Lisa Cuckolds Jake

I met Summer, what – 1999…? – 14 years ago. New job, new folks, new city.

I was married at the time to someone I knew I should never have married (a straight girl who never grew up; different story) and while there were many opportunities to take that right turn and keep on going, I was always faithful. Until my wife wasn’t.

Divorce was painful but there was one part of me that I’d always ignored – speaking of knowing better – that I took solace in: At least with having my own place I could finally indulge in my “darkest” fantasies without fear. I quote “darkest” because I was afraid of – and tantalized by – my true sexual nature.

I’m queer.

Bisexual, if you like, but I like queer because I like fucking all sorts of hot people – men, women, transwomen, whatever: As long as there’s a connection, I’m down to play.

Anyway, I moved out, got a place of my own and started to explore my sexuality. After I finally went to the bathhouse and sucked my first cock (tiny, disappointing, but so freeing nonetheless) I came out and the first person I came out to was Summer.

She’s a butch dyke and ever since I met her I’ve been attracted to her. This was odd to me because…she’s a butch dyke. What would she want in me, right? I have a cock, which she wants none of, so what could possibly happen? Anyway, point is, fucking was a non-starter but we were fast friends for reasons I couldn’t admit to myself. Basically, we’re both family: She was out, I wasn’t, but still, family. And so of course, she was the first one I came out to 5 years ago.

Since then I’ve fucked a lot of women and sucked a lot of cock. About a year ago I met Lisa. Oh. My. God. Lisa. 5’5″ of tight, caramel-toned, brown-eyed faggotry topped by an amazingly intelligent mind, this woman is my perfect match. Also queer, she and I couldn’t be more perfectly suited for one another. B-cup, round ass, tight, tight, tight body and tighter pussy, she’s more than I ever hoped for. See, as I explored my sexuality, I found that not only am I queer, I’m kinky. I’d be specific, but that would take too long and this isn’t Proust; I want you to come soon. Point is, I found that I’m a Switch with a strongly submissive preference. I love to bottom and to serve. Especially to do so for dominant women. And Lisa is a Dominatrix. Yup, my Girlfriend is a smoking hot Domme and to top it off (pun intended) she loves seeing me take a man deep in my throat. And in my ass. Which I’ve done often and well, if I do say so myself.

I’m Jake, by the way: 5′ 11″, 175, long, brown hair, blue eyes, nice smile with a few crooked teeth, covered by a set of full lips. My ass is tight, eager, and accommodating (more on that later), my mouth welcoming, and my mind very, very creative.

Anyway, one of the things I learned about my submissiveness is that none of my fantasies is stronger than the cuckolding one. I’ve never come harder than I do when I’m thinking about Her fucking someone else, someone strong, hot, and with a cock bigger than mine.

I forgot to mention above: I’m 7 1/2″ and fairly thick. And it’s gorgeous, my cock: Cut, with a beautiful shape all around, along with a perfectly proportioned set of balls below it. I wish I could find one as nice, honestly. Or suck it, but again, that’s another story.

Anyway, cuckolding: It really sends me. And sure, it frightens me, as well. But what I couldn’t wrap my head around was just that: The risk of losing my lover to someone else seems likely, as good a catch as she is…why the hell would I want to tempt fate? But that’s really the pull of cuckoldry: It’s edge-play. Boundary pushing. It’s a power exchange of the strongest order and it. Is. Incredible. Especially when your Dominant Lover hears your fantasy, considers it well over time. And consents.

That’s where Summer comes back into the picture.

About a month ago I got a text from her asking me out for a beer. “Big news” was on the agenda and I had an idea of what was coming. She was divorcing her long-term partner. She needed to connect with her friends and more importantly, she needed to get her fuck on. Not with me, mind you, she’s a dyke, remember? It’s just that that was the theme of things over beers.

I totally sympathized with her, having gone through that stuff fairly recently, myself. As we were into our nth beer each I finally stopped pushing off the notion that our chemistry was possibly generating more interest than one might expect. I told her, laughing, that if she ever needed to top a boy, I’m available. Pulling the glass from her mouth, she stared at me with a half-smile and said, “I’m sure that could happen.”

Um…

Anyway, we had a great time, flirting like that – good friends who are attracted to each other for various reasons but who have no chance of having any romantic relationship – and then went our separate ways. When I spoke with Lisa that night I filled her in and suggested that perhaps she might be interested in meeting Summer and her c-cups. Summer’s body is beautiful, very feminine, while her face is rather androgynous, which is a natural turn-on for me. She’s a Top, 5’6″ with short, brown hair, green eyes, nice ass and legs, and is a total dude. What’s not to like?

