This tale requires quite a lot of backstory so if you’re just here for the naughty bits and not a short novella this might not be the story for you. I’m writing this mostly for myself. This is a very vivid series of memories for me, so even though it was quite awhile ago, I remember mostly everything. I did my best to remember all the little details about these events. All names have been changed and for the purposes of this story my name is “Matt”
This story starts at the beginning of the summer of 2010, I was 20 and I had just completed my sophomore year of college and was going to take a year off to work and save up my money before going back for fall semester 2011 to finish up my degree (this is important context for later).
I hadn’t seen some of my high school friends for a bit (even though we played games online together), so we decided to set up a hike/picnic to a nearby waterfall. All is good, and my friend Jake asks if it’s okay if he brings someone along on the hike in our group chat.
We all tell him that’s fine, but we were all pretty curious about this person (suspected girl) since Jake is extremely socially awkward. After a bit of grilling we find out that it is a girl whom he met on plenty of fish (an ancient dating site of olde). In my mind I’m thinking that it might be pretty awkward for her, but as a friend group we’re usually pretty welcoming so I didn’t worry about it too much.
The day of the hike rolls around and we all are meeting at the start of the trail and are waiting for Jake to show up. After a bit of waiting, we see Jake’s car approaching, they park, get out and approach us. The first thing that I notice is that she is quite tall, even next to Jake who is 6’4″ (I find out later that she’s 5’9″). She had shoulder length blonde hair, pale complexion, very large tits, and was very overweight. She was wearing a tank top that showed off her cleavage and bounced mesmerizingly when she walked.
Despite the boobs though, she wasn’t really my type as I preferred fitter girls. Though I could easily see what my friend saw in her physically. He introduces her as Kate and we introduce ourselves back to her. It was this introduction, and looking back, that was probably one of the most pivotal points in altering the course of my life.
It’s a short hike, about 45 minutes one way and very quickly we started to chat about our respective college experiences, what classes we had taken and some of the cool experience that we had that year. Kate chimed in every now and them with a remark or an anecdote, and we learned something quickly about Kate: she was very funny. She was very quick-witted and very good at ribbing on people in a playful way.
Overall she left a pretty good impression on all of us. We found out that she had just graduated high school (she was 18), which was a bit weird for Jake to be seeing someone fresh out of High School. Regardless we had been hiking for about 30 minutes, and I could tell that Kate was having some trouble keeping up and was starting to lag behind, and Jake was too busy talking to one of our friends to notice. So I slowed my pace and started to walk alongside her and talk to her.
She was getting pretty short of breath and pretty clearly needed a break, So I called for a water break and she gave me a very grateful look and after she catches her breath she says “thanks Matt” I tell her no problem and she should drink some water. Jake was still talking to our other friend, so I decided to keep Kate company and talk to her a bit. I learned that she was planning on going to culinary school in the fall which was cool as I loved to cook, so we bonded a bit over our mutual love of cooking.
She also loved baking & pastry and had made lemon bars for the hike (they were delicious). For those curious I made spicy tuna rice balls. The rest of the hike is mostly uneventful and we eat our lunch in front of the waterfall, which is nice and cool, and then head back. Before we get in our cars and leave Kate adds us all on Facebook.
We see Kate and Jake a number of times over the next few months and towards the end of summer it becomes apparent that Kate is not really interested in Jake anymore and honestly I couldn’t blame her, Jake would occasionally remarks about her weight which I thought was extremely rude, and looking back I probably should have told Jake to fuck off with that shit, but I didn’t, which I regret. Fall comes and I get busy with my new job, and all my friends go back to their respective universities, and unsurprisingly Jake and Kate are no longer a thing. In the spring I meet someone and we have a bit of a fling (not really for this story) for a few months until it just kind of fizzles.
Before I know it summer rolls around again, Kate would tag me and other friends in funny memes on fb sometimes and that was the extent of my contact with her over that year. She wasn’t really that active on social media in general.
Just before that summer one of my other friends, Tim had a really rough breakup where he found out his college gf of two years was cheating on him. As the summer went on I wanted to cheer him up by maybe showing him hanging out with girls was still fun.
