Another Spring Break Threesome

In the spring of my junior year a few friends and I went to Cancun for Spring Break. Most of us had gone as sophomores, and this year we were a party group of 8 with 2 rooms. We partied hard the first couple of days, dancing and drinking and sunning. A couple of us hooked up, but mostly we were just partying. The third night we went out to a club as usual. Only this time I was on the prowl. Three nights of sun and fun had whetted my appetite. Besides, like they all say, "what goes on Spring Break stays on Spring Break". I was 21 and had been around the block more than a couple times, and I knew how to get what I wanted. Or so I thought.

The club was hopping, the boys were plentiful and my drinks were free. As the night went on, I saw a cute guy and caught his eye. Naturally, he came over, and we started dancing together. Upon closer inspection, he was even cuter than I expected, and he could move. After several dances , kisses and making out awhile he suggested we head to his room. I played coy and declined with a wink..."for now". What goes on spring break may stay on spring break, but I was at least going to force Jack to make a second move.

Kira, the drama queen in our group and one of my closest friends, ruined my plans with a episode that we would talk about for years. I groaned and kissed Jack a quick goodbye before leaving to take care of Kira. By the time the six of us had calmed her down, the night was shot. No harm done, just another over reaction, but that's what friends are for.

The next morning I was ticked that my Jack had gotten away. I got way too soused and spent too much time under the sun. Thank god for SPF 30—no sunburn. I crashed early in the afternoon and laid in bed in a foul mood, munching on pizza as the rest of the group got made up and headed out for another night out. I was pissed and couldn't seem to get up the will to go out again.

Nine pm turned to eleven pm, and the reality that I was on spring break and I had to enjoy myself sank in. I got up and forced myself to get ready and go out. I went to the club that my friends had gone to and was in such a bad mood I immediately bought myself a drink. I was not up for another night of the games, especially after losing such a prize.

I started through the crowd looking for my friends when I saw him...my Jack, against the wall. My heart flipped, and to my delight, he smiled broadly when he saw me. Determined not to lose him again, I walked right up to him and kissed my apology. He responded as passionately as last night, as if we had never parted. We started dancing and I was immediately in a wonderfully playful mood. I saw his eyes move from mine in a way they shouldn't and he smiled as another girl moved up to us. She was gorgeous and smiled lasciviously at me before planting a full tongue kiss on him. I was stunned at the turn of events.

"Sarah, this is Lisa," he said to me before turning to her. "I met her last night."

Lisa nodded and leaned over to me. "Well, he has good taste," she said with a confident smirk as she entwined her hand with his. "Nice meeting you, but we were just leaving."

I could feel my blood begin to boil, and I reached out for his hand. He was so smooth as he took my hand and asked if I wanted to join them. There was no way I was going to say no. She may be prettier than I, but I was going not going to let him go again. I relished the surprise on her face as I assented with a full tongue kiss. We slipped out the door, Jack holding each of our hands, and hailed a cab. I must say, Jack did an admirable job of both managing me and keeping Lisa and me separated but involved.

We got in the cab with Jack between us. He leaned over and kissed me, and I responded, inviting his hands to explore. Instead, he broke our kiss and turned his attention to Lisa. I could hear her mew softly as I waited for my turn. He attended to her for a few blocks, and I decided to up the ante, sliding my hand up his thigh to give his swelling member a light squeeze. He responded immediately, breaking from Lisa and kissing me while casually cupping my breast. I moaned my appreciation to both Jack and Lisa. To soon, the taxi pulled up to the hotel and we piled out. We entered the elevator with his arms around each of our waists. It occurred to me that this was every man's fantasy, but I had my needs too. I wanted him to understand that I would fulfill his every need, and he should send Lisa home. How naïve of me.

We entered his room, and I was impressed. What a place! It appeared to be a luxury room with an ocean view balcony. Jack excused himself to the restroom. I tried to appear casual, strolling around to admire the view.

Lisa opened the fridge and offered me a cooler. I accepted and got a good look at her. She was beautiful. She seemed at least 6" taller than me and had jet black hair and a cup size or two on my Bs. What was I doing? I wouldn't even have sex with the lights on. This was so out of my league. My nerve left me.

"You OK?" she asked patronizingly. Or maybe she was showing with genuine concern. I was too rattled to tell.

