Before I get into the final installment of this series, I need to explain Cassie to you guys.
Carli [TS1] was a very reserved girl who became kinkier when she met me. She had very vanilla set with very vanilla guys. She loved me in her own way, but mostly she just felt safe that I could tear her up and bring her back down to Earth without hurting her.
Janie [TS2] was a one time thing.
Mari [TS3] was an old crush who gave me an oppurtunity that I ran with.
Ann [TS4] was a few week fling that burned hot then fizzled out.
But Cassie will forever be etched into part of my soul. Cassie and I dated on and off for 6 years. During most of the off time, we were still hooking up. After the 6 years, we still hooked up. We tried monogomy, cheating, polyamory, cheating on new SOs with each other, adding people. Everything.
Cassie and I could not trust each other mentally or emotionally in the slightest. But physically? That was our shit. We knew each other inside and out, better than we knew ourselves. I haven’t had sex with her in six years, haven’t seen her in five, and we could still hit all the right spots like muscle memory. If you stuck us at two ends of a pitch black cave with 1000 people, our bodies would gravitate toward each other in seconds.
Our bodies were made for each other. The rest of us just weren’t. I have plenty of stories about Carli and other girls I can post, but eventually that well would run dry. I don’t think that’s possible with Cassie.
This is going to be a long one, if only to honor Cassie in all her glory.
—
Not only had Cassie and I talked about anal, we had tried it before. About a month after I took her vaginal virginity, I got part of my head in. She tapped out and we went back to normal fooling around.
After the first breakup, we tried again. She was determined and hardheaded and ready. I got most of my head in before she passed out from the feeling.
After that, we stopped trying. We knew how to touch each other’s bodies and didn’t really need extra.
She text me asking to hang out and I said of course. After six years of an on again, off again relationship, we split ways and decided to remain friends. We were great for each other as friends, supportive even.
She comes over and lets herself into my apartment, standing in the doorway of my living room as I play through another round of Mortal Kombat. She coughs for attention, and I turn to her.
She had cut her hair to her collarbone and dyed some red into the dark brown. She smiled coyly at me, her squirrel cheeks perked up on one side, her large round eyes looking to the side as if a pose. I cock an eye brow and she laughs, all seriousness taken out of the situation.
She’s wearing some obscure concert tee of a band I still to this day have never heard of and a denim miniskirt over leggings. It was her every day fashion, but some part of my brain was still driven absolutely insane over it.
“Does Don know you’re here?” I asked.
“Of course he does. He know we’re just friends now.”
I chuckle despite the look she gives me now. He’a too afraid to put his foot down on how much he dislikes me. He doesn’t want to risk losing her.
It had been awhile since we had hooked up though
Before Don, even. I knew part of my brain was focused on wearing Cassie like a facemask, but for the most part he had nothing to worry about.
We switched the TV over to some indie film she wanted to watch and she pulled her bowl from her bag. We smoked a bit, watched the movie, and leaned on each other on the couch.
As the movie wound down, my high was fading, so I knew she was cold sober. She smoked about 10 times the amount I did. We were sitting there making fun of the movie, laughing, when she suddenly was straddling me on my lap.
She stared into my eyes, her hazel meeting my brown, searching for an answer that I must have given her, because without a word being said, our lips met halfway.
As her hands gently wrapped my jawline, my right hand unhooked her bra as my left hand went up her tee shirt, catching her small, falling breast. I began massaging her nipple between my thumb and forefinger as tiny moans escaped her lips between kissed.
My other hand found her other breast and as I worked it, her kissed deviated from my lips, across my cheek, onto my ear, and down my neck. Her nipples always sensitive, she moaned as she bit into my neck, her hips grinding against my lap.
I dropped my fingers from her tits, and slid them down her sides, before pulling up on her shirt and bra, pulling them off. She fell against my neck again as my hands wrapped around her waist, my fingers dipping past the hem of her skirt and leggings to grab handfuls of her ass.
I pulled her toward me as she grinded, wrapping my head around her, biting in her neck and shoulders in return. She pulled my shirt over ny head, and her pale skins felt warm and familiar as her tits pressed against my chest.
She slid off my lap to the floor and I helped her pull my pants off, freeing my cock, ready to greet a long lost friend. She wrapped her hand around my shaft, and opened her big hazel eyes to look at me as she licked and sucked the head.
Out of habit, I went to grab the long hair I was used to, finding nothing, and chose to run my fingers across her head, wrapping her roots between my knuckles.
She flatted her hand to my base, and her mouth followed, taking me completely inside her mouth. Her throat constricted around my cock as her togue massaged the undersidebof my shaft. She moaned and slurped as I massaged her head, pulling gently on the roots.
I turned and laid down on the couch. Without missing a beat, she slid off her skirt and leggings, and swung her leg around to straddle my head. As I gently lowered her now dripping pussy onto my lips, she leaned back down and took me back into her mouth. We exchanged moans, an oral conpetition daring the other to show how much they were missed.
As I sucked on her clit and she swallowed my cock, she bagan to moan faster. I sworled my tongue inside her as she came, her head resting on my thigh now, my cock resting against her mouth as she moaned.
She got up and turned around, throwing her leg back over my swollen dick, lowering her cunt onto it. She swallowed me and years of memories flooded back into me. Our hips matched, our rhythms matched, our bodies settled into the exact right position, a machine running on full cylinders.
She leaned across my chest and kissed me. I held her waist as she bounced herself down onto my cock over and over, me thrusting in at the exact moment she came down. She came again, squeezing my cock in her cunt. She panted against my chest, and whispered to me.
“Zee, I wanna try again.”
In this momemt, sunk deep inside her, four yeats removed from the last time we tried, I knew exactly what she was talking about.
“Let’s go to my room.”
I followed her to my room, grabbing a bottle from my dresser on the way to the bed. I laid her down on my bed, and worked my kisses from her mouth, down to her used pussy. I gave it all the appreciation I had been holding back, then put one of her legs onto my shoulder. Spreading her like this, I reached my tongue to her virgin asshole and licked it wildly as she grasped the back of my head and dug her heel into my back.
I then took the lube I had gotten from my dresser and generously applied it to my dick. I lined myself up with her asshole and very carefully slid in, pausing until she nodded and accepted me inside her.
Once I was fully in, I flexed my cock and allowed her to flex her anal muscles and grind her hips around to get use to the feeling. I took my hand that wasn’t holding her leg up and placed it on her thigh, my thumb massaging her clit.
“Holy fuck, Zee. Every time we’ve tried. It’s never felt.”
“Shh. I know.”
I slowly pulled put partly, then slid back in. I got heavy breathing and loud, drawn out moans as a response. I continued to do this, very slowly speeding up the pace each time. It was very reminicent of when I took her regular virginity.
Her other leg wrapped abound my waist, spreading herself to the best of her ability and my speed increased. I pulled out and applied more lube to my cock.
Cassie turned to her side and I spooned her, sliding my cock back into her asshole. She brought a hand over our heads, running her fingers through the back of my hair as I pushed into her. She started pushing back, faster and harder. I brought my hand around and took her whole tit into it, squeezing as she thrust against me one last time, our bodies coming together, her ass accepting my load with vigor.
We laid there for a moment before she pulled off of me. We took a shower and got dressed and decided to go grab a bite to eat, spending the night in a local diner talking about anything and everything, including what we had done.
We had no shame. We just couldn’t decline our bodies’ wish to be close to each other.
-Zee
Source: reddit.com/r/Erotica/comments/jmad93/true_story_5_mfcheat1st_time_anal69intimacypassion