[MF] I got to fucked my best friend and lose my virginity soon after she broke up with her boyfriend

I like some backstory and I know quite a few other people do too, so I’m going to give context and lead up in this story. Those who don’t want to read that, skip to (. )( .) for the action. [Also just so it is clear, we were both 18 by the time of this story].

So the girl in this story, let’s call her Amelia, I met the beginning of our Junior year of high school. We bonded very quickly and soon became best friends. Even from an early point in our friendship, we were pretty open about things with one another. We learned quickly about our interests, wants, and desires.

Now Amelia is a cute Filipina girl, round face, big boobs and a nice ass. These boobs of hers are the type that were visible even when she wears a sweatshirt. To say the least, they are fairly big. She is also a short girl, shorter than me and I’m 5’5 (I’m sure she is like 4’10). Because of that, her big boobs look even bigger on her. One of the hottest things I found about her, besides her boobs, was the way she did her hair. I’m sure there’s a name for the style but I don’t know, so I’ll just have to describe it. Amelia likes to have it where most of it is kept up in the back but she lets two short strands drape down on the sides of her forehead(I guess like two bangs). I’ve always thought that was really hot.

Now Amelia had a few previous boyfriends before she met me. When we first became friends, she was just getting into a relationship with some guy on Tinder. (I saw her Tinder and she got like 500 matches in three weeks. She was very picky too from what I saw, only swiping on good looking asian dudes). I actually met the guy she matched with and we hit it off. We funny enough became good buds, not best of friends but good enough that we were comfortable talking with each other. So the months go by and one day after class it’s just us talking in this one classroom. I noticed she’s been in a good mood the past couple weeks, always smiling when texting or talking to her boyfriend. I asked her why she’s been cheerful lately.

“I’ll tell, but you’ve got to promise not to tell anyone!” she says smiling.

“Yeah sure of course, I won’t tell.” I was pretty eager to hear, me being a nosey type of person.

“I had my first time with my boyfriend!” She said with a gleeful smile.

“Oh shit. Damn you’re now in a different league than me.” I said surprised. I felt a bit envious of her boyfriend. I was still a virgin at that time and was itching to not be.

Amelia didn’t go into detail but I got gist that they fucked. Us being pretty open, I actually ended up hearing her boyfriend drop it into a conversation all three of us were having at one point. We were all just chill with one another. Though I saw him as a bro, I just wished I was in his shoes. Although I’d have given anything to fuck Amelia at that point, I didn’t want to risk tarnishing the good friendship we had. I ended up telling myself that I should choose to remain friends with her.

So nothing really happens for the next couple months until near the end of first semester of Senior year. I’m sure Amelia and her boyfriend had sex a few more times in those months. I honestly thought they’d be together for a lot longer, but after a little under a year into their relationship they broke up. I never really got the details of it, but from what it seemed Amelia was just frustrated with him and didn’t want to talk. Even though I was secretly happy inside myself, I was a friend foremost and comforted her when they broke up. She told me she appreciated my support and that I was a good friend. That kind of rubbed in the direction that I was “just a friend” and that there could be nothing more, but I was already content with being to be a good friend of hers.

We continued on into the winter break, continuing to openly talk. Though we always had these open discussions about sexual stuff, I always found it kind of odd/funny that it was normal we had such conversations so casually. At times I even talked to her about how I felt I lacked confidence to talk to girls. She told me that someday I’d find a girlfriend. I still thought to myself at the time that it’d be awhile for me to have a girlfriend and then even later to not be virgin anymore.

Now sometime during the beginning of second semester, we’re lazing about in our homes and texting. We start talking about dirty stuff like pornos or sexy reddit posts we saw earlier. Amelia goes on to tell me that she missed being able to cuddle with someone and fuck. She explained she missed it for the past month. I rebuke by reminding her she’s lucky she even had someone to love her. Amelia asks if I’m upset about being a virgin, which I confirm in an angry manner. Several minutes pass by and Amelia hasn’t responded. I think this is weird but don’t think too much about it and continue on with what I’m doing. Amelia eventually responded and this is what our conversation was like:

Amelia: Do you like me?

