The Time I Unexpectedly Had Sex With [M]y Innocent Thicc Best [F]riend

This is the story of how I somehow got to have sex with a girl I never thought I would have sex with. This is my first story, so feedback on my storytelling/writing would be appreciated! I’m going to build up quite a bit of backstory to this story to give context/build character and connections, especially for those who like that kind of stuff. For those who don’t want/need it, skip to **(. )( .)** for the action.

So we’re starting all the way back to the beginning of highschool Freshman year. I had just moved to the area recently and didn’t know anyone. One of the first people I truly got to know was this chubby asian girl. Let’s call her Lilyann. I didn’t find Lilyann particularly cute at first, but I came to grow fond of her. Her sweet, innocent personality is what caught me at first and when we started to bond over similar things, I took notice of her body. The way she kept her long sleek black hair and the way she smiled, the cute dimples. Also, her chubby body was actually kind of thiccc. She didn’t have very large boobs, but they were still sizable.

We continued to grow closer and eventually started doing this young-Freshman-idkwhatimdoing kind of relationship that eventually ended with her breaking up with me saying she wasn’t ready for a relationship. Now the important thing to know about Lilyann is the fact she is Christian girl. Not the devotee type, but just just enough to keep her from kissing or doing anything overtly sexual. Sex before marriage wasn’t in the realm of possibility to Lilyann.

Now after our Freshman year relationship-thingy, we drifted apart quite a lot. It wasn’t until the very end of our Senior year that we really started talking again. I’d thought I was over her, but I was so wrong. I definitely felt some feelings for her coming up, but I ignored them as I wanted to go back to being best friends. We kept talking more and more and grew closer even as we went our separate ways post-high school. Lilyann and I had met up a few times the following year to keep in touch but my sophomore year of university, we didn’t really get to meet up. We lived several miles apart, so meeting up was far and few. Even so, we persevered as good friends.

Come my third year at uni, I’m living in an apartment with two other guys. I’ve been swamped with studies but soon enough I finally get enough free time to spend with friends, and luckily it so happened that Lilyann was in the area. We plan to meet up in the afternoon at the beach.

At the beach, I finally see Lilyann after a year. When I first saw her, I took notice of her having slimmed down a bit. She still was a bit chubby(A part of her I actually like), but her curves were accentuated a lot more. Her tits and ass looked Much larger. We greeted each other with a hug(luckily she wasn’t a Christian side hug kind of girl). When I hugged her, it was like hugging a giant marshmallow that also had tits. I could feel her large, soft boobs press against my chest. I remember taking a big breath to calm myself to make sure I didn’t get an erection. Lilyann didn’t notice my half hard on and so we continued on with our reunion.

For a few hours we walked along the beach, catching up on everything we hadn’t been able to tell each other. We talked and talked and every so often, I got to glance over at her nice ass-rack. I mean I could tell that her boobs her big under that shirt, just the way they stood out. I kept the mentality of us being friends and nothing more. In my mind I tried not to entertain the idea of anything sexual, trying not to get my hopes up, knowing she was Christian girl

Around dusk, we decide to go to a low key bar. Knowing Lilyann, she wouldn’t want to go to a club. We get inside and I order myself a beer. Lilyann surprised me by ordering a beer herself. It was a bizarre sight, as I still held this image of an innocent girl who didn’t understand most sexual innuendos and slang. The girl who strayed away from anything to seemingly inappropriate, even if it really wasn’t.

I asked her, “Wow, you drink? Didn’t think you’d be the type.”

“Yeah I mean I’m 21, Imma drink,” Lilyann took several sips from her drink.

The night goes on and I stick to my one beer, me not being much of a drinker, but Lilyann ends up drinking 3 beers. She has the Asian Flush bad and wasn’t very good at keeping her alcohol. I could tell she was pretty tipsy. It was late and I didn’t think it best for her to go home by herself, so I took her to my apartment. She wasn’t blasted or anything, but I still didn’t want to take any risks.

When we got home I found that my roommates weren’t home, probably partying or at their girlfriend’s places. I take the red-faced Lilyann to my room and lay her down on my bed. I quickly leave the room and come back with a glass of water and have her drink it. After she finishes the cup, I take it from her then proceed to tucker her into bed. She whispers “thank you” as I leave the room. I remember as I left I took one last look at her and remembered why I had a crush on her. I go to one of my roommates’ rooms and steal a pillow and sleep on the couch in the living room.

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**(. )( .)**

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Several hours later, as I’m sleeping, I wake up in the middle of the night to a tingling sensation. I sleepily open my eyes and look up and see Lilyann right on top of me, slowly grinding my crouch. The sight of Lilyann grinding me definitely woke me up. She looked at me with a look of thirst.

“Woah what the Fuck?!? Lilyann what are you doing?” I said bewildered. My heart was beating out of my chest. I was having a hard time comprehending what was going on.

