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Old Friends, New Lovers Ch. 01

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I was born when my brother, Luke, was six, so there was always a gap between us in everything we did. We were distant enough for years that by the time we started having mutual interests, it was awkward to share with each other. When Luke entered high school, he made friends with Simon. They were inseparable. For a while I was jealous that this new person could so easily make a connection with someone I had lived with my entire life. I was angry at them both, and being younger, it was pretty obvious.

Simon took notice to my behaviors. Instead of harassing or poking fun at me like any other teenage boy would do to his friend’s kid sister, he would invite or try to include me in whatever they were doing. I didn’t accept at first, thinking it was all a big joke. After some time, however, I noticed he was genuine in his attempts to reach out. Once I swallowed my pride and accepted his invitations, a new world opened up. We three became thick as thieves, and it felt like Simon belonged with Luke and I.

Over the years Simon became just as much of a friend to me as he was to Luke. We stayed active in each other’s lives throughout school and college, and eventually turning to social media to keep in contact when we three would move away to follow our adult lives.

I now work for a digital marketing company that handles clients throughout the States. Part of my job is traveling to meet with clients to discuss their wants and needs for the projects they have commissioned. We go over the details, I stay for a few days to work on basic concepts, present the rough drafts and fly back when we have the groundwork sorted. I don’t keep a regular work schedule due to the nature of the job and the demand of the clients, so finding time for myself, friends, etc can be a challenge. That’s why when I learned my next destination would land me in the same city as Simon, I was ecstatic! The last time we saw each other was about four years previous when I was graduating from college.

Right after confirming my itinerary, I messaged Simon:

“Hey there! I wanted to let you know work is bringing me to your neck of the woods next week. Are you free to hang out? I’ll be flying in and have reservations with Oak Ridge.”

My phone alerted within a couple minutes:

“Lynn! That sounds wonderful. I haven’t seen you in ages. I would love to pick you up and get you settled in. If your hotel doesn’t work out, you can always stay with me, give us more time to catch up and hang out. Give me the details of your flight and I can’t wait to see you!”

I squealed with joy after I sent over my travel information. The next week could not come soon enough!


My luggage finally made its way around the carousel track. Picking up my suitcase, I made my way towards the arrivals pick up. The strip was pretty empty, so picking out the right car was easy. I hurried towards it. The trunk popped open and the driver’s side door opened. There he was! Oh it was too long since we last saw each other.

“Lynn!” He greeted ecstatically.

“Simon!” I dropped my bags and ran in for a hug. He was only an inch or two taller than my 5’7″, so our hot cheeks pressed against each others, his stubble poking just a bit.

We parted and took each other in, updating our images of each other from the years of separation. He was handsomely bald, eyes tired from too many hours at a computer, average build, wearing cargo pants and t shirt. I had my long brown hair in a loose ponytail, a few cute pieces of jewelry, and a flowery summer dress on for comfort. The dress, admittedly, was really great at showing off my large breasts, cinching in at my smaller waist, and accentuating my big hips and thighs.

“Well” Simon whistled after a thorough look-see. “Post college agrees with you! I can hardly believe this young woman is Lil Lynn.”

“Aw, you always know how to make a girl feel nice.” I giggled. “What say you take me to that coffee shop you’re always raving about? I need a little pick-me-up before I check in.”

With a quick salute and a click of his heels, Simon grabbed my bags and stowed them in the trunk. He was always a goof, though I feel that side of him would keep him young for many years. I climbed into the passenger seat. Simon slid in, started the car and we set off.

We chatted merrily in the car as we made our way downtown. As we turned a corner, I spotted a cute sign with a smiling mug over the door to a corner coffee shop. Simon parked right outside the door, and we walked in the cafe, the intense yet soothing smell of coffee mixed with warm milk welcoming us. Our coffees ordered, table secured and basic catch up already cleared, we began to really talk.

“Now, what brings you to town?” Simon asked.

“There’s a client here I’m meeting tomorrow. We’re anadolu yakası escort going over what their company wants for designs for logos, merchandise, business cards, your basic set up. I’ll be here through the week since it’s a larger project.” The barista came with our coffees.

