Over the past year, Theresa and I had become quite comfortable with injecting some occasional fantasy play into our lovemaking. We hadn't involved Courtney and Steve, the couple we had become intimate and comfortable with sexually since the night months ago at their house when we were treated a bravura exhibitionist performance by Courtney. Ree and I kept ourselves satisfied and happy with frequent sex and a judicious smattering of role-playing scenes between the two of us.
We had just finished a very satisfying "vanilla" session of lovemaking when Theresa lay back on the pillows and said, "Babe, I'd like to get your reaction to something."
Unsure what was coming I just raised my eyebrows at her and waited.
"You know by now that one of my juiciest fantasies is fucking another man, right?"
"Yeah," I said, "we've played that one out a number of times to the satisfaction of both of us."
"Well," she said with a thoughtful look, "I might be ready to make it a reality, but only if you're comfortable with it. I would only do it if you were with me when it happened, and I think I would only consider involving Courtney and Steve if they were willing, no one else. Courtney would have to be there too - I would kind of feel like cheating on her if she wasn't involved somehow. If anybody objects or isn't entirely comfortable with it, I wouldn't want to pursue it. Also," before I could reply, "I don't want you to answer right now; I want you to have time to think about it before saying anything. Remember we said either one of us could have veto power over any decision like this, and I will stick to the promise not to be resentful if your answer is no. I haven't said a word to Courtney about this; if you say no, nobody will ever hear about it."
I wasn't exactly blindsided by this concept; we had discussed whether we would consider this at some future point, and Theresa had so far said she wasn't into actually doing it with another man. Therefore I had kind of considered it and done a little fantasizing about it, but had been able to avoid seriously considering how I felt about it up until now. Ever since Ree had opened up to me about her core fantasy, I had been aroused and kind of ashamed of my arousal at the same time when I thought about her having another man's cock in her mouth or cunt and taking his cum in either place. We had role-played a scenario where I had fucked her after her outside lover (me in that role) had just come in her before I fucked her again, and I have to admit that I was super aroused just playacting it. Sexually, I was way into the concept of sliding my hard cock into Ree's cunt while it was dripping with another man's cum, but I also felt somehow wrong about feeling that way. Neither one of us was into the stereotypical "cuckold" fantasy with its humiliation and dominance/submission overtones. I knew if we did this it would be sweet and loving between all parties, but I still felt like I was failing at some aspect of manliness if I were to accede to this fantasy, notwithstanding that it seemed both of us were interested. The emotional aspect of this was really complicated even before we got the concerns about whether one or both of us would feel uncomfortable, left out, or resentful after the scene had been played out. The easiest thing was to avoid acting the fantasy out in real life, and that's what we had been doing so far, and so far I was comfortable with that. I felt this was a really big step.
My mind was buzzing with a flood of images: Theresa on her hands and knees with Steve pounding her cunt from behind, me licking Courtney as I listened to Steve make Theresa come, Courtney riding my cock while I watched Steve spill his cum in Theresa's throat. Ree was right, this wasn't the best time for me to make a decision of this magnitude. I also thought wryly that I was glad she waited until she had fucked me limp before bringing this up, as I would be embarrassed by what I was sure would have been a raging erection otherwise.
Trying to be matter-of-fact about things, I replied, "Well, I won't say no right off the bat, but I think you're right about needing some time to consider things." I smiled at her. "No matter what happens, I love you, and it's so arousing for me that you're confident enough to bring this stuff up. I know it's not easy, and I love you for being willing to put yourself out there like this."
"Thanks, honey," Theresa replied, "I can be confident cause I know you love me and I know our sex will continue to be hot no matter what we decide."
We kissed and then drifted off to sleep. I had some very interesting dreams that night which I kept to myself after I woke the next morning.
I rarely get very anxious about anything or do much worrying at all, but I have to say as the next few days passed, I was actually agonizing over the decision that Theresa had presented. I framed the decision to agree to Ree's request in the light of wanting to give her what she wanted/needed and sold it to myself that my heart was big enough to encompass her desires as I was confident in her continued love for me come what may. Or was that come who may? I was able to be humorous about it sometimes.
