The Best Night I'll Ever Regret

I heard the 'bzz bzz' of a text alert in my cupholder as I pulled into the driveway. I put the car into park and checked my phone. I would like to say the extra attention to not checking my phone while at the wheel was a normal habit. However, it was more out of an over-abundance of caution that came with driving my parent's expensive Jeep.

I looked at the text, from my older sister Megan. *Hey Mol. Logan is on his way. Says it should be like 5 hours.* I pocketed my phone, grabbed my backpack and headed for the house.

Megan's text referenced her husband making the roughly 5 hour drive to my little rental with my car. The plan was for Logan to drop it off here and drive my parent's jeep back to where he and my sister lived.

I didn't have my car because, of course, the week before I made my move south for grad school, the old thing decided it had been too long since it'd spent time in the shop. My parents had been kind enough to lend me the jeep to get myself around until my car was fixed up.

I'd enjoyed my couple weeks of luxury, but I was ready to be back in my more modest sedan. It would be nice to comfortably stomach parking next to the other cars in the always packed school lots.

I felt another 'bzz bzz' from my phone as I walked up to my door. The message would have to wait as my roommate's grey tabby cat tried to make her daily break for the outside world. I shuffled inside, herding her back with my feet. Her defeated 'meow' made me chuckle as I closed the door.

I set my backpack down on the one piece of communal furniture, a past its heyday couch, and walked into the kitchen area. I poured myself a glass of water, desperate for a respite from the late summer Southern heat.

"Hey Molly! How was class?" I heard from one of the two other rooms in the house. My roommate Haley walked out into the living area to hear my answer in person.

"It was good, only the second week still, so we've only really started diving into stuff" I looked up from filling my glass and almost dropped it immediately. Haley was barely wearing any clothes, something that I was starting to realize was pretty much the norm for her.

Haley was a nurse at one of the larger hospitals in the city and a couple years my senior. Her roommate before me had just recently moved out after getting married. Conveniently, opening up a room in a perfect location as I started graduate school.

Haley and I had met for coffee one day, making sure the other wasn't an axe murderer and all that, and became fast friends. As fun as she was to talk with, I was still becoming accustomed to some of her idiosyncrasies.

One of which, as I mentioned, was her seeming disdain for clothes. Today she was clad in only a white thong and matching sports bra. The Calvin Klein name band on both added a degree of classiness to her otherwise, exceedingly, simple outfit.

Paying no mind to my surprise, Haley turned to pet her cat, who had jumped up to sniff my backpack on the couch. I took in the scene, noting the white of her underwear offered an aesthetically pleasing contrast to her deep coffee colored skin. A delighted purr emanated from the cat as Haley paid her attention.

My initial shock wore off and I drank my water without further incident. Truthfully, I didn't mind Haley's penchant for being scantily clad. I had been a soccer player for my school during undergrad and was more than used to being around women in the buff.

In fairness to Haley as well, if I had her body, I might very well dress the same. She had the impressive backside stereotypically associated with women of her skin tone. Not to mention, a set of breasts that were every bit as eye catching.

Impossibly, she maintained a slim and toned stomach that rivaled even a former collegiate soccer player such as myself. She adorned it with a sparkling belly button stud.

"Just reminding you, my brother-in-law is gonna come through this evening to trade out cars. Up to you if you want to make a wardrobe change," I playfully ribbed her revealing attire.

She laughed, flashing a stunning and electric smile that lit up her whole face and wittily responded, "Probably won't. You've shown me his picture, I'd be more than happy to let him have a look at all this!" She gestured to her ample assets while doing a little curtsy, her dark chocolate eyes twinkling with mischief.

I laughed as well. I hadn't necessarily shown Haley a picture of Logan. However, he was in some full family shots I'd put up for decoration. He had a habit for standing out from the crowd in pictures.

"Be nice now. I'd never live it down if MY roommate was guilty of stealing my sister's man!" That got a belly laugh from Haley and startled her cat into meowing angrily at us both for making so much noise.

A phone ringtone blared from Haley's room causing her to excuse herself. Grabbing my backpack, I followed down the hallway to my own room.

The home featured a connected living and kitchen area. The lone hallway ended with two bedrooms, one on each side. Each bedroom came equipped with its own full bathroom. The perfect setup for two mid 20s women.

