I [M33] took the virginity of a 26 year old woman | 2016

Backstory: Her name is Sophie and she's Vietnamese but born and raised in Canada. I used to work with her, over a year ago. I was the rough and tumble warehouse manager and she was the polite, bashful office girl. We had a semi-flirtatious friendship in the work place, but it was limited by her shyness. She was extremely introverted and self conscious. I knew she was attracted to me but I'm not sure if she knew how attracted I was to her (I fantasized about fucking her constantly). She was a full figured girl. Not fat but very thick, about 5'2", she had enormous tits and a pretty (though bookish) face. None the less, she was very insecure. Every time I talked/flirted with her she would get nervous and stumble over her words. Her face would get red and she was visually intimidated by me, so I made an effort to not come on too strong. She seemed like she lived a very sheltered life. It was hard to get to know her. After working together for 2 years all I knew about her was that she loved to read and loved to shop.

After I quit that job we stayed in touch via goodreads, of all places. We messaged each other continuously and eventually she started to open up. She told me she's only had one boyfriend and she's always felt awkward in her own skin, especially around men. She got more comfortable with me over time though. The conversations eventually became more and more sexual. So much so that she revealed to me that her cup size was 38H and I revealed to her that I had a 10 inch cock. Knowing this we started telling each other more of our sexual desires; How she's always had a thing for big cocks, that she owns several large dildos and masturbates a lot. I told her that I've never fucked a girl with massive tits like hers and that I always wanted to fuck her. We even exchanged some revealing photos, but eventually our communications dwindled. There were a few attempts to meet up but plans fell through (my fault), I started seeing someone and eventually we stopped messaging.

2 Weeks Ago: I was driving home. It was a wet and windy, a humid day and I noticed her walking from the bus stop (caught in the rain). I recognized her from behind instantly by her amazing figure and her ponderous way of walking, so I pulled over and offered her a ride. She got in and, right away, the atmosphere caught us off guard. It was awkward at first but I kept making small talk to ease the tension. I was leaning back in my seat, secretly trying to get a good look at her through the corner of my eye. It had been so long, I couldn't help it. She was wearing a very tight fitting yellow top made of soft fuzzy cotton, it was speckled with rain drops and her nipples were visually hard through the fabric. I could see the seams of her bra through her shirt, straining like they were about to tear apart from the weight of her hefty bust.

Amidst my small talk and frequent glances I noticed she was glancing too, directly at my crotch. Looking down at myself I saw that, as usual when sitting in a car seat, my jeans had become tight around my crotch and I had a sizable bulge showing. Feeling her eyes on me excited me and, remembering our goodreads conversations, I began a conversation with myself in my head; Debating whether or not I should say what I really wanted to say and finally I blurted it out, "You should come over".

"Ok" She said timidly.

As I lead her up the stairs to my apartment I could feel the tensity mounting with each step. We got inside my apartment and both sat next to each other on the couch. An excruciating silence set in and I knew if I waited any longer the moment would be lost in her tenseness so I told her she should sit in my lap. "Ok" she murmered and she sat sideways on my lap.

"No. Facing me" I said and she shifted so she was straddling me with her legs and we began making out. At first her lips were moving too fast and I told her twice to slow down. Finally she did slow down and our lips began working together in cooperation for 5 minutes or so.

My cock began to swell beneath her as I lifted her top over her head revealing a lacy baby blue bra with wide, heavy-duty straps that were digging in to her shoulders. I took my shirt off too. She breathed in and my eyes blurred and then focused on the depth of her cleavage as her chest rose. I kissed along her neck and collar bones. I began making a track of kisses across the upper part of her breasts that spilled out of her bra. I moved my hands down her back and past the elastic of her leggings, gripping her ass and pulling her into me before sliding my fingers back up to unhook her. She wriggled and shuffled herself free, revealing her caramel colored tits (imprinted with the lines from her bra) and her large, supple, slightly shiny nipples, only a shade darker than the rest of her skin. I leaned back in the couch using my knees to push her in to me and as I did, I felt the weight of her giant tits on my chest, her nipples touching mine. She held her breasts in her hands and pushed them up to my mouth and I devoured them as she let out a soft moan and began grinding her pussy against my ever-thickening cock. Her head swayed backwards as my tongue circled her tender and now hardening nipples. Trading them between my mouth and fingers. Pulling them in to my mouth with my lips, sucking on them slowly, savoring the sweetness of her clammy skin as I felt the weight of her stunning tits in my hands.

