Note: this is a follow up story to the Mix and Match series. If you’d like more background about the characters mentioned here, go check out those stories first then come bac. We’ll wait
We were both lying on the bed, naked, coming down off the high of fresh sex. Outside, there was a party, but in this bedroom, it was just us. Olivia and me, and at least for a moment, we could act like she wasn’t engaged to be married, and her fiance, Justin, was one of my friends. It was just quiet smiling and content sighing as I ran my hand through her rich, red hair.
“I’m glad we got to do this,” Olivia had said finally. “Before, you know …”
She looked up at me as I perked my eyebrow at her. “You mean,” I asked, “Justin’s giving up messing around after the wedding?”
“Well, probably not completely, but it’s going to be different. We talked about it and I think we’re both arranging one last night for ourselves. Not the bachelor and bachelorette party. Another night for each of us,” and at this she looked at me in the eye, “… to be with whoever we want.”
She had said that to me in the midst of a crazy party where, for one precious night, aided by the presence of Ecstasy and Viagra, it seemed that we all had suspended our boundaries and inhibitions. It was Malcolm’s birthday and there were drugs and a gathering of friends who were all attractive and had the spent the last few years pairing and re-pairing off in an incestuous series of dating within our own social circle. Malcolm’s fiance, Teresa, was my ex-girlfriend, and while Teresa and I had both long since moved on from that relationship, there was still an energy between us leftover from our time together, coming to fore when I ran into her at that party, naked and high and we wound up fucking on a dinner table. One of the hosts, Justin, was an infamous, shameless flirt, and his own fiance, Olivia, had long tolerated his ways because she knew that he always came back to her. Yet, in that one magical evening Olivia and I had also hooked up, and while naked in the glow of our drug-addled coitus, she had looked at me and said that she was planning one night, to be with whoever she wanted.
I had harbored a crush on Olivia for the longest time. She had always possessed a certain graceful elegance, and a quick but silent intelligence behind her bright green eyes. We both got along in that way that two introverts can hang out in the corner of a crowded party, comfortable in the quiet presence of each other. But, the timing was never convenient for either of us. In the brief period when she was single, I was with Teresa, and by the time we broke up, she had found Justin. Still, there was always the way that we made eye contact when we saw each other, and the way our gaze lingered in that contact.
So, when the Ecstasy took hold, and our bodies charged into an unreal sense of arousal and sensuality, it wasn’t a surprise that we had both sought each other out first. But, then there was a lot coupling going on in that night. We had all managed to fuck or be fucked by every one we liked at that party. When the sun rose the next day, we put on our clothes and, in that gesture, reinstalled the boundaries and inhibitions that we had let slip for that evening. Back to normal. Back to Olivia being engaged and me being her and Justin’s friend.
Yet, that suggestion, whispered in the dim light of their bedroom still haunted my memory. The next few times that I saw them, it was like as if nothing had happened, but there was always a certain subtext in our body language that was different. Then two months later, two weeks away from their actual wedding date, I got an email from Olivia.
“Hi, are you doing anything this Friday? Justin’s heading out of town and I was thinking of dinner.”
It seemed so innocuous, but then that’s Olivia.
I sent an internet chat to Jessica. Jess was one of my oldest friends and had gone to school with me and Teresa. She and I had also hooked up at that party, and that had turned into … something. We were taking things slowly, cautious in that we were friends and not wanting to screw that up. But also, perhaps, we had seen each other at that party cavorting with a bunch of other people, and while we both eventually went home with each other, there was this acknowledgement that we both had unresolved attractions that we wanted to take care of. We had made plans to see a movie on Friday, but things had been vague.
C: “Hey, J, I think the other shoe dropped.”
J: “With ‘liv?”
C; “yeah. she wants to get ‘dinner’ this Friday.”
J: “:))))). Go for it and tell me about it afterwards. I can find other ways to stay busy.”
I sometimes wonder how I lucked into this. I wrote back to Olivia.
“Dinner sounds good, and this Friday opened up. Want to try that fancy, new Vietnamese place that everyone’s been talking about?”
“Sure thing. 6pm?”
“It’s a date.”
“Oh, yes, it is.”
The rest of the week passed in a bit of a haze, and I tried not to let my mind be preoccupied with the possibilities. Jessica had kept up our routine of sending each other innocuous little messages every other day — funny cat pictures or photoshop images that we found on the net — but she didn’t bring up the date, until the day itself.
J: “So, are you looking forward to your big night?”
C: “Haven’t thought of it. I got a few things at work to take care of first.”
J: “Really? Somehow I don’t think your mind’s on work. I think you’re writing up a bucket list of all sorts of vile and unspeakable acts that you’re going to perpetrate on your little lifelong crush.”
C: “Has anyone told you that you’re a dirty little girl? I mean besides me?”
J: “Oh, I can probably give you a few familiar names ;p but don’t change the subject. Seriously, you’ve already slept together once. Do you think this is just going to be a one time thing?”
C: “She seemed to say it is. And, besides, that party was different and crazy, and sometimes I don’t know if we really believed that it happened.”
J: “Well, I think you believe that you and I ‘happened’.”
C: “Oh, so this is what this is really about then? Jealous?”
J: “No, just teasing, and also pointing out that a one time hookup only stays true if it actually only happens just one time. As you and I are probably finding out, it’s a slippery little slope.”
C: “This is the kinkiest friendly advice that I think I’ve ever gotten.”
J: “Hey, remember, we’re friends -with- benefits. Not fucking with bonus friendship. I just don’t want either of you guys to get hurt, y’know? And I know you. I know how your crushes go, and I know that you probably don’t have the highest opinion of Justin.”
She was right about that. In my opinion, Olivia could do a lot better. I could see why she was attracted to him and his party boy glamour, but I also knew that she did not love his flirty ways, only tolerated it as part of accepting the whole package of who he was. While I used to imagine that she would eventually get fed up and leave, I stopped that after finding out that they were engaged. So I just resigned myself to accepting her decision even if I didn’t really agree with it. So I wrote back.
C: “Yeah, you are right, but as I said, it’s just a one time thing to scratch an itch. I think we’ll both be fine, and when I’m done, I’ll let you know what hasn’t gotten scratched off the bucket list and maybe you and I can see if we could work on that?”
J: “Ooh, sloppy seconds -and- being left with the rejects off your perversion list. You really know how to talk the panties off a girl, mister. ;p Just count yourself lucky that I like you and I like that you put out.”
