New Roomie (Part 23) [milf][slow][anal][milking]


This is a multi-part story of how my girlfriend’s friend (Rachel) turns out to be an anal slut and our numerous adventures together as she becomes my roomie for six weeks. This story contains blowjob, butt plugs, anal play, assfucking and cheating.

You can go from here or read the series where Rachel and I have all sorts of dirty things going on. If you’re under 18, please close this site and leave. Note: English is not my first language so please excuse any mistakes and let me know if you’ve enjoyed it and whether I should continue.

The rest of the afternoon went by rather quickly and Ellen seemed to have gone for the day too, which for me meant at least a break from licking her ass over and over again.

Not that I was complaining tough, it was super-hot, but after a few day’s I’d gotten desperate and wanted to eventually take my boss’ ass at some point. But I was working on that.

Linda seemed satisfied too for the day after I drilled her ass roughly on the terrace of the office building, and so I found myself sitting in my office, fantasizing about what Ann had planned for our dinner date at her place tonight.

Soon I was on my way home, showered, and put on some fresh clothes, wearing jeans and a white shirt untucked, when she texted me that she’d be ready for me to come over in about fifteen minutes.

Even though I’ve had plenty of hot events with Ann in the past, I still was a bit nervous about meeting her for a ‘dinner date’ as she had that aura around her which only a mature woman can have.

I made my way over to her apartment and soon was standing in front of her door, ringing the bell.

I saw her looking through the spyhole before opening the door.

“Hello love, come on in!” she said as she appeared in the open door.

Wow, I thought!

She looked stunning. The only thing she was wearing was a purple thong, exposing her long firm legs beautifully.

Her big breast were pointing at me freely and her long brown, shiny hair was tucked into a bun, hugging her pretty face. Her eyelashes seemed huge with the mascara on them and her full lips were covered in thick, deep red lipstick.

I went inside, barely able to take my eyes off that hot 48-year-old milf.

As she closed the door, she went into the kitchen, poured a glass of white wine and guided me into the living room, my eyes on her firm big cheeks, that were hugged by her purple thong.

She indicated for me to sit in the armchair and as I did, she took her wine glass from the club table and we toasted our glasses. She left a red rim on the glass from her lipstick as she put her glass back on the club table, dropped to her knees in front of me and started to unbuckle my jeans.

“You’ve been a really good boy this morning in your office,” she whispered.

“Drilling my ass so hard for what the slut I am,” she grinned at me, my pants and boxers now at my ankles, my cock high up in the air in front of her face.

“Now you enjoy your wine and I’ll take care of you, honey,” she whispered in a sexy voice, giving me the sexiest look, I’ve ever seen.

She was looking deep into my eyes as her full, red lips wrapped gently around my cock, sending shivers through my whole body.

She sucked it off gently a few times until she panted:

“I love your cock, I love sucking it off, and I especially love when you drill that whore ass of mine like the slut I am,” she whispered and continued her sucking on my cock.

“Oh my god Ann, that feels amazing!” I panted, watching her sliding her lips over my shaft as she sucked it in almost completely, her ass sticking out into the air away from me.

She kept going and soon was deepthroating my entire length, giving me sloppy blowjob:

“Urgh, urgh, urgh, urgh, urgh,” was all that came from her mouth around my cock.

My cock was a mess of saliva and red lipstick and so was her face, red color spread all over her mouth, saliva coating her chin.

“Oh my god, Ann, I’m close,” I panted as she continued to blow me deep.

A few seconds later tough, she withdrew from my cock and was now swirling her tongue around the tip of my cock.

My dick started to throb and soon I was spurting my cum into her open mouth, covering also her chin and breasts with my long spurts, making an even bigger mess on Ann.

Ann then cleaned up my cock and swallowed the sperm that was in her mouth, rubbing in my cum on her breasts and smiled.

“I hope that’s ok for now, let’s have a drink!” she cheerfully said, getting her glass and sitting down across from me in the other armchair.

We took a sip from our glasses, Ann making a big mess of cum, saliva and lipstick on hers, and then chatted for a while casually.

Suddenly, she stood up, came close to me and turned around, exposing her firm butt to me, leaning forward so her ass came closer to my crotch area.

“Daren, do you like my butt?” she seriously asked.

“Ann, you have the most gorgeous ass I’ve ever seen! I’m crazy about it!” I honestly replied, touching her firm cheeks as she grinded on my lap.

“Then let me take some more care of you with my ass,” she panted.

She lifted herself up a bit, put her thong to the side and slowly but firmly lowered herself on my hard dick until her cheeks rested on my lap, my cock fully buried in her ass.

“Uhhhh!” she grunted.

Then, she started to very slowly ride up and down my dick, withdrawing herself only a few inches and then back in again fully, while clenching her ass, massaging my shaft.

Oh my god, this was too sexy, I thought.

This beautiful woman, painfully slowly fucking her ass backwards on my cock, massaging it with her ass muscles was driving me crazy.

“Do you like that, honey?” she grinned over her shoulder, visibly enjoying it herself.

