This is a work in progress and is not a quick fap, I hope to add more sex in the beginning after another round of editing, but for now I just want to share this. Hope you enjoy!
~~~~~~~
“This is your pilot speaking, we’ll be landing in Chicago…”. I ignored the rest, too excited to finally be here. Chicago, the Windy City, the Second City, whatever else people are calling it nowadays. I’d been here a couple of times with my family when I was younger. We’d go to the zoo and the pier every time we came. Dad always talked about moving to the big city. Until a weekend of expensive food and parking convinced him otherwise.
Today I’ll be making his dream a reality thanks to the *fancy* new job I landed. My new company was clear, they needed me asap, so I hopped a flight quick as I could. I came with nothing but a duffle bag, backpack, and the clothes on my back. To be honest I didn’t own much else. Anything else I did own I left for my old roommates to fight over.
I thought finding an affordable place to stay was going to be difficult but once word had gotten around about my move that problem fixed itself. My friend Kyle reached out to me and insisted that I stay with her. I could hardly say no. The rent she was asking for was a fraction of what I had been quoted during my short search. I also thought this might be a good time to reconnect with Kyle.
I haven’t seen Kyle since the summer after they started transitioning. And I’m curious to see how they’re doing. Kyle had surprised no one when she came out. But once she told her family that she felt she was born into the wrong body shit kind of hit the fan.
Kyle’s mom had always been supportive. For her father, however, that was the last straw. See Mr. Liu, Kyle’s dad,was a real man’s man. I’m talking cigar smoking, beer drinking, car fixing man. So, when Kyle told him that she was a woman he flipped. It was all ‘I Have no son, that’s unnatural, and I didn’t think this could get any worse.’ It was heartbreaking. The only saving grace was that Kyle was leaving for college at the end of summer.
After we went our separate ways for college, I didn’t really see her again. We still spoke on occasions though. A text here, a phone call there. I tried to find them on social when they got popular, but according to Kyle’s mom, she was avoiding social media. I found that hard to believe. Figured Kyle was hiding it from her family. Every time I tried to bring it up, she would avoid the subject. Eventually, I let it go, happy to not be cut out completely. Especially since I consider Kyle to be one of my best friends. Which wasn’t saying much. I’d all but stopped talking to my high school friends. My college friends now scattered across the country chasing new opportunities.
While walking through the terminal A TSA agent approached me. “Excuse me, sir. It’s required to wear a mask while in the airport.”
I nod and give a halfhearted apology before pulling my face covering up, still getting used to this thing.
Damn, Covid-19 has everyone on edge. I’ve been talking to my mom on a near-daily basis to keep her calm. Only recently had I convinced her that we only needed once a week check-ins. Though the sparsely populated airport reminds me how things have changed. Thinking about It creeped me out.
Let’s grab this Lyft and start the next chapter of our life Darcy. New city, new experiences, and an old friend.
The Lyft wait surprised me. I almost ended up grabbing one of the few taxis sitting out front. At least my driver was friendly, like really friendly. At times it bordered on flirting, or at least it felt like it. Our conversation revealed that I may not have arrived at the best time.
“Yeah, they’re talking about shutting it all down,” my driver said over his shoulder.
“What do you mean ‘it all’?” I was beginning to worry.
“No one in, no one out. Like a fucked up Thunderdome or actually Under the Dome. Have you seen…”
I started to spiral when I heard that and completely spaced on whatever my driver was saying. ‘No one in or out’. What the hell had I agreed to by coming here? I hadn’t checked my email since before takeoff, what do I do about work if things are shutting down? How do you even onboard a person without a tour of a break room, littered with ‘if you finish the pot start another’ flyers?
“Hey, you still with me?”
“Sorry. Lost in thought.”
“Is here good?”
We had pulled up to an old multi-level brick building. Two identical buildings sandwiched it. looking up and down the block I saw more of the same. Seemed there was a theme here.
“Um, I think so. This is actually my first time here.”
“Well, welcome to Boystown!”
“Boystown?” Seemed like a pretty queer name for a place, he must have been joking.
“Yeah, that’s the neighborhood. Great place to live, even better if you like the boys.” there was a playful tone to his voice
“Like, like, like?”
“Yes, ‘like, like’.” he laughed
I must have screwed my face a little bit because the driver gave me a questioning look. I immediately fixed it, not meaning to be rude.