The thing that I had the hardest time with was trying to be honest with myself that I actually had been looking forward to this experience ever since Theresa had first brought it up as something she fantasized about. I was relieved when she initially said she didn't want to enact this fantasy in real life as that allowed me to avoid deciding what I would actually do while allowing me to really get into the role-playing aspect of it and get my satisfaction with the concept of Theresa fucking someone else without having to deal with the reality of it. Now that it was "showtime" so to speak, I had to admit that my cock had always gotten hard thinking about Ree sucking and fucking another man and making love with her after. My cock was getting hard right now just thinking about it, and my dreams had been rife with images of cum dripping down Theresa's ass after a session with her lover. I was reluctant to admit it to myself, but I was almost as aroused by the thought as Theresa said she was. Wow, what a lot to take in.
The most important part for me, then, was trying to predict how our relationship might change if we made this big sexual step. I had some deep and constructive conversations with Theresa on this subject during these days of indecision, and I began to feel that even if things didn't turn out as well as we hoped, a single experience wouldn't negatively impact us as long as we were truthful with each other after and allowed the veto power to be used if one of us didn't feel absolutely comfortable with this kind of activity in the future. Thinking about it as a one-time thing made it easier for me; we could figure out the future after. Even if I felt bad after, we didn't have to repeat the performance. That made me feel better about agreeing with the scene which I knew I wanted to do in some deep place in my sexual psyche.
One night about a week after Theresa proposed that we make her "outside man" fantasy a reality, I had a conversation with her in which I stated my acceptance of her proposal, laid out the boundaries I would feel comfortable with, and agreed that she could discuss all of this with Courtney and/or Steve to sound them out on what if anything they would be willing to do in this scenario.
I have to say I was waiting with some apprehension for Theresa to talk to Courtney so I could hear what the decision would be. I partly hoped she would decline, so I could avoid the whole thing, but I was deeply hoping in the sexual part of my being that she would say yes. The dissonance kept me uncomfortable every time I thought about it while I was waiting for Theresa to find the right time to broach the subject with Courtney, then for even more days after she did to wait for Courtney and Steve to discuss it and get back to us.
One evening when I got home from work, Theresa was waiting for me with such a big shiteating grin that I knew before she said a word what she was grinning about and what the answer had been.
"Yeah, you know what I'm gonna say already, don't you?" she said with a laugh, "or at least some of it. Yes, Courtney said she and Steve are willing to help me - us?" she asked with a raised eyebrow, "cater to the fantasy I laid out for them. I was real general, we can fine-tune things and they are willing to pretty much 'follow orders' from us when we're together."
"Oh, man," I said with feeling, "I've been pretty anxious about this, but I gotta say I've been more turned on the past few days than anything else. I do get the impression that there's more, so spill Ree!"
"Well, things have obviously changed for me since we first played with Court and Steve, and they've acquired a good bit more kink than they had then, too. I talked to Courtney a few times and at length about wanting to make sure that she in particular was OK with Steve fucking me and wanted to make sure she had thought out the possibilities about what might happen not only with their relationship but also with our friendship. She says they talked everything out and feel like you do that we're only agreeing to a one-time thing right now that might not happen again if they don't like it for some reason. She said that made it easier to think about, and therefore they agreed. She did mention that she was really aroused by all the possibilities that came to her fertile little mind, and Steve would do just about anything I asked of him after our last encounter."
"Oh, yeah," I said, "I think you made a real impression on him. Was he disappointed that he won't be able to fuck your ass? He was so intent on watching my cock in and out of your ass the last time that I thought he was going to pass out!"
"Courtney didn't say, she just said they agreed to our boundaries in all respects, and no anal with me was clearly one of them."
In our first fantasy scene with each other, I had playacted the aggrieved husband demanding that anal sex be reserved only for me even if his philandering wife couldn't deny her desire to fuck other men vaginally. We kind of liked that exclusion now in reality, thinking it would be nice to keep something just for ourselves, so had put that into the list of boundaries Theresa had set in proposing this scene with Courtney.
