[MF] Stretching the boundaries

Little bit of background: I graduated high school in ‘09 at 6’6″ and 150 lbs. I was a razorblade and very consciout of it but no matter what I fucking ate I couldn’t gain a damn pound.
Wish that was the case now! Fast forward to the time of this story when weighed in at a more solid 210 lbs and was in some healthy shape because of my job. I lifted heavy packages and consistently walked over 18k steps every single day, even hitting 24.5k in a 5 hour period once. I was feeling better about my body than ever before and had a lot of stamina. I’d like to think of myself as a decent 7/10 on the looks scale as I was lucky to have dated pretty gorgeous girls but I was never one of those popular guys in high school that had ladies hanging off his arm.

I had gotten pretty intimate with a few of my gfs over the years, rounding all the bases several times but never able to cross home plate thanks to where I live (Check state initials in my username). I got to be pretty damn good with my long-ass fingers thanks to one girlfriend in particular, which will come in handy later. This experience experience happened a couple years ago, but I will never forget it.

Alright, let me introduce you to Brit. Brit is a bombshell of a 5’1″ 95 lb 18 year old that was in my first class (fall semester) at the university I just transferred too after a few years at one by where my house is. I’m 24 when I meet her. It was my first semester there and her first one ever. This was the first class of the day for both of us, then we basically followed each other to our next class. I hadn’t had any serious thoughts at all up until one day following her on a day she was wearing a shorter shirt and leggings and I realized she had the most perfect ass I had ever seen in leggings. It was small and tight, not jiggling a bit as she walked but you could tell it wasn’t one of those bony asses. She had a little meat, but narrow hips. She was super shy and never spoke up in class and hardly talked in the group projects, so even though I have never had trouble talking to women or striking up conversation with someone new, I just needed to find my ‘in.’ We would just walk to the our next class on the other side of campus every other day and never say a word. Finally after about 2 weeks of this shit I just go for it. Right after class ended, I catch up to her. “Hey, I saw you walk to such and such building clear on the other side of campus after this class, right?” “Yeah, you walk that way too, right?” La-de-da, we become friends because talking for the 8 minute walk is way more fun than staring at concrete.

A week later, she starts sitting by me in class because I’m the one and only friend she has made on campus. It comes up one day she needs some help with calculus, and I had just finished Calc 3 at the previous university I studied at, and offered to help. She quickly accepted the offer, to my surprise, and arranged a time we could meet in a computer lab and go over her homework. We meet at a lab and dead honestly worked on her homework with the purest of intentions. 2 weeks in, she wears a flannel shirt instead of the massive jacket she usually wore that was fitting her pretty loosely. To this day I don’t think she meant to do this at all, but she bent over to pick up her calculator that fell right as I did the same and though I really did try to look away, I saw the beginnings of firmest double-D’s I had ever seen through the top of that flannel shirt. I quickly look away, embarrassed, and with the angle she was at it was impossible she saw me. I kept tutoring her for the rest of the semester and no more fun little ‘incidents.’ Spring semester I didn’t really see her because we both had wicked school schedules and she didn’t seem to need much help with math anyway, so we kind of fell out of touch.

About this time, right before school picks back up in the fall, I get a text on my phone. “Hey, I’m taking PDEs this semester and you said you’ve taken that class before, can I have you tutor me again? I’ll make it up to you, there’s a burger place down the street and I’ll buy you lunch once every week or two.” I was excited, and I love that burger place. I wasn’t about to let a girl/woman pay for my lunch though, don’t worry. Never one to turn down helping a friend out, I replied with, “Sure, I’d love to help!” She mentions when school starts next week, we should meet for lunch in the food court on campus and catch up. I agreed, since it had been a while and I’d like to see and catch up with her. We both had a 3 hour break between classes right around lunch time twice a week, and we seriously talked for the entire 3 hours that first day like we were old friends.