Me: Like you, wdym? Ofc I like you. You’re one of my best friends.

Amelia: Mmm not really what I meant. Do you think I’m attractive?

Me: I mean sure, you’re a cute person. I may be your friend, but that doesn’t mean I can’t see you as attractive.

Amelia: Can I ask a crazy question?

Me: Mm I’m afraid of what it could be but sure…

Amelia: Would you fuck me if you could?

I thought this over before I responded. At that time I really just wanted to maintain our friendship, but I didn’t want to have my feelings for her be constantly hidden and hanging out in the back of my head all the time. I decided to be honest and tell her exactly how I felt about it.

Me: Once. That isn’t because I’m Not attracted to you, because I really do find you cute. It’s just I want to keep our friendship. I truly value the friendship we have right now. I’ve always found you quite attractive and have had some desires to fuck you. . Only once though. to stay friends.

Amelia: I see…

The conversation seemingly ended there, me not wanting to really continue on with the subject. I honestly felt like I fucked up in that moment, regretting my text. But Amelia responds a few minutes later:

Amelia: What are you doing Friday?

Me: Uuh idk, but probably nothing.

Amelia: I was wondering if would you like to have sex with me with Friday…?

Me: Mmmm what…?

Amelia: My parents are out this weekend, and I was wondering if you’d like to have sex with me then.

Me: Are you being serious rn. I can’t tell if you’re messing with me. If you are, that’s fucked up.

Amelia: Cain, I’m being serious. I want have sex with you. Just this once ;)

I’m honestly taken back by this. I struggled to form thoughts. I nervously replied that I’d like to have sex with her. She replied back happily, and told the details to come over at 8pm on Friday. After that we ended the conversation. The next two days, I’m a nervous wreck. My conversations with Amelia were a little scary and a bit awkward, but interesting. Amelia explained to me that she had been wanting have sex for awhile, but sex with someone she was comfortable with and so she thought of me. She explained that she thought of me because she thought it best to fuck someone she knew. She also said that I looked kinda cute. This made me ecstatic. I was calmer about the whole thing after that.

Not wanting to fail at sex, I admittedly looked up guides on first time sex when I got home. They gave me general tips on what I should do and things like lots of foreplay. I even looked how to do oral as it was a part of foreplay and I wanted to make sure Amelia felt good too. After I’d looked at tips, guides, and forum discussions, I felt a bit more confident. I knew I wasn’t a pro but I had some basic knowledge.

Friday comes around and I’m shaking non-stop. I can’t but help think of the worst possibilities to come of this encounter. I’m a pessimist, so I imagine the worst scenarios in my head making things worse. Amelia and I say our goodbyes after school and go about our after school activities. When I got home from practice, I ate dinner, showered, put on a slim button down shirt to accentuate my physique and some nice looking shorts. I got my hair all done, thoroughly cleaned my mouth, deodorante up, and grabbed my car keys. I said goodbye to my parents, who thought I was just spending the night with friends, and then drove off to Amelia’s house.

(. )( .)

I nervously rang Amelia’s door. I heard the quick shuffling of small feet. Amelia opened the door and greeted me. I saw she was wearing her regular t-shirt and some baggy pants, which covered up her curvy figure. I entered the house and took off my shoes. Amelia and I stood there awkwardly at the door, waiting for the other one to say something. My hands fidgeted about, me not knowing what to do with them. She ended up timidly taking my nervous hand and guided me to her room. We reached her room and I saw it was white with a big bed with poofy white comforters. She closed the door behind us and then held both my hands.

“Are you ready?” asked Amelia.

“Yes,” I replied with a shaky voice.

She leaned forward and kissed me. For the first time I felt the soft, warm lips of a girl against my own. Amelia, in between kisses instructed me on how to kiss, I made sure to follow what she said.

“Don’t open your mouth too much”

“Relax your lips a little”

“Hehe come closer,” she giggled. “Nothing to be scared of.”

