After graduating college, I became a professional musician. Like many young artists, my finances weren’t anything to envy, so I lived at home between out-of-town gigs. Whenever I was home, I’d make a few extra bucks helping out at my old high school music teachers as an extra hand, coaching the kids and getting to hang out as peers with the teachers that taught me so much. I loved this part of the job. Plus, a lot of the kids were super talented and were a joy to work with.
Every Spring, the school would hold a fundraiser concert for the arts where alumni could perform a musical number at an evening cabaret. It was always a little corny, but we did it happily. A few years ago, I got an email from a younger alum, Jess, who was in college now and wanted me to accompany her on a musical number. I remember her being a good singer, though very timid and a little mousy. She had done a musical with my younger sister, Abbi, who was the same age as her. She always seemed scared that she was going to mess up, even though I remember her having her material prepared excellently. I wrote back that I’d love to play for her and to drop off her music at my parent’s house.
We scheduled a time to rehearse her song, and it seemed like a few years of college had grown her confidence. Seeing her spirit had grown made me excited to play for her and gave me the bright idea of asking her to perform a duet with me. I had recently found a duet from a musical called *Once* that I thought would be a nice addition to the evening. (If you haven’t heard the song “Falling Slowly”, you should definitely check it out.) After rehearsal, I asked if she’d want to sing “Falling Slowly” with me and she said yes, a little surprised I had the idea. For a moment I thought doing a romantic song with someone the same age as my little sister, but let the thought go. We were both well out of high school and it was just a damn song anyway.
We set a time to rehearse the song and started texting about other, unrelated music topics. She had great taste in music and introduced me to some talented songwriters I’d never heard before.
The next time Jess came over to rehearse, the tone was a little more relaxed. She was a little less deferential to me as a musician and seemed even more confident about making artistic choices. My heart started beating a little faster. Jess was very petite with small breasts, well-dressed, smart as a whip and a cuteness that was suddenly edging towards sexy. I felt weird. I’d never thought this was about anyone my sister’s age. She was 4 years younger so when we both lived at home, an age difference like that would have been strange.
I set that feeling aside to focus on rehearsing the song. We were both super excited to perform together at the fundraiser.
The night of the concert, I showed up to the event a few minutes early to relax, grab a drink, and catch up with some other alum I hadn’t seen in awhile. When Jess showed up, she looked…hot. Jesus, she had a black, skin-tight dress on that didn’t go anywhere near her knees and a plunging neckline that was perfect for her smaller chest. It was elegant and confident, but not too much. Classy-sexy. She mostly hung around alum she had graduated with who I’d also known through the music program. It was always a nice confidence boost to be with them because they looked up to me as a talented alum when they were in high school, so they actually thought I was cool.
The concert began and Jess and I waited our turn to perform her solo and our duet. All of the alum sat at one big table together, enjoying dinner and drinks.
Both songs went off without a hitch and Jess and I were relieved. The school district raised over fifty thousand dollars over the course of the night, so everyone was feeling good. I remembered the year before an alum had hosted a party for everyone at her house after the concert. I thought, “why the hell not? Parents are out of town…I’ll invite everyone over!”
To my surprise, everyone spanning many generations of alum decided to come hang afterwards. I got together some alcohol and we started to party. Post-show glow had us all relaxed and happy as we sipped on some drinks and swapped insane music and theatre stories. Jess and her best friend Elena shared a small seat together, smooshed on top of each other. In Jess’ small dress I could tell she was trying to stay decent and I was still trying not to see her like *that.*
Jess, Elena, my sister, and a few others who had decided to crash at the house instead of drive home inebriated went upstairs to my sister’s room to smoke some weed. I thought about how much more comfortable I was hanging with my sister by the fact that it didn’t feel weird being an adult around her anymore. We were becoming better friends as we got older. As the host, I realized I needed to make sure everyone had a place to sleep, and my buddy Tom was going to share a bed with me so I needed to clean my room a little bit.
I opened my bedroom door alone and realized I had a full load of laundry spread out on my bed, like a slob. My mattress was queen-sized, but I needed to make this hospitable for Tom, so I knew I had to fold this shit. I was just too tipsy to think about it in the moment. I ambled back into my sister’s room where everyone was laughing in a cloud of smoke.
“I have to fold my fucking laundry.” I said and everyone laughed. I heard a voice chime in.
“Do you want some help?” Jess said.