The rest of the day passed in a haze, and I drove home and spent a little too much time trying to decide what I should wear. Could I really be this casual about an encounter if I had already changed through four different outfits? Eventually I settled on a nice button down shirt and slacks. Boring but not too casual or formal. Safe. Maybe that’s what Olivia always saw in me.
I arrived at the restaurant first, and was sipping an iced coffee when she arrived. Olivia appeared in a cap sleeved dress that hugged her slim figure and showed off a bit of cleavage. The cleavage caught my eye since Olivia normally isn’t that busty. A Pilates and yoga devotee, Olivia’ body type was more lean and toned, with firm, perky breasts and a narrow, supple waist that flared out into a nice pair of hourglass hips. Her long hair was pulled back and bundled up into a small knot secured with a pair of chopsticks and her eyes sparkled as she saw me. God, she was gorgeous.
I rose to greet her and pull out her chair, a gesture that caused her to perk her eyebrow and nod as she leaned in close and pecked me on the cheek, whispering, “there’s a clerk that I know from the local courthouse seated in the corner. For now, we’re just friends.”
Olivia was a public defender and built a career for herself arguing the cases for society’s rejects. She always knew that one of her assets was good relationships with people and having a fine attention to detail. So, I just smiled and whispered back.
“Agreed. Friends for now … and for later?”
“Well, we’ll see.”
At this she winked, and let herself be seated before smiling and saying, “That was gentlemanly of you.”
“Well, it seems important to make a good first impression.”
“Oh, I think we’re a little past that.”
There was that sparkle in her eye again, and a barely suppressed giggle that she quickly hid as she studiously perused her menu. After we ordered and settled back in to each other’s company, we kept the talk small and light. How work was going, what we saw recently on TV, Olivia and Justin’s wedding plans. It was, for all others listening, nothing more than two friends catching up. We had split the duck mint salad, and as Olivia lifted a forkful of shredded meat off the plate, she looked at me and asked, “so, how are you and Jessica doing?”
“oh, we’re taking it slow. Trying to be non-commital and keep our expectations measured. Friends with benefits really.”
“And, how is it that benefit package? I assume that it comes with an exquisite dental plan.”
I almost spat out my water as Olivia started laughing at herself. Then mopping my face with a napkin, I recovered and leaned in close and said, “You could say that. Oral hygeine is an important part of the package.”
“oh, is it? And I assume that your level of benefits aren’t contingent on some sort of fulltime exclusivity agreement?”
“Yes, I think you can say that we have a very healthy freelance arrangement. We can call each other for services that need to be rendered, but it isn’t a full time thing.”
“Ah, that’s good to know.”
“Why? Do you think you might need to call upon my … services?”
At this, Olivia drained her wine glass, made eye contact with our waiter and made it quite clear that she needed another, then she looked at me and said, “I might. I think you recall what I talked about during that party? About Justin and I agreeing to have one night for ourselves?”
“I think I might recall.”
“You better have. Anyway, Justin’s gone out of town for one last fling with an old classmate of his. They’d been emailing for the last couple of months and he told me that she always was … what was his word? Oh, yes, unfinished business. So I told him to go off and enjoy himself. Then I’d get in touch with you.”
“So, Justin’s ok with this?”
“Yes, do you want to call and ask him yourself?”
“No, I think we’re all past the need for that. So, what do you have in mind?”
“Well, I booked a room at the Hyatt. Justin and I agreed that whoever we decided to be with, we shouldn’t bring them back to our place; and I didn’t want to expect that you’d open up yours. And, honestly, I wouldn’t mind a bit of pampering and some bed linens with obscenely high thread counts.”
“So, a hotel room, eh? Now that sounds like a proper affair.”
At this, Olivia actually blushed, the pinkness showing up vividly across her pale skin, and her hands went to her napkin, worrying the fabric between her fingers. “Well, it’s not like that…”
I reached over and placed my hands on her fingers, and I could feel her tense up then relax as she accepted my touch. “I’m sorry,” I said, “I didn’t mean it that way. I know that what you guys have is … different. And I’m ok with that. I just meant it as a joke.”
She looked at me again, and then opened up her hand and took my fingers into hers. “You know that it’s only for this one night, right? I know that we’ve always had a connection, and the timing’s always been inconvenient. I love Justin, and I want to build a life with him, but that life leaves behind a lot of other opportunities and experiences, and we want to be able to go forward without any regrets.”
“I know,” I said as I looked back at her eyes, “and I’m sure that you’ll have a happy life. Still, I’m glad that you want to do this with me. And I’ll be happy to just be your friend afterwards.”
“Thank you.” She squeezed my hand then, and released it as our main courses arrived. We took a few minutes to eat and ask each other about our meals, then I asked, “So … obscenely high thread counts, eh?”
“Oh, you know, something that feels really good against bare skin. Fun to roll around and cavort in.”
“When spoiling myself in hotel rooms, I’ve always been a fan of bath products.”
“Really? ” Her eyebrows perked up with bemusement. “I’ve never thought of you as a guy who liked pampering in a bubble bath.”
“I never said anything about pampering. It’s more about who I’m taking a bath with than anything.”
She smiled again, and her eyebrows perked up. “Ah, well, my mistake, I guess I’m going to find out more.”
I took a chance and let my foot slide out until it touched her calf. I could see her eyes widen, then after a moment, her leg moved away, then came back with the sensation of her bare foot pressing up against my leg. We let our feet play as we continued with our main courses. Our talk had paused, but our toes and legs carried on a conversation of their own.
After a bit of time, with my toes gliding across the back of her knee, I wiped my mouth with my napkin and asked, “so, I take it clean up from your party was pretty easy?”
“Yeah, our friends are pretty courteous about it.”
“And there were no … mmm … unexpected consequences?”
Olivia looked at me briefly for a moment before blushing again and saying, “not that I’ve heard. Kind of amazing if you think about it. Given everyone involved and not a lot of protection … it was kind of risky what we did.”
“Do you want to be more careful this time around?”
“Well, I’ve already taken precautions. Justin and I aren’t planning on having kids soon, so I went ahead and got a Nuvaring implanted on the condition that he rein in some of his impulses after the wedding.”
“Ah, so that’s the arrangement, then?”
“Yeah, convenient and fun for both of us, so long as he behaves.”
“And, so, for us?”