Lisa and I agreed we’d hang with Summer, no expectations for what could happen, which is of course the best way to ensure something will happen :). Or at least to be very pleasantly surprised when it does. And it did, for the three of us.

See the two of them talked and we met together and really hit it off. They agreed that it would be rather fun to put me into some really compromising positions. So we made a playdate. Looking back at my text messages as I write this, I see that it was last Sunday, around noon, that I pinged Summer:

“Soooo…When do you wanna come over? W/we’re going for coffee in a bit but should be back in an hour or so.”

“I just need to shower and pull my shit together. Wanna say 2?”

“2 it is”

That’s how it started.

Lisa and I went for coffee and Summer got showered and her shit together and 2 rolled around. At the last minute I decided to go to the store for something, hoping that by the time I got back I’d see the two of them making out but when I returned they were talking. This was fine since I was actually a bit nervous about the whole thing. It dawned on me that there was serious cuckold potential here and that was an amazing realization: I always thought of the bull being a man but when I considered that Summer could fill that bill, I was floored. I actually got a bit of a headrush thinking about that possibility.

W/we’d all discussed me being in the center of things but the fact was that Summer needed to fuck some hot women and Lisa certainly fits that description. Add to that the fact that when they met I could definitely sense the mutual attraction in both of them and I had a moment of wondering how fucking hot this could be.

In all my raving fantasizing, I didn’t even come close to the reality.

I came in, dropped off whatever the hell I bought, got myself a beer and Lisa some wine; Summer was abstaining. W/we went into the backyard, sat down on my pink blanket and chatted for a while. 2 turned into 3 and someone broke out the pipe. Lisa and I smoked a bit then She disappeared for a while. Summer and I kept chatting when Lisa reappeared wearing her sarong, tied over her breasts with the part in the middle, allowing her gorgeous thighs to peek out as she strode out to rejoin us on the blanket.

“Hey faggot, sweetie,” She said, “I brought out the claws! Take off your shirt and pants and lie down if you want a scratch.” As she said this she pulled out 5 sharpened pieces of steel, about 2″ long, attached to rubber-coated rings, and placed them on each manicured finger, slowly. I jumped up as Summer looked on with that sexy-as-fuck half-smile and followed my Mistress’ suggestion. Summer’s smile widened to a shit-eating grin as she saw the raspberry-colored panties with the pink lace trim that I was wearing.

“You like?”

“Heh…Fuck yeah, I like,” she laughed.

“We both like, faggot, now lie down like a good bitch,” murmured Lisa. I obeyed and seconds later felt the needle-sharp points gently moving down my back, etching super-fine lines into the skin, my histamines quickly converting them into thin, red, undulating rivulets. Summer watched, lazily, smiling. Lisa simply had her fingers spread, palm down, and was gently pulling her fingers down and across my back. The points were trailing so I wasn’t going to be poked; the experience was enthralling, the best back-scratch, ever.

“Uggghhh, dude, this is the best back-scratch, ever, Summer,” I moaned, face-down in the gayest picnic blanket in my city. “You should try this.”

Pulling her shirt over her head: “Ok faggot,” she said, picking up on Lisa’s lead, “move over.”

God she has great tits: Lisa and I caught each other staring and smiled at each other as I moved and Summer took my place. Not for the last time.

Lisa pulled some nice moans from our playmate as She played Scary Finger Painting all over her back. After a while, I mentioned that I was getting cold and suggested that while they could stay outside if they wanted, my frilly ass was chilly, and that was no good for anyone. Without waiting for an answer I slid inside to my bedroom, which had been warmed by the afternoon sun.

I didn’t need to wait for an answer: I may be a cheeky bottom but I know when I won’t be reprimanded. A few moments later I was joined by two incredibly hot women, both of whom had wicked smiles on their faces as they saw me bent over, pulling out my favorite toy, of late: A copper-colored silicone fisting toy, with small fingers at the top – about 3/4″ across – widening in successive stages marked by rings to a base with a circumference of 10″. Only a few nights later would find me taking the whole thing but again, another story.

“Summer,” I murmured, eyes downcast and smiling, “if you and Lisa don’t mind, I’ll be over here for a bit with my new friend. I may join if you guys want me to but I’m rather taken with the idea of playing here and watching you two, for a bit…”

Grins and clothes being taken off were the only answer I received as I set the toy on the ground beside the bed, lubed it up liberally, kneeled, and slowly lowered myself until the fingers were pressing against my pussy. As Summer grabbed Lisa and kissed her I moaned along with them both as I began my slide down my new boyfriend’s length, his ever-increasing girth widening my hole.

