This story is a work of fiction even though parts of it were inspired by real-life incidents. Any similarity to real people, living or dead, is coincidental. All the characters are 18 years of age or older. Do not read this story if it is illegal to read about explicit sex where you live.
Edited by H.S.
I followed my usual routine at the gym. During my workout, I couldn’t shake off the encounter I’d just had with Kate. She and I met in the hallway of Madison’s condo building, and she happened to be Madison’s upstairs neighbor. Kate had made it known to me that she could hear Madison and me having sex, which churned up mixed feelings of embarrassment and erotic excitement in me. My new enjoyment of shame was a growing feeling of exhibitionism, and I was both mortified and turned on all at once.
Kate had told me intimate details about the dirty talk that Madison and I had engaged in, details that were true. And Kate had indeed heard everything, because Madison hadn’t had the chance to tell her. With the millions of dollars spent turning that old industrial building into luxury condos, you’d think that soundproofing would be a given, I mean, how could any contractor overlook such a basic detail? Well, it seemed the newest, swankiest condos in the old neighborhood had a dirty little secret: Sound carried very well-too well!
Kate was beautiful and sexy, and she had an incredible body. She was already a desirable element in my proximity, and now she knew I was having sex with her friend and neighbor. She knew we watched porn together; she knew I liked to talk dirty and liked to be talked dirty to; she knew we engaged in fucking, sucking and masturbation. And most of all, she knew Madison took my cock up her ass regularly. I just hoped she didn’t know how much I enjoyed Madison’s finger up my ass when I came.
Perhaps she was intrigued. Maybe she wanted to join us. Wow! What a thought that was! Imagine, two hot women at once! Kate could sit on my face while Madison rode my rigid prick, and then they could switch! Meanwhile, I was getting an erection, and the loose fitting gym shorts I was wearing wouldn’t be much of a help in hiding it. I had to talk myself down and get rid of that erection before anyone saw it.
The gym was busy, and there was someone waiting to use my bench. Just do another set, and your hard-on will go away, I thought, so I did as my subconscious said. I’d been doing bench presses and was almost done, but doing ten more reps did the trick, and I was able to get my dick to go flaccid.
Then I heard a familiar female voice say, “I’ll bet that was really hard.” Breathing in, I looked up to see Joanne, a woman I knew, looking down at me. I was hoping she was referring to my bench pressing and not my manhood. “Yeah, but I got the set done somehow,” I answered, hoping my fear was just groundless paranoia.
Joanne just stared. “It was impressive,” she finally said in her flirtatious way. I wasn’t really sure what she was referring to and was afraid to pursue the conversation. It was awkward, first, because Joanne was a friend of my mother’s, but mostly because she and I had been secretly fucking for a few months before I met Kerry. Of course, that was a little detail we both hid from my mother. Joanne and my mom worked together as waitresses at “The Mediterranean,” a famous restaurant in the old neighborhood. The place was an institution known and loved by tourists and natives alike.
Joanne was a divorced mother of two and didn’t do a very good job of hiding the fact that she was lonely and horny as hell. The talk in the old neighborhood was how Joanne had taken to sucking off her male co-workers for fun. I think in truth she had a few one night stands with some of the young, handsome waiters at The Mediterranean. I even heard she’d fucked two guys at once, but I wasn’t sure if it was true or just something the rumor mill cranked out. I could easily picture her happily deep throating some guy’s tube steak, still dressed in her black waitress uniform, however, and that sexualized her for me. I’d often wished I could be one of those men Joanne used sexually to fill the void in her life.
While she was just okay looking as far as her face was concerned, her body more than made up for that. It was built for sex, tall with nice breasts, but my favorite part was her ass, as I’m sure you guessed by now. Seeing Joanne at the gym in skintight Spandex was always a guilty pleasure of mine. There was something dark and sexy about her bolstered by her playful, cock teasing ways. She liked to flirt with me when my mother wasn’t around, and at the gym she would say things like, “Oh, my, you are looking super hunky,” or “I wish I was your age,” while she groped at my chest and arms. She was always touching or caressing my shoulders and neck, giving me long, lustful stares and winks. At first I thought she was just being nice, but it did cause me to think and have fantasies of a forbidden fling between the two of us.