Simon added some sweetener to his. “Well, I’m a little sad you kept your hotel reservation. It would have been fun to have a week long sleepover” He winked.

I don’t know why I blushed then, but I did. There was a short time during my senior year in high school and my freshman year of college that I had a bit of a crush on him, but I had resolved those feelings to the allure of the “older brother’s friend” attraction. I took a sip of my latte to hide my cheeks.

“Ha, that would be fun. I probably wouldn’t get anything done if I stayed with you, though.”

He sighed, “You say that like it’s a bad thing.”

“Hmm… Sounds like you’re just feeling lonely.” We were getting into one of our teasing moods like the good old days.

“Excuse me for wanting to keep the attention of a beautiful young woman during such borrowed time.” Simon took one of my hands in his, giving me a shit-eating grin. Oh he really was in a mood. I needed to call his bluff.

I moved my chair closer to him, letting him keep my hand. The other I placed on his leg. “It would be the biggest shame if this borrowed time was wasted,” I slowly slid my hand up his inner thigh as I made eye contact. I gave him my best sensual gaze and sultry voice. “Tell me, Simon, what would you do with me if you had me for an entire week?”

He gulped and I think he was sweating. Good, he always had the upper hand before. Speaking of, my hand was mid thigh at this point and I leaned in to whisper in his ear. “It’s ok, Simon. You can tell me the truth. Do you want me?” His whole body shuddered. I licked his ear lobe ever so softly, then quickly pulled away and laughed.

Simon gave out a long breath. His face was a deep red and I think I caught a glimpse of a tented lap. He took a big gulp of his coffee, “What time can you check in?”

I look at my phone. “I’d say by the time it takes us to get there.”

“Then I think we should get you over there pronto. We don’t want you to miss out on any of your vacation time, now do we?” Simon grinned ruefully.

Once back in the car, I slumped in the seat and feel like what I did wasn’t the best. It was a few minutes into the drive that I was able to speak.

“Hey Simon?”


“I…uh… I didn’t mean to upset you. I wanted to tease you a bit like we do, but I feel like I crossed a line and I’m sorry” I fidgeted with the hem of my dress.

“What? No, not at all!” He sounded genuine, but he was also focusing on getting us to the hotel so I couldn’t be for sure at the time.

The car pulled up to the hotel parking lot. I checked in with the concierge, located the hot tub and pool, and we made our way to my room with Simon carrying my luggage. I always book a King size bed, and it looked glorious next to the view of the city.

Simon whistled as he closed the door. “Ok, I can forgive you for refusing my hospitality. This is much nicer.”

I laughed and unpacked a few things. “I’m going to take a quick shower to get the travel off me.” Simon waved his hand in the air towards me while he looked through the local delivery menus.

The shower felt amazing. It was a nice break to chill out and re-calibrate my thoughts, especially from the little encounter at the cafe.

I got out of the shower, dried off and slipped into clean under things, but kept the summer dress. When I opened the door, the blackout curtains were drain, and a soft light came from the bed.

“Simon?” I called out. When I got closer to the bed, I realized the soft light were a couple thick, scented candles.

“Right here” He replied behind me, and for the first time he sounded his age with a low and rumbling voice. I jumped a little and felt a thrill go through me, unsure if it was fear or arousal.

Before I could turn around, he put a hand on my waist and the other on my shoulder. His lips were close to my ear, as I had done to him before. “Yes. The answer is, and always has been, yes.” He blew into my ear like he knew I hated and detached from me, laughing.

I turned around to look at him, er, his dark silhouette, and pushed on his chest lightly. “No fair! You scared me” Wow, that sounded lame coming out.

He stopped laughing. “No, completely fair. You got me in the cafe in front of people and I got you in the dark. Seems Even Steven to me.”

I huffed, embarrassed “Sneaking up on a girl from behind isn’t the same.”

Simon shrugged his shoulders “Yeah, you do have a point.” Suddenly, ataşehir escort he grabbed my waist and shoulder again and pressed me up against the wall near the bed, my breath catching. “How’s this, then?” His lips were a hair away from my nose, again in the shape of that grin.