My hands instinctively moved around her waist, pulling her in close to me. Lighty, I ran them around her back. Amelia replied by wrapping her arms around the back of my neck, pulling my lips against hers more. A loud *Click* sound was heard each time we pursed our lips together. I plopped down on the side of her bed and she climbed on top of me, stradling me. Amelia started grinding up against my growing erection. I move my hands down to her ass and grab it, guiding and groping it as it grinded up against me. We are making out for a bit before Amelia starts unbuttoning my shirt. In between each kiss, she does a button. She slowly moves down my shirt, carefully undoing each one. Eventually she undoes the last button and I take off my shirt, unveiling my muscular body which she’d never seen before. I can feel Amelia’s hands running over my body, feeling up my muscles. Amelia stops kissing me and removes her shirt up over her head.

I see her tan colored bra holding her breasts, popping out right before my eyes. I have this image of the typical Filipino skin tone, but I don’t know the words to properly describe it. Amelia had the lighter skin tone of Filipinos. Almost like a praline, tan color with a warm undertone.

Slipping off her pants, I got a good view of such an amazing body. I was mesmerized by her half nakedness. After removing her pants, she looks up at me and she notices I’m staring at her breasts and grins. Amelia moved off of the bed, kneeling on the ground facing my crotch. She ties her hair up in the cute manner I talked about before. Strands of her hair, draping down on her forehead. I remember how fast my heart was racing at that moment. It was ready to leap out of my chest.

“Let’s see what’s under here,” Amelia said undoing my pants. She slowly unzipped me. Pulling off my pants and underwear, Amelia revealed my already hard cock. Amelia admired it, holding it to her face. With her right hand, Amelia slowly stroked it. Gently she motioned it up and down. I was taken back by her holding my dick in her hand, my body nervously trembling in anticipation. Never before had someone else touched my dick and here was Amelia softly massaging it.

“Muscles and a big dick, I should’ve of been fucking you long ago,” Amelia giggled, proceeding to put her mouth on my dick. Her pink lips encircled my cock, passing over the head as she went down. I saw half of my dick disappear into her mouth before she slid her mouth back up. The head of my dick was, what I presume, hit the back of her throat. That feeling of her mouth on my cock got me going. My dick felt a tingling sensation as she sucked and licked. Her warm mouth and tongue whipping around my dick was fucking amazing. I moaned as she continued, my cock experiencing so many different sensations.. While she sucked, I admired her cute face and fantasized about what hid behind that bra of hers. Amelia’s eyes looked up at me as if they yearned for my cock. Amelia used her hand to play with my balls as she sucked. Massaging them very softly and with care. She lathered my dick with her saliva as she blew. I could hear her slurping as she sucked me off. Her head bobbed as it went up and down. My cock disappeared and reappeared behind her lips. After what seemed like a blissful eternity, I told her to stop, telling her that I didn’t want to get too close to bursting before penetration. She nods, stopping.

“I’ve noticed you’ve been admiring my boobs. You want to see them?” She asked with a smooth smile.

I nodded.

Amelia then reached back and unclasped her bra, throwing it to the side, letting her breasts fall out.

I wouldn’t say her boobs were perfect, but more like they were gifts handcrafted by God! (It might just be me, but I thought they were something special). They were those nice teardrop shaped breasts. Her nipples looked small compared to her large boobs. I looked at them with a smirk on my face, ready to just feel them up. My dick was aching just looking at them.

“Here,” said Amelia, taking my hands and placing them on her tits. She moved my hands around her boobs, massaging herself with them. Her tits made my hands feel so nice. When I fondled them, I felt my fingers sink into them. They jiggled about as I played with them, moving about but retaining their shape. Excitedly, I squeezed a little too roughly causing Amelia to yelp.

“Eek! Gently. Gotta be careful,” yelped Amelia.

“Sorry!” I apologized immediately.

“You like them don’t you?” smiled Amelia.

“Fuck yeah, they’re amazing!” I said with a big grin.

I tenderly played with her breasts some more, bouncing them around in my hands. Jiggling and squishing them with my hands. They were like squeezing a somewhat firm marshmallow. I rubbed Amelia’s nipples a little causing her to shudder.

“I think it’s time for a little something for you.”