Since I didn’t know who else to turn to, I messaged Kate explaining the situation and she said that she would bring a friend and we could hang out and cheer up Tim. They aren’t 21 yet so a bar is out, so I suggest my place, so I can make dinner for everyone and we can play some games and maybe watch a movie.
Tim agrees and the day comes, I make a spinach and cheese lasagna and Tim brings snacks for appetizers. I hear the knock at the door that signals that the girls are and when I open the door I see two strangers standing before me. One a short, cute, somewhat chubby girl of Filipino decent and another girl who was skinny, tall, pale complexion, shoulder length purple hair, and a that looked like it was about to burst under the pressure of her breasts. The girl whom I was now staring at not so subtley said to me “Hi Matt, aren’t you going to invite us in?” A sheepish grin was starting to form across her lips. When I heard her voice I realized instantly it was Kate.
I couldn’t believe that it was the same person. “Holy crap, Kate, you look incredible!” I told her. I managed to pry my eyes away from her briefly to introduce myself to her friend. After the introductions Tim wandered over to the front door and had a similar reaction that I had when he saw Kate though his eyes didn’t linger over her as much as mine did. We ate, played games, and all throughout the night I was sneaking looks at Kate, not believing how hot she had become. We learned that she had gone from 220 lbs to about 155 lbs.
Thus why I almost didn’t recognize her. That combined with the fact she had posted no pictures of herself since her transformation or even during it. When we were watching the movie, I found myself staring at her wondering what it would be like to suck on her massive tits, or feel them against me as—I told myself to stop. As hot as she was now and even if he hadn’t treated her well she still used to have a thing with my friend Jake and it would definitely put a damper in our friendship if he found out about it. Still I was definitely interested in her, and maybe some part of me didn’t care about Jake, but I wanted to see her again after tonight. We said our goodbyes and fortunately Tim did have a good time and thanked me for hosting.
After that night I knew I had to see her again, but I didn’t know what excuse I could use to see her. I didn’t really want to straight up ask her out because of Jake, but at the same time I wanted to be around her.
Fortunately this problem solved itself as she posted that her family was hosting a party for 50 people and they needed help cooking. Seeing my opportunity I volunteered and she gladly told me to show up at her place on Friday at 2 pm and gave me her address. It turns out I was the only one that showed up early to help cook, though some of her other friends came later. Fortunately her mom and brother were there also to help. This gave us lots of time to talk, I learned that culinary school was going very well for her. We talked about all sort of things as we peeled about 10,000 potatoes, it turns out she’s was a giant nerd which worked out because I was as well.
Finally guests start showing up and we finish up cooking all the food (barely). I believe it was a retirement party of some kind for a friend of Kate’s mother. Basically it was a bunch of old people so Kate, me, and some of her friends that showed up late, grabbed food and then retreated to Kate’s room. I played some rock band with some of Kate’s friends, but noticed Kate was just sitting on her couch and wasn’t playing. When the song was done I passed the plastic guitar to someone else and sat next to Kate.
“why aren’t you playing?” I asked her
“because I can only play real guitar not the fake kind?” she said with a grin pointing towards an acoustic guitar sitting in the corner.
Intrigued I asked “can you play me something?”
she agreed and after the rock band song finished she played me and her friends a song. I was transfixed. I knew I was in trouble.
after she played us a song we all kind of just sat around talking and I learned that most of her friends really did not like Jake at all and were skeptical of me at first because Jake was a jerk to them because he just always wanted to be alone with Kate. I was beginning to not like Jake very much as Kate was a sweet girl, and pieces were starting to fit together that he was just using her. Kate all but confirmed this by looking at the floor.
I apologized for his behavior but they assured me that I was much nicer and to not worry about it. The night continued and as time went on I wanted to make some kind of move, but was conflicted because of what Kate’s friends had told me. I eventually decided that I was still going to make a move, but a small one. I was still sitting next to Kate who was leaning back and had one leg over the arm of the couch and the other pressed against her chest which I couldn’t help but steal glances at the whole night.
“is that uncomfortable?” I said gesturing to the position of her legs.
“A little” she replied
“here let me help you out” I said and grabbed the lower part of her legs, turning her towards me as I put her legs across my lap. “is that better?”
