Free Erotic Stories

Helping a friend

When I walked into the coffee shop Lisa was in the comfortable ‘big’ chairs with her BFF Sharon. My choice of casualness became my shame. Dressed in old denim, flip flops and a hoody I had not done much in order of appearance. Brush teeth and throw on clothes and head across the street to the shop had been my preparations to see Lisa, but Sharon was a different story.

Sharon is a College Professor in Computer Modeling, off the charts smart and bold in her intelligence. Tiny and feminine on the outside a tiger on the inside. Only five-two and about 110 pounds she has full lips complementing a perfect set of pearly whites and golden green eyes and the highest cheekbones possible, all hidden by huge glasses and dark curls down to her shoulders. I longed for the day Lisa would say ‘Chas, she’s really into you’, that has never happened and seeing her reminded me why. At 7am on a Saturday she is perfectly coiffed and I’m an unwashed mess.

I grabbed a cup, poured black coffee, acknowledged my barista friends and headed to see the ladies. Lisa chose her clothes by her relationship moods and today was black, ubiquitous, Lulu Lemons tight as screws covered her long legs and shapely ass, black sleeveless tank showed her ivory Irish in contrast. With no make-up her freckles pop and she looked forty-two not fifty-five.

When I approached I knew I had broken a conversation not meant for a man to hear and when Lisa hugged me tight her hard nipples rubbed against my flat torso. Lisa and I have never been intimate but have seen each other nude many times in hot springs or nude beaches. A friendship that has lasted almost forty years is almost as comfortable as the one I have with my big sister.

Sharon didn’t stand and barely acknowledged my presence with a meek ‘hi Chas’. After the moment of awkwardness and platitudes Lisa broke right in with ‘how can a man without any skills in bed get this far under my skin?’ Sharon and I looked at each other and broke into laughs.

Lisa has had too many men to remember them all, but one thing I do remember is how she categorizes men. The ones who can’t ‘perform’ up to her high standards of sex drive, creativity and risks get kicked. She finds the ‘over achievers’ egomaniacs and the ‘wonderful lovers’ to be clingy. She unloads on us with news of the latest, his intelligence, great looks and control. Lisa has never been one to ‘need’ a man and this one was able to push buttons to get her to please him in many aspects of life. For her it all fell apart in bed, the leader of a large tech firm with great power and wealth, she assumed this would translate into a great sex partner. But his tiny penis and low stamina seemed to diminish his gravitas. The final statement was ‘four months, not one ‘O’.

That statement shut me up and Sharon let out a sad ‘OH’. The three of us sat silent, I was waiting, this seemed like territory I was prohibited from entering until Sharon shyly said “Chas, this is your turn to help us’

‘I don’t know what you want from me’ I replied

‘What do men want?’ Lisa demanded.

“In bed’ Sharon added.

‘Me or other guys?’

‘Aren’t you all the same?’ Sharon inquired.

I thought for a moment before launching into the abyss. ‘Most men it seems to me think of sex as the dividing line between ‘courtship’ and ‘done’, what I mean is they think once the physical has started the courtship or challenge is complete. Then their partner becomes another object to impress others and not the complicated, uneasy and insecure gift that needs to be unwrapped layer by layer. Lisa, you know you’re hot, I’ve told you that a hundred times since college and you look better today than you did years ago. This guy may have liked being the center of attention, before you and with you it inflated his self worth even higher. I hate the term but ‘trophy wife’ is what a big group of men seem to desire’.

Heads nods in agreement pushed me onward. ‘If you’re looking for handsome, smart and sexually adventurous I’d probably suggest dating apps that admit upfront SEX MATTERS. I use a couple, however, being single, white and male means it’s a time drain and only a couple times have I met women truly free sexually but they are not looking for a serious relationship, more friends with benefits, specifically exploring sexual taboos’.

‘What taboos?’ Sharon let out quicker than she wanted and a red flush showed on her high cheeks. We all laughed.

Over the next hour and three cups of coffee the three of us talked about sex. Taboo’s, kinks, fetish and positions. Men’s endowments and how little importance they mattered if fantasy and openness about sex were part of the equation. The ladies had question, I had questions, they had answers and I had answers for them and I was rock hard!

