk to Vin's house was one I felt I had made a thousand times over. With my eyes down my feet followed the route.

For the past five years Vin had lived with his mother, Ann, in a small place bordering the town centre. I had spent so much time there that I pondered on the way home why I didn't have my own key.

I opened the door to a relatively dark house but was surprised to see the light of the TV flickering in the lounge. I stepped lightly out of my shoes, into the lounge and found myself confronted by Ann's beautiful, soft smile.

For as long as I have been sexually active I have found her to be stunning. I think she may have even been the one to awaken sexuality within me. Her body is just classic! Curves swing the eye in an hour glass shape, thick top heavy thighs topped with a big bubble of a backside. An ass I noticed had been becoming finer and finer since her divorce as she now attended a gym twice a week. Her curves finished with her ample bust. So large it seemed that no matter what she wore she showed off some cleavage.

"Hello, where's Vinny?" She raised her head slightly and looked over my shoulder.

"He's off with another lady friend. I don't expect we will see him until early tomorrow."

She smiled a half-hearted smile and shrugged her shoulders. I couldn't help but wonder why she was up so late.

"He is SO like his father in that way!"

As she talked I detected the subtle effects of alcohol on her voice. I looked around and saw an empty wine glass. It was always a more flirty time with Ann when she had consumed a little wine. But this was the first time we had ever been without Vin.

The silence lingered a little. Ann propped herself back up from where she had slumped down on the sofa. She patted the cushion next to her and I sat down relieved after my walk. It may not have been far but it was slightly depressing.

"What you watching?"

She turned the volume up to a decent level and almost whispered to me. I leaned closer.

"It's a French film. One of my lady friends at work told me about it, she said after watching this she felt something in her life changed and she made me promise that I would watch it. So here I am." She added as an afterthought. "I thought I had the place to myself tonight, she has forewarned me it might be a bit racy."

"You want me to leave you to it?"

"No, no. I could use the company."

We sat and watched the film in silence for a few minutes. Eventually her drunken need to talk took over and we started talking about the two main characters of the film. Two stunningly beautiful French actresses dominated the screen. The tale told was all about their journey towards love.

A sex scene came up, our conversation quickly died off, it was a display like nothing I had ever seen, with some of the most beautiful shots of two women having sex I have had the privilege to witness. Well before the end of the engorged and highly pornographic sex scene I felt engorged myself. I shifted trying to keep my erection hidden from Ann. We didn't say a word during the scene. I could only pull my eyes away from it for a split second to peak over at Ann. She was as mesmerized as I was. Finally the sex ended, Ann spoke first.

"Well! That was quite something." She fanned herself with her hand. I couldn't think of anything to say, so stupidly I said what shot into my head.

"Your lady friend who told you to watch this film... I think she might have been trying to tell you something!"

Ann drew a sharp in breathe and put her hand to her mouth. For a second I thought I had gone too far by using my fingers to imitate a famous lesbian position, implying one set of fingers was her legs and the other her friends. We looked at each other and she dropped her hand.

"Oh my God! I think you might be right."

Again I didn't know what to say, so I went with honesty whilst I smiled like an idiot.

"You don't feel the same about her I take it?"

She clipped me on the shoulder and gave me a brief scowl, fortunately a smile followed.

"I can't believe I didn't see it!" She shook her head.

"What? That your friend wants to grind on you?" I joked again trying to keep the mood light and sexual. Ann giggled, her hand returned to her mouth.

"Oh I can't believe it! She's a husband and three kids, and she has been dropping hints for ages. We have even changed together."

I raised an eyebrow briefly picturing Ann and her friend, whomever she might be, naked and touching each other. Ann saw it as a question of her actions.

"What?"

"Nothing."

"Girls change together all the time!"

"Yeah I know. But I bet if I had seen it," Her turn to raise an eyebrow, I carried on, "I would have seen something more than two friends changing together. A touch here, a glance there."

Ann's hand covered her eyes.

"Oh I've been so stupid. I've led her on I am sure. All those times we..." Her voice faded off. I couldn't help myself as I asked.

"All those times you what?" I tried to keep it casual.