“Yes, much” she said a little shyly.
She didn’t move from that spot for the rest of the night, but she would occasionally rub her legs against mine, and eventually I found my hands resting loosely on her knees. we silently would play this game where she would slowly push her kneecap into my palm and I would try and grab it before she pulled back. Eventually the night wore on and her friends start to filter out and go home. As her last friend is leaving she closes the door behind her and says with a chuckle “don’t forget to use condoms you two”. Both of us laugh nervously, knowing that there is a bit of truth in her words. When she leaves we kind of both sit in silence not really knowing what’s next.
she breaks the silence first “sooo I actually have a boyfriend”
“oh” I replied as my heart began to sink.
She saw my face and quickly clarified “but we’re in an open relationship.” Now I must have looked confused at what that meant because she went on to elaborate.
“my boyfriend lives on the east coast, we do long distance and we’ve been dating for 4 years, but now we both want to have sex but don’t have the money to visit each other all the time so we opened up our relationship.”
“soooo what does that mean?” I asked as my hand moved a smidgen up her thigh. She let out a short sigh
not breaking eye contact she said “I have to clear everyone I want to have sex with by him” I could feel the tension in the room after she said that. Because now I knew she wanted me. She sat up, pulling her legs off my lap and says “I’m going to have to go to bed now before we do something stupid. I’ll walk you out?” reluctantly, I get up and walk with her to her front door. Our goodbye hug lingers as I can feel her boobs pressing into my chest. I let go before she can can feel my growing erection. I wanted to shove her against the wall and fuck her right there, But I made my move so the ball was in her court now. I was a little sad she had a boyfriend, but ultimately I was okay with it.
Over the next week or so we were texting nonstop, about mostly mundane things, but then one day she texted me “are you busy tomorrow?” I reply “no, not busy, what’s up?” she replies with “I got permission” and then sends a picture of herself in a black T-shirt and panties, her legs spread wide open. I was left speechless, I wasn’t expecting that at all, and I dumbly replied “Wow, that’s an amazing view” she just replied “lol I’ll see you tomorrow ;).”
We had decided we were going to go out to the renaissance fair with her and her friends. I didn’t have a costume so I just wore my puffiest dress shirt and jeans. I also brought along a change of clothes and left them in my car just in case. By this point I was perpetually horny imagining what was going to be happening later that night. I was still relatively inexperienced at this point in my life so the prospect of doing anything with a girl made me giddy and horny. What made it even more exciting was the fact that she hates using condoms and was on the birth control shot, and I had never done it raw before. We both had been tested recently too so it was extra fortuitous. I walked from the parking lot to our supposed meeting spot and I saw her and her friends chatting.
she was wearing a white blouse with a black corset over it that was really making her boobs pop, she also flowing white skirt that had a slit for her leg almost like a toga. When she saw me her eyes lit up and she rushed forward to give me a hug. As she pressed herself against me I realized she was not wearing a bra. That combined with the fact I knew I was going to be fucking her later gave me an instant hard on, which she noticed. “you’re excited a little early” she said with a smirk. She watched and blocked the view from others as I did the ever useful waistband tuck. She gave me a peck on the cheek and then we went around and ate drumsticks, played carnival games, and generally couldn’t keep our hands off each other.
As the day wore on we were watching a performance and I whispered something in her ear and she shuddered. I whispered close to her ear as I didn’t want to disturb the performance, and asked “are you cold?” She shuddered again. She slapped my arm and said, “no, stop doing that!” Perplexed, and wanting to tease her a bit I continued whispering into her ear. She finally got fed up with me doing that and walked away from the performance, fearing I upset her somehow, I followed her and asked “what’s wrong?” she turned around clearly flustered and said in a quiet voice “you ruined my panties” and it suddenly clicked that her shuddering was her getting turned on.
I felt a wash of pride that I was turning her on to such an extent. I couldn’t help but give her a wide grin. Kate gave a little smirk in return and said “it’s not funny”. Still holding my grin, I wrapped my arm around her shoulder and we walked back to the performance. It was starting to get late and we all decided to go back to Kate’s place and watch a movie to end the evening.
