Work and Pleasure - ( Pre Lockdown)

Hi All
This is another one of my(s)exciting work trip experiences. I
have combined a few of my experiences into a sequence, but all these
events ( though not in order as they happened) are true.

So as it
happens I had to travel for a good whole week to 3 cities. I got my
travel tickets from the office. I boarded the early morning flight and
reached my destination. I checked into the hotel and freshened up and
went for the first of many meetings. Had a good meeting and closed the
contract. It was around 3PM . I called the office and shared the good
news. I was feeling lucky with a good start to the trip. I called up the
second client and they scheduled for the next morning, so with nothing
else to do the entire afternoon, I took a cab and went to the market
near my hotel to do some lingerie shopping. I paid the cab guy and
walked around looking for a lingerie shop with not many customers and
after walking around for 20 mins I found one.

The shop had many
lingerie sets on display in the window and being mid afternoon , there
were only the staff. One behind the main counter behind the display
window( the owner I guessed) and a mid twenties guy, both watching
something on their mobile screens. I took a deep breath and entered.
They both looked up and greeted me. I took a sip of water from my water
bottle and asked for a bra in my
size in D cups. The assistant got up and brought me a few. I liked one
and I asked if he had some of the fancy lace bra panty sets in my size
like the ones displayed in the window. He said sure, and showed me a
few. The last box he opened had a nice red bra and matching lace panty. I
chose that and then asked for a panty hose. I paid for the stuff and
went on looking for shops to buy some body lotion, condoms, smokes.
While buying the rest of the stuff I saw a liquor store and also bought
a bottle of whiskey.While waiting for a cab near a street market I saw a
guy selling some nice floral pattern skirts. I bought one with a nice
white sleeveless top. I was all excited to get dressed up enfemme and I quickly took a cab and reached my hotel.