Grabbing Amerlia, I flipped her around so she laid on the bed while I was on top. I kissed and nibbled her left tit while I continued fondling her right. I was making sure to enjoy myself with her boobs. Amelia moaned. With my fingers I teased her nipples as my mouth moved down her. Gently I rubbed and pinched them. Moving down, I kissed her body until I reached her pussy. Remembering what I learned online, I first kissed around Amelia’s panties, teasing her. I could hear her breath, waiting in anticipation. Once I had teased her enough, I removed her panties revealing her beautifully smooth pussy. I kissed her pussy’s lips, hoping to teaser her some more. Opening my mouth I began licking her pussy near what I believed to be her clit.

“Cain you’re not really hitting my clit. Peel my vagina open a bit and aim a little higher,” explained Amelia.

I looked down embarrassed, I felt my cheeks turn red. I proceeded to pull aside the sides of her pussy. Now I could more clearly see a lil bump at the top, which I guessed was the clit. My hands grabbed handfuls of her ass as I buried my face into her. Using my tongue I focused on that spot. Slowly licking up and down, I pleasured her clit. I made sure to use both sides of my tongue, providing different sensations. I felt a hand on the back of my head and some more moans. At that moment I just thought: “I guess there are some things you can trust on the internet.” Wanting to keep her climbing the mountain, I focused her clit more, moving my tongue up and down faster. Amelia’s body tightened and shivered, her hand on the back of my head clenched my hair. Her breath was stifled with the stroke of my tongue.

“Wait…” said Amelia, stopping me mid lick, pulling my head away from her pussy. “Let’s save the rest of the fun for the real stuff.”

Amelia scooted across the bed to her nightstand and pulled out a condom from one of the drawers. She fitted the condom on my cock and pulled me on top of her onto the bed. I looked down at her and smiled, then kissed her on her soft lips once again. We kissed some more before she asked if I was ready. I nod and she guided my cock into her. The tip of my dick hovered around the entrance to her. My heart began to race. Amelia pulled me inside of her. A sudden soft warmth enveloped the head of dick as I first went in.

“Ugh that already feels good,” I moaned.

Amelia giggled, “It gets even better. Just don’t shove it in.”

I nodded and proceeded to push in slowly, but Amelia let out a cry of pain.

“Wait wait!” yelped Amelia in a panic. “Wait, you need to do this slowly. I can’t take you all right now. Just the tip for now.”

Amelia was taking deep breaths as I moved back and forth with the head of my penis. Bit by bit, my dick was able to go deeper into her. As my cock penetrated deeper and deeper into Amelia’s vagina, there was a pleasant sensation surrounding it. Soon enough all of me was inside of her. As I pushed in, I gazed at Amelia’s face and brought mine to it. In and out I thrusted while we kissed. Our lips brush against one another, then pressed firmly together. Pushing my tongue out, Amelia wrapped hers around it. All the while I felt the texture of her pussy. Every once in a while I would glance down and stare at her boobs bounce about, almost entranced by them. I brought myself closer to her, so her boobs pressed against my chest. When I pumped in and out her boobs jiggled, caressing me, turning me on even more. The embrace of breasts like hers was so arousing. Her pussy at the same time hugged my dick, pulling and holding me in her. Its pleasant wetness made my cock twitch within her, which in turn made her moan. I kept feeling the head of my dick tingling from the pleasure. Back and forth my hips moved, slowly moving, making sure not to hurt her.

“Is this good?” I breathily asked.

“Yes..” Amelia softly moaned, “keeping going like this, it feels good.”

Taking action, I pinned her arms over her head. Wanting more of her boobs, I traced my right hand down her body and cupped her right breast. Holding her hands up with my left, I squeezed her breasts with my right. I pushed in harder and faster into her, grunting with each thrust. My body moved like a wave, starting at my chest then rolling down to a pump. All the while, Amelia was letting out cries.

“Mmm.. Yeah fuck me harder…” begged Amelia.

We continued like this for a while. Push in and out of her, kissing more and more sloppily. I lost track of time as we fucked. At one point my core started to burn. It hurt but the stimulation going down in my cock was too great to stop fucking Amelia. I kept going, holding by underneath her arms and pulling her into me. Amelia held onto me and let out stifled moans. On my back I could feel her hands digging into me. Both of us were breathing heavily. Our mouths continued to connect in wet kisses.