My mind was rushing with a hundred different thoughts. Was he joking or serious? Would he pull away again? Was he wanting to fool around? His warm breath smelled nice from the coffee, so much so I forgot what I was thinking about and wanted to lick away any traces from his lips and teeth.

What was I thinking?? This was Simon! I can’t have this crush on him, not anymore. He was a friend, almost a brother. He’s never made any indication he was into me. This must be his way of getting revenge, of keeping the upper hand.

“I like when you’re facing me but still like you behind me” I tried to say it light but my voice was soft and shakey.


“Yeah?” I squeaked.

“Do you want to fuck me?” He asked.

“You need to first answer my question for real”

“But I already did” He seemed to purr in his low voice. Damn that voice! My panties were fresh a couple minutes ago. When did he get so smooth?

I shook my head a bit “Not good enough! There was too much time after it was asked. It doesn’t count” I tried to sound confident while I stalled for time.

“Ok then.” He kissed the tip of my nose, then made a bee line for my ear, nibbling ever so softly on my lobe. “I want you, Lynn. The thought of you turns me on and has for a very long time. I’ve watched you grow up and blossom into the gorgeous woman you are now. I. Want. You.” He growled the last few words. I could feel the ever growing wetness between my legs. “Now it’s your turn to answer.”

I wasted no time. “I want you, Simon! I’ve had a crush on you for so long, and I-” Before I could finish, his mouth was already on mine. His experience flowed from his lips to mine while I soaked it all up. These were his lips. Simon’s lips were on mine.

I wound my arms around his neck while he pulled me against his body. We would take quick breaths between passionate kisses. Our tongues met, intertwining with each other when they weren’t exploring the others’ mouth. His hands wove into my hair, taking the band out to let my hair free.

Simon broke away first. He followed the same bee line to my ear lobe, rolling it over his tongue and between his lips. My fingers found the base of his shirt and I slowly pulled it up. Once it was off and before he could resume, I pushed him back onto the bed. His eyes were wide with anticipation.

His belt was next to go, then the button on his pants undone and zipper pulled. His erection was begging to be free, however I denied him the next steps. I straddled over his hips, keeping myself ever so close to that large tent, I could feel the heat coming from it.

My hands ran up his torso to his chest, only to dig my nails into his skin and make thin, red trails scratched all the way to his belly. Simon gasped and twitched. I laughed at his reaction. I think it was ultimately my laugh that made his nipples hard.

“I can’t let these go to waste, now can I?” I kissed from his navel to his chest, nipping along the way. When I came to his chest, I gave him the same treatment he gave my ear lobes. Simon moaned with every flick of my tongue. He tried to put his hands on my shoulders, but I promptly took his wrists and held them down until I was satisfied with my work. Little dark hickies were starting to form.

Sensing when I was finished, Simon freed his hands and unhooked my bra. We took it off with my dress still intact, and my panties came off next. I was about to take the dress off completely, however he stilled my hands.

“I would like it on, kind of kinky” He explained. I shrugged in agreement.

Simon switch positions with me. I felt the age difference again when I was under him, and it excited me. Or maybe it was him pulling my dress down enough to free my breasts. I’ll just say it was both. I’m easily excited.

For a few moments he just looked at them. “Uhm… everything ok?” I asked, starting to feel self conscious.

“What?” He snapped out of his daze. “Oh, yeah. It’s just, I’ve fantasized about this before but never have I thought this would happen. That, and you have amazing breasts.” He reached out for them as if they were the holy grail.

His hands were warm. They groped and caressed, kneaded and grabbed. He would pinch my nipples and roll them roughly between his thumb and pointer. This was one of my weaknesses and I expressed as much. My hips and my back arched the harder and rougher he was with me. I started to whimper. My thoughts turned to mush as all I knew in those moments were the intense pleasure ümraniye escort welling in my breasts, and the deep aching building between my legs.

“Oh my, that really does feel good, doesn’t it?” With one last, long and hard pinch, he stopped. I was both disappointed and relieved, letting out a howl to express this.

