In the end, of course, I did email Toby though it took me a few days to pluck up the courage. I got a message back almost immediately, from his Blackberry of course. He said how much he'd enjoyed getting together with me. He'd like to see more of me, but this time properly and wondered if he could take me out on a real date, so that we could start again without Tom being there.
I read the message carefully a few times. At first I was unsure what he wanted, a paid escort, a fuck buddy or something more. Finally I decided he wanted a little more than a fuck buddy, but I wanted someone else's opinion. I phoned Melissa and luckily she was in. She seemed completely unsurprised that I was having relationships with guys, so unsurprised that I wondered whether she'd thought about this before – a subject that I'd like to explore later, a lot later. After many preliminaries and much hesitation on my part, I read Melissa the message from Toby. She was quite clear, go for it.
Toby arranged for his car to collect me from my flat on Wednesday evening the following week. I was very nervous, unable even to decide about whether I should wear underwear (I decided not to, after all he already I knew he didn't). We went to a restaurant I certainly wouldn't have afforded in the ordinary way. Being a Wednesday the restaurant was quiet and we were shown to a booth at the back where we weren't overlooked.
The meal was fabulous and Toby was charming. So much so that half way through I blurted out that this was the first time I'd been on a date with another man. He laughed and said he was flattered and hoped that there'd be more. He tactfully made it clear that he wanted to see me independent of Artemis and I made it clear that neither Tom nor anyone in the office knew that I was meeting him, which I seemed to like.
He was surprisingly easy to talk to and we found that we had quite a lot of interests in common, though I was very aware that he was way out of my league financially and not sure how any relationship would pan out. I was still unsure whether he was looking for a relationship or a fuck buddy but decided to go with the flow and see what happens.
Towards the end of the meal I could feel the pressure of his leg on mine and started to get hard. He asked me whether I was wearing underwear; I said no, Tom had insisted we not wear it to the office but that I'd found I enjoyed the feeling so had given up wearing it entirely. He asked how I felt about people noticing I wasn't wearing anything, particularly if I got hard and I told him that it didn't bother me that I liked being noticed. I didn't quite have courage to say that I liked being naked and fucking in public, that would come when I knew him better (if at all). I did feel able to ask him what he was wearing underneath and he said that he occasionally went commando under jeans but generally wore briefs under his suits though recently he'd tried going commando there as well. We moved on to the topic of shaving, I confirmed that I shaved my arse and balls; again Tom had suggested it but I found I liked the way it showed of my cock and made my hole more visible. He agreed and said that he shaved his whole body, though he wasn't very hairy in the first place.
His hand had moved to my cock and with his other hand he moved my hand to his own cock, except that he'd unzipped his trousers and his cock was standing out proudly. Luckily the table cloth covered everything though I glanced over at the waiter to see if he'd noticed anything. Toby laughed and shifted his hand so that he could undo my trousers, soon we were both sitting with our cocks out. The waiter came over to check on our drinks and I nearly had a heart attack. When he'd gone Toby looked over at me and asked me if I was coping, I nodded saying that I couldn't believe I was doing this. He asked me if I'd ever done it in a restaurant, I shook my head, he grinned again and said that I should meet his friend Ben who had fucked more waiters than he'd had hot dinners.
His hand on my dick started working harder and I realised that he was trying to make me cum, I did the same for him and we both came together, spurting cum all over our trousers and the table cloth, Toby didn't seem bothered and we both started to laugh uncontrollably. Toby signalled for the bill, when the waiter brought it over Toby stood up, still with his cock hanging out of his trousers; he zipped up whilst giving the waiter a good view of his semi-erect cock. The waiter's eyes opened wide but he didn't say anything. I followed suit and gave the waiter another eye-full before we went to the waiting car (Toby seemed to have a car and driver at his beck and call, as I said he was out of my league when it came to money).
Once in the car, and when we'd stopped laughing, Toby apologised and said that he'd promised himself that this would be a proper first date, with no messing about and no sex. I said that I'd enjoyed it and wouldn't have had it any different. I suddenly became very nervous, worried that this was where Toby said thanks very much and good bye. Instead he kissed me, properly and deeply. I was aware of the driver in the front of the car, ignoring us in a professional way, but couldn't help responding. It was the first time I'd ever been kissed by a man, and everything was different; his strength, power and the feeling of his stubble and moustache; my cock went instantly hard. I became aware that the car had stopped. Toby pulled away and I saw we were at my flat, Toby said that we'd have to finish this next week and would I come to dinner at his apartment on Tuesday. I agreed with alacrity.
I was unable to sleep, alternately elated and worried by the turn of events in my love life. One date with Toby had made me feel more alive than ever before, but I couldn't compete with him in terms of status or money and the discrepancy gnawed at me. But I'd had a good time and couldn't wait till next Tuesday.
Back at work it was difficult not to talk about the date to Darren and Tracy, I compromised by saying that I'd met a guy but keeping his details quiet. Both were fascinated by the idea that it was the first guy I'd dated and I found it helpful being able to talk about Toby and dating guys in general. The day afterwards Melissa rang me eager to find out details; she was cagey about her own love life and I suspected her eagerness hid a desire to keep me from learning whether she was seeing anyone herself. To my surprise, I found I didn't care.
Life went on at Artemis much as usual, that is Tom pounded my arse at least once and fucked someone each day he was in. There was another big 'business' meeting where Darren, Tracy and I were all called in to provide the entertainment. This time, most of the guys just watched as the 3 of us performed for them.