She slipped her hand in mine again and smiled, “well, you’ve got a clean bill of health, right?”
“Last I checked.”
“So, I think we can enjoy each other …”
her fingers stroked the inside of my palm
“… as much …”
… gliding, teasing …
“… as we want.”
Olivia smiled as what must have been an utterly glazed look in my eye. God, she was good. She looked me in the eye as she leaned closed and asked, “Were you interested in dessert?”
“I am, though, specifically, I was interested in having dessert at the hotel.”
“Ah, I think that’s a good idea. I might order the same. Did you drive here?”
“Yes. I left it parked on the street, just a couple of blocks away and around a corner.”
“Care to give me a ride?”
“Oh, I’d be happy to give you a ride. And not just in my car.”
“That’s what I was hoping for.”
We paid our bill and headed out. As we walked, I leaned into Olivia and slipped my arm into hers. She looked at the arm, then up at me, and smiled, before leaning into me slightly as we walked the rest of the way. Then, as we turned the corner near where my car was parked, I felt Olivia tug on my arm. She leaned up against the wall, looking at me, and I looked back at her as she tugged me again. I kept looking at her as I leaned in and watched her eyes close as our lips met.
She tasted of sweet Thai tea and cinammon. Her tongue was furtive and playful, slipping up against me and then back, like she was testing things, exploring. Then we parted and took deep breaths and looked at each other again. Then I smiled and whispered
“Ok, then, I was wondering when we’d get around to that.”
“Get me to your car and I’m sure we can get around to more.”
The drive could have gone at warp speed and it would still have been too slow. We spoke little on the drive, as our minds were obviously preoccupied with anticipation. Then, I almost flung my keys at the valet as I pulled up to the hotel and Olivia giggled as she watched my obvious giddiness. A key card materialized in her hand and she said, “checked in already, we’re up on the fourteenth floor.”
The elevator had dinged open, and we got in along with an elderly vacationer couple. Standing at the back of the elevator, we listened as the vacationers bickered about their agenda for the following day. As the door dinged to signal their floor, the vacationers left and Olivia and I looked at each other and smirked.
“Oh, marital bliss. I’m sure you just can’t wait to have that kind of conversation with Justin.”
“Oh, I know what I can’t wait for, right now.”
Then I pushed her up against the corner of the elevator, my lips seeking out the hollow of her neck, as I felt her hip rising up to press against my thigh. Her breath got heavy and husky as I nibbled at the sensitive flesh below her jaw, and there was a slight whimper of lust as my hands moved down to caress her ass.
Then the elevator dinged again, and I looked at the open hallway and raggedly whispered, “which way?”
“Room 1416. To the left. Come on.”
She took my hand and led me down the hallway, giggling. Eventhough we didn’t have that much to drink, we were giddy as schoolchildren. Once we got to her door, and as Olivia fished for her key, I hugged her from behind, wrapping my arms around her waist, relishing again in her cooing as she felt me pressing against the cleft of her ass. I whispered into her ear, “get us in their right now, so I can start with fucking you.”
She moaned at this, and slammed the key card into the door, letting the light turn green and we nearly collapsed into hallway. I kicked the door shut behind us and let her turn around to face me again. Her fingers were on my shirt, unbuttoning me while my hands were in her hair, bring her face up to mine. Shoes were kicked off. I lost my belt at some point, and then we were both on the bed, my shirt out of my pants and my hands up her legs. Olivia had worn a pair of stockings, and I could hear her gasp as my fingers finally found the bare flesh above the lace. Her thighs parted and I could smell the ripe, heady essence of her arousal, as I leaned in to devour her with another kiss.
My right hand, still on her thigh, pressed flat against the skin, so my thumb could rub against the fringe of her silken panties. She moaned again as she pushed up against me. Soon, Olivia had me lieing on my back and she stood up and straddled me. Her hair was a mess, her eyes with half lidded and her lips were curled up in smile that was half giddy and half predatory. Then, she reached behind herself and pulled down a zipper on the back of her dress. I planted my hands on her hips and started to push the dress up as she grabbed the fabric around her waist and began to pull. Soon, she had the dress up and over her head then flung to the side of the room, and there was Olivia clad in a black silk underwear and a garter belt with stockings, her wild red hair falling in a heap around her, and a flush of pink on her cheeks and collar.
“You,” she said, “are wearing too many clothes.”
I sat up as I let her peel my unbuttoned shirt off my torso, and I kissed the tops of her breasts above her bra, while I let my hands run along her back, letting my finger nails drag across her spine. Once my shirt was gone, I could feel her push me to lie back down, and then she got up off me to pull my socks off. I obliged with undoing my belt and unbuttoning my pants, before she reached up and began peeling those off too. My stiff cock was still lurking beneath my boxers, but as she pulled my pants down, Olivia let her cheek slide across the fabric of my shorts, her hot lips a mere inches from my aching flesh. Then my pants were gone, and as she came crawled up to me, I reached over, and slid my hand behind her back, to grab at the snap of her bra. She smiled as I undid the clasp then looked down almost demurely as she let her cups fall from her chest.
Olivia’ breasts were as perfect as I remembered. Compact and firm, with rosy nipples at their cap. I let my fingers trace around to graze their flesh, as she leaned in for another kiss. Then placed my hand on her shoulder and turned her back over to lie beneath me.
We were kissing deeply again, as I leaned into her, pressing my right leg into the space between her thighs, feeling the softness of her panties yielding against the firmness of my thigh. With one hand still fondling her breasts, another cupped a soft expanse of ass and pressed her against me. There was another moan, and her whispering into my ear, “I can feel you against my leg. I can feel you wanting me.”
“Oh, dear, I’ve been wanting you for very long.”
“Then, I’m yours. For tonight. Everything you want to do. I want you to do it to me.”
“What do you want me to do? What do you want done to you?”
“Oh … you want me to say it?”
“Is it hard for you to say? Do you need to think about it?”
… and at this, I let my hand, which had been cupping her breast, glide lower down to her belly, to swirl around her belly button
” … are you not ready?”
… then, another groan from her as my swirling got wider in its orbits, sweeping inexorably to the tops of her panties.
“Are you not ready for me?”
… then her breathing stopped as my fingers slipped under the elastic at her waist. Then, my own breath caught at the bare flesh of her shaven mound, then the wet heat of her arousal.
“For me to … fuck you?”
And she moaned as I slipped a finger inside of her.