I didn’t know what to say at first. There wasn’t a strong hint of suggestion in her tone, she just seemed to like me and wanted to help.
“Sure.” I chuckled, “Thanks!”
She crawled over some bodies on the bed and dismounted, joining me at the door. We walked out and went to my room.
“Well, here’s my very exciting bedroom.” I said deadpan. She giggled a little.
“*Very cool.”* She replied. I didn’t have much of anything in here since I was so transient, but there it was, a nice pile of laundry to put away.
“You sounded great tonight, Jess.”
“Thanks, you did too. I’m so glad you had the idea for us to sing a duet. I was surprised.”
“Honestly, me too. But when you came over to rehearse your solo I was inspired.” I said with a small laugh.
“That’s sweet. Ok, where do we start?”
“Oh, Jeez, I dunno. I guess why don’t you fold some tees and I’ll take care of my underwear, you don’t need to go anywhere near those.” I said with a nervous laugh. Jess laughed.
“I don’t mind.” She said, picking up a pair of my boxer briefs. My heart started to race. I was starting to get nervous and didn’t want to get turned on. But my subtle flirty side was begging to come out.
“I like that pair, but you gotta see my favorite pair.” I said with a mischievous grin. “Check these out.” I picked up a pair of underwear I had bought in Paris that was off-white with a floral pattern. I thought it was hilarious to have underwear so comfortable that weren’t trying to be macho. Having them made me feel a little flirty. Jess’ jaw dropped in a self-aware, over-dramatic laugh. She thought it was cute.
“I fucking love these. I’d wear them.” She said. I realized at this point it was getting late and she was still in her dress.
“Do you want to borrow to clothes? Pajamas or something? I don’t have anything small enough for you but still you don’t need to sleep in that dress.” I offered.
“That would be great actually, thanks.”
“Ok, well what do you want? I have tees, shorts…underwear? If you want?”
“I’ll just take one of your tees and maybe a pair of underwear.” She replied.
“Take whatever you want!” Jess considered her options and grabbed a colorful pair of boxer briefs and a plain white v neck tee.
“Do you…want me to leave while you change, or…?” I asked.
“No, that’s ok!” She replied.
“I love that dress by the way.” I added.
“Oh yeah?”
“Mhm”
“Thanks.” She said with a smile. “I don’t have a lot going on up here.” She said, gesturing to her chest, “So I can get away with dresses like this.” She said, mischievously. I was getting nervous, but we were having fun together so I tried to keep it together.
“Well, you definitely…uh….I mean, it…it works.” I said, playing up the awkwardness. She got that I was saying she looked hot without using the words. Jess blushed and smiled. I smiled as my heart raced faster.
“You should put on those floral underwear, I wanna see. It’s too good.” She said a little flirtatious.
“Oh, jeez. Ok, I’ll put them on it’s just…they’re not the most….decent.” I said, warning her.
Jess laughed, “That’s fine, look at my dress for god’s sake. It’s only fair!”
“Ok, ok, true.” I said nervously, grabbing the floral underwear. “Fine, I’ll put them on.”
Jess turned around and I paused for a moment as I realized I was about to take my pants and underwear off in the same room as her. Then I unbuckled my belt and dropped my pants and underwear, slipping on the Parisian pair. I made sure the little red button on the pouch was done up and said, “Ok, here they are!”
Jess turned around and with a huge grin put her hand over her mouth laughing.
“Oh my fucking god, I love them.”
I realized how exposed I was and remembered that little red button had trouble staying shut.
“I told you they’re not decent!” I said.
“No, they’re so cute and ummm…” She was looking at the outline of my cock that was now at half-mast in the underwear and threatening to come out.
“God, yeah, sorry.” I said, covering up a bit with some futility.
“Can I feel them?” She asked. “They look super soft.”
“They are, and yes you can, but…”
“I don’t mind.” Jess stepped forward to me and felt the fabric on my upper thigh as my cock began to grow ever more. She looked up at me. “You have really nice legs actually.”
“You do too.” She quickly grabbed my hand and brought it to her waist.
“I fucking love this dress, doesn’t it feel so comfy?” She asked.
“Yes, it does.” And as Jess removed my hand from my crotch to feel her dress, my cock started to emerge from the Parisian underwear. “Oh shit, I’m so sorry.” Jess looked down and could see it was already starting to drip with precum.
