Now I look back on it, my boss Megan was into me from the moment I joined. I remember her being so kind on my first day, constantly popping back to my desk to make sure everything was okay. At one point, as she was helping me get set up on my computer, she leaned in really close, her hand resting for what seemed like ages on my thigh. But I put it down to her being a really tactile person. Some people just are.
Plus, I didn’t mind her getting up close and personal, as she was hot. I guessed she was around forty, which made her ten years my senior. She was a little taller than me at five foot eight, and with really sexy big breasts and an ass I just wanted to grab hold of. Her long black hair brushed against me as she leaned in and I could smell her scent up close. It wasn’t any fancy perfume, but a wonderful natural fragrance that made me think about what she’d look like naked.
Everyone in the office knew I was trans when I joined, so at first, I didn’t think this sexy middle-aged woman was coming onto me with her close attention. Over the course of the next month, we became quite close, mainly I think because I’m a damned good worker, and she knew she could rely on me really from Day One.
We’d often find ourselves alone in the office at the end of the working day, making sure there was no backlog to deal with in the morning after everyone else had buggered off home. At times like those we’d laugh and joke a bit, just the two of us, and once or twice we’d go for a glass of wine at the local bar. We talked about our lives a little then and I knew that she was married, but maybe not entirely happily.
There was definitely a twinkle in her beautiful dark eyes when we were alone together having fun. She knew I was single and, knowing I was trans, would tease me after a few glasses about whether it was the guys or the girls in the bar I’d like to take home and screw. Once when we were out together she point out an older woman, with a full, sexy body just like Megan’s, and asked me if I’d like to screw her.
We were definitely becoming friends as well as colleagues, and I was beginning to feel that Megan might be interested in being me as more than a friend, too. The truth was I would love to fuck Megan, but she was still my boss, and I didn’t want to misread her friendly banter and tell her that.
At the end of my three-month probation, Megan suggested we go out and celebrate. Her husband was away for the weekend, she said, so she’d be thankful for the company, and anyway, she wanted to thank me for being such a great worker since I joined. I said yeah, sure, that would be great. She booked a posh Italian restaurant for us on Saturday night, and I figured as it was a nice place I’d wear something nice, make it an occasion.
I put on a blue gown, quite long but with a slit at the side that went halfway up my thigh. In my high heels, I knew I looked hot, and I wanted to, for her. When I arrived I was knocked out by what Megan was wearing. She had a long dress on too, a red one, but bloody hell the plunge neck on it left nothing to the imagination. I spent the whole evening trying not to stare at all the gorgeous titty flesh that was on show. Sitting opposite her on the small table, I was doing my best to look into her deep dark eyes and not at the beautiful full cleavage that was on show for me.
She was flirting, little touches on my hand all the time, and at one point reaching over to stroke my arm as she told me how much she valued me as a colleague. It sent shivers down my spine, feeling her nails dragging over my skin so lightly, but still, I didn’t want to make a move that might be misjudged. My cock was throbbing and thick in my black satin panties, and by the end of the evening, all I could think about was whipping it out and pulling her full red lips onto me.
At the end of the meal, as she paid the bill, Megan asked if I fancied coming back to hers for a glass of wine. The night was young, she said and she really didn’t want to go back to that empty house by herself. I was more than happy to join her, and we jumped in a cab. As we got in beside one another, her fingers touched my bare thigh, resting there for too long for it to be inadvertent. I was sure I was reading the signals right but didn’t want to make a move in the back of a cab.
Back at her place she sat me down on the couch and went to get some wine. Pouring a couple of glasses, she said she was going to change as the dress was so tight, she touched her boobs as she said that, laughing and saying they needed their freedom. She headed off, leaving me on the couch with my erection starting to show through my dress.
When she came back, she was wearing a short satin robe. It clung to her body, showing every wonderful curve. Her breasts were freed from the tight bra she had been wearing and moved below the silky material as she walked. She bent over to pick up her wine and the front of her robe fell open, right in front of me. Her huge breasts hanging there for me to gaze at as she looked into my eyes smiling. I had no doubt now what her intentions were and felt no need to hide the shape of my thickening she-cock as it grew beneath my dress.
Taking a sip of wine, she put the glass back down and sat next to me on the couch, right up close. She leaned forward to kiss me as her hand reached across for my erection, tracing the outline of it through my dress, her fingernails teasing it expertly. I groaned into her mouth as her fingers pushed my dress up and grasped my big she-dick, squeezing it through my satin panties. I was pulling at my dress to get it off as she pulled my throbbing cock out and began licking hungrily at my knob, lapping up the pre-cum that was oozing out.
She licked slowly up and down my shaft as she pulled my panties over my thighs and off, giving her access to my balls which she ran her tongue around before taking one in her mouth and sucking. Her hand was wanking my cock slowly and I pulled at her robe, ripping it off her so I could get my hands on her sexy body. My fingers found her wet pussy and pushed in easily, she was so soaking wet. My other hand grabbed a bunch of her hair and pushed her head down on me, my cock doing deep in her mouth.
She didn’t need my hand holding her head there, she was so hungry for my cock and her head was bobbing up and down as she deepthroated me. She was such a good cocksucker, I was struggling to concentrate on her body, it felt so damned good. All those times I’d been wondering whether she wanted me, and here was my gorgeous boss sucking on my hard girl-dick. I spread her legs as she lay on the couch, rubbing hard at her clit as she sucked me.
