The Sheltered Band Girl Puts on a Show

Wow, who would have expected the nerdy band girl to do that in front of me?

Ya see, growing up in high school and college I didn’t have the numbers of experiences with girls that a lot of guys did, but the ones I did have were pretty intense - even the ones that didn’t end in full sex. This one certainly fit in that column, and what better place to have it than on a senior trip in paradise. 

It was the early 2000s and my high school band went on a trip to Hawaii in my senior year to play in some parades and stuff. I played trumpet and looked forward to the events, but like most of the rest of the group  I was really just in this one for the trip. A reprieve from midwestern winter for a week and a half on a tropical island with about 600 of my classmates (I went to a big school). 

I shared a hotel room with 3 other guy friends and, as one of the others was dating a girl in the band, our group ended up hanging out the whole trip with her and her 2 girlfriends. These three were by no means the most popular girls in the band, or our class, but they were nice and a fun group to get to know. One of them was actually one of the band’s drum majors: a girl named Becca. Becca was certainly a ‘band girl,’ ya know: really took it seriously, but she was also kind of cute with a decent body that was usually hidden under baggy tee shirts and jeans. As I got to know her throughout the first days of the trip though, I really became intrigued by her and noticed her a bit more as I got to see her in a swim suit at the beach. 

That was the most intriguing thing though. As we got a few days in the trip, I could see Becca loosen up a little. She was apparently brought up in a fairly sheltered, Christian home and as a result she harbored a suppressed, wild girl side that really wanted to get out. She wasn’t shy about those facts, bringing the topic up several times, and also being backed up by several eye rolls from her roommates with the inevitable comment every time, ‘That girl needs to get laid already!’ This all became clearer as I saw signs of that loosening day-to-day. After the first beach day where she showed up in a pretty plain one piece, she showed up the next day in a 2 piece bikini with signs of ‘bikini zone’ shaving fresh along the edge of her bottoms. She also slowly started joining in with our more sexual topics of discussion as we sat around each other’s hotel rooms at night. And though I was in a sort of loose, not really committed relationship with a girl back home, Becca seemed to have latched onto me a bit as the trip went on; I sensed she liked me, though I was a dumb teenage boy and wouldn’t be too confident in that call. 

However, that seemed to be confirmed on night 3. The four of us guys sat in the 3 girls’ room playing some game against them and getting more and more competitive in our little ‘battle of the sexes.’ Eventually we ended up making some bets on the games with semi-embarrassing dares on the line. Us guys proposed that if we won one game the girls would have to clean our hotel room in their swimsuits (it was the horny 2000s after all), but the girls handily kicked our asses and we had to do some embarrassing karaoke while they recorded us instead. 

Becca though, we all found out, was particularly competitive and began needling even her own teammates with it as the games went on. 

“Bet I can out-do you in your own subject here Stace,” Becca said to her friend Stacy,  to a confident eyebrow raise.

“Well maybe we should make this a little more interesting, too,” Stacy responded. 

Their other friend told them maybe their bet should give us guys a little fun; since we missed out on the bikini cleaning wager. The two, competitive as they were, decided that if Stacy lost she’d have to flash her bra to all of us. Becca’s dare, they agreed though, should be tougher since she’d grown so cocky in her abilities. 

“I think, you lose: you should give the guys a sexy little strip-down…at least to your underwear,” Stacy said as Becca gasped and smiled embarrassedly at the thought. 

“No, that’s too much,” said the other friend before turning her face to a mischievous smile, “at least a little too much. How about a sexy strip down for just one of them.”

“Yeah, just for,” Stacy jumped in before scanning the room with her eyes and stopping in my direction. “Just for Ricky.”

My eyes opened wide at the suggestion and instinctively looked to Becca who was, too, looking at me now. She was beet red and glanced over to her other friends to give them a look. It wasn’t a look of disbelief at the suggestion though, rather it seemed to be like a look of disbelief that her friends had…actually suggested it; like maybe they’d discussed a scenario like this in fantasy and had suddenly had the guts to push their sheltered friend into such an experience. 

“Alright, you’re on,” Becca said brushing the idea away awkwardly. “Not like I’m gonna be the one paying up at the end of this anyway.”