“Ohh, Chris, I want you to. I want you to fuck me so bad.”
But I said nothing. My only response was my finger exploring her, soon joined by a second, then my thumb swirling at her hood, seeking her clit. Our conversation had stopped, subsumed into groans and gasps, as I just let my fingers delve further and further into her, mapping her depths and folds, while my thumb felt her clit emerge from its sanctum. I slid my fingers out and up, letting both of them settle on either side of that treasured nub of flesh, and I could hear Olivia’ breath change pitch, growing more ragged and hoarse as I started pulsing my digits over her most sensitive trigger. She had stopped kissing me then, fighting instead for breath as her body began to tense and tighten. My hand was soaked as it strummed her, and I could soon feel her body pressing against mine as she began to buck and spasm and then bury her face into the crook of my neck as she moaned.
“Oh, fuck. Chris. Fuck. Fuck. Fuck. Fuuuuuuuccccck …”
With that, her body went limp, and her head collapsed against the pillow as she weakly returned a kiss that I smugly placed on her lips. I pulled my hand from her panties, and tugged the drenched fabric down over her thighs , revealing the rest of her bare pussy, engorged and glistening. Her fingers went to the snaps of her garter belt, but I placed my hand on hers and shook my head.
“Leave them on.” I said. Olivia looked at me and smirked again, and then reached back to grab some of the pillows on the hotel bed. She piled them up so that she could lie back on them a bit, gazing at me with a relaxed fondness.
“Come up here,” she said, “I want to see you.”
Obliging her, I straddled up to her reclining form, kneeling with a leg on either side of her as she pulled down my boxers to set my cock free. It was rigidly, painfully hard and nearly popped out into her face as she tugged the fabric down to my thighs. She let her fingers graze along its sides, then dance over the head before she tugged it down, almost using it as a handle to guide me back down and signalling where it should go.
I took my place between her legs, setting my cock on the threshold of her eager, glistening pussy. I held it there for a moment as I locked eyes with her.
“Is this what you want?”
“Oh, yes, I want you.”
I placed my hands on either side of her hips, lifting her pelvis slightly as I slid my head up to her folds, gliding over her wetness in that delicious moment of contact.
“Do you want all of this?”
“Oh, goddammit, yes. Chris. I want you to fuck me”
She sighed as I slid myself in and reveled in the heat of her wanton pussy. With Olivia’ recent orgasm, I slid in easily, burying myself into her with one smooth stroke, and as I put my full length inside her, I held that position and leaned in so my face was close to hers, our eyes locking, my sight savoring her happy smile.
“God,” she said, “it’s been too long.”
Interesting. I didn’t say anything, though maybe I grinned a little and then kissed Olivia deeply, before I started to stroke myself in and out of her. I took her in slow, measured strokes, letting myself keep control and holding my build up at bay. Our last time was drug crazed and wild and intense, but also quick, and I wanted to make this last, to remember everything of her warmth and softness and musk.
I switched my grip so that my left arm was now wrapped across the small of her back, and my right reached up to cup her breast, stroking her nipple, then moved up to cup her face. She turned to kiss it, nuzzling her cheek against my palm, then reached up to hold my hand in her left. She still wore her engagement ring and I could feel the coolness of the metal against my fingers. Then I laced my fingers in with hers and drove into her harder.
With my grip on her back, I could pin her pelvis in place, and plow into her with more force. Her breath had quickened as my thrusts grew in strength then I placed my lips next to her ear and whispered “is this what you’ve been planning? What you’ve been waiting for? This moment of my cock fucking your hot little pussy.”
“Oh yes. Oh God yes.”
Then Olivia wrapped her legs around me, scissoring across my ass as she pulled me deeper into her. Her whimpering had taken on a different tone now, one that I was starting to grow accustomed to, the call of her climax building within her again. I let my rhythm stay constant, just thrusting steadily as I tried to keep up with the way her body bucked and quaked beneath me. She was close and so was I. I tried to keep my breathing slow so that I wouldn’t be first, but then she whispered.
“Ever since that night, every time I’ve seen you, even when I was with Justin, I couldn’t help but thinking of you fucking me.”
Oh, that was so unfair. The lurid image of Olivia all quiet and demure, pretty and polite, but harboring a simmering sluttiness was enough to do me in; and I just groaned as I lost control. Yet, as I did so, and felt with a certain wistful disappointment as the pressure in my cock exploded, I also felt an elated satisfaction as Olivia’s pussy tightened around my own, followed by that same gutteral moan as her face pressed itself into my shoulder. I kept coming for a few seconds longer, letting myself coat her welcoming chamber, and provoking after shocks in her with every small eruption.
We stayed quiet for a few moments after, catching our breath. I was still inside her, somewhere between hard and flaccid, and as I slowly tentatively started to thrust again, she cooed langorously then asked me “You were like this last time, too. Still hard after cumming. How do you do that?”
“I don’t know. It doesn’t happen always. Only certain times with certain women.”
“I guess … unh, wow … I should be flattered.”
“I think you should be. I find you to be pretty hot. And that filthy mouth of yours is a pleasant surprise.”
“You’re the guy who was talking about fucking me in the elevator. I honestly didn’t think … oh yes … fuck .. I didn’t think you had it in you, either.”
“A lot’s changed since we partied.”
“A bit … but also, I don’t know. I think that party unleashed an interesting side to all of us. Like we were all mild mannered professionals by day, and we may suspect that we’re all just a bunch of horndogs, but it’s something else to have it actually happen.”
“Hey, Chris, we can discuss philosophy or we can fuck, but doing both is a little distracting don’t you think?”
“Ok, I’ll shut up. Switch positions?”
She rolled on top of me then, and I buried my head in the mountain of pillows as I watched Olivia rise above me like a Venus emerging from the sea. She swept her red hair back behind her as she started to ride me. I left my hands at her waist, running up and down the sides of her stockings, then roaming up her back and sides, feeling her sigh as I found spots of her that were still sensitive from her last climax. She smiled as she glided her slick pussy over my cock.
“This is nice. I’d be happy just spending the rest of the night doing this.”
“Mmmm.” was all I said. I just closed my eyes and stayed quiet, just enjoying the moment. I don’t know how long we spent doing that. Time was unimportant. We were just enjoying the feeling of each other, the pleasures that we were giving and taking, just simple, straight fucking.