Her pussy was a soppy mess, she must have been creaming her panties all evening thinking about blowing me. My fingers were covered in her juices, all slippery and they slid in and out of her, rubbing hard on that beautiful clit of hers. Within moments her body was shaking and I felt her warm cum juices flowing out all over my hand as I finger-fucked her. Her head stopped bobbing as she came, and I grabbed her hair again and thrust my hips up to keep my cock sliding in and out of her mouth.
As she recovered from her cum, I pulled her up onto my lap. I wanted my dick deep inside that sweet pussy and I wanted those tits I had been ogling all night in my face. She climbed up and straddled me, her pussy lips positioned just over my aching, throbbing cock. Then she sat down on me and we both let out a moan of pleasure as her gorgeous big ass cheeks slapped down on my thighs. Steadying herself with her hands on the back of the couch, she started to ride me as I took her breasts in my hands and started to lick on her thick hard nipples.
I couldn’t believe how hot this woman was for my she-dick. She was bouncing up and down on it and screaming so fucking loud I was sure the neighbors would be coming around complaining soon. I was having a job keeping my mouth on her titties as she rammed herself up and down on my shaft. I gave up eventually and just pulled and squeezed hard on her nipples. It was enough to send her over the edge, and again she was flooding my lap with her pussy fluids. Her body was all beautiful and flushed pink as she screamed her way through her orgasm.
She slumped down on top of me and we kissed, a long searching kiss with our tongues twisting around each other as she recovered. My dick was still rampant inside her and as her hips began to gyrate slowly as we kissed I knew this woman was going to fuck all night. She slipped off me, moving her body down and kissing her way over my breasts and down over my stomach until she reached my cock. It was literally awash with her sticky cum and she was greedily licking it all up, licking my balls and thighs, everywhere she could.
I told her to get on the couch, kneeling with her ass sticking out towards me as I got up and stood behind her. She spread her legs for me, her pussy lips pouting from the deep fucking she had just had. I thrust my face between her ass cheeks and licked at her ass and pussy before standing and sliding my long cock back inside her.
I grabbed her hips and began fucking her with deep, long strokes, slow at first but getting faster and harder. Her gorgeous big ass that I had wanted to grab from the moment I met her was all mine now. I slapped it as I fucked her, her screams muffled as her face was buried in the back of the couch. Over and over I fucked her tight pussy, feeling the cum welling up in my balls but not wanted this to ever stop, so doing my best to hold back.
Every now and then I would need to pull out and bury my face between her arse cheeks for a few moments, just to keep my explosion at bay. Then I was straight back in, my hands on her arse and my cock piling into her. She loved being fucked like this and in all honesty, I lost count of the cums she had. I didn’t stop or slow down when she came, just kept driving into her hungry hole.
Pulling her big butt cheeks apart, I spat down onto her tight asshole. It was already soaked in her pussy juice and wet from several tonguings I’d given it, but I wanted my dick deep inside her there too, so pushed my fingers in as I fucked her, stretching her, getting her ready. I told her to pull her cheeks apart for me so I could fuck her ass, and she did what I said straight away, with no complaint. Pressing the head of my big cock against her muscle, loosened by my fingers, I pushed forward. Her ass gave some resistance for a moment or two and then with a pop, I slipped in. She let out a huge long moan that told me she loved getting fucked in the ass.
I took it easy to start, easing myself further in with each stroke, but I noticed that she was pushing back, pushing her ass towards me, urging me inside her. So I grasped her hips again and pushed with more force, gasping as I felt her ass gripping my shaft like a vice as I went further. After a while, she had taken every centimeter of me, and I pulled out and started fucking her properly. On the third or fourth thrust, she came again, her hands grabbing at the cushions on the couch as I kept going, not breaking my rhythm. Soon my big she-cock was gliding in and out of that wet asshole with no problem.
I pulled out and sat on the couch again, telling her to ride me. She backed herself onto me, standing in front of the couch as she pulled her ass cheeks apart and pushed herself down. Her ass took me so easily and soon she was bouncing up and down on me as I slapped her hard on the ass, telling her what a dirty whore she was. I sat up and played with her titties, pulling hard on those nipples as I knew she liked now, and again she was flooding my lap with all her love juice.
I was so close to cumming now, and couldn’t pull out to stem the flow. She knew it I think from my moans and groans and the way I was thrusting up frantically into her. She jumped off and turned round, taking my she-dick in her mouth just as it exploded. She wrapped her lips around me, tasting her own ass on my shaft as my cock twitched, pumping so much cum into her mouth. She did her best to take it all, but my girl-jizz was running out of her mouth and down my shaft.
She swallowed what was in her mouth and then licked me all over to make sure she got every last drop. Wanking my cock slowly, she squeezed it tight until the last little bit of my cum seeped out of me, which she licked at with a huge grin on her face.
We made our way upstairs and fell into her bed together, kissing and stroking each other’s bodies until we fell asleep, our limbs entwined. At some time, in the middle of the night or early morning, I don’t know but it was still dark outside, I woke. I was lying behind Megan, my arm across her naked body. She smelled so good, a mix of her perfume and of our sex, and I was rock hard, my heat pressing into the small of her back.
I reached down and fingered her pussy. It was so wet still. She moaned in her sleep as I slipped two fingers inside. I shifted a little and pressed my knob against her pussy lips. I slipped in easily and she awoke with a gasp as she felt me filling her. My breasts were pushing into her back as I hugged her close, my hips thrusting slowly in the darkness, long deep strokes.
She was cumming again within minutes, as I pulled on her nipples, my balls slapping against her ass cheeks, but it took me ages to cum. Not before I had fucked my gorgeous boss in every way possible again. That night was the first night of the most incredible affair. I might tell you more about it sometime.