My roommate.
So up until my daughters moved back in with me permanently I had a roommate. She was decent looking and had a boyfriend that lived about 45 minutes away so during the week she chilled at the apartment a lot and she would visit her boyfriend on weekends.
This worked for me because on weekends I would have my FWBs visit. During the week occasionally too and my roommate would get the hint and go to her room rather than hang out in the common areas.
Something happened on a Wednesday and the reason I remember it was a Wednesday was because that my errand day. Groceries or anything else on that day seems to go quickly as long as it’s not the first of the month.
I get home around 7:30 and start to unpack the car and the roommate, we will call her Joan, comes out to help me bring in the groceries in.
She asks me if any of my FWB are coming over that night so she can watch a movie on the couch in the living room. I tell her it’s all clear and I might join her after I have my dinner.
She always wore a big t-shirt and old PJ bottoms that hid her figure. She was curvy, but had a significantly thicker ass than boobs, but still generous. I would be lying if I said I didn’t notice. She had wavy black, shoulder length hair and green eyes. Pale even for a white girl.
I cook up some thinly sliced potatoes chicken breast and broccoli and seasoned it heavily. My roommate asked if she could try it so I made enough for her to have some. I brought the plates to the coffee stand and shooed away both my cats so they wouldn’t try to sneak any of the food. I opens up a cheap bottle of Riesling and got a couple glasses.
My roommate thought this was fancy. It was not and it added to my assumption that she didn’t grow up with any kind of culture outside of pop culture. She ate pop tarts for breakfast as an adult for fucks sakes.
Any way.
She is nice enough to pick up the plates and take it to the sink, but doesn’t wash them right away which bothers me, but I didn’t want to seem ungrateful so I just chilled on the couch and continued to watch whatever it was she picked. I want to say it was something called Pitch perfect. I’m not a fan of musicals so I pretty much zoned out.
I notice after a couple glasses of wine that she’s not back so I go to do the dishes. Just as I’m finishing up I hear her come out of her bedroom and come up behind me. I assumed she was bringing her glass to be washed, but I felt her gaze on the back of my head.
When I turned she said “we need to talk”. Oh what the fuck I was thinking. She’s going to say she won’t have the rent this month or some shit like this. Instead she says to me that she knows I know she’s in an open relationship.
I nod. Then she tells me she got off the phone with her boyfriend and she got permission to have sex with me. I shrugged as told her that’s fine, but she won’t sleep in my bed when we are done. I don’t care how tired she is.
I told her to strip for me and she did without any hesitation. She dropped to her knees and I told her to her up. I’m not a huge fan or blowjobs unless I can tell the woman really wants to give a blowjob rather than treating it like a obligation.
I take her by the hand and take her to my room and tell her to get on my bed and lay back with her legs open. I ask her very clearly when the last time she was tested and she told me three weeks. Then I asked her if she’s fucked anyone other than her boyfriend since that time and she hadn’t. Good enough for me. I told her I was going to fuck her raw and get pictures of the mess I leave her for myself and her boyfriend if he wanted them.
I lowered my head to her pussy and began doing what I love. Licking up her lips and sucking on her clit making her do those beautiful pleasure spasms as my mouth did the work. Her moans filled my room and I looked up at her as she pinched and played with her nipples. I don’t know how long I stayed down, but she was grabbing the back of my head and looking at me in the eyes.
She told me clearly that she needed to feel my cock. I got up and balanced myself on my knees between her legs put a pillow under her ass to raise her hips so I could pound her right. I slid my cock head up and down her dripping lips and looked into her eyes. I would occasionally tease her by sliding in just a few inches. I loved the look on her face. I knew it wouldn’t last long when she put her hands on my hips and tried to pull me deeper into her so that’s exactly what I did.
Sliding all the way into her wasn’t as easy as she thought. I bottomed out in her and her eyes were peeled looking into my eyes and she cried out in pleasure and pain. I lifted her legs and almost folded her over and just started pounding away into her so deep and making sure I used my thumb to keep playing with her clit. Then it happened. The infamous squirt. It’s not like in movies. It’s not this fountain of squirting. It’s a slow, but obvious gush and once you’ve been a part of it you know it.
