Fucking My Cougar Roommate [MF]

If you wanna skip to the sexy bit, scroll to the line of little buttholes *****

About a year before I met my wife, I lived in a giant condo with two female roommates. I found the place on a roommate finder website, and I think they wanted a male there to feel a bit safer. It was a really nice part of town, but you never know I guess.

The owner of the condo was mid 60’s, unattractive. The roommate, I’ll call her N, was super boring and buttoned up (or so I thought). She had a pretty face, and a rockin’ bod, but she was a workaholic who never went out.

We never really hung out together, but we were friendly enough and would occasionally eat meals together if our schedules lined up. I’d try to flirt, but she never seemed into it. We lived there for almost a year before the owner decided to move back to her hometown. She gave us six weeks to find other living arrangements. It was during our last week of living there that the cougar pounced.

I was taking my nightly trip to the roof to smoke a joint. To get to the stairwell I had to walk through the kitchen. N was in the kitchen waiting for me, pretending to put dishes away. She asked if I was heading up to smoke, so I held up the doobie affirmatively. She reached behind her to grab a bottle of tequila and two shot glasses from the counter behind her, held them up, asked if she could join me.

Once on the rooftop, we took a couple shots and a couple tokes, and had our best conversation since knowing each other. No small talk, we got deep, excited to listen to each other’s stories, really connecting. She sat atop an electrical box kinda thing while I stood. We passed the bottle of tequila back and forth, forgetting the shot glasses.

We eventually got to the topic of dating. She noted that I sure seemed to “date” a lot. I was on the apps quite a bit back then, an ethical fuckboy but a fuckboy nonetheless. I asked her why she didn’t date more, told her she was very pretty, had an excellent figure. I asked about her ex husband, and if she had any fun dating stories or sexy adventures.

She went on to tell me about her very eventful past, things I truly couldn’t believe. In her youth she had been a groupie for some band, had traveled around with a fucking motorcycle gang. She had frequented sex clubs, sometimes as a single, sometimes as a unicorn for a younger couple. She attended many orgies and sex parties with her ex and on her own. As she told me this I could see her nipples harden through her shirt and sports bra.

I asked why the hell, if she’s such a naughty woman, wasn’t she dating or fucking anyone. She said she was always so busy, tired, stressed, she’s so “old” now, it’s easier to just get herself off, blah blah blah. I complimented her beauty, said she could easily land a man, or at least a fuck buddy. I also complimented her gigantic rack, said it would make finding someone that much easier.

Then she told me another shocking fact. Her big titties used to be even bigger! She’d gotten a reduction/lift a few years back. This was truly shocking. She always dressed fairly moderately, but it was obvious she had massive tits, there was no hiding it. She made sure to tell me there was nothing fake inside, it was all her. The fact that they used to be bigger was shocking. I was feeling pretty good, a little high, a lot buzzed, confident this was more than flirting.

(**************************************)

I told her to show them to me. She bit her lip like she couldn’t fucking wait to show me. She looked around to see if anyone was watching, as did I. The rooftop was clearly visible from the windows of neighboring buildings, but there didn’t seem to be any peepers.

She pulled her shirt and bra straps down over her shoulder, pulled her arms through. I was already getting hard as she prepared to pull the top down and flash those huge boobs I’d thought about many times before. She smiled as she pulled the fabric down, exposing beautiful breasts. The surgeon had done a fantastic job with the lift. Nips were well placed, nicely shaped, scarring was minimal.

I moved in to kiss her, one hand caressing her neck and face, the other feeling her up. Her tits were so soft, her nipples so hard. She was a great kisser, and because she was sitting on the electrical box, she was at the perfect height for me. I had to get those nipples into my mouth. I leaned her back and worked my way down kissing her soft skin, then sucking her nipples. I nibbled and played with them while my hands squeezed and groped her.

My cock was straining against my basketball shorts. I told her how hot she was and how hard she made me. She told me to show her my cock. I’ve always been an exhibitionist, love showing off. My heart raced as I looked around to make sure we still didn’t have an audience (though it would have made it hotter, let’s face it), then pulled the elastic band down. My dick sprang out and stood at full attention.

She complimented me, seemed surprised at my size. I’m not all that girthy, but I’m about 8 inches long. She grabbed my dick as I caressed her big tits. She told me to trade places with her, that she wanted to suck me.

I hopped up on the electrical box, and she started going down on me. When I say going down, I mean all the way down. This was in fact my first and only deepthroat experience in life. She took me to the base on the first try, and I was shocked. It actually kinda hurt, which was a sad realization. It looks so cool in porn, but it’s really tight and kinda bony at the back of a throat. It didn’t hurt so bad that I told her to stop, and she didn’t do it the entire time. She was showing off basically.

She blew me for a few minutes while I moaned and groaned and squeezed her soft tits. I said I wanted to head inside and return the favor. She moaned in agreement around my cock, kept sucking for a minute or so, then we went in. We stumbled to her bedroom, trying not to wake up the old lady, but we were pretty tipsy and I feel like N wanted the old bird to know we were up to something.

Once in her room, we disrobed and I went down on her. I ate her pussy while she moaned and played with my hair. As I licked and sucked, I reached up to feel those incredible boobs some more. Soon, she asked me if it was okay if she got a toy out. She wanted me to straddle her chest and fuck her face while she used her Hitachi. She said I was good at eating pussy but it wasn’t her favorite, she wasn’t able to cum that way.

We found a good rhythm, her mouth working its wonders while the wand worked its magic. She liked it rough, instructed me to use my weight. I fucked her face slow but hard, forcing myself deep into her mouth. She came within minutes. I asked if I could fuck her tits. She brought out some kinda sweet smelling lube and slathered her cleavage and my cock in it. Her pillowy jugs felt so fucking good enveloping my dick. She held them together for me. I used my free hands to pinch her nipples. I soon slowed to a stop, told her I was gonna cum soon.

She told me she needed to pee, that when she came back I was going to fuck her pussy and then her ass. I was glad for a short break to let my building orgasm subside. I actually had to pee too, so I went when she came back, and when I returned she was getting herself off with her magic wand again.

I lay beside her and watched. I started fondling her tits with one hand and my cock with the other hand. Once hard, I sank into her. The combination of her sweet pussy and the vibrations were next level. She came shortly thereafter, the toy and my cock doing their jobs. I wanted her on top then so I could play with her breasts while she rode me.

I was getting close again and let her know. She dismounted me and flipped around to present her sweet ass. She was face down with her hands spreading her cheeks. I carefully placed my cock, soaked with her pussy juice, at the entrance of her ass and began to push. I was gentle at first, but before long I was pounding myself into her while she muffled her cries into her pillow.

I told her I wanted to cum on her face and she begged me to make it happen. She got on her knees for me, but not before grabbing her wand once again. She made herself cum while I fucked her mouth, and then I unleashed a sizable load onto her eager face. She looked so hot as my big thick load of cum dripped down her chin onto her big tits.

We did it again in the morning, and several more times during that last week of living in the condo. We live in different cities now, but still send naughty texts once in a blue moon. I miss you, N!

Source: reddit.com/r/gonewildstories/comments/og9fw0/fucking_my_cougar_roommate_mf