I had a really bad week. Actually, bad would be an understatement, shitty would be more appropriate. Problems after problems had punctuated my Days. I managed to get a new job as an assistant executive at an accountant firm. For some reason, I was the only man working in this office, and since I was the new guy they were bullying me. I thought that I might just need to pass the week and it would stop.
I decided to change my mind by going to my favorite bar. It was a really popular one, it seems like the whole city was present in this multi floor boom box. Tall or short, fat, slim, ugly and pretty. I got in and already felt the stress leaving my body. I ordered some booze and hit the dance floor. Forgetting myself in the music.
After dancing for around 30 minutes, I decided to have a little rest. As I got to the bar, the barmaid gives me a drink and mentioned that some woman paid for it. I suddenly thought I was getting lucky tonight. Checking out the angels, I recognize my co-workers and my boss.
Is this a joke? They are nagging me even when I’m not at work!
Standing at 6ft and 2 inches, my boss is 1 inch taller than me. She has nice black long curly hair, matching eyes hidden behind a pair of glasses, curly hair, a pretty face, probably D chest, wide hips and long legs. I still haven’t seen her in heels, and she doesn’t have the model shape, but greatly still attractive to me. She definitely project confidence and success. Especially tonight with her makeup, her bright red lipstick, her sexy shirt and her ample leather skirt.
They get back on the dance floor and leave me alone. I relax watching them dance, surprisingly fantasizing over my boss. After a little while, they join me and we all chat a little. We hit the floor again and I surprise myself thinking that my co-workers are a great group. They slowly leave and the night ends with me following my boss to her car while she holds my hand.
We chat again while she drives, asking how I liked the job, the environment and my co-workers. I mention the bullying and she answers that they will probably stop after tonight. I find myself undressing her has we are talking. Finally arriving at her place, she tells me to get comfortable as she gets us some wine.
Chatting again, the alcohol pushes the subject to a dirty path, we play a truth or dare game and we suddenly start kissing.
What am I doing, why do I kiss my boss.
I get up, apologize and confuse myself. She grabs her shirt and pull at it undoing the pressure button, slowly, one after the other, making sure I get a nice view of her pink bra. This totally stuns me. She takes advantage of the situation, get up and press herself against me. My boss start caressing me and mention that she wants to take me.
Wait, MY BOSS just said she wanted to have sex with me!! Should I do this, why can’t I think straight? WHAT… IS… Happening?
She grabs my arm and take me to her bedroom. This room is nice, I feel relaxed as I walk in, there is a certain ambiance that says forget it. She presses herself against me again to kiss me. Her lips are soft and they taste like strawberry.
I feel like there is something against my blog. She steps back and pull at my shirt, breaking every buttons that were so precariously sewn. As I feel that the time slow down, I can see every button fly and a definitive look of lust on my boss.
She starts kissing my chest and nimble my ears, then she whispers something in my ear. I am not sure of what she said.
Blast it, it’s happening, I am getting lucky tonight.
I decide to kiss her and start being active in the situation. She is pretty and attractive, why can’t I have an active sex relation with my boss. It would be so cool if I could tell my friends that I am banging my boss in her office. I could totally sugar it. I reach behind her back and undo her pink bra. Her boobs are great. They are so big that they are pulled by the gravity.
I start reaching down and feel them. So soft. See start moaning as I cling on her nipples, I can feel her breathing getting faster. She gets on her knees and open up my jeans saying;
‘What do we have here.’
She pulls down my pants and caress my 8 inch boner trough my white tight and soft boxer.
‘I like these.’ She says. And this one is not bad either.
I can feel the wetness in my underwear as she reaches over the band and slowly pull them down. Grabing on my cock, she brings it to her lips and lick it, ever so slowly. My boss, then take my cock in her mouth and suck on it avidly before pulling it out and lick it some more. She takes my balls in my mouth and turl them with her tongue. She slowly licks the full length of my shaft, pause at the head and ask myself if I am ready.
I don’t have the time to answer before she takes it again in her mouth, and go all the way in. My boss has her nose pressed against my pelvis, with my whole penis in her mouth! I am so telling this.
She pulls herself back and keep sucking on my cock some more, putting her hands on my cheeks as she keep going up and down on my shaft. I can hear her moan as she clearly enjoys this. When I mention that I am about to come, she stops reluctantly and stand up, press herself against me. We kiss again. Her nipples are so hard that she is tickling mine. She whispers in my ear that it’s my turn.
