[M]y [f]irst tit-job from an unlikely classmate

I’m a long time lurker of anything gone wild, but after dedicating a good amount of time into this subreddit, I thought I’d give it a shot! I thoroughly enjoy all of the stories I read so far and I hope that I can give some others some enjoyment from my experiences too.

To give you some background before I start, this happened a couple years back during my senior year of highschool. I’d been in a boarding school for the duration of highschool and I’d gotten used to all the routines and regulations. I was a good student, always getting high honors and achieving places of leadership such as SA President and Resident Intern for the dorm. Things weren’t bad all things considered, but I was lacking in the girl department. I hadn’t really dated anyone during my time there, a little fooling around here, some over the pants rubbing there, but nothing too serious. I had already lost my virginity the day before I turned 18 (I was a little late sue me), but even that was pretty lack luster. The only couple of things getting me through senior year were fucking around with a girl who’s boyfriend I was friend’s with, and playing Destiny 2 with my friends (eyes up guardian). That was until I miraculously found myself sleeping with one of my classmates.

Before I start I guess I should to the whole obligatory physical rundown thing. I’m not tall, only around 5’7 (blame it on my Filipino genes) and I have long black hair I usually tie up in a bun. I go to the gym on the regular and I’m told that I’m pretty fit, so at least I got that going for me!
Ellen is the same age as me (both of us being 18 at the time). She’s 5’3 with a decent B cup and a pretty killer ass. She was a bit on the curvy side, but that didn’t matter to me. She had really short light brown hair and glasses that made her eyes look like two huge kaleidescopes constantly spinning.

We were in the same class, but that didn’t really mean much. Her and I surrounded ourselves with different people and never really ran into each other. That being said, I would always hear different stories about her floating around the school.

“I heard she blew Sam behind the maintenance shed.”

“As if! I heard she walks around with a butt plug and never takes it out.”

“What about for shitting?”

“…what about it?”

I always just kind of tossed those rumors aside though, there wasn’t really a reason for me to think about it.

The times I did end running into her, I always tended to focus on her ass. She knew exactly what she was doing strutting around school wearing those tight pants. I made it a point to gaze at her as she bounced from class to class. Seeing her pass in the halls everyday was a nice distraction. Apparently, she noticed my staring and decided to make a move.

This was a Friday night sometime before springbreak. We were allowed to hang out in the cafeteria (which was located right in between both dorms) until curfew. Ellen and I were in a pretty large game of UNO with a couple of other schoolmates. While the game was going on, we decided to make a contest of who could come up with the shittiest pick-up line. When it came to me, I simply said “Wanna spoon?” brandishing a plastic spoon I had gone up to get mid game and tossing it on the card pile. My line was met with a collective groan from the group with some “Fuck you”s coming from my friends and in the midst of it all, I made eye contact with Ellen who I saw actually laughing. The game ended short after and my friends decided to go to bed early while the others split up to socialize with other people. I was perfectly content to browse on my phone alone in the corner, but before I could even open it, I felt a tap on my shoulder. It was Ellen, she held up the spoon I threw on the card pile,

“Wanna spoon?” she said with a grin.

I took it from her and smiled, “I was just thinking I could use a good spoon. You thought it was funny?”

“I thought it was really dumb, but yeah. Funny too.”

The conversation itself after that wasn’t too interesting, we made small talk asking how our grades were, how the semester was going, my eyes occasionally drifting to her ass which was in a tight little black dress tonight, but finally the topic shifted (as most hormonal highschool conversations do) to relationships and sex.

“Have you ever used that on a girl before?

“Oh noooo way. I don’t think I’d ever find myself in a position to even say a pick up line to a girl, especially not that one. Besides, it’s not like it would work anyway.”

“You don’t think so?”

“No way man!”

“So if I ask for your snap right now, would that prove you wrong?” She said in an almost teasing voice, wiggling her ass a little in excitement as she leaned toward me.

It was at this moment that I realized that she was flirting with me, which caught me completely off guard, “I guess it would.” My words coming out in a sort of stammer.

She promptly handed me her phone and I quickly put in my information, handing it back to her after I finished. “We can talk about pick up lines, and girls, and anything you want now,” she stated with a victorious smile.

As I got up to leave, Ellen abruptly leaned forward and whispered, “Maybe I’ll even show you the ass you’ve been staring at all night.” Before I could even express my shock she was skipping to her dorm, giving me a quick wink before leaving the caf.

Over the next couple of days, we spent time a lot of time texting each other. She confessed her attraction towards me and I my interest in her. The conversations quickly started getting hornier and hornier, resulting in my first experience with sexting. Countless videos were sent back and forth of me popping my erect dick out of my shorts and her, spreading her pussy and squeezing her boobs. It wasn’t even a week of sexting and constant masturbation until we made plans to meet up.

