I met Annie in a Pickleball class. That’s right, [Pickleball](https://usapickleball.org/what-is-pickleball/). I had gotten into a bunch of drugs during my sophomore year and my grades reflected it, so to boost my GPA, I started taking a bunch of easy phys-ed classes that graded mostly on attendance/participation. That’s how I met a lot of hot girls in my junior and senior years of college. Annie was one of them.
Annie was on the bigger side, roughly [5’5”, 200lbs](https://app.mybodygallery.com/#/?height=165&weight=91) but still definitely pretty. We joked, flirted, and had a lot of feisty, competitive banter on the Pickleball court, but I didn’t really expect it to go anywhere. Not expecting anything made it easy. We just had fun and enjoyed our time together with no pressure, no expectations.
When the term ended, we still saw each other around campus and always said hi. Then one summer night, I bumped into her at a bar. We were both pretty drunk by the time we decided to walk the mile and change to her house. It must have been between 1 and 2 AM when we decided to stop in a park and lie down in the grass, looking at the stars. I leaned over and kissed her there, and after a little light making out, we were soon back on the way to her house. It was empty when we arrived, her roommates all gone, and after a few cups of water, we went back to making out.
Our clothes were soon on the floor and we moved to the living room. There was no furniture in the room, so I ate her out on the carpet for a while, until she laid a kitchen towel under her ass and told me to fuck her. Sex on a rug is not comfortable, and I’d generally advise against it, but in the heat of the moment, I wasn’t complaining. I remember when we switched to doggy style, I looked up and realized that the entire south wall was one huge window without any curtains. Though the lights inside were dim, it still meant that anyone could be outside watching us, and all I could see was our reflection in the glass. I looked down and watched my cock disappear inside her, her tight lips doing their best to hang on with every backstroke. After that, I leaned over to the side and watched her titties swinging as my hips slammed into her ass, then I glanced up at the glass and watched the same action from a different angle. The thought that someone could be out there made it even hotter and combined with the visual reinforcement of being able to watch our own reflections, it didn’t take long before I started filling the condom with cum.
After collapsing on the carpet and catching our breath, we cleaned ourselves up, went upstairs to her room and got in bed, but were unable to sleep so we talked. This was relatively early on in my sex life, I think she was probably the 8th or 10th girl I’d been with. Out of curiosity, I asked how many people she’d been with. Her answer was in the 80s and I was both surprised and impressed. When she asked me, I lied and said she was my 19th. She said it’s a lot easier for women, guys will basically just line up. At one point, she mentioned that she had fucked my roommate. He kept trying to put it in her ass and she had to say no over and over. Then almost like an afterthought, she said “Even if he had, it wouldn’t have been that bad, because he had a tiny dick. Nothing like yours.” I’m 7.5”/19cm, so not huge but big enough to be appreciated. Hearing her compliment me got me really turned on, though, and pretty soon we were fucking again. Classic missionary, but between being pretty drunk and having just fucked, it took me forever to cum. After I flushed the condom, cleaned up, and got back in bed, she snuggled up and said, “You were like a fucking machine. I must have cum 7 or 8 times.”
About a year later, I got a text from Annie. She was too horny to function and needed some dick, so I was quick to head over to her apartment. (This wasn’t the first time I had been to her new apartment, but that’s [a story for another time…](https://www.reddit.com/r/gonewildstories/comments/i5bfsw/the_first_time_i_m_was_invited_to_a_threesome/)) When I got there, I was greeted by a gorgeous blonde woman who I’d never met before. [She was about 5’10” and probably weighed around 150, with smooth curves from her waist through her hips to her thighs.](https://app.mybodygallery.com/#/?height=178&weight=68) At first I wasn’t sure if I was at the right apartment, but I told her I was there to see Annie and she invited me in. She introduced herself as Kelly, one of Annie’s roommates. Kelly informed me that Annie was in her room with a friend but I was welcome to hang out on the couch with her while I wait. I could hear the headboard banging against the wall and did the math.
Unsure what to do, I started talking to Kelly. After about 15 minutes of getting to know one another, I asked if she was in a relationship. She complained about her boyfriend, saying that she was in the process of breaking up with him. I remember her saying that she was 29, worried about her biological clock ticking down, and she didn’t want to waste it with him (although 10 years later, she still looks amazing).