Still, as time wore on, I could feel Olivia’ hips take on a different tempo. Her motions took on more of a corkscrew pattern, and then she leaned forward, so that her torso was draped over me and her stiff delicious nipples dangled just above where my tongue could reach them.
“My knees are getting a little worn out in this position. Ok, if I bring us home?”
“Yeah, baby, do it.”
She kissed me again, then I felt her slam down on me with more force, impaling herself with shorter, more aggressive bursts, leaving no doubt in either of our minds that this time, she was the one fucking me. Then as I heard her breath catch, Olivia reared up, leaned back and planted her hands on my knees. My cock was now pressed against the outer walls of her vagina, and a ridged vein at the base of my cock was placed at the base of her clit. She worked herself to a frenzy in that position, using the ridges of my cock to stimulate her, until she finally started to moan again.
I kept my breathing deep until I felt her pussy begin to tighten, then I sat up and wrapped her torso in my arms, as I took control back and began to pound her from below, sending her quickly into a second chain of orgasms, before I also joined her in climax, shooting more sperm into her now thoroughly soaked vagina.
She kissed me deeply and thoroughly as we both came down off that peak. Her teeth nibbled gingerly on my lip as if she needed to devour me further, then as we recovered our breaths, Olivia pushed me back onto the pillows and then whispered, “hold on, I need to use the bathroom.”
Then there was the sensation of my limp and thoroughly drained cock falling out of her, and the bounce of the bed and the lovely sight of her shapely derriere retreating to the toilet.
I wished that I still smoked. There was the sound of a faucet and quiet, then the door opened and Olivia re-emerged with two glasses of water that she set by the night table, before slipping under the sheets and motioning for me to tuck in under the covers with her. We cuddled up together, and I realized that at some point in the bathroom she had ditched her stockings, so now it was flesh against flesh.
“Ok,” she said as she nestled her head on my chest, “now we can talk.”
“What was that you said, about ‘it being too long.’ ?”
“Oh that? Heat of the moment stuff. The wedding’s been stressful, and stress can put one of us out of the mood. So, Justin and I have been more … how should I say this … business-like lately. Should be ok once everything’s done and we’re on our honeymoon. If anything, this arrangement is a bit of a pressure valve for both of us.”
“Don’t you think it’s scary, though? Committing to someone and having troubles coming up before you’ve even said, ‘I do’ ?”
“I don’t believe in fairy tales and perfect romances. I’m a lawyer, remember? I believe in contracts … or, well, as an allowance for romance, I believe that we’re all human and we have desires and emotions, but we need to have agreements that help us get past the rough stuff when maybe our short term interest says ‘quit’ but our longterm interest reminds us to ‘stay’.”
“That really isn’t answering my question.”
“No, I’m not worried. We’ve been worse than this, and made it through. I wouldn’t have accepted Justin’s proposal if I didn’t feel that we’ve been tested. We’re really different in certain ways, but it’s a difference that works for us. Though sometimes it brings up a bit of friction, it’s part of the package.
“Like, you and I, Chris, we’re really similar — like siblings, you know? And I think that’s good,and I’m happy to be with you; but it’s like we’re too similar and if I were to stay with you, we’d just windup reinforcing all of the good and bad parts of each other.”
“That’s a very nice, preliminary rejection.”
“Oh, hush, I’m with you now, aren’t I?” She poked me in the chest as she pouted adorably. “I’m just saying that we should enjoy this for what it is. A chance to be together and have all of the fun that it entails without any of the resentment or bitterness of having things not work out. We can be each other’s Ones Who Got Away. Spoon me?”
I laughed and nodded at the almost non-sequitur, then settled in comfortably as Olivia turned away and let me wrap my arms around her and pull her back into me. I slipped one arm under her torso, hand coming to rest comfortably on her stomach, another arm lightly cupping her breast.
“Mmm…” she said a little dreamily, “you are good to cuddle with.”
“And, you, my lady are very cuddle-able.”
“Sweet-talker. So, tell me what Jess is like in bed. She seems like she’d be pretty energetic.”
“Hey, a gentleman never kisses and tells. I don’t think you’d appreciate if I told everyone what a wildcat you’d turn into if someone just whispered the right things into your ear.”
“Ok, fair enough. Tell me anyway, but feel free to mix in some or a bunch of made up stuff in there. It’s really just for my imagination. I want to imagine you doing it with someone else.”
“Mmmm, well then.” I started to nibble on her ear to get things going. “You’re right that she’s game for pretty much anything. We haven’t slept together too often, it’s been pretty casual and we’re both busy. But, there was this one time that we were coming back from a party at Quentin and Amy’s place, and she asked me if I had any plans the next day, and when I said that I didn’t she asked me to stay over at her place.”
As I kept whispering in to Olivia’ ear, I could feel a new surge of blood flowing into my cock, inflating it once more as it nestled in the cleft of her ass. I felt her shift position again, letting me slide neatly between the two soft spheres of soft bum. She sighed again and said, “Keep going.”
“I told her that I was flattered but a little tired and unsure, so she took that as a challenge, and when we stopped at a red light, she leaned over, unzipped my fly and slowly started sucking me.”
Olivia started to rub her legs together, and with that her ass had started to move against my semi-flaccid cock, bringing it to life in time with my story.
“I don’t know how long we were at that red light, but it wasn’t long enough, and once it went green, Jess lifted her head from my lap, placed a hand on my thigh and whispered, ‘eyes on the road, but the next time we stop, I’ll keep on distracting you. That hand, softly squeezing my thigh was enough to keep me from going completely soft, but as we got to the next light, I remembered taking my foot off the accelerator and just letting the car coast for a bit. A taxi behind me peeled off and flew past a little aggressively, but then we got to the light just as it turned yellow, and I hit the brake until it went red. Then I looked at Jess and she smirked and looked back.
“‘Safety first.’ Then she resumed blowing me.”
Olivia had chuckled, and by this point my cock was well back to stiff, so I let one hand stroke her nipple, while my other palmed her vagina, feeling her emerging heat and the first trickles of her moistness.
“We kept that up for maybe five? six? signal lights. Each time was long enough for her to get me hard, but not long enough for me to blow my load, and when we finally got back to her place, I thought she’d finish me off in the car, but she just got up and opened the door. I tried my best to start stuffing my totally hard cock back into my pants, but I was lucky enough just to keep my pants up around me as I staggered in after her and just started mauling her in her entranceway.”