Lisa next statement and question left me speechless ‘we’ve known each other all these years and yet I never knew you had these kinks and you were chasing woman for wild sex. Have you gotten to live out all your fantasies?’

‘No one gets that’

‘Is there one you still think you’d like to try?’ Sharon asked breathlessly.

‘Of course’

‘Chas you’ve got to tell me!’ Lisa exclaimed.

‘It would be too embarrassing’

Giggling like a school girl, this woman of great intelligence said ’Alright just give us a mild one, maybe we can try it out on the next guy’

‘I can’t’

‘Can’t or won’t?

‘Both’

‘Because of me?’ Sharon inquired.

‘Yea that’s portably right. Lisa and I have talked about just about everything and she’s seen me in love and in lust, but…’

‘He’s always had a thing for you Sharon’

‘That’s not even fair, Lisa’

‘Tell her. He thinks you’re and I quote ‘sex on a stick’

‘Hey! That seems so inappropriate and I apologize Sharon, I said that after a couple of cocktails and..’

‘Is it true?’ Sharon asked seductivly.

‘Well you are ‘hot’

‘But sexy?’

‘Of course’

‘HHMM, so do you fantasize about two woman and you?’ Sharon asked.

‘Not exactly’

‘Chas, I want details!’ Lisa demanded.

I took a moment and looked around the shop. Baristas busy somewhere else and customers at the other end of the long lounge area. I had told details to Lisa before about sexual relationships but in front of her friend I was shaking with tension. I said fuck it to myself and plowed ahead unafraid of the consequences.

‘Two women, a transvestite and me, lightly bound and blindfolded and lots of toys’

‘OMG’ Sharon exclaimed.

‘Chas, we need details!’ Lisa

‘It’s fantasy the details are sketchy and depends on what everyone wants’

The baristas looked our way when Sharon shouted ‘I wanna be one of those women’

The laugh that made me notice Lisa the first time unleashed upon us. Infectious and booming, masculine almost, throaty. All packaged in this unbelievable body. At twenty she stood out from the frat party crowd with that laugh surrounded by testosterone filled masculinity.

Patrons of the bean bar today, noticed her before she laughed, men and woman, she stood out. Five-ten legit, six-one in heals a swimmers body at fifty-five, diet and skin care. Women lust, men drool, including the college guys that entered during our erotica.

We had been talking like this for ninety minutes on a Saturday at nine am, it’s not a conversation I wanted to continue in a busy coffee shop. I excused myself to use the restroom and catch my breath.

I was trembling, leaning against bathroom wall, cock in hand, hard enough to be a problem in getting out and peeing. The thought of Lisa knowing is daunting. I’ve got to go back out there so I can’t jack off, Lisa will know right away. She caught me a few times in college and when she stayed with me after her divorce.

I’m filled with relief like a gay man after telling parents about his sexuality. Now I’ll find out of the consequence. Lisa has been the best female friend I’ve had, we’ve never ‘slept’ together. We have slept in the same bed, did light make-out sessions when we drank too much, she’s seen me naked, I’ve seen her naked. This is new territory, the conversations before about our separate sex lives are basic. Who, what, when, where, why and how.

The guys Lisa slept with when we were young were athletes and generally big dudes. She’d have a new one every month. The banking business required too many hours, boring husbands looking to cheat, conservative fashion and the occasional after-hours social event requiring a male ‘date’, me.

Lisa went from one guy a month to one every six months. Yes, married but always powerful. Banks, brokerages, unions, school districts, Lisa sold to them all. The men ran huge sums of money and discretion to buy as they like. She told me that sometimes she’d question herself. Was she having sex with a guy to get his business and if she was she a ‘hooker’ albeit one paid $10,000 an hour.

A sexless marriage to a closeted gay man who wanted children. Now it’s a new guy every two years. She’s too hot, physically, you toss in the smarts, career, money, it can be intimidating. A big Mercedes-Benz, townhouse on Lake Shore Drive, the view from up there! I try to imagine if I were dating her what that feeling would be like, walking into her life.

It makes sense she ‘dates’ huge guys, physically or success-wise. I love her but I think I’d need three little blue pills to get it up in her house. A guy who makes a million dollar deal every day probably isn’t intimidated by her success. The forty year old ex-NFLer she dated last year had no problem with the big MB, he had four, but he cried after sex. The sex was really good, at least for her.

