Very Hot

Very hot

Weekend with the Boss

I’d just started at this new job a few months ago and my boss Lisa was so nice to me, we’d been play flirting for a while, she was really hot, a Megan Fox lookalike. Huge tits, great ass and legs to die for. I knew I couldn’t get with her because she was the boss but the flirting was getting a bit intense, until one day in her office we were joking about my ass. My ass was good, firm, peachy, I’d been working on it at the gym on leg day, and then my boss said ‘oh I’d love to peg that’ erm what.

This stayed in my mind for the rest of the week, the thought of my boss pegging me, surprisingly, it turned me on quite a lot. We had a works do at the weekend and I was looking forward to flirting with Lisa again, we were both single so it was fine in theory, I just didn’t know whether getting with the boss was a big no no or not.

I dressed up for the works party, my sexiest boxers, tight chequered grey trousers and a dark blue shirt that was probably too small but made my muscles look bigger than they were, 3 buttons undone because it wouldn’t button up all the way anymore. I got there and got a few drinks in, the workforce was mostly girls and so I was the centre of attention, being cheeky with them all and making them laugh.

‘You look great!’ Lisa said as she came over in a light blue satin dress that hugged her curves perfectly, ‘wow so do you Lisa!’. We flirted for a while and got drunker and drunker. Eventually she asked me to walk her home, when we got to hers she invited me in for a few drinks, I was way past caring whether this was appropriate with the boss.

As soon as Lisa shut the door behind her she kissed me, our bodies came together as we made out and moved towards the couch where she lay on top of me. Lisa got up and pulled my shirt off and my trousers down, I was obviously very hard already. Lisa smirked and beckoned me to her bedroom, she lit some candles so there was barely any lighting as I got on the bed.

Lisa straddled my chest in her sexy dress, this was it, I was going to eat her out so hard. ‘Your cocks nice, but I hope you’ve got an open mind’ Lisa told me, my cock was about 6 inches so I was happy with this comment. My cock sprang to attention as she pulled up her dress and where there should have been some panties, was a huge cock. Lisa was a shemale? I was so confused, she carried on pulling her dress off and then pushed her cock towards my face. ‘But it’s not a real cock like mine’ I was so turned on but in bewilderment at the same time, I didn’t know what to do, I wanted to get up, I wanted to - I wanted.. I wanted to suck her cock.

I opened my mouth as Lisa thrust her cock into my mouth, it tasted better than expected, I couldn’t fit all of it in but I moved my tongue around like the girls I’d shagged in the office did to mine, Lisa moaned to let me know I was doing a good job. Her cock grew and grew and grew, growing to about 9 inches, I knew what she meant, it was magnificent, my cock was nothing compared to this. Her cock was pulsing as she climbed off my chest, ‘take those boxers off and get on your hands and knees’

I did as I was told, loving how bossy she was, she poured lube into my ass and onto her cock, she put just the tip in ‘I’m just going to let your ass adjust to this size’ so far so good it felt great. She pulled it out to inspect and I moaned, Lisa giggled as she said ‘oh you already miss it, this is going to be fun’ she re-entered my ass, and then rammed her cock in balls deep. Lisa fucked me hard, my ass was in ecstasy, loving every inch of her cock, she carried on fucking me as hard as she could, her balls hitting my gooch and sending waves of pleasure up my dick, I was rock hard, my cock swinging with the motions,

I felt Lisa’s cock pulse and throb as she came in my ass, flooding it with cum. But she didn’t stop, she kept fucking me until we changed positions, me on my back watching her tits bounce as she fucked me, the night carried on like this until we fell asleep.

I woke up. I was the little spoon and Lisa’s cock was rock hard against my ass, now it was light it looked even bigger, monstrously huge. Her morning wood put mine to shame. I got up to go for a wee, climbing out of the pink silk bedsheets, her room looked amazing.

~clink~

I looked down. My glasses weren’t on but I could see something metal on my cock, I grabbed my glasses and saw a cage on my cock, with a lock on it. Lisa must have locked me in chastity last night, I frantically looked around for a key. Nowhere to be found. I went to the toilet, sitting down to pee. I came out of the bathroom and found Lisa stroking her cock. ‘Morning Bitch, what do you think of the cage?’ ‘I don’t remember this being put on last night’ ‘Well I thought since your cock is nowhere near as big as mine that I’d lock it up, we won’t be using it anytime soon’ ‘But what if I want to masturbate?’ ‘Well that won’t be happening, you can come to my office and get fucked by me’ my cock was straining in its cage, this sounded hot but very sudden, I was completely fucked, she owned me now and she knew it. ‘Get back in bed with me, it’s Saturday and neither of us have anywhere to be’ I got back in bed and she spooned me again, she reached around and fondled my cage, stroking it, squeezing my balls, rubbing the head, I was so aroused, she knew exactly what she was doing.

Then she started to put her cock in my ass, I arched back so she could put it in, I may as well learn to love this. She started to fuck me again, my cock bulging now, throbbing with frustration as I got more and more turned on. Her tits pressed against my back, her cock thrusting in and out of me, her hair tickling my back and neck as she nibbled my ear lobe ‘I have the keys to your cock, I own you now, you’re going to move in with me, then I can fuck you all the time’. After she came in my ass again, she told me to put on her lingerie, a black thong and bralette, as my boxers were nowhere to be found, put on my shirt and trousers and sent me home to get my stuff.

For the rest of the day I packed all my belongings, paid off my bills, sorted everything with my landlord and came back to Lisa’s, she unpacked all of my clothes and then gave me a box of all my underwear. ‘You’re going to throw all of these out and we’re going to go shopping for some lingerie, you need to dress like the slut you are’ my cock throbbed in response, rubbing against my thong and trying to get harder. Lisa grabbed my cage through my trousers and said ‘I’ve been looking forward to this ever since you started working for me, last night was amazing and that was only the beginning’ she pulled me closer and I felt her huge cock against me as she kissed me. This was going to be amazing.