I
went to my room and threw all the new stuff on my bed, went to the
bathroom and cleaned and lubed my hole, had a warm bath and applied
lotion on my body. I dried myself and came out and headed straight to
the bed and got out my new lingerie and dress. I wore the lace panty and
bra, padded the bra and then came the panty hose. I went to check
myself in the full length mirror in the dressing room and I get a tingle between my legs looking at the sexy gurl in the mirror wearing red lingerie. I came back to the bed and wore the top n skirt. To finish it all off I wore heels. I picked my pack of smokes and lit one up and walked to the mirror again to admire myself. I was already getting hard. I saw myself in the mirror and my dick wanted to just spring out of the panty.
I
was now so horny I just wanted a dick in me. I thought of seducing the
hotel staff but was scared, so dropped the idea. I went online and
checked the local ad listing for guys seeking guys/CDs. I called up a cpl
of guys and they sounded too eager and rustic. I prefer a guy who is
decent and can play for mutual fun and not money minded( as they are
mostly),I found an ad, the guy was in late twenties, fit guy with a
almost 7" tool ( as it said in his ad details). I called him and he was
quite decent to talk to and we discussed our preferences and he told me
he worked at a spa and could meet me at 9 after his shift. I gave him my
room number and we agreed to meet. Let's call him Rohit ( R)
It was
6 pm so I had a good three hours before he came. I started watching the
TV and dozed off. I woke up around 8 pm. I went to the bathroom and
freshened up, lubed up again, adjusted my boobie pads and dress. I
opened a beer from the mini bar and lit a smoke. I walked around the
room and the sound of heels on the floor made me feel like a gurl.
I finished my beer and opened another one. I was dancing to the tune of
some hindi movie songs on the telly when my phone rang. It was R, he
said he will be there in 15 mins. I got excited and nervous. I went and
lubed a bit again just so that I am ready for the fun. I sipped my beer
and lit a smoke. After a few minutes my phone rang, it was R. He said he
is outside my room door. I took a deep breath and walked to the door (
with the heels tapping the floor it made me feel so sexy ). I opened the
door and it was the same guy as in the pics on the ad. I  removed the
chain and said ' come in' and walked back to the sitting area to get my
smoke. He came in and he said ' sir called me for a massage ' , I turned
around and said' Yes dear , I did '.
' Oh I thought you are
a girl '  he said. ' I told you I like to dress up as a girl '. ' You
look pretty in the dress' he said. I took a drag from my smoke and
turned to go to the bathroom to adjust my dress and boobie pads and i told him " Why dont
you strip and be ready to massage me, I will be back in a minute". I
went in and adjusted my dress and pads and came out, Crushed my ciggie
and saw him standing near the bed in only his boxers and I could see a
semi hard on in them. He motioned me to lie on the bed. I lay on the
bed, he came close and put his hands on my side and made me turn over
face down on the bed.
He started pressing, massaging my calves
lightly and then a bit harder. It was quite relaxing. He worked his way
up to my thighs and gave them a good massage for 5 minutes. Then his
hands were on my buns, after a cpl
of minutes of pressing and squeezing my bums over the skirt he pulled
down my skirt and I was there with my ass in my lace panty and hose. He
started massaging in round motion over my bums and then he got out his
bottle of oil from his bag. " You will have to remove the leggings so I
can massage with oil
" he said. " Ok dear, why don't you remove it for me " I said. He
slowly slid down my panty hose and kept it on the bedside table. He then
spread some oil on my thighs and calves and with strong hands he
applied pressure and was massaging
my legs. Bit by bit his hands moved higher towards my bums and after a
few minutes he poured some oil on my bums and started massaging and
squeezing them. I let out a few soft moans and he got a signal I liked
it. He rubbed from the side to the top of my bums and then from the
centre to outside. I was getting horny. He put his fingers in the sides
of the panty and pulled it down all the way. He got up and sat on my
legs and poured some more oil and this time he put some oil between my
bums, the oil trickled down to my love hole. He again started massaging
my bums in circular motion and his thumbs down between my cheeks every
few motions. Suddenly his thumb pressed down on my hole and he tickled a
bit and put some pressure on the hole. I moaned softly as I was getting
