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I’ve been reading stories for about five years, but I’ve been very hesitant to start posting my own stories for various reasons. This is my first story, and, as I mention in my profile, I welcome all criticism, I’m very curious to learn what specifically I need to improve when I write more stories. I wanted to write something simple to get my feet wet on here, and didn’t want to start with something I had planned for a little more. As I allude to in my profile, this will be one of multiple stories where some of the dialogue in it actually happened, but all the characters’ names and the setting, among other things have been changed.


I’ve always been the shy, introverted type. I have always been well-below average height for a boy at every age I’ve been. These two factors have meant I’d never had much confidence with talking to girls before I started high school. I had my first kiss in the Summer before my freshman year of high school (which I will talk about in another story), but that had been the extent of my experience.

I grew up in one of the more diverse neighborhoods in Chicago, and the elementary, middle, and high school I went to had a lot of cute girls from all races. I just had never had the brain wiring to talk to them.

I had poorly squandered what few opportunities I had to that point. Here’s one example from my freshman year of high school- This isn’t relevant to the rest of the story but it shows how the way I am has caused me to be, not great in social situations.

There was a girl, named Katrina who was also a freshman that I had had class with where one day, at lunch, somewhat out-of-the-blue, a friend who was sitting next to this girl asked me if I would have sex with her, and I said yes. Later that day, I was leaving class and she had class in the same room right after mine, and I heard her say to a friend, “Kris said he would have sex with me.”

Now, in reality, I’m sure only myself, as I was leaving, and her friend only heard her say it, but to my ears, it sounded loud enough for half the room, including the teacher, to hear it. Instead of pursuing anything with this girl, I was just somewhat mad at her, for saying that about me that loudly. Fastforward to present, and this girl is a legitimate model, so yeah that was a missed opportunity.

Fastforward to senior year of high school, and I hadn’t changed much. Most students in my graduating class knew me, and I was cool with them, but I was still pretty shy, and there was certainly no student who I had gotten to know, intimately. I turned 18 in February of my senior year, I was still short for my age and most people who didn’t know me probably thought I was a freshman, and it was becoming evident that I wasn’t going to lose my virginity until I got to college.

The Government class I was in in my senior year had a few students I had never had class with. It was mostly Seniors, but included some juniors, as well as a couple super-seniors, which was what they called students who were 19 or older, who were still trying to get enough credits to graduate. In my high school, there were 25-year-old seniors and 18-year-old freshman, they just kept coming into school but not graduating.

One of these older girls in this class was named Brynn. Brynn was Hispanic, had light skin, black curly hair. She wasn’t the girl in this class I was most attracted to, but she did have very, very large breasts.

(Hang on, hang on. OK.. Now, I know what you’re thinking, ‘Here’s a first-time author making a rookie mistake just putting in large breasts on their character gratuitously’.)

…However, Brynn is based on a combination of couple of different girls from my high school, but one of them that she’s based on did have the largest breasts I had ever seen, or have seen since. Maybe that’s not completely accurate, but adjusted to her age, it is. I remember one day early in the school year, Brynn was absent and the teacher was reading the attendance, a kid I sat near said,

“Who’s Brynn?”

And another kid quickly replied, “titties.”

They didn’t have the exact shape you first picture when you think ‘big boobs.’ They appeared large because they sort of sagged, but not in an old person way, in a sexy and natural way. I’m no expert on cup sizes, so I’m not even going to try to guess what hers was. Hers weren’t wide, but were longer than half her torso.

Our teacher was absent one day a few months into the semester. We didn’t have anything to work on, and since I wasn’t that cool with too many kids in the class, I just listened to my iPod. During that period, I was sitting near Brynn, and a couple other kids, there was a moment where I could sense a couple of the kids glanced over to me. I could make out a few words they were saying, and Bahçelievler escort a guy, who was another super-senior, named Tom and had been cool with me, said to Brynn.

“Would you fuck him?”

“Yeah.” Brynn answered.