“I’m getting you ready,” she said, rubbing up on me.

I remembered she had been drunk and said in a panic, “Lilyann you’re probably still drunk, you shouldn’t be doing this!”

“I’ve sobered up. I want this.” It was dark but could tell she had an embarrassed look on her face. It was obvious to me this of course was her first time doing anything sexual of the sort, especially boldly waking me up with a grinding. As she moved her hips, I could feel her nervously shaking. My cock started to become harder and harder as she did so. Even with our clothes still on, she felt so good rubbing up on me.

“I thought you were saving yourself for marriage?”

Lilyann stopped moving her hips and looked me in the eye and said, “Yeah I decided I’d save myself for you.”

She leaned in and kissed me. I was hesitant at first but I thought to myself, “Fuck it”, and gave in kissing her back. For a minute or so we kissed on the couch. We eventually got up, still sloppily making out, slowly walking our way to my room. It was a bit awkward given I’m a short guy, standing at about 5’5” and she is several inches taller than me, but in the moment I just kissed her as passionately as I could. As we got to my bed, I turned on my bedside lamp so I could get a good view of her. Kissing her onto the bed, I got up and started undressing. I took off my shirt and revealed my semi-muscular body to her. I could feel her eyes looking me up and down.

“Before we go any further I need to confirm, is this what you really want to do?” I asked, wanting to be absolutely sure this is what she wanted.

She looked up at me and softly but firmly said, “Yes.”

“Well then, would you care to do the honors,” I said, gesturing to my pants.

Lilyann, sitting up on the side of the bed, let out a deep breath and slowly pulled down my pants and underwear. My dick at this point was fully erect, flinging out of my underwear. This was the first time Lilyann had ever seen a penis. When she first looked at it, I swear to god I actually heard her gulp. Lilyann just stared intently at my dick, not knowing what to do, so I gently grabbed her hand and led it to my dick. She softly grasped my cock and I guided her hand in rubbing it. I let go of her hand, letting Lilyann slowly stroke my cock on her own. Her warm hands wrapped around my cock made it feel as if my cock was growing even more, bulging in her hand. Lilyann just focused on stroking my cock.

After she gingerly stroked my cock for a bit, I placed my hands on her shoulders signaling her to stop, which she did. I then lifted off her shirt to reveal her bra. Her cream colored bra looked as if it was a collapsing dam trying to hold back a giant reservoir of water. She took off her pants to reveal her matching panties. I finally got a good look at Lilyann’s sexy, chubby body. She was no longer red from Asian Flush, her body and face back to being a paler color. I lean in and kiss her, reaching behind her as I did so. I fumbled around with her bra clasp for a bit, but eventually got it.

“Wow you can unclasp a bra?” she quietly giggled into my ear with surprise.

“Trust me, it has taken me awhile to figure it out.”

I kissed her into laying on the bed flat, with me on top. With her laying back, I got a great view of her breasts. My suspicions of them being large were confirmed. They weren’t the perky or overly saggy type, but they were big enough that their weight and size caused them to ever so slightly droop down to her sides. I looked at her dark nipples and then said with a smile “You’ve got some nice boobies Lilyann.” She told me to “shut up” while scowling.

I started kissing her on her neck and she whimpers. Her body tensed up. I run my left hand up her soft body, feeling every bit of her until I reach her breasts. My hand easily got more than a handful of boob. I whisper in her ear “Relax and just tell me what feels good.” She nods while biting her lip. I then proceed to start kissing her down her body, starting at the neck. While doing that, I rubbed her left nipple with my hand. I could hear her breathing intensifying. Once I reach her right breast, I start light sucking and licking it, squeezing it with my right hand. “That feels good” Lilyann said, totally trying to hold back some moans. All those years of her not doing anything sexual, building up inside her, were all being released here. Moving down, I kissed her soft stomach, burying my face in it. From there I kiss around her waist before finally planting my lips on her panties.

I licked her pussy through her panties. My tongue ran around her edges, her panties getting wetter as I licked. Once I’d thoroughly teased Lilyann, I slowly removed her panties, revealing her beautiful pussy that sat atop a Phat ass. It was freshly shaved. I suspected she’d planned this encounter from the start to some extent.

“No… don’t stare, it’s embarrassing.” Lilyann said, trying to hide.

“C’mon, it’s beautiful.”

After admiring her bulbous pussy, I got to work on it. Starting off easy I used one finger, slowly fingering her pussy. As I fingered her, I used my mouth to lick her hard clit. Lilyann’s pussy became wet, making it easy for my finger to slide in and out. I curled my finger as I pulled it toward me, rubbing the ceiling of her vagina. “I’m going to use two fingers now.” I whispered. I added an extra finger into her tight virgin pussy. I fished around, seeing where she reacted greatest to my fingers. I eventually found the spot, twirling and curling my fingers. Lilyann fidgeted about from the feeling going on inside her for the first time. Once I heard her start moaning more and louder, I quickened my pace. She was close.

