Thank you all of the support from my last post, and particularly to all who were kind enough to ‘tip’ me with some wonderful images. :)
I figured this time I could tell you about the night a classmate and I got to ‘refine’ how well we could pleasure each other. To skip the background..which is again long, just scroll down to —. The names have obviously been changed. Also, no need to ask for photos, I am not one to share their stuff besides what I am already sharing.
When I was a senior in high school, [after not getting the job at the restaurant](https://www.reddit.com/r/gonewildstories/comments/lij0h0/manager_did_not_hire_me_so_i_20_m_defiled_his/), I started working at a bakery. That meant I had to start my shifts at 6 am on Saturdays (woof). Naturally, I was awful at waking up early and soon found out that it was easier for me if I just stayed up all night and then went to work and took a nap after my shift. So on Fridays, I would either attend parties or host gatherings at my house, particularly when my parents were out of town for conferences and this particular weekend happened to be one of those.
Spring break had just begun and the only ones from our friend group not going anywhere were my friend Mike and I. Now, let me just express the bro love I have for Mike. This guy is the most laid back friend I have who has always been up for anything or nothing. Meaning, If I proposed a road trip to Chicago he would be down, but if we stayed back and played Halo all night he would have no quarrel.
This particular evening was looking like a Halo night, but having to work during spring break very much left me wanting to have some fun. I started to text whomever I could think of that I knew would still be in town with no luck. Soon I moved to Facebook and remembered I had a new friend on there. Her name is Kelly and she had just transferred into our school from England. Now, Kelly was a piece of work, she was this beautiful and athletic brunette with a great butt, nice C cup boobs, beautiful smile standing short at about 5’2. Given that all foreigners tend to band together I had the chance to get to know her early on and flirt a couple of times. I messaged her asking if she wanted to come over and hang out with a friend of mine to drink and play some games. You have to shoot your shot, right?
About ten minutes later I get a response. She already had plans and was hanging out with Mairin, but if we were down they would both be down to hang out. PERFECT. Now, Mairin I wasn’t too familiar with. She never came out to the same parties as us (if any at all), she was always the straight a student at school and as you can assume, her and I weren’t a likely match. She had a very pale complexion, bright red curly hair, smaller boobs than Kelly, but a larger butt that occasionally left me admiring.
This was high school in the late 00’s and they dressed as such in their Abercrombie & Fitch/Hollister jeans and mini skirts with the tight shirts with the moose and the seagull respectively. Quite attractive at the time.
As we started to make quick work of our 30 pack, it became quite obvious that Mike and I were both interested in Kelly (there is just something about a British accent). Now, Mike and I have always been competitive, but also not ones to call ‘dibs’, after all the decision lies ultimately with the girl. And it was clear she was more interested in him, which as bad as it sounds it left me with Mairin. Again, not that anything was wrong with her, but historically she was a goody girl who had also realized that neither of us were there to make a move on her.
Fast forward a couple of drinks and now Mike and Kelly are full on making out, while I am trying o be a good host so that Mairin won’t want to leave until my friend and Kelly settle their business. Soon, they move things to the guest bedroom and after a while Kelly comes down asking Mairin if she would be willing to spend the night here. By that point things between Mairin and I had warmed up a little and she reluctantly agreed, but made sure to tell me not to get my hopes up, which in truth I hadn’t.
I walked her up to my room and told her we could share my bed while they took the guest room. Now, what is the point of working 20 hrs/week if you don’t do nice things for yourself? I had purchased a king size bed, which was my pride and joy at the time. Deeming the sleeping arrangements acceptable we turned in for the night at around 11pm.
__
Hearing the moans coming from the other side of the wall ere leaving me quite hard and at this point there wasn’t any chance I wasn’t going to try and make Hail Mary move, but I am not one to push myself onto someone, and so I came up with the lamest and oldest pickup attempt.
*Me: Hey, I am cold. Are you?*
*(Heart starts to pound)*
*Mairin: Yeah, a little.*
*Me: Do you want to cuddle?*
*Marin: Yeah, sure.*
In my head, I felt like motherfuckingHitch with the smooth lines. Truth is she probably was horny from the sounds as well and anything would have worked…but just let me have this one, okay?
I turn myself to my right as she starts to make back her way into my arms and at this point I am not here to hide how erect I am. I feel her wonderful ass press against my dick and instead of moving away she kind of just pushes back and arches her head a little. In my mind, I am like fuck yeah. We are on buddy.
I start to gently breathe on her neck and nip softly at her earlobes eventually fully on putting them in my mouth until she just whispers “Fuck…” and turns around and starts making out with me while our hands try and touch everything that is front of us. Now, I am not one to have fool around with the lights off because I love gazing a the beauty in front of me, but getting to explore someone else body in complete darkness while making out was definitely something to be had.
Anyway, we are making out and at this point I have grabbed her my the hips and flipped her on top of me and am taking her shirt off while she is unbuckling my pants. Soon we are down to just our underwear while making out, and somehow the moaning next door had not drowned out which is only fueling what is going on in my room.
I managed to take her bra off and am making sure I touch and grab very bit I can while I glue my mouth to her right boob and start playing with her erect nipple with my tongue. Again, we are still in darkness and the only way for her and I to see is through touch, which in the dark it felt enhanced.
