If you’re lucky, there are one or two encounters in your life where the sex is so awesome that just by thinking of it you can practically get off anywhere, anytime, no hands required. I’m a very lucky man, as I have a catalogue of more than a dozen of these times. But there’s one that stands out in my mind.
I met Cass in a Vermont coffee shop a few years ago and we became fast friends. She’s had a complicated life, (and that plays into this story a bit, so I mention it). When I met her she was recently divorced, free again, and back “home” for a while to lick her wounds and move on. We are in the same field and know a bunch of the same people, and go to many of the same professional events. Shortly after we met, though, she moved to Oakland, and I thought I’d not see her again.
More than a year passed before I found myself at a conference with her. Dinner ended with drinks, which ended with flirting, and that led to her inviting me up to her room. Cass is amazingly cute. Short, curvy, with an immensely warm hug, eyes that always smile, and pale with the kind of skin that flushes bright red whenever she’s embarrassed, tipsy, or amused.
We fucked five times that night, and amazing as it was, that’s not what I’m writing about. Though… I still remember the shower where we washed off after the first time we had sex, foolishly thinking we were done for the night. She backed up against me, put my hands on her breasts, and ground against my cock without ever letting me inside. Just teasing at the edge for what felt like hours, but was only a minute or two. I wished like anything that they made condoms that were convenient to the shower.
Again, though, time got between us. We did write to each other, and we found ourselves on the same mailing lists, Twitter, and all of that. We remained friends, but we drifted a bit. The Bay Area really suits her, and finally away from her family and all her old problems she really began to soar.
When I finally caught back up with her, it was at a conference in Vegas. My wife, Lindsey (we’re in an open relationship, always have been, in case you’re wondering about that) was with me, because it was Vegas and she’d never been. Cass was standing at a bar flirting with a cocktail waitress who is making something complicated for her. She looked so different. I couldn’t really put a finger on it, other than a new haircut, but she looked so much more confident and well… happy.
“Cass!”
“Stephen! Hey! Didn’t know you were at this shindig. You’re looking great! You must be Lindsey!” Cass was all smiles and exclamation points, and her happiness shone from every pore. It was clearly not just the cocktail. She was *radiant*.
“That’s me! I’ve heard a lot about you.”
Small talk ensued for a little while, but Cass and I had lots to catch up on. Eventually Lindsey bowed out, “Hey, I’m going to mill around and see the sights. This is a hell of a place! I know how to have fun by myself. You two catch up!”
We walked around for awhile, talking and drinking, gossiping about colleagues and sharing work war stories. We eventually ended up sharing one big leather chair while Cass told me all about her new life out in the West. “So, I’ve met someone. A woman, actually. We’re keeping it open for now, but I think that won’t last.
“She’s amazing. I know you and I haven’t talked much in the last while, but you’ve always known I’m bi. I’ve actually… well, sometimes I think maybe I’m not bi. Maybe I’m just plain old lesbian. Every relationship I ever have with a guy ends in tears, and it never starts out all that well either. But then well, I come back to you, and I think ‘well, okay, i’m a little bit bi, at least for a night’” She blushes, but winks at me. With that the seed planted itself in my head. I felt a twitch in my trousers.
Lindsey came back, looking rather toasty. “Cass, your hot cocktail server makes a strong drink or three. I’m plastered!” She looked at the two of us sharing our lounge chair, “I see you two are feeling cozy.”
“Hey sweetie! Yeah, we’ve been catching up. You want to turn in?”
“Yeah, if you don’t mind. I think the last drink might’ve been too much for me. It’s either the tables or a bed for me. Flat surfaces, you know. But the tables are too expensive. Cass, I’m sorry, I’d love to chat more… maybe tomorrow?”
Cass giggled at Lindsey’s state of inebriation and takes her hand, “Sure. I’ll just walk you guys back to your room.”