horny and it felt soo good. " your bums are so soft " he said and squeezed my ass cheeks. ( I do have soft and smooth ass cheeks ) " Mmmmm yessss" is all i said before he pushed his thumb right down my hole. My own dick was getting harder. He took out his thumb and put a bit more oil and in went
his middle finger. A min of pumping with his middle finger and then
went in 2 fingers as deep as he could. I was clutching the pillow,
lifting my ass up and was moaning. He pumped for a few minutes and I was
dripping pre cum. Then he got up and asked me to remove my top.
I
got up and opened my top and I was again face down on the bed, all naked
except for my bra. I just wanted him to fuck me right then but, he just
opened the hooks of the braa from behind and poured some oil on my back
and massaged me. Every once a while his hand would go down to my bums
and he would finger me before moving back to my back and shoulders. He
put his fingers under the bra straps and wanted me to remove the bra,
but I told him I want to keep the bra on " Dont remove this, I am a gurl
right now " He then turned me on my back and started massage on my
thighs and belly. After doing that for a few minutes he poured a cpl of
drops of oil on. my navel and tickled me there, I got so horny with that
and my dick was soo
hard now. He got up and cleaned his oily hands with a towel and then
started squeezing my boobs ( not saying again and again that I was
wearing a bra with pads). I moved my hand to his tool and it was rock
hard about 6" long. I stroked him over his boxers and after a few
strokes he quickly got rid of his boxers to reveal a nice shaved clean
tool dripping pre cum.
He turned me over in doggy pose and in went
his 2 fingers again. I was so horny I was barely holding my moans. I
couldn't hold on any longer and I opened the bedside drawer and gave him
a condom from the pack. He opened the wrapper and I took the rubber
from him and rolled it on his beautiful tool.
He came behind me and slapped my bums a cpl
of times. He put his tool on my hole and teased me, and slapped my bums
again. Then he put the tip on the entrance and pushed. He was fully in,
with the first push. He held it in for a few seconds, his tool felt so
hot and hard. I was bent over and with one hand I was holding my right
boob. He started full long strokes, pulling out almost fully with each
stroke. I was dripping precum and it was smooth and long strokes for the
next 5 minutes.
Then he pulled out and made me lay on my back and
spread my legs by holding my ankles. He positioned his tool on my hole
and couldn't enter. I held his tool and positioned it, he pushed and was
in. My legs held wide apart and he started pumping. My boobs were
bouncing, I held my dick and I was almost about to explode, I let go my
dick and held my boobs. He was pumping me as fast he could.
He had some stamina, he pumped in full strokes for the next few minutes
and then he closed my legs and made me fold them with my knees on my
boobs and his tool deep in me. He started pumping again and was going soo
deep I couldn't stop moaning. " Shhh...don't make so much noise " he
said. I still couldn't stop moaning with his balls deep strokes though I
did so softly now. After a few minutes he pulled out and had some water
and gave me some too.
Now he made me doggy again, this time on the edge of the bed. He stood behind me and in went his rock hard dick. He was pumping me full strokes and his hip slapping
my ass cheeks. Smack..... he slapped my right ass cheek and then the
left. " Do it softly, it hurts a bit " I said. He did it again but
softer this time. I Was about to shoot my load and then his thrusts
became harder and faster. I could sense he is about to cum. He bent down
and held my boobs and pumped me fast. THen with one final deep thrust
he moaned and came deep in me ( in the rubber) and I shot my load all
over the towel on the bed.
We both lay down on the bed catching our
breath. After getting relaxed we got up, he started getting dressed and I
wore my panty lit a smoke. After he got dressed and was about to leave I
asked him if he can come again early morning before I leave for my work.
Sure, he said " will reach by 8 in the morning ".  Which was a bit late
as I had to get ready after the love session and have my breakfast and
travel almost an hour for my meeting. I asked him if he can come early
but he said he lives on the other side of town and wont be able to come early.
I agreed and he said he would try and make it earlier and give me a call as soon as he is about
to reach my hotel. He left and I called up my regular cab guy and asked
him to come in at about 9AM. Feeling satisfied after the humping I
changed into a normal t shirt and shorts, ordered food and had my dinner. I slept in gurl mode.

