Vacation with Family Friends Ch. 01

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A guy loses his virginity and becomes a bull in one trip.
12.1k words
4.63
41.7k
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Part 1 of the 2 part series

Updated 06/10/2023
Created 06/23/2021
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Justin couldn't quite pinpoint the moment it happened, but at some point during dinner he had come to the realization that he owed his mother an apology. When she had talked him into joining his parents on vacation during his first summer after starting college, he had been reluctant to accept. He had planned to try to find work and stay on campus, but his mother had really poured on the guilt, "Justin please, you have your whole life to live on campus, and it's been so hard for us being apart from you this year. Your father and I know that you will love this trip as much as we will, and it is only a week. We are paying for everything and, trust me, that won't be happening forever, so I really recommend you take this chance."

He couldn't refuse that, but the regret had begun immediately afterwords as only then did his mom inform him that the trip would be with their family friends, the Johnson's. Now, Justin didn't have anything against the Johnson's, having been their neighbors for most of his childhood up until high school, but the older he'd gotten the more distant he'd felt from them. Particularly from their daughter, Alice.

As close as they'd been as kids, playing together daily, that friendship didn't survive the rigors of growing up. Justin hadn't been unpopular at school, but in the hierarchical social system that makes up public schooling, it was clear that he and Alice were different levels. He'd been into math and track, while she'd been a football jock-dating party girl cheerleader. Even though they went to different high schools, it was always evident that they wouldn't have been in the same group even if they had. It's not that she was rude or stuck-up, but it was always clear that after the group family activities were done that there was no way the two of them were going to be hanging out together alone. He found her to be a bit ditzy, and goodness knows what she thought of him. What was clear was that neither one tried very hard to develop a relationship with the other despite the closeness of their families.

So, the idea of being around her for a week had been an anchor on Justin's neck for the weeks leading up to the trip. But all the awkwardness that Justin had been dreading seemed like a waste of emotional energy from the moment that he and his parents were greeted by the waiting Johnson's at dinner that first night. Mr. and Mrs. Johnson were charming as ever, and both grabbed Justin in a group bear hug that had him laughing by the time they let him get his breath. He found himself grinning them back as well as they asked him how he was doing at school. Alice also had surprised him with a warm hug, and things never went downhill from there.

The conversation with the elder Johnson's had been mirrored by Alice and his parents, and the two of them kept catching each others eyes and laughing at how happy they were to be in each others parent's company once again. That affection overwhelmed any high school hangups they might have had towards one an other, and before long they were speaking just as enthusiastically with one another. He found that she had stopped cheerleading as she found it too serious at the collegiate level, and was instead focusing on her studies and her boyfriend. Justin was surprised to find himself bummed by the realization that she was dating, but it didn't last long as she enthusiastically asked him about his college experience. No girlfriend for him yet, as he was concentrating on track and field. His coach had told him that if he kept improving his times, there was a more than good chance that he could earn a scholarship next year.

Wine and spirits helped the conversation flow, and the whole table was actually disappointed when the waiter informed them that the restaurant was closing. As it was the first night, no one wanted to go too crazy anyway, and after another round of hugs, Mr. and Mrs. Johnson withdrew up to their executive suit, while Alice and Justin followed his already exuberant parents to the 4th floor where they all had their suites.

"Goodnight you two! We'll see you bright and early for breakfast, 8am!" mom said, too loudly to us down the hall, as my dad fiddled with the room key. He looked up with looking way too pleased with himself for having finally managed to time the turning of the handle with the mechanism's unlock, and added, "I know that's early for vacation, but don't make us wait. We're old and cranky." Mom slapped him playfully on the back, "Maybe YOU'RE old" to which he responded, "And you're cranky. What a team." He grabbed her by the lower back and pulled her to him as he walked backwards into the room. "Love you buddy, I'm so glad you could make it. Alice, I hope he doesn't snore."

"If he's anything like his father he will darling" my mom said, laughing and stumbling tipsily against my dad. "Make him sleep in the bathtub if the beds are too close together." The last thing I saw was my dad's hand on her ass as he pulled her inside and the door slammed behind him.