I nodded with the best look of confidence I could summon and took a big swig. Jack emerged with a smile and grabbed a beer. I seized the moment and excused myself to the bathroom, where I tried to compose myself. I touched up my makeup as I tried to give myself a pep talk. I wished I had brought my drink with me.

I emerged to see Jack and Lisa in a passionate embrace in the middle of the room. I stood by my drink, unsure of what to do, until Jack broke off the kiss and wrapped his arm around my waist, pulling me to them. I kissed him with abandon. Jack had a firm grip on my ass, and I could hear Lisa kissing his neck. Our hands brushed against each other other's as we stroked his chest. Jack broke our kiss and started on Lisa. I panted as I watched them go at it. I started kissing his neck and inhaling that man smell, only this time mingled with a more delicate perfume. My fingers fumbled with the buttons on his shirt as he switched back to me. Between the two of us we got his shirt open as he continued to alternate kisses while kneading my ass. His chest was smooth and firm and wonderful. He broke from Lisa and paused.

"Kiss her," he growled.

Lisa tossed her hair back and cupped my cheek as she leaned in. I pulled back. Jack and Lisa looked at me, surprised.

"I...uh...never kissed a girl."

I saw that look in Lisa's eye, that look that girls give the only virgin in the room.

"Really?" Jack said with a smirk. "Well, we wouldn't want to do anything to make you uncomfortable."

He kissed me again, releasing my ass and shucking his shirt. Standing between us, he freely groped me as we kissed, then turned to do the same to Lisa. I kissed his shoulders and caressed his back as I listened to them make out. He pulled away from Lisa and stepped out from between us. He slid behind me and placed his chin on my shoulder, both of us facing Lisa. She had kicked off her heels, and we were now the same height.

I could feel Jack's hot breath on my neck as he stroked down my arms and raised my hands by the wrists to Lisa's blouse. My hands hung limply, as I was unsure what to do. He brushed her breast with the back of my hand before guiding my hands to the top button. Holding me there, I slowly undid the top button. Lisa reached out and placed her hands on my hips and Jack lowered my hands to the next button. Four buttons were all it took and Jack moved my hand to push the blouse just off her shoulders. She was wearing a sexy white lace bra, and Jack murmured in appreciation. He again guided my hands to lightly stroke her breasts, and she smiled wickedly at us. Jack then moved from behind me to stand behind her, fully removing her blouse. Lisa knew what he wanted and lifted my top on her own as Jack watched and stroked her skin. I didn't know what to do, who to look at or where to put my hands. Lisa smiled at me again and slowly cupped my breast. I let out a little squeak, tearing my eyes from Jack and seeing the lust in her eyes. She ran a fingernail up my arm and shoulder and then across my décolletage. I trembled with anticipation.

I saw Jack move his hands behind her, and as she turned to kiss him the tension in her bra was released. I could see it just hanging off her shoulders as they kissed, her fingers stroking my skin. Jack reached over and grabbed one of my wrists, raising it to the loose bra strap. My other hand raised in sympathy as if it had a mind of it's own. I slowly pulled it off of her, dropping it absently as I lowered my gaze to her breasts. She reached up with one hand and placed it on Jack's head as they kissed, caressing my side with her other hand. As if in a trance, I started touching her skin, carefully avoiding her breasts.

Jack finally broke the kiss and slid over behind me. Lisa stroked my sides and played with my hands as she watched me. I leaned back and kissed Jack as he undid my bra. I was wearing a strapless bra, so it fell to the floor as soon as it was released. I squealed as I felt Lisa's fingers rubbing my nipples, and I leaned heavily on Jack. I didn't know how to react, but my nipples were singing. Jack broke our kiss and looked at Lisa and cupped my tits for her. I panted and held Lisa's elbows for balance as 4 hands roamed my breasts. I was mesmerized by the lust in Lisa's eyes as they switched between me and Jack. Jack nudged me onto my own feet and moved away, leaving me and Lisa face to face. She was absolutely gorgeous. Her hands were moving across my body, stroking my side, caressing a breast, tracing a shoulder. My hands started to roam her body. I tentatively caressed her breast, averting my eyes in embarrassment.

"So," she said, "Have you ever been in a threesome?"

I shook my head. "No."

"Not even with two guys?"

I smiled back at her, "No."

She grinned at me mischievously, raising an eyebrow as she tweaked my nipple. "Ever had anal sex?"

"No," I squeaked.

Her eyes darted to Jack and winked.

"Well, that's a shame."