She stuttered and stalled.

"I... We... Well I might have let her grope me a few times. Playfully like... and shared a drunken kiss or two." She tried to make it sound casual. I couldn't help but laugh. She let me laugh alone until she couldn't help but join in. I decided to taunt her more than I already had.

"Oh I can't wait for Vin to come home."

She stopped laughing and looked at me.

"Why?" Her voice held such seriousness.

"Because I can't wait to tell him his mother is a raging lesbo!"

She let out a little involuntary scream and lunged at me playfully slapping my arms and chest. We lost ourselves in the joke until I ended up grabbing her wrists to stop her and our eyes locked. We quickly broke apart and settled back down like nothing had happened. We tried to carry on watching the film, a film that had run on and on and that we had totally lost the plot of.

We continued talking and I continued ribbing that she was a lesbian. Eventually she confronted the issue.

"Hey, enough of that you," I nodded and took her meaning to stop in a playfully non-serious way. "I can't be a lesbian!"

"Oh really. Why not?"

"Because I..."

I taunted once more.

"Because?"

She looked flushed but continued.

"Because I love penis!"

I couldn't believe what she said.

"What!"

She slowed every word down. I reminded myself she had been drinking, probably quite a lot.

"I LOVE PENIS!" She exclaimed looking me dead in the eye.

We both burst into laughter at the stupidity of the situation. But I saw my opportunity and I took it.

"Prove it!" I could barely believe I had said it. She stopped chuckling and came slightly back to reality.

"What?"

I gulped and clarified myself.

"Prove you love cock." In a move I thought belonged to a bolder man than myself I undid my trousers and pulled my still rock hard cock out of my boxers. Adjusting slightly to show my cock off, angling it towards her in the dim glow of the TV.

I froze as she moved staring between my face and my now exposed erect cock. I couldn't bring myself to breath. I had risked everything on what I hoped where the right hints and moments. I scanned her for a reaction.

Slowly a grin spread across her gorgeous face. Her hand slid across the sofa and stopped just short of my lap. We looked each other's eyes.

"Promise me you will never mention this to Vin, EVER!"

"My word of honour Ann. On my life!"

Her grin never faded as her hand took hold of my throbbing, sensitive cock.

"I probably shouldn't be doing this." She muttered to herself whilst staring at my penis.

Electricity shot through me at her touch. For as long as I had dreamt about it I never thought having Ann's hand wrapped around my hard cock could feel like this. She seemed to be relishing holding my erection. Her hand moved slow and gentle up and down my shaft. I decided to prompt her to greater action.

"Well what are you waiting for?" She raised an eyebrow once more and looked at me, "Prove you love penis!" I thrust my cock into her hand. She looked shocked but I think we both knew where this was already going.

She let go of my cock and it came pinging out of her hand to its natural position. I couldn't take my eyes off her movements. She threw herself off the sofa onto her knees. Undoing her shirt as she went, her eyes never leaving my body. She shuffled in front of me opening her blouse and casting it aside. My mind reeled. My best friend's mom was on her knees in her bra prepping herself to suck my cock. I was literally living the one of my favourite fantasies!

Ann reached round behind her to undo her bra, my erect cock twitched involuntarily.

"Oh," She teased, "you have been waiting for this haven't you!"

I nodded unable to speak. Reminding myself I needed this moment to last.

Her bra straps loosened with the clip undone and she dragged her huge bra off her and dropped sideways to the floor.

Her tits were nothing like I had imagined, but still incredible. They swung lower than I had thought they might and they were what porn had taught me was called missile tits. Her nipples were definitely erect and my hands went to her breasts quicker than I could think. They were prefect! Soft and fluid as I thumbed her nipples, I released one hand so I might point my cock at her mouth.

She grinned an evil grin and moved in. Taking my cock in her slender hand and guiding it directly into her warm mouth.

My whole body shot with ecstasy. My best friend's mom, the woman of my dreams, was giving me a blow job with no top on!

I caressed her huge tits and pinched lightly at her nipples as I felt the weight of her bust, she worked my shaft with her tongue, bobbing her head with a regular motion. A strange thought crossed my mind. If this was going to be my dream moment then I should do everything to make it just like my dream.