Then bursa escort Joanne started telling me things like, “I’ve been so lonely since the divorce that I can’t get to sleep at night.”
I playfully suggested she get a teddy bear to cuddle up with, but Joanne, never missing a chance to turn the conversation a little bit risque, looked at me with a naughty smile and said, “Well, I was thinking about getting a toy, but a teddy bear wasn’t what I had in mind.” When she spoke, she drew out her words slowly, animating her lips and tongue in a show of oral control.
I let out a nervous chuckle. Her display had been intentional, to to tease me and make me hard. It worked, and she knew it. Any man in that position would immediately think of those lips and tongue expertly working over his dick. Well, I knew it was no secret that Joanne was very talented when it came to sucking penises, but I kept in mind that was the impression she wanted to give.
After that incident and the talk of toys I ran home from the gym to masturbate to the thought of Joanne peeling off her Spandex for me. I would have licked her sweaty cunt and asshole clean, then I would plow her ’til we both came. That fantasy masturbation session produced one of the most amazing heart-stopping orgasms I had ever had and one of the largest wads of come I had ever shot. However I remember the weird, guilty feeling I had when I was done jerking off. I was now ashamed of myself and promised to never jerk off to the thought of Joanne ever again.
It became clear that going all the way and fucking her should not happen. I knew that even if I got the chance I should pass on it. My instincts told me if I felt guilt jerking off to the thought of her, I would feel even worse if I actually fucked her. After all, she was my mother’s friend. That in itself would be strange, not to mention she was a single mother of two. At that point I had never fucked a pussy that had borne children. I wondered if it would feel the same. All of those things put into perspective and all the forethought about Joanne being forbidden fruit didn’t stop my lower head from overruling me. Against my better judgment, I had a brief sexual affair with her on the sneak.
The fact that it was a secret made it all the more fun. I guess it worked for me erotically because, like anal sex, the affair was interdicted. Joanne and I would act as if it was just us flirting and jesting one another but we both secretly were itching to act on all the joke offers and comic innuendos.
It took a while to come to reality because I still lived at home, and if Joanne and I were together it would be easy for anyone to figure out. So we needed fortuitous circumstances to fall into place. We had teased one another to set up hookup points and even joked of getting a room out of town, but unforeseen obstacles would always jump into the path of our rendezvous, usually Joanne thinking better of it and playing it off as if it were all a flirtatious tomfoolery.
It seemed we were always just joking, and I wasn’t really 100 percent sure if Joanne was serious, but the opportunity finally arose when Joanne was moving. She was a victim of the old neighborhood’s change. Some rich new person had bought the building where she was renting. Joanne had to find a new apartment.
When it came time to physically move her belongings, my mother, being her friend from work and not at all imagining the idea of anything steamy between Joanne and me, volunteered me. I helped carry mostly boxes of stuff since the furniture was already gone. Once everything had been placed in Joanne’s new apartment, she suggested that we have a drink somewhere.
Being under 21 at the time limited things, of course. Joanne bought us a twelve pack of beer at the liquor store, and we drove in her car to a little place called “no man’s land” by people in the old neighborhood. It was a deserted dead-end street that bordered an old, abandoned fishing pier on the far end of town, and if anybody kept driving straight they would land in the harbor. No man’s land had two things going for it: It was secluded enough to drink a beer or smoke a joint and there was also the harbor view.
We sat and drank beer and looked at the reflection of the moon shimmering on the waves.
Like most, after a beer or two I had to urinate, so I excused myself I found one of the many dark corners of no man’s land to pee in. When I returned to the passenger’s side of the front seat, Joanne asked, “Hey, where did ya go?”
“I thought I told you… to pee.”
“I know, but you hid in a corner.”
“Well, I thought I was finally going to get a glimpse of your bald-headed warrior.” She then burst into laughter.
“Sorry to disappoint you.”
“Oh, well…” she said with fake disappointment.
‘We do have more beer, chances are I’ll have to go again,” I teased through a devious smile.
“Ewww! Do you really think I want to watch you take a piss? Yuck! I bursa escort bayan was kidding.”