I
woke up around 7 and was excited to meet Rohit. I had a nice warm bath
and cleaned and lubed my hole. Adjusted my boobie pads and wore my top
and skirt with it. This time I left out the pantyhose and just wore my
heels. All ready, I checked the time and it was almost 8 and there was
no call from him. I got a bit impatient as I had to leave for my meeting
too and reach on time. It was almost 815 when he called and said he will
reach in 5 mins. I checked myself in the mirror and again applied a bit
of lube as we would not get much time for foreplay. As luck would have
it he called again and informed he is stuck in traffic due to road
repair work about a kilometer from the hotel. FInally there was a knock
on the door at 835. I peeped through the chain and saw it is Rohit. I let him in and he said " sorry got late due to traffic jam". " That's OK, why dont you strip and freshen up " I
said. He had some water, placed his oil bottle on the bedside and then
stripped. He went to the bathroom to freshen up and I lit a smoke and
lay on the bed facing my left. I had a few puffs of the ciggie and he
came out fully naked holding his clothes in his left hand. He saw me on
the bed and I saw his limp tool twitch and start to rise. He placed his
clothes on the sofa and came near me. He held my ankles and caressed my
legs all the way up to my bums. He started squeezing them and poking his
finger in my hole. I guess he realised I had already lubed cause he
didn't go for the oil bottle on the bedside. He slid down my panty and
fingered me and I was getting horny. I took a last drag of the ciggie
and crushed it out. As soon as I had done that he lay me on my back and spread my legs. HE wore a condom and came forward and positioned his tool and looked in to
my eyes. I closed my eyes and he pushed. What a feeling it was, a hard
cock going deep in my hole, I just held my boobs and squeezed them. He
did small strokes and in a minute he was fully in. Then he started his
full long strokes and man he was excited. He rammed me deep with a cpl
of strokes and I had to tell him not to do that. A few minutes of
pumping with legs spread wide, then he turned me over to my left facing
the sofa and the full length mirror, and he held my right ankle and put
it on his shoulder. We both looked at ourselves in the mirror and then
at each other.He made me remove my top. He smiled and pushed his dick
deep in me. I couldn't take my eyes off the mirror. It was like watching
a CD/tranny porn movie. I touched myself and I was soo hard. After another few minutes of pinding he turned me over in doggy. In went his rod. He was pumping long strokes and suddenly my phone rang. I checked it was
the cab driver, " I reach in 5 minutes sir" he said. Rohit suddenly
picked up pace while I was talking to the cab driver. "Ya. Ok. ...I will
come down..... in some time" I replied between gasps and moans. "
Should I come up to take the bags?" he asked , " No..not
right....now.....I ...am a bit.....busy ...right.....now" I replied. I
couldn't speak normally cause Rohit was humping me with fast long
strokes. " You seem sick, are you sure I should not come up ?" Now I was
too horny and wanted to get back to my fucking and anyway the cab guy
knew I like to CD so just to end the call " No...don't come up, my
friend is here and he is fucking me ......we are....having .....some
fun. ......" I said. " OK " he replied and disconnected. I turned and
looked at Rohit, he was smiling and pumping my ass, he suddenly slapped
my ass ( this time it was slow ) but it felt good. He held me by my
waist and his strokes became faster and deeper. I almost fell face down
on the bed twice. One last push and he rammed his tool deep and filled
the rubber with all his love juice.

