The Situationship Pt. 01

It had been 9 months since my divorce and I finally felt ready to date again. Truth be told, I had been on several dates in those first few months, but every time I started to feel like I could be close with someone, I couldn't shake my feelings for Jessica. Everything reminded me of her and the life I had. Worse yet, any sort of rejection would send me spiraling into depression and despair. The final straw was what should have been my dream date.

We met at a 'Friendsgiving' that I was invited to last minute. I hadn't spoken to Roger in months. I think the fact that Emily was so close to my ex caused them to become weird with me. I get it, and unfortunately, I got used to it. I happened to cross paths with him coming out of Ace Hardware and we spoke briefly about catching up. Three days later he texted to invite me to their annual Friendsgiving that Sunday before the holiday. He ensured me that it was mostly their friends from outside my old circle and specifically, "Jessica will not be there."

I arrived with a couple of bottles of wine and as he promised, there were few familiar faces. We had some drinks, shared some laughs, and enjoyed a great potluck dinner. After dinner the guys all sat outside smoking cigars, nursing our engorged tummies. I started feeling tired as we wrapped up the cigars and just as I stood up to excuse myself, the sliding glass door slid open and she walked out.

Every bit of 6ft tall, curves for days, long red hair, and a smile that could destroy the world. Her green sweater and jeans might as well have been painted on her body and she flaunted it all in a pair of heels that had her towering over all of us. We caught eyes immediately and never broke that connection as she walked around to hug everyone and apologize to Roger for being so late.

"Hi, you must be Jack. I'm Jessie."

Of course, another Jessica. Probably should have run for the hills right then.

The flirting was immediate. She was so bubbly and endearing, everything flowed naturally. We stood and chatted for almost 15 minutes without even realizing everyone had gone inside. I might still be standing there staring in to her ice blue eyes today if Emily hadn't interrupted.

"Guys, we're doing shots! Get in here."

Jessie sauntered through the door and Emily mouthed 'wait' as I began to follow, stopping me outside and sliding the door shut behind Jessie.

"She's hot, right?"

"Unbelievable."

"Look, I know I've always been close to Jessica, but I found out what she did and I'm not sure I want someone like that in my life. I know it's been weird with us because of it, but when Roger told me he ran in to you the other day, I really wanted us all to reconnect. I immediately went into matchmaker mode and thought about Jessie. I hope you don't mind, but I think she's fucking PERFECT for you."

"I'm glad Roger reached out. This has been fun and she's absolutely gorgeous, but if I'm honest, this feels kind of weird you setting me up."

"I know. And I'm sorry we haven't reached out sooner. It's been awkward for us, not that that's your problem. Jessica never told us not to talk to you, but she did kinda make us feel like we had to take sides. Since I've literally known her since 7^th grade, I made the stupid decision to listen to her. I'm really, really sorry. It's all my fault and now that I know the truth... well... fuck that bitch."

Emily's laugh brought a little smile to my face and she pulled me through the door to meet everyone in the kitchen. The party died down pretty quick after the shots and people started trickling out until I found myself alone on the couch with Jessie. We talked and laughed without a care in the world. It was just so damn easy.

"Ok, you two need to make out and exchange numbers cause Emily's been in bed for an hour and I got to work in the morning. I mean, you don't have to go home, but you sure have to get the fuck out of here!"

Roger always had a way with words.

"Holy shit! It's fucking midnight! I have deposition early in the morning and I'm all drunk. Jack, you're a terrible influence!"

She smiled so wide I practically fell into her mouth. We shared a nice little kiss while Roger whistled and ribbed us. I walked her to her car in the street and we kissed again before she took my number and pulled away.

Driving home I was on cloud nine. She was just... wow. My phone buzzed just as I pulled in to my neighborhood, 'Nice to meet you tonight, Jack. I'd like to see you again. Goodnight!'

'We'll definitely be seeing each other again soon. Goodnight!'

Over the next week we texted constantly. Memes and gifs, 'how is your day,' and a great combination of silly and deep. She continued to be absolutely perfect in her humor, charm, and depth. She was that goddess level balance of beauty and substance. Needless to say, I was smitten.

We made plans to go out on Saturday. I planned for dinner at a great little Italian restaurant on a lake, a nice stroll around the park after dinner, and then drinks and maybe a game of pool at a fun little dive bar. A great blend of classy and casual with plenty of opportunity to continue our effortless conversation.