“Take it you’re not a boys fan?”
“Meh, Not really. We’re way too hairy.” I joked hoping I hadn’t offended my driver. I’d be sure to leave a bigger tip.
“Ha, that’s half the fun. Opportunities present themselves when you leave yourself open, consider that while you’re here.” he had turned around and was definitely giving me the once over.
“No promises, but thanks for the advice. Have a good night, you stay safe.” I couldn’t get out of the car fast enough. Is that how women feel when men check them out?
Damn, that sucks.
I walked up to the door a little hesitant to ring the bell. Not just because of the hour, but because I wasn’t even sure this was the right building. Before I could decide a course of action the door swung open. Kyle ran out and jumped into my arms almost forcing me to lose my balance.
She pulled back a little to make sure I was alright “Sorry, are you ok?”
“Of course,” I laughed. “A little warning next time though”
She leaned back in, her embrace not letting up for a full minute. I decided to lean into it. She obviously was happy to see me. I lowered my head fully giving into the hug.
She smelled amazing. A light floral scent, it was as familiar as it was inviting.
“Ok. Sorry, just had to get that out of the way” she said as she began to end our embrace
Her grip finally loosened, unmolding her from me. Finally letting me have a good look at her. She was even prettier than I remembered. She had definitely matured. And in the best ways possible since I had seen her last. She had put on weight, but who amongst us haven’t, the bulk of it filling out her ample hips and adding a slight pudge to her stomach that was begging to be grabbed. It’s softness ready to be kneaded by diligent hands. The thin white tank top and purple cotton shorts she wore hugged her in all the right places. Exposing fields of pale ivory skin to the cold night air.
Her straight black hair was in a single braid. It laid casually over her shoulder and down her chest, drawing my eyes to her visible nipples. Her breast having grown since I last saw her. What was once a small A cup at best now looked to be a very healthy and full B cup. After taking in the pristine image I had been presented I decided that I should speak before this gets weird.
“No need to apologize, who doesn’t love hugs.” I joked, brushing off her apologies.
Flatly she responded “Athena”
“Who?”
“You’ll meet’em later come inside, it’s chilly out here.”
From what I could see through her top she was indeed *chilly*.
“It is? I couldn’t tell.”
“Be nice or I’ll send you back to Bumphuck, Indiana”
“Don’t think I’m allowed back. That’s a one-horse town and I don’t think they could handle another stallion.” I said with a wink and a nod.
Kyles responding groan was quite audible, coupled with an eye roll. “Not here 5 mins and you’re already making bad dad jokes”
I Gave her the good ol’ finger guns in response.
It felt natural to fall back into the way we used to banter. Trading quips until one of us broke out in laughter.
“Get in here fool”
Kyle Tugged me by the arm into the foyer urging me to sit my things down so she could give me the Nickle tour. The next room we entered was a good-sized sitting room. The setup was a lot nicer than I was used to. They actually had framed art! That may not sound like a big deal, but I’d been basically living the dorm life with a bunch of other guys for the past six years. When it came to wall art all we had were free Concert and Movie flyers we scored from a friend who worked at the local box office.
The furniture in the room looked comfortable, if not a little worn. It may have been second hand, but it was definitely being taken care of. All the pieces even matched each other, something else that impressed me. The furniture in my old apartment was a mixture of Home Basics from Target and cheap or free Craigslist finds.
“This is the family room, where we…family.”
“Smooth”
“Oh shush, and c’mon”
Kyle turned to lead me further into the apartment. My eyes were immediately drawn to her stretched shorts. The distinct lack of a panty line left my mind to consider the options. I’d never known Kyle to wear thongs, she always said they were uncomfortable. So, was she wearing no underwear at all? As she started to walk the shorts rode up a little revealing some of her tantalizing ass. The tease alone was enough to get me going.
Focus Darcy. You’ve seen butts before, what’s wrong with you? Yes, Kyle’s cute, but remember what’s on the other side of that nice thick…dammit man c’mon. Eyes up, new apartment, take it in.
We walked towards the back of the apartment passing two sets of stairs, one up the other down, I assumed my future room lay somewhere above. Maybe even near Kyle’s. Not that, that would matter I mean me, and Kyle are *just friends* and, well, she wasn’t like other girls. I decided to focus on the tour, again. I don’t know how long I was planning on staying but these were thoughts I did not want to have to deal with while I’m here.