I wasn't super pleased about a number of realities of my room situation, my proximity to my parents being only one of them. The other, I had thought, was that I'd be sharing with Alice. Though after that first dinner with the two families, I was a bit less bothered by that part. If anything, was feeling a bit bad that I never gave her a chance when we were growing up.

Speaking of Alice, she had managed to get our door open on her first try, and I saw that she was smiling broadly at my parent's antics. Not bad for a ditz. She swung the door wide, and walked in, saying to me over her shoulder, "It's so great to see your parents against Alex. They are so amazing and your dad is definitely going to get lucky tonight," with a cheerful laugh.

"Oh shut up," I said and laughed with her. I was equally proud and grossed out by the fact that my parents seem to have managed to keep up an active sex life for their 25 year marriage. I had heard from enough friends at college that that seemed to be the exception rather than the rule. Still, it wasn't something that I wanted to talk about. "You're just happy that your parents are on a different floor."

"Their executive membership points have their privileges," she said and then stopped as she surveyed our accommodation for the first time. "For them at least. Is this really it?" Her hand was outstretched to the single room beyond the entryway. I looked past her half smiling face to take in our accommodation for the next week.

A five start resort, everything I could see was top class. Floor to ceiling windows lined the back of the room, with a terrace and a view of the pool beyond. Amazing. A large flat screen mounted on the wall, a desk and char next to it. A bathroom to our left, which looked to be modernly appointed with a large shower/tub combo. Only a single sink, I noticed, and a bit smaller than I had been imagining. I walked in further and saw that there was a couch along the shared bathroom/bedroom wall with a coffee table and a side table that almost certainly housed a minibar/fridge. And a King size bed. A nicely adorned, comfy looking, heavily pillowed, very large, but definitely only one, bed. And no second room.

"Didn't they say we would have two rooms?" I said, "I clearly remember them saying two rooms."

"Yes, they did say that." Alice responded, her tone losing most of the luster it had held only moments before. "What the hell, that is one room." She looked at me, her hand still outstretched. "That is not two rooms."

"Clearly, we can both count to two, and while counting rooms, we both stopped at one. So unless we are drunker than we should be after that single glass of bubbles, I think we can close the conversation about there being only one room." I responded, trying to make light of the situation and buy some time to figure out what to do next.

It seemed to work, as Alice's full smile returned and she beamed at me. "At least it's nice though, right? Much better than my dorm anyway. Good thing there's a couch" she said, and we both turned to look at it. She went over to it and bent over to investigate. "I guess it must be a pullout?"

"Umm.." I said, distracted by the view of her from behind, and her behind, as she lifted a cushion. Her ass was everything I remembered, and more, from the high school days. She had filled out in the last year, and only in the best possible way. She was wearing a silky green flower patterned pant suit? Onsie? Some fancy pant dress summery thing with two legs and held up by two straps. The neck was loose and with way more fabric that seemed to reshape itself whenever she moved. I'd been fascinated by it all night.

Bending over was a new movement, however, and I was happy to see that it reshaped itself in a way that it stretched tight against a clearly ample behind, two hemispheres round, plump and distracting. I didn't detect any panty lines. I shook my head and continued, "I don't know if they'd put such a heavy looking coffee table in front of that thing if it was a pull out." I said.

She stopped fiddling with pillows and looked back at me, "Uh, yeah, I think you're right. This looks like just a normal couch." She looked at it again, "A normal, small couch. Fuck, I don't think even I could fit on this thing." She looked back at me, "You definitely won't as your junior year growth spurt doesn't seem to have finished yet." She laughed and looked up at me, squinting playfully. "How tall are you anyway?"

"6 feet, 3 inches and counting" I said proudly. It's true that I wasn't even 6 feet tall when I left high school. Late bloomer I guess. Still, I think I was done growing taller now, and was putting more effort into growing a bit wider by adding more muscle to my slender frame. I was pretty happy with where I'd landed, and I finally managed to start packing on some weight the second half of the year. "But you're just a little squirt, I'm sure you could fit on there," I retorted.

"I'm not *that* little" she squealed and flopped down on the couch. "Look!" she swiveled, and lay back, her feet propped on one arm rest, and her head uncomfortably crooked by the other. "A proud five foot two is enough to defeat this little guy. I am no where near drunk enough to sleep like this."

