When an unrequited crush becomes a “requited” attraction, Emily learns that two dicks are definitely better than one.

It was 4:00 a.m., and I was still awake in the middle of my comfy hotel bed. Sighing, I threw my arm across my husband’s body and snuggled against him. Of course, he’d been asleep for a while now, having passed out soon after reaching orgasm, as so many men are wont to do.

Settling in, I hoped I could doze off despite the fact that my heart was still racing a little, but the sound of a groan from behind me, plus the feeling of a semi-erect cock against my ass, thwarted my attempt. Now not only was I awake, but so was my pussy. I was certain that Ryan, an old college friend, was also asleep, and his movement was subconscious, but with my arousal mounting, I decided that someone needed to wake up. To make this happen, I spurred Ryan on by grinding my ass against his burgeoning erection.

His cock responded to my efforts by thickening and lengthening, and in the process, his erection nestled lengthwise between my cheeks. I knew he was fully awake when I felt him nuzzling the nape of my neck, so I continued moving against him to convey that I was ready for another round. He seemed to be, too, because his dick continued to stiffen until it was once again at full mast.

I really wanted to fuck him again, but I was hesitant about waking Chris because he looked so peaceful lying there beside us. With Ryan’s tempting lips still trailing over my flesh, raising goose bumps wherever they touched, I gingerly lifted my arm from my husband’s side and turned to face my old friend.

Ryan and I stared deep into each other’s eyes before our lips met. His parted, so I slipped my tongue between them. In return, he palmed my breasts and played his fingers over my nipples, which were still so sensitive from our earlier endeavors that my body reacted instantly, giving an appreciable shudder. Reaching down, I took hold of his cock, pumping the shaft in my fist while massaging a bead of pre-come into the tip with my thumb. Raising my leg, I slipped his crown between my nether lips, stroking it along my slit and giving a little start each time it bumped my clit.

Ryan gasped upon feeling my wet heat and clutched my tit even harder as he attempted to slide into my slick hole. I purposefully eluded him, having too much fun masturbating with his penis. But he didn’t give up easily.

Letting go of my breast, he reached down and slipped a finger between my labia, stroking me until I moaned into his mouth. That motion felt so good, I pulled away from his hand. It wasn’t that I didn’t want him touching me; I was now desperate to feel him inside me, and I needed something bigger than his finger.

I pushed Ryan onto his back and threw a leg across his torso to straddle him. His prick bobbed enticingly in front of me: tall, proud and ready for work. I took hold of that massive cock and rose, positioning his dick at my opening and letting the head pop inside me. As I slowly lowered myself onto his staff, I shut my eyes to revel in the feeling of being stretched wide open for the second time that night. After Ryan was fully engulfed by my cunt, I rose at the same pace and then repeated the entire process — this time a little faster.

I bounced on Ryan’s dick, leaning forward so that I was crouching over him and could press my lips to his. We kissed, our tongues tangling, and I kept my eyes closed so I could concentrate on all the sensations I was feeling. And since I couldn’t see anything, I assumed it was Ryan caressing me when I felt a hand on my lower back. Though, it didn’t take me long to realize that hand belonged to my husband.

I opened my eyes and looked at Ryan, who winked at me. Then I glanced beside us and saw that Chris was wide awake. He also gave me a wink as he traced patterns on my skin, and the sight of his fully erect cock told me he’d been up for a while, watching me ride our old friend.

I invited Chris to join us with a smile, so he rose to his knees and kissed me. Meanwhile, Ryan grasped me by the hips and began moving me over his dick at a more leisurely pace to give my husband a chance to catch up.

As I rode Ryan, Chris’s hand trailed lower, until his fingers spanned one of my asscheeks, his thumb working its way into my crevice. Knowing how much I like having my asshole played with, he nudged the sensitive opening and then pressed against it lightly. When I moaned, he pushed inward, stretching the muscles just wide enough for his digit.

As he stroked me from inside, I realized he could feel Ryan’s movements in my other hole. This was exciting, because it was new — when we’d fucked earlier, Ryan had taken my pussy from behind while I’d sucked Chris. The thought of being doubly penetrated in this manner hadn’t even occurred to me — but now it was all I could think about.

