It was when I realised it was over a week since I'd first shaved and that Melissa had not seen me in my new state that I twigged that she and I were really over. We were still friendly, but nothing more.
I think that if Melissa had been around I wouldn't have felt so comfortable flirting with the idea of sex with a guy. I certainly wouldn't have let Darren suck my cock and I suspect that I would have had the courage to draw the line with Tom and end up being thrown out. As it was, there seemed to be no reason to draw a line, after all I was a free agent and could leave at any time.
Next time Tom was in the office I got called in to do a preview, this time it was a gay video and Tom was naked, the first time I'd seen him completely so. In fact, he didn't have a bad body. I stripped off expecting the usual routine, but he called me over to him saying it was time to look at 'that smooth arse of yours'. I bent over and his hands explored my arse, pulling my crack apart and probing my hole with his fingers. He started applying lube and I realised what was going to happen, I was going to get fucked. I could have stopped but I was, I must admit, curious.
First I got 1 finger and then 2 up my arse, finally Tom's cock head starting pressing against my hole. I tried to relax but it was difficult and frankly, it hurt. Tom seemed to be rather more sensitive to my first time needs than I'd have expected. Though his cock was alarmingly thick, and stretched my hole intensely, it wasn't that long. Once in he paused and allowed me to recover before he started pounding my arse, and pound it he did. By the end my arse was sore but I'd learned something new, I liked getting fucked. As I was picking up my clothes Tom asked my how it was, I told him that my arse was a bit sore but that it was OK. He grinned, saying he knew that I'd come through.
I turned to go into the outer office and realised that the door had remained open, both Darren and Tracy had been watching the whole time, they were smiling and Darren said welcome to the MD's department. I realised that I'd finally passed my probation. Tom told me to clean myself up and take the rest of the afternoon off. I first of all sat down to recover, still naked I was oblivious to the gunk from my arse that I was transferring to the chair, I'd clean it up later. Darren informed me that my performance was awesome, both he and Tracy had doubted that I'd take all of Tom's cock first time.
I went home and took a long bath, soaking my sore arse but reflecting that I was looking forward to the next few weeks. I wanted to phone Melissa, but she was out, so I went out to act on some of Darren's advice. I went to a local sex shop and bought a couple of dildos and some lube. It was a couple of days before I dare try it. But once I had I couldn't stop, giving my arse a good work out each evening.
Life at the office became a little more relaxed as I now knew, more or less, what to expect and both Darren and Tracey became a little more open with me. On the days when Tom was in he fucked at least one of us and there were frequent 'business' meetings at which we were the entertainment. I began to realise that I had been selected for the job less because of my talents at work and more for my looks. Darren and I had a few sessions together where he gave me tips. We were both a little wary of anything like a relationship, but after comments from Tom about my poor technique when giving a blow job, Darren felt obliged to show me how it was done. In fact he, Tracy and I had a couple of hilarious teaching sessions whilst Tom was out of the office.
On the days when Tom wasn't there, a strong cameraderie developed between us. We would lunch together and exchange notes about our various experiences and the various 'business' contacts of Tom's. Some of these were profoundly dubious and we could not work out what reason he was entertaining them. One person who remained rather elusive was Toby Staines, Tom had a couple of out of office meetings with him, but he never came back to the office and we never had to entertain him.
When Tom announced that he had managed to arrange another lunch meeting with Toby Staines it was obvious that he was pleased and felt the meeting something of a coup. To my surprise, Tom asked me to accompany him and Toby to lunch, it was usual for us advisors (as Tom termed us) to join meetings for the post-lunch sessions. I later found out that Toby had expected one of Tom's staff to join them and Tom was too worried about the meeting to object.
Lunch was relatively straightforward, though I was rather nervous. We talked strictly business and Toby was totally charming, including me in the discussions when Tom tended to ignore me. Quite a lot of alcohol was drunk, though I tried to keep myself relatively sober. In the car back, I was sandwiched between Toby and Tom, I became conscious of Toby's hand on my leg as soon as we sat down. He winked at me as his hand moved up my legs and started to explore my hard cock, at first through the fabric of my trousers and then, to my amazement, he undid my trousers and exposed my cock and balls. I was conscious of Tom next to me, the driver in front and anyone looking in through the car windows, but I didn't care and found it rather exciting. I lifted up my arse and allowed Tom to pull my trousers down, revealing my cock and balls fully. With one hand he caressed my cock and with the other he explored my crack. By the end of the car journey he'd managed to slip one of his fingers all the way up my hole, exploring my chute deeply.
When the car stopped I pulled up my trousers and fastened them, though I had briefly considered leaving my cock exposed. Tom and Toby went straight into Tom's office, using Tom's private entrance, I went into the outer office. I stripped off and walked into Tom's office, my cock still rock hard; Darren winked at me and gave me a thumbs up.
Tom had put some porn on the DVD, some gay porn that I did not recognise, I was not even sure that it was ours. Tom was still dressed but had his cock out, Tom had just finished stripping off and was naked. He had a good body, smooth, hard and pale, he was hairless apart from a small, trimmed patch of blond pubes above his hard cock. His cock was huge, longer than mine and almost as thick as Tom's, and Toby obviously liked showing it off. His chest was smooth, and when he lifted up his arms to reveal hairless under arms, I realised that he shaved all his body hair, making me even more excited.
Toby was taller than me and easily lifted me up and placed me on Tom's desk, gently pushing me back and lifting my legs to give him better access to my crack. He squatted down and started tonguing my crack, pushing his tongue into my hole. I relaxed and allowed his tongue to penetrate, I could feel the bristles on his chin rubbing my crack. But he soon abandoned any preliminaries and thrust his cock into my waiting hole. Toby was firm and vigorous, thrusting his cock deep into me. It was only after Toby lay down so that I could sit on his cock, that Tom joined in and I sucked his cock whilst Toby penetrated me deeply.
In the end Toby fucked me twice and Tom once, so I think the session was a success from Tom's point of view. It was a success from mine as well, feeling Toby's huge cock inside me was a revelation. I was cleaned and dressed by the time Toby left, he came over to me and thanked me, which was a surprise, and discreetly slipped me something. Once everything had quietened down, I looked to see what it was. I assumed it was a tip, the idea of which I found alternately flattering and demeaning.
It wasn't money, thank goodness, but his business card printed with his business address and contact details. On the back was a message and his personal email address, he wanted to see me again and this time 'properly' whatever that meant. I thought about this a lot before doing anything. I didn't tell anyone about the card, not even Darren or Tracy.