But…she was. Stacy, it turns out, really was an expert in the current category of the game and she handed Becca her first,  decisive loss of the game. The drum major sat there, red faced and in awe of her defeat as the others in the room hooted and laughed about the coming consequence for her. My stomach immediately filled with butterflies at the situation as I tried not to smile too much - not to show my excitement at the prospect - but to also not seem creepy about this whole thing…just play it cool. 

“Well, a bet’s a bet, Becca,” said my buddy Dan as he slapped me on the back. 

Becca’s friends must have sensed her embarrassment and, likely, nerves at the situation, as they seemed to try to calm things - while also not letting her off the hook completely. 

“Okay, okay everyone,” said the third friend, “we’re gonna be respectful about all this. If we’re gonna make her go through with this, why don’t the two of you go back up to the boy’s room and have the pay up. Rick’ll report back to all of us that it actually happens, and we’ll make sure it stays private and these 3 don’t barge in.”

Becca and I both raised to our feet and walked to the room door to shouts of encouragement and laughs from behind us. We walked out and into the elevator, taking an awkward ride up to the floor us guys were on. We tried to make little conversation and shoot each other smiles on the ride, but we both knew what we were going to do. 

I opened the room door with my key and Becca and I walked in; assuring no one else was there and that we locked all of the locks on the door to prevent any walk-ins. We still had a good 2 hours till the chaperones would make their rounds and no one else would have reason to come to the room. 

So there we were: Becca and I alone in a hotel room in Hawaii, seniors in high school…about to really act like it. The air between us was awkward, to say the least, as we giggled and made glancing eye contact. 

“So…” Becca said to me nervously. 

The ‘good guy’ in me cut through my teenage horniness at that moment though, and tried to ease off the gas a bit. I knew how sheltered Becca had always been and didn’t want her to feel pushed into this; despite being pretty sure she was leaning toward pushing her own boundaries a bit on this trip. However, talk is cheap and maybe that’s all her horny teen talk was. I didn’t want to push the girl. 

“Ya know: you really don’t have to do this if you’re not comfortable,” I said to her with a more comforting, sincere smile. “I mean, I’m not against it, but… I totally get it. I can just tell the others you went through with it.”

I’d shot my own opportunity in the foot, hadn’t I? My chance at a sexy experience on this trip and I blew it, right? Turns out…no…I certainly didn’t. 

“Thank you, that’s sweet,” Becca said as she turned her body and pulled out the chair from the desk nearby, moving it to the center of the room. “But, I made the bet, and I’m not gonna go back on it. I knew what I was getting into.”

Becca gently placed her hands on my shoulders, standing in front of me, and pressed me down into the waiting chair. My butt came into contact with the chair and I immediately smiled and nodded at Becca. She flashed a happier smile now as she pointed to my CD case and picked a disc from the pages; putting it into a small stereo that one of the guys had brought and starting some 80s rock music. She turned the volume to a reasonably low level - something that wouldn’t get any attention outside the room - and turned back to me with a more focused look. 

As the music played, Becca began moving her body along with it and giving her best, band nerd take on a stripper dance. At first, she was very awkward as she rubbed her hands up and down her sides and tussled her long brunette hair from its pony tail. 

“I think I see a sexy side behind that serious facade,” I said to her with a smile, trying to help her gain some confidence and loosen up. 

Becca smiled back at the comment. 

“I told you: I’ve been sheltered,” she said. “Maybe it’s time I live a little.”

With that exchange, Becca settled into her dance and her body seemed to find its rhythm. Suddenly, her hips began moving with the music and the curves of her fairly average, yet shapely body began to show through her tee shirt and short jean shorts. Her face went from nervous and awkward to more: nervous and a little turned on. This was clearly Becca pushing her limits, and she seemed to like it. 

I sat on my hands, as I was told to in the only real strip club experience I’d had to that point, and watched as she danced closer to me, running a hand across my shoulders. Becca then turned around as she placed her body between my spread legs and rubbed her ass down my front into to my lap. As she moved her butt over my shorts, I could feel my dick harden inside. My instinct was to try and conceal it, but instead I let it poke up against her as she put her cheek against mine and looked back at me slightly.

“Is this okay?” she asked in a voice, more looking for reassurance that she was, in fact, doing it right than her trying to be sexy. 