"My conversation with Courtney was very interesting, though. She's much more open to participating physically with us this time, which I'm guessing you'll be really happy with. She said she's looking forward to fucking you, but her boundary around that is that you wear a condom. As you know, I don't have that limitation with Steve, as part of our kink in this scene is that he cum in my cunt, right?" I nodded and she continued. "She said she wasn't into anal; I quizzed her on this a bit and she felt comfortable telling me that she and Steve have indulged in some anal play, but not fucking yet. She sounded like she was close to getting there, but has not yet. She did say she now understands what I was talking about when I said how much I like your tongue in my ass, so I guess they have graduated to that point, and she seems to like stimulation there. When I specifically asked her she blushed a little but said your fingers and tongue are OK in her ass. I sort of playfully acted disappointed when I asked why not my fingers and tongue, and she blushed bright red and muttered something like 'well, OK if you really want to'. She also said she wanted to suck your cock bare as long as you can make sure you don't come in her mouth. I got the impression that that was something she wanted to limit just to Steve. I don't think that she's nearly as happy to have cum in her mouth as I am, and she wants to give that gift only to him."
"One thing I have been realizing for a while," Theresa went on, "is that we won't be able to work everything into one experience; we'll have to hit the high spots and let the rest flow as it will. I'd love to get some time in between Courtney's legs to see what it's like to make another woman come, but that might not be possible with everything else that I really need to have happen."
"Shit, baby, you never said anything about wanting to lick pussy before!" I blurted.
"Yeah, well, I've opened my horizons about a few things during these conversations with Courtney. Sounds like their biggest strides into anal sex have been with Steve on the receiving end." I raised my eyebrows in surprise. "Yeah, I know. Anyway, Court says she has started pegging him and both of them really, and from her expression I mean really, like it. She says this opened up something deep in Steve, and he has been talking about taking a real cock in his ass and wanting to feel someone come inside him - can't get that from a dildo. Courtney says she has gone through some changes about this and has come to acceptance; sort of like you have with my desire to be fucked by someone else. She is really into fucking his ass herself, talked a bit about buying a strap-on harness and picking the right dildo for his ass - she got pretty emotional just talking about it. I'm thinking she was getting a bit wet right then, too. Anyway, she said they weren't ready to talk about asking a man to fuck Steve - I got the impression it would be you they asked if they ever did - but she did ask how you would feel if he sucked your cock. Sounds like he is starting to get into his new identity as a bit of a cum slut; she says he has started licking his cum out of her pussy after they fuck sometimes and also wants her to give him his cum from her mouth after she sucks him off. She said he really wants a man to cum in him and he'd be okay with oral but not anal now."
"Hey, you put her up to that!" I accused.
Theresa put her hands out, palms facing me in the classic "halt" pose. "Hold on, hold on, I absolutely did not! I hadn't even told her that that was part of my fantasy world. I almost couldn't even admit that to you, and I wouldn't have the nerve to tell anyone else, even Courtney. This has nothing to do with me, it's a request from Steve, and it's totally up to you to decide yes or no."
"Wow, I really don't know...it's not really anything that I have much feeling about, not really turned off by it, but...I'm definitely not into reciprocating. I think cocks are interesting, like the way they look and am kind of fascinated by the variation in size, shape and coloring, but...they just don't get me excited. I do enjoy having my cock sucked, I have to admit, but..." I trailed off.
"Well, if you want, and don't get me wrong, I'm not trying to talk you into anything, I'm sure I could get Courtney to make things very interesting for you while Steve takes your cock down his throat. I say Courtney because, as you know, I would be wanting the front-row spectator seat to watch. And probably kibitz, to boot!"
"Fuuuuck!" I breathed, "you actually make it sound intriguing. I'll think about it, anyway."
"Can't ask more than that," Theresa replied.
We continued to discuss the scenario, agreeing on what acts would be the highest priority, and wondering about how it would all come together in reality. For some things, the ability to watch for either of us was important, and we realized that it might not be as easy as we hoped to end up in the right positions to make that happen. We agreed that we would go to Steve's house for this experience; Courtney said she would be most comfortable there and we had some good history with all of us making love there in the past. After a while, we figured we'd done as much planning as we could, so Theresa resolved to talk to Courtney the next day and set up a time for the festivities.