“So was I.”
“I know. Now, get back in. It’s cold.”
“My ex and I used to watch porn together, and one time he got this one movie where the performers took turns pissing on each other.” She made a dissatisfied face and shook her head. “I’m not judging anyone … it’s just not for me.” I realized it was a detail that she wished she had kept secret. We talked openly about sex in the past, and she would tell me about her ex, and sometimes would tell me things about their sex life. But this time she was telling me something about her sex life in order to let me know that she wasn’t serious about watching me pee just to get a peek at my manhood. She let this bone out of her closet and handed it to me, rather than have me misunderstand her and think she was into something that exotic.
Did that mean she actually cared what I thought about her? Did Joanne seriously want to see me naked, or better yet, did she really want to fuck me?
“Okay, okay,” I said, once seated in the passenger seat with the door closed. “How often did you guys watch dirty movies?” A true inquiry, I loved porn and wanted to see more of it, and never having been in a long-term relationship and wanting to know the secrets the average couple would keep. What was the norm and what was on the edge, but I also wanted to get sex onto her mind.
I wanted our conversation to be of sexual nature. I enjoyed talking about sex with Joanne.
we had risque talks in the past and I had always enjoyed them. It was a way for me to get a cheap thrill. Those conversations laced with flirting and innuendo stirred me up. I would always play it cool and be try to appear nonchalant about it, but I really got off on it. Still, there was also the motive in it for me, thinking that if our steamy little chats could lead to Joanne getting as horny as I secretly did during those conversations. That maybe it would lead to something more.
The desired results were finally achieved, but not before my question took us on a detour down a sad path for her. “Who? Watch dirty movies with who?… You mean my ex?”
“Yeah … is that something married couples do often?”
“Yes, and we did it whenever he wanted to… I did whatever he wanted …when we were in bed, our finances, about how to raise the girls, I did it all, everything he wanted, because I wanted him to be happy…because I loved him and… and still do.”
It sounded like she was fighting back tears, both from the still open wound and from that melancholy feeling that alcohol sometimes brings.
Joanne was getting buzzed from the beer and getting emotional about being divorced and having to move. She leaned into me, wanting some contact. I had hugged her before in support of her emotions, and I guess we had a weird touchy-feely thing going on, but we’d never crossed the line.
I thought it was mostly platonic and acted as if it were, but secretly I think we both loved the feel of each others embrace.
It may have been her sadness, or she may have just wanted to feel good again that night.
Whatever it was, when I hugged her, we held each other a little longer than usual. My cheek brushed hers. I hesitated. Could it be? I thought.
This is weird, I thought.
This is a friend of your mother’s; she flirts to be nice; am I getting the wrong impression? I thought. I was frozen for a second. What if I kiss her and I’m wrong? Would she slap me and go tell my mother?
But then she would have to explain why she was down in no man’s land drinking beer and snuggling with her son. Worst case, she would pull away and say no and keep the secret between us. However, the best case might mean I could finally discharge all the come that my testicles had brewed up from her tempting me. So, after all the flirting and touching , the sexually-tinged conversations and her all out cock-teasing, I figured I had earned a pass.
If I tried to kiss her, she would have to take her own actions into account.
I mustered my courage, leaned over put my mouth to hers, and just like that we started kissing. Still, it was a bit strange. This was a friend and my mom’s co-worker. I think she was 38 at the time, close to my mom’s age. It felt surreal, and it was surprising. But I guess all the flirting and touching between us made me want her even if I wouldn’t admit it to myself.
She began to nibble my neck as we kissed., and the hot breath and soft mouthing on my neck got the desired result. Joanne then licked and blew in my ear, and it sent me into overdrive and made whatever patience I had disappear. I aggressively ran my hand down to her crotch. I rubbed her vagina through her jeans, and I could feel the ready, swollen lips of her twat and the soft mound of her pubic hair through the fabric.
I also thought perhaps I shouldn’t waste time lest Joanne change her mind and not give in to my advances.
I escort bursa found out she’d caught her husband Ronnie eating out the nanny’s pussy on top of the washing machine during the spin cycle. She threw him out. He never begged for forgiveness but just got a place with his “Swedish nanny whore” (as Joanne referred to her) and told mutual acquaintances that he and Joanne had separated.