Lisa pulled Summer down on top of Her while spreading Her legs, triggering Summer’s instinct to slide her gorgeous, powerful thigh up to Her pussy. Lisa is vocal, in such a good way. Her noises are encouraging and effective. On everyone present: As Summer’s ministrations elicited a groan of satisfaction from Lisa, my pussy opened just a bit wider as I slid over the first ring of the toy. I couldn’t talk, only grunt, as I saw the hottest sight I’ve ever beheld in person: My beautiful girlfriend fucking my friend’s thigh as she neared orgasm. The gasp that escaped my lips as Lisa’s arms wrapped around Summer’s neck, as her tongue searched for contact with Summer’s, caused them both to look sideways and smile at me, kneeling astride a fat toy, clearly falling into sub-space. It was then that I realized that I had just gotten myself cuckolded.

My cock flooded to attention with this news as I touched it, smiling back at them: This, as I mentioned, is a risky bit of edge-play since for it to work both the cuckold and his lover have to love each other and the cuckolding can rip that apart rather easily. No such outcome here. I love Lisa and Summer, both. Differently, of course, but all I knew at that moment was that W/we were in perfect harmony; W/we were all in our proper places: Lisa gratefully receiving Summer’s body and I on the floor, watching, masturbating. Taking notice, Lisa reached out and gave my hand a quick squeeze to make sure I was ok, commanding firmly, “No cumming without permission, faggot,” knowing that such constraints turned U/us both on.

As I smiled at them both I returned the grip, nodding, closing my eyes, tilting my head back as I sank a little further onto my fat toy. With that reassurance, Lisa had the first orgasm of many that evening.

Did I mention that She’s a squirter? W/we’d told Summer but she was a bit surprised for a moment, looking down at my girlfriend’s – her lover’s – pussy convulsing as She ejaculated. Summer didn’t spend too much time gandering, however: She took that as a cue to nurse Lisa’s entire body, working down Her neck, shoulders, lingering over Her breasts… Her tongue work heightened Lisa’s already erect, pierced nipples to as taut as I’ve ever seen them.

I began playing with my clit a little; no lube, since I was so aroused and I wasn’t allowed to come. Finding my maximum stretch, I stopped, then slowly began to rise, letting the fist gently pull my pussy outward as my inner ring squeezed to help the process along. Exquisite. As I started fucking I heard another gasp from Lisa and opened my eyes to see Summer’s hand slipping inside Her, first two fingers, then three, then four, slowly, gently. Lisa arched her back and spread Her legs wide just as Summer resumed kissing her way down to Lisa’s clit.

With her other hand, Summer gently pinched Lisa’s clit between her forefinger and thumb and so softly placed her tongue on Lisa’s button. “UUUUUUNNNNNGGGGGHHHHH!!!!” Lisa’s second orgasm coated Summer’s hand which simply allowed her freer access to her lover’s depths, a fact they both took full advantage of. Summer continued to lick Lisa’s clit and stroke Her g-spot with her four fingers while she jacked Her off between thumb and finger. Just when Summer and I thought the orgasm was done, Lisa went even further over the edge, arms wide, fingers digging into the sheets…

I slowly increased the pace of my fucking, all of this keeping me hard as steel. Summer pulled back to appreciate the fruits of her work, her face glistening with Lisa’s juices, nipples on those gorgeous c-cups pointing at a spot just above my girlfriend’s head. She looked at me while fucking my girlfriend with her fingers slowly and just held my stare, watching me fuck my own pussy with that toy. The knowledge that she and Lisa just made me a cuckold was very. Fucking. Clear. No words, just a look: A mixture of love and domination that left no room for interpretation: She owned Lisa right then and by extension, me.

My cock swelled as I nodded, turning my eyes downward as I dropped my chin, smiling…shaking… As the sounds of her fist moving, turning slowly in her lover’s cunt filled the room and commingled with the whimpers sliding over Lisa’s tongue and lips I felt a finger on my chin. I looked up and saw Summer smiling. Her green eyes looked me over as she leaned over, “Come here, faggot.” Tugging on my chin with her thumb she leaned in and snaked her tongue into my mouth.

I was hers. For that evening, I was her bitch and was thrilled to be so. Sounds of Lisa having another orgasm confirmed that my Mistress was of the same mind.

