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I'd been Information Security Officer at a major financial institution for
3 years now. We were located to the east of New York City in a state of the
art office campus. Fifteen hundred employees all told. The work was
challenging. Cybersecurity was an ever-changing art, and I was kept busy.
One Friday night I was last out of the office when an email virus alert
popped up in our Group inbox. It pointed to a user who worked in the
executive suite, a personal assistant whose name was Amy Smith. She sounded
familiar. As I checked Amy's profile I saw from her staff picture she was
what would be termed a MILF. Yes, I remembered her vaguely, office party,
sexy but aloof. A secretary to some managers in the senior Back Office
management team, I'd say mid 40s to 50 years old, it was hard to tell these
days. There was no mistaking from her profile picture Amy was hot. Light
brown hair with blonde highlights, deep blue eyes, striking cheekbones,
full lips, her chin perhaps a little square. From her file, I could also
see she was single, and lived about a 15-minute drive North from the office
complex. Rather than delegating to offline support I decided to take a look
myself. I was 37, divorced, and hadn't had a girlfriend for a while, and I
wasn't going to be doing much that night anyway. Maybe she'd be thankful
for some personal IT support.
As I checked the alert in more detail, I was surprised at what I saw. In
this digital age where everyone has a smartphone, a PDA, a tablet, a
laptop, no-one really downloads porn at work these days. Some idiots might
do on the guest Wi-Fi, but the information I was scrolling through
indicated that Amy Smith's desktop PC and her work laptop had been used to
access a large number of adult-oriented websites. I immediately remoted to
Amy's desktop PC and logged on as an Administrator.
As I checked her browsing history, this appeared to be a regular thing for
Amy. Amy (or someone using Amy's PC, possibly a senior manager, I had to
consider that option) had been browsing hard-core porn sites, pay sites
even, and dating sites, a few of them aimed at the transgendered market. I
knew some people weren't that computer literate these days, but on a scale
of one to stupid, this was STUPID. I next checked Amy's email client and
found the quarantined email. She'd been getting notifications from dating
sites to her
work email address. Unreal. I still couldn't be 100% sure it
wasn't one of Amy's bosses with an uncontrollable lust for kink, so I
mentally marked this one down as "sensitive". I could see from checking the
online Org Chart attached to her profile that Amy looked after a couple of
very senior managers. What if one of them was the "freak"?
Dialing up my security management console intranet page, I then noticed
that Amy's laptop was currently actively connected to the company network
remotely. I instant messaged Amy immediately.
"Security alert, please call Mr. Bell ..." and then without really
considering it much I entered my cellphone number rather than the helpline
About 60 seconds later, my cell rang. It was an unknown caller. I picked
"Hi, Information Security Officer Rob Bell speaking, how may I help?"
There was a nervous pause. Then a slightly husky female voice started
talking. The voice was slightly deep, albeit in a sexy kind of way.
"Ah, ehm, Mr. Bell, this is Miss Smith. Miss Amy Smith from Back Office
executive on the 26th floor. I'm at home, ehm, working late, and I got a
message on my laptop to call"
"Yes, Miss Smith ..."
"Please, Mr. Bell, call me Amy"
"Yes, Amy. Amy there's a security issue with your laptop"
"Oh!?" Amy exclaimed.
"Yes, Amy. We need to get your laptop cleaned. I can talk you through the
procedure, or ..."
I know now I was being a little less than truthful, and I guess my baser
instincts had kicked in subconsciously. Maybe a trip to Amy's place (and as
I looked at her profile pic again, Amy was definitely a hot MILF), was what
made me fail to mention I could have cleaned the laptop remotely from my
desk in the office. Plus, if a senior manager was the guilty party I tried
to convince myself this might be better dealt with off-site.
Amy interrupted, "I don't know how to do that Mr. Bell. I'm not good with
"Rob, call me Rob. I'm still at the office Amy. I can see you live a little
North on the Parkway, that's on my way home. If you don't have guests or
anything arranged, I could call at your place and we could look at the
Amy hesitated for a few seconds.
"Well, yes, ah, I was just checking emails. I guess that would work. I
don't have any definite plans for tonight. Yet"
"OK, I'll be there in 20 minutes. Amy, can you do me a favor and shut the
lid on your laptop until I get there. Security issues like this are serious
and I don't want either of us to make the problem worse than it already is"
"Sure, Mr. Bell, I mean Rob."
