A Sticky "TAIL"with no "END" In Sight pt 2.

Post time6-02-2021, 10:05

A sticky "TAIL" with no "END" in sight. pt 2.

OK so I fucked my assistant Anita and intended to get a piece of her ass but she made it clear, at least initially, that it wasn't going to happen but I had other ideas.
I wasn't getting ass at home but plenty of everything else. I always wanted to fuck a pretty young black woman and my assistant Anita filled the bill. We have been fucking for a few weeks now and although I never cheated on any of my girlfriends before I found out that cheating sex is pretty damn hot. I figured that it wouldn't be this good if she knew about it and/or we had an "open" relationship. I would be one sided in that way because I wanted to fuck whoever I wanted but for her to be just mine exclusively, open for me and closed for her was my preference.
I have been working Anita up to it and I was now intent on having my cock in her ass. We usually had sex in the office and here we are again:

My legs were bent slightly and my entire body was limp, my muscles were almost to weak for me to remain erect and attain my posture, my cock seemed as solid as concrete and twice as heavy. With her hand tickling my sack and her lips wrapped around the base of my thick cock I felt I could pass out when she swallowed to squeeze my cock head in her throat,
"OHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH", as I shot a huge thick milky stream of semen straight into her stomach.
She pulled back and with her mouth open, my cock head resting on her furled tongue,
"OH YEAH, UH, UH, UH", as I ejaculated three more creamy spurts of warm cum onto her tongue which funneled down her throat while she pulled off of me, gave my head a suck then closed her mouth to swallow.
She opened back up to take me in and suck hard on my head and tease my frenulum with her tongue while her hand milked the last remnants of creamy goodness from my cock.
She kept sucking on me and much to my surprise I remained somewhat hard. She bobbed on my cock and due to her expert sucking I was once again at the peak.
With my load off some of my energy had returned, my legs straightened and my posture returned and the lust that was sated has now surged again. I put my hand on the back of her head and grabbed her long beautiful dark hair and pulled her onto me and I fucked her mouth.
She looked up at me with those soft brown eyes and when I looked into them they let me know she needed me to fuck more than her mouth now,
"UMPH, UMPH, UMPH", was all she could do and her eyes were now watered and pleading me to stop so with one last thrust down her throat I held there then pulled out and let go of her hair.
She fell down on all fours grunting and coughing while gasping for breath while I stood over her and after several seconds she looked up and straight at my tool, it appeared menacing as it loomed over her but the lust returned in her eyes while she looked at. I picked each foot up to get the pants off from around my ankles.

This was reminiscent of our prior encounter, her on the floor after sucking my cock and me with my pants around my ankles except this time she was already completely naked and I had eaten her delicious little snatch before she serviced me.
I helped her up,
"Bend over the desk", I said. It wasn't a request rather it was more like an order. The lustful look she had previously vanished and was replaced by apprehension.
She slowly turned her body but not her head, she kept eye contact with me as long as she could with the same worried look. I placed a hand on her upper back and and pushed to get her to bend over. She looked back at me this time with severe worry on her face and in her eyes.
"It'll be alright", I said.
She knew I had been wanting it, each time we fucked I would finger it and each time I ate her I would rim it but the time had come and now I wanted, hell I had to have my dick in her ass.
She turned around and assumed the position, legs spread, forearms on my desk. I walked up behind her and reached down to finger her cunt, it was still plenty wet and there was no way that I wasn't going to fuck her pussy first.
She had a wonderful hot little cunt and I thoroughly enjoyed fucking her, our times together have been hot, nasty, taboo and exhilarating. With her being my assistant, a different race and I was cheating on my girlfriend it just made it all so damn hot and now, like it or not, I was finally going to get me some ass.

I put a hand on the small of her back and with the other hand I guided my cock to her slit and worked it up and down then positioned at her hole and pushed into her cunt.
She relaxed a little as I entered her, my cock was forcing her cunt lips apart and they stretched to take my girth,
"OOOOO, BABYYYYYYYY", she moaned out.
She had raised herself off the desk a little now and was in a more prone position, I grasp my hands around her waist and and was now thrusting into her sweet pussy.
From my point of view the scene was awesome, she is bent over my desk with her plump ass stuck out and to look up her back at her very light brown skin with me pumping into her, not to mention what I was going to do to her next, just set me on fire.
Her cunt squeezed my shaft as I bottomed out inside of her,
She wiggled her cute ass as I made another descent into her snatch, I smacked her ass cheek. This made her shiver with delight and I smacked her other cheek to equal things out,
"MMMMMMM", she said in a low voice while she shivered again. She liked it a little rough and forced so as I pumped her I reached and grabbed her hair and pulled it, she loved having her hair pulled while I fucked her, and with a little turn of the head and a twist of pleasure and pain on her face I knew I was close to having her ready for the next step.
She began to bump back at me every time I thrust up into her, she was getting close and started panting,
I pulled her long hair a little harder now and smacked her ass, I was riding her HARD,
While I pumped her she looked back and with her lips together gave me an air kiss then her eyes rolled up and she leaned her head back,
"UHHH, UHHH, UHHH, I'M GONNA CUUUUUUMMMMMM", she yelled. I doubled my efforts and letting go of her hair I put my hands on each hip and dug my fingers in and pounded her, then with a high pitched,
"EEEEEEEEEEEEEEEEEE", she squealed and flooded my cock with warm slippery jizz drenching my balls and running down her legs. After her initial flood came an,
"AHHHHHH, OHHHH THAT FELT GOOOOOOD", she breathed out as I continued to fuck her dripping cunt. This whole time I have been pounding her pussy and with my intention on fucking her ass I realized I had completely neglected that hole the entire time.

