First Time with another Crossdresser
My first time with another cross-dresser.
A true story.
Until the advent of the internet it was a lonely existence being a cross dresser but all that changed of course and sites like Xhamster allowed us sissy dressers to contact each other. It was a complete revelation to me how many of us there were and corresponding with others like myself was wonderful.
I also started meeting up on line through Skype and found the experience glorious. To actually see and talk to other transvestites was very liberating but I had yet to meet up “in the flesh” with another CD dressed Au Femme.
Well, one day I was surfing through some videos and glimpsed a cross dresser with a beard! Well, I thought, there’s at least one more like me. I’ve been bearded for years and yes, I know it’s very odd.
Anyway, I sent “her” a message and we started chatting. We found we didn’t live that far apart and “she” could accommodate (you know that’s quite rare) She didn’t use Skype so jokingly said I’d have to come and visit instead. She agreed!!! Instant butterflies!!! Wow, was this really going to happen??
A visit was arranged for the following Saturday and I duly knocked on the door to be greeted by a quite normal middle aged man (of course, aren’t we all normal when in boy clothes?)
He invited me in and offered me a cuppa - so far so normal.
While we chatted it became clear that it was the first time in the flesh for him as well and he was equally as nervous about what was about to happen as I was. He had been dressing for years and in the closet from his wife but sadly she was now in residential care so he was free to indulge his hobby any time he liked.
After some time I suggested we change into femme attire and we agreed to do this in separate bedrooms. My heart was pounding as I climbed the stairs to unpack my bag and slip into my favourites – black stockings, eight strap sussies, padded bra and matching knickers, a satin full length slip and a cotton summer dress.
My heart was pounding even harder as I descended the stairs as Auntiedolly and walked into the lounge to find my companion (Jenny) in a very similar outfit. I had had this dream for years and now it was coming true. All my birthdays were coming at once.
We chatted some more and she showed me some of her favourites on XH and other sites.
It was me that made the first move and “accidently” brushed my hand across her thigh.
“Oh, sorry” I said.
“Don’t be” she said and returned the favour by sliding her hand under my dress to my stocking tops.
“ Mmm, that’s nice” I said and responded by leaning in and giving her a kiss on the cheek. This quickly turned into a full scale french kiss and as our tongues explored each other’s mouths her hand slid up to caress my now rigid clitty. My own hand was also up her dress by now feeling up her own erection.
She then suggested we move to somewhere more comfortable and we were soon laid out on her bed kissing and stroking each other. It wasn’t long before I felt my knickers being pulled down and her hand stroking my newly released member. I, of course, returned the favour by sliding her panties down and caressing her most intimate parts.
The next move was pretty inevitable of course as I leaned over to take her in my mouth. She lay back with a satisfied sigh as I slowly licked and sucked her while fondling her balls. After some minutes she told me she was about to cum but I didn’t pull away, preferring to take her cum in my mouth as a proper slut should.
It felt so natural and I realised this was something I should have been doing all my life. As her spunk shot into my mouth I was in heaven as I quickly swallowed her seed.
After I had licked her clean she pushed me down and returned the favour as she sucked me off in an embarrassingly short time. I was so horny it took no time at all and was the first time I had been sucked off to completion by anyone.
After we had both recovered a little we went back downstairs for refreshments and talked about our experiences of cross dressing over the years. Our stories were very similar as we had both started very early but then got married and had to go into the closet. We both still dressed when we could and of course she was now able to indulge her passion at any time. She often spent days on end dressed Au Femme and at night as well dressed in a lovely satin nightie. This was the first time being dressed with another CD however.
She mentioned that her wife had been partial to BDSM throughout her marriage and asked me if it was something I might be interested in. To be honest I’d never given it any thought but was in the mood to try anything that day so Jenny disappeared off upstairs to transform herself into Madame Jenny. While I sat and wondered what she had in store for me. I suspected by bottom was in for some punishment if nothing else.
Madame came back down dressed in all black leather and straight away it was clear that I was to obey her every command. She made me bend over a coffee table and secured my wrists and ankles to the legs with lengths of rope. I was genuinely unable to escape and apprehensive about what was about to happen.
She started gently by lifting my skirt and slip and caressing my bottom before giving me a few playful slaps. The next was a leather multiple thong whip which she used more and more vigorously until it was really beginning to sting. At this point I noticed my clitty was once again stiffening and I heard myself thanking Madame at each stroke and asking for more. All these years and I suddenly find I like this. The last time I had my bottom beaten was at school!
Madame was now pulling my knickers down and after more bottom fondling she moved on to a leather strap which produced quite a lot more pain but was still manageable and strangely pleasurable. It was only when she gave me a stroke with a cane that I asked her to stop. My bottom was now hot and throbbing as Jenny released me from my bonds and I fell into her arms on the sofa deep kissing her lovely mouth which had recently been full of my cum and was soon to be again very shortly.
That day was the start of a wonderful friendship and the start of further adventures in the gorgeous world of cross-dressing. If only I had known decades ago.