We exchanged phone numbers and she actually ended up texting me some of her nudes right there on the couch. *Damn!* Her body was amazing! Big, perky D cups with delicious looking nipples led the way down a smooth stomach to her clean shaven pussy. I had to go to the bathroom and when I finished peeing, I looked at the pics she sent and started rubbing my cock. Once it was nice and hard, I stood in front of the mirror, snapped a pic of my dick, and texted it to her. This was right after the Motorola Razr craze but before iPhones were really a thing, so picture quality was limited, but barely acceptable. When I got out of the bathroom, she was incredulous. Her response was essentially “no way, you just found some random pic online.” I said, “that’s the same shirt I’m wearing right now, that’s your bathroom mirror, products, toothbrush, etc.” That’s when she told me to prove it, so I pulled out my semi-hard cock for her. Kelly blew me right there in the living room while I could still hear Annie getting fucked in her bedroom. I came way faster than I wanted to and Kelly pointed out some napkins on the kitchen counter.
We hung out on the couch a little longer and she assured me that she would reach out to me once she broke up with her boyfriend. Eventually, a black guy who was at least 6’6” came down the hall and walked out the front door. Then Annie came out of her room and was shocked to see me there. Kelly excused herself for what was about to be an awkward conversation and I ended up going home, but it was alright since I basically got what I had come for.
In the months that followed, we exchanged a few nudes, but she never did tell me that she had broken up with her boyfriend.
The following winter, I was at a bar with my friends when I bumped into some classmates. Bethany was hanging out with her boyfriend when she turned to a sexy chick she was with and the two of them started making out. A third girl joined them and I stood there with a couple other guys—including her boyfriend—just watching the three of them go at it. I recently found the micro SD card from my old phone and apparently I took a [photo](https://imgur.com/b7oGHgy) of them.
When they separated, I realized that the third girl was adorable. [Maria was barely 5 feet tall, and couldn’t have weighed more than 95 lbs.](https://app.mybodygallery.com/#/?height=152&weight=41) She had just broken up with her boyfriend and was out to have a good time. We spent the night hanging out and talked a lot. It was one of those connections that was too easy. I ended up driving her home and when I was dropping her off, just as she was opening her door to get out, I took her hand and when she turned back toward me, I leaned in and kissed her. She kissed me back so hard and left with a big smile on her face.
We texted back and forth and within a day or two, she asked for my address and soon she was at my door. Looking for something to fill the background, I rummaged through my DVDs and threw on a random episode of Always Sunny In Philadelphia, not even realizing that I had picked my favorite episode. Soon she was singing “Dayman, fighter of the Nightman…” along with the Charlie and confessing that it was her favorite episode.
I’m not sure whether or not we even finished the episode, but soon we were in my bedroom. I was about to go down on her when she beat me to it and started working her way down my chest. I helped her get my pants off and she started sucking my cock, gagging on it like she wanted to deep throat but just couldn’t get past the tonsils. She stopped to take her clothes off and I pulled my shirt off too. She asked if I had a condom and as I was about to open it, she pulled it out of my hand and did it for me. Then she leaned forward and kissed me as she straddled my hips. She guided my stiff dick inside her tight pussy and started slowly rocking back and forth. Her perky tits were swaying back and forth as she grinded her clit into my pelvic bone. With my cock buried deep inside her, she started moaning quickly. We switched to doggy, then missionary, and back to cowgirl until she made me cum.
She got dressed while I lay naked on the bed, watching her. Just before she left, she came to me, kissed me hard, and said “You have a big dick.” I’d heard suggestions and hints from chicks I’d hooked up with, but never had someone just come out and said it to me like that. We fucked a few more times and had a lot of fun. One time she came over and I ate her out for over an hour before she sucked the cum out of me. My roommate was watching tv in the living room when she left and he looked her up and down with an impressed look on his face before giving me an approving nod and thumbs-up.
Then one day, I found out that Maria had gotten back together with her ex-boyfriend. I’m not sure if she’d been using me to make him jealous, if she needed a change of scenery, if she was trying to sort out her priorities, or if something else was going on. I wasn’t looking for a relationship in those days, but it was still disappointing when she was gone.
Annie called me. She was pissed, yelling at me at me for hooking up with her roommate. How could I?
