Written by jill_gossard
11 Jan 2009
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13 minute read
I was travelling on a journey to the southern most tip of England and decided as it’s a long drive id take the sleeper train. I was to spend an overnight in a hotel near Falmouth so decided to take my alter ego Jill with me in my bag so as to have a little gentle fun while in the confines of my hotel room.
It was past 11.30 in the evening the night train was standing silently at a platform on Paddington station in central London. The steward showed me to my berth. I was reminded how tiny a space the berth is and was relieved that since there was no other luggage I may be travelling alone. I stowed my bags and went to the dining car for a nightcap before bed. The train was leaving Paddington as I finished my glass and never forgetting the feminine items locked away waiting for me in the cabin decided to slip off to get some sleep before the train arrived some 7 hours later.
In the cabin I took the lower bed.
For those who don’t know the compartment has a drop down bunk for the upper bed , there is a basin about 6 inch diameter with a tiny pair of taps, there is no hanging space. With the beds in place there is very little standing room.
I removed my clothes and slid into the bed under the covers that are also only just big enough to reach the edges of the bunk even without a person under them.
I placed my bag at the foot of the bed so I could fondle Jills clothes, I started to fondle myself to.
Of course I started to get aroused and decided since I had the cabin to myself that I should slip into my nighty.
I still didn’t feel entirely comfortable that no one would come in so pulled the navy blue satin long length item from my bag and under the cover. Pulling it from my feet up and wriggling sensually within its silky folds, I slipped the straps over my shoulders. I gasped to myself in shear pleasure and relief. The journey from my office earlier in the evening to the station knowing I was carrying these items had built up to quite an uncontrollable desire. I fumbled again and brought out a pair of lace top stockings, and panties and dressed myself further. It felt so nice with the silky fabrics sliding against each other and my tingling flesh. It was warmer too than the single sheet and thin blanket.
I switched on my laptop and brought up some of the saved erotic stories I keep in a locked folder. I was reading the stories and softly rubbing myself, feeling sleep coming on I laid the laptop on the floor, I was about to fall to sleep.
Outside in the corridor there was a lot of noise. Earlier I had jumped at each click , slam, clatter or thump on the door as the various denizens of the night train went about their business, I was relaxed now and off my guard.
Thud, Crack! Click; the door burst open!
My pc was scraped across the floor by the opening door. I had a roommate.
“Ach sorry mate” said a slurred voice, loud and blunt “I’ve been in the bar, sorry to wake you, did I wake you? I’ve got some cans do you want one? Here!”
Pssht, he opened the can and thrust it down at me. I froze. The can shook, I could only see his legs. Dark blue, thin man made fabric, a business suit I guessed.
“Go on you’re awake now might as well.”
I took the can.
It was tricky to drink while keeping the covers over me. He leaned down to move my computer, but lifted it up to his bunk I got a glimpse of the man, short hair, ginger; sturdy not fat, with a clear complexion and obvious stubble, he looked tired and certainly red-faced with drink. I drank more of the strong lager, sitting up but huddled as best I could I was trying to drop the straps and get the feminine clothes out of sight.
“ Could I have that please?” I asked.
But he was silent. I knew he could see what I had been reading.
Blimey mate you’re a strange one. Is this what turns you on?
“…..as roger pumped into my girlish ass I imagined that yes I was really his girlfriend and couldn’t wait for the moment he gave me his love juice in my tight little pleasure hole…”
I saw the mans body start to bend and his red face loomed into view. “ Ohh my you are going to have fun girly boy. Whats your name then?”
“Jill” I said gruffly.
Whats that, you don’t sound like a girl, tell me again.
Jill I said softly.
Again like you mean it, he demanded in a little voice like he was taking to a child. I drank again on the can and felt an acholic rush and lisped, “ Jill”
That’s better do you want to be Jill for me, I think from what I am reading here that you probably do. Have you been with a man before Jill?
Good then you know what I want.
With that he stood facing me but with his elbws on the bunk above. I pulled the straps back over my shoulders and swept aside the blanket. My nighty was standing tent like in my lap. Yes I wanted this. I reached out and undid his thin leather belt and tugged down his zip. Then using both sets of fingers fumbled to undo the two buttons holding the waidtband of his trousers. They fell straight down to his ankles. There was his bulge 18 inches from my face he wasn’t hard but the great pack looked huge I reached out and held it and smoothed my hands over the course cotton . my finger tips took the waitband and pulled it towards me he lay like a sleeping snake on the balcony this formed.
I was uncomfortable so swung my legs off the bed. I had to keep my head low to avoid the upper bunk. With my feet either side of his I took down his pants and looked at his cock as it hung like a lonely horse inches from my face.
“go on then make me hard you girly slut.”
Wrapping my hand round the tick animal I started to milk him. The soft flesh responded well to my touch and began to grow. With a series of jerks he was fully erect and had become a frightening size. I have sucked a few men in my time as a girl and know what will fit at a glance. This looked ok in teeth clearance but it was long and I knew already that tomorrow I would have a sore throat!
I filled my mouth with its head and sucked and slobbered on it. As I worked I cuped and fondled the heavy ball sack. One hand always on his shaft to protect my tonsils.
He took my hands though and placed them on his hips. “ deep throat Jill, the girl in this story likes to do deep throat doesn’t she.” In the story he was reading on the bunk above the theme was similar to the situation I had found myself.
Caught with consequences.
