My So Called Sex Life Part III
- 4 years ago
- 50
- 0
True Stories Part III free porn video
True Stories
Part III
By
Michele Nylons
This is a continuation of my True Stories series, where I tell my
readers about my real life adventures. In the next two instalments I
will tell you about some of my encounters that were not particularly
satisfactory. As most closet Transvestites will know, there are a lot
of losers out there and some of them can even be a little scary.
Story One - The Reluctant Stalker
As most of my readers know I live in Australia and travel a lot with my
job; this assists me greatly as I can maintain an apartment in a
different city from my family home and use it for Michele's encounters
and other fun activities. At the time of this incident I had a nice
little two-bedroom unit (town-house) in one of Australia's capital
cities. It was located in a quiet street and was set well back from the
street and quite secluded from the adjoining units; it was just the
place for a closet Trannie to ply her trade.
I had been advertising my availability for casual meetings on the
noticeboards of a couple of sex shops in the area (before any of you
groan, read parts one and two of this series and you will see how I vet
my punters; although in this case the vetting process wasn't hugely
successful), and had enjoyed a number of pleasant casual encounters with
admirers who had responded to my advertisement.
My 'Michele' cell phone rang one evening and a guy introduced himself to
me calling himself Peter. He described himself and said he had never
been with a Transvestite before but would really like to try it. I
could tell by the way he kept calling me "mate" that he hadn't been with
a TV or crossdresser but I was willing to talk to him and see if he
might be acceptable as a potential admirer.
He was in his forties, large build, bearded and worked as a tradesman
and wanted to meet discreetly during the day, mid-week as he was
married. I said it would be difficult for me to meet during the day
during the working week due to my work commitments but that I'm sure if
he was really interested we could work something out.
Peter asked me to describe myself and my interests, which I did. He
became particularly excited when I described how I wore miniskirts,
stockings, high heels and lots of makeup; and again he expressed a
strong desire to have his first encounter with a Transvestite.
I am always very wary of men who are first time admirers as they are
often enamoured with the fantasy of being with a Transvestite and have
masturbatory fantasies about what it would be like; and then they find
they can't go through with the reality of the situation when they get
the opportunity realise their fantasy. I told Peter this and he
insisted he was genuine. I told him that if he really wanted to
experience an encounter with me I'm sure he could find some excuse to
get away one evening or maybe for a couple of hours on the weekend, and
then I could attend to his needs. He said he didn't think so; so I
thanked him for calling and wished him the best.
I thought that would be the end of it but over the next two weeks Peter
kept calling me on my cell, mainly during the evenings and on weekends
and expressed how much he really wanted to have an encounter with me but
insisted that we could only meet during the day on a weekday. I
suspected that on many of these occasions he was drunk but I told him
that a meeting during the day midweek was highly unlikely. I probably
should have just ignored him but he was genuine enough to leave his cell
number (I definitely will NOT meet with a person who has suppressed
their caller ID on their mobile phone when they call me) and he asked me
to call him if there was ever an opportunity to meet midweek during the
day.
As it turned out I was able to get a half day off from work one day and
debated whether I should call Peter or not. I was feeling particularly
horny as my regular boyfriend, Buster (more about him in a later
instalment), had not been in town for a while. I debated the pros and
cons of meeting with a 'first-timer' at my flat during the day and
decided it would be safe enough. I sent a text a message to his cell
"call MN if free to meet" and waited to see what would happen.
Five minutes later my Michele cell rang,
"Hello Michele Nylons speaking," I answered, knowing full well it was
Peter from the caller ID.
"Well; can we meet then?" Peter's gruff voice responded.
"Yes we can meet; but there are a few ground rules," I responded, "I
need an hour to get ready and then you call me from (a street close to
where I live) and then I'll give you the address where I live ok? My
place is only five minutes away from there by car."
"Fuck that!" Peter exclaimed, "I can only get away from the job for
about half an hour and I don't want to waste most of my time sitting in
a fucking car waiting to call you."
I should have called the meeting off then but I was quite horny and a
little sympathetic to his plight. I went on to explain.
"Look honey, I rush things along I can be ready in half an hour ok?" I
asked.
"Well I suppose I can get away long enough to spend half an hour with
you," he sulked.
"Well look Peter, you're the one who has been calling me incessantly
begging for a meeting. This is how I do it when I meet guys for the
first time ok?" I responded.
"Ok, I'll call you in a half hour Michele. I hope this is worth it," he
replied and hung up.
