Summer Sublet Roommate

"Hello? Is anyone here?" I called out, hoping John was there. Getting a summer sublet from my professor's younger brother while I worked my summer job in his city wasn't just convenient. I'd seen John's picture while having sex with "Professor Matt" after office hours. Matt was okay, a serviceable lay and discreet about it since the wife he was cheating on was the daughter of the Chairman of the Board of Trustees. This wealthy and powerful father in law had the same name as the school's founder, except for the fancy Roman numeral after it. And Matt was giving me an "A" along with strong recommendations to business connections he'd made through his father in law. So yes, it was worthwhile to fuck my marketing professor on the way to my MBA. 


But John was the real prize, or so I hoped. In his photo he was HOT!

"I'm in here," John yelled back. I could hear his footsteps coming down the hallway. I looked over and smiled as he walked into the room. Oh yeah, Matt got the brains, but John, now he got the looks. 

"Hey John, I'm Dolly, your brother told me to pass along a "hey bro!" Anyway, I appreciate the cheap rent so close to the "L" and in such a great building. 


For those to whom the "L" reference meant nothing, I was working in Chicago. "Really, thanks again." Then I looked him up and down, about my age, cute butt, muscular, surfer boy hair with dark undertones...Matt had said to me, "John could use the sublet money, and if you like me you'll love him. All my girlfriends always had crushes on him. Hell, my wife even teases me about him being hot.


Like I wanted to talk about Professor Matt's spoiled rich bitch wife when he and I hooked up, you know? Guys, take a lesson; we'll listen if you really need someone to listen, but if your wife frustrates you, would you have a better time with us if you treat our time as a vacation and give us a chance to suck your cock.  Perhaps the wife conversation might be "Wow, Dolly, that felt amazing, my wife never does that for me...."  Though of course I'll talk about anything you truly want to talk about.  But getting back to my sublet with my professor's hot brother....

"Well, big bro Matt told me about you, working that money management firm this part of the summer, just six weeks, and he mentioned you were cool, and mature, and that I could use the money.  He seems to have forgotten to tell me how good looking you are.  So, welcome to Chicago, Dolly."  A lady always enjoys hearing that she is good looking.  "Beautiful" is better, as is "sexy" or "hot".  You're taking chances with "MILF" or "fuckable" unless you know her pretty well and were certain to get laid anyway.  John played it safe.  I owed him a compliment in return.


"Well, thank you kind sir.  Yeah, tell me about Matt leaving details out. . .I assume you're a brainiac like he is, but he never mentioned how "hot" you are.  So my apologies to whatever supermodel you must be dating for imposing on your space this summer." The words just flowed, ad-libbing.  Heck, I might even have been hoping there was a supermodel in the mix.  See if I might make the summer a Two-fer One special and sleep with both of them.


John laughed, and his eyes were taking an inventory, stopping at my boobs.  "Sorry to disappoint, no supermodels around here unless you're one when you're not in MBA school.  In fact, no girlfriend at the present time.  I'm a lawyer, just getting my practice established, and you're standing in my 'virtual office'.  The walls are pretty good so I'll take the business calls into my bedroom if you're home and not disturb you.  Let me show you you're bedroom.  We're pretty lucky, we've got a lake view if you twist your head a bit."


 He helped me with a duffel bag I'd strained my shoulder lugging, and I towed the wheeled case.  Loved the way this man's eyes were checking me out.  Since I'd seen a photo, I dressed to flirt a bit.  I was wearing, white short shorts, a pink spaghetti-strap shirt that really showed my boobs and with spaghetti straps, that meant no bra.  I know, right?  My long blonde hair was pulled back in a pony-tail. As usual, my skin was well tanned, and my long legs as always were nicely toned, my tummy flat and tight and showing a bit when I reached up to upper shelves or otherwise stretched.  My breasts were on high alert and my nipples were perky from the air conditioning. Since my shirt was cut so it showed quite a bit of cleavage, I guess it wasn't fair and he was caught staring. I noticed his jaw hanging open and laughed.

"Surprise!" I said. "I guess you weren't expecting someone like me, were you?"

"Honestly, no I wasn't! I pictured an accounting or actuary nerd with thick glasses who avoided fun or laying out in the sun like it was the plague!" I stood up and walked around the couch to hug him.