We elbowed our way through the crowd at the Paris, avoiding guys in disheveled business casual and tipsy women in tight black dresses. All the while, Cass and I continued our banter. When we got up to the room, Lindsey turned to Cass and said, “Hey. I’m crashing hard, but if y’all want to talk, I don’t think you could keep me up if you tried. Why don’t you come on in? I know Stephen, and he always talks about how you two never get a chance to really catch up. Heck, stay the night if you want to. These rooms are gigantic! We have a California King. We don’t even have to snuggle up close unless you want to.” Cass looked at me for guidance. I shrugged and nodded for her to join us. Lindsey, true to form, stripped to her underwear, snuggled under the bedcovers and went to sleep in about the time it took to pour Cass and I another drink.
We stayed up for another hour and a half cuddled up in one of the big chairs of the room. Cass held my hand and I put my arm around her, and we talk and then we cuddle. Eventually she kissed me on the cheek and said, “The buzz is starting to wear off, I’m dead sleepy, and my hotel’s a mile walk down the strip.” I can’t say I made any real effort to untangle myself. She looked at me for a long second, searching, “Do you really think she’ll mind if I hop in bed with you guys?”
“Nah, it’ll be fine.” And so it was. I found some pajamas and hopped into bed, spooning up next to Lindsey. Cass slipped in behind me, still wearing her dress.
I fell asleep quickly, but you know how when you fall asleep after a ton of alcohol. Eventually you wake up, and you’re just… awake. I lay there, thinking of Lindsey, whom I held tightly, and Cass whose arm was around me. My mind drifted to that night and that painfully sexy shower with Cass. My cock started getting hard, and I mentally prepared myself for a long night if sexual frustration.
And then I felt her hand move. At first, I thought she was changing position, but then I felt her fingers run down my side. I shivered at her touch. I felt her breath, then warmth as she kissed the back of my neck. My skin tingled all over. Embarrassed but suddenly aroused and awake, I waited for the next kiss. It came with teeth, just on the back of my neck. I started to try to pick myself up and turn over, but she stopped me, whispering in my ear “Don’t move. You’ll wake her up. I’ve been laying here for half an hour thinking about the things I would do to you if only we were alone.”
I felt her hands all over my body as she slipped them underneath my pajamas. First, I got harder than I could remember ever being. Then I got wet as precum welled up at the tip of my cock and felt cold against my pajama bottoms. All this and Lindsey is still fast asleep under the spell of Captain Morgan. I just knew she would wake up and Cass would stop. I needed her to keep going.
I held absolutely still, waiting for Cass’s hands to find their way to my cock. Her fingers wrapped around my shaft. Then she pumped more precum to the tip, and I let out the faintest of sighs. She took her hand away, and her arm slid down behind me into her panties. I heard little wet sounds while she fingered herself. When she pulled her hand out of her pants, she held her fingers to my lips. Her whisper was heavy, “I *need* your body.” I lick the wetness off her fingertips, and she slides her hands back down.
At first, I thought she would put them into her panties again and finger herself, but instead they slid into the back of my shorts. She traces her wet fingers down the groove of my ass, and I held my breath until her finger, wet with her own juices slid smoothly inside of me. I choked back a moan. She started fucking me with one finger and then bit down on my neck, sucking hard enough leave a mark. I started to say something, but she stayed me, “Tonight you’re mine. I want you. If you want me to keep going, then turn your neck to me and let me mark you.” She sucked and bit, and the feeling was so intense I fought the need to cry out, almost like she was somehow giving my neck oral sex.
Finally I’d had all I could take. I rolled over carefully and kissed her. We both went silent, listening for any sign we had woke Lindsey, but there was nothing. Cass pulled the top of her dress down and buried my face in her breast. I bit her nipple hard, like she taught me to and felt her struggle against making the same noises I needed to.
She pulled the front of my pajamas pants down to expose my cock and squeezed her fingers around it until I could feel my pulse. She pulled her panties to the side, and put one leg between mine, half straddling me so that I could grind against her from behind. “We can’t, not bare, and not with Lindsey in the bed!” I insisted in a low whisper. She ran one finger down along the bottom of my shaft, wrapped her fingers around my balls, and gave a gentle squeeze.
