Spring Break Ch. 01

Story Info
A spring break trip for a group of friends "with benefits".
10.9k words
4.78
483.6k
287

Part 1 of the 7 part series

Updated 10/29/2022
Created 12/14/2005
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HLD
HLD
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Prologue

The only thing better than having a friend "with benefits" is having two friends "with benefits."

When I was in college we used to go to Orlando every year for spring break. It was only about two hours away and my folks were members of a timeshare club, so we often stayed in a nice condo for free and got tickets to Disney World, Universal Studios and Sea World for cheap.

My junior year I was kind of seeing Melinda, a girl I had met my freshman year. She was a year ahead of me and if not for our different schedules, we probably would have had a much more serious relationship. As it was, her classes were in the morning and then she worked during the day. Most of my classes were in the afternoon and then I worked evenings and weekends. We did manage to find times for romantic trysts, but these were never as often as we'd have liked, and saw other people as well.

I also kept in touch with Leah, a friend I had known since middle school. Although she went to school in North Carolina, we emailed back and forth a lot and visited each other a couple of times. It was on one of those trips that we hooked up, and although neither of us wanted a long-distance relationship, we remained friends and sometimes lovers.

That spring break, six of us were planning to go to Orlando. My folks let me use some of their timeshare points on a two bedroom condo at Disney's Old Key West Resort. The brochure said it slept eight, so I knew there would be enough privacy for everyone to get their groove on.

In addition to Melinda and I, Leah was flying down with her boyfriend, and two of my other friends were also going with us. I met Katie in one of my classes and Carl was her high school sweetheart. Melinda and I had gone on a couple of double dates with them and I knew Leah and Darren would get along with everyone.

Two days before the trip, Melinda and I had found some time to be together and were watching TV when the phone rang.

"Hello?" Melinda picked it up. "Yes, he's right here. Are you okay? . . . He did what?!?! . . . That's terrible . . . What a bastard . . . No. . . . No. . . . No! . . . That's crazy, you're coming down anyway. . . . I've been looking forward to meeting you for too long. . . . Pack your bags and get down here . . . No. . . . That won't be a problem. . . . Here let me let you talk to him."

She covered the mouthpiece on the phone and whispered to me. "Leah and Darren just broke up. She's trying to back out. Make her come on the trip."

I took the receiver and began some long-distance boyfriend therapy. Leah said she didn't want to be a fifth wheel, but she was also just feeling sorry for herself, and after some poking and prodding admitted she didn't want to be by herself for the next few days, especially since we had been planning this trip for several months. After about 20 minutes of me trying to convince her to come down and letting us find a spring break fling for her, Melinda took over again and engaged her in some good, old-fashioned male-bashing. It seemed to brighten her up because an hour later, Leah was laughing and ready to come visit for spring break. Melinda made Leah promise to be on the plane on Sunday and hung up.

Melinda curled up next to me on the couch.

"Thanks," I said.

"For what?"

I brushed the strawberry blonde hair out of her eyes. "For getting Leah to come down even without her boyfriend."

"She needs a friend right now and you're one of the best friends she has."

"You didn't have to, and I appreciate that." I paused for a long second. "I just don't want things getting weird on us . . ."

"Well, mister, we'll see about that," she smiled mischievously, and ran her hand up my thigh. I hadn't noticed before, but somehow her blouse had become unbuttoned and her big, round breasts were spilling out for me to see. She kissed me and then bit my lip. "And if you play your cards right, you may get that fantasy you have to come true . . . "

The sex for the next couple of days was especially hot.

************************

Sunday

Melinda, Katie, Carl and I picked up Leah at the airport on Sunday morning. She got an early flight in, and with the two hour drive to Orlando, we would get to the condo right about check-in time.

I waved to Leah as soon as she got off the plane. She ran over and gave me a big hug. I held her tight and gave her a friendly kiss. Melinda watched along with Katie and Carl. Even though she had talked Leah into coming down and had spoken to her before, I knew Melinda could be mean and spiteful with some of the other girls I had been seeing. To be fair, I wasn't exactly nice to some of the guys she went out with either. I hoped she would be good to Leah.

We walked back to my other friends and I introduced everyone. Katie and Carl were friendly and to mine and Leah's surprise, Melinda gave her a warm hug. We went to the baggage claim area, making small talk and saying not-so-nice things about Darren.

