Last Night's Wet Dream Pt. 01

Story Info
A crossdresser's journey to fulfilment.
869 words
4.26
5.2k
4

Part 1 of the 3 part series

Updated 08/28/2023
Created 08/26/2023
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I have been crossdressing for a number of years now on and off as lots of us do. As I get older, I find I want to enjoy the opportunity of playing with a lovely hard cock once more. Inevitably this leads to fantasising. This is last night's fantasy .......

Its Friday -- the end of a long working week and I know that as part of relaxing I will get dressed. Today I decide to indulge myself by dressing up in what I call my secretary look. Although I guess it might be a teacher look too. I fling my man clothes off at the end of the day and go for a long leisurely bath during which I ensure that I shave off any hair. I want to be as smooth as I can be all over.

Having dried myself I walk into the bedroom and open my girly wardrobe. I gaze at all the delicious clothes with longing and start to select those I will be wearing tonight. Black stockings, a black thong and matching lacy bra, a white blouse and a black skirt. I lay these on the bed and sit on a stool beside my dressing table. Make-up first I think and I reach for the make up bag and slowly start to transform myself. Applying the make up to my cheeks, mascara and eyeliner and last but not least a deliciously red lipstick. I then look at my wig collection and think I will be blonde tonight so I fasten that to my head. I inspect the results in the mirror and am very pleased with myself.

I start to put on the clothes. Stockings first gently rolling them up my legs, stepping into my thong and pulling it up and loving the felling as it slides into my bum crack. I put on the bra and then the white blouse. Lastly, I step into my skirt and zip it up. I look at myself in the mirror and am pleased with the result. I think I look hot. I find a pair of kitten heels to wear -- high heels I still need to work on wearing.

I walk down the stairs and pour myself a large glass of white wine and retire to the sofa to relax. I have not had the courage to go out dressed before but tonight is a warm dry night and it is dark so I think to myself lets be brave and try it. Let's go for a drive in the car and see what happens. I know I can get to the car without my neighbours seeing me so that relaxes me a little. Having decided that is the right move I go ahead and find myself sitting in my car ready to go. The anticipation and excitement of this new adventure means I can feel a hardening under my thong. I start the engine and drive off.

Where to go is the next question? I drive aimlessly for a time just enjoying the feeling of being out and about all dressed up. Eventually the excitement starts to get to me and I realise I need to stop to relieve my sexual excitement. I turn into what I think is an empty parking lot and stop the car looking around to ensure I am safely alone. Everything seems quite so I pull up my skirt up and move the thong to one side. I start to stroke my hardening cock. It feels so good and I feel so horny that I soon lose myself in pleasuring myself.

Suddenly there is a knock on the window. I start and hurriedly trying to hide my, by now, very hard cock. The knock comes again and I look up to see a woman standing by the car and looking in. She gestures to me to wind the window down which I do with some trepidation. She looks at me and says: you look very pretty and I love what I have just seen between your legs. I smile but am afraid where this might be going so say I need to go now. She replies don't go yet I have a proposal for you.

I listen as she tells me that her husband is sitting in the car over there and points to a car I had missed when I looked around earlier. It was hidden in the far corner of the car park. She then says that like me he likes to get dressed and she helps him do this. He loves the feel of women's clothes and would like to take the next step of meeting another dresser to see where it might lead. He thinks he has bisexual feelings. She then says that the thought of him sucking on a hard cock fills her with a deep longing for it to come true. I nod and say that I would love to play with a hard cock but haven't done so for a long time.

Please come and meet him and lets chat, she says. I think hard -- this is more than I expected. Do I go with her to meet her husband?

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4 Comments
KatiwantsKatiwants8 months ago

Mmmmmmmmm mmmmmmmmm very good start!! I hope there will be more!!!

AnonymousAnonymous8 months ago

A good beginning.

Blackbear7Blackbear78 months ago

Nice little teaser. Does get the mind going as to what will he do. Nice to see how part 2 comes out....

AnonymousAnonymous8 months ago

Please finish the story I would love to hear what comes next

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