“If we move from where we are, she’ll wake up. Can you reach a condom?”
“No,”
“I got test results the week before the conference, because it’s fucking Vegas.” She held my cock, ready to go. I didn’t want to, but I determined I would be good. I managed to whimper, “I can’t,”
“It’s okay,” She started to make a move to untangle us, but I put my hands on her and said, “*Please* don’t stop just yet… Just a little more,”
To my relief, she settled back down. I thought she would stroke, me, but then my head met with her clit. She held it there and whispered, “Just be slow and quiet,” My heart pounded in my ears. My mouth went dry. I pushed ever so slowly, and she slid my shaft between her lips, up and down, coating me until I was as dripping wet as her. After a minute, she started slipping the tip further and further back with each thrust. Finally she let it so far back I felt her open up and she pushed the tip against her opening. I wanted inside of her so badly, but she wouldn’t let me in. She kept holding back, because I said I couldn’t – never mind that this was already too far. I cursed myself. She let me back out and slid me along like we had been, fucking me with the outside of her pussy. I pulled each thrust a little further back, hoping the next time she would push again and slip me inside so I could quit telling myself that I would stop after the next thrust. She flexed her hips, grinding this way and that, teasing me with her vagina.
I was sweating with exertion and unresolved tension, thrusting as hard as I could, but always a half inch shy of the thrilling “pop” of entering her. Just as I built up the strength to stop myself she ground her pussy too far and I feel the first inch slip in. She gasped and I thought for a minute she would stop everything. She very carefully pulled my cock out of her and took her leg out from between mine. She turned, I thought away, and I started to protest, but she stopped on her side and pulled her legs up to present herself to me.
Now the decision really was all mine. “Fuck it, I’m going to have to tell Lindsey about this anyway and take my punishment, I thought.” I moved up to spoon her. She pushed her butt up against my stomach and spread her legs slightly. She took my cock in her hand and slid it between her lips down to the entrance. She wouldn’t push it in herself since I said no, but she would rest it at the entrance and let me do it. I fought one last futile battle for common sense.
I thrilled to feel myself lose. This time I met only the faintest resistance as I penetrated her, sinking inch after inch of my bare cock in while my wife snoozed behind me. Guilt made it even more intense. I hoped she wouldn’t wake. When I was buried in her up to my balls, Cass turned her head toward me and sighed, “God that feels amazing. Let *me* fuck *you*, though. Be absolutely still so she doesn’t wake up.”
She grabbed the corner of the bed in front of her to brace herself, then slid up and down my cock no faster than a sleeping breath. It was some of the most exquisite sex of my life. She drew my orgasm with every tense thrust. I felt her pulse throbbing around my cock. When I finally came, it was in waves. I almost lost control and yelled as they crashed down on me, but I bit down on her shoulder and seized her breast in my hand with an iron grip. My fingernails would leave bright red welts in the morning, but I held still while she fucked the last drop of come out of my body.
Then she rolled back over with care. First she buried my face in her breast again and I tormented her while she fingered herself. When I could sense her on the edge, I bit down hard the way she likes. She shook when she came and grabbed the back of my head. I wish I could have seen her face when she came, but she held me in a vise-grip as she pleasured herself. Her orgasm dwindled. Then she sighed, kissed me and held me until my cock dried off and I turned back over to spoon my still sleeping Lindsey. I fall asleep almost immediately, with Cass’s hand on my chest and her heat at my back.
When I woke up, my wife was facing me, looking into my eyes with a far off look. She said in low tones, “I wasn’t asleep.”
It took me a second to understand what she meant. “What?”
“I said I wasn’t asleep. I woke up and laid there with my eyes closed listening and feeling you two making out. Having unprotected sex. Next to me.”
