New Roomie Pt. 17

Story Info
Linda's first anal orgasm.
3.2k words
4.5
7.5k
6
0

Part 17 of the 21 part series

Updated 06/09/2023
Created 01/15/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is a multi-part story of how my girlfriend's friend (Rachel) turns out to be 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 if you've enjoyed it and whether I should continue.

---------------------------------

An hour has passed after the hot scene in my office with Ann and Linda and I was looking at her at her desk from time to time.

She disappeared to the toilet a few times, coming back with reddened cheeks but still blushing, looking somewhat desperate.

Moments later, I saw her standing in the door of my office, still blushing.

She looked beautiful, I thought.

Wearing black high heels and skin coloured tights which made her legs look even longer and even more beautiful, her dark blue pencil skirt hugging her hips and flat tummy.

A white shirt complemented her outfit, unbuttoned to a slutty low point, exposing white skin on her cleavage. Her freckled face showed blushing red cheeks on the white skin, her big brown eyes highlighted by black mascara. Her long red hair was pulled together in a bun, making her look like the classy secretary.

"How can I help you Linda?" I asked.

"Ehm, I wanted to ask, after before, if you could maybe, help me, I don't know, it's stupid," she shyly answered and was almost on her way back to her desk.

"Help you how Linda?" I asked, making her stop in her turn, exposing her tight perfect ass in that skirt to me.

Wow, what an ass, I thought.

"Ehm, after what happened, I was very aroused and went to the bathroom to..." she stuttered embarrassed.

"To relief yourself?" I asked

"Yes" she admitted.

"But, even after, I, I'm still so aroused and don't know, what, how..." again stuttering.

"How did you get yourself off, Linda?" I asked seriously.

She blushed on that question and looked away, but her eyes found mine soon after.

"I, I rubbed my pussy with the plug inside my ass," she whispered.

"Have you ever had an anal only orgasm, Linda..." I asked again serious.

"No, I didn't know that was possible before I saw, Ms. Summers...".

Suddenly, I had an idea.

"Give me your panties Linda!" I instructed her.

She blushed again, looked back at the open door and was about to go and close it when I objected:

"Leave the door open Linda,".

She turned back to me and slowly started to pull up her skirt, leaving it at her upper thighs still covering her sex.

Then, slowly, she reached under her skirt with both hands and started to pull down her thong.

What came to my sight was a sheer red thong, very tiny, as she dropped it to the floor, adjusting back her skirt.

She bent down and picked them up, walking towards me until she reached my side and shyly handed me her panties.

I took them and pressed them on my face, deeply inhaling her scent looking straight into her beautiful eyes as she blushed embarrassed on my action.

"You're a very sexy girl Linda," I complemented while still sniffing on her panties.

She blushed even more at my comment, nervously patting around on her skirt.

"Do you have a boyfriend Linda?" I asked.

"No, I don't" she replied.

"But you did have sex, didn't you?"

"Yes, I did, with my previous boyfriends..." she shyly answered.

"So how do you pleasure yourself when at home?"

She again blushed at my direct question.

"I, I touch my pussy and sometimes use a dildo, but since a few day's I, the plug..."

"What about the plug, Linda?" I teased.

"I, I started to use it at home when I did these things and I, I think I like it a lot..".

I stood up and came close to Linda, giving her a kiss on her lips.

"Let's do a little experiment," I suggested.

She blushed and looked a bit nervous, not knowing what I was about to do.

"Get on my desk and kneel facing the door" I instructed.

She didn't hesitate, climbed onto my desk, knelt down and was looking at the open office door, sticking her ass out to me, covered by her skinny skirt.

Wow, what a view, I thought.

I slowly started to pull up her skirt over her hips, exposing her bare ass to me, her plug sparkling at me where her asshole was.

Touching her inner thighs and ass cheeks with my hands, she inhaled sharply at the sensations.

I sat back in my office chair, my face now on level with her exposed ass and lowered my face into her backside, exhaling my warm breath on her bare, dripping pussy.