I reached down beneath me and coated my fingers with her jizz that was still dripping off my balls and went back up then started to massage her anus.
With her being thoroughly stimulated and knowing what was coming she seemed to be a bit more relaxed as I worked her brownie hole and inserted a finger while I continued to punish her cunt.
I was almost shivering with anticipation by just the thought of having my dick in her asshole, I began to breath hard not only from the pounding I was giving her but finally having her ass and my cock was getting harder. It needed to be like steel for me to penetrate her and although her natural lube was going to help I brought some extra help along with me and it was sitting on the desk right within reach.
I pulled out of her soaked cunt and while I continued to finger her hole,
YOU GONNA FUCK ME IN THE ASS BABY", she asked as she looked back at me. The fear she had before was gone, lust replaced the look in her eyes,
"I WANNA GIVE IT TO YOU, I WANT YOU TO HAVE ALL OF ME", she said. He tone was as full of lust as her eyes were. I was going to fuck her sweet brown ass and bury my cock as deep in her as I could.
"ARE YOU READY HONEY", I asked her.
She nodded her head,
"UH HUH", she responded.
She braced herself by backing up a little, bending her knee's slightly and grabbing the edge of the desk with her hands. Her back was arched in and her head was back as I guided my meat between the cheeks of her luscious light brown ass and placed my head at her brownie hole.

I took in a breath and eased forward, my squishy head flattened out then began to pierce her puckered little hole and even though she instinctively tightened and moved away while slightly grunting I pushed and planted my head firmly inside of her,
"OH MY GOD BABY, IT'S SOOOO TIGHT" I moaned in pleasure.
With the initial assault complete I stopped pushing and placed a hand on her hip and the other over the top of her shoulder and pushed again. As her hole stretched open while I pushed into her she held her breath for a second then tightened her fingers over the edge of the desk,
"UGH, OH GOD YOUR SPLITTING ME APART, OHHHHHH", she said while grunting, panting and gritting her teeth. Getting in another inch or so of my cock I stopped and she relaxed a little. I rubbed the small of her back,
"Take it easy baby and just relax, try not to tighten up", I cooed to her softly.

I was practically begging since it had been quite some time since I had my dick in a woman's ass I wanted so bad for her to just let me have it.
I knew it wasn't easy hell, I had been through this with a few woman and once they are acclimated they love it but when it's the first time or they had prior bad experiences then it just enhances their fear.
I stood there with my cock lodged in her ass and thought back to times with former girlfriends that I broke in or were already broke in and with some lube and a little preparation I could fuck them in the ass as easy as I could their cunt.
This is something I haven't been able to do with my current girlfriend and although I tried forcing then begging she just wasn't going to let it happen.
It may sound bad but I felt I may have a little more control over my assistant, not by way of threatening her employment, rather by just being insistent and getting a feel of the possibility during our prior sessions and if all else failed then yes I intended to hold the job over her head to get me what I wanted.
I didn't have to resort to that though, she was a nasty and willing girl inside, she just needed to be comfortable that she could be who she really is inside and I let her feel that comfort.

"OK, GO AHEAD", she told me. I tightened my grip on her and pushed, easing in slowly I gained a couple inches more inside despite her tightening and attempts to pull away. I held firm and continued to force more pipe inside of her while she groaned and grunted in protest.
It felt so damn good and I was on the verge of loosing any control I had, the animal inside was starting to take over and the need to have my cock deep inside her without anymore haste had enveloped me.
"IT HURTS, OH MY GOD IT HURTS", she screamed out. I was past the point of caring anymore I just had to do this I thought. I was struggling with myself and just wanted to fuck her, why wouldn't she just relax and give it up.
"ANITA, CALM DOWN AND JUST RELAX.RELAX, IT WILL FEEL GOOD IF YOU RELAX !", I said in the best reassuring tone I could muster. It was more of an order than a request or advice.
My cock has a taper to it so while the head is large and has a wide flair to it then just past that is narrows then begins to widen and thicken in the middle then tapers back down again.
I was at the thickest part of my cock inside of her and this always had been the hardest part for my woman so I knew once we were past this point then things would get better, at least I hoped in this case as it didn't always work out this way, but I needed this BAD.