I wrote down directions to Amy's place then ended the call.
Worst case scenario I thought I'd get to spend an hour or two in the
company of a hot MILF doing the necessary housekeeping on her laptop, maybe
getting to know her better. If this was an issue caused by one of Amy's
bosses we'd also need to discuss how to handle it sensitively (being
honest, top dogs got away with a lot of shit in our company, I'd seen this
before). In actuality, the security breach was minor, after all our systems
had the virus file quarantined. The situation we were looking at here had
been exacerbated by the breach of company policy on online behavior, and
porn usage to the extent I'd just seen by any ordinary Joe in the company
was likely a firing offense. Best case formal warning. In truth, I should
already have been escalating to my management. Let's see what the hot Amy
had to say about the situation. I didn't necessarily want to get Amy into
trouble, but I had a job to do.
I grabbed my coat and car keys and headed to the parking garage.
After a wrong turn, it took me slightly longer than 30 minutes to get to
Amy's building. She had a duplex in a newish condo development. I parked in
a guest parking slot, readied myself and walked up to Amy's front door. I
pushed the doorbell. About 30 seconds later I saw a shape through the
frosted glass, then the door opened.
A nervous Amy looked at me. Wow. She was even hotter in the flesh. Tall and
thin, with a very decent rack partially covered by a deep green silk blouse
open to show some cleavage (I guessed boob-job, and a good one at that).
Long sensual legs descending from a short black tight pencil skirt to feet
in red high heels. Expertly applied make-up with light brown and blond
highlighted hair tucked up. The look finished with brown rimmed eyeglasses.
This was a red-blooded male's secretary sexual fantasy look if ever there
"Ah, hi, eh, Mr. Bell. I mean, Rob! Come in please", Amy smiled, a little
nervously it seemed to me.
I walked in behind Amy, not missing the chance to look at her tight ass
swaying through her skirt as she led me to a couch in the open living area
the front door had given immediate access to.
"The laptop's over here"
There was a low oval glass table by the couch. There I could see the dark
gray work laptop, lid closed shut, next to what looked like a glass of
white wine and an ashtray with 2 cigarette butts smeared with dark red
lipstick. The shade Amy was wearing now. An open pack of Marlboro Reds lay
nearby along with a silver cigarette lighter.
Amy pointed to the couch and I sat down.
"I'm going for a top up, Rob. Would you like a glass of wine? A beer? I
have some beer in the fridge"
"A beer would be great, Amy. Then we'll get to the bottom of this laptop
Amy squinted at me nervously.
"One minute, Rob".
As Amy stepped through to the kitchen area I couldn't take my eyes off her
taut ass, the shape accentuated beautifully by her tight skirt. I also
noticed black lines up the back of Amy's tights. Fuck, Amy was a hot one.
In under a minute Amy returned and handed me a Coors. She had filled her
wine glass nearly to the top and took a nervous gulp as she sat down beside
"Mr. Bell, sorry, Rob, is it ok if I have a cigarette?" Amy asked
"Of course, it's your house, and it's Friday night, anything you like.
Hopefully this won't take too long". I smiled then continued, "Before we
get to the laptop, do other people use it?"
Amy clicked her silver lighter on and took a deep pull on her Marlboro as
she lit it. She exhaled a thick plume of smoke towards the ceiling.
"No. I never share passwords."
"OK, Amy. The thing is, on your desktop at work, and I'm pretty sure also
this laptop, there's been a lot of unauthorized access to some websites of
a, I guess you'd say, 'mature' nature"
Amy's eyes widened. She looked at her cigarette, flicked some ash into the
ashtray in front of her, then took another deep drag.
"Rob, I'm sorry, I, well, ..."
"Amy, don't get upset right now. In some ways, you've highlighted an issue
with our web-blocking software. You could argue it's my department's fault
that you can access these sites. They should be prohibited. I'll be working
with my team on that first thing Monday. OK. Before we look at the laptop,
you're sure no-one else could have accessed your machines?"
Taking a quick nervous drag of her Marlboro, Amy shook her head.