A true story.
Until the advent of the internet it was a lonely existence being a cross dresser but all that changed of course and sites like Xhamster allowed us sissy dressers to contact each other. It was a complete revelation to me how many of us there were and corresponding with others like myself was wonderful.
I also started meeting up on line through Skype and found the experience glorious. To actually see and talk to other transvestites was very liberating but I had yet to meet up “in the flesh” with another CD dressed Au Femme.
Well, one day I was surfing through some videos and glimpsed a cross dresser with a beard! Well, I thought, there’s at least one more like me. I’ve been bearded for years and yes, I know it’s very odd.
Anyway, I sent “her” a message and we started chatting. We found we didn’t live that far apart and “she” could accommodate (you know that’s quite rare) She didn’t use Skype so jokingly said I’d have to come and visit instead. She agreed!!! Instant butterflies!!! Wow, was this really going to happen??
A visit was arranged for the following Saturday and I duly knocked on the door to be greeted by a quite normal middle aged man (of course, aren’t we all normal when in boy clothes?)
He invited me in and offered me a cuppa - so far so normal.
While we chatted it became clear that it was the first time in the flesh for him as well and he was equally as nervous about what was about to happen as I was. He had been dressing for years and in the closet from his wife but sadly she was now in residential care so he was free to indulge his hobby any time he liked.
After some time I suggested we change into femme attire and we agreed to do this in separate bedrooms. My heart was pounding as I climbed the stairs to unpack my bag and slip into my favourites – black stockings, eight strap sussies, padded bra and matching knickers, a satin full length slip and a cotton summer dress.
My heart was pounding even harder as I descended the stairs as Auntiedolly and walked into the lounge to find my companion (Jenny) in a very similar outfit. I had had this dream for years and now it was coming true. All my birthdays were coming at once.
We chatted some more and she showed me some of her favourites on XH and other sites.
It was me that made the first move and “accidently” brushed my hand across her thigh.
“Oh, sorry” I said.
“Don’t be” she said and returned the favour by sliding her hand under my dress to my stocking tops.
“ Mmm, that’s nice” I said and responded by leaning in and giving her a kiss on the cheek. This quickly turned into a full scale french kiss and as our tongues explored each other’s mouths her hand slid up to caress my now rigid clitty. My own hand was also up her dress by now feeling up her own erection.
She then suggested we move to somewhere more comfortable and we were soon laid out on her bed kissing and stroking each other. It wasn’t long before I felt my knickers being pulled down and her hand stroking my newly released member. I, of course, returned the favour by sliding her panties down and caressing her most intimate parts.
The next move was pretty inevitable of course as I leaned over to take her in my mouth. She lay back with a satisfied sigh as I slowly licked and sucked her while fondling her balls. After some minutes she told me she was about to cum but I didn’t pull away, preferring to take her cum in my mouth as a proper slut should.
It felt so natural and I realised this was something I should have been doing all my life. As her spunk shot into my mouth I was in heaven as I quickly swallowed her seed.
After I had licked her clean she pushed me down and returned the favour as she sucked me off in an embarrassingly short time. I was so horny it took no time at all and was the first time I had been sucked off to completion by anyone.
After we had both recovered a little we went back downstairs for refreshments and talked about our experiences of cross dressing over the years. Our stories were very similar as we had both started very early but then got married and had to go into the closet. We both still dressed when we could and of course she was now able to indulge her passion at any time. She often spent days on end dressed Au Femme and at night as well dressed in a lovely satin nightie. This was the first time being dressed with another CD however.
She mentioned that her wife had been partial to BDSM throughout her marriage and asked me if it was something I might be interested in. To be honest I’d never given it any thought but was in the mood to try anything that day so Jenny disappeared off upstairs to transform herself into Madame Jenny. While I sat and wondered what she had in store for me. I suspected by bottom was in for some punishment if nothing else.
Madame came back down dressed in all black leather and straight away it was clear that I was to obey her every command. She made me bend over a coffee table and secured my wrists and ankles to the legs with lengths of rope. I was genuinely unable to escape and apprehensive about what was about to happen.
She started gently by lifting my skirt and slip and caressing my bottom before giving me a few playful slaps. The next was a leather multiple thong whip which she used more and more vigorously until it was really beginning to sting. At this point I noticed my clitty was once again stiffening and I heard myself thanking Madame at each stroke and asking for more. All these years and I suddenly find I like this. The last time I had my bottom beaten was at school!
Madame was now pulling my knickers down and after more bottom fondling she moved on to a leather strap which produced quite a lot more pain but was still manageable and strangely pleasurable. It was only when she gave me a stroke with a cane that I asked her to stop. My bottom was now hot and throbbing as Jenny released me from my bonds and I fell into her arms on the sofa deep kissing her lovely mouth which had recently been full of my cum and was soon to be again very shortly.
That day was the start of a wonderful friendship and the start of further adventures in the gorgeous world of cross-dressing. If only I had known decades ago.
13 days ago