Again I debated whether to meet this guy, but my excitement and the
anticipation of meeting an admirer overcame my caution and I sauntered
off to the bathroom to make my transformation.
I shaved my face very closely, showered and cleaned my teeth but did not
worry about douching. Being a first timer, and only having half an hour
to play, I decided that Peter was not going to fuck me this afternoon;
if I liked him I might let him on another occasion I giggled to myself.
I went to the spare bedroom and closed the curtains, sprayed some air
freshener around, cranked up the air-conditioner and opened the walk-in
closet where my Michele accoutrements were kept. I rummaged through my
makeup and took what I needed back into the bathroom to fix my face.
I applied a few dots of bright red lipstick to my cheeks, chin and neck
and rubbed the lipstick in with a damp makeup sponge. This is a trick I
had learned to hide any dark patches caused by facial hair follicles
(sometimes called five o'clock shadow). I then applied a liberal amount
of foundation and set it with an application of face powder. I did my
eyeliner as usual before I did anything else, then applied some
turquoise and pink eyeshadow and some blush on my cheeks. I applied a
liberal amount of mascara to my lashes and then applied a final coat of
glossy face powder all over and then carefully applied two coats of
lipstick and bit down on a tissue to set the lippy. There, my face was
done; hurried but acceptable.
I went back to the spare bedroom and rummaged amongst my lingerie
collection. As I hadn't shaved my legs for a few days and had no time
to do so now I decided to wear a pair of sheer to the waist, taupe
pantyhose as a foundation garment. As I wouldn't be letting Peter fuck
me the gusset wouldn't be a problem (besides plenty of men have ripped
open the gusset of my pantyhose to get access to my bottom before). I
slid them up my legs and smoothed the sheer nylon along each leg and
around my buttocks and crotch. The tingle of the nylon against my skin
and genitals and the anticipation of the forthcoming encounter caused me
to become turgid. I tucked my semi-hard penis between my legs and
slipped on a pair of bright red, full-cut, nylon panties.
Next I stepped into a white lace suspender belt. Again, if I was
meeting someone who needed to remove my panties for access to my bottom
I would have put the panties on over the suspender belt to allow my
panties to be pulled down without getting caught on the garter straps,
but today this was not necessary. I slipped on a pair of black nylon,
fully-fashioned, stockings over my pantyhose and up my legs and fastened
them to the garter clips. I was going for look and feel here rather
than the practicality of permitting access to my genitalia. I figured
that having only half an hour to play, a first-timer could make do with
my hands and mouth.
I slipped on a pair of black high-heeled court shoes and wriggled into
my favourite red Lycra miniskirt. I pulled on a white brassiere and
stuffed the cups with old nylon stockings; I was going for speed, not
authenticity. I buttoned up a white nylon blouse and tucked the tails
into my skirt. I grabbed a wig, a brunette bob with lighter highlights,
and went back to the mirror in the bathroom. I pulled on the wig,
adjusted it and gave it brushing. I went back into the bedroom and
found a nice pair of silver drop earrings and clipped them to my ears; I
put matching necklace around my neck. There! I was done! From man to
Michele in a little over twenty minutes!
I tottered downstairs to the lounge, my high-heels clicking on the
wooden stairs and tiled floor, and poured myself a glass of red wine,
lit a cigarette and put my cell phone on the coffee table next to my
wine glass, and started painting my nails. I didn't think I'd have
time, but if I painted my fingernails with just one coat of nail-polish
and wasn't too fussy about the finish I could probably get them done
before Peter arrived. Men love painted fingernails.
I had only one fingernail left to paint when my phone rang; the dial
displayed 'Peter', so I picked it up and answered,
"Hi honey, you ready for a good time," I cooed in my sexiest imitation
sotto femme.
"What's the address!" Peter practically growled into the phone.
For one last time I considered whether I should meet this guy or not;
then I gave him the address.
"The front door will be unlocked but closed," I instructed, "let
yourself in and lock the door behind you; I'll be in the lounge out of
sight of the open door just in case some nosey neighbour is looking," I
said.
"Yeah, ok Michele. See you soon," Peter said and rang off.
I picked up a bottle of perfume, my favourite Poison ?, and sprayed a
liberal amount on my neck, wrists and under my skirt. The curtains were
already drawn so I dimmed the lights and stood up to greet my guest. I
moved into position where Peter would see me as soon as he came through
the door but where I would be out of the sight line of the street and
adjoining flats.
A couple of minutes later there was a loud rap at my front door.
