Hooking Up with a Coworker Ch. 06 – Anal – Free Sex Story

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One Thursday last summer, Kat texted me and told me “My divorce finalized yesterday! Why don’t you to come over around 8 tonight. You’re staying the night.”

I texted back, “Congratulations and that sounds good ;-). Do I need to bring anything?”

She responded with, “Nope everything is good to go.”

Around 8, I got to Kat’s house, when I knocked on the door, she answered wearing a light pink silk robe and holding a glass of wine. I could tell that she wasn’t wearing much, if anything under the robe because I could see her nipples pushing through the fabric.

I hugged her and congratulated her again on the divorce finalizing. She smiled and said “Yes! That is a huge load off my shoulders. We talked for a few moments about how her kids were handling it as she finished her glass of wine.

As we relaxed, Kat began to slowly stoke my thigh, not wanting to rush her or anything I didn’t say anything, but my cock had other ideas.

As it began to harden, Kat noticed and said, “Why don’t we head to the bedroom?”

As we got to her bedroom, she turned around kissed me passionately, as we took a breath she said, “I’ve wanted to do this with you, but was afraid to be shot down, so be gentle.

I kissed her back and said, “What are you talking about Kat?” S

he smiled and said, “Good, I want you to fuck me in the Ass, just listen to me as we go. One rule though, the feeling will be very intense for both of us, but please don’t cum in my Ass, it sucks so bad afterwards, pull out and cum on my face or something like that.” I nodded and kissed her and untied her robe, dropping it to the floor.

As her robe hit the floor, Kat turned around and bent over showing me the matching pink jeweled plug that she had in her Ass.

I remarked, “Well that’s pretty.”

She giggled and said, “I started working it in over the past few days, but I have worn it all day today, I can’t wait to have it and your cock. Now take your clothes off!”

As Kat lay back on the bed and lightly stroked her Pussy, I stripped my clothes off hurriedly and then climbed on top of her.

As we kissed, her hand wandered down and began to lightly stroke my cock. She stopped kissing and instructed me to lie back. She climbed down between my legs and began to slowly suck my cock.

She worked my cock and balls for 3-4 minutes causing me to moan and groan as she went deeper on my cock until she had my entire cock in her mouth before she stopped and said, “I’m wet as hell, would you fuck me already!”

Seeing the dominant side of her was very different, I just shook my head. Kat stood up and lowered herself onto my cock.

Now I’ve fucked Kat more than 10 times at this point, but when my cock slipped into her this time, there was definite difference since she was wearing the plug. It was tighter, and almost firmer feeling.

Thankfully Kat was plenty wet, and I did just slide in after I felt the difference. Once Kat had slid in the entire way, we both just stayed still for a moment before Kat said, “Damn that feels amazing, you always fill me up, but this is something different.”

I just kind of moaned as she began to ride my cock. Kat really showed off her fitness because rather than grind against me like she does a lot of times, she actually bounced up and down on my cock for about a minute or two, moaning louder and then she drove herself back onto my cock fully and began to cum.

I have heard her moan during Orgasm many times, but this time it was something else, more primal.

As she collapsed against me, it took her a minute to regain her breath, as I kissed her neck and my hands wandered. Kat sat up with my hard cock still inside her and she goes, “Are you ready for this?”

I responded, “I am if you are.”

Kate sat up and eased herself off of my cock. She ran into the bathroom and came back about 30 seconds later. She sat beside me on the bed and said, “Okay, put this lube on your cock, a lot goes a long way, but make sure you coat everything good.”

As I did what she said, I noticed her putting some lube around her Ass. After I coated my cock, Kat reached over and stroked it a bit and goes, “Yep that was enough, go ahead and put more on.”

After I was done, Kat told me to get behind her like doggy style. Once I did, she said, “Go ahead and put the tip in, it’s going to be very tight, but I’ll tell you when to push more.”

I lined up behind her and put the tip of my cock on her asshole and slowly pushed; Kat was right it was very tight and at first it didn’t seem like it was going to work, but Kat took a deep breath and with a grunt, the tip of my cock slipped inside of her.

I could feel her Ass squeezing my cock and we just stayed still for a minute, and I asked her if she was okay.

Kat responded, “Yeah, it’s just been a while and it takes a bit to get used to.”

I nodded my head and Kat said, “Go ahead and slowly push more, I’ll tell you to slowdown or stop if I need you to.”

I slowly began to push further and further into her; when I was about 2/3 of the way in Kat said “Stop, I need to get used to this much before we go all the way.”

As we were taking a break, she asked me how it felt. I told her, “It is incredibly tight and it smoother than your Pussy, but it still feels great.”

She grinned and said, “Okay go ahead and push the rest of the way in.” I slowly shoved my cock the rest of the way in and as I got it all the way in, we both kind of grunted, then sighed.

We both stayed still for a moment, and then Kat turned and said, “Slowly pull your cock out, we need to put a little more lube on before you start fucking me.” As I slowly pulled my cock out, I couldn’t help but moan a bit as did Kat. Once I got my cock out, I noticed that it was completely clean.

Kat noticed me looking and laughed and said, “Don’t worry, you always make sure you went to the bathroom a few hours before so you’re good and cleaned out.”

I smiled and apologized for not knowing. She just laughed and said, “You’re fine, now get ready, I miss the full filling.”

I put more lube on my cock and Kat put a little more around her Ass. She asked me if I was ready and I shook my head yes.

As I lined back up, she goes, “It should go smoother this time, just go slow until you’re all the way in.”

As I slipped into her Ass, it was definitely easier and as I slid deeper into her Ass, Kat began to moan. Once I was all the way in, I paused and waited for guidance from Kat.

Kat turned her head and said, “Go slow as you thrust, and I’ll tell you when I want it faster.”

I began to slide in and out of Kat, causing us both to moan. I realized very quick that I couldn’t pull out as far and my thrusts were much shallower, but it still caused both of us to moan. After a minute of slow thrusts, Kat told me to speed up but not to go hard. I picked up the pace a good bit causing her to moan even more and more.

I noticed Kat was playing with her clit as I was fucking her Ass when suddenly she went rigid and began to cum. I slowed my pace a little bit but kept thrusting as she came.

With her Orgasm, I began to feel my Orgasm building, I told Kat, “I’m going to cum soon.” Remembering what she told me at the beginning, I slowly pulled my cock out of her.

After I pulled out, Kat rolled over onto her back and said, “Cum on my fucking face!” I moved up so I was straddling her, once again the shock of her being so dominant, caused me to get even more turned on and as she fingered herself, I felt myself begin Cumming and I shot 7-8 ropes of cum all over her face.

As the last rope of cum landed on her glasses (BTW, one of the hottest thing I’ve ever seen) she let out a moan as she began to cum again herself. As her Orgasm subsided, I laid down beside her on the bed and caught my breath.

We both laid on the bed and caught our breath, after a few minutes Kat asked while wiping her face with my shirt, “Well how was your first Anal?”

I leaned over and began to lightly finger her causing her to moan and replied, “It was definitely different, but I enjoyed it.” I quickened my pace and within another minute or 2, I felt her Pussy clamp down on my finger as she came again.

As she came down from her latest Orgasm, Kat said, “Why don’t we take a Shower and go to bed, I’m exhausted?” I agreed and off we went.

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