I lost track of Jack for awhile, absorbed by Lisa's beautiful face as we touched each other. I was vaguely aware of him moving the background, removing my skirt, and I noticed Lisa's was already off. Lisa feigned coming in for a kiss, and I leaned in for it, but she pulled away. She repeated her tease several times, until all I wanted was to kiss her. Jack slid off my panties and I stepped out of them. I watched Lisa's eyes drift down and felt the heat rise in my cheeks from embarrassment. Jack licked the back of my thigh and nipped my bottom. He moved in behind Lisa and slipped off her panties. I tried but couldn't resist looking down at her pussy. It was shaved bare and I had to rip my eyes away. Lisa cupped my face to bring my eyes back to her and licked her lips.

Jack appeared next to us, and we both attacked him. His skin seemed so different, so right, yet I wanted to touch Lisa also. My hands roamed his chest, and Lisa ripped off his belt and undid his pants. He was quickly out of them, and our hands found him fully erect. Breaking my kiss, he turned to kiss Lisa. He pushed me down with one hand as I dropped to my knees to take him in, filling my mouth completely. Through my slitted eyes I realized I was staring right at Lisa's bare pussy. I could feel my eyes widen. As I could hear Jack and Lisa engrossed in their kisses, I felt as if somehow it was OK to look if she didn't know. I had never seen another girl up close like that and I couldn't look away even as my tongue worked up and down Jack's magnificent hardness.

Suddenly his hand was pulling me up by my hair and I rose. Lisa dropped down to take my place, and he started kissing me. His hand began mauling my breast as we kissed, but I could almost feel Lisa's eyes on my bush. I held on to Jack and felt Lisa's delicate touch on my knee, opening me up more for her. My head was swimming. I felt her finger drift up my thigh. I knew it was wrong, but I wanted her to touch me...there. Instead, she drifted her hand across my belly before settling on my hip. My hand left Jack's chest and fell to her head, finding her bobbing up and down on his dick.

Jack pushed me down again and positioned his cock between us. Lisa began licking up and down his dick and I started doing the same from the other side. I was nose to nose with a girl I wanted desperately to kiss, separated by a cock. Her hands found my tits and I found hers, feeling somehow safer that I couldn't see what I was doing. I cupped her soft, full breasts and rolled her nipples. Sometimes our tongues would touch underneath his cock, sending shockwaves through me. She teased me again and again, pressing her hand flat against my belly and slowly sliding down to my cunt, pulling away at the last moment. I was quivering in arousal.

She moved to take his dick into her mouth and I ran my tongue across part of her lips. After a few moments, she moved back to the side and I took him into my mouth. Her tongue danced along my lips and I moaned.

I don't know how long we went on, but Jack started groaning and pulled Lisa onto his dick. He held both of us by our hair and I could feet the cum shooting through the base of his dick and into her mouth with the tip of my tongue. Finally his spasms subsided and he pulled away, leaving Lisa with a mouthful of cum. She opened wide to show him and saw that I was looking also. She closed her mouth with a smile and I though she was going to swallow. Instead, she leaned forward and planted a kiss on me, full tongue. Now, I rarely swallow, but I wanted that kiss so badly I dove in. My first girl-girl kiss shared with a load of cum. I was so turned on I didn't care.

We kissed and kissed, collapsing on the floor. I don't know how much I swallowed, but soon it was just me and her on the ground kissing and touching. Some cum had dribbled out but we licked all up. Jack surprised me when he touched us again, I was so into Lisa I had almost forgotten about him. He opened up my thighs and I squealed as he inserted a finger into me. Lisa did the same moments later. After being finger-fucked for a few moments, he pulled out and inserted his thumb instead. I thought nothing of it until I felt his finger, slick with my juices, pressing against my asshole. I broke my kiss with Lisa in alarm, but she held me tightly.

"Its OK, let him six-pack you."

I relaxed reluctantly as I let his finger slip into me. Lisa let out a little moan moments later and soon I was lost in her kiss again. It felt weird to have something wiggling in my ass, but between Lisa's tongue and hands and his thumb working my cunt I really didn't care. I was getting close.

Lisa beat me to it.

Lisa came, hard, in my arms. I was seconds away from joining her when Jack pulled out and went to the rest room to clean up. I was left kissing Lisa. We kissed and kissed and kissed, finding our way to the bed. I finally became aware of Jack near us as I felt his hardness between my thighs. I eagerly opened up to allow him access.