"Always nice to exceed a man's expectations." We laughed.


"So just let's get this out of the way.  I assume you're sleeping with my brother."


Okay, hadn't thought that was going to part of the greeting and moving in process.  "Matt's married, John, hello?"  I tried to deflect.  John wasn't being deflected.


"Not happily, he isn't.  Its cool, Dolly, I won't bug you about it.  But if you are, then he totally scored way above his pay grade with you, and you know something, you look familiar.  Oh my God, were you a centerfold or something like that before you went to B-school?"


Which got another smile and laugh from me.  "Um, no, never posed nude."  In a magazine, anyway, I thought to myself.  Let's hope he doesn't somehow find his way to Dolly's World, my website, where you're reading this blog entry.


"Okay, no centerfolds out there to be found," he continued, "but you're still way hot and look familiar."  His eyes had changed their parking place from my tits to my face.  "Great smile, by the way." 


John was free and easy with compliments, a fit man of about six feet in height and maybe one eighty of lean looking fitness.  Dark, short hair, mildly tanned, clean shaven, brown eyes, and great looking legs and arms popping out from his khaki shorts and Chicago Cubs polo shirt.  "So where do I know you from?"


"I used to play tennis professionally.  Never won a slam, no slam finals, in fact, but was top ten ranked for a while before moving on once it became clear to me I'd done all I could.  No regrets.  So you either saw one of my matches or maybe some of the sports fashion modeling that made some popular magazines or a couple other photo spreads.


"Or maybe it was the 50 hottest women athletes at a web page." He was nodding.  Yeah, they'd ended up with the barely legal lace thong and bra shots I did on a lark for a certain sports weekly with a bikini issue that didn't make the magazine but did make their web site.


"From the look on your face, John, you're a subscriber to that sports mag and as a subscriber have been to the outtakes page at the web site."  Big smile in response from him.


"That's who you are!  You were wearing blue with white trim, bent at the waist but the wind messed up your hair I guess, and you were laughing.  Clear nail polish, toenails were a matching blue.  I remember thinking you looked like a sexy Colts fan in those colors."  Sheesh, he'd memorized every pixel.


I shook his hand, hugged him, kissed his cheek.  "If I get the job offer at the end of six weeks, maybe I can recreate that pose for you, hot shot."


He had a chubby in his pants.


It was now just a question of when, not if.


I got settled in, called my office where I would start two days later and was told the first day would be introductions, administrative, sign an I-9 form for employment background eligibility, and confirm I had all my needed documentation.   I unpacked, and plopped down, rather spent, in the living room.  By this time I realized I'd skipped lunch while unpacking, and I also noticed that John had been right about the loft apartment I was sharing.  Fantastic restoration of former industrial space, exposed brick, high ceilings, ductwork, but none of the glare that comes with industrial light fixtures.  Decorated well enough to make it homey feeling, yet sparse enough to confirm that John needed a woman in his life to add some finishing touches.  I was toying with the word "touches" in my mind, considering how I'd like to touch John, when he startled me out of my solitary day dream.


"Chateauneuf duPape? Big bro said you like reds."  John extended a healthy sized glass, plain but sturdy stemware, and he held his own glass, too, the bottle having been set down while I was fantasizing about whether to rub one out that night or skip the cat & mouse and simply seduce him the first night.  Clos Des Papes.  Wasn't familiar with the label, but a sip or two let me know that this young lawyer had decent taste.  "Excellent" I told him, and he sat down next to me, with some space in between.

 "So you're not only a financial whiz but also a professional athlete and some kind of fitness model?  I mean, damn girl, look at you. You've been working out. You're hard as rock!"


Maybe John wasn't too fond of cat & mouse either?


"May I?" He asked, his hand half-way reaching for my arm. 