Another 'bzz bzz' from my pocket pulled my attention back to my phone as I set my backpack down and sat at my desk chair. Touching my phone screen, I saw I now had two notifications from my fiancé Dave.

*How'd classes go baby!?* read the first one. The second, most recent one said, *When does Logan get in?*. I rolled my eyes a little at the latter text. It had initially been Dave who was supposed to be bringing my car down.

Unlike my brother-in-law, he lived in the same city as my parents and naturally, I would enjoy a visit more from my own fiancé than from my sister's husband. However, Dave had backed out of being the car courier at the last second due to his parents scheduling a spur of the moment lake trip that he wanted to join in on.

I lay down on my bed with an exasperated sigh. I wasn't mad at Dave necessarily. A weekend at the lake sounded really nice right now. However, a weekend with his fiancée should've sounded way better!

Electing not to respond immediately, rather than sending a snappy reply, I tossed my phone over to the side of my bed. It landed on a skimpy red piece of lingerie that may have even made Haley blush. I'd bought it in preparation for Dave's visit south and seeing it again only further annoyed me.

Lying in bed and staring at my ceiling led me to feel drowsier and drowsier. Before I knew it, I was drifting off into a nice little nap.

'BRING, BRING, BRING' the sound of my ringtone brought me back to the waking world. Groggily, I rolled over and answered it without even looking at the caller id.

"Hello?" I yawned into the microphone.

"Hey Molly. Sorry, did I wake you up?" I recognized Logan's voice on the other end. Was he here already? I looked over at the clock on the wall and did some quick math. No, it had only been about 2 hours since I fell asleep. A heck of a nap, but Logan should still be on the road.

"No! I mean yes, you did, but it's no biggie. I shouldn't be sleeping the day away." I started to wipe the sleep from my eyes trying to stay true to my words.

Logan chuckled on the other end. "Okay, well I just wanted to let you know I'm going to be a little later than we initially planned. Looks like there was a wreck somewhere in front of me and I'm parked in an impressive line of cars."

I groaned in solidarity. "Ooof. That sucks. I'm sorry, should you just turn around?"

"No, I'm already a little over halfway and honestly, I'm stuck here regardless which direction I go"

I started to say something before he interrupted me quickly. "Oh, shoot my bad, was that you asking me to turn around? I don't want to hem up any plans you might have had. I know its Friday night."

I laughed out loud at that. "No, no plans for me. Unless you count Netflix and boxed mac n cheese as plans."

That made him laugh too. "Who are you kidding? That sounds like an excellent evening! I'll try not to interrupt it too much. It looks like we might be moving a little bit here. I'll keep you posted if I have more updates!"

"Alright, thanks for letting me know Logan! See you in a bit!" we hung up the phone and I decided to get up. I had some more time to play with now, so I looked around and contemplated what I should do.

My eyes found my backpack, we were so early in the semester that there wasn't really anything I needed to study yet. I continued scanning over my room until I saw a pair of athletic shorts. A workout sounded like the right thing to do.

I centered myself in the closet mirror and eyed my 5'5" frame as I began to peel off my school clothes. I'd worn denim shorts. A little more chaste than what I might wear on a night out, but still quite flattering. I have an impressive ass if I can say so myself, so doesn't really take much for my bottoms to be flattering. They just need to be at least somewhat tight.

I adjusted the waistband of the lacy pink thong I'd worn underneath today. I turned from side to side examining the profile of my prodigious rear and how it fed into a set of impressively defined legs. I couldn't help, but sport a self-satisfied smile. Years of athletics and the exercise that went with that had done me well.

I did a 180 for the mirror's benefit. I peered back over my shoulder, giving my rounded, heart shaped butt a loving jiggle. "Fuck, you can barely see my thong in my ass," I giggled under my breath.

Some of that may have been the color choice for the day. The light pink of my underwear didn't particularly distinguish itself from the rosy skin tone that came with being a natural redhead. The lack of a white tan line to help the color pop indicated what my typical choice of swimwear looked like.

I peeled off the simple green tank top and I turned back to face the mirror. The brutish heat paired with pride in my fairly toned arms had influenced the tank top decision. I rubbed my hand on my flat stomach with satisfaction as I revealed it to the mirror.