My husband kept his thumb buried in my ass while Ryan craned his neck to take one of my nipples between his teeth. I continued rising and falling on Ryan’s dick, my movements easy and fluid. I felt his balls against my asscheeks whenever I touched down. After a few trips, I surmised that Chris must have been feeling them, too, which I found strangely exciting, especially because they’d had so little contact during our first encounter. This realization made me bounce up and down so erratically that Ryan had a hard time keeping his mouth on my breast. Though he managed to persevere, my husband was less successful at keeping his finger in my derriere.

Choosing a new tactic, Chris got behind me, straddling Ryan’s legs. My heart raced as he bent me over even further, until Ryan and I were face-to-face, and then he grabbed the lube from the nightstand and slathered some onto his cock. His fingers slick with gel, Chris slid one slippery digit into my asshole to get me wet and ready.

I almost came as he thrust into me, and then again when he pulled out and plunged back in, adding another digit. This time, Ryan tensed at feeling the pressure against his shaft through the thin membrane separating the two men. If this is how we both react, I wondered, what’ll it be like when Chris replaces his fingers with his dick?

We were about to find out. Satisfied that I was sufficiently prepped, my husband pulled his fingers from my hole. Positioning his cock, he then pressed inward slowly, and I remained still to let him penetrate me. Ryan also stopped moving, completely entranced by the sight of me having my ass filled. Looking over my shoulder, I could see the bliss written across Chris’s face, and a glance at our college buddy told me he felt the same.

With two cocks buried inside me, I held still at first, crouched on my hands and knees as the men thrust into me at the same time. The simultaneous penetration felt incredible, and I would have been ecstatic — literally — if they’d continued in that vein. Maintaining a rhythm was difficult, however, and they decided that one man would have to push in while the other pulled out, and I’d help by not moving.

I didn’t really care how we proceeded; it felt amazing no matter what we did. My pussy dripped incessantly as they pumped in and out of my holes. My breasts bounced as their movements jarred my body, and my overly sensitized nipples grazed Ryan’s chest. Both he and Chris worked hard to keep sawing in and out of my cunt and anus, and it wasn’t long before I felt a quivering in my belly, which spread through my entire body. When my fingers started trembling and my toes curled, I knew I was on the threshold of an incredible orgasm. Gasping, I struggled to keep myself from collapsing onto the body beneath mine, because that would have impeded Ryan’s ability to keep thrusting into me.

The friction of Ryan’s shaft stroking against my clit sparked my climax. I buried my face against his chest as I lost control, while he and my husband held me tightly and continued pumping into me. Soon, Chris was coming, too, as he slammed into me one last time. Moments later, Ryan’s shaft quivered in my pussy as he filled me with his cream.

Demolished, we collapsed in one big heap, remaining a tangle of arms and legs as we slowly returned to our senses. Once we did, the men gently disengaged themselves, and then we settled back among the messy pile of pillows and bedsheets. After that workout, I had no trouble falling asleep, but since it was nearly dawn and a few hours from checkout time, I can say that none of us got much rest that night!

After hearing that part of my tale, you’re probably wondering how all this started, how my husband and I — not necessarily all that sexually adventurous — ended up in a threesome with one of our best friends. It wasn’t totally unplanned. One night, while sharing a bottle of wine, Chris and I got to talking about unrequited crushes, and I happened to mention Ryan.

“Really?” Chris said, and I could practically see the light bulb go on over his head. “You know, the reunion is coming up, and I’m pretty sure he’s single.”

I was aware the reunion was coming up — a weekend affair at a swanky hotel — and apparently, so was my pussy, because it tingled at the thought of being near Ryan again. However, I couldn’t see myself fucking a former love interest while my husband was somewhere else making small talk with barely remembered classmates.

“What makes you think I won’t be there?” he asked, and I suddenly understood what he was getting at. When we’d talked about having a threesome before, it was always a playful conversation. This time, he was serious. And I could tell he meant business because his cock got big and hard, and the sex that followed was mind-blowing.

At the reunion a few months later, it took us about a day of reacquainting ourselves with Ryan to work up the nerve to invite him into our bed. It was my job to break the ice with a lot of flirty looks and longer-than-necessary touches. My feminine wiles must have worked because when I finally propositioned Ryan, he almost seemed like he’d been waiting for my advance. And since the evening was the last night we’d be together at the hotel, we wasted no time.

The three of us were already in our room, having retired there for what we’d simply said was a “nightcap” to celebrate a long day of festivities. When Ryan had said yes to my threeway suggestion, I moved closer to him on the couch we were sharing, wound an arm around his neck, and pulled him toward me for a kiss. Meanwhile, Chris moved from his chair to the cushion behind mine and reached around to fondle my tits.