"Why not, please, but be gentle, I'm new here." I replied.  We smirked and his touch was tentative, reverent.  I've been touched like that on Dolly dates, when my dates are Fan Boys, into hard bodies.  I'm not some kind of body builder or physique or figure competitor, but I work hard to stay fit, even now that I don't play on the circuit any longer, and love being appreciated.  He ran his hands over my arms, shoulders, trapezius, then skipped past my boobs (though he looked up and made eye contact with me as his fingers passed by) then down to my stomach and then thighs and calves.  He looked back up at me from my body, a sense of kid on Christmas morning on his face.  Then he looked embarrassed.  "You're seriously hot, but oh, jeez, sorry to be mauling you when you've just gotten here, please don't call the police or move out."  He pulled his hands back.  Love when they're under a spell, like John has been there for a few moments.


"So mauling me next week, that would have been something I would need to tolerate, but since I just got here you apologized?  I missed that in the sublease.  I forget, was I supposed to give you head in advance, like a deposit, or do I get to wait until next week for that, too?"  I was pretending to be pissed and insulted.


"No, Dolly, I didn't mean, um, shit, really, it's just that you, oh, fuckit, and I'll never hear the end of this from big bro Matt, either now."


Big Dolly smile.  "John, I'm just messing with you.  Thank you for the compliments, you didn't maul me, and you didn't touch any of my naughty bits.  And may I say," I continued as I touched his abs through his shirt, "You are in great shape yourself--hey! You have a six pack!, I love six packs! Let me see!" I started pulling his shirt up so I could objectify this fine specimen of young adult male meat puppet, but he quickly stopped me.

"I don't think so," he said, in a playful voice, and I laughed as he pulled away.

"Awwww... You're no fun! Anyway, I'm sure I'll see your abs eventually! You can't go into the pool I've heard about up on the roof with a shirt on. Or is wearing a shirt in the pool something you usually do?" I teased.

 Now we were having fun.  He was laughing, and didn't even answer.  So I continued,  "Whatever loser! Muscles aren't the only thing women go for nowadays. But I guess you have to compensate for something by building all those muscles.  Wonder what little thing you're compensating for?"


He stood straight up.  "Never had any complaints.  About these small ears, I mean."


Were they were a tad small? I looked.  Hadn't noticed, and now that he said something, I wasn't even sure that they were small.


"Well, we've got to get along for six weeks. Can I make you dinner?" he asked.

"That depends. Are you a good cook?" I teased. "I don't want to end up with food poisoning!"

 "I'm a great cook! In fact, I used to cook for my friends at law school once a week. If I was bad, I don't think they would let me!"

 "I'm going to take a shower, then."  And I stood and left.


And that fucker!  He didn't follow me in, and went ahead and prepared a chicken Florentine with a very light sauce, not heavy with unnecessary calories, and sautéed summer vegetables that he later told me were from an organic grocery and the herbs were freshly grown as well.  We finished the bottle of wine.


We stood side by side, loading the dishwasher, and he hadn't said a word about the fact that I had emerged from the shower with my hair down, barefoot, wearing a man's white oxford shirt, buttoned enough to hide my panties at the bottom (the shirt went to mid-thigh on me) and unbuttoned enough to show ample cleavage.  A sturdy enough cloth that my nipples could not been seen visually, though they were poking the fabric.  So as not to be a total slut I did wear a pair of panties, white lace.


He threw on some jazz.  No idea who the artist was, but I liked it.  I stood at the full length window, looking crooked to the side so I could see the lake. I saw his reflection approach from behind.


"That's my brother's shirt, right?"


"A lady never tells."


"The joke some girls told in law school was that sometimes they just slept with guys for the t-shirt they'd get to sleep in after sex and then get to wear home and never return."


"Lose many shirts that way, Johnny boy?"  Must have been the wine.  The food.  His body. His hands on my hips as we spoke while looking at each other solely in the reflection in the window.  Then he leaned forward, and I felt the poke.  THAT poke.  The "he's got a woody" poke.


"Not that I lost count or anything, but I graduated with less clothing than I started with, so yes, some of my shirt left with women I'd slept with.  So, are you a Michigan football fan?"


What?  He wanted to talk about college football?  "Um, no, I'm from the South, I'm all about football but not the kind they play in Michigan.  Why do you ask?"  At which point I criss-crossed my arms across my waist, grabbed his wrists and pulled his arms around me, forcing him closer and his poke to become more pronounced.


"Was just wondering if you might want to sleep in my Michigan football t-shirt.  It's vintage, so it’s been washed a lot and really soft.  100% cotton."