Partly because she was lonely and partly because she wanted some twisted form of revenge-but mostly because she liked to fuck-Joanne wielded her new sexual freedom like a bank robber wielded a gun: Often getting away with what she wanted. It didn’t make her a bad person to me, just a loose woman who liked sex and had low inhibitions and even lower standards.
I could see her getting it on with two guys at once. Maybe even three!
Her friendship with my mother was the wall that had impeded this encounter. My mom tried to counsel her to slow down and wait for the right man, but Joanne wasn’t having any of that. She wanted revenge and she wanted sex, but most of all she wanted to feel better and move on from her nasty break with her cheating husband.
I moved to unbutton her pants, and she didn’t stop me. But then the zipper of her fly got stuck.
“We should stop,” she said breathlessly.
“Really? We’ve got each other going. We’ve come this far. Why do you wanna stop?” I argued with my rock hard member threatening to bust my pants wide open.
“I know, but…”
“But what? Are you afraid of my finger?” I demanded, implying that heavy petting and fingering her snatch was as far as I would go. But deep down, I knew that if I did a good and thorough job of finger banging her, she would beg for my shlong. I didn’t have any self confidence at this point. I didn’t see myself as a ladies man or Don Juan; I just knew how incredibly horny and prick hungry she was. I thought of Joanne as a promiscuous slut. After all, she loved to fuck and suck and was almost always horny.
“This is a sign,” said Joanne, sounding like someone full of self doubt and cold feet as she struggled with her zipper.
“No, it’s not. Just flatten it out.” I said, referring to her zipper.
“No, we should stop,” she said, looking up to the roof of the car as if gazing right through it straight to the heavens. She was truly doubting herself and her judgment and almost giving in to the thoughts of how inappropriate all this was.
I was starting to lose hope. Disappointment seeped in like cold water. But I pushed back, being already committed to the idea of it and my lust already sparked into an inferno that saturated my balls with piping hot baby batter. I still wanted something, to play with her pussy and maybe a hand job or a blow job. Anything. Something! Please!
Pressing the issue, I did my best to convince her: “You want this. We both want this, please don’t leave me hanging,” I pleaded, not wanting to leave blue balled by a woman yet again. She let out a nervous sigh of resignation and with some effort undid her pants the rest of the way.
I pounced on her like a lion, so worked up and nervous was I that it translated inadvertently into rough play. I slid my hand between her legs and jammed two fingers in her waiting cunt. I forced my tongue into her mouth and kissed her vigorously and hard. The speed and energy that I fingered her twat and rubbed her clit had her gasping for air. Looking back, a more experienced man would have realized that Joanne liked it rough. She was content to be brutally finger fucked because in her mind it somehow made her feel less guilty about fooling around with her friend’s son.
I pulled up her sweater and bra, and her right tit sprung free. I sucked on the nipple of her one exposed breast so hard she let out a small yelp as I continued to thrust and withdraw my fingers from her steaming snatch with high speed. I moved from suckling her breast up to her neck and softly whispered to her: “I wish I could fuck you.” The words spilled out of my mouth involuntarily, as if what I’d been thinking was broadcast without my permission. I was surprised to hear myself say it! I was afraid I might lose her if I suggested we move to the back seat, given the limited space in her car and my inexperience, so I resigned myself to the idea that maybe just heavy petting would be the extent of this encounter. Still, I guessed it was best for her to know my true desires, and, who knew, maybe we would find a way to go further.
“I really wish I could fuck you,” I moaned again, like a tomcat in heat.
“I would love for you to fuck me,” Joanne answered to my surprise. “I want to slide my pussy up and down your body.”
Well! A full-body pussy massage sounded wonderful and original, the dirty talk heightening an already hot moment. She reached over with her left hand and rubbed my throbbing penis through my pants while pulling me closer to her with her right.
“I would love to have you inside me, deep in my pussy,” she said longingly.
“I’d fuck you very hard,” I managed, now awakened to my own carnally induced ramblings. Yet I began to feel inhibited, and I was ashamed of my previous dirty talk even though I wanted to express myself.