Hold on, this was the first I was hearing about this. Wait, Maria was Annie’s roommate? I’d had no idea. But Annie was livid! I hope she didn’t know about Kelly, too.
Annie eventually texted me again, she wanted me to come over. I spent the night lying next to her, but we didn’t fuck. This was basically my punishment for banging her roommate. I thought about getting up in the middle of the night to hook up with Kelly, but when I opened the door, I could hear the sounds of her getting fucked hard (she was very vocal) so I just took a piss and went back to Annie. It was a pretty disappointing night.
Years later, the winter after I moved into a new apartment, I got a text in the evening. Kelly was going to be back in town for a day and was looking for somewhere to spend the night. I gave her my address and did a quick once-over through my apartment, relieved that I didn’t have a roommate. When she got there, it was late and I was playing guitar. I had just mastered the fingerpicking on Fleetwood Mac’s *Landslide* so I played it for an audience of one and she hung on every note.
After some drinks and a few more songs, it was bedtime. I asked if she wanted the couch or the bed and Kelly said she’d share the bed with me, but we weren’t going to do anything. She asked if I had a big shirt she could sleep in and undressed right in front of me. I admired her curves and could barely take my eyes off her perfect tits when she took her bra off. I got a great glimpse of her ass in a thong when she bent over before climbing into bed. I’d seen it all before in the pics she texted me, but seeing it in person was something else entirely. I had a bulge poking forward as I stripped down to my boxers and got in bed next to her.
Despite having a cozy down blanket and space heater on in the bedroom, she said she was cold and rubbed her smooth legs against mine. I reached an arm around her and scooched up against her flawless body. My hand moved up under the shirt and slid along her soft skin to her big titties. She asked what I was doing as I traced little circles around her nipples. “Just warming you up.” She told me I was making her horny and I answered that I knew a good solution to that. I ran my hand down her stomach and inside her panties, gently stroking her pussy. I could feel she was already soaking wet and I pressed my finger between her lips, gliding up and down in her juices. I rubbed her clit for a bit and she turned in the bed, spreading her legs and giving me better access.
Then I lifted the sheets and disappeared under them, moving down to eat her out. I ran my tongue up and down between her lips sucking them into my mouth. Then I drew little circles around her clit with my tongue, pulling her hood back with my finger and flicking my tongue over it until she moaned for me to fuck her. I had a few condoms nearby and soon I was inside her, missionary style. Kelly was a very talkative girl, telling me how good it felt and how much she liked what I was doing. When I started going faster, she would say stuff like “Stuff that big cock into my cunt.” and “Tear my pussy apart with your dick.”
After a few minutes of that, I pulled out and she rolled onto her front. I stayed on top of her, sliding my cock back inside her from behind. When she wasn’t moaning loudly into the pillow, she was telling me how good it felt and how much she wanted more. It did wonders for my confidence, especially the several times that she announced to me that she was cumming. Eventually, I started losing some momentum so I laid down next to her, spooning her from behind while I moved in and out of her tight pussy. I reached down and lifted her leg up, holding it in the crook of my elbow so I could squeeze her titties as I fucked her. She loved this, telling me that I was hitting all the right places and that I was going to make her cum again. She begged me to please cum with her and when she called out that she was cumming again I stopped moving and could feel her pussy clenching around my cock. This pushed me over the edge and suddenly my cock started throbbing inside her as my own orgasm overtook me and I blew my load into the condom. I let go of her leg and relaxed against her. She told me not to pull out, clutching my arm to her chest until we both fell asleep.
I had to wake up early for a 6AM shift and when my alarm sounded, I found a shriveled, cum-filled condom still barely hanging on around the tip of my flaccid cock. I got up, trying not to disturb her, but she woke up anyway. I told her that I only had to work for 1 hour and she was welcome to anything in the apartment. 7:00 finally came around and I hurried home, careful not to slip on the icy sidewalks. When I got inside, Kelly was still asleep in my bed.
I only worked a block away, so I didn’t bother putting on winter clothes for the short walk and as a result, my body was freezing all over when I got inside. I remembered reading an article about girls who enjoyed stuffing ice cubes in their pussies because the cold sensation felt so intense and good. Without saying anything, I stripped, then lifted the blankets from the bottom of the bed and crept under the sheets, up between her legs. I began gently touching her pussy with my freezing fingers. She got wet quickly and as I slid a finger inside her, she jolted awake. “Fuck that’s cold!” she said, but then started moaning when I pressed against her G-spot. I stroked it gently at first, gradually increasing the pressure. Then I crossed my first two fingers like I was hoping for luck and slid them inside her, twisting back and forth like a corkscrew inside her tight cunt.