"And what might a lady have to do to earn the right to sleep in such an esteemed t-shirt, Johnny Boy?"  There it was again, that nickname I'd spontaneously come up with for him.  He didn't flinch when I said it, though.  I was buzzed enough to be relaxed and horny and lovey dovey, not so drunk as to wreck a night.  I love that level of buzz on the occasions when I do enjoy a bit of wine. Mmmm, about that point was thinking more about making love than fucking.  I love both of those forms of pleasure, and appreciate the distinction between them.


"Well a lady would allow a gentleman his proper due as the land lord."  Okay, English nobility fucking the farmer's daughters, Medieval times, I could play along.  And then he changed directions.


"But if she wasn't such a lady, but instead a smoking hot hard bodied sexy tennis fitness model chick, maybe she might have her run of the closet to sort through the available shirts to be claimed and finally get her hands on my abs and my hands on hers and what happens in John's loft stays in John's loft."


I spun.  We were now facing each other.  God he had deep eyes, the kind that draw you in. Our arms hadn’t moved, so now instead of arms across my tummy, his arms were on my butt and I moved mine forward to his tush.  His buns felt great in my hands now that his "poker" stick was pushing into my waist, his hard abs now so inviting, I was salivating at the thought of kissing and licking down his body to those abs.  And then beyond, to "Poker-ville", the land of what was poking me. 


And now, kissing.  He was softer and more romantic styled in his kissing than I'd anticipated.  Which, for those taking notes at home, is always a very welcome style. His hands explored, me, and I pulled his shirt off and he reached up under my men's' shirt tails and slid my bikini panties down, his fingers making a very quick pass along my smooth, bare pubic region to note the absence of any hair below my eye lashes. Another kiss, still soft, but deeper, more confident and knowing. My extremely wet, excited pussy must have communicated to him that this was not just some tease. 


I undid his belt and lowered his fly, and as I reached into his boxers he began unbuttoning the shirt I was wearing.  His brother's shirt.  The one I'd kept after an office fuck with Professor Matt, forcing Matt to wear a tweed jacket with only a t-shirt underneath to the campus store where he bought another oxford shirt before going home.  And then my mind returned to John, my land lord and any second now my lover, as his warm hands cupped my breasts after the final button was undone on the shirt.  He nuzzled my neck. I closed my eyes and floated in the sensations, my hand softly stroking his erect cock, which felt nicely sized, maybe six, maybe more, certainly plenty for amazing sex and then some, "Mmmm, yessss, my land lord, you make stake your claim to me this evening," I whispered. I felt his cock twitch in my hand when I said that. I next felt a smear of pre-cum over the nice-feeling head, and I managed to slide his boxers down to the floor.  "I've got protection in my backpack," I whispered and John replied, "and I've got some in my nightstand, but first I need to kiss the rest of you, so that protection can wait."  And he led me back to the sofa and laid me down, then knelt and kissed my mouth gently, and his finger tips and lips, even the tip of his nose, made a steady but sensuous trip down through the valley between my breasts, with stops at each nipple, then a quick tour of my abs, my hands clasping his strong arms as I swung my legs apart, up, wide, and then one ankle up over his shoulder to open myself and present my body for his administration of oral pleasure to me.


I'd been at his apartment for about six hours at that point.


John was delicate when tongue met pussy.  Dabbing at my fluids, not quite touching my pleasure nub, yet not quite avoiding it, either. His fingers holding me, molding me, positioning me.


To this day he swears he never heard me scream, "oh dear God just fuck me already!"  But I'm pretty sure I did after he'd shown a lot more restraint about tasting me than his big bro had ever shown.  Matt wasn't a terribly skilled pussy eater, but he loved it and practically dove in. 


We were at his place, and John knew where his own condoms were.  He never asked about them, and I assumed that was because he'd figured out I was fucking his brother.  Or he was just responsible.  A few weeks later during pillow talk he told me that as a lawyer he'd represented a client with a love child born from hook up sex and that he didn't want to create any such situations.  Responsible.  By the time he told me that we'd been through MANY box loads of condoms.  But back to that first time...