I picked her up from her condo at 6pm on the dot and she, of course, was perfect. A fuzzy red sweater that accentuated her narrow waist and cantaloupe-sized tits. Another pair of painted on jeans and heels, though this time more modest. She had her hair up, a little more makeup, and smelled like a dream. It was all smiles and a big hug the second I saw her.

You may notice a trend here, but the actual date was, for lack of a better term, perfect. We shared a bottle of wine, flirted like high school kids, held hands as we walked around the lake. We made out after gazing at the moons reflection on the water and talked about dream homes and retirement goals. When we got back in to my car, I offered the dive bar as an option and she threw me for a loop when she said she'd rather go home. I thought maybe something had put her off, though I didn't have any indication. She was quiet on the way back to her apartment and I felt awkward as I walked her to her door.

I wasn't sure if I should even kiss her as she slid the key in to the lock and turned to face me.

"I had a great time, Jessie."

All of a sudden, she became a bit bashful and seemed to struggle with eye contact. She looked nervous.

"I don't want you to get the wrong idea, Jack... I'm hoping this isn't the end of night for us."

"Are you inviting me in?"

"I am. Is that ok?"

"I'd love to, Jessie."

"I'm sorry, I know you were thinking everything went south somewhere along the way, but when I decided I wanted to bring you home and then I got in my head and clammed up."

"It's fine, we obviously have some chemistry and I don't suspect this to be the last time we see each other regardless."

She smiled as she pushed the door open and grabbed me by the hand, leading me in to the kitchen. She handed me a bottle of wine and grabbed a corkscrew as I teased, "ugh, more wine, I'd rather be drinking beers and shooting pool at that bar."

My little joke seemed to put her at ease. I poured two glasses, we toasted to a good date, and each maybe took two sips before we began kissing under the harsh fluorescent lights in her kitchen. Her plump lips and probing tongue were much more aggressive as my roaming hands squeezed and pulled at every inch of her luscious body that I could reach. Within seconds we started spinning around out of the kitchen, kicking shoes, tearing off shirts, and fiddling for entirely too long with my belt. It was a whirlwind of passion as we bounced down the hallway to her bedroom, leaving a trail of clothing and pheromones along the way.

My cock was rock hard and poking out of my boxers as we hit the bed. We scrambled to remove the last few bits of clothing as we fought to keep our lips connected. Boxers and socks off, her bra tossed to the side, I pushed her back to the bed, bit hard on her lip, and slid down, tearing her lacy red thong off her pasty, curvaceous body. She ran her fingers through my hair as I dove in to her neatly trimmed, bright orange mound. She dripped as my tongue drew circles around her perfect little opening and tiny, rock-hard clit. My hands roamed up her angelic body, pinching her tiny pink nipples and squeezing her thick, meaty thighs that had me in a headlock.

"Oh my god, FUCK ME!"

She pulled hard on my ears and her juices poured from my chin as I climbed on top of her. She licked my lips and kissed me so hard our teeth gnashed together. She clawed hard on my back as my eager member met with her gushing slit. She bit hard on my lip as my cock pressed in to her tightness. She wrapped her legs around me as I thrust in to her, raising myself up and watching her perfect tits swing in circles while she threw her head back and bit her bottom lip, digging her nails deep into the pillow behind her head and the comforter beside her.

"FUCK ME WITH THAT BIG DICK AND MAKE ME CUM!"

Boom.

Those were Jessica's words. I mean, she certainly doesn't have them trademarked or anything, but in the 14 years we were together, she always said the same exact thing when she was ready to cum. Verbatim. It ripped through me like a thousand daggers. I kept pounding away, but the bell could not be unrung. My mind was spinning with thoughts of me catching her with that fucking kid. The fucking neighbor kid for fuck's sake. Barely 18 years old, jack hammering away at my wife in my fucking bed ten minutes after I left to go fix HER MOM'S washing machine. Forgetting my sockets had never been so painful.

My cock was soft within seconds and my brain totally scrambled. I stood up off the bed, trembling as I raced around the bedroom and into the hallway, picking up my clothes, as I struggled to see through the tears streaming down my face. Poor Jessie was without words, trying to say something, anything, to understand what in the hell was going on. I heard her crying as I threw on my clothes in the foyer and darted out the door, my own sobs echoing through my head.