“Oh my god. I’m so sorry,” My heart sank to my knees, but my cock became a steel beam.
She grabbed it, and stroked it experimentally, feeling me harden in her hands, “Fuck her again.”
“*What*?”
“I said fuck her again. I want to watch you. I wanted to watch you last night, but I was afraid if I moved at all, that would be the end.”
Cass woke up presently, saying “Hey, good morning. Thanks for letting me stay the night,”
My brain races to try to think what to say, but Lindsey gets the first word in, “Thank *you* for the show last night.”
Her hands go to her face in terror, “Wha – Ohhh my god! I’m so -”
“Hm. I’ve been laying here for half an hour wishing you two would wake up so I could demand an encore. I want to watch him fuck you. Or you fuck him.”
Her hands fell away from her mouth and she tried to regain her composure, but I could see tears welling up in her eyes. She stared for a moment at Lindsey, clearly wondering if she was being taunted. “That was the hottest thing I’ve ever been through, Cass. All I could do was lay there and listen in the dark. I couldn’t even finger myself because you might hear.
“I was *aching* afterwards, running it over and over in my head trying to imagine what his cock looked like buried in you, what your breast looked like crushed in his hands. I wanted to watch so fucking badly, but you would have stopped. Please… fuck him again. For me.”
Cass stared for a second more, flush with embarrassment, but then a smile grew on her face and she chuckled as she wiped tears away. It was a nervous chuckle, but it had a hint of real relief in it. “Well, ah, O-K. But we’re going to have to fix that first,” as she pointed at my now limp cock.
Before I could protest, my beautiful wife’s long tight curls of brown hair fell down around her face, tickling my cock as she started to go down on me. Cass looked at me still embarrassed, but with a growing hunger. She put her hand down her panties and masturbated while watching my wife suck me back to hardness.
My cock felt hot and ached. I was afraid I’d come with Lindsey still sucking on me, but she pulled away, exposing me to the cool morning air. She looked at Cass, who nodded. Cass straddled me, breasts hanging low near my cheeks so that I instinctively leaned over and teased one of her nipples with my lips. “Now,” Lindsey says. She took my cock in her hands and ran the head of it along Cass’s labia. She slid it into place, then put her hand on Cass’s ass, and pushed down so that the head of my cock slid in.
I groaned and thrust the rest of the way in. I felt Cass’s ass pound my thighs and I hear it crack as she goes from a gentle roll back and forth along my cock to a frenetic fuck. All the restraint was gone. We were loud, passionate. Every thrust a brush with orgasm. I held Cass’s hips and turned my head to Lindsey who sat in the chair Cass and I were cuddling in last night, masturbating furiously as we fucked. Cass rode me out of control. I started chanting her name with every beat until she was covered in sweat and flushed with exertion. I came hard, gushing what must have been every last ounce of semen left in me and fall to the bed, panting. Cass fell down next to me, exhausted.
Lindsey stared at us both with wild eyes, “Wow.” And then after a few seconds she made a face and walked over to Cass’s side of the bed, “So what makes *you* so amazing?”
“What?”
“I want to know for myself why he finds you so *fucking* irresistible,” for a moment I was scared of the anger in her voice, but when I looked at her eyes all I saw was primal lust. She crept up the bed, hovering over Cass malevolently.
“I.. uh… ohhhh!” Lindsey pulled her nightgown up over her head and threw it at me. It smelled like sex. Her breasts hung below her as she crouched over Cass, and I could think of nothing more but how much I wanted to hold them in my hands.
She planted a kiss on Cass’s cheek, then gently on her neck in the same place Cass left a mark on me, then glared into her eyes and spoke in a tone I’ve never heard from her before: measured, but desperate, “I want a taste of whatever’s so amazing about your cunt that he’ll fuck you while I sleep next to him.” That anger again, in the words, but not in her eyes. “You can give me that, can’t you?” Cass looked genuinely worried. She bit her lower lip nervously, but nodded without dropping her gaze.