It turns out she kinda sorta dated somebody over the summer and had sex for the first time just a week before she texted me (I can’t remember how that came up, sorry). I just remember I couldn’t believe what I was hearing. When I said she was a bombshell earlier, I meant it. She was really cute and had the most stunning body I have ever seen with clothing on. There is _no_ way this girl lost her virginity at 19 years old. Some asshole somewhere had to have made some fake promises and taken what he wanted long before then, but no. I asked how it went. She thought it was horrible and couldn’t believe that people were so into it. I sat there stunned. This girl had lost her virginity to somebody who very much did not know how to please a woman. At all. I had to ask, right? “Why did it suck so bad??” She said, “Well, I hardly felt a thing and it was over in about a minute.” I felt my jaw drop. I had so many questions. I asked how his foreplay was and if he got her properly warmed up and ready for it and she look at me like I was crazy. Turns out they just made out, clothes came off, and he stuck it in a good 10 times and came on her stomach.

I couldn’t believe what I heard. At this point, we decided we were going to have an adult conversation about sex so we moved to a little more private spot in the food court where people weren’t walking by us constantly and she asked me why I seemed so shocked when she said she didn’t like it. Now, I remember the topics discussed just fine, like ‘There has to be foreplay or it’s just selfish on the dude’s part’ and ‘I can’t believe he only lasted that long’ but the only words I can specifically remember saying were, “Brit, you need to find you a man that actually knows how to please a woman.” She just stared at me after I said that.

She wants to hang out again in two days when we have that break again, except this time she wants to go to the burger place. We meet up and go to the burger place, but instead of sitting and talking like we did before she eats quick and tells me we need to hurry and get back, so I hurry and eat too. Of course I paid for the meal and then we left. When we get back (She drove. She lives around there, I ride the bus) and she tells me to stay in the truck as we pull into the parking garage because she has lots of questions. I oblige, since we’re friends and I want to make sure the next time this girl blesses some guy with that phenomenal fucking body of hers, she makes him earn it.

Ashe asks all kinds of questions like what have I done, what have I had done to me, etc. Britt texts more questions for the next few days, then we’re in her truck chatting again in the parking garage after the burger place. Friendly chat, but when I look at her I see her staring at me, wheels turning in her head. One thing leads to another, and she’s got me in the back seat of her truck, making out with me. I hadn’t felt that kind of passion before. There was a deep want, and I could tell. She backed off after a few minutes, apologizing for rushing or something. I tell her it’s fine and I probably enjoyed it much more than she did. We both realize we’d been there for a while and needed to get to our next class anyway.

That night she texted me asking how I felt about what happened. With everything that had been going on, I replied with “I don’t regret a thing. Sorry if I crossed a line with you, though. I don’t want to make you feel uncomfortable.” She simply said, “You didn’t get anywhere near crossing a line.” Well shit, if that isn’t a challenge I don’t know what is.

We’re hanging out in her truck yet again in the backseat already just talking, because I ran away from her poking me or something but also seeing where things go and of course, she followed. I confront her about this line of hers and where it is, and she lifts her shirt off. There are those perky tits again, but this time only her white bra covers the best parts. I can’t help but notice that the bra is only there so her perky tits don’t poke through whatever top she is wearing. Basically, those things don’t need any help staying up and in place and they’re -huge_. I realized their firmness when 10 seconds later the bra came off. Greatest tits I have ever seen with the most perfect mid-size areolas with nipples hard enough to cut class with and were slightly pointed up. I took a breath, realizing I had been holding it the entire time. She asked if I was just going to keep staring at them or if I was going to get busy. I immediately pull her in to kiss her, holding her in my left arm while learning every inch of those perfect tits with my right hand. I have never felt any this firm _and_ big before in my life and trust me, I have handled dozens of pairs up to this point. In my experience, huge tits sag even just a little bit because of weight. These all-natural beauties didn’t sag a bit.