With my one hand, I ran a finger slightly over her wet slit, causing her to pant and then, spread her cheeks with both my hands and licked over her needy pussy, very softly.

"Uhhhh!" she released a quiet moan.

I started to lick more, swirling my tongue around her clit, now and then sticking my tongue inside her wet pussy, her plug touching my nose.

She got more relaxed and eager and started to bounce her perfect ass more and more.

"Uhh, uhh, ohhh," she continued to pant.

I licked harder, giving my full tongue to her pussy, gently biting her now and then and then again, fucking her pussy with my tongue.

This must have made her close to an orgasm as her back tensed a few times, visibly swallowing her plug deeper inside her asshole.

"Oh my, I'm close, ahh, ahh, uhh, ohhh" she moaned now louder.

Relentlessly, I was now licking up and down her pussy, touching her clit hard before licking her lips deeply, finally giving her one little fuck in her pussy and then continued this circle.

"Oh my god, I'm cumming, I'm cumming, oooooohhhhhhh!" she released a squeak, breathing heavily.

As she regained herself after her orgasm, my hands started to caress her ass, massaging the two perfect peaches with my hands, occasionally running over her plug, pressing it gently further inside.

Soon, she became horny again, pushing her ass into my hands.

I reached under her upper body and pressed her breasts with my hands, then running them along her sides back to her ass, causing her to shiver.

Finally, I took the plug with my fingers and started to pull, gently but firm.

"Ahhh," she let out another moan as her tight sphincter was stretched.

"Oh my, that feels so good!" she moaned.

As the plug popped out of her ass, she let out a small shriek but soon another moan followed. I placed the plug in front of her face on the desk.

"Now, has anyone ever licked your tiny little ass, Linda?" I asked erotically.

She tensed a bit from my words, then relaxed back and answered:

"No, never,".

My hands again spreading her ass cheeks, exposing her perfect little asshole, gaping slightly from the large plug.

Slowly, my tongue found its way to her anus, covering it fully but only resting on it with no movements.

She breathed in sharply at the new feeling.

"Relax Linda, just enjoy yourself." I calmly whispered.

Her ass relaxed, exposing the tiny hole even more.

I started to slowly use my tongue to slightly lick around her tiny hole, feeling the puckered outsides on my tongue as I was circling around her most intimate hole.

"Ohhh, my god..." she released a moan.

I continued to circle around her anus, her starting to move her ass as well. Then, gently, I stuck my tongue a tiny bit in her asshole which made her pant, exhaling deeply.

"Ahhh, wow, my god, it feels, it feels, amazing!" she whispered.

I continued to lick around her anus in a full circle, then pushing my tongue inside it with a few strokes.

This continued a few rounds until I noticed her hand reaching down to her pussy.

"No Linda, not this time, focus on your asshole!" I told her.

She retracted her hand and was now putting her face on the desk, her hands beside her head, ass high up in the air completely exposed to my view.

Now, my tongue started to push in deeper and deeper in her ass, fucking her with long strokes.

"Uh, uh, uh, ah, ahh, ahh, oh my, gooooooddddd," she let out a deep moan from within.

I was now licking, fucking away in a good pace, her sticking her butt more and more on my face.

I glimpsed on her tilted face on the desk from behind and saw that her eyes were fully closed, deep arousal showing on her face.

I continued my tongue fucking and every now and then stopped it to lick the puckered ring in circles again.

"Oh my god, Oh my god, I think, I think, ahhh, uuuuuhhhh" she panted deeply.

Finally, I picked up the pace, plunging my tongue deep inside her ass with each thrust.

"Ahhhh, I'm comming, ffffuuuuuuucckkkkkkk, ooohhhh my ggggooooooooooodddddd" she almost screamed into the office, her anus pressing harshly on my tongue.

I stood up, looking at this beautiful girl, her ass glistening with my saliva, her upper body hardly breathing, eyes still closed.

At last, she opened her eyes and whispered:

"Oh my god, I just came from this, and, I've never in my life had such a strong orgasm!" her ass still sticking up in the air.