Walking through a hallway we enter a reasonably sized kitchen. The kitchen was pristine. Right out of a magazine. You’d think a realtor had set it up in preparation for selling the home. Either someone really loves this kitchen and maintains it constantly or it is never used.
“And this is where we’d cook, if anyone actually cared to try.”
Well, that answers that question. Guess I’ll have to put the old girl through her paces as I flex my chef muscles.
“Hol’ up. So, you have this whole kitchen and no one here cooks?”
“We’re just busy y’know. We usually order out most of the time.”
“Whew, you big city folk sho’ is weird.”
Shaking her head “Let me show you to your room.”
Kyle brushed past me as she headed towards the stairs we had passed. She placed her hand on my chest as she did so, and I can’t quite explain why but my heart fluttered. It caused me to pause. Kyle looking over her shoulder gave me a smile I hadn’t realized I’d been missing over these last few years.
“Grab your things please and we can continue the tour”
“Sure, sure,” I muttered, still lost in thought. Grabbing my bags from the foyer I followed Kyle down the second flight of stairs.
“Locking me away in the basement huh, really Harry Potter of you.”
“He was locked beneath the stairs, smart butt. This is more of a ‘Goonies’ situation”
“Baby Ruuth. Ruuuuth Baby.”
Kyle had to stop her tour. My impeccable Sloth impression having drawn out the cutest laugh I’d ever heard. Also, the most contagious, I couldn’t help but join in.
Once our laughter abated, I got a good look at the basement. I was expecting a cold dingy dark unfinished room more suited to storage. Instead, to the left of the stairs, I was greeted by a rather large sectional and an equally large TV to match.
“Ok, so who’s selling drugs? Because this seems way too nice. No offense of course.”
“You have BiBi to thank for all this, well BiBi’s parents actually. They used to live here before renting the place to us and they left a few things behind.” She gestured towards the oversized sectional.
“The tv as well? Noice.”
“No, that’s Athena’s. She says it’s a crime to watch sports on anything smaller than that monstrosity. It’s great for movie nights though. C’mon almost done.” Kyle did an about-face and headed towards the back of the apartment.
Kyle gestured off handily towards the bathroom directly across from the stairs. Peeking inside revealed it had a shower. There were several more doors further down the hallway. I was curious as to what they were. Maybe more rooms that would add to the awe I was already feeling. Kyle told me the ones to the left were the water heater and passed that laundry. At the complete end of the hall was the gym. Seems their roommate Athena had converted the storage space there to suit her means. My room however was just to the right of the stairs.
“And this is where you’ll be staying.” doing her best Vanna White Kyle gestured towards the door.
A smile already on my face I entered the room, my room. It was sparse containing nothing but a bed, fully dressed, and a wooden desk. Accordion doors on the right wall let me know they were hiding a closet. Checking out the closet I could see that my current wardrobe wouldn’t fill it. Not because the closet was large, but because I’ve thrown out more than I’d bought over the years. Something I was hoping to change now that I’d be making some “real” money.
“Not bad. I don’t think I said this yet but thank you for letting me stay here – I really appreciate it.”
Giving me a mockingly stern look Kyle said, “Well don’t thank me too much, you still gotta pay rent.”
Raising my hands in surrender “Yes, yes I know. So, what we doing cash, ass, or grass?”
“Venmo.”
Half turning, I poked out butt giving it a wiggle “You sure?”
Kyle’s face immediately turned bright pink. Her now flustered state made me double over in laughter. Kyle gave me a good fist to the shoulder. I’d call it a hit, but with as soft as it was, I think that would be rude to the word.
Finally regaining my composure, I answered “Venmo it is then.”
The color finally returning to her face, or should I say leaving, Kyle asked “Need any help unpacking?
“Naw, don’t really have much to unpack” demonstrating I lifted my duffle. Which I then turned to place on the floor next to the bed along with my backpack.
Kyle seemed taken aback. Her body tensed. The rejection caused her to recoil slightly from the response. She seemed lost as to how to continue the conversation that was so easily flowing before.
“Oh, well if you want to talk or just hang, I’ll be upstairs.” she shrugged, her voice now unsure.