Tsking and shaking my head, I walked over to the desk and examined the phone. "I'll call downstairs and see what's going on." lifting the receiver, and pressing the "front desk" button.

"OK" she said, getting up, "I'm going to hop in the shower OK?" Before I could answer that we should probably wait until we switch rooms, the door to the bathroom shut and the front desk answered.

A polite conversation, followed by a slightly less polite conversation, resulted in me learning that the booking had, in fact, been for a King Pool View room, that there was no mistake from their side, and that they were fully booked, so no exchanges were currently possible. There was a chance that on Thursday we could switch rooms, but in the meantime, we were on our own.

I sat on the offending couch, and tried to lay on it myself. No fucking way, I thought to myself, my head flat, my legs hanging over the second armrest at the knees. I looked around and wondered if there was room on the floor. I guess that could work I thought with a sigh. 5-star vacation, here we come.

The bathroom door opened, and out stepped a towel covered Alice, her wet hair thick and clinging to her neck. Steam exited behind her and she was back lit by the strong shower light. Smiling at me with her hands on her hips, she looked like she just stepped out of a shampoo commercial. "Ah, I see you are getting comfy on your bed?"

"Yeah, maybe" I said, doubtfully, not feeling like joking about it now. Reality had sunk in, and I knew I was in for some uncomfortable nights of sleep. "I was more thinking about moving the coffee table, somewhere, and then trying to make a bed on the floor here."

She walked towards me while wrapping her head in a second towel that she had been carrying. The motion raised her towel well up above her knees, and I appreciated the shape of her powerful calves and thighs. Realizing I was staring, I quickly looked at her smiling face and she said, "Come on Alex. Let's not exaggerate OK? Look at the size of that bed" nodding at it. "You're big, but you're not *that* big. We can definitely fit. I can trust you, right?"

"Trust me in what way?" I said, not even having considered the possibility of sleeping in bed with her. "That I'm not going to rape you?" I said as a joke, but realizing that probably not the best one for the moment.

Her smile went a bit forced, showing a lot of teeth, "Uh, yeah. Exactly. The bed is a no rape zone." She looked around as if for help and then back at me, "I'm young so maybe not the best read of people, but I know your parents, and they definitely don't seem like the type that would raise a rapist."

"Yeah, not a rapist." I affirmed, "And that's enough of that. I more meant, like, yeah, you can trust me. I am totally fine with sleeping next to you or whatever. But.. uh... will your boyfriend be fine with that?" I internally kicked myself for bringing that up, but best to be up front in this situation I rationalized.

Her expression turned serious but she said, "Yeah, I mean, I'm not sure to be honest. But we don't have any other option right now, and it's both of our vacation. And it's really not fair for you to be over there or on the fucking floor. I'll talk to him about it tomorrow" she said, "but for now, I want to get ready for bed."

I said, sitting up, "Hey thank you so much Alice! You're so much cooler than I thought" stuttering for a second but continuing, "I mean, that's really very kind and I appreciate it and I won't make you regret it. This is the perfect gentleman zone" gesturing to myself up and down and smiling at her.

She was standing, half smiling, head cocked, waiting. I looked back at her, smiling, hands mid gesture, waiting. "Umm" she started finally, "Perfect gentleman? Are you going to stand there watching while I get dressed for bed, or are you going to go shower" gesturing to it with her eyebrow.

"Oh, yeah! Right, cool. Shower. I usually shower in the morning."

"This week you will shower at night" she said.

I laughed and said, "Seems like a good deal if it means I don't have to sleep on the floor." This trip really was turning out well, I thought to myself as I got undressed. I looked at myself in the mirror and realized I was grinning ear to ear. Not only would I be sharing a room with a hot girl, I'd be sharing a bed. OK, she had a boyfriend and wasn't interested in me, but still it would be a fun experience. I gave myself a good wash and spent some extra time cleaning down below, just in case.

I usually slept nude in the summer, but that was obviously not in cards given the current arrangements. I didn't have great sleepwear though, unfortunately, and ended up in my baggiest pair of boxers and a black crew neck t-shirt. I checked myself out, and thought I didn't look too bad. Everything covered and reasonable.