I stopped my assault yet again and let her breath and release the tension in her muscles.
I've had tough times breaking a woman in before but this was exceptional. She was young, slender and tight but she was oh so damn scrumptious with her fine light brown skin, pronounced firm ass and toned body.
Her asshole squeezing my cock felt so good and I wanted that feeling around the base of my cock and without anymore restraint I intended to have that feeling.
I primed her up by smacking her ass very hard, then when she shivered I smacked her other cheek and with a hand still firmly over her shoulder I pulled her to me while I pushed into her again and when she protested I smacked her ass hard and continued to force my cock inside of her.
Her hips were now against the front edge of the desk and now that she couldn't pull away from me I let go of her shoulder and grabbed her hair and pulled while I smacked her ass as I drove my dick deep into her and started pumping.
He anus was wringing my dick dry, literally, so I stopped smacking her ass and grabbed the bottle of lube and aimed it at her ass crack and squeezed a stream of lubricating oil over her hole and onto my dick.
This helped while I pumped in and out, it coated my shaft as I plunged to the bottom and slapped my balls against her cunt,
"OH BABY, I'M FUCKING YOUR SWEET ASS", I moaned. With things lubed up I smacked her ass a few more times and continued to drive deep into her butt.
"UH HUH, IT'S FEELING GOOD", she grunted.

The intensity of this whole thing and the tightness of her hole gripping my cock along with the cum boiling up from my balls had driven me into a frenzy, now I had both hands on her hips and I was fucking her ass hard,
I hammered her harder now and while she arched in her back even more she turned her head slightly,
"CUM BABY, CUUUUUUM", she said.
As much as I enjoyed pounding her tight ass I ached to relieve the pressure built up inside of me.
I shoved deep into her,
"UHHHHHHHHHH", I yelled as I felt a torrent of cum course through my cock and out of my peehole.
Still holding deep another gush exited as my cock convulsed,
"OHHHHHHHH", I breathed in relief as the pressure had eased inside my once bursting cock and with a few more grunts I squeezed out a few more spurts and,
"WHEWWWWWW", I let out as the incredible feeling and tingling in my body began to overwhelm me. Along with that came the feeling of some remorse, I felt a bad that I was a little rough and gruff with her while I initially assaulted her ass but sometimes that's how it needs to be, you handle deal with it on a case by case basis.
I pulled my cock out of her,
She pushed herself up and turned to me,
"AND IT WON'T BE THE LAST", she said with a grin, she looked down at my cock then back up at me then smiled as she went to her knee's and positioned herself in front of me.
"YOU ARE A NASTY GIRL AREN'T YOU", I said, it was a statement more than a question. She took my cock into her mouth and cleaned my head off then suddenly plunged down and took me in to her throat and held me there then pulled out then after giving my head a few more licks she was done.

As I started to get dressed I picked up my pants and my cell phone spilled out of the pocket and onto the floor, what I saw sent a bolt of terror through me.
On the screen it showed that not only did I inadvertently dial my girlfriend Tracy's cell phone, it also showed there was still a connection and the call duration has now been 28 minutes, and still counting !.
If I would have known at this point that our entire session had been heard from the time I initially dropped my pants and having her suck my dick right up through the time she cleaned me off after I fucked her in the ass then what I had just said would be benign next to all that.

As I looked down Anita saw me and looked down and her eyes went wide, she looked at me and I opened my eyes wide like to convey "oh shit", then I put my finger to my lips and did a quiet "shhhhh" and our eyes returned back to the floor and we looked at my phone.
We stood there totally silent and within a few seconds the screen showed "disconnected", Tracy had hung up.
Hell when your caught your caught so what could I do, talk my way out of it ?.
"OH HOLY SHIT", said Anita.
I had a feeling of calm come over me and although I couldn't justify anything I felt fine about it. I picked up my phone and brought her number back up and pushed the button to dial her while Anita looked at me in horror.
I rang until her voicemail picked up and began to play, I hung up before it beeped for me to leave a message.
"Voicemail", I said looking at Anita.