I smiled at my job good done.

Linda got down from the desk, took her plug and pushed it back inside her ass.

Then, as she reached for her red thong, I stopped her:

"No, they are mine now!" devilishly grinning at her.

She blushed and started to adjust her skirt and shirt again, leaned down to me sitting on my chair and gave me a kiss.

Then, her lips started to circle around mines, licking my lips that just been licking her ass.

"Thank you so much Mr. Davies" deeply looking in my eyes.

At that moment, my desk phone rang and I had to take the call, looking after Linda who was now walking back to her desk, wiggling her ass more than she used to before.

After the call, I walked out to Linda's desk and asked her whether she had plans for this night or is she was up to have a few drinks down at the bar.

She agreed happily and I left the building quickly, walking straight into the sex shop around the corner.

I bought a black, mid-sized suction cup dildo, similar to the one that Rachel had and went back to my office, hiding it in a plastic bag so Linda wouldn't see.

As it was pushing six o'clock, I grabbed my stuff including the bag and Linda and I headed for the bar.

We ordered some drinks and were casually talking with each other until I asked:

"So, Linda, do you want me fuck your ass at some point?" I asked carefully.

But she didn't blush anymore, her eyes sparkling a bit at my question.

"Yes, yes, I want that, but, I'm not sure I'm ready yet..." she shyly responded.

"I know, that's why I have a gift for you," I smiled, taking the plastic bag from under the table.

I gave it to her and told her to look inside. As she did, her face showed a mixture of arousal and fear.

"Tonight, when you're at your place, I want you to put that on the head board of your bed. Then, in doggy position, I want you to carefully and slowly try and get it in as much as possible, using a lot of lube." I explained.

She looked shocked first but then nodded:

"Oh, okay".

"One more thing. I want you to film your face as you do it and then send me the video on my phone," I instructed further.

Her frightened look now turned into a horny one and she sheepishly said:

"I like that, it's so naughty!" giving me a smirk.

We finished our drinks, Linda visibly pacing herself, trying to get home as quick as possible.

I smiled on the inside, looking forward to what she had to show me.

We left the bar and parted for the day and I was on my way home.

In the garage, as I exited from my car, I saw Vanessa walking towards the entry to her building.

She was wearing jeans short, exposing her long beautiful legs and a peek of her butt.

A simple white top finished her summer wardrobe, exposing her firm breasts nicely through the fabric and her long blonde hair was tucked together at the back of her head into a bun.

My dick immediately got hard on this sight and I walked closer to her.

As she saw me, a big smile appeared on her face and as she came closer, she didn't say hi or anything but whispered:

"My boyfriend isn't home," with a devilish grin.

I grabbed her ass with my hand, giving it a few spanks and we made our way to her apartment.

Once in, she gave me a deep kiss.

Then as we parted, she turned around and walked to the couch, stepping on it on all fours, sticking her butt out to me while arching her back.

She looked back over her shoulder, grinning at me and said:

"You know what I need, don't you?".

I knew, and I needed that too. I haven't seen her in a few days and her sexy appearance alone just made me crazy.

I got closer to her, putting both my hands on her jeans shorts covered ass and fumbled around for a while.

She unbuttoned the shorts and I slowly started to pull them down over her ass, only to realize she didn't wear panties.

"You naughty girl!" I teased.

Pulling them further down, her plug appeared to my sight and I was really surprised.

It wasn't the original plug I gave her, it was one that I haven't seen before.

It had a black diamond at the end, but the white imprints were what really caught my eye.

It said: "Your anal whore" on it.

"Is that true, Vanessa?" I asked teasingly.

"Most definitely!" she replied with a grin.

I started to pull on it and she immediately let out moans of desperation.

As it popped out, I put it next to her, unbuttoned my trousers and soon after my cock was buried in her beautiful tight ass.

"Uhhhhhhhhhhhhhh" she let out a long growl.

"I needed that so bad!" she hissed.

I grabbed her hips and soon enough, I was plowing away her ass, giving her the full length with each thrust.