“How do you feel, faggot,” Summer murmured.

“Right…Just…in my place, thank you, M’am,” I barely got across.

“Good girl. I like watching you take that big thing in your ass. Better you than me, though; no way anything’s getting in my ass,” she chuckled.

“Bitch is a size-queen, isn’t she,” Lisa croaked as she swam back to the surface, recovering from the wave of ecstasy that had just overtaken her.

“Well, she’s pretty fucking gay to take something like that on,” Summer leaned down to give her lover a kiss, bending her wrist to maintain her motion. Gasps were the only thing Lisa could manage as she pulled Summer in for a deeper kiss, nodding.

It was almost silent for a few moments while we all took this in, except for the sounds of Lisa’s – and now my – cunt’s being worked ever more gradually open. At this point I was on top of the second ring with my pussy being stretched open to about 4″. Stroking my clit slowly I rose up slowly to let the fingers graze my opening then, gaping a bit, I slid back down, just as slowly, feeling as much as hearing the lube squish around. I took a bit that had spread just below my clit and started stroking as I heard the bed shift.

“She’s pretty, too, isn’t she,” Summer looked at Lisa, who looked at me, lids lowered, and smiled.

“She’s beautiful.”

“Well, her turn next time,” Summer smiled at U/us both. “Right now she can just sit there and watch me fuck you.” As she said this last bit she turned to look directly into my eyes. “You do want to see that, don’t you, faggot,” she asked, “Lisa had mentioned your little fantasy about me strapping it on for her, didn’t you, Lisa?”

My heart caught. Without missing a beat, Lisa replied, “Yes I did. Jake, my dear little bitch, the more I thought about it the more I liked the idea. You know I haven’t had any pussy in a while and although I love your cock, Summer’s is bigger. And I’ll bet she knows how to work it better.”

Seeing my gaze focus at that, she continued, “She’s a woman after all so she knows what works. Anyway, this is going to happen so don’t look so surprised: You can’t put that genie back in the bottle, sweetie. Plus W/we all know you don’t want to anyway, don’t W/we?”

Summer pulled her hand out, causing Lisa to whimper just a bit, and got off her knees to stand on the floor. I loved watching her tits bounce, her hand shining with all of the cum that she pulled from Lisa. Shaking her head, smiling, she reached down and pulled up Lisa’s harness, a beautiful bit of reinforced, black rubber and stainless steel hardware. In it was a cock far fatter than mine, something I knew Lisa would love.

“Be a good girl and keep her open for me, get her ready,” Summer ordered. At my questioning gaze, she clarified, slowly, “Get off your gay-ass toy and fuck Lisa while I get sorted here. It’s the only time you’ll get to do so so consider yourself fortunate, stop gaping at me like that, and fuck her!”

I popped right off my toy, literally, and was inside Lisa in a moment. She pulled me to her, wrapping her legs around my hips, “I love you, you know that,” she gasped as I slid into her somewhat more accommodating-than-usual pussy. Shaking with desire I nodded as I reveled in Her looseness, its reminder of my status as a cuckold. W/we kept up the fucking with me holding back in spite of another orgasm: “No. Coming. Yet. Faggot,” she grunted through her little death. As I shook my head I felt Summer’s tongue joining O/ours, which brought huge grins to all faces. I immediately ceded my place and Summer took over. Breaking the kiss she looked up: “Get off, faggot. That’s my pussy. I’ll fuck it now. Right baby?”

Lisa, my clit still inside her, snapped, “You heard her, get back in your place, bitch! She wants this pussy.” That tone, the insistence in her voice, the lust driving it pulled the floor out from under me and sent me right back into sub-space. Looking right at me Summer chuckled, pulling the floor back over me: “That’s right, baby, you ready for my cock?”

As I moved off the bed, gratefully, I saw my Mistress focus completely on her lover, wrapping her arms around my friend’s neck, pulling her in for another kiss, nodding. “Fuck me, baby,” whispered Lisa.

I was beside myself, blissfully lost in sub-space, watching them make out. I settled my pussy back onto the toy as Summer worked her fat cock over Lisa’s slit, rubbing her clit, eliciting the hottest moans I’d heard that night. I fucked myself back down to just above the second ring and tried to get past it but was too worked up.

I reached for the poppers, opened the cap, and inhaled as they watched. Recapping the bottle I waited. Summer and Lisa both smiled at me then at each other as they heard me moan with the oncoming flood of pleasure. Summer spread Lisa’s leg out so I could get a clear view.