He pulled out and went to
wash himself. I lay on the bed to relax a bit. HE came out and started
getting dressed. I was on the bed, my skirt up and my tool still hard. I
was lying only in bra and skirt I motioned
him to hand me a smoke from the pack on the sofa table. I lit up and he
got dressed. He got ready to go and just squeezed my ass and boobs
before saying bye. " Call me when you come back to town again " he said. " Sure will" I replied. He went and I finished my smoke and had another shower and got ready to go for my meetings.

Part II

( I have tried to put in details so You all can enjoy reading as being the character you want to be)

( you all can see it in my gallery ).

We
had our tea and drove on. It was late and so we decided to come back
the next day. We came back to the hotel, I went to my room and as soon
as I entered my room and removed my male clothes I just stood there
admiring the gurl
in the mirror. I did a bit of dancing and jerked off after all the
exciting fun. Next morning went for my meeting and had to leave for the
next town  for a day at the client construction site and come back to
this place again, so I made reservations on the train for an overnight
journey in 1st class and also told my hotel to hold my room as I would
be carrying only a light bag and would be coming back the next day. In
the evening I had a light dinner and packed my office stuff and a change
of clothes and of course for the travel I wore my gurlie stuff under my clothes. while
I was dressed and finishing off my ciggie before I wore my guy clothes
over the lingerie I was getting excited and I took some photos in some
naughty poses.
I reached the station and boarded my train. After
settling down I talked to the coach attendant  to arrange some cold
water for a cpl
of drinks before dinner. He was happy to oblige after I gave him a
generous tip and also came to know there are only 3 passengers in the
entire 1st class coach. I was alone in my cabin near the door and the
other two were at the other end. The train started and since I was alone
and after waiting for 20 mins for the ticket checker to come and he
didn't, I couldn't wait any longer and opened my bag and padded my bra. I
removed my jacket and hung it in the cabin closet. I was sitting there
in my jeans and tshirt over my padded bra and the panty n stockings
under my jeans. A few minutes later the ticket checker came and said
Hello. He said since there are only 3 passengers in this coach he came
in last and I was the last one he had to check. I had downloaded my
ticket on the phone and showed him my phone to check. I was a bit
nervous as my big boobs were very visible in the tight top and I could
see him peeking at me while checking my ticket. He wanted to zoom and
check details on the phone and somehow mistakenly scrolled to the next
image ( which was my pic in lingerie in a hot pose showing my face and
also my hard on ) and sure enough he scrolled more. Then I got more
nervous. He scrolled back and checked my ticket, asked for an id and
showed him one. I don't know why but he asked ' Are you travelling alone
?' , 'Yes' I said. He paused for a bit then said ' Are these your
pics?'. I was caught and I just said ' Yes' . He again paused for a bit
then asked ' hot pics. Do you always dress like this ?' ' Only when
alone ' I replied.
He gave back my phone and sat there checking his
papers and charts. I was thinking why isn't he going out and I was
scrolling my phone looking at my pics. Then after almost 10 mins he put
his charts in his bag and said ' Nice top you are wearing. Can I see
your pics once more ' , then I knew he was game for fun. ' Sure but
please don't tell anyone' I said and I handed him my phone and he was
scrolling through the pics. He was getting uncomfortable and moving in
his seat. He scrolled through the pics a few times then as I saw him
looking at them again and again, I opened my laptop and opened my
personal folder which had my pics in various dresses and slutty poses
with some videos of me dancing in lingerie. I got up and sat next to him
on the berth opposite me and said ' I have more pics here if you want
to see more '. He was happy to see more. He scrolled through the pics
and I could see a bulge forming between his legs. ' Which station do you
get off at night ?' I asked. ' I am here till the last station' he
replied. It had gotten dark and I was getting horny, so I said' You look
at the pics and I will have. smoke at the coach door and come '. He
just nodded. I closed the curtain and closed the door and went for a
smoke. I finished my smoke at the door and the attendant asked me when
he should get the chilled water he had kept for me. I told
to wait a bit. I went back towards my cabin and with the rocking of the
train the curtain had moved a bit and I could see the ticket checker
had his dick out ( nice 6,7 inches and rock hard.) he had a passenger
towel near him and was stroking his dick while looking at my pics. I
knocked on the door before entering and I saw him quickly get up and
tuck his dick back in his pants and he sat down and I entered. I took
the laptop from him and asked' Did you like the pics?' ' Very nice' he
replied. I kept the laptop on my berth and sat in front of him. ' I
should go now' he said. `` You are in the mood I can see ' touching his hard on ' You
can come back after dinner if you want to see me dressed live and take
care of this' I said. He was silent for a bit then said' Sure I will
come around 930 after food service is over 'Well I wasn't going to
complain and this was a fantasy of mine to do it with a uniformed guy.
I called the attendant to get my chilled water bottle and had a cpl
of pegs. I wore my full gurlie dress under my normal dress while
smoking and went to the door to have a smoke. It was almost time and I
was getting excited. I finished my smoke and went to the loo to clean
and lube my hole. I came out and noticed the attendant getting ready to
sleep, I went to my cabin and adjusted my boobie pads and dress. I
opened my pics folder and was checking myself in hot poses and was
getting horny. kept browsing and watching my dance videos and he still
didn't come. So I just had a small drink and decided to go out for
another smoke. I gulped down my drink and went to the door for another
smoke. I saw the attendant was fast asleep in his small cabin beside the
linen cabinet with the door closed. I opened the door and was halfway
through my smoke when the Ticket checker ( let's call him TT ) came in
from the next coach through the connecting doors. We looked at each
other and he motioned that he would wait for me in the cabin. It was
dark outside and I peeped from the door into the other coach and all the
lights were off. I took a deep breath and walked towards my cabin in
the coach, as soon as I was about to open the door the curtain moved a
bit and I saw the TT sitting there only in his boxers and watching my
pics on the laptop. That made me so excited to see the TT all horny for
me. I stood there watching him and an idea struck me. I moved away from
the door a bit and removed my outer male clothes quickly and folded them
and held them in my hands. I was now in the coach aisle dressed only in