Of course, I didn’t let on that I heard that part of the conversation. Coming home from school, I had a few different routes to get home. Sometimes I’d be on the same bus as Brynn, and she’d get off a few stops before me. Beyond what we were working on in class, we didn’t really talk too often. I still felt that mentally, I wasn’t quite prepared to start dating or having sex. I had been masturbating since halfway through freshmen year, being around kids, both girls and guys my age who would talk about that kinda stuff a lot was a big influence there.

There was a winter storm one day in the second semester of my senior year, but not one where it snowed badly enough to close schools. It was one of those sleeting/freezing rain storms where it badly delayed roads. It took me two hours to get to school that day when it usually took between 30-45 minutes. I missed my first class of the day, which was at 8:30, and I had Government right after it at 9:25, and showed up about 15 minutes late.

Another student in the class and I got in the room at the same time. The teacher was understanding, but a couple kids in the class jokingly got on me, even though I tried making as little as an entrance as possible. I had been walking fast, and done a lot of walking trying to eventually get to school in over the previous two hours. I sat down out of breath, and a kid in my section of the room kindly said,

“You good?”

“Yeah. But getting here sucked.” I replied

A couple seconds later, I had finally had the unwanted attention off me. But then Brynn asked me, “Where do you live, cause I sometimes see you on the


“Like near Hyde Park, but I went a different route today.”

“Yeah same. One day you should get off the same stop as me.”


Even though there were a few other seniors I knew in Government class, I didn’t know too many besided Nico, a kid I had at least one class with every year. We’d talk about video games and girls and whatever else. One day, the students that Brynn would usually sit with weren’t in class, and she was sitting in front of Nico and me. The class would get somewhat loud when the teacher wasn’t teaching and had us working on the problems we were assigned.

At at one point Brynn started talking to us, I forget how it gets to this point, but eventually, she showed us a picture of herself, in a green bra and panties, and said,

“Do you guys think I look good?”

Yeah, I thought she looked really good. And yes, I was really, really looking forward to getting home and thinking about that picture again. Coincidentally, in this same week, the kid I sat next to in another class, randomly showed me a picture of a girl on his phone, wearing even less clothing, bragging that, “This bitch gave me head yesterday.”

At this point, I had never had sex, and according to his stories, Nico had some experience, but I remember he and I had an equal reaction to Brynn showing us this picture. I don’t know if between the two of us, we said more than one word combined.

Most people know that their high school and college experiences won’t be how it is in movies, and that was true for me, and I knew that in my first week of each respectively. However, with hundreds of female students in this school, there were some that were, as they say “easy.” Many students knew the exact staircase to go to where one could go with a student of the opposite sex.

So, I didn’t know if that was true about Brynn or not, and I couldn’t tell how serious she was, at the time, but she did say,

“If you think I look good, do you ever want to come to my house? I’ll light some candles, play some R&B, and we’ll have a good time.”

Nico and I exchanged puzzled looks. We both had that same “who us” look. That this attractive girl just propositioned us. We weren’t sure if the offer was for both of us or not, but I could tell that Nico had no intention of taking her up on it.


I didn’t talk to Brynn much for the next couple of months, in April, it had been a while since I had seen Brynn on the R2 bus, as I was still taking a few different routes home. One day I did see her, and she sat near me. We didn’t talk for 20 minutes, but when she pressed the button for the next stop. I got up and as quietly whispered, “is the offer still open?”

And in the same voice I heard when Tom asked her if she’d fuck me, said, “yeah.”

I followed her off the bus. It was a short walk from the bus stop to her house. Neither of us said anything. My Bahçelievler escort bayan mind was racing. I assumed everyone’s mind races before they lose their virginity. Brynn lived in the top apartment of a three-apartment building, similar to where I lived, 20 or so blocks away.

Brynn was wearing a teal shirt and jeans. Brynn frequently wore shirts that provided aesthetically pleasing views for others to others of her assets.