I’m done. I can’t this any longer. I’m not going to be able to pee in this state. The return walk is terrifying and crowded. The place has filled-up with pretty young faces, moms in stretch pants and kids with sippy cups. My chair is tucked up close to the table and the ladies have moved up close. Two ‘dudes’ all handsome and young, thick with muscle sit to close, gawking at Lisa. My coffee is empty and I lean in and say ‘I’m out. I’ll..’

‘You’re not going anywhere mister’ she can intimidate me.

‘OK, but we have to change the subject’

Two days later Lisa called while I was writing and the call that went to voice mail told me to meet her at our favorite happy hour.

I was a mess, again. I showed up at the bar at 6 PM and the business men and women had been showered and shaved, groomed and plucked, outfitted in designer suits and silk, since 7 AM. I arose sometime between 9 am and 10 am, I’m never really sure because I start typing right away. Four day old stubble, no shower, dirty jeans, flip flops and Led Zeppelin T-shirt are the dress of the noble artisans.

The big kiss and hug I get from Lisa upon entering garnishes me with the evil eye from the men and questions from the women. I always get the big hug and kiss but this is different, like the day she told me she bought the townhouse or the time she slept with the famous movie star I didn’t know. The table was set with a bottle of red and two glasses, mine full, hers half. We pulled away and sat down. I asked ‘what’s up?’

‘Nothing, I just wanted to see you’

‘Lisa, the hug, the Patz & Hall Pinot, the urgent message to meet…’

‘We want in’

‘On….’

‘You know, what we talked about Saturday’

We can’t do this here

They all notice her and because of that I get noticed and I’ll go red if we talk about what I think she wants to talk about

‘How about I ask closed ended questions and you can answer yes or, look at me, or no, you can even nod your head, if that helps’ Lisa demanded.

I replied ‘You’re an awfully good sales person’

‘I know, question one, can I be there, quit shaking your head and let me ask my question, I’m there as a watcher only and kinda like a protector, would that be OK?’

I struggle with words ‘my fantasy? Or really happening?’

‘Oh! This is going to happen, I’ve never seen Sharon so turned on.’

‘She’s ‘in’….I did in air-quotes’

‘Yea, I she already found a gurl, I think that’s how she pronounced it.’

I sipped my wine and my mind whirled and not from alcohol. I came out of the momentary gaze too…

‘Chas, she likes you, never before has she said anything about you and then today it’s like ‘when did he get so hot?’ ‘Do you think he’d want me to help?’ Like you need help, it sounds to me like everyone is going to help herself to you’ and then the her laughter brings stares, men lick lips and women’s push-up bras go outward and higher.

‘Lisa, can we talk about what I said and are you and me still good friends?’

‘Yes! Probably better! You do know girls talk, right? That’s what it felt like when I thought about it later’….giggling she asked ‘would you really do it?’

‘I think, I’ve gone to clubs and done stuff before, mostly with women who like two guys and once a whole room full of naked people’

‘I never knew’

‘No’

‘Why?’

‘It’s scary, the labels and embarrassment of you know, being different .’

‘How long?’

‘Long.’

‘At Iowa?’

‘That’s where it started.’

‘That woman, Breezy or something?’

‘Beezy, yea she introduced me to kink.’

‘I knew it! Now there’s a freak, you know that chick made a pass at me in the showers.’

‘Not surprised.’

Who else?

‘From school?’

‘Yea.’

‘No one else it was just her and her equipment, then the internet opened up so much, since, maybe ten times.’

‘This is so weird Chas, I’m so turned on by the whole scene, I signed up on this website with two pictures and I’ve got a million people propositioning me into all kinds of crazy ideas.’

‘Pictures?’

‘Yea, one of my breasts and one of my legs.’

‘Any face?’

‘No, I have a job! My point Charles, is I’d like to be your ‘mistress’ meet the participants before, make sure they know and obey rules, watch, never touch, well maybe a little’ I got the big wink and as she looked to her mid section ‘who knows, maybe I’ll find a new way of life.’

‘This is so strange.’

‘So the clubs? Here in Chicago?’

‘Yea?’

‘Can I go?’

‘You’d be the belle of the ball.’