"OK, shall we?", I nodded to the laptop. "Please log on and we'll check a
few things and clean things up if necessary"
Amy crushed her cigarette out.
"Rob, do we have to do this? I know I'm in trouble. But can't you just wipe
the laptop, give me a fresh one, I don't know, however you do this stuff?"
Amy nervously reached for another Marlboro, lit up. I noticed that Amy had
a very sensual way of smoking a cigarette. To be honest, this close to Amy,
with the way she looked, I was starting to feel my cock stiffen in my suit
"Maybe we just say it's broken? I could drop it on the kitchen floor?" Amy
seemed to be a little desperate.
"I'm sorry Amy. If we don't do this together now, I'll have to take the
laptop, it's company property after all, and it will be much worse if we
have to do this with Human Resources in the room"
Amy took a deep pull on her cigarette. "OK, but, there are personal things
on there that you mustn't tell anyone at work about. Please?" Amy put the
hand without the cigarette on my knee.
"Let's look and work out what we do, OK?" I was trying to put Amy at ease,
but I was also quickly realizing this could go even better than I'd
anticipated. I left Amy's hand on my knee, then opened the laptop.
Amy lifted her hand from my knee, dangled her cigarette between her lips
and logged on.
Fuck, she really was bad with computers. In front of me was an almost full
screen webpage for a site for "TV Chicks" to hook up on. I could see a
personal profile. "AmyTV" Wait! I was confused. I could see Amy in a black
Basque and stockings staring at the camera. It was Amy Smith, the hot
mature sitting next to me on the screen. I gulped. Fuck, this was
Amy broke me out of my stunned silence.
"Rob, you can't tell anyone about this".
I quickly flicked to another screen, a photo roll. I almost fainted. Amy in
a pink pvc bra and open crotch pvc panties, black patent leather thigh
length boots, her thin stiff 7-inch long cock pointing at the camera. I
automatically started scrolling through the photos.
After a few shots of Amy in various erotic poses, I got an even bigger
surprise when the picture on the screen showed Amy with a younger female
assistant from the HR team in our office, Suzy Seeger. Both were posing on
the couch, dark-haired dark-eyed Suzy, who most of the guys in the office
felt had the best tits in the company, was naked except for a pair of hold-
up stockings. Amy was wearing the black Basque I'd seen in the hook-up site
profile photo I'd looked at initially, a garter belt and stockings. Amy had
a hand under one of Suzy's huge floppy breasts. Both were smoking. My hard-
on went up a notch.
I scrolled forward as if in a dream. I forgot Amy was next to me. I was now
scrolling through pictures from the same session. Beautiful, big-titted
Suzy sucking an older guy's cock, only his body visible, gray pubic hair.
TV MILF Amy sucking the same older guy's cock it looked like, the guy's
face wasn't visible in this shot either. Suzy sucking Amy's she-cock. Wow!
Amy's cock wedged an inch or so into Suzy's gaping pussy. Then the shocker.
Amy's she-cock in the older guy's mouth. Fuck. I recognized the older guy.
Lawrence Bodicker, head of Accounting. I took a deep breath. I turned to
"Amy, you shouldn't have this shit on a work laptop"
The photos had got me fully turned on. I was stiff in my pants, my cock was
almost bursting to get out. I clicked through the rest of the pictures. The
last two shots. Massive tits Suzy facing the camera, a reverse cow-girl DP;
Amy's she-cock poking into Suzy's tight butthole from underneath, Lawrence
Bodicker's short fat cock slipped into Suzy's cunt.
As I turned back to Amy, she placed her hand on my crotch.
"Rob, I don't want to lose my job. I also don't want Mr. Bodicker to get in
trouble. Or young Suzy. Mr. Bodicker has a wife. Kids. Suzy's a great girl.
How about we work this out? I can feel how you feel about me? I take it
you've never been with a trans-girl? Let me show you how good this can be"
I let out a pant as Amy squeezed my cock through my pants, hard.
As I opened my mouth to speak Amy leaned in and kissed me hard. I gave my
answer by responding to Amy's kiss wildly, forcefully pushing my tongue
back into Amy's mouth.
Amy gave my cock a tighter squeeze through my pants, then lifted both her
hands and started to unbutton my shirt. We continued our French kissing
until Amy got to the last shirt button above my pants waistband.