I raced home, screaming sweet "FUCK YOU"s at the top of my lungs into the night. I was so out of sorts that I actually considered eating a bullet, something I hadn't really thought about since the later stages of our abysmal marriage counselling. Thankfully, I just cried myself to sleep, heartbroken and utterly embarrassed.

'Did I do something wrong?'

Jessie's text came through as I sat down at my desk, almost two weeks after that night. My heart sank.

'I'm so sorry. You were perfect. You are perfect. I haven't been with a woman other than my wife in a long, long time. It triggered something in me and I completely broke down. I'm really embarrassed. I should have told you immediately instead of running away. I really don't want you to think it was you.'

No response.

That was the last I heard from Jessie. Didn't hear anything from Roger or Emily either. I'm guessing everyone was just embarrassed for me, or upset that I hurt Jessie. Who knows what they know... there's nothing I can do about it now.

6 months later I'm fiddling around on dating sites. I was thinking that I'm ready, my therapist thought I was ready, and in the least I figured the online thing is safer for me. If I got in to another bad situation with a date, at least I won't have to suffer the embarrassment of it filtering back to everyone I know. Two weeks in and I had some matches and a few conversations going. It all felt pretty good at that point and one of my matches was particularly interesting.

Monica's cute, she's fun, and she was in almost exactly the same boat I am. She'd been divorced for 6 months from her cheating husband. Mine was the neighbor kid, hers was some floozy waitress from a bar. She's so open and honest, we vibed almost instantly. We both agreed that we weren't ready for something serious and reveled in the fact that we've both gone through so much.

When we first met for dinner at a great Mexican place, I was pretty excited. No pressure, no big expectations, the worst-case scenario I'd end up with a friend and someone I could bounce my feelings off of without judgement. And, it would honestly feel good to be needed by someone in that same way.

In the parking lot, I was totally at ease. I scrolled through our conversation as I waited for her to text me upon her arrival, noting how deep we had gone. I still can't believe how open we've been.

'I'm here.'

Walking through the lot I really liked what I saw as she approaches. Petite and cute, straight shoulder length brown hair with blond highlights. She wore tight little white shorts that showed off her little curves and tanned bronze, slimthick thighs. I'm not mad at that tight baby blue t-shirt either. Nice little B's. She's pretty hot.

With a hug out of the way and some slightly awkward eyes, we're seated in a corner booth per my request. Some small talk and the flood gates were open. All the horrid details we only briefly touched upon were brought out in the open and midway through the story of Jessie I didn't have a care in the world. She's hot, but she's going to just be a friend. We both felt it.

"Wow, that had to suck. I had a similar experience. I just laid next to him and sobbed all night. I felt like I cheated or something. So much guilt, I really wasn't ready."

"I'm still not sure I'm ready now, honestly. I like to think I am, but I'm not sure right now."

"Yeah, me too. How about this? I won't talk about your big dick if you don't call me 'baby.' Maybe then we won't both end up a blubbering mess."

Too funny and very true. She's a really cool chick. There's definitely something between us despite the friendship vibe and I can't quite place it.

"So, my roommate told me I need to fuck you tonight."

"Excuse me?" I laugh, choking on my Modelo.

"Ok, confession time. We read your texts together sometimes. She's in a similar position and I'm trying to help her through it. Her husband left her a few months ago - just disappeared. Turns out he cleaned out the accounts, cancelled their lease renewal out from under her, and is off who knows where doing who knows what, never telling her a damn thing. Gone. Sorry, don't hate me for sharing you with her. I haven't shown her anything juicy, just trying to show her that there are other people out there going through the same sort of thing."

"And she wants you to fuck me?"

"Ha! Yeah, I think she's trying to live vicariously through me at this point since I'm so far ahead of her in this process."

Her big brown eyes were intoxicating as the sun glinted off her smooth, tan skin.

"So, I see you have plans then." A big smile shot across my face.

"Well, I totally didn't, but... maybe." Her cute, sheepish smile invited me right in.

Check please!

I was nervous and totally excited as we pulled into my driveway. My big empty house hadn't had another woman in it for over a year and my instinct to change my sheets that morning was an excellent choice. I could tell she was a little nervous as we entered the kitchen through the garage. Nothing a bottle of wine wouldn't fix.