I then pulled myself from Amelia’s lips. Holding Amelia by the waist, I flipped her around into doggy. I grabbed her ass cheeks and used them to pull her towards me each time I thrusted. Ramming my dick into her pussy, Amelia’s thicc ass cheeks clapped against me. She panted and moaned, and I just kept thrusting into her. Her breathing sounded stifled, probably from her body being jerked back and forth.

“Oh yeah keep that up,” whimpered Amelia.

She clutched the bed sheets with her hands. Her eyes were closed shut and her mouth was wide open. Eventually I started to give out. My core was killing me.

“I can’t… keep this up. My body is failing me,” I heavily breathed. I pulled out of her and fell down to my side on the bed next to her. My body kinda collapsed a bit from exhaustion. Leaning in, I kissed Amelia some.

“That’s fine. We’ve been needing to switch it up a bit,” Amelias said, licking her pinkish lips.

“Sit up over there.” Amelia pointed to the head of the bed. I crawled over and sat upright, resting my back on the headboard. Playing with my cock, I beckoned her. Amelia crawled after me, biting her lip. She had a look of lust in her eyes.

“Time for me to be a cowgirl,” smiled Amelia.

She positioned herself over me, sitting on her knees. Grabbing my cock, Amelia slowly lowered herself onto me. Once again I saw my dick get devoured by a pair of puffy lips. Amelia shifted around on her knees, shimmying down. When Amelia descended onto me, it felt like she was tighter. As my dick went deeper, there was more and more resistance and it felt even more tight.

“Damn what the fuck. You feel so tight,” I said straining to get it out. Amelia just smirked at me. Her face, a mix of concentration and pleasure.

My cock was being gripped by Amelia’s vagina. I just remember it felt like there was some kind of suction sucking me in and out of her. Positioned over me, Amelia proceeded to bounce up and down on my stiff cock. A loud clapping sound could be heard when she landed on me. Up and down her tits went. I buried my face in between her boobs, they pressed softly against my face like two warm pillows. On top of that I made sure to play and massage them some more. Amelia continued to let out audible moans as she rode me. She had her eyes closed and her hands on my shoulders. I felt the texture of her pussy as she bounced up and down. The movement of her hips and her cushioned ass were incredible; the weight of her body slamming down on me. Relinquishing her boobs I went for her ass, grabbing it hard. Sinking my fingers into her ass cheeks, I aided her in her ride. I lifted her up and slammed her back down. Amelia held the back of my head while she kissed me, moaning while we frenched. My body was being overwhelmed with sensations.

“I think I’m going to cum soon,” I grunted.

“Ugh.. where… Do you-” Amelia gasped in between each of her words as she bounced. “Want to cum?”

“Fuck… I don’t know,” I said breathily.

“My chest?”

“Yea, yeah.”

“Ok, stay right there,” grinned Amelia. Once she landed down on my dick, she stopped bouncing and slowly pulled herself off. When she got off, my stiff cock slung back, slapping my stomach. I quickly ripped the condom off.

Amelia proceeded to lay down on her stomach facing me and wrapped her boobs around my dick. At that moment I realized what she was doing, suddenly becoming very excited and even more aroused. She lubed up my dick with her saliva, rubbing it in with her breasts. With her hands she squeezed her plump breasts together, creating a tight grip around my cock. Her boobs moved up and down replicating the feeling of me being inside her pussy. The head of my cock poked out from her cleavage. Amelia licked the head of my penis, using the point of her tongue to massage the tip and rub underneath the sides. She was reaching all the sensitive parts of my dick. On my cock I could feel the smooth upward motion of her boobs rubbing upward every inch, and then a tight pull down. Amelia then started to shake her boobs about quickly, rubbing my dick. My dick was starting to pulse and throb. She must have noticed my cock twitching and massaged more vigorously, shaking her tits faster and sucking more.

“Shiit I’m cumming,” I said very out of breath.

“Cmon let it out on me,” purred Amelia.