I lived in the dean’s house which allowed me ample time to sneak out without anyone noticing (he was busy tending to his new girlfriend). We planned to meet in the basement of the girl’s dorm lobby where she had stolen a key which allowed us access to the guest room down there. My night off rolled around and I raced over to the girl’s dorm in the cover of night. I wore a tank top and some sweats as I figured these would be the easiest items of clothing to take off. I got to the basement door texted her to let me in. Just as I hit send my heart almost lept out of my chest as a group of girls walked past the hallway the door was on as they checked on their laundry. Ellen turned the corner just as they passed, dragging me inside, the both of us quickly running to the guest room which was also at the end of the hallway. We closed the door and not 5 seconds later, hear the footsteps and voices of the girls passing by once again. I tried to slow my racing heart and looked around the room, there was a bed in the middle and a couple of shitty mattresses stacked throughout the room. I quickly found myself staring at Ellen now.

She was in a white nightgown and obviously wasn’t wearing a bra. The dim moonlight from the window behind her made it so that I could see her perky nipples poking the fabric, resulting in my pants growing a bit tighter. There were no words to be said once we made eye contact. We both knew what we were there for…

Our bodies and lips met as we clashed in the middle of the room. These weren’t long passionate kisses, but a violent storm of saliva and sweat, any nerves that I had disappeared as our tongues intertwined, a little squeal emerging from her throat. Our making out moved from the center of the room as I pinned her to the wall, her left leg now wrapping around mine. I found my hands exploring her body, lifting the short nightgown and grabbing her ass with both of my hands and squeezing both asscheeks with all that I had, another squeal emerging from her throat. At that sound, I promptly stripped off my own shirt, hearing a small gasp from her as she gazed upon my toned body. I went back to work wasting no time on squeezing her ass and sloppily kissing her body. As my shirtless torso pressed up against her chest, I was acutely more aware of her breasts and the thin fabric separating me from them. I began to work my way down her body with my lips, kissing and biting her neck, successfully getting another moan out of her. I moved down from there, arriving at her cleavage, where I decided I would tease her just a bit. Sucking and kissing only the top and side parts of her boobs, only brushing her nipples occasionally with my nose or lips.

“Chris” she whined half out of breath, “You’re not being fair.”

I kissed her again, “How am I supposed to suck on your tits when you’ve got all these clothes in the way?” Before I could even finish the sentence, she had lifted her nightgown off her body and threw it to the side. “Now you have no excuse.” She said smugly.

I stood there for a moment, staring at the work of art in front of me. Ellen’s chest heaved with every breath, her tits slightly bouncing with every movement. I marveled over her nipples, perfect pink and erect, just waiting for me to suck on them. Before she could say anything else, I simultaneously picked her up by her ass and bit down on her breast, Ellen wrapped her legs around my waist and quickly covered her mouth, stifling a scream effectively destroying her smug facade. I squeezed and sucked in a rhythm, moving from breast to breast swirling her nipple with my tongue, gently biting her nipple, and pulling apart her asscheeks which succeeded in her stifling more moans of pleasure. A couple more minutes of this and she pulled my head back and managed to utter, “My turn,” a fire I can only describe as pure lust in her eyes.

She unwrapped her legs and led me to the bed prompting me to sit down where she made quick work of taking off my pants. She ran her tongue down the length of my cock through my boxers and much to my surprise, buried her face in my crotch and breathed in. She emerged and gave me a kind of a drunk smile, promptly shimmying my boxers off now, little Chris then springing up into action. She gasped again as she saw that I shaved (I heard about a dude who made out with a girl after he got head and finding his own pube stuck between her teeth. I didn’t want to take my chances, also you girls deserve to have a comfortable bj experience.) My dick isn’t anything to write home about, I haven’t measured it ever but I expect to be below average, whatever the case, she made quick work of getting it in her mouth. She was noisy and sloppy with sucking me off, her saliva thoroughly lubricating my cock. I whispered fuck and stroked her short brown hair with my hand. She popped my dick out of her mouth, “Are you close to cumming yet?”

“You’re going to have to do better than that to get me to cum.” I said, surprising myself a bit. The last time I had sex my stamina was pretty shit, but I now was pleasantly surprised with how well I was doing. Unfortunately I would be tested quite quickly on just how “good” my stamina was.

Without another word she took my dick in between her tits and began to stroke it up and down, her saliva allowing it to glide smoothly. She smiled teasingly at me and continued to stroke me with her breasts. I went from being a dominant force in the bedroom to using every fiber of my being to focus on not cumming all over her beautiful.. soft… perky tits……

wait no

My dick twitched with excitement, nearing the climax. Ellen, feeling it harden even more, began to stroke even faster.

No

She gave me another smile, “Come all over my tits. I want your warm cum all over me.”

No.

“Come on baby, just let it all ou-”

“NO!” I whisper screamed, forcefully pushing her back off my dick before I could climax. I sprung forward off the bed and picked her up, putting her in my spot, her legs hanging off the bed. “You don’t get to tell me when to cum,” I whisper into her ear, my hand covering her mouth. “You do what I say, not the other way around.” I pause to catch my breath, “and I say suck my fingers slut,” Ellen’s eyes lit up at the word slut. Truth be told I’m not really used to dirty talk, but this seemed to work for her so fuck it! I removed my hand from her mouth and inserted my fingers inside, which she greedily accepted, and focused on her tits again, licking, kissing, and biting her soft sweet body. I pulled my fingers out of her mouth and leaned down to whisper again, “If I hear as much as a peep from you, I won’t let you cum. Is that understood?” She nodded enthusiastically, the same lustful fire in her eyes as before, a serious look on her face.