Toby was away on a business meeting, but he sent me an email from his Blackberry, just a daft message and a picture, of his erect cock sticking out from his business suit as he sat in a first class carriage in the Eurostar on the way to Paris. I couldn't send him a picture back, but I did email a message and said how much I had enjoyed our date.
Tuesday came round alarmingly quickly. Toby had arranged to send his car for me to take me to his apartment, where we were going to eat. Nothing had been said about me staying for the night, and I felt that it looked a little too eager if I turned up with an overnight bag. I'd thought long and hard about what to take as a present, I couldn't turn up empty handed. If Toby had been a girlfriend, then I would have taken flowers. In the end I did this, but went to a profoundly expensive shop who created a strikingly spray of flowers that they assured me was suitable masculine.
It felt odd, travelling alone in Toby's chauffeur driven car. I felt inhibited at talking to the driver and wasn't even sure about the etiquette. Toby's apartment was in an expensive gated development, though the flat itself was smaller than I had anticipated. Apart from a few books and pictures, it was quite plain and I wondered how much time Toby spent there.
When I arrived the first thing Toby did was kiss me, hard; the second was to rip all my clothes off; and the third was to fuck me, hard, without ever moving from the hall. To be filled by his huge cock was what I'd been waiting for. When it was over he whispered to me that when we'd eaten he was going to do it all again, only this time far slower; I couldn't wait.
We decided to leave our clothes off. Sitting drinking whilst being bollock naked seemed wonderfully decadent to me, and it gave me time to get a good look at Toby's body. He was in good shape, it looked as if he worked out. He had small nipples and a shapely, not over defined chest. His belly was smooth and the small patch of pubes was trimmed almost out of existence, I wondered what he'd look like shaved. His cock was uncut though the head was always clearly visible and his balls hung almost as low his flaccid cock. He was sitting with one leg over the arm of the chair, giving me a glimpse of his arse.
I'd taken extra care with my shaving that morning and had been experimenting with it, my pubes now stopped about an inch above my cock giving a shaved area right above it, an effect I rather liked which was set off even better because I was wearing a cock ring. This was a new addition, suggested by Darren and I now often wore one, liking both the feel and the look of it.
A meal was laid out in the kitchen, we at in a small eating area off the main kitchen. It was all delicious, when I complimented Toby he admitted that it had all been brought in (would that my entertaining was so simple). Dinner over, Toby simply lifted my legs up and started exploring my arse with his tongue, at first simply caressing my crack but then thrusting his tongue deeply into my hole. He slowly worked his way over my whole body, exploring it with his tongue. When he got to my mouth, he kissed me and then whispered, your turn. We changed places and I let my tongue wander over his body, starting with his mouth and working down towards his cock and his arse. Finally allowing my tongue to work its way up his wonderfully smooth crack and into his hole.
Only then did he fuck me, first on the chair on the kitchen, then on the sofa in the reception room, finally he lay on the floor, his cock almost vertical, and I lowered myself down, taking his cock deep into me. Finally we collapsed exhausted, both covered in cum and my arse not a little sore.
I began to note the time and wondered how and when the evening would conclude. Toby brought me another drink and asked me to stay the night. I was delighted but worried about my lack of change of clothes. I half expected for him to suggest I borrow his, but he took me into the bedroom and there was a brand new shirt and tie, my size and far more expensive than I'd ever buy. There was also a complete set of shaving equipment and a new tooth brush. I was amazed and, to tell truth, rather touched. Little of it got used that evening, we simply collapsed into bed, Toby didn't seem worried at dirtying the clean sheets (I suppose you don't if you have someone to launder them for you). I finally fell asleep with Toby's half erect cock still in my arse, a profoundly comfortable feeling for me.
Next morning, despite the shortage of time, there was breakfast, a fuck in the shower and Toby shaved my cock and my arse. My new shirt looked and felt great and I had enough confidence to suggest that I take him out next time (I daren't entertain him in my grotty little flat). He agreed and we made a date for 5 days time as Toby was away on business again.
I went through work in a bit of a daze which, perhaps, even Tom noticed. At any rate, the next day he took great delight in humiliating me. I was called in to a meeting in his office, it was an internal one and many of the people present were managers and department heads that I had dealt with. The meeting was not doing well and part of the way through Tom undid his trousers, called me over and got me to suck his dick.
Thinking about it, I'm not sure whether the intention was to humiliate me or to show his contempt for his staff, probably a bit of both. After I'd sucked him off, and cleaned his dick, he suggested that I suck anyone else's in the meeting, given that I gave good head. In the end I gave blow jobs to around half the meeting, some guys grinned others looked a bit shame faced and I think one or two were a little too embarrassed to get their dicks out in front of other people. Quite what this achieved I don't know. Afterwards Darren gave me a shit-happens sort of look, but I felt rather depressed. That evening I started work on my CV but realised that my actual job responsibilities at Artemis had declined considerably; my job title looked good on paper but my actual experience was limited, Tom didn't really trust us with anything serious as he liked to keep all control in his own hands. And even if I did manage to apply for jobs, he'd probably be furious and give me a crap reference.
Late that evening an email came through from Toby, another picture of his dick, this time apparently at a meeting though quite how he managed it I don't know. Shortly afterwards there came another one, this time not of his dick but of one of his colleagues, by this time they were in a strip club (a straight one), and this colleague had managed to get his dick sucked by one of the girls and was pleased for anyone to know it. I felt a little bit jealous, but had to tell myself that I had no reason to be, my relationship with Toby was too new and I had no reason to assume I was the only guy, the only person even, that he had sex with.