“Ann, uhhh fuck, you’re driving me nuts like that!” I hissed, caressing her ass cheeks with my hands while she impaled her ass on my shaft, still painfully slowly.

“Good,” she smirked, continuing her teasing.

She did that for another five minutes, my head almost exploding at the slow sensations. As I tried to grab her waist to pace the fucking, she hissed:

“No, not today, put your hands on the armchair rests and just enjoy!” she instructed.

I did and taking my wine glass I took a sip, trying to distract myself from the sensations, while she continued to gently bob her ass up and down on my shaft, sliding out only a few inches and the lowering her back on it fully.

“Where’s your cock, Daren?” she teased.

“Oh my god, it’s in your ass, Ann!” I panted.

“How does your cock feel in my ass?” she continued, not stopping her slow motions.

“Oh fuck, it’s, just, oh my fucking god, it’s sensational!” I hissed.

She continued in the same pace, now clenching her muscles harder.

“Oh my god, Ann, I can’t do that any longer…” I panted breathlessly.

“Go on, fill my slutty milf ass with your cum!” she cheered.

Finally, she lowered herself down on my shaft and remained in that position, only clenching her ass, milking my cock.

“Oh god, fuck, I’m coming, oh god, oh god, ohhh ffffuuuuuuuucccckkkkk!” I threw my had back on the armchair as my cock spasmed and was shooting spurt after spurt deep into her asshole.

“Oh my god, Ann, that was just, I don’t know what to say,” I hissed breathlessly.

“Did you just cum in my slutty ass?” she teased further, still clenching her ass around my cock.

“Oh fuck, oh fuck, yes, my god, Ann, this is crazy!” I shouted.

She smirked back at me and again started to pull out a few inches before lowering her perfect ass back on my cock completely, still same agonizing slow pace.

“Am I your little anal whore milf, Daren?” she asked.

“Ann, you can be whatever you want if you continue this…” I panted, my cock being slowly fucked again by her ass, my cum still sealed in her anal hole.

“I’m a dirty ass whore, I’m your dirty ass whore, Daren,” she panted and continued my torture.

I looked down at her ass and mesmerized, following her motions, her puckered ring being stretched by my dick, appearing and disappearing from her tight hole.

“Oh my, that feels so good! I could to that for hours,” she grinned.

“Please do, or don’t, I’m going to have a heart attack, Ann” I panted again.

“I can’t have that love, I need you to fuck my ass hard regularly,” she smirked.

“Can I touch your perfect ass, Ann?” I begged breathlessly.

She rested on my lap, her muscles tormenting my cock in her ass and said:

“You can, but I’m dictating the pace, dear!” she agreed, and I placed my hands on her perfect firm cheeks, massaging them harshly as she picked up her slow pace again.

“Oh, my fucking god, you’re draining me, Ann, I’m about to cum again already!” I moaned.

“Go on love, I love your spunk in my slut ass!” she moaned.

My hands gripped her waist and pulled her deep into my lap as I started to shoot another load deep into that hot woman’s ass.

But she didn’t intend to stop right there, instead, her back again was bobbing up and down my shaft only a few inches each thrust.

“I can’t, I can’t anymore, Ann, this is surreal!” I begged.

“Imagine me on all fours on the floor, my ass spread for you…” again teasing me while moving her ass up and down on my throbbing cock.

“My hair in your fist, you squatting over me…” she continued.

“My skirt high up my waist, my slutty panties at my knees, begging you…” she further teased.

“Begging you to drill my whore ass hard, Daren, begging you to hammer your big dick deep into my ass…” she whispered.

Oh my god, this woman was nuts, I thought while she kept on riding my dick slowly in and out of her ass.

“Do you like that, Daren, do you like plowing me hard up my butt, Daren?” she panted, now breathing quicker herself.

“Yes, oh my god, I’d fucking drill your whore ass!” I panted, stars appearing in my head.

“Yes, because you know I need it hard, hard ass fucking, deep and fast, taking me, drilling me, plowing my slut milf ass good with your hard dick!” she whispered.

“Giving it to me hard like the anal slut I am!” she panted now.

“Oh my god Ann, I’m, I’m, oh my fucking god!” I screamed as my body started to shake, stars dancing around my head as I shot what was left in my balls in that hot milf’s ass, passing out on the armchair immediately.

As I regained consciousness again, I opened my eyes slowly, only to find Ann’s mouth impaled on my cock, her lips touching the base of it, deeply looking into my eyes.

“Mhhhhmpf, mhhhmpf, mhhhmpf,” it sounded as she was deepthroating my cock.

Finally, she withdrew her mouth from my cock, cleaning up all the cum from it and swallowing it in one go.

As she got up and turned around, I noticed a plug sitting in her ass, the diamond at the end having the same color as her purple thong.

She leaned down to me and gave me a deep kiss:

“I hope that was ok for you, love?” asking me with a devilish grin.

I only nodded, completely exhausted from the earlier sensations.

“Good, tomorrow morning, 7 A.M in the garage, be on time, and be prepared to take me hard!” she whispered.

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