In my college athlete days, you would have been able to count 6 abs in my reflection. I wasn't quite so defined as I had been, but I would likely still be the most toned in a group of girls. My hands travelled up to my breasts unclasping my plain grey bra.

They weren't the most impressive set of boobs ever. As much as the running and lifting had helped my lower half, it had probably been somewhat of a detriment in the tit department.

I spread my fingers out, coming up just short of completely covering my full breast. I extended my hands out to where I imagined Haley's cannons ended. I couldn't help but snort a little to myself.

"How does she even move with tits that big?" I wondered aloud. Of course, I was a little jealous of her, but my chest never got any complaints. Most men had been lost in my ass, but plenty of attention was paid up top too.

Part of that was for my insanely sensitive nipples. I'd heard stories of girls who could orgasm just through nipple play, and though I'd never done it, I could definitely see where that might happen. My little routine for the mirror had already elicited a strong response.

My nipples were rock hard and a light pink color, only slightly more tinged than my strawberry blonde hair. There wasn't much contrast between them and the pale white of my breasts. My tan lines were a little more pronounced here. I wasn't quite as liberal with my swimsuit tops as I could be accused of being with the bottoms.

I bit my lip and pinched both nipples, sending a fluttering current down past my navel and between my legs. I wasn't on edge yet, but some blood flow from a hard workout and I was going to need to dig past the panties in my drawer for my vibrator.

Making eye contact with myself I continued my absentminded touching. My bright green eyes popped out from my reddish tan face. As a natural redhead, I didn't get as tan as my brunette sister. My skin did darken a little though, taking on a warm reddish hue that contrasted nicely with the lightening of my hair from the sun.

Shaking myself from my reverie, I tossed my hair back and stretched for the ceiling. My hair landed just past my shoulders, bouncing with some nice curls. I'd never been the curliest haired girl, but the southern humidity of my new home was helping to add some nice volume to it.

I pulled it back into a ponytail and leaned into the mirror to examine my cheeks and chin for any signs of zits. A habit I'd still yet to drop from my acne filled middle school years. I stepped back examining the angles of my face in the mirror.

It wasn't as thin as it had used to been during my fittest days of soccer. However, that wasn't a bad thing. I liked that my angular cheeks had filled out somewhat. I burst into a smile, overly pleased and somewhat sentimental at the idea that I was a woman happy in her own skin. A much too rare occurrence in the world.

Feeling confident in my body, and a little horny. I decided to eschew the athletic shorts. Instead, I went with a pair of blue spandex workout shorts. I had a black yoga thong that I traded out for the pink one I had on earlier. A matching blue colored sports bra followed. Feeling like showing off, I went for a baggy crop top.

I winked at myself in the mirror, because DAMN, I looked hot. Grabbing my phone, I opened up snapchat and quickly sent a photo in a flattering pose to Dave. I wanted him to know what he was missing out on!

I gathered my essentials and made my way out my bedroom door. "I'm going to go get a workout in!" I called over my shoulder to Haley's room on my way into the living room.

"Damn, no need to yell girl. You already had my attention!" Haley responded from in the kitchen as I walked by. I turned to see her gesturing to my body with one hand.

We both laughed as she gave me a catcall whistle and I opened our door to the thick, late summer air. I climbed into the jeep, ready to take it on one last trip before getting my car back.

Haley had recommended this gym to me when I first mentioned looking for one. It was right on her way home from the hospital. Since she'd been going for a while, she'd become pretty good friends with the owner.

This friendship gave birth to the 'Friend of Haley' membership discount which I happily took advantage of. Even if the 15-20 minute drive was a little longer than some other options.

When I arrived, it was quickly evident I pretty much had the run of the place to myself. My workout was uneventful, although I did catch the boy at the front desk peeking a couple times. I was feeling a little frisky, so I didn't really mind. Plus, he was kinda cute.

A little over an hour after I'd arrived, I finished up and exited the building. Not before giving the front desk a charming smile and one last cheeky bend over. I had to 'tie my shoes'. I chuckled inwardly as I made my way to the car.

I shook my head at my antics. I didn't always like the uninvited stares men give women at the gym, but today it just made me feel even hotter. Sitting in my car, I checked my phone. There was a text from my sister and a snapchat from Dave.