I violently gripped the sides of the bed and let out a loud moan. I came, spurting thick cum all over her breasts. It felt like a big tension was being released from my dick. Enough pressure was built up that my cum shot onto Amelia’s face. Her lips and nose got a few white strands of cum strung on them. I saw her boobs were just covered in my jizz.

“Wow you came a lot!” said Amelia with wide eyes. She wiped some of my cum from her tit with her finger and admired its stickiness between her fingers.

“That felt amazing,” I said in a daze. My mind was buzzing from what had just gone on.

“I’m glad your first time was so good.”

Gaining a hold on my senses, I had suddenly remembered that Amelia needed to orgasm. I felt obliged in that moment to help her.

“Oh I need to help you finish!”

“Oooo, ok then how about you eat me out some more,” Amelia said with a coy smile.

“Alright but uh before I start don’t you want to clean yourself up?”

“Naw it’s fine. It’s not bad and I wanna keep this moment going.”

“Mkay.”

Amelia scooted to the edge of the bed and laid back.

Hopping off the bed, I got into position. I placed my lips on her pussy and became kissing. Kissing all over, I had made sure to touch every inch of her bottom. With my tongue I ran up and down her pussy, stroking up with the top and stroking down with the bottom. My tongue continued to licked her pussy over and over. In a circling motion, I moved my tongue around her, changing up my technique. With my fingers I opened her up, exposing her clit again. Like before, I began licking her clit like it was ice cream. As I went up and down Amelia let out soft moans. I heard her inhale deeply and let out a mean of pleasure. When I licked my jaw moved, pushing my tongue into her clit. I looked up to her with her eyes closed and with an O-expression on her face. She traced her hands down her stomach and ran her fingers through my hair.

“Keep it up like that, I’m close,” She cried. “Play with my tits some more-”

I quicken the pace of my tongue. Caressing her clit faster with my tongue. I followed her commands and played with her nipples. I reached up with my hands and grabbed her tits. When I rubbed her nipples she quietly let out cries. Amelia’s moans and cries became more audible as I went on. I felt confident eating her out, pushing me to keep on going. To the best I could, I went fast, trying to help Amelia reach the top. I played with her nipples some more, tugging and pulling on them. My tongue, over and over went over her lil bump. I could feel her little body shift around as I licked. She kept almost moving away from me but was able to keep herself in place. Amelias’s tensed body up, she pulled my face in. She let out a soft sigh. She let go of my face and I proudly lifted my face. I saw a pleased smile on her face.

“That felt amazing,” she said smiling. “I’m surprised you were able to do that!”

“Oh… thank you, I surprised myself” I bashfully said. “Hey Amelia.”

“Yeah?”

“Thank you for doing this.”

“Hehe, nah thank you,” she chuckled.” This was a good experience.”

“I’m glad it was. Thank you for helping me lose my virginity,” I shyly smiled.

“It was my pleasure, especially since I got something out of it. Besides you were someone I could trust to fuck.” Amelia looked at me very playfully.

Amelia got up from the bed and grabbed some tissues from her nightstand. She wiped off the cum from her chest and face. After she threw away the tissue, she came back and kissed me. We embraced each other in a kiss for a minute. Before we got cleaned up, we took care of ourselves in the bathroom and then went back to the bedroom. The next half hour we laid underneath the covers over bed naked, talking. We talked and laughed about the different things going on in our lives. I felt very relaxed and comfortable in that moment. Soon we fell asleep in her bed and slept the rest of the night away.

In the morning we awoke, got dressed and ate breakfast. Amelia led me to her door and thanked me for the night. I thanked her for the once in a lifetime experience. We hugged and said our goodbyes.

The following days were a little awkward. There were some stiff moments between us at school but we acted normally and continued to talk. We were able to go back to being good friends again. Though I feel there was some lingering tension but that might have just been my imagination, idk. I had a wonderful time with her and don’t regret anything. It was a one time experience I’ll look back on. Haha yes one time… or maybe?

Haha no it was one time

Unless…

Nah it was one time.

Source: reddit.com/r/gonewildstories/comments/kv8f8k/mf_i_got_to_fucked_my_best_friend_and_lose_my