Lindsey bit Cass’s breast, three quick nips that left pink marks behind, She bore down on her nipple so hard I thought Cass would scream out in pain, but she just sighed and arched her back off the bed into my wife’s embrace. Her cheeks went red and she spread her thighs wide as Lindsey methodically tested every inch of her body from ribcage to hip-bone for reaction. She dug into one spot at her hipbone that drew an unrecognizable noise out of Cass and launched her inches off the bed.
Then Lindsey wrapped her arms around Cass’s thighs. The sound she made when Lindsey penetrated her with her tongue was exquisite. I touched myself, hoping to be able to join the fray, but I was spent. For a minute, all I could do was watch them writhe. Cass humped Lindsey’s face with abandon, grabbing her by the hair so hard, I was half afraid she’d come away with hunks of it.
Cass gave a primal growl like she was about to come, but Lindsey backed away slightly and said “You taste absolutely amazing. I wonder, does he like your ass as much as he does your pussy? Did he ever fuck you there and not tell me?”
“No!”
“I’ll bet he did, your ass is perfect,”
“No! Don’t! Please don’t stop going down on my pussy, please!” but Lindsey hoisted her thighs in the air and traced Cass’s cheeks with her tongue. Cass moans. “If you really don’t want me to, I won’t, but I won’t finish you either. Just say.” She waited a moment, but Cass said nothing. Instead she flexed her thighs and buried my wife’s face in her ass. I could tell when Lindsey’s tongue connects, because Cass clenched her whole body again, then spread wide and grabbed the sheets, “Lindsey! Fuck! Don’t…. stop!”
The shout woke me from my stupor. Lindsey’s ass was in the air. I could see her pussy glisten in the light that filtered in through the curtains. I was still helpless in the cock department, but I came up beside her on the bed. I licked my fingers, then slid them between her lips to find her clit while she rimmed Cass to within seconds of coming. Lindsey was dripping onto the bed. She leaned into my hand, made an appreciative moan, and brought her face up again to Cass’s pussy to go down on her in earnest.
Cass laid spread eagle in beautiful agony. Her cheeks were red. Her chest flushed. She twisted nipples hard as iron between her fingers trying to squeeze every ounce of pleasure from of her body. “Please… Lindseyyyy! AHHHHHhhhhhhh!” She shuddered, and Lindsey surfed the waves of Cass’s orgasm as she bucked and moaned against her on the bed. She finally pushed Lindsey away, shaking as she caught her breath, giggling “FUCK, You are god’s gift to pussy, Lindsey!”
Lindsey thrust once more against my hand, and said “God. I don’t want you to stop, but I’m not done with her,” She sat up and I slid my fingers out of Lindsey who was grinning madly. She kissed Cass fiercely, then grabbed Cass’s hand and thrust it between her legs saying, “Fuck me, Cass…” That time I didn’t get in the way. I watched as they kissed and Cass finger fucked my wife. Lindsey’s face clenches in concentration, “Fuck me hard, I want to feel your fingers pound me! I want you to make me come like you did my husband,” Cass leaned into it, then kissed Lindsey’s neck. “God you *are* good,” Lindsey says. Cass begins biting her and sucking her to leave a mark, instinctively but she catches herself and stops.
But Lindsey grabbed her by the hair and held Cass’s lips hard against her neck. She says between clenched teeth, “Cass, I’m coming! Don’t stop! Bite down hard. Mark me like you did Stephen and make me come!” Cass blushed, but she bit down like she was told, and my wife cries out, wave after wave of orgasm flooding through her all at once. She slumped, kissed Cass, and they both flopped down on the bed. Lindsey motioned for me to join them, and I cuddled up beside her and held them both while they nuzzled and kissed and wound down from.
Cass finally wrapped us both in her arms, saying, “Oh my god, wow! Thank you. Thank you both! Oh my god will I remember this!”
Source: reddit.com/r/sexystories/comments/9tqdic/cass_mf_ffm