"Fuck her in the ass," Lisa growled, eyes blazing.

Jack paused behind me, mere inches from my cunt as I shook my head.

"No fucking way is that going to fit in there!" I protested. Jack was not small.

"It'll be fine, trust me," Lisa smiled with a kiss, and then proceeded to kiss away any further protests from me.

Now, a few lovers had asked to fuck me in the ass and I had declined, but between my aroused state and Lisa's encouragement, I collapsed. How could anyone refuse Lisa what she wanted?

"Ok," I reluctantly agreed. Lisa flashed a smile at Jack.

Lisa positioned me on my knees, ass in the air. She maneuvered herself beside my ass and held me open for him, applying some petroleum jelly to my anus and his cock. As I felt the tip of his cock begin to penetrate me, I tensed up and tried to fight it. My lubricated asshole proved incapable of stopping him and he forced his way in. It hurt like hell. Lisa held my hand a lay beside me and stroked my hair as Jack took my anal virginity. I could feel Jack's torso press against my ass as he bottomed out on me.

"Holy shit she's tight," he groaned, gripping my hips firmly and slamming hard into me.

The sensation was really weird, painful but not unbearable. Lisa kissed away my groans.

"Are you OK?" she asked and I grunted in agreement.

"Lets flip her over," she said to Jack.

Before I knew it, Jack had wrapped a strong arm around my waist and was rolling over onto his back. I found myself straddling crab-like over him, hands beside his shoulders, heels beside his hips, impaled on his cock. Totally open, totally vulnerable. His hands began to roam my body as I tried desperately to hold him still inside of me. Lisa crouched beside us, kissing, touching and licking me. I jerked when she sucked a nipple into her mouth, forcing me to shift on the invader in my ass.

"You like that, don't you," she growled.

I couldn't bring myself to admit it, so I just screamed "Fuck!". She continued to suck on my nipple as Jack worked the other one. I couldn't take my eyes off of her. Occasionally Jack would thrust in and out of my a few times causing me to squeal. Lisa pulled back and my nipple came free with an audible pop.

"Lets see how you're doing down here," she purred as she repositioned herself between our thighs.

I stared wide-eyed as she nipped and kissed my inner thighs and then slowly opened up my lips with her fingers.

"Pretty wet, aren't you?" she smiled, inches from my clit.

I couldn't do anything to stop her, I was completely helpless. It just seemed so wrong...she was girl! But it felt so right. My arms started to quiver from fatigue. She feigned like she was going in to lick me and I tensed in anticipation, but she pulled off and licked my thigh. She patted my open pussy with her hand, sending shockwaves through me.

"You want me to eat you, don't you?" she demanded.

"No," I replied through gritted teeth.

She patted my pussy again and asked.

"Say you want me to eat your pussy."

I could only shake my head as she positioned her mouth at my cunt. I could feel her breath on my clit and I panted in anticipation.

"Say it!" she demanded.

I surrendered.

"Eat me! Eat my pussy!"

"I think she's ready!" she beamed, pulling away. "Put her on her knees."

Jack wrapped a powerful arm around my waist again and he slid us off the bed and flipped over. I was now on my knees with my face planted on the edge of the bed as he stood over me. Jack gripped my hips and started to hammer into my ass. I couldn't believe how powerful his thrust were—I was completely at his mercy. Lisa moved behind us and forced my legs apart. She slid in between my thighs and immediately started to lick me. A girl! It was so wrong, more gentle and yet more intense than anything I had ever felt. Despite the pain in my asshole I started to cum. Jack picked up the pace of his thrusts as the wave of my orgasm kept building. I screamed into the bed, gripping the sheets as my world shook with the most powerful orgasm I had ever had. It went on and on as Lisa licked me and Jack fucked me. Finally, mercifully, my spasms subsided and Lisa pulled away. Moments later Jack started to groan as he pounded my limp body. I felt him spurt into my ass and more stars clouded my brain. Lisa appeared beside me and held me as Jack collapsed on top of me. I could feel Jack and Lisa kissing as he grew soft inside of me. He pulled out and headed to the bathroom as I tried to catch my breath. Lisa kissed my cheek and then inspected my ass.

"Nothing torn, you're good," she cheerfully reported.

I nodded numbly as she helped me onto the bed, holding me as I came back down to earth. Jack reappeared and settled between us with a kiss.

"You OK?" he asked.

"Yeah," I nodded numbly, "that was intense."