My back to her now, I answered over my shoulder. “Yeah of course.”
“I left a towel and washcloth in the bathroom for you as well, so yeah, just umm let me know if there’s *anything* you want from me.” The emphasis was audible, I took it as Kyle just being polite. She was always so selfless. I really appreciated her doing this for me, but I didn’t want to burden her anymore tonight.
“Thanks, Kyle, I really do appreciate it.”
It was now my turn to initiate a hug. A small gesture of my gratitude for letting me stay. She returned the hug earnestly. In return, I was able to take in her lovely scent and feel her plush body against me one more time. This time my hands instinctively wrapped around her waist. Part of me wanted to just feel her skin, if only for a little bit. When my hands connected with the exposed flesh of her lower back, it sent electricity through my fingers and up my arms. Kyle’s body responded with a slight shake as her muscles tensed and relaxed into my hands. Staring down at her back gave me another eyeful of her delicious bottom. I wanted to reach out and fill my hands with its glory.
This, this wasn’t right though. I can’t do this. I need to stop. Get a hold of myself. She’s giving us a place to stay. I just need to go to sleep and take a breath.
I began to release Kyle. Disconnecting the energy flowing from my hands to her body. And placing them safely at my sides. Kyle followed me not long after. Blushing and fiddling with her braid.
“So…yep.”
“Yeah”
The silence between us was thick and awkward. I decided it was best to end it quick.
“I’m gonna head to bed, really tired after the trip y’know. I’ll see you tomorrow?”
Kyle looked…disappointed. No, hurt. Like a closed wound long forgotten had reopened.
“Yeah. Tomorrow.” quickly turning she left the room closing the door behind her.
Fuck.
I was too handsy, wasn’t I? She probably noticed me looking, no *leering,* at her tonight. What is wrong with me? C’mon, get it together, Darcy. You’ve got to keep it together; you live together now and she’s your friend, you should treat her better than that.
I should go upstairs and apologize.
I stood there unmoving.
Ok, tomorrow, definitely tomorrow. Unmoving.
Or I could just pretend it didn’t happen at all and let Future Darcy figure this out.
“Yep that’s it. Fuck future Darcy, this is his problem now. I’m going to bed.”
Stripping down to my boxers, I turn off the lights, let out a huge breath, and collapse on the bed.
Wow, even this mattress is better than my old one. “I must’ve done something right in a past life,” I thought. Even the sheets smelled amazing. Kyle must have just washed them. A real familiar scent, again floral, but a little different. I’d have to ask Kyle about it. I let out a large yawn, stretched, then let myself sink into the sheets. Quickly falling asleep.
****
There was a knock at my bedroom door. I could tell by the trepidation in the knock that it was Kyle, that and I’d been expecting her all day. On the floor of my childhood room, I sat slumped against my bed. Spending my last days before college doing nothing. I was midway through a *Streets of Rage Combat* match and couldn’t muster the will to stand.
“It’s open.”
“Hey, Darcy! It’s me.”
“Yeah, I could tell. You know you don’t have to knock.”
“But what if you’re…?” her voice trailed off eyeing the floor in discomfort.
“Cccccombo Breaker! Sorry, what’d you say?”
“It was nothing.” I could all but hear her blushing.
My match over I looked at Kyle for the first time. She had come out this past winter, just days after turning 18, and had been spending the summer growing into her true self. We had spent almost every day this summer together, but today something was different.
She was wearing a yellow floral sundress. It was modest, falling above the knee. No different than her usual style. Still growing her hair, it fell to her shoulders. Her dress accentuating her slim waist and wide hips on her feminine figure. I’m usually a breast man, but the way the fabric ran down Kyle’s legs made my blood rush and without a proper release, my lust was now kindling waiting for a spark. I was without a doubt pent up. Not having spent time alone or with any other girls since breaking up with my ex. Kyle’s questioning voice brought me out of my reverie before my lust could overcome me.
“Darcy…you okay?” She was blushing. Her hands wrung her dress nervously as a small smile started to spread across her face.
I was dumbstruck. She had caught me gawking at her. I had enough shame to avoid eye contact.
“Sorry. Kind of zoned out there. Did you want to fool – eh I mean, go a round?”
“What!?” she responded flustered.
“Streets of Rage Combat.” I motioned towards the screen.