Handing her the glass as she sat on the couch, neither one of us knew exactly how to act.

"Is this weird?"

"Well Monica, it's definitely different. I've never quite gone into something like this... it always has just happened along the way, ya know?"

"Glad it's not just me."

"Oh, for sure. Maybe we just relax, take the pressure off, and start with a kiss?"

"I may or may not have been thinking about kissing you, Jack."

Smiling and dropping her glass on the end table, she turns back to me and leans in close. I stretched my arm past her, hovering close to her face and placing my glass next to hers, our eyes locked in anticipation. Her face darted forward and her soft lips pressed against mine. Immediate animal lust took over as our kissing was perfectly in sync. The perfect balance of lips, nibbles, sucks, and deep twirling tongues. My cock drooled as it swelled in my shorts. Her fingers ran up and down my back pulling me on top of her as she laid back on the couch. My hands feverously pawed up and down her perfect little body. Her soft thighs were silky smooth and her ass demanded to be squeezed. Pants and moans and...

"Hold on. Stop."

"I'm sorry. Are you not comfortable? Is this going to fast?"

Laughing as she reached behind her back, "no, this." She pulled the remote from behind her and we giggled at the only thing making her uncomfortable in that moment was an errantly placed tv controller.

"Let's go to your room."

Wrapping my arms around her, I hoisted her up to my chest, carrying her through the house into my bedroom. Our mouths continued to work in unison as her tight body clung to me and we fell onto the bed. She pulled my shirt up my back and I ripped it off, tossing it across the room. She reached down and felt my hard cock, immediately unbuttoning my shorts and dropping the zipper. Her legs sprung up around me and with her toes, she pushed my shorts and boxers down effortlessly.

"Oh, you are... uh... I don't want to say it." She laughs.

"It's ok, you can say it."

"You do have a big dick."

We laughed as she lightly stroked me between her splayed legs, our eyes locked together. She shoved me back, "Lay down!"

Pulling the scrunchy from her wrist, she wrapped up her hair into a ponytail and deftly bobbed my throbbing cock. She slurped and twisted with her hands in opposite directions, making me writhe in pleasure as I stretched to reach down her shirt. Holy shit, this girl is fucking amazing!

"Oh my god, slow down you're going to make me cum!"

Her efforts intensified as she moaned, "MMMMHMMM!"

I exploded down her throat, feeling an intense pressure as she swallowed every last drop. She was unrelenting, vacuuming every ounce of fluid from my quivering body. I trembled as I softened in her mouth and she wiped the spit from her chin.

"Jesus Christ." I pant.

"Yeah, I'm ok at that."

"I'd say so..."

"Uh, oops, I think I gave you a hickey."

Looking down I saw my soft cock, highlighted with a deep purple bruise the size of a dime on the tip.

"What the fuck, I didn't even know that was a thing!" I laugh.

She smiled, "It happens."

Rolling to my side and pulling her close, I kissed her lightly and whispered, "you're turn."

She smiled, "no thanks, stud. I'm going to take off. That was a good start, but I'm not trying to be a total slut this time. Gotta keep you coming back for more, right?"

I chuckled, "that will NOT be a problem."

Over the next week we definitely escalated the sexy talk over text. The fun was still there with humor and some of the in-depth stuff is sprinkled in, but we were very in to sexting now. The dating bullshit had taken the back seat and we were officially friends with benefits. The next Friday, date night, and I headed over to her house.

Upon arrival, I rang the bell and was greeted by a surprise. The roommate.

She's tall and slender, short blond hair just past her chin. She was all dolled up, looking absolutely beautiful in a skin tight black dress that highlights her subtle curves, and a solid couple inches of cleavage. Porcelain skin, light makeup, and a beautiful smile that just made me feel old. I found out later my instincts were correct. She was just 23 years old. Monica felt young at 34 to my 45, but her roommate was just a kid.

"Oh, hi Jack, I've heard about you. I'm Kelly, come on in."

"Nice to meet you Kelly, looks like you've got a hot date."

"Nothing like that, just a work dinner. I swear the doctors have me at these meetings just to give our vendors something to look at." She said with a giggle.

"Don't sell yourself short."

"Oh, I don't. I just know how it's perceived, but we all know I'm the secret weapon. Butter them up, flirt a little, and all of a sudden, our contracts look a lot better."