I must have spent 20 minutes enjoying the biggest tits I'd ever seen (the ones I'd fantasized about so many times), her moans getting louder and more animated as the moments passed between making out, squeezing, caressing and sucking.

At this point I was ready to pin her down and fuck her, but still not wanting to frighten her, I carefully slid a finger into her waistband and with a gentle tug I told her to take them off. As she stood up I removed my jeans leaving only my thin boxer briefs to try to contain my large swollen bulge. I watched in amazement as all of her beautiful body came in to view. She slid her leggings and underwear down slowly with a bashful look on her face trying to avoid eye contact, and I swear I saw a thick stream of slimy liquid fall from her delicate pussy with her panties as they fell to the floor. "I've never slept with a white guy before" she said nervously.

I took my, then mostly-hard, cock out of my briefs. It was already percolating a steady drip of precum, as it usually does when I'm this turned on. I stroked it a few times in front of her as she got on her knees. I was expecting to have to instruct her further but almost as if she couldn't control herself, she bundled both of her hand around it and looked at it in awe as she took over stroking and squeezing. I stiffened from her tugging and leaned back further, pushing my cock towards her as she said "I've never slept with anyone this big either" with a shocked, apprehensive look on her face.

"Take your time" I told her, and with that she began sucking on my thick knob.

"Mmm" she moaned as she sucked the sweet precum out of my dickhole. Soon she was slurping all over the head, trying to get her mouth around it and drooling all over it. I was thinking I'd have to coach her through this too but something came over her at this point and she started cramming my rigid cock down her throat. Taking all that girth with enthusiasm. I guess she'd been practicing on those dildos because she was steadily pressing most of my cock in and out of her slippery throat for a good while before I told her to stop and let me fuck her tits.

"I've never tittyfucked before" she told me as she took her heavy tits in her hands (barely able to keep a grip on them due to the sheer mass of them) and squeezed them around my cock "I've only seen it in porn". Well she must have learned something because she immediately began spitting big gobs of clear spit onto the tip of my cock as she moved her tits up and down on it and a mischievous grin came across her face for the first time since I'd met her. Her pink lips glistened with saliva and it dripped down her chin as she jerked me off with her H-cups, nipples fully hard now and glistening with a crazy amount of her own spit. Her mouth seemed to be watering uncontrollably. Her forehead was now a bit sweaty and her baby hair was sticking to her skin. "Oh my god. How big are you again?" she asked still smiling with my cock reaching it's full potential between her cleavage. I told her my size again and she moaned and began bouncing her tits more vigorously with excitement, causing me to get even harder.

I asked her how wet her pussy was and with her new found confidence she reached between her legs, my cock still resting against her sternum, and came up with two dripping wet fingers. I motioned towards them and she put them in my mouth just as her warm juices were beginning to drip down. The taste of it was tart but at the same time sweeter than any pussy I had tasted before. I couldn't take it anymore. My cock was about to shoot through the roof, so I put my hand around her throat and carefully pushed her back until she was laying flat on the floor in front of me.

She spread her legs and I saw how shiny and wet her little simp was. Her inner labia was protruding slightly and her clit was large and bright pink. I started to slowly lick up the juices from her outer labia with a broad tongue, then sucked the rest of her pussy clean only to see it quickly soak itself again. Her chest rising and falling rapidly as she breathed, her pussy streaming around my lips and tongue. After edging her gently for 10 minutes I knew she was ready for me.

Kneeling in front of her, my cock was standing straight up, aching with my pulse. I took a moment to admire the sight of Sohpie, the once so timid girl from the office, naked, flat on her back, colossal breasts towering on top of her, wet pussy trickling on my living room floor.