“Heck yeah. Don’t cry when I spank you.”
“You wish, grab the sticks.”
We played round after round. Talking smack during the matches and idly between. As the afternoon faded into evening, the space between us went from feet to inches. Inches then turned to the flesh of our thighs pressed together. Her skin was smooth and soft. Not a blemish on her fair skin. I started to notice the perfume she was wearing. It was floral but muted. A perfect match for Kyle’s personality. To truly appreciate the subtleness of their beauty you had to take the time and devote yourself to the task. Something I seemed to be doing more of lately. I stole a glance at her now crossed legs unable to ignore them any longer. Her relaxed position caused her dress to rise slightly. My body did the same now taking notice of the feminine form now pressed against me.
“Combo breaker!”
“Wait, what?”
“That’s what, like, 40 to 5. Where’s your mind at Darcy?”
“You distracted me.”
“How?”
“Your perfume got in my eyes and you’re practically sitting in my lap.”
“Perfume in your eyes? I’m not even wearing perfume. Also, this,” she motioned to our seating arrangement, “is not in your lap.” Rising to her knees she stepped over me with her right leg straddling me before planting herself in my lap. Giggling as she did so, “Now this, this is in your lap.”
I playfully grabbed her hips fully intending to push her off. Only for her to further press the weight of herself down, refusing to be moved. The newly added pressure doing nothing to abate my ever-growing erection.
“Ha! You’re going to have to try harder than that,” laughing and taunting as she refused.
I planted my feet on the floor in preparation of throwing the now gloating Kyle off of me. In anticipation of me bucking her off Kyle looped her arms around my neck and wrapped her legs around my waist, firmly attaching herself to me.
My first attempt to thrust her off my lap caused Kyle to pull into my chest placing her head on my shoulder. The second caused her to let out a girlish squeak in my ear. When I pressed forward with my hips again, I was greeted by a soft moan, only muffled by Kyle now pressing her face deeper into my shoulder. The sound added heat to an already growing wildfire that was fighting to be unleashed.
I decided to switch up my tactics now, ignoring the growing heat I was feeling inside. Grabbing both of Kyle’s legs right above the knee. Kyle was notoriously ticklish, so I began with one goal in mind, her complete surrender to me. Her skin was even softer to the touch, but I couldn’t allow myself to get distracted now. I needed to put Kyle in her place and show her who was really in charge here.
I put on my sternest impression, “I’m only going to warn you this one-time Kyle, get up now or I’m going to have to discipline you.”
In almost a whisper, she defiantly responded, “I dare you.”
I lowered my head towards her ear, “Remember, you asked for this.”
Kyle then nuzzled even more into my body, if that was even possible. She was practically molded to me at this point. Her scent was the only thing I could smell, it was slowly but surely having what I assumed was its desired effect on me.
Warning given; I began to mercilessly tickle Kyle. A torrent of giggling was unleashed from the beauty on top of me. Her laughing caused her hips to buck and sway. Her soft body giving me the most pleasant sensations.
“Do you give up?”
Barely able to speak through her laughing all Kyle got out was, “No, please…” before I drove my hands further up her leg, pressing her dress aside, attacking her more pliant flesh.
“Do you give up now?”
“Yes sir, I give up.”
Releasing my grip on Kyle’s thighs, I gather my will to respond, “I’m sorry, I couldn’t…Kyle what are you…”
Her giggles now moans. The movement of her waist and hips slowed. No longer erratic but purposeful and rhythmic.
She tilted her head and brought her lips to my ear. “I said, ‘I give up.’ I’ll get you off. I mean off you…I’ll get off you. *If* that’s what you want.” Her tone was submissive, but her body was still rocking back and forth in my lap.
The emphasis on the ‘IF’ showed me that there was an opportunity here. Opportunity for something more. Something that my mind had been battling with as Kyle and I spent more time together. There was no denying I was growing more attracted to her day by day. The only thing holding me back was myself. I could feel that Kyle was aroused as I was. A firmness between her creamy thighs betraying the womanly figure atop me.
Then Kyle ran her fingers slowly over the back of my neck. She knew exactly what she was doing. She’d been there as past girlfriends used this trick to get me to do what they wanted. It always worked and today was no different.