“Yeah,” I said in a more alluring voice than before. “You’re not so bad at this Bec.”

She gave a much more comfortable smile and shrugged with a joking look of confidence on her face as she pushed off from my lap and turned to face me. Becca planted her feet and ran her hands up her hips on either side. As she reached the hem of her baggy white tee shirt, her fingers curled upward and she began pulling it up. Her semi-toned belly came into view first, looking slightly pink with a fresh Hawaiian sunburn from the last few days. Then, holding eye contact with me until now, she closed her eyes, let out a calming exhale to let go of her sheltered sensibilities, and pulled the shirt over her head in one solid motion. A white, lacy, though fairly unremarkable bra was now on display in front of me and inside of it sat a lovely pair of B cup breasts. I’d seen her in a swim suit the last few days, but seeing Becca’s cleavage inside of a bra, even one fairly basic, made me really appreciate how low-key sexy this band girl was. 

We smirked at one another as Becca resumed her little dance in front of me. Now, clearly empowered by her personal boldness so far, Becca wasted little time letting her hands run downward, over the top of her bra covered breasts, down over her smooth belly button, and directly to the button at the top of her jean shorts. She undid the button rather unceremoniously and pulled the short zipper open in a quick motion; this closet horn-dog was eager to explore more. She bent forward and pulled the shorts off to reveal a pair of white cotton panties; rather plain like the bra but that added to the good girl going bad vibe that I was really enjoying in that moment. 

Now, standing in front of me in her underwear, the drum major channeled the impulses she was embracing and started really adding every bit of sexy she could into her strip dance. Becca’s dance continued to feel like a slightly awkward attempt at a strip tease by someone far from practiced, but that too added to the appeal of her performance; coming from her. She took shorter breaths now, flushed in the cheeks, and stared intently into my eyes as she stepped her swaying hips into my bubble again. This time, Becca spread her legs apart as she swung one onto either side of me on the chair. I couldn’t help stare as the cotton covered mound in the crotch of her white panties as she placed her hands on my shoulders and moved her hips, inches away from my body. She moved her body as seductively as she knew how to, continuing to hover herself just a bit away from letting her cotton panties make contact with my body; a threshold she was still working up the urge to cross. 

“God, you’re fucking sexy,” I said to Becca in a sultry voice; reassuring her of her performance attempt. 

The reassurance must have worked because I could see her bite her lower lip and push things even further. She moved her hands from my neck and used one to playfully pull one bra strap down. With the other hand she gently played with the waistband of the cotton panties; pulling them down ever so slightly. 

“You really think so?” she asked sincerely with a little extra blush going into her cheeks. “Is it wrong I’m kind of enjoying this?”

“Not at all - you should,” I responded. “For the record: I am too. Let it out; have some fun.”

As I said those words, the music playing on the cd switched to a power ballad and Becca stopped swaying her hips. Now, she allowed herself to lower down onto my lap. She shuddered a little and looked down at her crotch as the white cotton came into contact with the tent standing up in my pants. I felt her lose her balance a bit as she tried to remove a hand from my shoulder to make her next move, so I instinctively removed my hands from beneath my butt and place them on the small of her naked back. She smiled and said, ‘Thanks,’ as she was now steadied on my lap.

Becca returned to biting her lower lip though as she now slid one of her free hands to the lowered bra strap she’d brought down moments earlier. She looked down at herself as she slowly pulled the basic, lacy left bra cup down, letting her pale breast slowly come into view. I could feel her begin to rock her hips against me a bit as her hard brown nipple came into my view - likely the first time she’d ever shown it to a guy before. With one now visible, she wasted little time bringing her right hand up to the other strap and pulling that side down as well; fully exposing her chest. I let out a gentle moan and let one of my hands rub the small of her back a little, sending subtle approval of what I saw. She freed her arms from the straps and looked me in the eyes timidly. 

“A little help?” she said, nodding her head backward. 

I gladly, but gently moved my right hand up her back and found the clasp of her bra, flicking it free with my fingers and watching as it fell from Becca’s body and onto my lap. She picked it up with a raised eye brow and, using one hand one each side of the clasp, brought the bra behind my head. She then used it to pull my face forward, between her naked breasts where she rubbed them against me. This was a bit aggressive and clunky compared to the kind of motorboat you’d get at the strip club, likely due to her inexperience with this kind of move, but it still got me going like mad. The feel of her soft boobs against my cheeks was intoxicating. After a few seconds she even positioned her hard right nipple between my lips where I let them part and gently ran my tongue over the brown nubbin. That feeling sent her hips into a full, thrusting rub against me as she let out a tiny moan of pleasure. 