'Fuck,' I thought, 'I told him to come in and lock the door after he
entered.' So was this Peter? or was it someone else? What a dilemma!
Should I answer the door, or will there be someone there besides my
prospective admirer?
Then the door opened and Peter strode into my flat slamming the door
behind him. He stood there in the entry and surveyed my flat, casting a
critical eye around the place. He was a big man with a solid paunch
that hung over his belt; he had dark curly hair and piercing eyes. He
wore tailored work shorts and a golf shirt. An Alpha male to be sure,
he exuded arrogance. I actually found his maleness attractive I must
say. I moved to the centre of the lounge room and pirouetted.
"Well do you think," I asked.
"At least you like a woman even if you sound like a bloke," he responded
and strode across the lounge to stand in front of me.
"Do we do it here or in the bedroom?" he asked.
I was a little baulked but aware that he was probably nervous as this
was his first time with a Transvestite. He was probably using arrogance
to cover up his nervousness.
"I have a spare bedroom upstairs that I like to use," I said.
"Well what are we waiting for, lets go Michele, time is running out," he
replied, looking at his watch.
I led the way upstairs and he followed closely behind me. As I started
to climb the stairs ahead of him his rough hands ran up my thighs and
onto my buttocks, his fingers rasping on the sheer nylon of my stockings
and panties.
"Fuck that feels good," he groaned, "Women today never wear stockings
any more; I love the feel of stockings."
He continued to rub my legs and bottom all the way to the bedroom. When
we were finally standing next to the bed I turned and faced him. He
looked me up and down and steadied his gaze on my face.
"You like a real fucking woman you know; pity you'll have to get that
shit off your mouth," he said, and reached out and wiped most of my
lipstick off my lips with his thumb.
"If I get any of that shit on clothes or face my wife will fucking kill
me and if the guys at work see it they will guess what I've been up to."
I was quite taken aback by what he had just said and done, wiping my
lippy away like that.
"Well Peter, I told you I am discreet. I would never get makeup on your
clothes and you can always use my shower to remove any traces I leave on
you," I said, a little angry at his actions.
"I suppose I could get naked, couldn't I," he answered, as if he had had
an epiphany.
"Well why don't you do that while I put my lipstick back on. I'm sure
you would prefer me to look as feminine as possible?" I replied and went
into the bathroom and applied two coats of lipstick with a slightly
shaking hand.
I was beginning to wonder again if I had done the right thing letting
this guy come to my flat. 'At least with him naked in my bedroom I
should be able to keep some control of the situation,' I thought.
I tottered back into the bedroom and found him standing naked, his
clothes neatly folded at the end of the bed. His was quite hairy and
his large gut was hard like a basketball and hung out over his genitals.
His short stubby penis was hard and stood proud of the thick thatch of
his pubic hair. I moved close to him and reached up and kissed him. He
took my hand and put it straight down onto his stumpy cock, slipped his
tongue between my lips and pulled me close; his other hand going under
my skirt, firmly squeezing my pantied buttocks.
His beard tickled my face and his mouth tasted of his lunch and
cigarettes but I immediately became aroused and responded to his kisses
and rubbed my body against him whilst my painted fingernails fluttered
up and down his penis. His little pink muscle was rock hard and
quivering in my hand.
"Easy, I don't wanna come yet," Peter whispered, and he slapped my hand
away from his manhood.
He held me in a bear hug, squashing me against his big body, his lips
crushing mine and his tongue quivering in my mouth. Peter's hand
slipped back under my skirt and began to roughly stroke my stoking tops,
his breath was gasping as his hand his pulled at my suspender strap and
buried itself in the nylon sheath between my stocking top and my
pantyhosed thigh. As one hand massaged my nylon encased thighs the
other slipped around from my buttocks to the front of my panties.
By this time I was quite aroused and erect in my nylon knickers; Peter's
hand slid across the sleek nylon front panel of my panties tracing the
outline of my cock. I shuddered and groaned and pushed myself harder
against him. Suddenly Peter whipped his hands from under my skirt and
gripped my shoulders and pushed me back out of his embrace.
"I don't know if I'm ready to touch you down there; I'm not a poofter or
anything," he whimpered.
I was taken aback a little. As I have explained (and most Transvestites
know), admirers often choke or panic during their first sexual encounter
with a Transvestite or Crossdresser. Peter seemed to have gotten over
his initial reservations and was certainly enjoying himself with me up
until then. It was probably the first time he had touched another penis
and the reality of the situation had probably just hit him. I went into
damage control.