‘Ow. I like that.’

‘The attention or multiple guys?’

‘The attention, can I tell you what I’ve always wanted to try?’

‘Another woman.’

‘How’d you know.’

‘All your friends are gorgeous.’

‘I’ve been secretly picking female lovers?’

‘Not exactly, more like an appreciation of the female form.’

‘Damn you really do know me.’

The extra bedroom contained boxes, old books, all kinds of paper correspondence, clothes, mostly barely worn and expensive. Lisa spent the next week filling closets and shelves with stuff and shredded tax returns from the nineties. In the end she had four walls and wall to wall carpeting. She had a twin mattress on the floor, close to the four corners, hooks were screwed into the floor and attached were fluffy, soft pink handcuffs. The ceiling contained two more hooks with chains extended to a couple feet above the bed, on the end of the chain, two more pink handcuffs.

Scattered about dildos, strap-on belts, anal balls, things I had never seen, things I didn’t understand and one for me, a cock ring.

Neither one of us could get full sentences out, nerves and stress sweat on both our upper lips our friendship had never been so silent and wordless. We stood in the doorway for an eternity until our hands touched and when I looked at Lisa she said ‘I need a shot’

‘Ditto.’

At the granite counter top Lisa poured two glasses a quarter full of Tres Agaves Tequila. We held our glasses in the air and she said ‘to the best friendship ever’

An hour later the first knock made me jump. Lisa had changed into heals that made her even taller, silk and red, garter belt, bustier, nipples exposed and pinched with tiny metal clips. She was smooth and hairless, electroalist ten years ago, blonde hair in a sexy ponytail with wisps of hair falling over the green eyes. My friend brought Sharon into the bedroom and I wanted to die.

My hands cuffed in place, blindfolded, my legs in the air held in place by the soft handcuffs. My legs spread far enough apart that my mangina exposed twelve inches off the ground. My hard cock at full attention ready to explode except for the cock ring. Lisa didn’t tell me Sharon would be the first to arrive as she tied me in place. When she had me in place she bent down and kissed me full on the mouth extending her tongue and swirling. She put her hand on my chest and said ‘you’re hot and I’ve got to mastibate for the first time today, hold on just a minute, they’ll be here soon.’

The first indication was Sharon’s voice ‘oh my god, this is really going to happen.’ The second indication was the moist panties on my mouth, I tied to bite them off until Sharon pulled away and said ‘Lisa already had to finish herself once, I’m going to try and wait for the others.’ She didn’t have to wait long.

Lisa announced ‘say hi to Trixy ladies and don’t be jealous of her boobs, she got to choose them and she’s not going to need a strap on, look at that she’s very excited to see you Chas.’

Aw oh

‘And this here is Amber, and over here one of my closest friends Sharon and on the floor is Chas. Now a couple things, no humiliation, pain is a no go and if Chas says stop, we stop. I think that’s about it, so if you want to disrobe or…’

Before I heard the last words the same panties were in my mouth, even wetter. I heard Sharon utter ‘pull em off with your teeth’ I did as told and sunk my tongue deep into her wet vagina tasting all her love juice and then settling on the challenge of her clitoris. Hard and slippery her clit was the size of the tip of my pinky. Sucking on it made her squeal and push closer until I was having trouble breathing from my nose and continue sucking.

I could feel hands all over my body and the sensation was like nothing I had ever experienced. Two hands rubbing my legs from top to bottom, a single finger gently swirling my asshole, another playing with my hair. The first surprise was the mouth on hard cock. “We can have him inside us, right?’

‘I guess so, Chas would you like to be the giver of intercourse, also?’

Sharon would barely let me answer in the affirmative and just a moment later she yelled and her vagina opened up and a waterfall ensued. Her juice filled my mouth and over my chin and cheeks, warm and sticky, if it was possible I would have come myself.

My manhole was being lick, nuzzled and swirled and the actions produced sensations in my belly and of being breathless, at the same time Sharon lifted her scent from my mouth and anal balls were inserted slowly into my ass, ball one, my head rolled from left to right in pleasure, ball two, a new vagina, full of hair and very well used landed on my face. Lisa had found a friend of a friend who loved to be gang banged and wanted to try a reverse bang, this vagina must have been hers, ball three, I feel a mouth close over my cock, ball four, oh I’m full, ball five and the vagina on my face explodes, ball six and I have to pull my ass off the mattress and the pussy is not getting off my face. Squirting all over my face and chest, the warmness calms me, until.