Brynn led me into her apartment, no one else was home, and she led me into her room. She closed the door, and kissed me. I had only kissed one other girl before her, and this was obviously different because it was leading to something more.

Just as promised a few months ago, Brynn lit a couple candles in her room, and sat me down on her bed. She had turquoise sheets that sort of matched her shirt. Then she took said shirt off, and I took mine off as well. We kissed again, then she unhooked and removed her bra.

I had seen plenty of comedic movies that made me paranoid that I was gonna ejaculate right then, and would have this fear a few times in the hour that followed. My cock was harder than it had ever felt, and was still only about half the length as one of her breasts. She took my hands in hers and I began feeling them. Then she guided my head, and I began sucking on them. At this point, I didn’t even care about the intercourse part. I just wanted to spend the afternoon worshipping Brynn’s chest.

Brynn made very little noise as I moved back and forth between breasts and her nipples.

The situation being what it was, I paused several times. Brynn could tell I was nervous, and at one point she said, “Is this your, first time?”

“Yes. I’m sure I make it pretty obvious.”

“I had a feeling, but don’t be nervous. You’re cute. You’re doing fine.” She replied.

Knowing I was without, I then admitted, “I don’t have any… protection on me.”

“It’s OK. I keep some.” Brynn got up and brought a condom over. I didn’t care at that point how many other boys she had brought to her home and had sex with before me. I was just thrilled for myself that this was happening, and that was all that was important at the time.

Brynn then took off her jeans, and sat back on her bed with just her underwear. Her butt wasn’t as big in relation as her breasts were to other girls, but that was more than okay. I’ve always been more of a boobs than butt guy, but to be completely honest, it’s face/eyes that carry the most amount of weight for me. If I think back to the five girls I’ve had the biggest crush on in my life, none of them I was attracted to for their physical features.

Brynn then got on her knees and presented her pussy, motioning that I should remove her panties, which had a bit of a damp spot over the crotch area. Knowing that I made her a little wet sucking on her breasts helped alleviate the anxiety I had.

I off he panties quickly, and removed my own boxers and tossed them both on the floor.

Brynn laid down on her back, and lifted her pelvis up. I knew that I was about to go down on Brynn, and I knew it was gonna be more difficult than sucking her breasts. Even though I hadn’t had sex, I knew that going down on a female was important. I think I first learned that in the scene before THE scene in “Pulp Fiction.”

I had seen plenty of porn to this point, but not nearly enough to know what I was doing here. I was more than a little over eager. I didn’t know about the parts of the vagina or the right amount of buildup when eating pussy. I didn’t know about inner and outer layers at the time, so I just stuck my tongue into her vaginal opening.

I didn’t know what to expect. I didn’t know what pussy what taste like, or feel like as I was eating hers. Brynn winced at first and my tongue slipped out, then we both relaxed, I took a second, and I put it back in.

I stuck my tongue back in and started licking her pussy up and down. I had no idea if I was doing it right or not, but Brynn started to omit quiet moans. I watched as her breasts drifted down as she was at a downward angle and that turned me on even more than I already was, and began licking her a little harder.

Brynn started giving me tips, knowing this was my first time, she shifted positions and told me that I should switch up my tongue movements. Brynn started breathing heavily and moaning a little more. Her moans were deep, almost manly, but that didn’t bother me at all. She sounded, and looked very sexy, and I was pretty surprised I hadn’t already came myself.

I began alternating between licking up and down and darting my tongue in and out of Brynn’s pussy. He moans, chants of ‘Uh,’ ‘Uhh, ‘UHH,’ were getting louder, and that caused me to begin eating her more Escort bahçelievler intensely and with more ferocity. Her inner walls were getting wetter and wetter and I remember not enjoying the taste at first, but loving everything else about this experience.

I maneuvered my arms so that I could feel her breasts again while finishing eating her pussy. Then Brynn came with one last loud moan, with her cream spilling out of her pussy. I sucked a little of it up myself and then the rest spilled on her sheets.

