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?"