My burning fire, no longer able to be contained. I begin groping Kyle’s thighs with a hunger. There were no words needed. She had sparked my lust and I intended to use her body to suffocate the flames. I had decided no part of her luscious legs would go untouched. My insatiable groping evoking moans and girlish squeals from Kyle was all the encouragement I needed.
Having my fill of her thighs, my hands searched for more flesh to molest. New land on this unexplored body that my hands could grip for leverage to tip us over the edge of lust.
As if reading my mind Kyle moaned in my ear, “You can grab my ass if you like.”
An invitation I took immediate and complete advantage of. Her ass was just as soft and giving as her thighs. Her panties were cotton and the thought of tearing them off and taking her began to form in my mind. Hungry for more, I slid my hands beneath the thin layer of fabric keeping me from the delicious flesh that lay beneath. That seemed to be exactly what Kyle needed. She began grinding my erect member more fervently than before. Just as starved as I was for a climactic end.
“Please,” she moaned, “I want you to finish. I need you to finish.”
I let out an acknowledging grunt. Redoubling my efforts to find release using Kyle’s body as a means to an end. Getting close I found myself either unable or unwilling to keep my eyes open. My head drew back while Kyle’s breath danced on my neck as she searched for an answer to her lust.
“Kyle, I-I’m going to cu-” all at once, I could feel the heat of my impending orgasm. It was as intense as it was quick. My hands dug into Kyle’s poor little rear as I desperately pumped my hips searching for just one last hint of pleasure. Lost in my desperation, I couldn’t notice Kyle in hers.
$$$$
Kyle had been on edge since she had arrived. She’d declared this morning that today would be the day. She would finally thank Darcy for being there for her and she intended to show him how thankful she was. She had planned it out perfectly. She’d chosen the dress after catching Darcy eyeing other women in similar fashions. The perfume, a favorite of his that he’d commented on in the past. Those coupled with knowing Darcy was still getting over a breakup and having not found release as of late came together to create the perfect plan.
Once Darcy had finally given in to his lust, she devoted herself to seeing him to his end. She was unwilling to finish before the man that had made her feel like a real girl. He deserved that much at the least.
What she hadn’t planned for was the pleasure she’d get from having her body used by Darcy. His grip on her ass, the feel of his big black penis dwarfing her girly cock, the sheer fact that he was using her to satiate his lust was too much for her to handle.
“It’s happening, it’s finally happening,” Kyle moaned into Darcy’s neck. She had been refusing to let herself finish for weeks, waiting for a real man, for Darcy, to give her permission. Until the day he made her submit and she could hold it no longer.
“I’m so close. Oh, Darcy! Please, please, please tell me I can cum!” She begged, longing for her unknowing master’s permission.
****
My mind was spinning. I hadn’t realized how pent up I was. Kyle was breathing heavily in my ear, saying something I couldn’t make out. My lustful flame now thoroughly doused by the still-warm seed now staining my shorts. Slowly releasing my grip on Kyle, I started to realize what I just did, and who I’d done it with. I panicked.
In alarm, I pulled back. “Oh crap! Kyle, I’m so sorry. I completely lost control.”
Kyle’s grinding slowed, then stopped as she leaned and looked at me for the first time since this all started. I could tell from the look on her face she was surprised by the change in my tone.
“It’s okay, Darcy. I liked it.” She was trying to be reassuring, mimicking the same tone I’d been using with her the past few weeks. She gently placed her hand on my cheek, her thumb brushing my lips as she began to lean in. I knew what we had done wasn’t wrong, but the feeling of Kyle’s still hard cock pressed against my flagging staff forced my brain to make some quick decisions about who I thought I was and what had occurred.
It was then, with me and Kyle moments from sharing our first kiss, that the worst thing I could say fell out of my mouth.
“I’M NOT GAY!”
Kyle stopped.
Pulling back Kyle began searching my face, looking for what? I don’t know. I do know that whatever it was she never found it.
“I mean, I like girls. Like I know you’re a girl but-” I stopped.
“No, Yeah. I get it.” I could hear it in her voice. I could see it on her now downturned face. Her slumped shoulders making her feelings evident.
I had struck a blow capable of bringing one of my closest friends to the brink of tears. Now in a tailspin, against my better judgment, my teenage self-continued to speak.
“It’s just- I just like you as a friend, you know.” I was a fucking idiot.