“in the story cindy is fucked till she gags is that what you want Jill?”
“ooohh Haa aaahhh” I squeaked as closely as I could to the sound of a pre-orgasmic female “good girl”
he thrust into my mouth and I gagged but he held me onto it, I was choking it was frightening but he did let me off I gasped and blubed “please, I don’t like that” seconds later he piulled me back on “ I do though you sissy cock sucker” he fucked my throat and I reminded myself of the techniques I had read. I tried to swallow the cock head right down, that way my body s ok and the gag stops. I started to feel the reflex subside and could feel the cock in my nexk mushing up all my soft organs like a great big vagina taking a manly cock all the way.
I wanted him to come so it would all be over, I was hard myself and ready to come any second but the fear was holding me back a little.
“ I am too pissed to come” he sadi and pulled out of me.
Turn over I need something a bit tighter to get off.
He lifted the top bunk and strapped it into its day stowage position.
He saw me for the first time fully in my pretty lingerie.
“you don’t look much like a girl, have you not got any make up? And you are a bit flat chested as well.”
I have some other bits I wimpered.
With that I went to my bag and got out my makeup bag. I quickly put on some lipstaick and took the opportunity to get a condom and lube from the same bag.
I passed him the rubber.
That’s better what pretty lips you have, now turn round I don’t want to look at your face. The wrapper fell to the floor and I heard the snap ans he placed it in position on his still rigid cock. I reached around between my legs and applied some KY to my hole and rubbed it in, I wasn’t confident he cared if I was ready or not.
“nice , nice Jill get her ready for my Billy boy. Tell Billy what you want Jill”
“I want your cock Bill” I said in my most womanly husky voice.
“ you’ve had my cock already tell me where you want it this time”
“In my pussy Billy, my fucking lover, fuck me with your big manly cock”
“are you ready for it Jill, Its mighty big my cock, will it be too big for a girly like you?”
Probably will be but if you are gentle Ill stretch for you”
With that he rubbed the tip up and down my slit. the lubricant and the condom making it all feel slippery and ready. the tip passing again and again the soft yielding part that was my entrance, anfter several passes he stopped and beagn to push.
As always it hurt as my soft flesh resisted the quick change in diameter and then the ridge of the glans was past the tighest part and he was in me. Now he made short pushes in and out working the lubriacant and flesh together to inch into me.
Afet some 5 or even ten minutes of complete silence on both our parts he was fully in and I could feel his thighs on my pantied bottom ( he hadn’t removed my knickers)
Now Jill how does that feel, ever had such a big one”
Honestly no sir it’s a delight I lisped breathlessly”
He giggled. I heard another can open on the bunk above. He steadied himself.
Do you want a sip? The can waved infront of me but I was pressed into the hard mattress by his bulk, “no thank you sir” I lisped again sweetly although it was hard to be so demure being so full of cock I just wanted to grunt like a whore. I felt him move in me as he tipped his head back to drian the can.
I heard the can go down. He started to move his hips and his cock went deeper into me. I was relaing and it was wonderfill. He must have been in me for over ten minites now and I was ready to enjoy him.
His fucking started so slow as to be lightly pleasurable my hot inside was being burned by his hotter member fired as it was by his hot drunken blood. The cock felt rigid but softly covered. Its tip was touching something deep in me that was uncomfortable but gave pleasure at each touch.. biil started to hammer me know and I was shaking in reponse my whole body propelled like a girls dolly as he hammered my girlish bottom. He went into overdrive and was obviolsy trying to cum.
Grunting and slapping my bottom. Also fondling me all over. The hammering against that thing in side me caused me to come and it hurt the fliud came so hard from my skinney hard little cock.
I was fucked now and waves of release came over me. I wanted to collapse and enjoy the orgasm but Billy wouldn’t like that I had to carry on performing for him. I needed to get him to finish. I squirmed my bum, I backed to his thrusts. I was loosening off and so tried to clench to grip and give more friction to milk his very come.
URRGGHH. Take that Jill you whore! With a big thrust he locked into me and held my hips hard. I was pressed against the cold formica bulkhead and he spasmed.
And spasmed. And held me.
He shuddered and gave a final couple of humps then fell on top of me.
Within a minute he was shrinking out of me and when he stood up had left the full condom in me. He pulled my panties into place and covered my exposed stockingtops with the skirt of my night dress. His large hands smoothed down the nylon against my stockings.
Fucking hell sorry mate I wish I hadn’t done that, are you alright? I wasn’t too rough was I . I went to hug him but he pushed me off. Sorry, Im going off to sleep. No hard feelings but I feel bad now.
“its ok I understand really I do. No need to talk abny more. Night.
I pulled the thin blanket over me and slept in my nighty .
In the morening bill was gone.
There was the condom wrapper on the floor. I was still in my nighty. I checked and my laptop was still there. I looked at the story I was reading last night. There was bills mobile number. He had also typed the name of a hotel in Falmouth.
Not such a regret after all?
I felt my bottom, the condom was still threr although its contents had leaked and made my panties stiff. I felt such a slutty girl. I struggled to remove the smeared lipstick in the tiny sink and packed my girly stuff back in the bottom of my bag. The guard knocked to say we has d 10 minutes to go. I phioned the number.
“bill its jill thankyou for last night you made me such a happy girl”
Sorry mate cant talk ring back later if you like” I guessed he was with colleagues in the breakfast car. I will try again later.
My next call was to book a hotel room…….