I feel something on my wrist, and realize it’s her hand. She guides my hand down her pants, which I just now realize is undone and unzipped. As soon as my fingers make their way to those blue panties, I can feel her heat. An inch later, I feel her panties are soaked. She wants it because while kissing, she bites my lip slightly. I do what I do best, and she breaks away from making out. I open my eyes and look at her, and she has a fucking adorable ‘Oh!’ face. It’s the hottest one I’ve ever seen up to this point in life. Eye’s shut super tight, and mouth as open as it can be. I go up and in, back down to the pussy but this time without panties in the way. She’s now screaming while I tease her clit. I take my hand out after a couple minutes and laid her down on the backseat of her truck. I reached under her perfect ass, which is even more perfect than I ever imagined was possible, and with her legs straight up I took off her pants and panties in one smooth-ass move.

When I moved them out of the way and set them down, I looked back a what I saw then will be a sight I will never un-see for the rest of my life. It was the most perfect pussy I have ever seen. I have seen my fair share of porn, and my favorite kind was always petite girls. I’ve seen what they call a ‘tight’ pussy in porn. They had nothing on this. This innie pussy looked like it could maybe fit a half-dollar coin. Barely. I felt a really dull but strong pain from my crotch. I realize I still have my pants on, but I have the most intense erection I have ever had in my life. While I started to finger her clit again, I slid my pants off. Coordinated, right? I have no idea how I did it and I’ll never figure it out. I hit autopilot with them and boom, they were off. Meanwhile, I go to slide a my pointer finger inside of this now soaking pussy to get a feel of what’s going on down there. Now, I have big hands. From thumb to pinky is 8.5 inches. My fingers aren’t very fat, and I can’t get my finger even started into her. I make my round around the labia and the clit again, to her delight, getting my finger wet. When it’s all wet and ready to go, I try and slide it in again.

I realize then why I couldn’t get my pointer finger in there in the first time. My finger being wet wasn’t the issue. Her pussy was literally just that tight. At that point I thought my dick was going to burst, it was so hard. I remember looking at it and thinking, “Holy shit, I’ve never had veins popping on it before! This girl is fucking _hot_!!” I eventually ease my finger in there slowly, and she throws her head back, moaning. I’m one knuckle deep. I make it to the second knuckle, and she’s moaning like she’s about to cum already. All I can think is, “Oh, this girl’s done for. This one’s going to be easy.” I get my finger in all the way, and make one small ‘come here’ movement with my pointer finger. I’m glad I took off my pants. She screamed something like, ‘I can’t stop it!’ and then I got drenched from her squirting right as I pulled my finger out after that one motion. Just like you see in porn; sprayed right on me. That was fucking hot, I thought that shit was all made-up. She came so hard from that one little move that her legs started shaking.

After a few seconds her legs calm down and she looks at me and says, “Now I want you in me” then looks down at my cock standing at full attention, her eyes growing wide when she does. I asked what she was surprised about, I thought she’d seen a cock before..? It was then that she showed me the length of the cock on the guy she had sex with over the summer. She held her pointer finger and thumb an inch and a half away from each other and said, “With a full boner, he was only this long and only this thick,” cutting that distance into about half. I laughed. No wonder I couldn’t get my finger in there. My finger was as big or bigger around as this dude’s dick was at full mast. Poor guy, but not my problem right now. This girl thought all must be small like that but there I am with one that she just barely can’t fit her fingers around and when I measured it in high school back when I think most guys did, I was 7.5″ from base to tip. Brit realized then that she fucked what I believe is referred to as a ‘micropenis’. Too late to stop now, she already said the magic words. “Now I want you in me” That’s consent, right? Cool, thought so. Just kidding, I checked with her again just to make sure! Always get consent, my friends.

I moved her so she sat in the middle of the back bench, feet up on the headrests with that pussy erect (yes fellas, they get small erection-like reactions too that open up the labia if you do your job right), pulsing, and glistening with her cum. She’s ready to fuck. I look at her, and there’s a look of worry on her face. She still looks in shock, staring at my cock while I maneuvered my way to the floor, legs under both front seats, facing her. I ask, “Do you still want to..?” “Yes.”