"Look me in the eye when you are sucking my cock Ann!" It was a command, not a request and she did just as I asked.

To see Ann with no top on, kneeling at my feet, throating my hard cock and looking into my eyes. It is THE perfect image of my life! She continued looking into my eyes as she sucked my dick, I drank in every detail and pushed her hair back out of her eyes whilst she worked. In no more than five minutes I felt myself getting close, unable to hold back the way I really wanted. I could feel the most powerful orgasm of my life building, I warned her.

"You're going to make me cum."

She pulled my cock out of her mouth, the suction audible as she released her grip.

"Where would you like to cum?"

She asked the question as a real temptress, tonguing the tip of my cock and drifting down to place two light kisses on my balls before coming back up and reinserting my slobber covered dick back down her throat. Gagging as she took a little too much down her throat.

Her head bobbed loyally as I quickly pondered the question. I acted as if thinking about it for a time as I ran my hand through her hair all the while she sucked, but I already knew the answer. In my fantasies I had cum on and in every part of her but I always loved the idea of jizzing on a woman's face. It's the ultimate alpha male action. Marking your territory with your seed.

"I am going to cum on your face."

I moved to stand and Ann struggled like a pro to keep my cock in her mouth, shuffling backwards on her knees to stay at the right distance.

As I stood over her I recapped some of the images of the best night of my life. Her playful smiles, the mental images of her and her gay friend, her ridiculous exclamation 'I love penis!,' seeing her breasts fall into their natural position, just seeing her breasts, feeling her warm mouth engulf my hard cock, the moment where she had kissed my balls, all of it.

With my rock hard dick aimed down her throat her eyes never left mine. I thrust my hips gently and she allowed me to very gently push my cock into her mouth. She lightly gagged but stayed looking up at me and I knew my moment had come. I pulled my cock out of her mouth and started wanking my dick with fury, aimed right at her stunning face.

She reacted perfectly. Placing one last kiss on my cock and rubbing my dripping tip all over her beautiful face.

"Ok, you ready?" I asked rhetorically.

She closed her eyes, opened her mouth and presented her face, tongue sticking out.

I unleashed the biggest load of cum of my life to date. Line after line of my hot white cum hit Ann's face until I squeezed out the very last drop. When the first line had hit her she had flinched but after that she had stayed exactly still as I poured it onto her. To my further surprise she opened her eyes when I had finished, despite being covered in my jizz, found my cock and sucked the last drops from my shrinking penis. Making sure I saw her gulp it down those last few drops.

"Well?" She asked. Her face plastered in my seed.

"Well what?" I managed out of breath.

"Do you believe I love penis now?" She asked placing small kisses on cock as it deflated.

"Oh hell yes!"

"Good, then I have proved I am not a raging lesbian?"

I couldn't think of anything else to say.

"I don't think a raging lesbian could give THE perfect blowjob! Thank you!"

"You're welcome." She said in honesty. I couldn't take my eyes off her cum splattered face. It was a perfect image.

Taking my hands I helped her get up and she walked off to clean herself up. Her enormous breasts bouncing as she walked off. I pulled up my trousers and sat back down; mind blown and barely functioning. The film was still playing. It felt like no time at all had gone when Ann walked back in. Face washed of my semen and a change of clothes to a night gown, she walked back in with a beautiful smile on her face.

She sat next to me with her attention on the TV.

"That was fun wasn't it!"

"Incredible!"

I couldn't help but ask.

"Are we going to be doing that again anytime soon?"

She looked thoughtful, playful and seductive whilst keeping her eyes on the film, slowly she placed her delicate finger to her chin.

"How about this..." She said slowly, "Every time you go out and fail to pull you can come back here and we can have some fun, suit you?"

"Fucking hell yes! But you realize that I am not going to try and pull as I have just had the woman of my dreams blow my mind."

"Well," She said, finger winding and playing with her hair, still looking at the TV, "that's up to you, isn't it."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
AnonymousAnonymousalmost 3 years ago

Hate alpha-males. Typical of them, they think a giving a bj is such an amazing privilege that there's no reason to satisfy her. She should get together with her friend, she'll have her first orgasm ever. And several more.