With that, she let the bra drop and placed her shaking hands in my hair, pulling my face out from her chest to look into my eyes again. 

“Is it okay if I kiss you?” Becca squeaked out, in what seemed her most nervous move yet. 

I didn’t even respond. I just moved my right hand to the back of her soft, long hair and pulled her face into mine. Our lips came together and quickly parted for our tongues to dance in one another’s mouths. I assume this was her first kiss, a night of many firsts for her clearly, but she was surprisingly good at it. As we made out I lowered my other hand onto panty covered butt, again, causing her to release a gentle moan into my mouth as I helped her rhythmic movement against my lap. I could feel my boner rubbing directly against her soft crotch. At this point in my life, this was the closest I’d come to full-on, genital on genital sex, and who woulda thought it would be with this sheltered marching band enthusiast. 

She pulled her lips from mine as her face looked lost in her own senses. 

“So I actually was just experimenting with something the other day,” Becca whispered in a shaky voice as I grunted back in inquiry. “I, uh…I tried shaving. I know the bet was just to strip to underwear, but do you wanna see?”

“Fuck!” I said, unable to find another word in my shock. “Yes I do.”

Becca smiled and raised up from my lap, getting to her feet and standing a foot or two in front of me. As the power ballad played on in the background, she hooked the thumbs of her nervously shaking hands into the waistband of her panties. She slowly started peeling them downward, allowing some small bumps of first time razor burn on an otherwise smooth pubis to come into view. At first she seemed to pause and decide on only showing me that much, but then I saw her close her eyes gently and bite her lip again as she pulled the fabric over her butt and let them fall to the ground. There it was: Becca’s completely shaved little slit was right there in front of me. It was a slightly darkened pink from rubbing against my pants and, even between unparted legs, glistened with horny moisture from her boundary pushing experience here. 

“Wow,” I said nervously as she stood completely naked, just a foot in front of me in this dim hotel room. “I like it.”

Becca backed up to the bed that was only another foot or so behind her and sat down on the edge. She placed her hands on her thighs and slowly spread her legs apart in front of me. As they opened, her pussy spread slightly as well to reveal more of the swollen, gooey pink inside. 

“Thanks,” she said with a nervous smile. “I think I kind of like it too. It’s so smooth.”

As she said this she looked down at her own crotch and let her right hand gently rub against her hairless pubic area. She then let her finger tips slide down onto her hairless pink lip and run along it gently; collecting a little wetness on her pointer finger and sending another unconscious moan through her mouth as she took in the feeling. 

“I really like it,” I said to her, with my eyes glued to the wetness on her finger. 

She looked back up at me with that horny little smirk again. I just nodded, encouraging her to keep going, and that’s exactly what she did. Becca brought that wet finger back to the top of her pussy, but this time she let it slide right down the center of her slit. She breathed shakily as her finger tip crossed over her clitoris and down her opening. She then brought her middle finger into the mix as well, this time, tracing down the center of her pussy and causing it to open even further. Her very swollen little clit was now visible to me as she gently brushed either side of it with her finger tips. She continued down and strings of her lady goo parted with her folds as she spread them ever so slightly to give me a look inside. I know the whole ‘tightness’ thing is a bit overplayed, but in this case it was so true. I, to this day have never seen a pussy that looked as tight as her little, untouched, band geek opening did. 

And there it was. I now assessed the whole situation in front of me and realized what was happening in that moment. My sheltered drum major had gone from putting on a little, joking strip show for me, to straight up masturbating in front of me. 

She kept letting her fingers take that path up to the top of her clit and down her tight vagina over and over. Her face looked dreamy with the sensation she must have been feeling in the moment, and after six of so of those strokes through herself, she seemed close to the edge. As her eyes locked with mine again and she remembered where she was for a moment, I nodded once again before sliding my chair closer to the edge of the bed and position myself just inches away from her between her parted legs. 