I tease the entrance of her pussy with my tip, and she breaks her stare-down with my member, her head flying back again and I have to catch it before she hits the back window this time. She chuckles for a second, imagining what’s going to happen, until I tease her clit with the tip of my cock. Smile’s gone. Biggest ‘Oh!’ face yet. I get the tip nice and wet because this is not going to go in easy. When I get covered in her juices, I set the tip in place. I hear her gasp, and I’m fighting my instincts to just shove my shaft into her. I have to play nice, because she needs to know this can be enjoyable and I’ll get to know her depths soon enough. Also, if I do this right, I might get another chance on a bed or couch later! I slid in slowly all the way and I can’t believe how tight this is on my cock!! I’ve been gripped tight during some good hand/blowjobs, but nothing felt like this. She was incredibly hot inside. I loved every millimeter as I slid into her… All the way until about halfway down my shaft. That would be the cervix, I’ve felt this with one other girl before before but definitely not only this far in. I look at her, and she’s holding her breath, wincing and biting her knuckle. Worried, I ask if she’s still ok. She says, “K,DON’T STOP, but it fucking hurts!! You’re stretching it in every way possible!” Grin pops up on my face. I knew I was decent sized, but when you hear those words, you feel like you have a foot long schlong about the width of a baseball bat all of a sudden, right fellas? Felt my cock swell a little more from that little quip…

I do the slow in and outs to lube up the inside of her so that I can get to work on her. Once she’s all wet inside, I start doing the real stretching. I slowly go in and out so she can adjust to my girth, and every 5th stroke or so I’m pushing juuuuust a little deeper. During the strokes in between, she would regain enough composure to look down at what was going on and say, “Fuuuuck, I love it in me…” Then on that 5th stroke she would throw her head back again as I pushed a little deeper yet again. Eventually, after a few glares from her for pushing a stretching her a bit too far once or twice, I was able to go almost all the way in. This, about 7-8 minutes in, is when I grabbed her hips and started thrusting faster and deeper.

Her face turned into one of ecstasy, and then I realized why. With the angle we were at I was pounding the shit out of her G-Spot. I got excited for a second, thinking what if she…? Too late. Immediately my cock, still being thrust in her, is soaked anew with her squirt. That was too much, I couldn’t hold it any longer. I asked her where she wanted me to cum but she looked at me with a blank stare, not knowing how to answer this new question in this new situation. I asked if it was safe inside because that’s my favorite place, she nodded, and I gave in (Stupid in retrospect since we were rawdogging it. Use a rubber, fellas). I would be lying to you if I told you that while I held my cock as deep as I could and erupted my load into her that it wasn’t coming out the sides around my shaft at the same time. I’ve never shot another load that huge, let alone in/on/or around a girl in my life. It’s the only time in my life I have seen my own cum run out of a girl while I was still balls deep and still cumming in her. I then leaned in and and we kissed for a little bit with my still throbbing cock in her pulsing pussy, dripping cum out onto the leather seat. I pulled away from her kiss and pulled out of her, my cum spilling out slowly as she retracted to smaller dimensions. She looked me dead in the eyes with a huge smile. “That felt amazing.”

I looked her dead in the eyes, and with a little smirk said, “I’m glad you enjoyed it! Just wait, though. Let me get you in a bed one of these days…” In my head I was thinking this was the perfect pussy to learn how to go down on (Spoilers: I love eating her out and I’m getting hella good at it!). She looked at me with her great big eyes, and I could see the wheels turning in her head trying to figure out what time and place would work for both our schedules and what the fuck I was going to do different next time if she could barely handle this time…

I get a text later that night. “That was AMAZING, but I can’t FUCKING WALK! >:( What are you going to do next time?!?” All I sent back was one of those silly wink faces ;) Needless to say, we met up again very soon after and she learned what I meant…

Source: reddit.com/r/gonewildstories/comments/bfwd55/mf_stretching_the_boundaries