Brynn and I made out again. Then she started to lower her head to return the favor, but I stopped her. I was now so eager to the intercourse part, and already very close to cumming that I didn’t want her to go down on me. I just wanted to cum inside her. Brynn said “OK,” and slowly guided me on to my back.

“Is it OK, if I’m on top? Cause we can switch if you want to be on top your first time.” Brynn asked.

It was more than OK.

“No, stay where you are. I like this view.”

“I know you do.” Brynn replied, as she moved her pussy down my chest, letting a few droplets drip out of her pussy as she made her way down to my hard cock. I had heard all the jokes, but I knew here that I wasn’t going to last long, I’d masturbated enough times that I knew when I was close to cumming.

Brynn was taller, and bigger than me, so it took a few seconds to get used to her weight on me. Brynn unwrapped the condom, but it on my cock, then stretched out her legs, and slowly lowered her pussy onto it.

I remember thinking this was it. I was finally losing my virginity. I looked up at the ceiling and pumped my fist in accomplishment. Brynn saw that and smiled, before she put my cock in her began moving back and forth on it.

The first time she was all the way in, my eyes widened with the sensation. Brynn began moving back and forth and up and down on my cock, her moans weren’t as loud as when I was eating her pussy, but we both began breathing heavily.

Brynn increased her pace, as she was fucking me, I had the perfect view of her fantastic, other-worldy breasts. They didn’t bounce too much but they swayed a bit with her movement, as did her long, black, curly hair.

“You like this right?” Brynn said softly as she continued bobbing. “You like looking at me titties while I fuck you right?”

I just nodded.

“I know you do, and I love having them.” Brynn moaned the same way she had before- with concise “Uhh, Uhh, Uhh, UHHs.”

Then she slowed her pace way down, asked me if I’m close. I answered “yes,” as I was probably less than five pumps away from ejaculating into her.

Brynn suddenly lifted herself out of me, I wondered why for a moment, but she moved forward lowering herself onto her stomach. She knelt in front of me, then I knew what she was doing. She took her breasts and put my cock in between them. Her well-above average breasts engulfed my admittedly below average cock. With her breasts sandwiching my cock all it took was three bounces for me to shoot me load onto them.

Brynn sat up, with my cum dripping down her. I watched her, somewhat paralyzed from what just happened. Brynn took two fingers, swirled it around my cum that I just sprayed on her, then stuck her fingers in her vagina.

Even though it was my first time, and not hers, I felt some guilt that I had came and she hadn’t, though she came once after I ate her out, I think. I wasn’t sure. Though I could tell Brynn just wanted me to watch as she her got herself off one more time. Watching Brynn finger herself was as hot as anything else from this afternoon. In the few months where I had started watching porn, I loved solo as much as anything, and I started to feel somewhat hard again.

I stayed where I was, watching Brynn’s methodical fingering. I watched as I tried to study her movements in case I could learn something for the next time, whether it was with her or someone else.

Brynn started moaning louder than she was when I was eating her out. I sat next to her, and started caressing her breasts again, while she increased the pace of her fingering. Then I shifted to her side to get a better view, and watched as she laid down on her back, continuing to finger herself. Her moans of “Uh. Uhh. UHHH” grew louder as she climaxed. I watched her raise her pelvis up and watched cum shoot out of her pussy, which I wasn’t able to do.

Brynn and I both sat up, and made out again. I was exhausted and overwhelmed from the experience of my first time.

The next day, Brynn showed that she was clearly less gossipy than Katrina, as I don’t think she told anyone about our afternoon. I was glad, because I’ve never been one who wants that kind of attention.

I graduated in June, and I think Brynn did too. She and I didn’t talk much after that day. I saw her one day when I was home from college for the Winter when she saw me as I was about to get on the bus as she was walking past the stop. We didn’t talk much beyond a quick ‘hey, how are you.’ We didn’t keep in touch, but I’ll always be grateful, and will always remember her.

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