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My first time.
#1
I want to share with you my first real time experience as a CD. I have been dressing since I was a teen, started with my mother's and sisters clothing, just had an attraction to the feminine things. This had progressed over the years off and on till I started to acquire my own things in my 20's. I would dress in the house but that was the extent of it till I started going out at night dressed but would never get out of the vehicle.

Then about 15 years ago I had advanced to the point of dressing completely with the hair, makeup, nails and fully dressed. I would go out and drive around but got up enough nerve to get out of the car, at first at the gas station, late night at the post office, and just walking down the street at night. I have to say it was very exciting to be out completely dressed as a lady in my dresses and heels. I never had a bad experience while doing that.

The next level of my dressing came with the internet dating sites, chatting with men who said they liked ladies such as myself. Just chatting with men and talking about what might happen in a real meeting was a real turn on and had me wanting more. 

I finally decided to meet one of the guys i had been chatting with for a long time, and we made arrangements for meeting in person. I spent about two hours getting ready for the meeting, showering shaving my legs and doing my nails and makeup. We had decided i would get a room in a local motel and then call him with the location. I had checked in and after I was finally ready and completely dressed I made the call. I was more nervous than I had ever been in my life, but he said he would be there in about 15 minutes and I spent the whole time waiting wondering if I could go through with the whole thing. 

When the knock came at the door I just about died I was so nervous, but I opened the door and he came in. He took a look at me and told me how nice I looked, which made me feel a lot better. and asked if it was Ok if he showered before we went any further. I said fine and proceeded to sit on the bed waiting and thinking about how it would go when he came out of the bathroom. He finished his shower and came out with a towel wrapped around himself and joined me on the bed. We made some small talk and he started to take off the towel exposing himself to me. I reached down and started to feel his cock which was just about fully erect, I guess he liked what he saw. I stood up and asked him to unzip the dress I had on, and I took it off leaving me in a black full slip, black stockings, black garterbelt, bra, and my four inch heels.

I faced him and got down on my knees in front of him with my face inches away from his now erect cock which I wanted to feel in my mouth for the first time. I started to kiss and lick his erection and finally took it in my mouth doing my best to perform like the gurls I had seen on porn videos. I could tell I was doing something right by the sounds he was making and feeling his body tensing up. I stopped sucking and asked if he would like to take my virgin ass, to which he answered yes he would love to. We changed places with me on all fours on the bed with him behind me. I had lubed my ass and also lubed his cock. I told him it was my first time and he said he would be patient and gentle. I felt him press against me and wondered if I could take him inside me, but as he applied steady pressure I felt my ass give a little and him start to enter me. Once he had the head of his cock inside me he stopped for a few seconds and let me feel it and relax a little. Then he started to apply more pressure and I could feel him going deeper but it didn't hurt. Once he was all the way in he started to slowly stoke in and out which felt pretty good, and after a while he picked up the pace and was fucking me pretty hard and fast. It wasn't long till I heard him starting to moan and he had me by the hips pulling me back on his cock till finally I could tell he was cumming. He shot his load deep inside me and stayed inside me till his cock started to soften. When he pulled out I could feel his sperm running down my ass. I have to say at that time I felt like a real woman or at least how I thought they would feel. I really enjoyed the feeling of having a man make love to me and knew I would have to have more.

We laid on the bed for a little while, then he got up and got dressed, thanked me for a wonderful experience and asked if he could give me a kiss. I said sure, we kissed and he was gone. I could still feel his seed oozing out of my ass. We never were able to meet again but he was a great first time experience and it only made me want more.
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#2
Wow, Vicki, your story about your first time made me a bit horny as I envisioned myself in your place.  Thank you for sharing.  It took a few years for me to acknowledge that I felt like a woman inside.  This is a link to a JC forum post I made regarding my first time.  Your story inspired me to share it again.

https://janetscloset.com/forums/showthread.php?tid=4764
Heart 
Anne
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#3
Sounds like a wonderful experience! I love that feeling of cum oozing out of me and running down my ass...

Friday of this week I am scheduled to be feminized by my new Mistress and will have to please her and one of her friends...and at her command i have been in a chastity device since Monday. Iui have a video chat with her tonight where I will be allowed to remove it, shower clean the device and then re-install it. She wants to make sure I dont relieve myself while it's off. After friday night, I may find my femme side wanting to dress more! I'm excited to find out! Good luck with your journey!
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#4
(02-12-2020, 07:56 AM)Anne Wrote: Wow, Vicki, your story about your first time made me a bit horny as I envisioned myself in your place.  Thank you for sharing.  It took a few years for me to acknowledge that I felt like a woman inside.  This is a link to a JC forum post I made regarding my first time.  Your story inspired me to share it again.

https://janetscloset.com/forums/showthread.php?tid=4764


Thank you Anne, I can still remember that night like it was yesterday and it was the beginning of a wonderful journey as Vicki and feeling like a real woman. I still love the feeling of pleasing a man and having him treat me like a true lady.
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#5
loved hearing of your experience Vicki, was wishing it were me in your place.
Thanks for sharing

Hugs
Christie
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#6
i would love to feel this way someday, someone complement my outfit and kiss my red lipstick colored lips. knowing that you are wanted for whom you are now.
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#7
(02-11-2020, 09:48 AM)vickitvcd Wrote: I want to share with you my first real time experience as a CD. I have been dressing since I was a teen, started with my mother's and sisters clothing, just had an attraction to the feminine things. This had progressed over the years off and on till I started to acquire my own things in my 20's. I would dress in the house but that was the extent of it till I started going out at night dressed but would never get out of the vehicle.

Then about 15 years ago I had advanced to the point of dressing completely with the hair, makeup, nails and fully dressed. I would go out and drive around but got up enough nerve to get out of the car, at first at the gas station, late night at the post office, and just walking down the street at night. I have to say it was very exciting to be out completely dressed as a lady in my dresses and heels. I never had a bad experience while doing that.