“Yeah, I get it-” I’d heard Kyle speak meekly before, but she never seemed so hopelessly deflated. Standing, she flattened her ruffled dress, gathering herself and any dignity she had left. “It was my fault.”
“No, I-it was just a lot for me. You understand?” I asked, hoping for some form of empathy. An olive branch to let me know our friendship was still intact. I stayed seated. Afraid to stand and show the physical evidence of the pleasure I took from Kyle’s body. Unwilling to confront the weight of my words and actions.
“I-I’m going to h-head home Darcy. It’s getting pretty late.” I could hear her holding back the tears now. The sound caused my heart to lurch in my chest, but still, I did not stand. I sat there, feeling less of a man than ever before.
“Yeah, yeah. So, I’ll see you tomorrow, right? Movies?” My voice was more hopeful than it had any right to be.
“Yeah.” She looked back at me one last time.
“Tomorrow.”
Then she closed the door. Leaving me in the ashes of my lust, smoldering with regret.
$$$$
I had to get out of Darcy’s room as quickly as possible. I practically ran, didn’t even say goodnight. His first night in town and I’m already acting like an idiot. I was upset, confused, and even worse, horny. I was unprepared for Darcy’s rejection. It seemed like he was *enjoying* himself.
Maybe I should go back in.
Maybe Talk to him.
Maybe Hug him again.
Even.
Kiss?
No, stop.
Just, let’s go sit.
Dragging myself to the top of the stairs I headed straight to my favorite seat. My old couch in the living room. Walking over I plopped down on the worn black sofa. letting myself sink into the soft fabric of the cushions. Finding comfort in their fluffy embrace. My body was now starting to relax, but I could feel my mind refusing to stop.
I don’t know what I expected. Of course, he wasn’t interested, why would he be? Asking Darcy to move in was a bad idea, but he’s here now. what am I going to do?
Get a hold of yourself Kyle you’re a big girl. You’re not the same person you were then, you can do this. Should I do this? I mean, you can’t force someone to like you…can you?
A melodic voice brought a pause to my thoughts “Well I don’t think I’ve seen you this distress since your orchid died, Sunflower”
It was BiBi. If her songbird voice didn’t give her away the use of her trademark nickname for me did. BiBi was somewhat of a big sister to me, if you had incestuous thoughts about your sister that is. I always found her so alluring. She had a petite body and was even shorter than me standing at 5’3″. I was ashamed to admit it, but her honey hued skin and hazel eyes played upon my fetish for melanated skin. Her chest may have been flat, but her Latin heritage blessed her with a great bubble butt. Everything BiBi did dripped with sex. Walking, talking, even brushing her hair out of her face. I’d be lying if I said I never masturbated to the thought her.
Turning to look at her my interest was immediately peaked. She was standing at the bottom of the stairs dressed up as a schoolgirl. Complete with a white blouse filled out by her largest breast forms, a short skirt, and white knee socks. Her makeup and neon pink wig made her look like an anime character. I’d seen this look before; it was one of my favorites only second to her alt-punk rock costume. She must have just finished a show. She was covered in a light layer of perspiration giving her a post orgasm glow.
“Hey, Yeah I just have a lot on my mind”
“Did your new *boy toy* not show” her emphasis dripping with implications.
“He’s here and *please* stop calling him my *boy toy*. We’re just friends.”
“Oh, so he didn’t jump your bones as soon as he saw you then hmm?” the lust in her tone was both arousing and embarrassing
I could feel the blood rushing to my face as I spoke. “What!?…no it’s not like that?” my voice began to shrink. Chagrined n at the fact that that was exactly what I was hoping for.
“Aww, I’m messing with you Sunflower.”
I fell over onto the couch. Burying my face in a nearby throw pillow. Muffled I responded, “I’d rather you not.”
BiBi glided over. As graceful as ever and sat down beside me.
“Be honest, you want to be more than just friends, right?” Bibi’s tone was now that of the caring older sister. I always loved how she could so easily transition between the two.
I found it hard to meet B’s appraising gaze. I decided it just be best if I keep my head in the pillow and respond
“I mean, I wouldn’t say no to it. It’s just, he’s not really into girls like us.”
“And you’re hoping he’s changed his mind in the past several years, right?”
I sighed into the pillow “Right.”