I rolled him onto his back and snuck on top, straddling him and took the condom out of his hand and held it while I introduced his man tool to my CIM-worthy mouth.  He was very sensitive I could tell right away from how he twitched and flinched when my lips teased the underside of his shaft and my fingers cradled his balls. I'd have loved to go to completion on him, taste a load of his young potent seed right then and there, but my pussy felt way too empty. I wrapped my present and then raised myself up, placing the pulsing head at my entrance.


John reached up, and held me at my chest.  Mid rib-cage actually, his thumbs on my tits, but his strong hands bearing my weight.  "Stay with me tonight" he said.


He wanted to negotiate and get clingy now, BEFORE?


"I am staying here, John, I'm living here for the summer."


'No.  Here.  My bed. With me.  All night."


Like I was going to argue with him?  I felt it touching my inner lips, and I wanted him deep in me, "Yes," I told him.  Then I grabbed his hands in mine, held his hands away from me and my legs controlled my slow absorption of John's cock into my body.


No, it didn't last terribly long.  It was divine, and I loved the look on his face.  Excitement.  Not lust, but excitement.  Like he'd gotten on a coaster at Cedar Point at Lake Sandusky in Ohio (look it up if you aren't familiar with that roller coaster park.  I road coaster but no cock on one interesting date with high ranking state official in Cleveland once.  Roller coasters and then a private plane to Columbus for a Buckeyes home game.  Such excitement even though it was northern football that can't compare to how we play college football in the South.  I asked who I would have to fuck to get to dot the "I" in Ohio.  Still trying to find out.  If you know, call me.).   His face when he'd filled his condom was bliss, and he embraced me, like a lover. Yes, he dozed off while we snuggled, and I listened to him snore a bit before I nudged him.  Wanted to dispose of his condom and maybe clean up a bit.


We fucked doggie style the next morning as the sun rose over the lake, then took a run not long after along the lake shore.


I tried to hide his brother's text messages to me.  Claimed to be going to Florida to visit family the weekend that I went and shacked up with Matt back at my MBA university while Matt's wife (John's sister in law) was in Europe with her family.  Apparently that was her tradition, even as a full grown adult, going to Europe with her family.  Quaint.  Gave me a chance to enjoy her lusty husband banging me.  So different, sex with Matt compared to my nights (and mornings) with John.  Yes, and some afternoons, too. Or that dare that I accepted and got to add a stall at the Chicago Theater to my list of locations!


I still hadn't slept in what was supposed to have been my own room at John's condo as my sublet was winding down. I'd been less committed than expected regarding my internship, since I had found a relationship I hadn't expected when I came to Chicago.  I could tell I wouldn't get a job offer.  I was not thinking about job offers, though, as John entered me missionary style, a very passionate embrace and deep kiss linking our bodies all sorts of ways, and me pulling his ass into me, wanting to feel as much of him hard against my body as I could.  Talking and figuring out what would happen next would take place later. I sucked him off already, then showed him his bounty, then swallowed, so he was lasting and I was enjoying and cumming, more than once. Familiarity breeds orgasms.

Would I be thinking about what to do about my fuck-buddy relationship with John's brother, my professor Matt, when I left Chicago the next day?  And how I could balance fucking both brothers? Matt didn't know that I was having marvelous sex with his brother. John had simply assumed, correctly, that Matt and I were intimate, even though I had never told him.  John was so cool about it!  These brothers were great cocksmen and super-cool, I joked to myself once that I wished their mom had birthed more sons...

And as John kept thrusting into me, grunting,  panting, and not saying much other than, 'Oh God, mmmm, yes, Oh God...." I was thinking that yes, I really did hope to keep them both as lovers.  But no, I didn't' spend the next day wondering about that.  Because while I was arching my back, feeling a third "pop' approaching from John having introduced his fingers to the stimulation of my clit, I heard his buzzer, indicating someone at the security door. 

"Hey little Bro! Surprise!  Buzz me in, John, is Dolly there?  I guess I've got a surprise for you John, to tell you the rest of the story about Dolly and me...."

John smiled.  Then closed his eyes and stiffened, his entire body tense and I felt him throbbing and I clenched down on him inside my sex. He kissed my neck, in the only bed I'd used in his apartment all summer. "I've got a surprise for him, too."



Purely Fictional Fantasy For Your Reading Pleasure! Enjoy!

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