We got back to Kate’s place and Kate quickly went upstairs to go change her presumably soaked panties. Her friends quickly set about trying to figure out what movie they wanted to watch. To this day I could not tell you what movie they picked. Kate had come down dressed in pajamas with a blanket. we laid down on the couch with some of her friends on another part and others on the floor. As soon as we were comfortable she put the blanket over us and almost immediately my hands started exploring her body. She just had thin pajama pants on with a t-shirt, and my fingers slid into the crack where shirt meets pants and she gave out a tiny sigh and and push up against my body, giving me the greenlight to continue.
I slid my hand up towards her breasts but she stopped me and whispered “not yet”. Though a bit disappointed, I was quickly distracted by her ass pressing into my cock, which felt like it was about to explode from the day’s teasing. I responded by nibbling her ear and pulling her as close to me as possible. It was pretty clear at this point we were both so horny we could barely stand it. I’m honestly surprised I didn’t pull down her pants and fuck her right there friends be damned. But we both held back and fortunately whatever movie it was finished quickly. Her friends kind of got the vibes and exited pretty quickly after the movie ended.
—–Spicy Stuff—-
We headed up to her room, ready to finally act on our desires. She led me inside her room, and I shut and locked the door behind us. I had barely turned around when she put her arms around my neck and kissed me deeply pushing her soft body into me. I quickly returned her embrace and quickly cupped and squeezed her ass, she responded by shoving her tongue into my mouth.
We were both desperately exploring each others bodies, she was rubbing my bulge over my jeans while my hand moved up her torso and finally I grasped one of her huge breasts in my hand through her shirt prompting her to release a moan into my mouth. I was finally fondling her massive tits, but I wanted to see them so withdrew from our first (and very long) kiss and moved to lift her shirt over her head.
She put her hands up so that I could get her shirt up and as I pulled it up, her magnificent breasts bounced out in all their glory.
The were perfectly round and each dotted with a very erect pale pink nipple. I instinctively bent my head down so that I could suck on one of her nipples and Kate let out a sigh of pleasure, and as I take one into my mouth I give the other a light tug with my fingers as I knead it. At this point I’m in heaven and I feel Kate struggling to undo my jeans. I reluctantly stop sucking on her so that she can see what she’s doing and quickly undoes my pants. we return to making out and I feel her slip her hand into my boxers and starts to rub my cock.
This time it was my turn to let out of a soft moan as the feeling of her hand stroking my cock is amazing. She pulls away from our kiss a bit wide eyed and says “I wanna see it” and quickly pulls down my boxers. My cock springs out from underneath my boxers and she said “WTF Matt, It’s huge! It’s like as thick as my arm!” she held her arm up by my dick for comparison, it wasn’t that close from my perspective.
(For those wondering this isn’t an ego boost or anything, I do have a large dick but nothing ridiculous. its about 6.5 inches long and but also 6.25 inches in circumference aka It’s an above average length and thickness but nothing pornstary).
Kate tells me to lay down on the bed and I do and she hops up on the bed with me and crawls towards my cock, boobs swaying as she comes closer. Before I fully realize what she’s about to do she puts her mouth around my cock and starts bobbing up and down. I’m instantly in heaven as I feel her lips and tongue run the length of my dick. Every time her mouth goes down her soft tits press into my thighs.
I gently rest one of my hands on the back of her head not really pushing her down. I moan as she tries to take me into her mouth as deep as she can, when she finally comes up for air, I tell her to move her ass over closer to me. I don’t want to be the only one feeling good. She does and I immediately pull down her pajama bottoms and am greeted with a plump ass trying to hide a glistening pussy.
I can see the results of all the teasing on the couch as strings of grool stretched from her thighs to her slit. I started off giving her juicy ass a firm spank, prompting a muffled, surprised squeak from her. I explored her ass with my hands, squeezing and spreading it. I couldn’t resist any longer and ever so lightly traced my index finger across her sparkling slit. She sighed with my cock still in her mouth and my finger came away soaked even though I had barely touched her. I moved my hand back in front of her pussy, dipped my thumb in her juices and started rubbing her clit. I could feel the vibrations as she moaned on my cock.