my padded bra, panty and stockings. I adjusted my boobie pads and
without knocking I slid open the cabin door and said 'Hi' . The TT
looked at me and was surprised and kept staring at me. I let him stare
for a while and then I placed my clothes on the upper berth and noticed
he was still ogling me and had his hand on his dick. Then I closed the
door and made sure the curtain was drawn fully so no one else could
peep. As soon as I had latched the door, he got up and came and hugged
me from behind. His hands massaging my navel and bums. I could feel his
hard on poking me from behind. He was kissing my back and his hands came
from behind up from my navel and squeezed my boobs. After a cpl
of minutes of foreplay, his hands reached the sides of my panty and
down it went. He was squeezing my bums and massaging my bums and I was
enjoying it. Suddenly..... smack.....he slapped my left bum. Even though
I liked it I motioned and told him not to do it as we were not alone in
the coach and others might hear. He said the other passengers are on
the other end of the coach and wont be able to hear over the noise( Indian trains do tend to rattle a lot when in motion ). ' Do
it slowly' I said and held his dick. It was so hot and hard. Another
min of play and slapping my ass, he bent me over the berth and
positioned his dick on my hole. I held it and he pushed. The lube and
the ass slapping had made my hole ready and in went
half his hard dick, It felt so good, I moaned a bit. He pushed again
and went in fully. I held my right boob and he held my left one. I was
also hard. He started pumping me in long strokes. He was pumping me
deep and with every stroke I could feel him squeezing my boobie pad. It
felt so good. Then again it happened, he slapped my left ass cheek, only
this time it was many slaps together with each stroke. My legs got
tired of standing and balancing while he was pumping, so I moved forward
and his dick came out of my hole. He was a bit surprised, but then he
realised and made get on the cabin bed in doggy pose. He climbed on the
bed behind me and then I realised he wasn't wearing a condom. I quickly
got one from my bag and gave him,
which he rolled on his super hard dick in no time. Then he again got on
the bed behind me and was fully in deep. His strokes were now faster
and his balls hit my ass. He had some stamina and rammed me deep with
each stroke. His deep strokes were making me so horny I was so hard. He
pumped mein doggy for a mins more and then his thrusts became harder and
deeper and I realised he was on the verge of cumming. Then he withdrew
almost fully and rammed me deep and moaned and thrust as deep as he
could and came deep in me filling the rubber with his juice and I also
came in ropes spraying it all on the bed sheet on the berth. He kept his
tool deep in me and fell on me and we lay there catching our breath.
Once we had calmed down he got up and cleaned his tool with the bed
sheet and wore his clothes. I was laying on the berth in nude except for
my padded bra and stockings. He got dressed and said he must go now as a
station is coming up and he has to do his rounds to check tickets of
new passengers boarding there. ' Thanks for so much fun. I will have a
smoke and then sleep'. I said. He buttoned up his shirt and just as he
was about to leave, I asked, ' Can I go out like this to smoke?' He was
silent for a bit, checked his watch and then said' The station is 15
mins away, let me check if anyone is there'. he went and was back in a min and told me I can come. ' You keep watch and tell me if anyone comes ' I
said. He just nodded. I went there dressed as I was in my bra and
stockings and stood in the door and smoked. He quietly stood there
keeping watch. I finished my smoke and thanked him. As I opened the
aisle door to go back to my cabin he slapped my ass and said ' your
destination is at 8AM, can I come before that ?'. I wasn't going to
refuse an offer for fun. ' Sure ' I replied. I went back to my cabin and
latched the door from inside and slept.
I slept like a log after
the hard romp. I was woken by knocking at my door. I woke up and since I
was dressed as I was last night after my session with the TT, I just
moved the curtain a bit to check who it was, and there he was again. I
checked the time and it was just a bit past 530AM. I adjusted my boobie
pads and wore my panty
and opened the door. ' Good morning. Can I come in ?' he asked. I let
him in and he was all over me right away. I asked him can you wait or
come a bit later as I wanted a smoke
and go to the loo. He said all are sleeping and I can smoke and he will
wait at the gate. We both went out but this time I wore a t shirt and jeans. I smoked and then went and did morning call
and cleaned and lubed up. I returned and he was gone. I went to my
cabin and got my male dress off. I left the door unlatched and lay on
the bed in my gurlie lingerie. He came about 5 mins later and locked the
door and closed the curtain.
We didn't have much time so this time he just removed his pants and he was already hard. I gave him a condom and he rolled it onto his hard on and this time he wanted me to ride cowgirl.
He lay on the berth and with his tool pointing straight up. I got up on
the berth and positioned his tool on my hole, he held my hips and I sat
down on it. His hard tool entered slowly and felt so good, touching me
deep. I started bouncing on his tool. He had his left hand on my boob
and with his right hand he stroked my dick. I did for a few mins and
then he pulled me to his chest and hugged me. Then he pumped me from
under in fast strokes. His hips slapping my bums. Again after a few
minutes he made in doggy and entered from behind. He was wearing his coat and held my hips and started pumping full speed. he
pumped so hard I fell face down on the berth and he was still in me. He
kept on pumping me. The deep long strokes made me moan. Then suddenly
he pulled out and turned me over and put my legs on his shoulders and
entered again. He was so hard and still doing deep thrusts. My boobies
were taking some serious shaking with his deep strokes. Another few
minutes of this and he rammed me as deep as he could and collapsed on
me. His hands on my padded bra squeezing them as hard as he could(
Anyone would have screamed from pain if he had squeezed so hard on the
boobs) I was on the verge on cumming my self
and once his cock stopped pulsing I rolled over and stroked my self and
with a just a few strokes again I shot my load on the bed sheet( That
was 2 bed sheets which would have my cum stains on them). He got dressed
and told me the arrival time for my destination. I also got dressed in
normal clothes and went for a smoke at the door. Had a smoke and came
back to my cabin and checked all my stuff and got ready to get off at my
station.
The train reached on time and I went to a nearby hotel and
had a shower and went to my client's work site. It was evening when I
returned and I had just about 3 hours to board the train for the return
journey. I dozed off for almost 40 mins. I freshened up had
a beer and food before leaving for the station. On the way I picked up a
quarter bottle of whiskey and a sandwich ( I did not like the train
food last night) and a fresh pack of condoms ( just in case).