“That’s either the boldest thing I’ve ever heard or the dumbest” she posed.
“Thanks for your vote of confidence”
“Look it’s simple, the key to a man’s heart is through his penis”
I paused, shocked. I looked back over my shoulder in surprise. “What!”
“I’m serious. I’ve bagged plenty of “straight” guys. Trust me once the blood’s flowing, they’ll be begging for it.” The confidence in her voice let me know she wasn’t joking. That and I’ve seen some of these supposedly straight guys doing the walk of shame in the morning.
BiBi shifted, turning her body towards mine, then moved over me. Placing either hand to the side of my head, her legs straddling me, her crotch pressing lightly against my butt. BiBi had gone from big sister to temptress once again. She loved to tease me as much as taking care of me.
Lowering her lips to my ear she whispered “If you’d like I could break him in for you. You know I have a way with men who he claims to only like ‘girls’.”
I could feel BiBi’s hardening penis as it was pressed between my cheeks. Letting me know the idea of “breaking in” another straight guy excited her. If I was honest with myself, I’d say the idea wasn’t completely unappealing. I could imagine it now. BiBi slinking into Darcy’s room, probably wearing some sheer negligee. She’d crawl onto the bed, her little frame barely waking him. She’d slowly pull the covers back revealing his thick penis. Her little hands would look so tiny gripping it, stroking it. She’d wrap her full lips around the head. The warmth and wetness of her mouth finishing the job of bringing his throbbing cock to attention.
My body began to betray me. I could feel myself pressing back into Bibi’s shaft and a moan escaped my lips.
“I’d take that as a yes?” She purred, nestled even closer to my ear than before.
“I, um, thanks but…maybe later?” regaining my composure I began to move towards sitting up, lest I find myself grinding more into BiBi.
She was slow to move, obviously enjoying the feeling of me backing into her more as I changed positions.
“M’kay. Don’t worry yourself too much though, if he’s smart, he’ll come around.”
Now sitting up I bit my lip. The worry quite obvious on my face.
“He is smart right?”
“Yeah, just a little *unaware* at times.” That was an understatement. If you only hinted at the sky being blue, he’d never figure out what color it was.
She placed her hand on mine. Holding it in a show of support. Shaking her head while saying “Good luck sis. And don’t forget my offer still stands.” Winking as she got up and continued towards the kitchen, only to return a second later with a Gatorade. Before heading upstairs, she gave me a sultry appraisal. Licking her full lips as she did so. The whole display left my face redder than before and unable to meet her gaze as she left out of sight.
Alone again.
Just me and my thoughts.
Well, poop. Darcy definitely sucks at picking up hints. I mean look at how I dressed tonight. Did he really not notice me? No bra, these tiny panties riding up my butt and my thinnest shirt and shorts. I’m practically naked!
Maybe I should take some of BiBi’s advice.
I could go downstairs right now, crawl into bed with him in just my cute, albeit uncomfortable, little panties and give him a blow job.
What guy could turn that down?
No guy that’s who.
That’s right! I’m just going to get up, go down there and suck his dick.
I mean, he wouldn’t say no, right?
My mind began to race then.
But what if he doesn’t actually think I’m cute I’ve put on a little weight so he might be turned off if I show up naked but if I’m fully clothed would that be weird am I good at blowjobs my last boyfriend didn’t complain but he never finished either would it be so bad for BiBi to “break him in” why does the thought of watching that turn me on oh God am I a cuckold would they even let me watch wait am I really considering this no yes no maybe BiBi is hot Darcy’s hot too it be no different than porn but what if he doesn’t want me after I could join in during “once the bloods rushing” right will that work God this is hot why is this so hot I need to cum no I shouldn’t I said I would save it for Darcy a nice big load just for him to show how much I wanted him that I saved myself for him I wouldn’t even last if he entered my hell I almost came from hugging him fuck the way he grabbed me I should’ve gotten on my knees right there and let him use me my hands my throat my ass it wouldn’t matter as long as he was happy as long as he came and I helped in some way I’d be happy.
I was breathing hard now. My mind unstopping. Heart pounding in my chest. Thong straining against what seemed like the hardest I’ve ever gotten.
I think I need a shower, a very, very cold shower.
Source: reddit.com/r/eroticliterature/comments/hvbrfx/darcys_doubts_day_1_mt