Amy stood up and slowly unbuttoned her silky green blouse. She slipped the
blouse off as I disentangled my own suit coat and work shirt and threw them
to the side of the couch. Amy's tits looked magnificent, they were tightly
squeezed into a low cut lacy black brassiere. Not as big as Suzy's natural
jugs, but still sexy as fuck.
Amy smiled at me staring at her breasts.
"Like them, Rob? They cost a lot of money"
I gulped a "yes" by way of response as Amy unfastened her bra from behind
and her firm round silicon boobs popped out.
Amy then unzipped her skirt which slid down her thighs revealing striped
top hold up stockings. Black lacy panties covered what now appeared to be a
not insignificant bulge. Fuck, this was exciting me. Much more than I
Amy pushed me back slightly onto the couch and unbuckled my belt. Quickly
undoing the button on my pants waistband, she expertly unzipped my pants. I
arched my back against the couch carefully, allowing Amy to pull my pants
down. She threw these to my right and then squeezed my aching hard-on
through my boxers. As Amy loosened her hair which flopped down over her
shoulders in front of me, she leaned closely into my groin and started
nibbling on my cock through the cotton of my boxer shorts, her sensitive
bites driving me crazy with desire. Fuck, I was loving this.
Amy raised herself up onto the couch beside me, and we started to kiss
passionately once more. I could feel Amy's hard thin rod rubbing against my
leg. Instead of revulsion I was surprised to find it was turning me on.
Then all of a sudden, the doorbell went. FUCK!
As we paused, Amy looked at me and smiled.
"Rob, trust me on this one. Stay just as you are on the couch"
I looked back at Amy aghast. What the fuck! I was suddenly terrified. Amy
wasn't seriously going to let someone in? With me with a stiff cock busting
out of my boxer shorts and my work clothes scattered around the floor?
"Amy, you must be fucking kidding, you ..." and then to my horror the door
to the room clicked open and in walked Suzy Seeger. She of the best tits in
the office fame.
FUCK. ING. HELL.
Suzy just smiled at me from across the room, took a deep pull on the last
remnants of a cigarette she was holding, walked towards Amy and me, stubbed
the cigarette out in the ashtray on the oval coffee table and immediately
pulled Amy to her and gave her a slow lingering tongue kiss.
I was speechless. Amy, her cock still fully erect, sat down to my right,
and Suzy, discarding a beige short rain coat to reveal a short powder blue
colored lycra dress which her massive tits seemed to be stretching to get
out of, sat down to my left.
Amy spoke first.
"Rob, when you called me to tell me you were stopping by, I knew we, I mean
Suzy and me, were in trouble. I called Suzy. I mean, I was prepared to take
the chance of seducing you myself, I can be very persuasive with a man's
dick in my mouth, but if you hadn't been so open to me being trans, well
Suzy here was back-up."
Suzy had picked up the pack of Marlboros, first lighting one and passing it
across me to Amy, then lighting one for herself. She still hadn't said
anything. But as she exhaled a flume of blue gray smoke, she pressed her
massive tits against my left arm.
"Rob, do what you need to do to my laptop and work PC. But first, let's me,
Suzy and you have a little fun. Suzy thinks you're cute, anyway, don't you
Suzy exhaled another plume of smoke.
"Had my eye on this one for a while," Suzy smiled, "Much cuter than the
managers we usually fuck."
I noted Suzy had said 'managers', plural.
Suzy put her hand to my face, tilted my mouth to hers, and kissed me hard,
her gorgeous wet lips and tongue forcing my own mouth open. I felt Amy,
grip my boxers and free my cock, then shuddered as she locked her lips
around the bulbous head of my shaft. I tensed like I'd received an electric
shock. Christ, she, he, she, I was confused, was GOOD. Amy started sucking
my cock with a slow up-and-down motion, as Suzy broke off our kiss and
peeled her lycra dress off from the top. My eyes widened as Suzy's massive
natural melons flopped free. Fuck, they were amazing.
As she removed a thin black thong she was wearing, Suzy urged me on.
"Suck them Rob, go on, suck my massive titties!"