Soon enough, we were in the car. Katie's folks were letting us take their minivan. Sure a Dodge Caravan wassooooooooo not the kind of car a bunch of college kids want to be taking on spring break, but it was a hell of a lot more spacious than my beat up old Honda Prelude or Melinda's Toyota pickup truck.

Carl was driving and Katie was in the passenger's seat. Leah and Melinda sat in the second row captain's chairs and I occupied the back seat along with a cooler and the snacks. The drive down was leisurely and Leah seemed to hit it off with everyone.

Melinda, Leah and Katie were all smart and pretty. Leah was brunette and a former lacrosse player; Melinda was strawberry blonde and played softball. Each thought they were overweight, but I thought they were both just the right size. I like my women built for comfort, not speed. Katie was easily the smallest of the girls; petite, with fiery red hair and a temper to match.

We got to Orlando and drove to the Old Key West Resort. I presented my parents's timeshare club card at the front desk, signed a paper stating that everyone staying in the room was over 21 (not true, but what was one little lie?) and picked up our room keys and park passes.

Carl parked the van and we unloaded all our stuff into the room. There was a master suite with an enormous bed, a stand up shower large enough to accommodate all six of us, and a jacuzzi tub. The other bedroom had two double beds and a private bath. In the middle was a small kitchen with a range, oven and microwave that also had a foldout couch. There was even a full-size washer and dryer hidden in one of the closets.

Included in the timeshare were tickets to all the Disney theme parks, water parks and other attractions for the duration of our stay and free run of the ingenious transportation system. After unloading all our bags and the few groceries we brought, we had to come up with sleeping arrangements.

Melinda and I got the master suite (they were my parents's timeshare points, after all) and Katie and Carl moved into the other bedroom. Leah looked awkward when she rolled her suitcase in the front door.

"Put your stuff in the big closet in our room," Melinda told her.

"I don't want to be in your space," Leah said.

"It's better there than all over the living room." I thought I saw Melinda wink at me.

Leah looked at me quizzically; I just shrugged.

We got everything put up and decided it was time to go get something to eat. This was the first time Katie, Carl and Leah had ever been to Disney World. We went out to the front of the Old Key West Resort and got on a pontoon water launch that took us to Buena Vista Village and Pleasure Island. Everyone liked seafood, so the consensus was to go to Fulton's Crab House, which is a restaurant built to look like a paddle-wheel steam ship.

The food was excellent (as always) and drinks helped loosen everyone up. Leah was feeling a little more upbeat and the rest of us were enjoying a warm spring evening. After dinner, we did some shopping at Disney Village and then walked over to Pleasure Island, a conglomeration of themed nightclubs and retail shops.

I noticed that several times Melinda and Leah ended up walking and talking together, probably about Darren and doing some girl-bonding.

After a couple of hours of dancing and what was probably a few drinks too many, we all headed back to the room, made plans to get up for breakfast and then went to sleep off all the liquor.

Katie and Carl disappeared into the second bedroom. I didn't think they were going to make it fully clothed back to the room, but somehow they did. Katie is an affectionate drunk and Carl was a hormone-driven 19 year old boy. It's a good thing the only other hotel guests on the pontoon boat were Melinda, Leah and I. The boat driver got a good show, though.

"I'm guessing you guys are going to stay up and talk. I'm going to bed." Melinda gave me a good-night kiss and hugged Leah before retreating into the master bedroom. That left the two of us sitting on the couch.

I had my arm around Leah and we talked like the old friends we were. She was depressed about breaking up with Darren, but they were never that serious to begin with. It was probably midnight when we got back, but 2 am when I finally went to bed.

Leah didn't want the couch pulled out, so I got her a pillow, a sheet and a blanket. She lay down, a long day of traveling finally catching up with her. I leaned over and kissed her.

"Thanks for making me come on this trip," she said, wrapping her arms around my neck. Our foreheads touched and we brushed our noses together in an eskimo kiss.

"We've been looking forward to this for too long to let Darren spoil it for us," I smiled. I really was glad to see my friend again, even if things were a little weird with myotherfriend along with us.

She kissed me again and then let go, a devilish smile on her face. "Now go to bed before I jump you and get Melinda all pissed off at me."