I
reached the station and checked the arrival time of my train and
realised it was the same train as last evening going back. The train
arrived and I boarded my 1st class coach which was the last coach of the
entire train, only to find the same attendant there and this time I was
the lone passenger through the night. He greeted me and I nodded back. I
gave hima tip and settled my baggage in my coach and since I was the
lone passenger in the entire coach I chose the last cabin at the end of
the coach. I settled down and stood in the door watching the crowd on
the station before the train started. I saw the TT from last night
conversing with another TT 2 coach down from mine. He saw me and waved
and I waved back, I got excited at the thought that this will also be a
fun night on the train. I was checking my e mails on my phone and this time the other TT came in soon
as the train started. He was a guy in his mid forties named Mohan( as
it said on the name tag on his coat). He said Hi and asked for my
ticket. I was expecting the earlier TT but anyways, I showed him my
ticket on my mobile and he just scrolled through. I was surprised but
after scrolling a few times he handed back my phone and said 'Nice'. He
said Raj was busy checking the 2nd class passengers and would come
later. With the TT gone I was alone and I decided to change into gurly
mode.
I opened my bag and got out my gurlie stuff and got dressed as Sheila. This time it was full mode in padded bra, thong, stockings, palazzo and top. It was a cool evening and since I was alone and
the end of the train I went to the door and lit a smoke. I came back
and just wore my jacket over my top and rang the bell for the attendant(
let's call him Raj). He rushed to get the water and got his tip. I
opened my laptop and checked my mails and had a cpl
of drinks. An hour through the journey and cpl of drinks in me I was
feeling a bit tired. I went for a smoke at the door, I finished my smoke
and went to the loo to clean and lube up.
I came back and played a movie on my laptop and while watching I dozed off. i was
woken up again by knocking at my cabin door and I saw it was the TT
from last night ( His name was Ram) . He came in and said Hi. We just
sat there and chatted a bit and then I asked if he would accompany me to
the door for a smoke. It was around 10 PM and he asked to come to the
door as Sheila since everyone would be asleep now and we were at the end
of the train and he would keep watch. Well I didn't mind that. I asked
him to go out side
and check the coach and wait at the door. I removed my male clothing,
adjusted my pads under the top and put some lube on my hole. I picked up
my pack of smokes and went to the door as my cabin was at the end of
the coach. I lit the ciggie and was smoking and we were making small
talk. He came near me and started fondling my boobs and bums. I rubbed
him over his pants and thought of playing with him and said ' Why don't
you get naked and play with me ?' He said that might be a bit too much,
but I said ' come on , you want to have fun with me don't you?'He was
silent for a few seconds then he said' you also remove your top and
bottom' . We went in the coach and to my cabin and got undressed. He
came out fully naked and with a hard on and me only in lingerie. He came
to the door and I lit another ciggie. His hand
were all over me and his dick was hard again. His hands were squeezing
my bums and he pulled the sting of the thong to one side and rubbed my
hole with his middle finger. I was halfway through my ciggie and he kept
fingering me till I fished my smoke. I wanted his dick in me real bad
now. I finished the ciggie and close
the door and he literally pulled me to my cabin and locked the door and
I got a condom and he wore it so fast. He bent me over and one leg on
the berth and entered in one stroke and he was wild from the word go. He
was wild and pumping me hard long
strokes and in between slapping my ass once a while. He was crazy and
then he got more wild and then he groaned and filled the rubber with his
juice and slapped my ass hard. ' That hurt me!' I said. ' You made me
crazy tonite ' he said. ' You were crazy alright' I said. He quickly
started getting dressed and said ' My shift is in the other coaches
tonite. Thanks for the fun, will
try and come again before your stop'. He got dressed fast and went
away. I was still shaky after the wild pumping he had done. I got up
after a cpl
of mins and made the bed again and was dressed only in my lingerie. I
was tucking the bed sheet in the sides of the berth with my back to the
door when I heard a knock and my heart skipped a beat. I turned and saw
the curtain was half open on the door and it was Mohan ( the other TT).
My heart skipped another beat and he just slid open the door and came
in. Locked the door and closed the curtain. I just pulled the spare bed
sheet and covered my self with it. He said he was looking for Ram. ' Who is that and why you came in ?' pretending I don't know who Ram is.
He
said Ram is the TT of the other AC coach and he could not find him, so
he was looking in the 1st class coach as he saw Ram waving at me. ' No
one came here ' I said.
He just stood there for a min and asked '
Can I borrow a cigarette?', ' Sure ' I said. I got up to give him one
from my pack on the side table and the corner of the bed sheet got
caught under my foot as I stood up and the bed sheet slid down from me
and I was standing there only in my lingerie.
I looked at him, then
towards my pack of smokes and then back at him. He was just ogling at me
and he said ' you look as hot as in the pics on your phone '. Again I
skipped a beat, my mouth was getting dry. I was thinking I don't know
how long he must have been watching from the door. At this point I was
sure he was game for fun.SO I just picked up the bottle and a sip of
water and asked ' Can I smoke with you ?'. ' Yeah. OK ' he said.' Will you come like this? ' pointing to my dress. ' If you don't mind, but you
will have to keep a lookout for me.' I replied. 'OK , but keep the
bedsheet with you just in case 'he said and we both went out. We lit up
and made small talk. He told me his wife expired a cpl
of years back and k**s were in boarding school. I realised he was
desperate for fun. I went and stood close to him and rubbed him over his
pants. His tool started to grow. We finished our smokes and came back
to the cabin. He locked the door and made sure the curtain was fully
drawn. Then he hugged me and was kissing
my neck and shoulders. He made me lie on the bed and then got naked. He
was hard and had an average sized tool neatly shaved. He started
fondling my boobs and feeling me up from neck to toe. He then spread my
legs and was rubbing my hole with his finger like rubbing a clit. He was
making me horny. He got on top of the bed and top of me and spread my
legs. I realised he wants to enter me and I asked him to wear a condom. I
gave him one and he wore it and was back on top of me and then he
turned me on my right side and came behind me and spooned. He fingered
my hole a bit then put his tool on my hole entrance. ' Be
slow baby, don't be rough' I said. as soon as I had said it he pushed
and was in. My hole was ready after the romping by Ram and helped by the
lube. He was slow and gentle but doing full strokes. He came in 5 mins.