“Oh, tiger. So moral of the story is that shouldn’t be teasing you? Not like the way I’ve been jacking off your cock with my ass?”
“I was wondering about that …” and at this I shifted, so that my tip was starting to rest against her asshole.
“Oh, wait hold on.” Olivia leaned to the night stand and opened up a drawer, pulling out a bottle of lube. “Two conditions. You use this and you wash up afterwards. Hygeine, you know.”
I kissed her shoulder, as I spread the lube on my stiffened cock. Then I drew the sheets back, so that I could get a complete and unobstructed view of Olivia’ gorgeous ass. Obligingly, she pulled one cheek open and presented herself to me.
“I’ve only ever done this with Justin.”
“Well then … thank you.”
She took a breath in sharply as I entered her. I’ve only fucked the asses of two other girls, but everytime it’s a bit of a thrill. The passage is so tight, and even with lubricant, the sensations are so overwhelming, for both of us probably. I eased into her, pressing in inch by inch, until I was fully balls deep and beneath me, Olivia was panting with effort.
“God, I feel really full.”
“You feel really good.”
I reached around and slipped my fingers into her pussy, playing with her vulva and clit as I started to stroke in and out of her. The lube made it easy to move, though also amplified the heat of her. Eventhough I had already come a couple of times today, I knew that I wouldn’t last long inside her this way. So, I focused on bringing Olivia off as quickly as possible, zeroing in on her clit and continuing to whisper filth into her ear.
“You like it in the ass? You’ve got a dirty little side to you, don’t you? I imagine you as the calm, stoic, professional lawyer, standing in your courtroom, bored by the testimony and fantasizing about having a cock buried in this hole.”
“Oh, yes, fuck me, I’m a dirty little slut.”
“Are you sure you only want me to fuck you this one time? Don’t you imagine having Justin in your wanton little pussy while I ram you from behind?”
“Oh, fuuuuuck, Chris. You’re bad.”
I slipped a third finger into her pussy, which was now throbbing with desire. “You want to imagine my hand is your fiance? You want us fucking you at the same time? In. and out. In. and out.”
“Shit. Shit. Shit. Shiiiiiiiiiit.”
It was then that I felt her clamp around my plunging hand, dowsing me in her essence, and I took that as my permission to pull out shoot myself all over her tasty hot ass. And once I had run dry, she turned over, sat up and kissed me again.
“oh, Jesus, Chris, That was amazing.”
I collapsed back into bed, letting the entire experience drain out of me, but then I felt Olivia’ nose poke me in the shoulder.
“What? I am not passing out on you.”
“But, you do need to clean yourself up. Remember. Hygeine.”
So, I got up out of bed and walked over to the bathroom. From the mirror, I could see Olivia brazenly checking out my butt. I chuckled and made eye contact with her through the mirror. She laughed back. “What? I’m sure you were doing the same thing.”
Fair point. I ran the shower and dipped my cock in the stream, but then felt like if I was in for a penny, might as well be in for a pound and stepped into the stall to wash myself down and freshen up. I had just started soaping up my chest, when I heard the shower stall open up and Olivia came in.
“You’re taking this hygeine thing fairly seriously.”
“What can I say? I figured that you’d appreciate a nice, clean, spring scented me.”
“That’s sweet. Here let me soap your back.”
“Ok. Hey, that’s not my back.”
“It to your rear, and I’m sure that it’s hard to reach.
“I got something else that will be hard if you reach for it.”
“I’m sure but I think you need a little break. Just stand still, and relax.”
I felt the tips of her thumbs pressing into the hollows beneath my shoulder blades, working their way upwards and outwards to massage my neck and deltoids and biceps. Her breasts brushed against my spine as she leaned into me, working my forearms and triceps before slipping back to my torso and massaging the muscles against my spine. Combined with the hot shower of the water and sensuality of her lips blowing softly on the back of my neck, it all felt heavenly.
I had gotten relaxed to the point of almost passing out in the shower before I could feel Olivia grab my shoulders and turn me around so that I was facing her. I looked into those lovely green eyes again, and where I had seen hunger and lust before, there was now something else. A bit of fondness and maybe peace. I leaned down and kissed her again, a kiss that was gentle and lovely and kind. Then she pulled back again, and the hunger was there once more.
She kissed my neck. Then my shoulder, then she kissed my chest, and pushed me back against the shower stall. Olivia’ lips kissed a trail down my chest, and my stomach and for a weird vain moment, I felt a need to suck my gut in. Then, there were her lips on my cock. Slipping around me, wrapping me in the warm vessel of her mouth, and sucking me to arousal. I leaned back against the tile of the shower letting the warm water wash over us as I hovered between passion and fatigue.
I think she realized too that it took a while for me to come back around, but if it bugged her, she didn’t complain. Instead, I could feel Olivia quicken her tempo as I started to respond, letting her lips pull me out further and further, and her tongue danced along the sensitive underside of my shaft. Finally, as I was back up to my full length, Olivia stood up, and kissed me again, then took my hand and tugged me out of the shower.
I had the presence of mind to shut off the water, and we toweled each other off, then I let her lead me by hand back to bed.
Unlike the last few times, we didn’t say anything to each other as we got back under the covers. I just slipped the sheets over us and let myself nestle between her legs, as I felt her hand on my cock guiding it once more up and inside of her. She wasn’t as torridly wet as she was before, so as I entered her, I could feel a bit of pressure, and a soft sigh from her lips as Olivia let herself expand to accomodate my cock. She placed both hands on my face, and kept her eyes on me, as I thrust in a little deeper, letting our union blossom between us. Eyes still together, smiling, quiet and one. Then we moved together, her hips pulling back slightly in time with mine, then sliding back together. In and out, one mind and one rhythm.
I hadn’t tracked time as we did this. Not saying anything to each other made each moment seem like its own timeless jewel. While the expressions on her face changed, as a new bit of pleasure surged into her, that fond smile stayed constant, as did the way her eyes looked into mine. It was almost meditative to do it like this. The only things I was thinking about was the pleasure and our breath and her eyes.
Then, her eyes fluttered and her breath caught and again, I could feel her body tense and fold up as one hand wrapped around the back of my head, pulling me down to kiss her again, as another hand slid down to my butt, pressing me into her, doing her best to ensure that I wouldn’t stop. And then there was that delicious and familiar whimper, and I could swear to this day that I would never tire of hearing that.