I didn't need to be asked twice, greedily wrapping my lips around the giant
areola of one of Suzy's huge boobs, before hungrily switching to the other.
Amy removed her mouth from my cock, took a last deep draw of her cigarette,
and stubbed it out in the ashtray. Suzy also leaned back and discarded her
cigarette in the ashtray.
As I leaned back, this time it was Suzy who grabbed the base of my shaft
and swallowed my cock. I convulsed. Amy smiled at me, then tapped Suzy on
"Suzy, let's share"
This was like living a wet dream. Amy and Suzy both ran their tongues up
the length of my shaft, then took turns teasing my glans with their tight
lips. Amy then took control of my cock head as Suzy started to flick her
tongue over my tight ball sack. I started to moan loudly. This seemed to
focus the 'girls'.
Freeing my cock from her mouth Amy leaned back allowing Suzy to straddle
me. With the minimum of fuss Suzy gently directed the tip of my cock to the
entrance to her by now dripping wet pussy, then lowered herself down
firmly, spearing her cunt with my, by now, throbbing hard cock. We
simultaneously let out a gasp, then Suzy started a steady rhythmic motion
as she started to milk me with her tight cunt hole. I felt Amy give a tight
squeeze of my balls, then stand up.
I was losing myself in Suzy, this was the best sex I'd had in years. Hell,
ever, if I was being honest. I noticed Amy position herself on the back of
the couch, the upper part, then carefully slide her she-cock into Suzy's
mouth, only inches from my own mouth. Suzy growled as she upped the pace on
my rod, and Amy also started to let out breathless high pitched moans as
Suzy's succulent lips milked her cock.
Then it happened.
Suzy slid Amy's cock out from between her lips and leaned her mouth towards
mine, directing Amy's shiny purple cock head towards my own lips with her
tongue. My breath stopped for a second. Then without really thinking I
wrapped my lips around Amy's she-cock. And started to suck. Suck a cock,
for the first time in my life.
Suzy almost squealed in delight as Amy started to pump my mouth with her
thin stiff delicate rod. Fuck! I was sucking a cock. I didn't care, it felt
amazing, I genuinely surprised myself by how much I was enjoying this, my
first time sucking tranny cock.
Suzy suddenly stopped pumping, and issued a guttural moan.
"FUCK, I'm cuummmmiiinnnggg!"
Amy reacted by pulling back slightly withdrawing her cock from my mouth.
Sliding down so her face was close to Suzy's, Amy locked her lips onto
Suzy's as Suzy's orgasm rippled through her body, her fleshy tits quivering
in time to the contractions I could feel emanating from Suzy's soaking wet
vagina, still tightly clamped around my erect member.
As Suzy's orgasm subsided, Amy turned to face me.
"Don't come yet, Rob, it's my turn. Fuck my tight asshole, please, fuck me"
Suzy pulled herself off of my still rigid cock, then sat down alongside me
on the couch.
Amy grabbed my hand.
"Rob, behind me on the floor. Fuck me from behind while I lick Suzy's cunt"
Amy got down on all fours as Suzy lit a cigarette. Suzy held the cigarette
so that Amy could take a puff, then directed Amy to her glistening wet
cunt. Amy tongued Suzy's clitoris, then started licking.
I knelt behind Amy's ass. Pinching my soaking wet shaft at the base, I
positioned the tip of my cock at the entrance to Amy's poop tube, then
slowly pushed my groin forward.
Fuck. The intense feelings that filled me as I slid my full length into
Amy's shemale butthole were like nothing I'd felt before. Amy stopped
tonguing Suzy's cunt for a second. Then I started pumping. Amy started
squealing in ecstasy as I rode her. Suzy started to feverishly rub her
I knew I couldn't last long. As I felt the pressure build, I let myself go.
With each spurt of my come into Amy's tight asshole I let out a loud yell.
While I'd shot my load into Amy's rectum, my eyes had been closed. I opened
my eyes to see Suzy smile at me.
"You're good, Rob. I hope you can re-charge your batteries. I really want
to feel your stiff cock in my asshole"
Amy slipped my spent cock out of her asshole.
"Rob, do what you need to do with the laptop. Then after, Suzy and me will
fuck your brains out again. OK?"
I nodded. This was going to turn into a very good Friday night.
Part Two to follow.