As we are dry humping I feel a wet sot on my dick that is most definitely not from all the precum pouring out of me. She lowers her mouth to my ear and says “I need you inside”. Yes ma’m.
I slide my dick trough the opening on my boxers and move her thong over to the side as I slide in. My God. She was so tight it took quite a bit of time for her to lower herself entirely. Witch each inch feeling as her walls expanded to make room. Thank you, Budweiser, for giving me enough of a buzz to not finish with each new push. After a couple of seconds she starts moving her hips slowly and soon we start going at it. She sits up right and she places my hand on her left boob while I am pinching her nipple with my left hand. “Harder” she says, so I start to pound from underneath her, but she says no and lowers my hips back to the bed as she continues to ride me. “I meant pinch my nipple harder”. As you wish. At this point I am borderline giving her a nipple twister as I feel the walls of her pussy contracting and her legs twitching until she takes my hand off and slows down her hips.
Now you’ll remember from my last story, If I do not cum in the first pose chances are it will take a while. This is the night I found that out.
She gets off and we hear a knock. Apparently Mike and Kelly were done and wanted to see if we wanted to go down for a drink. I lent her some sweats and shirt while I wore something similar and went down for a drink.
We joked, around, shared some stories. And then Kelly lets a bomb drop. “Mairin, I didn’t think you’d be popping your cherry tonight” Uhm. What? Mairin denies it and Kelly calls her a liar, but at this point it didn’t matter. We finish our drinks and head back upstairs.
As soon we are up in my room, Mairin pushes me to the bed and we start making out again. I pull her off and we chatted for a little bit. Turns out it WAS her first time, and she was embarrassed because she didn’t want to be the prude her everyone thought she was (had me fooled).
Conversation continues and I tell her I really had only had sex a handful of times and only gotten a blowjob once. To skip the jargon I come to find out that she watched quite a bit of porn and has always wanted to try so much of what she sees and we kind of decide to experiment on each other and learn what feels good and doesn’t. After all I still had about 5 hours to kill before I hard to work.
She starts by giving me head, which in reality was okay. But as she kept going I told her what felt really good and what didn’t. Soon she wasn’t using her teeth at all, was trying to take me as deep into her mouth as he could while lightly stroking my dick in perfect rhythm until I almost came. We then switched and it was my turn. I had only eaten someone out once before and I didn’t care for it, but for some reason everything about this experience was enhanced. Probably the pure lust in the air just flipped a switch. She told me where to lick, where to suck and when to start working my fingers in and in what motion and I was really getting into it. She smelled delicious and tasted even better and the way she was pushing my face into her as she moaned her approval gave me all the determination I needed…until she said “put your finger in my ass”. That was a wrench and I looked up and she hastily told me that is what she often saw and always wanted to feel…so what the hell. I started vigorously eating her pussy while working the nerve and soon I started to play around her asshole before beginning to insert my index finger. As I did her moans because almost screams, which only turned me on more and encourage me to go knuckle deep and began to thrust in and out. Her thighs had me in such a clamp I stopped hearing her moaning and soon her legs began to shake as she pushed her hips up and my face deeper… I thought I would suffocate, until she relaxed her grip
Side note: I love pale girls. Nothing like seeing their entire midsection turn blotchy red after intense orgasms.
I scooted up next to her face while lightly rubbing her pussy until she grabbed my hand and sucked off each one of my fingers. That was fucking hot and I was ready for more. If I didn’t finish tonight my balls would burst.
She gets on all fours and asks of I am ready. Oh man, this was the first time I truly appreciated what I saw from behind. I kept thinking back to the fact that my finger had been in her ass and how it had made her cum. Fuck it I thought and I began to lick around her ass as she started to squirm barely managing an “Oh my God” as I steadied her hips and this time began to lick her from her pussy to her ass. Not gonna lie, not as disgusting as I always thought it would be. I actually liked it, but I needed to get my own. Lined up behind her pussy and with a little guidance from her (still fairly inexperience at this point haha) I pushed in and it was so warm and wet it felt amazing. I started to pound with all I could trying to finish. As I started getting closer I asked her where she wanted me to cum and she told me she wanted me in her mouth. I told her I was ready and as soon as her mouth wrapped around my dick I began to cum until my scrotum hurt. The whole situation was amazing.
After a while we fooled around more, trying different ways to finger her, I got my butt licked (not my thing), and even tried anal, but we failed this time. We became great FWB until eventually she got a boyfriend and I got dropped. I wasn’t exactly relationship material and we were both mutually benefiting from each other to see what we could try. We kept contact through the years and occasionally get to enjoy time together.
By the time I got into work my neck looked like it had been attacked by a family of leeches to the point where my manager came to pop my collar and stapled it together telling me to never come in like that again. Whoops.
Mike and Kelly ended up dating for a while, but she turned out to be a cheater.
Just like last time, if any of you ladies wish to ‘tip’ me with stories or extras, it is all very much welcome :)
Sorry for the long story, but once memories started to pour in I wanted to write it all to better preserve it for myself.
Lastly, Mairin is aware of this post mentioned that if she feels like responding to it and adding to it she is more than welcome.
Source: reddit.com/r/gonewildstories/comments/lnp2pp/much_of_what_i_18_m_learned_i_owe_to_an_18_yr