I gave her a not-so-fatherly swat across the backside and then got up and went to bed.

Melinda was asleep when I crawled into bed. I didn't bother to find my nightshirt; I just stripped down to my boxers and slipped under the sheets. Melinda was lying on her side facing away from me. I spooned up next to her and put my arm around her.

"How's Leah?" she asked sleepily.

"She'll be fine," I whispered. "She just needs to get her mind of Darren."

"Good." Melinda rolled over on to her back. Moonlight shone through the windows. I could make out her silhouette in the darkness. I could tell she was naked under the sheets. Her heavy breasts had fallen to the sides, their nipples pointing straight up. "She's lucky to have you as her friend."

"I was worried about her coming with us this week. I know she feels a little funny about being with us all by herself," I said quietly. "And I know how you get around some of the girls I've been seeing."

"And how's that?" Melinda said with mock indignation.

"Catty, hateful," I replied.

"I'm only like that around the girls who don't deserve you."

"So you don't think any of the girls I've gone out with deserve me?"

"Of course not." She snorted softly. "But don't worry about me this week. I can't be jealous of Leah; she's known you longer and I know you're not after her just for the sex. I also happen to know that if the two of you had ended up going to the same school, I wouldn't have had a chance with you. Besides, she's cute, too."

I cradled my lover in my arms. "Well, I want you to know how much I appreciate you being nice and friendly to Leah. It means a lot to me and I know it means a lot to her, too. So thank you."

"Are we done talking?" Melinda giggled and then reached for me. "Because I'm tired, but I'd really like for my pussy to get eaten and then fucked before I go to sleep."

************************

Monday

I woke up spooning with my lover, one arm under the pillows, the other around her, a breast in my hand.

Even though I was still a little groggy, I knew it wasn't one of the breasts I had gone to sleep holding.

Leah turned her head and smiled. "Good morning, sleepyhead."

"Where—?" I lifted my head, looking for my other lover.

"In the shower."

"What time is it?" I dropped my head back on to the pillow.

"Almost nine."

"What are you doing here?" I hadn't let go of Leah's covered breast.

"I got tired of listening to Katie and Carl on the other side of the wall," Leah snickered. "You'd think that for what Disney charges to stay here, they could have installed some decent soundproofing. You and Melinda were much quieter last night."

I grinned sheepishly.

"She got up to make coffee before her morning walk and told me to come in here with you." Leah smiled nervously. "I didn't want to push my luck with her and take advantage of you, but it was really nice to have someone holding me. Even if you didn't notice that it was me in bed with you."

Melinda shut the shower off. From the massive bed, we could see her silhouette across the master suite on the other side of the jacuzzi tub. The bottom half of the shower wall was tile, but from about waist-high to the ceiling was textured glass that only showed silhouettes of what was on the other side. Even though distorted, her curves were evident. My cock unconsciously twitched.

"I see you're still a morning guy," Leah teased. I playfully pinched her nipple through her nightshirt. She slapped at my hand.

We watched Melinda dry off through the glass. I squeezed Leah's breast again, this time not so playfully. Leah reached around and her hand strayed down to my cock, which was pressed against her ass. She wasn't wearing any shorts or panties.

Melinda came out of the shower. She had one towel held up by her breasts, her hair wrapped in another. She looked at us with a slightly amused expression on her face.

"Good morning, you two." Melinda crawled into the big bed next to us. Leah was in the middle. We were still spooning. I had my hand on her breast and her hand was wrapped around my stiff prick. "What's the plan this morning?"

"I'm thinking of getting a shower and going out for breakfast," I said as Leah rubbed my cock between the cheeks of her ass. Melinda had to know what we were doing. "And then I guess we're going over to the Magic Kingdom."

Melinda leaned over Leah and surprised her with a quick kiss. Leah tensed, then returned the affection. I was mesmerised. Melinda then reached across to me, pressing her full, towel-covered breasts against us both. She gave me a deeper kiss then her lips brushed my ear.

My jaw dropped when she said quietly to me, "Fuck her good."

I started at Melinda in disbelief as she went to get up. "I'm going to see what the horndogs are up to and tell them that we're leaving in an hour."