We finished dressing and as I thought about things I figured perhaps I better get home "just in case". This thing can really go bad very quick and I could imagine if the tables were turned I know the first reaction is shock then sadness followed quickly by anger.
"Anita, take the rest of the day off, I'm heading to my house", I said.
She looked at me with concern,
"Are things going to be alright between you and me", she ask.
"Oh hell yeah, don't worry about that", I said while I finished dressing then gathered my things and headed out the door,
"I'll see you tomorrow or if not then I will call you, OK", I told her as I headed out the door.
I wasn't sure what Tracy's situation was at work but was afraid she would claim there was an emergency then go home and..who knows what ?.

When I got to the house I was relieved that I didn't see her car there first. I went inside and began to survey the house as my eye was on what was her's as opposed to mine.
I was busy assessing the logistics of a sudden and severe break up as I looked around and ran through a few scenarios in my mind. I was home for the longest time and was surprised she didn't come home early.
I waited around and just about the usual time I heard her car in the driveway and a door shut.
I braced myself for confrontation as I heard the door knob jiggle and the door open as she walked in and I turned to face her. I expected to see wet eyes or at least her eyes red from crying and an angry look but I saw neither.
We just looked at each other for several seconds and she finally closed the door then dumped her purse on the chair next to her.
I was perplexed and a bit nervous, although I liked the calm I was afraid of an explosion, so I decided to speak.
"I don't know what you heard..", I started to say but she cut me off.
"I heard EVERYTHING !", she said.
I figured this was the point of boil over and explosion was imminent and I worried when she calmly walked towards me,
"You are just a little bit ahead of me, like always it seems", she said.

I narrowed my eyes and cocked my head trying to understand, I felt a little better but still remained cautious as my mind was a blur trying to determine her mood and what she said.
After talking for a little while she told me she intended to spice things up a bit and hoped to introduce someone into our relationship to pick up where her abilities and desires left off. WOW !, that was a load off my mind.
I told her what had been going on for the last few weeks between Anita and myself she was "alright" with that and although it wasn't who she had in mind she still wanted an active part, albeit with someone of her choice.
I wouldn't have believed it because she seemed to be a bit of a prude but she wanted a threesome !, perhaps I wasn't giving this relationship enough of a chance or perhaps she saw my discontent and wanted to preserve it and indulge in some things she only thought about.

Now things were heading in a direction I could appreciate and be on board with, I could have my cake and eat it to. If this would have happened before then I would likely not had sex with Anita but I am glad about the timing regarding all of this.
If she cheated on me but it was with another woman or she wanted to have an open relationship with a woman then I was down with that but if another man was going to be involved then I just couldn't deal with it, she assured me that wasn't the case.
She told me she invited her friend Elissa over for Friday night and she intended to broach the subject with me then.
Elissa was a good friend of her's at work and as they talked openly to one another she knew Elissa liked certain things and somehow there seemed to be mutual interest between them so to preserve our relationship she thought about Elissa and she approached her and is all for it.
Being that this was just Tuesday I had all week to wait for this and that was torture. I have seen Elissa and like any guy that see's a good looking woman we don't consider or even wonder anything other than what they would be like to fuck and she was no exception.

We actually spent at least a couple hours and it was late in the day anyhow so after dinner we talked some more. I certainly had a load off my mind but all the talk and anticipation caused me to carry another load, the one in my growing cock. I was turned on like hell now just waiting until Friday plus I could fuck Anita and it be alright as well.
There was tension in the air and it was sexual, I wanted Tracy more right now than I had in several weeks and she seemed to be as enthused as I was.
We showered together and after soaping my dick twice and rinsing it off she got on her knee's and took me into her mouth sucking me like she never had before. We were attracted to one another and this recent liberation helped spur something inside each of us.
The thought of Tracy being with another woman was so hot and if I got to be in the middle then what could be better.
We got out of the shower and after drying off went straight to bed. We talked while we hugged and kissed and felt each other.
I asked Tracy if her and Elissa have done anything, she said it had only progressed to the talking/curiosity stage between them but didn't deny that when she was a younger and in college she "experimented", hell no surprise there as it is almost cliched phrase.
She liked it but was still very shy and although she prefers men she often thought about living a little more of the "sweet life".
I was actually hoping her and Elissa had been involved, the thought of her licking or having her pussy licked was getting me hot.
We made hot passionate love that night like we hadn't in a long time, I think both of us were insatiable, we just couldn't get enough of each other.

When we woke the next morning we made passionate love again, I had a new found appreciation for Tracy now and she was excited to get to work and tell Elissa that I was on board with things.
Before I went out the door to head to the office Tracy looked at me,
I gave her a wink and a smile and she leered back at me. Hell she knew I wasn't going to be a "good boy", I had a taste of some sweet young brown sugar and I had no plans to give it up.
A few weeks ago I thought this relationship was about to end but things took a turn for the better now. No more "sticky tail" for Tracy and there was finally plenty of "end" in sight.

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