"Never mind honey, just lie back here on the bed and let Michele look
after you," I cooed.
Peter lay down on the bed; his hairy body was rigid but his tiny cock
had become flaccid and had almost disappeared in the tangled thatch of
his pubic hair. I sat down next to him and began to run my hands over
his body; my red nailed fingers stroking and fondling. He started to
relax again and he extended a hand and stroked my face.
"Fuck you are pretty good looking for a guy; that makeup and shit you
wear really makes you look like a woman," he said.
I didn't know wether to be complimented or insulted but I decided that
Peter was having real problems coming to terms with the fact that he was
having a pleasurable encounter with a Transvestite.
"Peter honey, if it helps, just think of me as a woman and enjoy what
you see and feel. You don't have to touch me anywhere you don't want
to. You don't have to do anything you don't want to," I whispered
trying to put him at ease.
I bent over and gently brushed my lipsticked lips on his. He responded
by pulling me to him and plunging his tongue deep into my mouth. I lay
on my side against him and continued to kiss him and stroke his fat
hairy belly and upper body. I slid a stockinged leg over his and slowly
rubbed my nyloned calf against his groin. Peter started to push up with
his lower body rubbing his hardening cock against my leg. I kissed him
harder and scraped my fingernails gently all over his body, occasionally
cupping his testicles and gently fondling them while my stockinged leg
rubbed against his tumescent penis. I felt a wet patch develop through
the double layer of nylon of my pantyhose and stocking on my right ankle
and calf where my leg was rubbing against his cock. Peter was groaning
now and close to coming.
He was certainly in a rush that's for sure; he grabbed my hand and
pushed it down into his groin and I circled his throbbing little member
with my fingers and began to gently stroke him whilst at the same time
kissing him deeply and rubbing my leg against his belly and thighs.
Peter abruptly pushed me away and at the same time I felt a scalding hot
stream of semen erupt from his cock and shoot over my hand, landing on
my leg where it glistened and soaked into my nylons, the secretions
drenched through the two layers of nylon and warmed my skin.
I quickly moved my head down and placed my lips over Peter's squat
pulsing cock and slavered at his member with my tongue. Steam after
stream of hot viscous semen erupted from his cock and I was forced to
swallow as my mouth flooded with his spend; some of it escaped my mouth
and spilled over my lips and ran down my chin. Peter's hands went to
the back of my head and pulled me down on him with such force that my
wig began to slip forward. He was groaning and thrashing as he orgasmed
and eventually he calmed and became still, releasing his grip on my
head. I was cleaning up, licking the sticky fluid that had matted in
his pubes, when his hand came down again and pushed me away.
"Ok that's enough thanks," he said matter-of-factly.
"Fuck I needed that, the missus hasn't given me a root for months; fuck
I came like a train. Now where's the fucking shower!" Peter demanded
hardly looking at me.
"Through the door and across the landing," I answered as he lifted his
large body off the bed.
"Are you ok," I asked, "some guys get 'post coital regret' after there
first time with a Transvestite."
"It doesn't mean you are gay or anything," I said sympathetically.
"You fucking bet I'm not a poof; I just got my cock sucked by a Trannie
that's all. I didn't fucking suck yours or anything!" he growled and
stormed off to the bathroom.
I sat on the bed very disappointed. Not only was I sexually frustrated,
this arsehole wouldn't even acknowledge my presence now that he had
finished with me; he wouldn't even look at me!
I heard the toilet flush and then the shower run for only a few minutes
and Peter reappeared at the doorway, my towel wrapped around his girth.
"Didn't have time for proper shower; just washed me cock and that???hey
get off me fuckin' clothes you dumb cunt!" he growled.
I had inadvertently sat on his shirt and shorts that were folded on the
end of the bed. I quickly stood up as he swaggered over to the bed and
grabbed his clothes.
"I hope you haven't wrinkled these; how the fuck will I explain that at
work," he complained stepping into his shorts and buckling the belt
around his girth.
He slipped on his golf shirt and squeezed his feet into sports socks and
trainers. He stood up and closed in on me, looking me in the eye and
seeing my disappointment.
"Hey don't worry Michele, maybe next time you can come."
He grabbed my buttocks and squeezed them.
"Fuck you've got a great arse; next time we might go a bit further if
you know what I mean," he laughed, slapping me on the buttocks and
striding out the room.
I followed him down the stairs my heels clattering on the wooden treads.
At the bottom of the staircase he stopped and surveyed my flat, which
was an open plan with combined kitchen, lounge and dining room.
