Its rarely I get an afternoon alone but dressing as a girl is always on my mind and when an opportunity looks like arising I start to make plans. I start by logging into some of the websites I use, making myself popular, maybe a few comments in the forums will tempt the curious, update my status.
It was Saturday evening when I realised Id be available for a good few hours on the Sunday afternoon.
Within minutes there's a guy about 30 miles away he's interested. I can see he doesn't meet often only got one verified meet showing on his profile. he's very keen and we start exchanging messages. The butterflies that start in my tummy such a reminder of the feelings I used to get so long ago .
Its Sunday morning, I'm trying to stay busy but in the background there are plans to make. The people around me that don't know Jill hopefully not aware how excited I am. They are due out at 11am, I'm hopefully meeting him at 12.30.
I'm surreptitiously checking my messages. He is telling me where to meet, asking me to wear tights and coloured panties. He doesn't care about the rest of my outfit.
The messaging has been going on since I woke at 8, its 10.30 and I get a simple 'sorry cant make it'
Now here is the thing, that's a bit of a relief. So much fun anticipating but sometimes the event is a lot of work and dangerous.
Know that feeling?
Its now 11 and everyone is going out to an event 40 miles away that finishes at 6.I know im going to be safe for a few hours.
I check the Fab website, no more messages. I get my clothes out anyway and start getting dressed. I'll have a photo session and play with my toys watch some porn. Its a summer day and I can wander around the garden.
I've worn the tights as asked, a pretty knee length skirt and black turtle neck top. I cant stop myself and within a half hour I'm fully dressed with light make up, jewelry I've tried a few wigs and settled with a short blond.
I log in to the computer to look at some porn, straightaway I see a message from a guy I've met previously. He is almost 20 miles away, he 'doesn't have a lot of time'.
Oh how lovely, when these sites work they are so good. I agree to meet him.
he messages ' I've only got between 2 and 3 this afternoon, will you suck me off in my car?' Oh how lovely, I know this is going to happen. I've half an hour before I need to set off.
I live up a single track road and am hiding this side of me from the neighbour's. I put the wig in a bag with my skirt and jewelry.
Its 24 degrees but a loose jumper hides my boobs.
My date has messaged the location, it's on the edge of an industrial estate. Google street view lets me check it out. it looks pretty well secluded even though the Streetview cameras found it.
This will be one of a very few times I have met anyone in daylight, so exciting. I set off. I don't meet anyone on the lane which is such a relief that as I carry on the drive I begin to feel so utterly free. I need to fully become Jill though. Soon I spot a layby which I pull into.
It's a bright sunny day, there is another car but I don't care what they can see. Off with the baggy jumper, on with a string of pearls, pearl bracelets, my wig which I brush out while looking in the rear view mirror. I touch up my red lipstick.
Finally off with my shoes and trousers.
Look at me sitting in just black tights my brightly coloured knickers visible through the dark mesh. Now I feel so very sexual. I struggle into my black leather skirt.
Time to gather myself. Getting dressed in the drivers seat is not ideal. Looking carefully at the other car parked 50 yards from me, I decide there is nothing to loose if I get out to straighten my skirt. Today is about having fun and getting myself as Jill into the wild.
The door opens, a lovely rush of warm air his my legs.
I step out of my car. the road is pretty busy but at first I don't look at the cars thundering by. Tugging the skirt around so the zip is squarely at the back, tuck my top into the waistband. I flick my hair off my face. adjust my pose, bottom out tits out head up girl. I giggled. This is my high.
The other cars around me pay no attention as I walk around my car.
Climbing back into the drivers seat it is time for the next part of todays adventure.
Checking messages, my lover has announced he is there. I reply 'ten minutes or less. XX'
I tell myself out loud I will be in a strangers car sucking his dick in ten minutes .
I check myself, 'drive carefully Jill'
The last mile is easy, I'm turning into the industrial estate, left at the first round about and on a few hundred yards to the junction where the road ends.
The car he described, a new SUV is parked, just out of sight.
I park, check my face in the mirror, OMG look at me I feel so pretty in my pink fog. Our cars face each other. I can see him. He is in the back seat, he waves.
'OH FUCK JILL , here we go'
So erotic to be climbing out of my car dressed a girl on a sunny afternoon knowing what is waiting for me. I drop my car key into my handbag, it's now lost amongst the tissues, condoms, lipsticks. I zip it up. I walk towards his car trying to remember to walk upright, wrists turned in, a little wiggle of my hips. I open the rear door, he is sat legs apart with his pants down to his ankles. I know he has been playing with himself as that lovely cock is standing to attention.
Those leather seats feel so good against my nylons. I know there not going to be a lot of time. He does ask how I am, I let him know how excited and turned on I am. We exchange a gentle kiss, he obviously doesn't want to take my lipstick home!
We had agreed there wasn't much time , I reached out and wrapped my hand around him, he gasped quietly.
I moved to whisper in his ear 'I've been looking forward to this moment. Can I begin sucking your lovely hard cock sir?'
'Go on Jill suck my cock'
I leaned over and kissed his shining glans. Oh dear I was so turned on, I let his cock enter my mouth and went down until I felt myself gag. I know he likes a slow wet blowjob ( he asked in the messages) I tried to hold still.
That didn't work. Our positioning was all wrong. My fresh lipstick was very evident on that wonderful cock as I sat up.
Getting onto my knees I was better placed to try again.
There we were now, him sat reclined in his nice car while a fully dressed transvestite sucked his cock. He knew he could cum in my mouth as we agreed that too. Isn't that just such sheer pleasure?
Maybe only a few minutes, he moved his hips and I detached.
'could you take a few pictures?'
and so at the risk of ruining the moment I set my camera up for him. He was good enough to take a few before switching to video. I now have a delightful video of me looking up at him with his big hard cock up to the neatly trimmed pubes against my nose. I have another lovely memory preserved as he tells me what a good girl I am.
Camera done with I carried on sucking him, letting him out of my mouth to lick my drool from his lovely smooth clean balls.
I think we had been together ten minutes when he declared he needed to come. ' sorry but I don't have much more time' he placed his hands either side of my face and within a few seconds using my head as a convenient receptacle; he came.
He tasted nice. Most of his spunk went directly down my throat, a firm jet, as he withdrew that glistening red streaked penis from my lips I managed to taste some of the delicious product of our game. not all men taste so good (and he smokes)
I have met this chap before and enjoy his polite patience. Having spunked his juice into me he was remained happy to chat for a few minutes. I was a giggling wreck, something in cum acts like a stimulant to the sissy in me.
I of course still high as a kite on sexual emotion was happy to walk gaily back to my car. He drove off. I stayed.
Sitting there dressed up knowing what I had just done just feels so wonderful.
I waited a while standing by my car, ecstatic.
The day wasn't over, I needed to get home.
oh How wonderful that feels, driving in daylight dressed and feeling strangely confident.
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