As we made out, my hand found its way to Ryan’s lap, and I traced the outline of his erection through his jeans, a scenario I’d fantasized about so many times, albeit twenty years earlier. I unzipped his fly and pulled out his member, wrapping my fingers around his shaft and stroking it lightly until my husband suggested we move to the bed. We did just that, but not before we all undressed.

When Ryan was completely naked, I paused to admire him, sprawled on the mattress as he was. His body was as beautiful as I’d always imagined, and as I ran my fingers over his chiseled chest, he took in my medium-sized but still firm breasts. He leaned forward and, after kissing each one of my nipples, trailed his lips downward until he reached my sex. I parted my legs, shivering when he swiped his tongue along my slit.

"I felt a thump in the pit of my belly every time his sac bounced against my asscheeks."

Chris and I both watched, entranced, as he lapped at my pussy, the first man other than my husband to do so in many years. He dragged his tongue over my quivering folds and flicked at my clit, licking me until his lips and chin were slick with my juices and the sheets beneath me were balled in my fists. It was the sort of thing that normally would have made me come rather quickly, but I was too distracted by my husband’s cock, which was now in my mouth.

The oral daisy chain continued a while longer, until Ryan changed the game by thrusting a finger in my cunt. He stroked in and out of me until I yearned to feel his cock. While my husband fucked my face, I blindly tugged at Ryan, hoping he’d take the hint and replace his digit with his prick.

We were once again thwarted by logistics. In order to keep Chris in my mouth and have room for Ryan between my legs, I had to remain propped up; lying down wasn’t an option. Ever the problem solver, Chris pulled his length from my lips and repositioned us so that I was on my hands and knees and Ryan was behind me, already lining up his cockhead with my cunt. Meanwhile, my husband knelt in front of me, his dick barely an inch from my face.

I captured the tip in my mouth just as Ryan grasped my hips tighter and pushed forward to pierce my pussy. Chris and Ryan both started sawing in and out at the same time, and I grabbed at the sheets to steady myself. Once stable, I swished my tongue over the underside of my husband’s shaft, increasing his pleasure while increasing Ryan’s by squeezing my muscles around his girth. He responded by shoving into me even harder, and I felt a thump in the pit of my belly every time his sac bounced against my asscheeks.

Threading his fingers through my hair, Chris held my head still as he repeatedly skimmed his length over my tongue, burying himself to the balls each and every time. I swallowed hard, letting him feel my throat tighten around him. Then, when he pulled out, I sucked on his crown for a while, delighting in the saltiness of the pre-come trickling from the slit. I also delighted in the feeling of Ryan pounding into my pussy from behind. He was gripping me tightly to keep me steady, his fingers digging into my flesh as he held me by the waist.

As the men fucked me, Ryan reached beneath me and pressed his fingers to my clitoris. My entire midsection — from my stomach to my asshole — started humming. I was already seeing stars, but I had yet to really explode.

I was on the brink when Chris beat me to it. As I felt myself about to reach my peak, his shaft seemed to expand, and then I was treated to a mouthful of his cream. I started coming a second later, shaking so hard that I had difficulty gulping down his load, so a lot of it ended up streaking my chin and dripping onto the sheets. Another byproduct of my orgasm was that my pussy clamped around Ryan’s still-thrusting member, squeezing his shaft more tightly and forcing him to thrust into me more vigorously.

Luckily, he only needed a few more pumps before he joined us in our ecstasy. Shouting his bliss, he crashed against my asscheeks one last time and then shot the contents of his balls deep into my chasm. I had never before experienced the joy I felt at having two men pumping me full of semen at the same time, all while I was in the throes of my own orgasm. Of course, little did I know then that this experience would soon be trumped by my very first DP only a few hours later.

For the moment, having one dick in my mouth and another in my cunt was more than enough; in fact, it was almost overwhelming. And both men remained inside me until their balls had been depleted and my pussy was no longer contracting. Pulling out first, Chris stretched out beside me, and I leaned down to give him a kiss while our friend gave me a few last thrusts that elicited one final orgasmic shudder from me.

We invited Ryan to spend the night in our room, which is how my very first threesome was quickly followed by my very first double-fuck. Overall, it had been a memorable weekend. Hopefully, it won’t be another twenty years before we see Ryan again, because now that I’ve had the experience of having two holes filled at once, I don’t know if one cock will be enough to satisfy me.

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