The day came around after much anticipation and some anxiety if we were being truthful. We arrived at Steve's house in the evening and were ushered by him straight into the den which was set up much the same as the last time we had all played with each other there. Candles (already lit this time), pillows, mattress and bottles of lube in convenient places. Courtney immediately said she didn't want us to be nervous, and pulled us all in together for a group hug. She thanked us for coming over, said she was sure we would all have a really good time, and told Theresa she and Steve were honored to be the ones to make her fantasy a reality. She then looked at me, and said, "I'm sure we can figure out how to keep occupied while they're getting incoherent fucking each other's brains out!" We all laughed, and what tension there was in the room ebbed away.
Theresa spoke up next, "We're here because all of you have been generous enough to help me do something I have been dreaming about for years. I can't thank you all enough for that. I think it's important to say a few things before we get started. This isn't a role-playing scene, so 'no' means 'no' and we shouldn't feel rejected if we hear that. I personally don't like pain with my pleasure, so if I say "ow!" that means stop, or find another way to do that so it's not uncomfortable. Anyone else with me on that?"
"That goes for me, too," Courtney put in quickly.
"And me," I said.
"Likewise," Steve added.
'Good, so we shouldn't have a need for safewords tonight, just listen and be respectful. As far as boundaries, we should state them now so there's no confusion. I'm up for anything that seems good at the moment, except that Phil is the only one allowed to put his cock in my ass. Courtney has told me she doesn't want to be fucked anally, but fingers and tongues are OK," she paused and raised her eyebrows at Courtney who nodded. "Right, and she wants Phil to wear a condom if they fuck vaginally. So what happened to Miss Look-But-Don't-Touch from last time, babe?" Theresa threw her a devilish grin.
"That was to make my performance more effective," Courtney explained. "I wanted to make you eager to have me but then whining with frustration because you couldn't do anything about it. I figured it would be better if you thought I was just shy and inexperienced because that was the persona I was playing. I was way turned on by how much you guys had to hold yourselves back. When Phil told me he wanted to fuck my ass with his tongue, I almost lost it and relented, but caught myself just in time. I think he wouldn't have come so hard on my tits without the frustration, and seeing you pounce on him and smother his face with your cunt after that, Theresa - fuck, I still think about that sometimes when I'm getting myself off."
"Not as reluctant as you let on, huh? You're probably right about how ramped up we got that way, though. Anyway, tonight, Phil says he's open-minded to anything and wants to make decisions as opportunities arise. Steve wants it all, but Courtney wants to reserve fucking his ass to herself." Steve blushed furiously. "Do I have all that right?"
We all nodded and Theresa continued, "I want Phil to direct the festivities at the beginning; everyone is welcome to help him get me ready for Steve," she gave him a sultry smile that must have gone straight to his cock from the lustful look he returned. "But I want just Phil to fuck me for the first little bit. After all the effort we all put into making this happen, I still feel a little self-conscious and I think this will help me get into it." Murmurs of assent all around. "This isn't really a boundary, but," she said steadily gazing at Steve, "I really want Steve's cum in my cunt at the end of the night, so no condom if you two are OK with that."
"I'm fine with it, as we said the other day," said Courtney, and Steve just nodded with a big smile on his face.
"We really are overdressed," I said with a smile and began taking my clothes off and piling them on a chair. Everyone was bare in a short time and I directed Theresa to lay down on her back in the middle of the mattress. As I crawled up between her legs, nudging them wider, I suggested to Courtney and Steve that they occupy themselves with kissing and caressing Theresa above the waist. They kneeled on either side of her, running their hands over her belly and breasts.