Brushing my teeth, I started wondering what Alice would be wearing. Visions of panties swirling in my head, I could feel myself start to get turned on. No, Justin, none of that, I admonished, I instead focused on brushing. Before my normal two minutes were up, I heard an impatient sounding Alice through the door, "Hurry up roomie, I'm falling asleep but want to chat first!"

Spitting, I answered, "OK, there in a sec" and quickly rinsed my mouth. One last quick check in the mirror before I opened the door.

Alice was propped up in bed reading on the side closest to the bathroom. As she heard me, she closed her book at put it on the side table. The movement gave me a moment to see that she was wearing an oversized t-shirt that showed one bare shoulder unmarred by any bra strap. It was pretty short as well, and I could see a good portion of her golden skin along her side and upper hip. Fuck. I could feel my dick start to lengthen. She turned on her back, and pulled the blanked up and watched me.

Moving quickly, I walked around the foot of the bed to the other side, pulled up the blanket and climbed in, hiding myself before my dick got too expressive. The pillows were voluminous and plentiful, and cradled my head comfortably as I lie there, staring at the ceiling. I turned my head an saw her smiling at me. "OK you, so I just wanted to lay out some ground rules, OK? "

"Yeah sure Alice, whatever makes you comfortable" I said willingly. Curious as to what she would say.

"Nothing crazy, I just want you to respect my boundaries, but I don't want to be a bitch. It's vacation, so we should be relaxed."

"So I should respect your boundaries, but I should be relaxed?" I asked with a raised eyebrow. "You mean I should stay on my side of the bed?"

"Well, yeah" she giggled and drew a line down the center, "This is my boundary." She laughed again. "Don't come in to it unless you tell me too." My dick twitched at that one, wondering why she would even mention that as a possibility. "And I won't come into yours. But look, that side of the bed is yours so you can do whatever you want over there." She grinned at me mischievously as she said that one, and watched me intently for my reaction.

My reaction was to stare at her open mouthed. I closed it with a snap, grinned back, and said, "So you mean I can bring some girl back here so long as we don't cross this line?" I swept my finger down the indent in the sheet between us where she had done the same.

"Ha! I doubt you'll manage to be so lucky on a family trip unless you've really changed." She laughed too long at that one in my opinion, but then she quieted and required her cheeky look, glanced down for a moment, then back at me and said, "I was more thinking that if you need to jerk off at some point, you can feel free."

"What?!" I exclaimed, before she continued.

"I mean, I don't want to know about it OK? That's another rule. Don't do it in front of me, and the bathroom is probably better, but I know how it is with young guys. Always doing it. And I know sometimes you need to, so yeah, feel free. Just remember the no rape rule" she laughed again. "Anyway, yeah, hope that wasn't weird."

"Uh, no, not weird at all." I said shaking my head, looking at her like she was nuts. "I wasn't planning on doing that, I have self control. And, anyway, that's what the bathroom is for" I said, still shaking my head.

"Oh, well, suit yourself. I like doing it in bed" she said confidently, "and if it's OK by you, I might just take matters into my own hands at some point." Her voice got deeper as she got further into the sentence, and it was downright sultry when she ended with, "You don't' mind?"

I rasped back, "I don't mind." My dick was a solid pipe, and it took massive willpower not to reach down right then. Rules are rules, though, she'd definitely know if I did that. I did flex, though, strongly enough to shift the blanket shifted.

She noticed, and smirked at me knowingly, "Remember the rules Justin. But hey, just so you know, I'm a deep sleeper." With that, she turned around, reached to the bedside lamp, turned it off, and lay down to sleep.

-

For a moment after waking, I couldn't remember where I was. I was looking through an unfamiliar window, and I stared for a few moments until recognizing the hotel room. Light from the full moon was surprisingly bright and laying on my face, so I turned over and froze. The sliver of moonlight that woke me had lit the other half of the bed as well.. Alice was sleeping with both arms stretched out above her head, her blond hair splayed out around her. She had kicked the blanked down her entire torso was on display. I felt a stirring as I soaked in the view. Her raised arms had pulled her oversized shirt up such that the bottom of her pale breasts were on display. Her tanned and toned belly made my mouth water. I could feel my pulse rise in time with my cock, which I unthinkingly reached down to adjust under my boxers. Her navel was diamond shaped, beautiful, and I unashamedly could finally stare at the blue stone of her piercing.