"Oh my god, yes, fuck, fuck, oh, oh, ah, fuck, yes, yes, yes" she was rhythmically moaning.

As I was thrusting away, I peeked over to my apartment and to my surprise, I found Michelle on all fours on my couch, thrusting herself back at Rachel who was behind her, fucking her friends ass with the strap on.

"Look at those ass whores over there" I said to Vanessa.

In her relentless butt fucking, she glimpsed over and hissed:

"Uh, what, ahhh, what whores, ffuck, fuck fuck, yes!" as I continued my ass fucking workout.

"Look here, you'll get a better view!" I said, giving her my phone which now showed the video show from my living room.

"Oh my god, you're filming this! Uh, fuck, yes, fuck me, fuck your anal whore!" she cheered.

She put the phone back next to her, concentration on her ass being fucked hard.

"Uh, uh, uh, uh, uh, uh, uh" she was now throwing her ass back on my cock.

Then, my phone beeped, a new message incoming.

While still plowing Vanessa's ass, I picked it up and opened the message. It was a video from Linda. I smiled as I opened it.

On my phone screen appeared Linda's bed with her on all fours on it, facing the camera.

Her tits were hanging down a bit, showing how firm they were, her nipples hard. Her face was showing a mix of horniness and struggle, trying to push her back on the dildo, moving her body slowly back and forth.

Good girl, I thought.

I changed to the camera app, put it in video mode and gave it to Vanessa.

"Film yourself while I fuck your whore ass good!" I commanded, still thrusting in and out of her ass in steady motion.

She grabbed it, pressed the recording button and was filming her face which showed deep sexual need, her body moving backwards and forwards as my upper body appeared behind her, my hands on her hips thrusting hard.

"Now, reply to Linda's message with that video and add: If you train well enough, you will soon be able to handle this too!" I instructed.

"Okay, oh, fuck, fuck, oh my god, fuck me, fuck me" she released as she was typing the message, finally pressing send.

"Oh my god, that's so hot, fuck me, yes, I'm close, please fuck me, harder, yes, yes, yes oh my god, oh my god, oh my fucking ggoooooooooddd" she finally screamed, having a leg shaking orgasm on my cock as I emptied my balls deep in her bowels.

As I was about to plug he reward inside her ass, she stopped me:

"Please let me taste it, I need to taste your cum!" as she plunged her finger into her used asshole and scooped a good lug out of it and put it straight into her mouth.

She did that a few more times until almost all was gone, finally plugging her ass with the plug, reminding me the she was my anal whore.

As we got dressed again, I promised Vanessa to soon meet again and she cleaned the living room up as her boyfriend would soon come home.

Once I left and closed her door, Ann's door suddenly opened. She and her husband stepped out, dressed for a night out.

"Good evening" I innocently said.

Her husband grunted something similar while Ann was in a much better mood, dressed sexily, her lips covered by a shiny red lipstick.

"Good evening neighbour, I didn't know you knew our neighbours," she said with a smirk.

"Oh yes, I was just bringing over my house key. They promised they would take care of my plants while I'm on a business trip," I stuttered.

"Don't get your hopes up with that bloke," her husband muttered.

I cried inside myself and Ann too almost burst.

"Well, have a good evening, we're heading to Alfredo's for a dinner night, you know that place?" she asked, giving me a wink.

"Oh yes, I like it very much, I might get a Pizza later actually," I smirked at her.

We all left and I went back to my apartment.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

READ MORE OF THIS SERIES

Similar Stories

I Bet You'll Like It His roommate is sweet, cute and she's into butt stuff...in Anal
My Descent into Anal Slavery Ch. 01 A young woman has her pussy pierced and locked up.in Anal
Presenting...Anne's Ass A failed attempt at self-bondage leads to a predicament.in Anal
Caroline the Teenage Bum Slut Caroline at school, the doctor's, and home as anal slut.in Anal
Ass-ignation Two girls fulfill his anal fantasy.in Anal
More Stories