As I rubbed her clit I could tell her sucking was getting weaker and weaker while her moaning got louder. As I rubbed, I coated my middle finger in her juices and gently slipped it inside her, and even with how wet she was her pussy was very tight. She clamped down on my finger moaning loudly now as I started to move it in and out of her, making sure to curl my finger so I hit her g-spot. Her face was now buried in my thigh, her teeth grazing my skin, blowjob forgotten.
As I pulled my finger out of her, I wet my ring finger and slid both fingers inside of her and she let out a surprised yelp and bit my thigh I started to fuck her with my fingers. Her moans were getting louder and she started to match the rhythm of my fingers with her hips, pushing back onto them. I could feel her drool drip down my thighs and her hand around my cock as she was meekly giving me a handjob. She could barely concentrate on it though and finally she pulled herself off my fingers, turned around, grabbed the back of my head and kissed me deeply her breasts pressing against me.
She broke of the kiss and looked me in the eyes and said:
“I want your cock, I need you to fuck me”
I pushed her down onto her back and positioned myself in-between her legs, I grinned as I realized that we were recreating the picture that she had sent me. I rubbed her clit with my thumb some more as I rubbed my cock in her wetness. It must have been torture for her because she started whimpering in a soft voice
“….Please…” “pleasepleaseplease” “pleasefuckme”
I answered by positioning the tip of my cock at her pussy and then leaning forward putting my face in front of hers and kissing her. As I withdrew from the kiss I put a hand behind her head and kind of cradled it as I slowly pushed myself inside her. Her mouth immediately made an O shape as she sharply intook her breath. Her eyes were closed and her brow furrowed as she pushed through the initial pain.
Her fingernails were digging into my back as I pushed further and further inside her. I could feel her pussy wrapped around my cock, stretching around me until I was balls deep inside of her. It was pure bliss. She was still getting used to me however and I started kissing her all over her face, neck, and remembering that her ears were sensitive, I sucked on her earlobe, which got a light sigh from her, then whisper in her ear:
“You feel so good, you’re so nice and tight for me”
I swear I felt her pussy twitch around me when I said that.
“you’re so big” she whispers back.
I start to move my hips ever so slightly and give her the tiniest of thrusts. She winces a bit, and I give her another small thrust, but this time no wince, I give her a third tiny thrust and she lets out a sigh of pleasure. I start to give her short thrusts, pulling back farther this time, and she responds with a soft moan and moves her hands to my butt and squeezes it, egging me on.
Our hips quickly find a rhythm as I glide in and out of her. My thrusts start to become longer and faster as my instincts and pleasure take over, each thrust now met with a wet slap and a loud moan.
“you feel amazing” she manages to say in-between moans and heavy breaths.
“you feel incredible” I say grunting as I thrust in and out of her.
It really was incredible. She felt amazing, I don’t even know how long we fucked like that, I could feel the passion when I kissed her, moans trapped and mixing between our mouths. It felt like my senses were dialed up to 11, I could feel her breasts pressed against me and jiggling with each thrust. Her room felt small, filled with the obscene sounds of grunting, moaning, and the slapping of flesh.
“Oh my god, Matt, you’re gonna make me cum” I could feel the desperation in her hips as she thrusted back against me frantically. She wrapped her whole body around me. Her pussy squeezed my cock hard as she started to cum
“fuck oh fuck OH FUCK I’m CUMMI–” her voice was cut off by her rapid breaths as her back arched and she started to spasm beneath me. I could literally see the waves of pleasure radiate throughout her body, I cracked a huge grin and enjoyed the feeling and sight of her orgasm. As it subsided she pulled me in close we kissed slowly and deeply. While we kiss I give her a small thrust, as my cock has been inside her this whole time and her body has a small spasm
“careful, I’m still really sensitive” she says with her pouty face on.
while she recovers, I play with her tits and we talk a bit.
“your cock is amazing Matt”
“well I think your pussy is amazing” I reply
“you’re just saying that” she says a little shyly
“no, I love how I can feel you pulsing around me” to emphasize my point I do a kegel inside her.
she gasped in surprise and smiled at me, then bit her lower lip looking at me with her big green eyes.