I opened the text first. *Hey give me a call when you can!* I immediately found her number and waited as the phone rang on the other end.

"Hey Mol!" I heard my sister Megan say on the other end.

"Whats up? You asked me to call?" I answered back.

"I did! Wasn't sure if Logan had got back to you. He mentioned he'd called you earlier. He said he was out of the traffic and he should be getting to your place at like 8-8:30." I glanced at the clock on the dash and noted it was a little after 4 now.

"Okay! No, he didn't. Thanks for the update!" that sucked for him I thought to myself, he was going to be driving well into the early hours of the morning.

"Don't thank me yet. I have a request for you too. Since it's going to be so late, would it be okay if he stayed the night at your place and drove back in the morning. I don't really think it's smart for him to be out driving until like 2 AM."

"Okay geeze MOM," I playfully made fun of her for her concern, "I'd have to check with Haley, but I'm sure that would be fine!" I kicked myself a little for not thinking to offer that myself.

"Thanks, Mol! I promise he won't be a problem and he will be out the door before you know it in the morning."

"Megan, relax. He's a grown man and I've stayed in the same house with him before. I know he will be fine." I laughed at my sister's expense.

"I know, I know! I just didn't want to put you out. I'm sure you had Friday night plans!" Megan tried to defend herself. I laughed again out loud. What was with those two and thinking I was this social butterfly.

"I'm going to tell you the same thing I told Logan. Unless, Netflix and some mac n cheese count as plans, I'm free for the evening!"

I referred back to the same joke I'd told Logan earlier. If, I kept bringing this up, I really was going to have to eat some mac n cheese for dinner. My stomach rumbled at the thought.

"You and I both know that sounds like an incredible evening." Megan laughed into the phone. I heard some loud barking on the other end of the phone. "Sorry, the dog thinks the squirrels in the yard are going to attack us. I'm gonna have to let you go. Thanks again, I'll have Logan call you when he's close. Love ya!"

"Love you too!" I snuck in just before she hung up the phone to attend to the dog. I quickly texted Haley to make sure it was alright if Logan stayed the night at our place. Her immediate heart eyed emoji response seemed to indicate this was an agreeable arrangement.

I decided to stop at the grocery store on my way home. All my mac n cheese talk had me craving. I pulled into the driveway next to Haley's car a little after 5. A 'bzz bzz' from my phone in the cupholder caught my attention before I got out.

It was Dave again, *Are you ignoring me?* followed by a little crying face. I lightly chided myself for neglecting to message him back earlier. I navigated to snapchat to see what he had sent me.

I opened the photo message and immediately a familiar cock filled my phone screen. Captioned with 'Look at what you did to me!'. I bit my lip a little. Dave was still somewhat in the doghouse for choosing the lake over me, but my workout had only added to my horniness from earlier.

Dave's cock wasn't the biggest I'd ever seen, but not the smallest either. He was probably right about average. I was no expert, having only seen 4 of them in action, but I'd heard average was between 5 and 6 inches.

We'd never got out the tape measure, but that's right in the range I'd have guessed for him. It was probably about average in thickness as well. I could wrap my thumb and middle finger around it with a little bit to spare.

All in all, a perfectly reasonable cock to have for the rest of my life, plus he was more than willing to make up for his lack of exceptional equipment with an enthusiastic and talented tongue.

Gazing at my fiancé's hard cock on my phone screen, I found myself squirming a little, imagining him going down on me. I exited out of the app and went to text him back.

*Of course not babe! In fact I'm about to go think about that snap you just sent me for a while.* I emphasized the message with a mischievous grin emoji. I collected my things from the jeep, including my newly purchased mac n cheese and made my way into the house.

I set my dinner on the counter and made my way into my room. I had a personal matter to attend to before I could focus on eating. I closed the door behind me and quickly dug into my panty drawer for my vibrator.

Grabbing it, I wasted no time stripping naked and climbed onto my bed. I kept my phone next to me in hopes Dave would text back and we could exchange some sexy banter to give me more inspiration.

Nothing came through immediately, so I resolved to go it alone. My vibrator was a simple one. Only 4 or 5 inches long. It had an egg-shaped vibrating head attached to the cylindrical handle. When I was feeling especially frisky, I'd push the head into myself, but generally I just kept it positioned on my clit until the fireworks ended.