"Yeah, not a bad pad you've got here; just the job for this sort thing.
Nice stuff you have too," he said indicating my furniture and
accessories with his chin.
Now, although I was sexually frustrated, I just wanted this man gone out
of my home.
"Yes, well thanks Peter, if you could just leave through the front door
and watch out for any nosey neighbours," I asked, my red painted
fingernail pointing at my front door.
"Fuck that," he said, "I parked around the back in your car space," he
snarled heading for the kitchen door which led out to my back porch and
the home unit complex car park.
"But I asked you to park out front on the street; what do say if anyone
sees you leaving?" I implored.
"Don't panic Michele, it's the middle of the afternoon, who the fuck
will be interested in your comings and goings?" he said over his
shoulder and went out the door.
I flicked the lock and watched him stride to his car, a big four-wheel
drive with the logo of a local Government department on the door. Just
what I needed if one of my neighbours asked why a man from a certain
Government department had paid a visit to my house in the middle of the
day. My mind was already inventing a story to cover the situation. My
head was spinning; Peter had been in my house for only twenty minutes!
I resolved that I had seen the last of Peter; he would not be invited
back. I would like to report that I did something spiteful to take
revenge for the way I had been treated but I'm afraid I have to be
honest. I went back into the bedroom and masturbated thinking of Peter's
stumpy fat cock shooting stream after stream of hot semen into my mouth.
Peter kept calling me over the next week, again mainly late at night and
mostly drunk. He apologised for his behaviour and promised that next
time we met he would treat me nice and even promised me sexual
gratification. I begged him off each time and in the end I requested
that he stop calling me when he was drunk.
All went well until about two weeks later on a Saturday when I was at
home doing my housework. I had had an encounter the previous evening
and was expecting another that night and my body was fully shaved and my
toenails still painted. Other than that I was in drab (dressed as a man
for the uninitiated) just wearing a pair of short shorts, shirt-less and
barefoot as the day was particularly hot. I was vacuuming the lounge
room tiles and rug when I couldn't believe my eyes; there was Peter
striding across my front lawn!
He saw me through the sliding glass doors and came directly to my front
door, which was open, with just the screen door closed and locked. I
went to the door, as he had seen me it was pointless pretending I wasn't
home.
"What the fuck are you doing here," I demanded through the locked screen
door, "I never see any admirers except when I'm dressed as Michele!"
"My wife's away so I thought I would see if you might be interested in
meeting," he replied.
"What? Is your phone suddenly broken! Get the fuck out of here! Do you
think I sit around the house all day dressed in drag hoping someone
comes around for an uninvited fuck!" I was really angry now.
"Well you won't answer my calls any more," he bleated.
"And I won't be answering them ever again," I exploded and slammed the
door.
I watched through the glass doors as he sauntered away. I closed the
blinds and got myself a stiff drink. I realised now how the situation
was; this guy was infatuated with me but unable to come to terms with
his lust for a Transvestite. He would only call me when he was drunk
and horny, or when his sexual urges overcame his trepidation. I made
the decision then and there that I would never see this guy again.
Peter kept calling but I refused to answer his calls. Even worse I
would occasionally see his car parked in my street and see him sitting
behind the wheel watching my house. As it turned out, I was moving
house in a few weeks to new apartment and I was glad when I finally did.
By then Peter had stopped calling and I hadn't seem him outside my unit
for a while, but I was still relieved when I finally moved.
As a footnote, do you know the prick had the cheek to call me about
three months later!
"I was just going through my mobile phone and deleting all the numbers I
no longer use," Peter said.
"I'm really sorry if I upset you and I was wondering if there was any
chance we could get together." he practically begged.
"Not a fucking chance!" I replied and hung up, safe in the knowledge he
had no idea where I lived.
Footnote:
For the information of my avid readers, I intend to complete the "Whores
and Pimps" series next, as I am aware that I have left the story
hanging. I also intend to add another instalment of "Planet of Men"
which unfortunately does not appear to be very popular.
I also have a few more "True Stories" to tell; but I am getting the urge
to reprise "Lady In The House", which I believe was my best work. I
think Michele got off too lightly at the end of the series and may need
to go back working for Eddie and Steve in the Chelmsford prison brothel.
Mei
- 15.06.2021
- 18
- 0
A Mother s Helping Hands Part III
- 4 years ago
- 73
- 0
Victoria and the Chastity Guard MK III
- 2 years ago
- 85
- 0