“Fuck.” She gasped. Jess took one hand and ran it timidly over my cock as I gasped quietly. The hand that was on her waist moved down reflexively and grabbed her ass, which was thick as hell given how small she was. It felt so firm and round in my hand. Jess’ breath got caught briefly as she got more turned on by this first contact. We made intense eye contact as she kept one hand around my shaft and brought her other hand up to my face, feeling my jawline and running her fingers over my lips. As her fingers passed, I snatched one with my lips and tongue and started to suck on her finger, bringing my free hand lightly up her plunging neck line. She reacted with a gasp and I slowly ran my palm up the middle of her chest between her tits and moved my hand over, sneaking under the dress to grab her tits, feel her nipples. This is when Jess finally moved her mouth greedily up to mine as we began to taste each other, madly.
My cock, getting smooshed beween our torsos, was wiping precum all over the front of Jess’ dress as it was escaping my underwear.
“Fuck, you’re so hot.” I managed to say in between kisses.
“Take off my fucking dress.” Jess commanded.
From her shoulders, I released her dress down her body as she stand in front of me in nothing but a pair of black, lacy panties. I reached a hand down to feel her pussy over her underwear and felt how hot and wet she was. She grabbed my shirt that was still on and began to pull it over my head as I was now naked save for the floral underwear with my cock raging hard through it’s opening.
She went back to my dick and started to rub up and down the shaft faster.
“I’m so fucking hard, jesus.” I whispered. I realized how close in proximity we were to the rest of the party and was trying to be quiet thought even that turned me on even more.
Jess, being much smaller than me was easy to pick up, and I grabbed her by the waist and tossed her on my bed, over the rest of the laundry as I greedily pulled down her panties. She was clean shaven with a small, neat labia and so wet already, but I needed to taste. I brought my tongue down to her and began to suck and lick, listening for her response. As I ran my tongue left and right over her clit slowly, she began to moan.
“Fuck, keep going.” I followed her direction, trying not to cum myself. She tasted clean and lusty, fucking delicious and her response was edging me closer, but I wouldn’t let myself cum yet.
Sooner than I thought she said, “Keep going, I’m gonna cum.” My tongue was getting tired but I kept up the pace for her as an orgasm ripped through her body, her legs quaking as she tried to stifle a moan, still letting some out loud. “Holy shit, that felt amazing. Come here.” She pulled lightly at my hair to bring my head up to her chest and head and my cock close to her aching pussy. We kissed and she tasted herself on my tongue while I made my way down her neck to her small, perfect tits and licked her nipples, sucking and tasting. She moaned “Please, just put it in me.”
I slowly reached a hand down to my pulsing cock and brought it to her pussy, running the head gently over her clit and labia, getting the head wet, rubbing precum all over her. I slowly put just the head in her velvet opening as she was still sensitive from her orgasm.
“Oh my god, you feel so fucking good. You’re gonna make me cum so quick.” I said, breathlessly.
“Fuck me. Slowly.” She begged.
I eased my whole cock inside her slowly, relishing every inch along my shaft. I could feel her walls and ridges sucking me in, begging me to go deeper. I put my cock all the way in and removed it slowly with a gasp. In and out I went slightly faster each time until I was pounding away bringing myself even closer to the edge. I reached up with one hand and grabbed at her chest with one hand gripping her thigh as I thrusted into her. “Fuck I’m gonna cum.” I said.
I went faster and faster, racing to the edge as I felt a massive load coming. I pulled out my cock from her velvet pussy and kept thrusting on her slick vuvla as I came rope after rope onto her belly, chest, some on her face and the wall behind her. I tried to be quiet but the orgasm tore through me so forcefully I couldn’t help but moan. Out of breath, I looked down at her, also breathing heavy, covered in my lust for her as she reached her fingers down to her clit and began touching herself again. My cock, still hard, she guided back inside her to feel me as she came again, her whole body shaking.
“Jess.” I said. “Jesus christ, you’re amazing.”
“I can’t believe this just happened!” Jess said. “I had a bit of a crush on you, but I never thought you’d see me like that. It was just a silly thing. Holy shit that was so hot.”
“No kidding. I didn’t see this coming either, but you’re so cool. And hot. I’m glad we got to spend more time together.” I gave her a kiss and grabbed a towel and some tissues to clean up her soaking body.
We laid there for awhile, enjoying each other’s company in silence until my cock started growing again…
Jess looked at me and smiled, biting her lip.
Source: reddit.com/r/eroticliterature/comments/v5s3sh/a_surprising_connection_m25f21
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