And then her body seized around me like a small series of thunderclaps. I kept going, kept thrusting, and then there was an aftershock and another and a third still. Olivia’ eyes had flown open after that one, looking at me incredulously as I kept driving into her, a fourth climax obviously not far behind. There seemed to be a sense of pleading in her eyes, so I sped up my pace, letting my self slide into and out of her now fluid little pussy. Where she had been silent before, she had started to moan, throwing her head back and letting herself be given completely to the moment. Her hips had stopped moving now, her legs wrapping themselves around me again, pinning me to her and making me hers.
It was her final orgasm that did me in. Feeling her pussy pulsing once more around my rampant cock, followed by the ragged gasping in my ear was enough to send me over the edge, and as I emptied myself into her, I felt like while this one wasn’t as frenzied or prolonged as my previous orgasms, it would be one that I would most remember.
I collapsed beside her and let her drape herself over my chest as we both let sleep and the night claim us.
I awoke some time later, as the early light before dawn started to filter behind the drapes. Olivia had nestled her body into mine, letting me spoon her again. For a few minutes, I simply enjoyed the warmth of her, trying to imprint the memory of her scent so I could hold onto it a bit longer. As I nuzzled her hair, I could Olivia sigh a bit contentedly and her body nestled itself deeper into mine. My cock was hard and alive with morning wood and responded well to the enveloping warmth of her hip as she pressed up against me.
I slipped one arm around her and slowly stroked her belly, enjoying the soft curve of her flesh, then sliding up to cup her breast and plant light kisses along her neck. She sighed again, and I could feel her nipple slowly harden to an erect nub. Her legs shifted, parting slightly to give me a tantalizing view of her bare pussy. I slipped my other arm beneath her to cup her other breast and then let my top arm trail down her flank, under hip and then between her drawn up legs.
I started with one finger tracing the small line of her slit, feathering it lightly until I could feel the barest dew of arousal. Then as her quiescent folds began to blossom, I let that finger press a little deeper, rubbing her petaled lip as they unfolded to greet my touch. Her breathing had taken on a faster tempo too, and as I slipped my middle finger into her now open breach, I could see Olivia’ eyes flutter open and her breath hoarsely whispering, “don’t stop.”
Her legs shifted again, giving me deeper excess to her now fluid cunt. Olivia’ eyes had now locked with mine, and leaned down to kiss her awake. Her mouth tasted of salt, sweat and passion, then I kissed her cheek, her throat and the hollow of her collar. She turned to lie on her back as my lips traced their way around the supple curves of her breast and then the ridges of her ribs. At her stomach, I could feel the delectable tension of her stomach and the lovely nub of her belly button. Olivia made a sharp intake of my breath as my lips reached her waist, then the edge of her groin. And she let it all out in a long sigh as my tongue traced along her labia.
I licked my way around and into her as the sun rose on the windows outside. Her nectar tasted sweet and floral, trickling over my lips and chin, and filling me with a heady sense for her. Olivia’ hands reached down, to caress my hair and I let my fingers intertwine with hers. I kept licking, sucking and tongueing her, teasing and savoring the prominence of her clit and the moist warmth of her vagina. Then there were her hands pressing down on my head again, and her thighs clamping around my shoulders as Olivia came to a shuddering climax.
I kissed my way back up as she caught her breath, and when I planted a deep, soulful kiss on her lips again, she looked at me then satieted said, “Thank you.”
“I think I need breakfast.”
“Food sounds like a good idea. I’ve also got some protein to replenish.”
Olivia leaned over and dialed the phone, adopting an oddly chirpy tone as she simply said, “yes, I’d like some breakfast please. Two people. Continental is fine. Coffee?” She looked at me, perhaps a litle sheepish, and I just nodded. “Yes, coffee. Ok. We’ll see you when you get here.”
She looked back at me as she hung up and said, “I’m sorry.”
“I don’t know. It felt like I should’ve known if you were a coffee or tea sort of guy.”
“Well, I won’t hold it against you. But … ” and I placed a hand on her waist “…. do you think I’m an ass or a tit sort of guy?”
“Oooh, well given what we’ve done together … you haven’t fucked my tits yet, but I’d still say … both?”
I smiled as I used one hand to cup her butt while the other stroked her nipple. “Good girl.”
“Though, you know, my tits aren’t quite big enough to be fuckable.”
“Shush … I like them as they are. They’re you. And they look pretty hot on you.”
“Thank you. You’re pretty hot yourself.”
Olivia turned back and kissed me again, and we made out for a while before hearing the doorbell ring.
“Shit,” she said, “I need to get decent.”
She bounded out of bed and grabbed my shirt, quickly buttoning it around herself as she moved to answer the door. From where I was lying in bed, I could see that the waiter, a nice strapping young man of no more than 20, could figure out what was going on. I wondered what he made of us, of this woman greeting him with nothing more than a shirt and a smil, or of the scent of sex on Olivia’ hand as she signed the slip for the food, and then graciously took the tray from him before making it clear that he should continue on with his duties.
I laughed as soon as the door closed, and Olivia shot me a look of mock astonishment like “what? did I do something wrong?”
“Poor lad isn’t going to concentrate on the rest of his duties after seeing someone like you. He’ll be lucky if his hardon doesn’t get trapped in the next room door he has to deliver to.” I got up and sat next to her on the table where she had placed the breakfast tray, and we poured ourselves coffee and opened jars of jam for spreading on toast.
“Oh, hush, I’m sure he’s a true professional.”
“I think you’d like to know what sort of professional he’d be. He certainly seemed handsome from where I was lying.”
“No contest there. I like to imagine that he probably gets his fair share of ‘midnight snack calls.’”
“You know, if you want to ask him back, I won’t mind. It’s not like I get to be possessive of you anyway.”
“Oh, but you’re more than enough for me, my friend. I’ll be lucky if I can walk straight down the aisle after this weekend.”
“What do you think you would have done if I got cold feet for tonight? Just called someone else?”
“Maybe, I don’t know. To be frank, I didn’t really feel like pulling in anyone else. Malcolm’s really not my type. Quentin’s too passive. Francis is just a little too much of a horndog. I might have just called it off.”
“But it’s one last night of sex with someone who isn’t your husband. You wouldn’t have just gotten a male prostitute for a night of totally professional sex?”
“No, that would be cheating.”
“And this isn’t?”
“This isn’t. Cheating means that one party is breaking or abusing a set of rules to gain an unfair advantage on the other party.”