I eagerly get on my knees thinking that I will give her the best oral sex she ever had, especially after this blowjob. I unzip her skirt with the zipper above her nice ass and her skirt fall on the floor. She is wearing a matching lace pink panty. The thing is that there is a big surprise in them. Her penis is nicely pushing out, asking to be set free. Things pulsing thing must be bigger than mine.
I back up as I realize what she is.
‘What’s up my dear. Don’t you want to do the same thing to me?’
As she reaches down and free this pretty cock from the lace prison.
‘ Well, I just never suck on a dick before.’
She tells me that she’ll guide me and give me some tricks.
Ok, I am a little into Shemale. I did check it out on the net, mostly because I was curious, then it started being a fantasy. Thing is I never felt ready to try this. I mean taking a dick in my mouth is something totally different that looking at some sexy women pushing it in some half shown men.
‘I would rather not have to use the I am your boss card honey. Please do it, it’s so hard to find someone that is not afraid of me and runs as he feels it.’
I ask her to be really nice in everything we do tonight as I do nothing of this before. After she swear to be gentle, I turn my attention back to this challenge that life as threw at me. I grab it, yup, she is definitely bigger than me, at least one more inch, if not two.
I slowly put my tongue on it. It’s so hard and solid. I feel like I could break my skull on it. I can feel her breathing and shiver as I slowly put the head in my mouth, so warm. I alternate between suck the head and licking the shaft, even giving some attention to the balls.
‘Man, you are good, this is one of the best blowjob I got. Oh yeah, take it deeper baby.’
As I try something she just told me to, I am rewarded by a moan. I think I am enjoying this! She brings her hand on my head and caress my hair as I keep sucking on her. I put my hands on her ass and try to get deeper, choking on this enormous meat. She gives me another trick and push a sexy loud moan.
Damn, I like this. I feel so much in control.
She push my head on her member with her hand. As I gag on this bone and try to pull out, I realize that she has the control, she is so strong and just keep pushing her dick deeper in my throat. Now it’s my turn to have my nose on her skin. Keeping me there a few seconds, she yells and let me take it out. As I am on my knees with my hands still on her cheek, breathing deeply, looking at this big thing I had all the way into my throat a moment ago, still from my saliva. I am thinking that I didn’t mind if she force me to take it all the way in and that I would let her do it again.
Putting a couple fingers under my chin and pulling me up, she kisses my wet lips and apologize for being rude. She just can’t control herself something and she has to dominate her mate. I kiss her back and tell her I kind of like it.
‘Well, my dear, it’s time for more domination. Lay on your back. I want to see your pretty face when you feel it getting really deep in you.’
I do as she ask and get on the bed. She lubes her big member while looking at me with a nice sensual expression. She also gently applies some on my muscle and in my ass. I can feel her fingers massaging my prostate a little, trying to get deeper, ever so deeply. Then come the moment of no return. She put her dick at the entry of my best kept secret and start pushing.
This thing is huge! Bigger than anything else. I had problems taking it in my mouth, forget it, it won’t fit in here!
‘Relax my dear. It will hurt more if you are so tense. This was just the tip. I will keep pushing slowly.’
As she says this, I can feel her getting further. I try to take her advice and relax. Otherwise, this pain will get worse.
‘Man you’re tight my dear. I can tell I am going to enjoy this.’
As she is finally completely in me, she lay on me and whisper gently in my ear.
‘How does it feel to have all this wood in you.’
As I open my mouth to answer, she kisses me. I just can’t get over the fact of her soft lips and her strength everywhere else. She is so sensual yet so powerful. She lay on top of me for some seconds, kissing my face, nibbling on my ears and kissing me some more. I feel like I relax, I can sense that I am loosening up. She asks me if I am ready. Since the pain have received I say yes. She pulls out, I am empty inside, push back in. This is great, a mix of slight pain and pleasure and there is more sensation coming from my prostate.
As She feed me with half of her member, ever so slowly, sensualy and terderly. Our breathing gets faster, we are definitely enjoying this, I am caressing her body as she is giving it to me. She alternate her positions slightly so that she doesn’t tire too quickly, while keeping a good pace.
This concert continues for a good time. I can feel her breathing even faster, I can tell she will come soon, as I feel something coming down my crotch. She whispers for me to masturbate for her, which I do, as she kept fucking my ass. It doesn’t take long before we both come. My sperm is propulsed to my chest and even my face, this is the biggest load I ever felt leaving my body, it feels great. As I am coming, I can feel hey cock pulsing in me and unloading herself, my muscles are contracting around her, giving both of us more sensations. She keeps coming when I feel my orgasm completed, but it doesn’t take her long.
My boss withdraws from me, her huge member leaves an empty feeling in me. She suggests that we have a shower before going to bed, which we do