“Just go with it beautiful,” I said to her. “Let it out.”

Becca looked me deeply in the eyes as she let her fingers run a little faster through her wet pussy. I could see her trying to resist leaning back, to keep at my eye level, but seeing her struggle as she stroked her clit, I leaned in and placed my hands gently on her smooth thighs. 

The feel of my touch was all it took. Becca quickly laid back on the bed as her whole body seemed to spasm and she started gasping. I felt myself leaning in until my face was only about a foot from her fast moving fingers. The sweet smell of Becca’s horny pussy starting to cum filled my nostrils. 

“Please…touch me!” she gasped at me. 

I didn’t skip a beat. I reached my right hand up to her beautiful pussy and I just gently pressed the tip of my index finger into the center of her warm, swollen pink hole. I applied almost no pressure just because I didn’t know how much her virgin self could handle, but as the feeling of my warmth there hit her, her incredibly gooey vagina pulled the tip of my finger into her. I may have barely had an inch of finger in her and Becca was deep into a hard, Earth shattering orgasm. Her pussy squeezed my finger tip again and again as her body quaked with each wave. She gasped and moaned, holding in her urge to scream as she came for what seemed like 30 or 40 seconds. As she kept cumming, Becca’s juices even ran down my finger with some dripping into her butt crack below. 

It was an incredible thing to experience with her, especially knowing how much she’s wanted to let loose like that after a sheltered upbringing. I was rock hard and close to cumming myself, in my shorts, as she slowly began to wind down. She curled up a bit and hugged my arm as the last small waves ran through her and onto my finger. She calmed down and I gently pulled my finger tip back out; sending another little jolt through her body. 

As Becca continued to clutch my arm and regain her breath, she looked up to my face again. I leaned in and kissed her which she lapped up as she continued to embrace the feel of my arm hugged between her tits and against her naked stomach. When our lips parted, she seemed to be breathing nearly regularly again and let out a little giggle. 

“Well I say this 100% truthfully,” I said to her, “that was, easily, the best strip tease I’ve ever seen.”

We both laughed as she loosened her grip from my arm and let me go. The next few minutes consisted of Becca slowly redressing and us talking about what had just happened. She worried that she went too crazy, but I assured her that she didn’t and was just finally being the free, sexy young woman that she has every right to be. By the time one more song played through and she was completely dressed, she seemed to be in a good place about everything and happy with the experience. We went back down to the girls’ room, sharing one more kiss in the elevator before going back in. 

Upon entry, the two of us smiled, slightly embarrassed as the rest of the guys and girls cheered and whooped at our return. 

“So, did she put on the show Rick?” Dan asked with an eyebrow raise. 

Becca stuck her tongue out at him, which got a laugh, and I nodded my head calmly. 

“Becca fulfilled her end of the bet,” I said flashing her a smile. “Now, back to the game, eh?”

I didn’t expand on it any further, only later telling the guys in our room that, ‘It was awesome, trust me.’ However the details of our private dance would remain that: private. 

The next morning at practice, I lined up with my fellow trumpeters as Becca walked by, back in drum major mode, looking as every bit her sheltered self as ever. I wondered to myself if she’d remained positive about the experience or if she’d rolled back into Christian regret over things. My answer came moments later though as she sauntered up to me while the band finished lining up. 

“Hey,” Becca said to me calmly. “I actually stopped by a little shop, up the road from the hotel, before we headed out this morning. I’ll have to show you what I got later - it’s pretty cool.”

I told her definitely, with a smile. Then Becca, oddly, fumbled her drum major whistle and dropped it on the ground in front of me; strange as there seemed no reason why she’d drop it. I went to pick it up for her, but she put up a hand. Becca stepped in front of me and bent down to pick it up, lifting the back of her tee shirt casually as she did. With that, as she bent butt-up in front of me, I was able to clearly see a pink thong riding up from her low-rise khaki shorts. This was a far cry from the simple white cotton she wore the night before, and it was clearly meant for my eyes as she bent in a direction where only I’d have a clear view. She rose back up with a smirk and leaned in to me casually one more time. 

“Call that a little preview,” she said before walking forward toward the front of the band. 

Let’s just say we found some more chances, the rest of the trip, to sneak off for some more experiences. A sheltered band girl…no more.