Panting, I started to move but he pushed me back down to the bed. Without a word, Simon started to suck on my nipples. He would alternate between them, like they both needed the same amount of love and I was grateful for it. Whatever tit didn’t have a mouth on it was groped and squeezed, keeping it ready. It wasn’t very long until he graduated to biting. Oh those teeth. Those perfect teeth. I tried to put my hands on him but his free hand grabbed my wrists and held them above my head, out of the way.

I was reaching my limit. Being held down under him while he made my tits his playthings made me crave his cock. My hips rolled, my knees quivered, I whimpered and cried out.

“Please, Simon” I begged softly.

“Please what?” He bit down. I squealed.

“Please. I want you to fuck me. I can’t stand it anymore” I panted and tried to keep my thoughts in order. “I really need you inside me, now.”

Simon released me. His hands ran over the shape of my body from shoulders to thighs. He pulled his pants and underwear to his knees. I was finally able to see his erection, long enough to reach the end of me, and thick. My mouth watered when I saw how thick he was.

A look of doubt crossed his face momentarily. He shook it away and guided himself to my drenched opening, rubbing his tip up and down my folds coating himself in my fluids. I felt like he was overthinking his decision to change our status. I understood the thoughts he was having, however we were far too gone. To help him stop doubting, I leaned up and kissed him hard.

That did it.

His erection was hot as it was slowly pushed into me. I welcomed every inch of this burrowing serpent. Simon was about halfway inside me before I truly grasped how thick he was. I let out a gasp, then a sigh, and finally a groan. Forget the serpent, this was a leviathan. My nails dug into his arms, the pressure welling.

“Holy fuck” Simon shuddered as his tip hit my end.

“Yes, please” I responded as he was pulling out. There was some relief that came from his absence, but it made me crave him more.

I didn’t have to wait long for him to come back. Simon bucked his hips back and forth, testing out our rhythm, then started with a modest pace. I sighed and panted out my pleasure. Since he was busy, I started to play with my breasts. This got his attention and he rather enjoyed watching the show I was putting on for him.

Once he was pleased with his basic “Ins and Outs”, Simon hooked an arm under my back to grab a shoulder while the other held on to my hip. I could feel his weight on me and my mind raced with what he would do to me.

With a very sudden intensity, Simon began to thrust himself hard and fast into me. He held me in place and used my chest to keep himself steady. I cried out and wrapped my arms around his back, holding him to me.

I could feel every bit of his cock, and the pressure turn to painful ecstasy. I loved that sensation above all else. The harder he pumped, the wetter I got, the more I moaned and cried and whimpered. After some time, all I could do was gasp in air and breathe out the occasional long moan.

Simon quickly pulled out. “I want you from behind” He panted. I obeyed.

I turned around, pressed my chest to the bed, stuck my ass in the air and braced myself against the headboard. My dress was pushed down to my waste and I felt Simon’s hands take strong hold of my hips seconds before he slammed into me. The ecstasy of pain was multiplied in this position and I let myself go as Simon plowed relentlessly. He was rutting like a dog in heat. I couldn’t tell which was louder, our moans or the sounds of our thighs smacking against each other, amplified by the juices flowing from me. My inner thighs glistened with my fluids.

Wanting to really push him over, I lowered my ass down to make the yoga child’s pose. He followed suit, and enveloped me with his body. Simon grabbed my breasts from under me while he made quick thrusts.

I could feel his hot breath on my neck get more and more ragged. This new position was doing it for the both of us, as my time was soon and his twitching was frequent. With my years of kegel exercises to my advantage, I tightened over him.

We cried out as we climaxed together, and I swear my eyes rolled back. He pumped each load into me with vigor. After a full minute of release, Simon pulled himself out. I turned over and he collapsed on me.

It was some time before we slowed our panting. I glanced at the table side radio clock and realized we had only been intimate for about half an hour.

Simon noticed where I was looking. “It seems like we have quite the night ahead of us.” He reached over me to turn the clock around and grabbed my breast.

“Yeah, I might have to reschedule a few things.”

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