I kissed the insides of Theresa's thighs, lightly brushing her mons with my lips when I went from one leg to the other. Theresa was soon relaxed and humming under our ministrations. I moved back so I could get a better view and began massaging the soft hair-covered area between her labia and the crease of her thighs, working up to include her mons but avoiding her clit. I kept this up for a few minutes, my cock starting to stir as I watched Courtney kissing Theresa deeply on the mouth while Steve suckled a breast, and then trading places as Courtney sucked on Theresa's other breast.
Moving forward, I parted Theresa's pubic hair with my thumbs and drew my soft, flat tongue up over her labia from the bottom to her clit at the top, getting her a little wet. I then slicked my thumbs with my saliva and moved them up and down the grooves just to the outside of her labia, pressing them in toward each other to massage her lips lightly and pinch her clitoris just a little as it lay dormant under its hood.
I began licking her labia again, keeping up the massage with my thumbs, allowing her lips to stay furled, sliding up over her clit, but with little pressure. I continued like this until I began to perceive her scent a bit stronger, then I plied my tongue more insistently, finally parting her labia and dipping a small way into her cunt, opening her lips as I moved up to and over her clitoris. I flicked that bud quickly side to side, then slowly licked down to enter her cunt again. I licked up and down between her labia, slow and steady, breaking off to flick her pearl once in a while in the way I knew she loved. Ramp it up, and cool it off, over and over was her preference, at least in the preliminary stages, so that's exactly what I did.
It sounded from Theresa's soft moans that she was sinking into arousal, and I could tell that the attention she was getting from Courtney and Steve was much appreciated. Courtney took some time off from sucking Theresa's nipple and tongue to tell her how beautiful she was and how arousing it was to be caressing her while I was licking her. I noticed Theresa had captured Steve's cock in her hand and was stroking him slowly.
"Come up here," she told him, and he rose on his knees and brought his glans up to her face. She turned her head toward him, and captured his cockhead in her mouth, sucked him lightly and pulled off to say to Courtney, "You want to help me out with this?"
"Mmmm, yeah," Courtney said and leaned over, breasts pressed against Theresa's, and told Steve, "fuck me," while opening her mouth just in front of his cock.
Steve slipped his cock between Courtney's lips and fucked her mouth shallow and slow.
After a short time, she pulled her mouth off him and said to Theresa, "Your turn."
Theresa opened her mouth, her head turned to the side, and Steve fucked it sweetly also. The women took turns with him like this, keeping the energy low for now.
I amped up the wattage on Theresa's cunt, licking it faster and more insistently, pulling her clitoral hood back with a thumb to gain a direct connection between tongue and pearl. I moved up on my elbows enough so I could slide a finger halfway into her cunt and she purred, closing her eyes and rolling her head back, letting Steve's cock fall from between her lips.
Courtney grasped Steve in her fingers, stroking him and occasionally sucking his cockhead, but mainly watching with interest as Theresa started to reach another level of arousal.
I rose up from between Theresa's legs, cock standing hard in front of me and Courtney looked down at my erection. Assuming I was moving to start fucking Theresa (she was right), she said to me, "Let me put it in!" I had been thinking to slip my cock into Ree's cunt without moving her, but at Courtney's request, I thought a new position might be best for us all.
"Can you get on top of me, love?" I asked, and Theresa murmured something that sounded like assent.
Courtney moved away and I lay down next to Theresa, who rolled over, threw a leg over me and rose up on hands and knees over me. "Yeah," she said, "put him in, babe, that would be really nice."
Courtney came up behind Theresa, pushing on her ass to move her up toward my head far enough to get the room to put my cock in her mouth for a few thrusts, making me nice and wet. She took her mouth off and grinned, "I seem to remember something about more lube is better," she said wickedly, "I think he's nice and slick now."
Theresa moved down again, raised her hips up above mine, and Courtney took the base of my shaft in her fingers and slid my crest a few times between Theresa's labia, then positioned it at the opening to her cunt. "There you go," she said, continuing to grip my shaft, and Theresa let herself sink down, taking me into her luscious depths. She opened her eyes a little wider in mild surprise to feel Courtney's fingers still around me, then smiled and rose up off me slowly.
"Take him a few times and then give him back to me," Courtney instructed, "I want to taste you on him." My cock leaped inside Theresa - was this really happening?