Until they start to pull the balls from ass. As each ball comes through my rectum a sensation of orgasims jolts my midsection. From the opposite direction they come. Ball one, I think I came, ball two I’m sure I came, ball three and the object rubbing on my lips is not a vagia, IT’S COCK, ball four and I know I’ve come, Ball five and I get a full mouth of the that tangy flavored cock, ball six I’m shaking and I’ve got seven inches of cock stuffed down my throat getting hard and large.

The mouth that was on my cock has been missed until Sharon bends next to my ear and whispers, ‘I’ve never had a cock that large in my mouth, now it’s my turn. But I have one question first. Chas, have you ever had a cock in your ass? I see one in your mouth, come on honey tell me the truth, will I be the first?’

I can’t answer my mouth is full of cock. She continues ‘come on now, tell me do I get to bust your cherry, let me have that ass, you’ve got to say it Charles, say you want me to fuck you, hard and long, say it!’ I push with my tongue and get the cock out of my mouth only to scream ‘fuck me Sharon, take my ass, take my virginity.’

Apparently this is the funniest thing ever uttered because everyone is laughing and the loudest laugh is half muzzled in passions, I can hear Lisa laughing and coming and at the end she said ‘number two’ and I hear more giggles and laughter.

Trixy breaks the mood with ‘please suck my cock with your soft lips’ and the attention went elsewhere in the room. I’m lying there, legs in the air , hands behind my head, seven inches of cock in my mouth and I can’t feel or hear anyone else, did they leave me? Then the sounds are unmistakeable ‘no, a bigger one. Lube, make sure to lube it up, you’ll tear him, god that’s hot honey.’

The huge ball sack rests on my chin as Trixy has turned around and decided to fuck my tongue with her asshole and I can feel her hand tease mine. She does this thing about an inch in that drives me crazy but gets my tongue to lash her asshole and before I know it I hear ‘OMG, I’m coming’ and seconds later my chest is hit with hot sperm, it puddles in my breast plate and a female hand rubs my torso with the stickiness.

The lady fell forward giving me air to pant and suck oxygen. Someone is still playing with my ass and I can feel someone coming close to my legs, then hands rubbing the backs of my legs, from ass to ankle. ‘Ladies look at his feet, they are perfect like a girls after a pedi’

‘Trixy you like sucking toes?’

‘Sure, while you take his virginty, Sharon.’

I lost my virginity to the woman I’d jacked off to in my dreams. The blindfold prevented me from seeing her enter me. Trixie sucked my big toe like it was a miniature cock, her hands all over my leg. Amber’s ass to far from my tongue , I could feel her body on my lower torso and her tongue licked my balls, cock and rubbed the area around my hole. Sharon had the tip of her cock rubbing the same are as Amber’s finger. I was going out of my mind, my body was electrically charged, an unsettling feeling in my stomach from Amber but mostly from the fear and excited of the moment.

Just then two other hands grabbed my other leg and Lisa throated barely audible ‘Chas, it looks like the fantasy is coming true, I’ve got watch, fuck him Sharon, slow and easy.’

And that’s what she did, inch by inch, if this is how women feel when being filled I could see why the mouth makes the O, mine did and my squeal of delight made the ladies giggle in unison, Lisa’s was the loudest. Sharon laughed and her cock vibrated inside me and my hands grabbed hold of the mattress for dear life, my back arching in pain and pleasure. The darkness so complete my mind’s eye is of those dark curls, the rack I longed to see, wishing Amber would get off my chest and Sharon would come face to face with me as she took me. Too quickly she pulled out and that brought another wave of tingles through my body.

Amber got off my chest with a rub of her pussy and ass all over my face, my tongue had no chance to catch up. Lisa and Trixie let go of my legs and the room got quiet, my heavy breathing the only sound I could hear, minutes went by and I became engulfed in the exposure of slutness. Used felt good, so far.

Lost in these anxious moments, it was the sound of Sharon in obvious state of mind blowing orgasims. This educated and decorated professor, words forced from her by passion ‘oh god, oh my god, shit, shit, oooohhhh aaaahhhhh’.