The next level of my dressing came with the internet dating sites, chatting with men who said they liked ladies such as myself. Just chatting with men and talking about what might happen in a real meeting was a real turn on and had me wanting more. 

I finally decided to meet one of the guys i had been chatting with for a long time, and we made arrangements for meeting in person. I spent about two hours getting ready for the meeting, showering shaving my legs and doing my nails and makeup. We had decided i would get a room in a local motel and then call him with the location. I had checked in and after I was finally ready and completely dressed I made the call. I was more nervous than I had ever been in my life, but he said he would be there in about 15 minutes and I spent the whole time waiting wondering if I could go through with the whole thing. 

When the knock came at the door I just about died I was so nervous, but I opened the door and he came in. He took a look at me and told me how nice I looked, which made me feel a lot better. and asked if it was Ok if he showered before we went any further. I said fine and proceeded to sit on the bed waiting and thinking about how it would go when he came out of the bathroom. He finished his shower and came out with a towel wrapped around himself and joined me on the bed. We made some small talk and he started to take off the towel exposing himself to me. I reached down and started to feel his cock which was just about fully erect, I guess he liked what he saw. I stood up and asked him to unzip the dress I had on, and I took it off leaving me in a black full slip, black stockings, black garterbelt, bra, and my four inch heels.

I faced him and got down on my knees in front of him with my face inches away from his now erect cock which I wanted to feel in my mouth for the first time. I started to kiss and lick his erection and finally took it in my mouth doing my best to perform like the gurls I had seen on porn videos. I could tell I was doing something right by the sounds he was making and feeling his body tensing up. I stopped sucking and asked if he would like to take my virgin ass, to which he answered yes he would love to. We changed places with me on all fours on the bed with him behind me. I had lubed my ass and also lubed his cock. I told him it was my first time and he said he would be patient and gentle. I felt him press against me and wondered if I could take him inside me, but as he applied steady pressure I felt my ass give a little and him start to enter me. Once he had the head of his cock inside me he stopped for a few seconds and let me feel it and relax a little. Then he started to apply more pressure and I could feel him going deeper but it didn't hurt. Once he was all the way in he started to slowly stoke in and out which felt pretty good, and after a while he picked up the pace and was fucking me pretty hard and fast. It wasn't long till I heard him starting to moan and he had me by the hips pulling me back on his cock till finally I could tell he was cumming. He shot his load deep inside me and stayed inside me till his cock started to soften. When he pulled out I could feel his sperm running down my ass. I have to say at that time I felt like a real woman or at least how I thought they would feel. I really enjoyed the feeling of having a man make love to me and knew I would have to have more.

We laid on the bed for a little while, then he got up and got dressed, thanked me for a wonderful experience and asked if he could give me a kiss. I said sure, we kissed and he was gone. I could still feel his seed oozing out of my ass. We never were able to meet again but he was a great first time experience and it only made me want more.
Oh my Vicki...I am not sure I would have the courage that you had. It does sound exciting and things you described are things I have fantasized about. I have never had a chance to be with a man, and only have been seen by a female friend once.
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#8
(02-11-2020, 09:48 AM)vickitvcd Wrote: I want to share with you my first real time experience as a CD.

I faced him and got down on my knees in front of him with my face inches away from his now erect cock which I wanted to feel in my mouth for the first time. I started to kiss and lick his erection and finally took it in my mouth doing my best to perform like the gurls I had seen on porn videos. I could tell I was doing something right by the sounds he was making and feeling his body tensing up. I stopped sucking and asked if he would like to take my virgin ass, to which he answered yes he would love to. We changed places with me on all fours on the bed with him behind me. I had lubed my ass and also lubed his cock. I told him it was my first time and he said he would be patient and gentle. I felt him press against me and wondered if I could take him inside me, but as he applied steady pressure I felt my ass give a little and him start to enter me. Once he had the head of his cock inside me he stopped for a few seconds and let me feel it and relax a little. Then he started to apply more pressure and I could feel him going deeper but it didn't hurt. Once he was all the way in he started to slowly stoke in and out which felt pretty good, and after a while he picked up the pace and was fucking me pretty hard and fast. It wasn't long till I heard him starting to moan and he had me by the hips pulling me back on his cock till finally I could tell he was cumming. He shot his load deep inside me and stayed inside me till his cock started to soften. When he pulled out I could feel his sperm running down my ass. I have to say at that time I felt like a real woman or at least how I thought they would feel. I really enjoyed the feeling of having a man make love to me and knew I would have to have more.

We laid on the bed for a little while, then he got up and got dressed, thanked me for a wonderful experience and asked if he could give me a kiss. I said sure, we kissed and he was gone. I could still feel his seed oozing out of my ass. We never were able to meet again but he was a great first time experience and it only made me want more.

Oh Vicki, I'm so happy for you! A girl NEVER forgets her first time, and I can only hope that the other ladies on this forum can experience what you and I have!

To all the girls who haven't yet been with a man, all I can say is: choose the Man wisely, someone who will take his time and be gentle. At least it is time for him to be forceful!  It certainly changed my life and my outlook, and made me the woman I am today. Smile
Before you can love another, you HAVE to love yourself first
I aim to misbehave
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#9
Well even though I consider myself a lipstick lesbian, that was one hot story, and got going a bit! Great first time. First time's can be tough and bad one can put you off forever.
Thanks for sharing.
Amy
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#10
Nice story - I met a man at a bar once who was buying me drinks. One thing led to another, and it was great. Wound up at my hotel and he still did not know I was a guy. Didn’t matter. Once in my lingerie he was all over me. I loved it and so did he. Fun!
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