My First Meet

Story Info
The short story of my first meeting with another CD.
1.4k words
4.3
16.8k
3
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Rosecd
Rosecd
1 Followers

This is a true story about the first time that I had a meeting with another cross dresser.

It was a Saturday morning in the summer of this year, we had been sending messages for a few weeks online and had arranged to meet.

As a closet dresser I had to be careful as although my wife knows that I dress, (she does not approve), she does not know about my desire to meet up with other CD's.

Getting ready

So when the day came I was both excited and scared. I did my usual chores to get myself ready, washed and shaved my legs and clitty, also gave myself an enema so I was clean as possible inside and out, inserting a tampon to soak up the last of the fluid.

Next I had to select the clothes to wear. I chose a black suspender belt with a black satin thong and satin bra, next I got out a new pair of black stockings. I put on my ankle chain and suspender belt, unpacked the stockings and slowly rolled them up my legs, my hands were actually trembling with nerves and excitement. Next I put on my thong, making sure that everything was in place and finally my bra. I don't wear "falsies" so what is in my bra is mine.

Now what to wear, I decided on a short red skirt and white blouse and a pair of black 4" heels, finally I looked in the mirror and liked what I saw, so I was sure my date would too. By now it was 9:00am, my date was due about 9:30 so now is the worst part, waiting to see if my date turns up, or whether I am going to be let down as I have on previous occasions.

Meeting

My mobile rings, is he here or phoning to say he can't make it. I answer the phone, he is here and wants to know where to go, I direct him to my door and wait for the doorbell to ring, standing there dressed was as nerve racking as anything I have ever done, I have never opened the door as Rose before so this is going to be a day of firsts, I hope.

He has arrived and the bell rings and I open the door, he took one look at me and was suitably impressed. I bid him enter and in he came, setting his case on the floor as he entered. I offered him a cup of tea and made it for him. We chatted for a while whilst we drank out tea, then he went upstairs to change.

When I went up there after about ten minutes he was wearing a pair of white panties, blue stockings and a white suspender belt, with a pair of 3"heels and a blue skirt.

I cleared the bed and lay down. He joined me on the bed and started touching my legs, running his hands up them and commenting on how smooth they were. His hand touched my clit and sent a shock wave though my body, it was the first time another CD had touched me this way and it felt good. I returned the favour touching his legs and slowly working my way up them, when I got to his clitty I could not resist releasing it from its confines.

I now had a cock in my hand for the first time and it felt softer than mine. I now wanted to taste it, something I had not done since school, when I had a fling with another boy, so I slowly put it in my mouth and started to suck on it. It tasted clean and nice something I had not expected, it soon started to get harder with my administrations and I tried to get as much in my mouth as I could.

He was not a very large man about six or so inches, so I managed to get most of it in without gagging, by now he had started to suck me as well. He had met people before, so was much more experienced than me, and it showed. His hands were playing with my pussy and getting me well worked up, and I must admit to fingering his pussy as well.

I took a short rest from my sucking duties to play with his nipples, kiss and suck them and even gently bite them, which received little groans of pleasure from him. I wanted to taste him again so I made my way back to his clitty, kissing his body on the way down. I gently eased him back into my mouth, taking him as deep as I could but now he wanted more, his hands where on the back of my head and were pushing him deeper into my mouth, he was fucking my face, and I was loving it.

I think it was at this point that I realised that I did not want to fuck him, but I wanted him to fuck me, I now know that I am a bottom and have little interest in fucking a CD (at the moment, but that could change with time).

After about ten minutes or so of me being face fucked, I wanted him in me, I wanted that cock in my, up till now virgin (toys don't count), man pussy. I asked him if he wanted to fuck me, you can guess the answer and I passed him a condom which I had by the bed. As he fitted the condom I applied lube to my pussy, rolled onto my back and raised my legs sliding towards the edge of the bed.

He got between my legs and for the first time I felt a clitty touch my pussy, as he rubbed himself against me, probing me, he found my eager pussy and started to push. I felt him start to enter me, not the pain that I had expected (possibly due to the use of dildo's and but plugs) but a nice full feeling, getting fuller the more he entered me.

I'm in heaven now as he thrusts deeper into me I thrust towards him, riding him, wanting more, but alas it was not to be, he only lasted for about a minute before declaring he was coming, before I could say anything he came into the condom, not what I wanted him to do, I wanted to taste his seamen I wanted it in my mouth. Alas he withdrew and went to clean up, something I would have willingly done for him.

When he returned I was lying on the bed, playing with my own semi-hard clitty, he went down on me, sucking me deep into his mouth and sucking for all he was worth. I took him into my mouth and could taste the remnants of his cum, it tasted salty and so nice, I wish he had cum in my mouth, so I could have a better taste, even swallow it, that is what I wanted him to do, that is why I had him in my mouth, trying to get him hard again, so he would fuck me again, but try as I might he would not harden, so after about twenty minutes we gave up and concentrated on me.

Now I like to have my nipples played with and pinched, one of the things that gets me off. So I got of the bed and went into the other bedroom, got my nipple clamps and asked him to put them on me. He looked a bit apprehensive so I told him not to be, as they were something I often used, so he started to pinch my nipples so they stood up and gently put on the clamps, I think, no I am sure, that I let out a little squeal s he let them pinch my nipples, the pain was more intense than I remember it being before, possibly because somebody else had put them on.

I played harder with my clit and told him to face fuck me, as I felt I was cumming I asked him to pull the string between the clamps and stretch my nipples, this had the desired effect, the combined pain of my nipples and the face fucking brought me to my climax.

When we had both cooled down we dressed and vowed to meet again.

Something we have yet to arrange....... but soon I hope

Rose

xxxxx

Rosecd
Rosecd
1 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
amylin456amylin456over 12 years ago

Very nice.. can relate to much of what you wrote..

erotic and sexyy !!!!!

toni49toni49over 12 years ago
nice

real nice stroy hope to read more from you

clearlakequeenclearlakequeenover 12 years ago
Funny!

I am also a bi married CD bottom and it seems there are more CD tops than supposedly "masculine" tops.

Good story!

Share this Story

story TAGS

Similar Stories

A Downtown Moment Greg finds an old friend willing to allow him to be Georgia.in Transgender & Crossdressers
My Ex Girlfriends Mom Randomly seeing an ex girlfriends mom can be a good thing!in Transgender & Crossdressers
Like Mother, Like Sissy A sissy learns he is a princess . . . and a sperm whore.in Transgender & Crossdressers
Magic Panties Ch. 01 A man awakes to find a surprise at his door.in Transgender & Crossdressers
They're My Sister's Wicked Ways! Chapter, Sissy brother put in a risky situation by sister.in Transgender & Crossdressers
More Stories