Sapper257Sapper257over 5 years ago
Marvellous

Well written. Every boys dream. Would liked you to go on a satisfy Ann. Woman have there needs as well. You have plenty of leeway to continue the series.

As I said a marvellous story. Keep writing, maybe bring in a Grandmother.

REgards

chytownchytownover 6 years ago
Good Read***

Thanks for sharing.

rightbankrightbankover 6 years ago
It's still a disappointing night

Until he reciprocates

What is he willing to do for her?

horney47horney47over 6 years ago
Well Done!

The story was well written. The story was yours to write - ignore the naysayers.

Show More
Share this Story

story rosa-blanca.ru

Similar Stories

After School Special Todd's mistake gets surprising results from Miss Ross.in Mature
Seduced by Best Friend's Mom Pt. 01 Best friend's mom is an MILF and she seduced me.in Mature
My Girlfriend's Neglected Mother Hot Mom, hot daughter, is anyone complaining?in Erotic Couplings
My Best Friend's Hot Mom Young stud bangs MILF in all 3 holes during hot summer day. in Mature
Mom's Best Friend: A Virginity Lost Nerd gets lucky when MILF seduces him after seeing his cock.in Mature
More Stories


"nudist families"" i knew what she " taboo "i.literotica"Temple lesbian Whores erotic storiesstreamsexrunaway mom and son taboo sexstoriesIncest story Mom and son. My mom lied my dad that am coming when i was fucking and cummed in pussy right. Ooh please finish speedly/s/skinning-the-cat?page=5"anal literotica"two mums two laps car sex confessionCelebsmutty,com"literotica thetalkman"hot igbo girl amaka loud sex storyquarantined with a crossdresser storyww xxx vibaos nicki minech comhusband concerned about wife's after work behavior /lliteroticaGiantess Linda shrinks him he fucks her thumbliterotica gay interracial travelA toorak robbery sex story"flashing tits"/s/incestuous-castingliterotida christmas with my brotherGiantess Linda shrinks him he cums in his pants as he went down her throat"literotica mother"Literoica Stories of guys underwear strip searchtaking what's his lieroticaমা ছেলে incest"literotica incest"mother son slow seduce with talk conversation.. indian Literoticai feel your cock pressed against my ass/audio/literotica.comindian literitica loving wife rupanita"literotica wrestling""very religous" "wife" "daughter" asstrwife christine kevin cuckold creampie husbandnatygutierez pornmovie mastrubationww xxx vibaos nicki minech comowengreybeard hookManipulating jenny Sex Stories"gangbang stories""erotic mind control stories""kristen archives"literotica twink my assholeFuckingmrsAVA"literotica incest"Litarotica.com, mom love bbc, caughtHero incest stories"literotica new""literotica pegging"LANCE AND HONEY ON A VACATION SEX STORIES CHAPTERaudio literica sluts fuck"literotica mom son"taboo stories literorticayour erotic sex stories,/ you fuck me in the kitchen wiggling my sexy big butts while you stare at my back/erotic couplings storiesstay with me son taboo sexstoriesStory of Amaka sucking Linda's breastunwelcome hypnofuck story"wife fucking stories"lost luggage porn stories"free sex movie"literotica gay interracial travelThe Grand Strategy taboo stories"literotica mom""literotic mobile"Successful incest literoticaliteroricaliteroticacom"first blowjob"Story of Amaka sucking Linda's breastaunt kidnap her niece sexstorymy body crushed beneath my son.. indian Literoticalyricsmaster family pregnant"literotica cuckold"literoitca she solicited me taboo i.literoticaஅம்மாகூதிlitrotica uncomfortable"fucking my cousin""hotwife stories"asstr sister prankIncest stories panty pop with grandpa"literotica mature"lyricsmaster loveseatTeacher teacher i declear sex story"literotica bdsm"Mother In a remote control app for a chastity belt bondage literoticasolitary confinement bdsm storiesfraternity willing pussy.literiticateacher+blindfold+blackmail+camera+bdsmlibrary"connie nielsen nude"