"You're the demanding one, huh?" Theresa said in an amused tone. She slowly posted up and down on my phallus, then came off entirely, sitting down on my belly, then scooting up toward my chest, trailing a damp line up my torso from her open cunt. "He's all yours, babe."
Courtney pointed my tip up high toward her mouth and sucked me in, humming with pleasure as she sucked Theresa's juices off my shaft. Theresa lifted up off my chest, arched her back and lifted her ass toward Courtney. "You liked that, huh?" she said in a throaty tone, "maybe you'd like to drink directly from the well, hmmm?"
Courtney dropped my cock and gazed up at Theresa's spread labia. "Fuuuck...I never licked a woman's pussy before....but you definitely look good enough to eat..." she sounded taken aback by Theresa's offer, a bit conflicted. She reached out and ran a finger down Theresa's pink core. "Oooh, you're like silk," she said, then with sudden resolve she moved up toward Theresa's alluring bottom and ran her tongue up that slick groove, brushing her breasts over my cock, then sucking Ree's labia into her mouth. She lapped up a bit of cream from the opening to her vagina, and quickly broke contact, licking her lips and swallowing with a look that equally measured surprise with arousal. "Yeah, I might be able to get used to that..." she grasped my shaft again. "Here, take him again." She put a hand on Theresa's hipbone and guided her back, lining up my cock so she could slide back onto me in one motion.
Moving back a bit to watch my shaft reappear and be engulfed again as Theresa began thrusting up and down over me, Courtney sighed, "That's so hot, you two. Steve, come over here and watch this - you're going to be right here soon, love. Fuck, this is quite the show!"
Theresa leaned over me, holding herself up with her hands on the bed so her breasts swung free. I reached up to massage one and twist her nipple gently as Steve moved down next to Courtney behind Theresa's bottom. I began thrusting up to get deeper inside Theresa and she moaned, "Mmm...yes...some fingers on me would be really nice," not really directed at anyone. I heard what I thought was a lube bottle cap opening, felt Courtney slide her fingers next to my cock to stroke Theresa's clit and heard Ree's breath catch in her throat as Steve ran slick fingers over her anus.
"Deeper," she demanded and I chose to hear that as instructions for Steve as I continued my slow thrusting and didn't try to increase my depth inside her. "Oh, yes!" she exclaimed and I assumed Steve's finger was sinking into her further as ordered.
"You can try two fingers at once," I told Steve, "she likes that most times."
"Ooh!" he said sounding startled as if that had never occurred to him. Theresa's gasp and feeling her push her ass back harder told me he had indeed found that sometimes two fingers are better than one.
"Courtney," I said, "why don't you make sure Steve is ready to take over for me here? I think Theresa is more than ready for him, and I would like to watch a nice show for a while."
"Oh, Jesus, babe!" Theresa grated, "the thought of you watching me fuck him...Oh my God..."
I slowed then stopped thrusting, pulling her hips down to me, slow enough to allow Courtney to get the idea and move her hand from between us. I held Theresa's ass tight and pressed up to get as deep as I could into her cunt. Courtney sounded like she was making Steve's cock as wet as she could, judging by the slurping sounds she was making, and he started moaning "Fuck, Court, that's so good...damn, you're taking all of me!"
I slapped Theresa's ass lightly, and she pulled up off me and I moved out from under her. She looked over her shoulder at Steve who was in heaven with his eyes closed, cock in Courtney's mouth to the root. "How do you want me, babe?" she asked him in a low-pitched voice that seemed to go right to my balls, and since Steve's eyes snapped open to look at her, I figured it had the same effect on him.
"Oooh..." he crooned as Courtney pulled her mouth off him, "I really want you from behind, Theresa, you're so beautiful that way..."
"If I get a vote," said Courtney, "I'd like you to start with her on top, so I can put you in and watch you fuck that way for a little while."
"We can change positions as many times as we want, if we go slow and make it last," said Theresa with a wink at Steve, "let's start like Courtney says. I really like the idea of putting on a good show while we're starting to get incoherent. Then they're on their own after we really get going!"