I took this as a greenlight and I leaned back, grabbed her hips and gave her a good thrust. she leaned her head back and moaned. she was was definitely ready for round 2. I start to fuck her in earnest, this time I can see her tits bounce, flop and jiggle around with each thrust, It’s not long though before I want to start fucking her hard, and I lean back into her and start really pounding her. she starts moaning loudly:
“oh fuck, FUCK ME HARDER” “OHYES JUSTLIKETHAT”
I was fucking her really hard now and I could feel my orgasm starting to build, fortunately so was hers:
“IM GONNA CUM AGAIN”
“I”m cumming too”
“CUM INSIDEEE MEE”
Kate was practically screaming at this point wrapping her legs and arms around me as I was pounding her hard, feeling close to release, and when I felt her pussy start to tighten it threw me over the edge, I pushed my cock as far as I could go and shot what felt like the biggest load of my life deep inside her.
Like before her whole body spasmed but this time it matched my own spasms as I continued to cum. We laid like that for a while kissing and enjoying the feeling of the post orgasmic bliss. Eventually though she unhooked her legs and I rolled off of her. She cuddled up to me, both of us still breathing hard.
“That was incredible” I agreed wholeheartedly as it was best sex I had in my life up to that point. And I told her as such.
We both fell asleep after that, exhausted from the exertion and the orgasms. I don’t know how much time had passed, but it was still dark outside when I was woken up by the feeling of hands stroking my dick. I looked down and saw that Kate was playing with my cock with one hand while the other was rubbing her pussy.
“mm I see you’re up…In more ways than one” she grinned at me as I chuckled and rolled my eyes at her joke.
“that feels nice, are you horny again?” she looks at me with her big eyes and nods.
“Do you want me to fuck you again?” she nods a second time.
“I’m already wet, I was playing with myself while you were sleeping” she said, showing me the grool on her fingers. I reached down to confirm and holy shit she was already soaked. She rolled onto her side so she was spooning me, all while still stroking my cock. My hands immediately started groping her tits and playing with her nipples all the sudden if feel the tip of my dick getting we and I look down to see her rubbing my cock on her pussy. She starts pushing her ass onto my cock and I grab her hips to help push myself inside her.
It goes in much easier this time, and with much less pain on her end. It still takes a minute for her to get used to me but it’s not long before she starts grinding on me. Things were much more relaxed this time since we were both no longer so desperate to fuck. This was slower and much more intimate. Kate’s hands stretched behind her as one ran through my hair while the other rubbed my ass. Before long she was moaning with each motion. I lazily moved my hand to rub her clit as I kissed her neck. I could feel my orgasm building so I wanted to get her off before I came.
“mmm, yes just like that” she gasped as I started to breathe heavily into her ear. “are you close?” she asked
“yeah, I’m gonna cum soon” I grunted in her ear.
“I want your cum, give it to me” She gasped as I started to rub her clit faster. She started moaning louder, and I could tell she was close, but I couldn’t hold back anymore and I shot my load into her for the second time that night. I felt her spasm around me right after and she said
“ohfuck I’m cummmming” She gripped the back of my butt tightly as she came, also grabbing the hand that was rubbing her clit so I wouldn’t overstimulate her.
We fell asleep like that, absolutely spent, and woke up the next morning with my cock still inside her. She was a bit sore from the night before so we didn’t do it again right then, we decided that we were going to take a shower, and that’s where her horniness took over and I fucked her doggy inside the shower.
This time I came on her ass instead of inside her because she didn’t want to deal with the mess throughout the day. As hot as that was for me to imagine, the practicality of it won out. After the shower I gave her a long kiss goodbye as we both had things to do that morning and I headed home.
Over the course of the next couple months we fucked in every position and every place imaginable. She especially loved when I would eat her out as I guess no one had really done that for her before. It was with her that I discovered I was pretty into public play when she rode me on a park bench, and she discovered that she really enjoyed being tied up and toyed with.
I had already decided that I was going to delay school another year for more money. This was partially true, but it was also because I was having such a good time with her and I didn’t want it to end.
Source: reddit.com/r/gonewildstories/comments/u5dbnc/mf_the_time_i_accidentally_cucked_two_people_part