Melinda whispered something to Leah then kissed us both again. The three of us stumbled out of the bed. Melinda had thrown my boxers across the room sometime in the middle of the night, so I didn't bother to dress. After all, I didn't have anything the two girls hadn't seen before.

Leah was wearing a long t-shirt and we headed off to the shower. I slapped her across the backside and looked back at Melinda. She stood in the doorway, smiled mischievously then opened her towel up to flash me for an instant, revealing all her voluptuous curves and a freshly-shaved pussy.

She blew me a kiss, covered up and then disappeared into the hallway.

Leah had already started the water running. There were two shower heads and the water was warm and refreshing. We stood there under the warm water for a few minutes, then broke out the shampoo and soap. She washed me first, quickly but playfully.

Once I was clean, I lathered up Leah's hair, something I knew she liked. After rinsing out the shampoo, I began to wash her body, cleaning everything that needed to be cleaned and lingering unnecessarily on the sensitive spots.

She moaned slightly when my hands covered her breasts, slippery from the soap. Her nipples hardened instantly. I pinched them and she moaned a little louder.

My hands roamed a little lower. She spread her legs in anticipation. I ran my fingers over her neatly trimmed bush. Her labia were swollen and slick not only from the shower water but my fingers working her over.

I slipped one finger inside her. Then two. She moaned and leaned back against the cool glass wall as the hot shower water cascaded over us.

Her hand went to my cock. It became longer with every pull.

My hand moved faster, my fingers stimulating the inside and my palm rubbing against Leah's clit.

Her hips started to buck as I sped up my rhythm. Her breathing became shorter. Ragged.

We kissed again and she bit my tongue softly. My free hand cupped one of her breasts.

Leah let out a soft moan and I felt her shudder.

"Please put it inside me," she whispered in my ear.

All too willingly I pressed against her. She guided the head of my cock into the soft folds of her pussy. "Oh, god . . . that feels so good."

The water continued to flow over us. We kissed again. I pressed my chest against her. She dug her nails into my shoulders as my cock sank all the way inside. I began to gyrate my hips, building a steady rhythm.

With every stroke Leah let out a soft moan. Her moans became louder as we made love.

She began to grind her hips so that her clit rubbed against the top of my shaft.

Pressing deep inside her, I let go of her breasts and took her hands from my shoulders. I pinned them above her head and she ground her hips harder against me.

I held her wrists with one hand, and reached for her left breast with the other. I began to knead her tit in my palm, then pinched her nipple. She tried to pull her arms down, but I wouldn't let go.

My mouth strayed to her neck and she cried out.

Our gyrations became faster. Our breathing quickened.

She tried again to break her arms free of my grasp, but I held firm. I felt the head of my cock begin to pulse. I was close. I bit down on my lip, trying hold on for a few moments longer.

"Oh, yes!" Leah whispered, her voice breaking. "Come inside me . . . please . . ."

I gave her a final hard thrust and we both climaxed. Our lips met again and I emptied my balls into her pussy. I could feel Leah's sex contracting from her own orgasm.

She wrapped her arms around me as I released her. I slumped against her, spent.

We stood like that for a long moment, the warm water carrying the sweat off our bodies. Holding each other tight, we savoured each other's touch.

I listened to her breathing as we slowly recovered. Finally my softening cock slipped out of her and I pulled back. Leah had a satisfied look on her face. The water continued to flow over her beautiful nude body.

"Thank you," she said, her eyes fluttering open. We kissed again.

After rinsing off again, I turned the water off and opened the door to the shower. We got a couple of towels and began drying off.

I stepped out of the shower and stopped dead in my tracks. Leah bumped into me, then she stopped, too, her eyes wide.

Melinda was splayed out on the bed, her naked body facing us. There was a wicked glint in her eyes.

Her legs were spread and hung off the bed. She was laying back, her head still wrapped in a towel and propped up on a pillow.

She was cupping a breast with one hand while the other played between her legs.

"That was very hot," Melinda said quietly. "Now come here, you two. It's my turn."

I stared, dumfounded.

Leah pushed me forward until we were both standing by the bed.

Melinda and my eyes locked. She smiled, then pointed at my crotch. "Lose the towels."

Leah's towel dropped to the floor, then she reached for mine and kicked it back towards the shower.

Still looking me in the eyes, Melinda asked, "Leah, is he hard?"

HLD
HLD
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