Sounds from another room, they left me alone? It made me want to please even more. The room got quiet again, except of course my heavy breathing, then laughter from the ladies and clearly movement somewhere in the apartment. Voices echoed and I knew they were in the kitchen, just outside the door from me. ‘One, two, three’ came Amber’s voice and then glass on granite and hoops and mmmm. They did a shot without me! And giggled and talked about Amber blowing Sharon, I was so jealous until Sharon said ‘fucking him was the best feeling ever, sexual and powerful.’ My jealousy faded and pride welled up.

Lost in that thought, then hands all over my body surprised me, everywhere and one long experienced finger in my ass. They removed the handcuffs, moved me to all fours and locked me into place. That long finger massaging something inside me, had me shaking my hips. Amber pulled my head down to her pussy ‘do better than I did to your girlfriend’

Licking pussy and ass, sucking her growing clit, she gave me very specific instructions until ‘now you’re gonna lose your ass to real dick!’ The finger came out and in came the huge head of Trixie’s magic. It stretched me and when she buried it I could hear ‘wows’ and a ‘cool’. Trixie fucked me hard, then slow, deep and on the edge an inch in an inch out. Minutes went by, feeling overwhelmed and my tongue becoming overworked I sucked as hard as I could on the clit until Amber started to shake, convulsions and jerks until her pussy split in half opened up the fluid spilled onto my chin. Amber in the state of ecstasy was vocally pushing very ounce of orgasims out of her body. That brought a grunt from my backside, the heat in my ass gave me warm and joyful feelings. The power of the come would have pushed me to orgasims if I didn’t have a cock ring on.

Amber was no longer in front of me and I got up on all fours, the cock still buried and pulsating in my no longer virgin ass of fake cock, real cock or sperm.

Trixie wasn’t moving and her hands held my hips in place. Two heads touched my thighs and I could imagine all eyes on my ass as Trixie removed seven inches slowly, cum ran down to my balls and lingered in small droplets until falling to the mattress, when she pulled the engorged head out I melted, face and chest buried in the mattress, my ass was spread and dripping, high in the air. I was alone on the mattress and the swat on my ass was so unexpected I moaned a cry.

The paddling went on, dildos, fingers, vibrators all took turns on my butt. They smeared the dripping come over my ass cheeks. Each smack of the riding crop electrified my body, the fingers felt erotic. It seemed to go on forever. I was close to passing out when they unlocked me and put me on my back, undid my cock ring with great care, cuffed just my wrists and watched my cock spasm and release tiny pre come droplets. The mouth that tried to take my whole cock chocked and concentrated on my engorged head, in seconds I was convulsing, spurting shots into her mouth until she couldn’t take anymore and her hands jerked more waves into the air. I could feel my own sperm hitting my chest and chin.

My heart beating out of my chest, I was spent and my body had melted into the mattress. I don’t know how long I was out, however when I came too I was unchained and able to see. I had a weird feeling of having been licked clean and when I rolled my head to the left Amber and Trixie were seated on the ground, backs against the wall, both mastribating. I watched for a minute and then rolled my head to the right and Sharon was in the same position staring at me with lust in her eyes. Seated to her left and upon a dining room chair was Lisa.

Her head was thrown back, eyes closed, two hands on a huge black dildo, pumping herself. I looked down to see my erection had returned, the five us had a rumbling session of mutual mastribatuon, all coming within minutes of each other. I was the first to finish and Lisa the last and the loudest. When she pulled the huge dick from her, my mouth hung down in astonishment and she asked me ‘twelve inches next?’ And rubbed the glistening, pussy juice over the massive piece.

We hugged, laughed and reminisced over shots of Patron Gold, naked at the granite island, luxury and sin all mixed together. I was the center of attention and the compliments and lip licks told me I did my part in living out fantasies for myself and others. Lisa and I put on robes when the others had left. We made a fresh pot of coffee, we showered TOGETHER as the coffee brewed.

On the couch, we decided friends forever! I asked about the biggest dick ever and she giggled and said ‘Chas, size really doesn’t matter, today has been the best sexual experience of my life, a guy with a 12’’ cock get me off but this was truly erotic, and that, I’ve never know.’