Date: Wed, 4 Jun 2008 07:09:13 +0000
From: Shaved Smooth <shaved_smooth@live.co.uk>
Subject: My Progress - Part 3

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.