My cock was painfully hard now, still glossy with spit and precum as I leaned back on my knees and she began tugging on it again with both hands, like it was a warm slippery fire pole she was trying to climb. I licked her juices from my lips then pressed the underside of my shaft against her swollen pink clit and began sliding it up and down. I made sure she could see the length of it against her firm but soft stomach and I saw an "oh my god" look come across her face as she tilted her head back and I started to penetrate her. Slowly at first, it was a bit of a struggle to get the tip in, but we both let out a sigh of relief as my thick dickhead breached her opening and a few inches fell into place with ease. I began pumping slowly and she was gripping her tits like she was dangling from a cliff and they were the only thing to hold on to. Gasping and yelping she yelled out "fuck me with that giant cock!" as if she was reenacting something she saw in a porno. I leaned into her and I sunk a few more inches into her. She let go of her tits and braced herself with her fingers spread on the floor and her gargantuan breasts pooled off of her chest and rested in the crevass created between her arms and her torso. Her stiff satin-like nipples were staring up at me as they moved in circles.

Her body began shaking as my thrusting became more and more violent, her mountainous tits swaying more and more vigorously with my movements. She was reaching her arms out above her looking for something to brace herself on. She finally gave up reaching and her hands settled on my chest for support. Soon I was fucking her at full speed and she was taking the majority of my cock. As her shaking became uncontrollable and her pussy spilled a gush of hot juices on my cock and around her neatly trimmed pussy lips, forming a pool on the floor beneath her. I continued pounding my strong erection in and out of her until she came several times with loud cries of pleasure.

She let out a long ear-splitting scream, panted a bit then giggled "oh yes" as I flipped her over and positioned her on her knees in one fell swoop not skipping a beat. I continued fucking her from behind harder and harder until, leaning back and bending my cock downward, it looked like she was taking the whole thing. I couldn't help but notice our reflection in my sliding glass door and how huge her tits looked as they hung there, swinging in the air. I started rubbing her butthole with my thumb and eventually slipped it in and splayed my fingers across her lower back, using it as a grip while I continued thrusting. I admired the view of her meaty round ass as she began bouncing herself back and forth on me, her chubby little pussy distended around my throbbing thickness, and pouring watery rivers of pussy milk around the edges, trickling down my balls and on to the floor.

Finally she collapsed my thumb still in her ass and I pushed her down into the floor with my palm. Then I grabbed hold of her ankles, bending her at the knees and spreading her legs. Her tits were cushioning her against the floor and exploding out the sides from under her body as I pounded my cock downwards into her now steaming hot hole.

"I want your cum!" she managed to say amidst her screaming (again sounding like something she learned in a porno). Hearing this once innocent, reserved girl, who I'd been dying to fuck for so long, say she wanted my cum put me over the edge. I might have been able to go longer but it had been almost an hour now and I gave in to my urge to cum.

Flipping her over as my massive pulsating cock sprung free from her pussy with a sloppy gush that emptied down her thighs, she faced me just as the first streams of warm cum began flowing from me. She caught the second stream in her mouth as I took aim and drenched her tits and face. On my knees, I continued cumming for what seemed like forever as her body laid trembling beneath me. She was covered in it, completely drenched in my hot load, glistening and panting, and on the verge of tears. All she could say was "oh my god, oh my god" barely able to speak, she kept repeating it for a few minutes before she managed to get to her knees. Still shaking she got up and went to the bathroom, legs wobbling and thighs spazming as she walked with her hands stretched out in front of her as if she couldn't see. She seemed genuinely worried for herself, caught off guard by how weak he body had become in the wake of her orgasms.

After cleaning up, she came back and sat down looking shy again and nervous. After talking for a bit about how amazing it all was, she confessed that she was actually a virgin. I acted surprised but I kind of figured she might be. I said "no, you're not. I just fucked the shit out of you" and she started laughing.

The next day she sent me pictures of her pussy, still swollen and red and the rug burns on her knees. I sent her pictures of my cock and the nail marks she left on my chest, along with a message tempting her to come over again. She did and we did it all over again.

So yeah. That's the jist of it. Thanks for reading. If you like this story let me know. I've got a few more.

-Jinx