Her moaning soon turned into her demanding that I fuck her. I crawled up to the top of the blankets and was about to reach for a condom when she grabbed me and started kissing me. While making out, her warm hand clutched my cock and guided it between her lips to her hole. I pushed my bare dick into her, relishing the enhanced sensations of pushing inside her pussy without a condom. I fucked her missionary for a while until she turned over and we started going doggy style.
I enjoyed the view of her sexy body while my own personal cheerleader encouraged every move I made, telling me to fuck her hard from behind, I recorded a mental video of her pussy gripping my cock as it slid in and out of her. I captured the gorgeous curves of her ass, hips, and waist as I gripped her hips in my hands and plowed into her from behind. I bent to the side and watched her tits swing back and forth while I slammed my hips into her bottom. She had her head down, hair spilled over my pillow and a huge smile on her face as she looked back at me. I considered grabbing my phone and taking some pictures/videos but it was across the room in my shorts and I was enjoying her way too much to pause. I bent forward and slid my hands up her sides until I could grab her tits, squeezing them and pinching her nipples. Then I straightened up and smacked her ass, leaving a bright red mark in the shape of my hand. She let out a moan and bent forward, arching her back and leaning into the pillow with her shoulders.
With her ass pushed up like that, I looked at her pretty asshole and placed my hand in the middle of her lower back, resting my thumb on her butthole, where I rubbed it while fucking her pussy. She admitted to me how good it felt and I thought about pushing my finger inside just a little bit when she started cumming loudly. I tried to keep moving inside her but she slipped loose and collapsed on the bed, panting for breath.
Then she rolled onto her back and lifted her legs into the air. I stuffed my dick back inside her and crossed her legs in front of my chest. She told me how much she liked it and I could tell I was getting close. I asked her where she wanted my cum. “You could cum inside me if you want… Or you could cover my tits.”
I had never cum on anyone so I pulled out and shot the first load right across her chest, she sat forward, catching a second rope on the tits and a third that got away from me and hit her in the chin and lips. The fourth blast connected with her shoulder and splashed up, shooting across my bed and onto the wall. She grabbed my dick and jerked the last shots of my cum into her hand. Then she rubbed it across her huge tits while the load that got her in the face dripped down her chin onto her chest. I got a towel, wiped her face and planted a kiss on her lips.
After that, we got up and showered together. Watching her lather her tits with soap was getting me turned on again. I realized that I wanted to pump a creampie into her cunt that would spill out into her panties while she was trying to meet with clients or friends or whatever she had planned. I got hard in the shower and when she was turned around, I moved close and slid my cock between her legs, pushing inside her for one last fuck. I slid my hands up her soapy stomach, squeezing her tits as I pumped into her, and she reached back, grabbing my hair and pulling my head so that our mouths met. Unfortunately, shower sex is a lot more complicated than I had expected and I just didn’t have it in me so we ended up quitting after a few minutes of awkward thrusts.
A few months later, she texted again to say she was in town and we met up at the bars, but after a few drinks, she saw a mutual friend who she hadn’t seen in ages and started grinding up on his crotch. I didn’t even fight it. Looking back I wish I had stepped in and taken her back to my place.
A while after that, a friend of mine bought a used stretch limo and wanted to take it on a test ride before he officially started his limo business. The plan was to go to an annual festival in another city. Not wanting to go solo, I extended the invitation to Maria, who was single at that point, living at her mom’s. When she arrived, she had gained at least 70 lbs, but still looked cute enough. Then she told me that we wouldn’t be hooking up, she was doing a chastity thing and trying to be a better person. Whatever that meant. That put a damper on what otherwise was a great trip.
I graduated and moved away 8 years ago and since then, I haven’t heard from Maria or Kelly, but Annie and I still talk. She got married a few years ago but we still share nudes and talk about hooking up the next time I’m in town. Also, the names have been changed.
Source: reddit.com/r/gonewildstories/comments/i5baa8/i_m_banged_3_roommates_fff