She came so hard and clawed my back and shoulders. She started begging for me to cum, but I wasn’t ready and I really wanted to fuck her from behind and spank her ass that I’ve always stated it. I told her to shut up and turn over.
She obeyed without any hesitation, which I really liked. Her ass was so thick and juicy, but I wanted a better view so I reached over and clicked on my reading lamp and it gave me just enough light so really get a good look at her ass.
She had a tramp stamp of an eagle that was kind of tacky, but still a nice place to look at. I pushed her head down to the pillow so her ass would be up in the air for me. I looked at her asshole and saw that even though her pussy was nicely trimmed he asshole was perfectly hairless. Made me think that maybe she was planning something with her boyfriend this weekend.
I spanked her soft at first and then slowly increase the force of my impacts. I made sure the sound of the spanking was loud and clear enough to echo and I kept encouraging her to be my good little slut. I could see he pussy dripping the longer I spanked her. Her right ass cheek was getting nice and red from my right hand. My left hand was either pulling her hair or getting in the occasional spank on her left cheek then squeezing it and teasing her cute little asshole.
She started meaning for me to just fuck her already. I was so hard and my precum was a steady stream, but I was enjoying this too much. Then it happened.
“Just play with my ass first to get me warmed up if you want to fuck my ass.”
I did not expect this. I told her that’s fine if she wants me in her ass, but I’ll need to get the lube. I slid the toy box out from under my bed and got the lube and climbed back in the bed. I told her I would fuck her ass like she wants but I want to see her face when I slide into her. So I made her get back on her back.
I put the same pillow under her ass and lifted her legs again. I went down again, but this time I was focused on her ass. I don’t play around. Licking and circling her asshole and using my fingers to prep her then I started to add a generous amount of lube and started to slide one finger in her then two.
I used my thumb to keep giving her clit attention. When I welt like she was ready. I got back into position between her legs and aimed my cock at her prepare rosebud. Just the tip of my head was in and I stared into her eyes and she looked like the wanton slut I knew she could be but also so scared. She whispered that I’m bigger than her boyfriend so I need to take it easy.
I was easy on her, but firm. Very firm. Adding more lube I slid into her until I was bald deep and she inhaled and cried out grabbing me and pulling me to her. Her ass tightening around my cock like a warm accommodating vice. She breathily kept telling me she loved my cock and needed me to please take it slow until she got used to me. I started to grind my hips and reminding her to breath.
She moaned and bit her lip and grabbed the pulled to the side of her head and looked like a demon, but I was tired of waiting. I added a little bit more lube and then set the bottle aside and grabbed her by the head using my arms to hold her legs back and started to fuck her like I didn’t care anymore because really I just needed to feel her. At first she looked so scared when she made eye contact, but then slack jawed and with tears in her eyes she started to nod. She then told me to fuck her harder
She didn’t need to tell me more. I relaxed myself and and then started to pound away into her grunting with each deep thrust into her tight ass. She started to cum again and needlessly told me she was cumming, but I felt it her ass tightening and there it was again she squirted. I would have to throw out that pillow.
Her ass tightening from her orgasm pushed me over the edge. Apparently my last deep thrust was too much for her because she yelled out, but she held my ass and pulled me in deeper as I cum so much deep inside her. I came so much she kept telling me she could still feel me spasming in her ass. I pulled out and did that after sex shuffle to get to the shower so I could wash my dick off Incase there was any shit.
There was none. It hit me that she was prepared for this. She cleaned herself out in preparation for me. I wondered how long she planned this. And then I wondered if her boyfriend really did give her the go ahead. He did, I found it later and one time he joined us and we DPed her on her bed when he visited.
This was the start of me fucking my roommate pretty regularly both alone and with my other FWBs and her boyfriend.
The primary itch she needed scratched was my thick cock in her ass as often as possible. One of my FWB got a little jealous because she’s never been able to take a hard fuck in the ass like Joan could do when she witnessed it. She thought I would stop giving her the cock, but I don’t expect all of my partners to be the same.
Joan and I are still friendly, but since my daughters are with me full time now we haven’t had a chance to really get down to business like before. Good news is that this Wednesday coming up I’ll be able to see her before she goes to work. I’ll