“Right. I forgot. Lawyer.”
She punched me lightly in the arm. “If the rules permit a little sleeping around and both parties are free to indulge, then that isn’t cheating. It’s just considered cheating if you use the standard cultural ruleset of absolute monogamy. Our rules permit sleeping around so long as we both know the person and we’re both ok with it.”
“So, that strapping young waiter who just delivered our breakfast. If I were Justin and if we were in a hotel room on our honeymoon, and I said that I’d be ok with you fucking our waiter because I could see how hungry you were for him, would you do it?”
“Maybe. If I were in the mood.”
“I’m going to take the breakfast tray and go outside and ring the buzzer. Greet me like you’ve just been given permission to fuck my brains out.”
“Who the hell are you and what did you do with my friend, Chris?”
“Oh, it’s still me. It’s the me who’s got only one chance to see how much of a wanton little hussy you really are.”
Olivia looked at me with a bemused smile as I put my undershirt and pants back on, then I picked up the breakfast tray, put the silver cover back on top and walked back out into the corridor. After a bit of a pause, I held up the tray in my best server posture, and then rang the door table.
I stood out there for what seemed to be a few very long moments. I wondered briefly if Olivia was just taking that as an opportunity to say she’d had enough with me. Then the door opened and there she was, still dressed in my shirt and nothing else.
“I, uh …” I stammered in my best roleplay of a flustered waiter, “ma’am, you … uh … ordered room service?”
“Why, yes, I did. Why don’t you come in?”
As she turned and walked back into the room, I was quite aware of the way that the bottom half of her ass swayed into view beneath the shirt, and how obvious it was that she wasn’t wearing any underwear. I did not need help to pretend my arousal. I followed her into the room and watched as she cleared a space on a small side table, bending over just slightly enough to let the shirt ride one or two scandalous inches up her ass.
“You can just set it down here.”
And she did not step away as I set the tray down on the table, and instead seemed to close up the distance with me, as I set about placing the two plates and coffee mugs.
“Um … uh … I was told that this would be breakfast for two?”
“Oh, yes, my husband will be back … eventually. He left this morning to go take a snorkeling lesson, and he left me quite … high … and dry.”
Olivia’ breath had taken a bit of a husky tone as she sidled up next to me so that my right hand was now touching the bare flesh on her hip, just below my shirt.
“Well, then, can I do anything else for you, ma’am?”
She looked me right in the eye and said “I have a couple of ideas.”
Then she started to unbutton the shirt. I let my hand slide across her thigh, and then up the inner skin of her leg, and I felt her legs spreading open in anticipation. Her cunt was hot and ready, and nearly gushing as I pressed myself in. The tops of her tits were now visible through the gap in the shirt and I reached in with my other hand to cup one breast while my other fingers explored her fresh, hot pussy. Then I realized that the earlier delay was because she had been washing herself for me.
As my fingers played with her, Olivia’ voice had decended into wordless, ragged gasping but her hand had gone to my pants to palm my cock through the fabric. I Ieaned in to kiss her, but she turned her face away and simply said, “not on the lips. Anywhere else but there.”
I placed my mouth on the space between her neck and jaw, and let my tongue slide across that smooth, fragrant skin. Then I dropped my head down to kiss her breasts, and suck at her nipple. Her hand pressed my head closer as I grabbed her ass and heaved her onto the bureau, letting her sit back and open her legs even wider.
Her clit was extended like a small flag at this point, and my thumb and index finger were twiddling it like a dial. The entire roleplay was enough to prime her up, and my fingers didn’t take long to bring her over the edge. Within a few minutes, Olivia had tipped over, and I felt her body quake against mine as my fingers stroked her over, and over, and over. After a prolonged assault of this, I felt her hand clamp down, to make me stop and give her some relief.
“That,” she said, “was what I call service. You deserve a tip.”
She leaned over to grab her purse and pull out her pocketbook. She took out a twenty and laid it down on the bureau, then rolled herself on top of it, so that I could now look and see that Olivia was lying on the bureau, her legs hanging off and planted on the carpet, and her ass raised a bit with the twenty just below her groin.
“Well? What are you waiting for?”
Smiling, I unzipped my pants to unleash my cock, then holding it in one hand, I let myself trail my head across the lips of her swollen, insatiable pussy. I felt Olivia push back, to meet my cock, but I pulled back as well to tease her. We kept at this for a couple of cycles before I could hear a certain plaintive moan from Olivia’s lips, which I took as my signal to lean forward, grab her hips in my hands and ram my cock right into her hungry little cunt.
If her moans were plaintive and desirous before, now they became pleasured and lusty.I looked down and watched her curvy ass slapped back against my hips. I revelled in the sight of cock sliding in and out, glistening with our juices. I leaned forward again and whispered, “ma’am, I thank you for the tip, but in the name of guest safety, I should remind you that I’m not wearin–”
“I don’t care. Don’t worry. I’m ok. Just fuck me, you stud. I want you to leave a little something for my husband.”
“Oh, yes, indeed ma’am.”
I picked up her left leg and placed it on the bureau, opening her up even wider as I grabbed handfuls of her hip flesh and pounded into her with renewed vigor. At this pace even with all of my previous orgasms, it wouldn’t take long for me to come, so I just jackhammered my way into her pussy. Olivia, still freshly sensitive from the hand job that I had given her, shuddered under my frenzied pounding, and soon she was working herself into a new climax, talking lewdly all the while.
“Oh, yes, my stud. Fuck me with that naked cock of yours. I want to feel all of you inside of me. Keep it up. GIve it to me. Give it all to me. Fill me up. Fuck me. Fuck me. Fuuuuuck meeee.”
And so with ragged breath and sweaty brows, I slammed into her one last time, burying myself deeply as I unleashed what was left in my balls. Once my own explosion subsided and I caught my breath, I just pulled the cum soaked twenty from beneath her torrid snatch. Catching her breath, Olivia pushed her sweaty hair from her head and got up, turning to face me with my unbuttoned shirt still draped across her torso.
“so … breakfast.”
We ate in near silence, just talking to ask for the jam or some salt. I think we both realized that our time was coming to an end, and while neither of us wanted to talk about it, ignoring it didn’t make it go away. Still, the clock ticked on and with that, our time together was running out. We looked at each other as we chewed our pastries and sipped our coffee. Then, almost at once we both set our cups down just looked at each other.