He lay there and hugged me. We both lay there naked for 5 mins then
I said ' Why don't you get dressed?' . ' I haven't done sex in a long
time. Let's do it again after I smoke' he replied.

He
got up, took a ciggie from my pack and went out for a smoke and he
didn't even bother to dress or cover up. I also decided to follow him as
I was ( in padded bra, thong, stockings) with my semi hard on which
could not be tucked under the tiny flower in front of the thong. He was
there in the door smoking and I joined him. The train slowed a bit to
pass a station on the middle track so we continued to smoke. It was a
very small station and had a few people on the platform and some of them
saw and pointed towards us and noticed two naked guys in the coach
door( one of them wearing a bra n stockings
but both had their dicks hanging for all to see ). We smoked and he
again had his hands on my bums and was squeezing them. I could see his
tool growing again. FInally we finished our ciggies and went back to the
cabin and no sooner had he latched the door, his hands were all over me
again. I gave him a fresh condom. This time it was doggy and he came
behind me and entered me. He just held my hips and was pumping non stop.
I was surprised he was hard again, 15 minutes after he had just cumm.
He was pumping non stop, and after doing doggy he turned me over and put
my left leg on his shoulder and entered again and was pumping hard with
one hand on my boob. With his other hand he was tickling my navel and I
couldn't stop moaning. He was ramming me deep with each thrust. Then he
pulled out and put a pillow under my bums and spread my legs wide and
entered again, His thrusts became fast and wild, I held my hard on and
stroked. He pumped for a few minutes and then pulled out and removed the
condom and sprayed all his cumm on my belly and I also came almost the
same time all over my belly and navel.
We both lay there and he
said' thanks, I haven't had sex in such a long time '. I wiped my belly
clean with the towel and we lay there and slept hugging.
I slept
deeply, tired after 3 sessions of fun together. I woke suddenly and felt
his finger rubbing my hole. I checked the time it was 5 AM. I sat up
and asked him to wait a bit, but he was in no mood to stop. He pushed
his finger deep and it hurt a bit. I gave him some lube and he put a lot
of it and put 3 fingers in. I started moaning. He wanted to kiss my
lips ( but I don't like that ) so I just got up and got in doggy.
He again had 3 fingers in me and pumped.I moaned, then after a cpl of
mins he got a fresh condom from the pack and then entered me. Held my
boobs from behind and pumped me till he came deep in my ass. Then he
pulled out, cleaned himself and got dressed, thanked me again and gave
me his number.
He went away and I lay there in my lingerie. I got up
after a while and went to the door to smoke with a hard on and again
while smoking in the door in my lingerie, the train passed a station and
many people saw me in a padded bra n rest naked. I went back in and the
train reached my station at 8AM on schedule.

I went back to my hotel and slept for a cpl
of hours before I went for my meetings. I was free in the afternoon so I
called up my cab guy and asked him if he could take me out for a long
drive.

He came in half an hour and we started. Had a few
incidents in the afternoon drive which went on till late night with some
fun incidents.( will post later )

Hope you all enjoy and let me know in the comments.