“Oh my gosh, Cain this is-” Lilyann strained to say. She clutched the back of my head as she came. Her body twitched as she finished. I pulled fingers from her pussy and they were soaked. I was actually surprised I got her to finish on her first time. Lilyann laid there on my bed panting, trying to catch her breath.

“So how was that?” I asked with a smile.

“Incredible,’ Lilyann replied breathily. Lilyann then got up, sitting upright face to face with me. “I want you to… fuck me.” She was nervous about it, shifting her eyes about.

“Ok,” I calmly said, placing my hands on Lilyann’s shoulders to reassure her.

Leaning over the bed into my nightstand, I pulled out a condom. I tore off the wrapper, throwing it away, but before I put it on I looked up at Lilyann with a sly smile and asked, “Lilyann do you know how to put on a condom?”

“Yeah of course” she replied flustered. I gave her the condom to prove it. She proceeds to roll the condom the entirety of my shaft and then looks up at me with a smug look.

I look down at it and say, “Nice try, but…” I tug at the tip of the condom so there’s a reservoir above the tip of my penis. “Need a place for the little guys when they come out.”

“Woops Sorry…”

“It’s ok, gotta learn sometime. Now lay back,” I told her. Lilyann laid back down on the bed and I readied myself to enter her.

I rub my cock up against her still wet pussy, teasing her. “Here I go…” I then slowly insert the head of my cock. Lilyann tensed up from nervousness. I told her to just breathe, relax, and to enjoy the feeling. Slowly, inch by inch, I push my cock deeper into her tight pussy. Lilyann clenched the bed sheets with her hands. She closed her eyes, taking deep breaths in and out. Her pussy embraced my cock as it slowly entered her. Her vagina seemingly tightened up more as soon as I was ¾ in, so I stopped. Slowly, I thrusted in and out. Her shaky breathing could easily be heard.

I looked up at her, gazing into her eyes. I got even hornier from the look of her moaning face. My cock was hurting from how aroused I was. My hands found their way around her waist, assisting me as I pumped. Lilyann’s ass every so often grazing my hands. I kept a slow pace, thrusting in and out, each thrust deliberate. Every push in, she let out a stifled moan. I felt as if I was in a dream while fucking her. I leaned forward to kiss and fondle her amazing tits. That feeling of her big tits in hands was heavenly. Her breasts squeezed through each of my spread fingers. I kissed her harder while continuing to fondle her breasts. I can feel my self edge closer to cumming. I wanted to last longer, to try and see if I can get Lilyann to orgasm again. I pulled out and pinched the head of my penis to edge myself, allowing me to last longer.

“How are you feeling Lilyann?” I asked shakily.

“Good. Put it back in, I want to feel you more,” she whispered in my ear.

I obliged, inserting my cock once again into her. Slowly, I fuck her again. Her warm insides helped my cock get back any hardness it lost from being pulled out. I laid forward on top of her, so her breasts pressed against my chest. The feeling her marshmallow breasts got me excited, causing me to start thrusting faster. Lilyann closed her eyes, moaning. She clutched onto my back with both hands. Her moans grew louder and louder as I fucked her. With each breath, I thrust in and out. I felt myself ready to cum. I moaned “I’m going to fucking cum.” The feeling hits me, and I cum inside her. My dick is pulsating and twitching in her pussy. After I finally stop cumming, I quickly pull out, slide off the condom, and tie it off. I look over to Lilyann who is glistening with sweat, panting.

She looks at me with glassy eyes, panting, “I’m so close, please keep going.”

I nod and hastily shove my raw cock in her without thinking about the consequences and fuck her again. Wanting her to finish, I rub her clit while fucking her pussy. I saw her tits bouncing and aggressively grabbed one with my free hand. My cock slid in and out effortlessly, making fucking her easy. Going raw inside her pussy, was an incredible sensation. As I fucked her, ripples went up her thicc body. She gripped the pillow behind her head. Her moans became more high pitched. The whole image of her body was sexy. Soon enough, Lilyann’s body shivered and she let a loud whimper. I slowly pulled out my cock and sat down on the bed exhausted. Lilyann had a huge smile of satisfaction. I pulled her up towards me and kissed her.

“That was amazing Cain,” Lilyann said, giving me a hug.

After that, we got cleaned up and then laid in bed next to each other naked. We playfully talked a bit before we eventually fell asleep. When I awoke the next morning, I got to wake up next to her cute, round sleeping face.

Source: reddit.com/r/gonewildstories/comments/hc5lp8/the_time_i_unexpectedly_had_sex_with_my_innocent