I moved down her body once more, sucking her tits for a bit, but quickly moving on and down to her stomach, then to her naval, and finally just above her pussy where I was greeted by her peach colored thong. I kneeled down in between her legs, tracing her inner thigh with my fingers and ever so slightly breathing on her thong stimulating her just enough so she could feel it. I noticed the fabric get considerably more wet as I hovered over her pussy. I looked up at her and saw that her chest was heaving, her hand over her mouth, the lust in her eyes replaced with intense pleading. She wanted nothing more than for me to touch her there. She raised her hips up in an attempt for her pussy to meet my face. I backed up a bit to prevent contact, instead using my hands to pull the waistline of the thong towards me. She lowered her hips again and I continued to trace up and down her thighs with my fingers, now taking the thong with my teeth and pulling it down to her knees, I could feel her writhe a bit with excitement. I removed it completely from her legs and looked at her pussy, noticing the small landing strip of hair, and watching it twitch and glisten with her fluid. I decided to finally indulge her as I began to stroke her clit with my tongue, one hand going up to play with her boobs, the other hand which fingers she sucked earlier, tracing her lips resulting in more quivering from her. I slowly began to ramp up the speed, tonguing her clit with more purpose, squeezing her perky tits with more ferocity until I was going all in on her. My fingers moved nonstop deep within her as I flicked my tongue rapidly on her clit. Her muffled whimpers were getting louder and louder until finally I felt her body tense up as she began to writhe around even more until suddenly she arched her back and let out a primal moan. I made sure to go even faster now, seeing her through her full orgasm. I removed my fingers from her pussy and moved on the bed to lay next to her, my dick poking her leg. We lay there for a moment, both of us gasping, Ellen still hot off the waves of her climax twitched a bit as she whispered to me, “No one’s ever used their tongue on me like that before.”

“It sounded like you enjoyed it,” I say between breaths, “I’m pretty sure you woke up the whole dorm with that moan.”

“Well then they better get ready for more, cause we’re not done yet.”

She moved off the bed and placed one of the shitty mattresses on the floor next to it, lying down on it with her legs spread, “I need you inside me right now Chris.” She later told me she used that mattress instead of the regular bed because she was afraid the squeaking of the springs would bring attention, as if she hadn’t already done enough with that moan from earlier, but I digress.

I scrambled to my pants pocket and quickly put on the condom I brought, eager to get inside her hole. She lay with her legs spread open still waiting for me. This time I didn’t tease or take my time, I aimed and went straight in, closing my eyes enjoying how warm and tight it was. Ellen stifled another moan as I began to move. I started slow at first, going the full length of my dick in, and pulling out til just the tip was in, but it was obvious Ellen wanted more as she rocked her hips to meet my dick with every stroke. I changed the pace, giving her what she wanted, rapidly thrusting in and out in and out as I deeply kissed her, one hand supporting the back of her head, the other squeezing her nipples. I felt her clawing at my back holding on for dear life as I continued to slam my cock into her pussy. She pulled her lips away from me, moaning into my ear, “I’m gonna cum!!” I pulled my body back so that it wasn’t over her anymore, putting my hands on her waist and focusing everything getting Ellen to cum. For a minute we were pure euphoria; just pure pleasure and ecstasy as I continuously rammed my cock into her eager pussy. The feeling of her tight cunt wrapped around me and the sound of her moaning and her pussy squelching brought me to the edge. She gave out another moan, echoing through the room and I grunted, giving a couple moans of my own as we both climaxed. I pulled out and lay at her side, not even having the energy to take off the condom. We lay there panting for a couple minutes until Ellen turned toward me, wrapping my left arm in her arms, squeezing it between her boobs, “Hey,” she whispered with a smile, “wanna spoon?”

I chuckled and kissed her deeply, my tongue exploring her mouth, finding her tongue ready to accept me as I moved on top of her, straddling her now, my dick resting on her stomach. Without a warning, Ellen peeled the condom off and emptied its contents into her mouth like some fucked up kinda gogurt. “Can’t let anything go to waste.” I moved back beside her and actually invited her to spoon, with her being the little spoon. We lay there for a few minutes, Ellen every so often grinding her ass on my cock while I stroked her pussy and tits absent mindedly. After what felt like ages, we got up. I hugged her before I got reclothed. When I tried to pull away she pulled me in tighter, her tits fully pushed up into my chest, “I wish we could stay like this forever.”

“Ha. Me too.”

She let go and gave me a peck on the cheek. We put on our clothes again and left. I ran back to the house with an actual skip in my step. I had the time of my life. Who knew it’d be with her?

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I hope y’all enjoyed this. Feel free to give feedback and ask questions. I do have more stories I’d love to tell but we’ll see if anyone likes this first. Im always looking to improve. Lots of love to you all.

Source: reddit.com/r/gonewildstories/comments/eihpfc/my_first_titjob_from_an_unlikely_classmate