An encounter with a Crossdresser
Sex Stories - A Fantasy - 24 Nov 2025
I walk in and come across this beautiful tall sexy crossdresser with lovely long blonde hair that is down past her shoulders. It is captivating, and I freeze just looking at her beauty as I find I get a huge rush of adrenaline through my veins as she turns and I see that she notices me there.
She invitingly smiles at me, and the look in her eyes draws me to her. I cannot look away, and the excitement is just too much to ignore...
I am a married man though and this is complicated. I shouldn't, no... this is wrong. (I say in my head...), but I cannot stop looking at her and the opportunity is right there now to just take her as mine, my special girl. It is only for a short point in time and its right now or there may never be the time or chance again.
I warmly smile back and start to walk towards her... Before I get a chance to find my words, she says "Hello handsome man... What are you looking for? Are you waiting for someone?"
I without thinking said: "Yes... I in fact was looking for you, and I have found you in this moment in time. I would like to make that time stand still together forever, but least for a little while"
She reached out and took my hand and I found ourselves in a quiet and discreet private place.
I was close to her, and I just reached forward and touched her hair softly, feeling its soft texture falling through my fingers and I said: " You really are a beautiful woman". I took her hand and held it in mine close to me for a moment, looking at her as I noticed my heart was racing in my chest, feeling a huge rush of arousal coming over me.
I was there looking in her eyes still holding her hand, but didn't know if she wanted to kiss me or not... I know some CD's don't want kisses, touching, hugging or any of that stuff and just want to please the man, let him do what he wants and that is it...
It was a moment of hesitation for me... I decided to just take charge of it and took the chance. I looked into her eyes and kissed her lips gently, and then kissed her again. She didn't stop me, so I let go of my thoughts and it became quickly intense, passionate and steaming hot.
I realised how aroused I was getting. It was so intense I had to take my pants off because of my raging hard on..
I didn't even say anything, and she was already on her knees grabbing and taking my cock deep into her mouth... It was feeling so sensational, the best I could ever remember. I moaned and groaned as she took all 6+ inches deep inside her mouth... Fuck! I have to have this again... I remember why I was bisexual and liked this side of my sexuality so much and why i needed to accept the way I was.
The animal in side of me started to came to life, and I grabbed her skirt and without a thought, pulled it down to reveal her cock. I was keen to see her cock and see her standing there with her lovely long blond hair and the rest of her beauty.
I so wanted to taste her cock too, even just for a short time, but I hesitated... I admired it but did not take her cock in to my salivating mouth. I wasn't sure if I would regret not just doing it, but I got worried she would reject it. I was thinking I should have just asked in the first place what was okay and what was not..
I was raging hard now and I just wanted her... I knew she wanted a top and I wanted to feel inside of her, and not just her mouth. My cock throbbing at the though of entering inside of her me for the first time exploring her was making the adrenaline pump so hard I was shaking.
I knew now she was mine. I could have her anyway I wanted here and she was there waiting for me to enter her...
She wanted 'me' to be that man, to give her a gift of love right now that provides her the feminism she so desired deep down in her heart, and I could.
I am tall, big and am muscular man, but I treat her kindly and respectfully with tender love, affection and care, but I take her as mine and I cannot help but enjoy her body. I ponder if that is selfish of me, or if its the way this encounter was supposed to be.
I tell her she is fucking so hot and sexy, and she is driving me so fucking wild I can't help myself and I just want her more. I love her in that moment and I tell her I love her.
I take physical control and dominate over her body. I enter her and it is so amazing. It feels so right! It is warm and so inviting and it is just perfect like we were meant to be.
I started doggy style, and then once we warmed up, I took her onto her feet and we were standing whilst she was bent over leaning on something, it went so fucking deep she nearly screamed the first time I pushed it all the way inside of her.
We did it missionary style. I could see she was pre-cumming as I was inside of her... I leaned over her and passionately kissed her. She was amazed I could do this to her.
I was getting so worked up, I leaned back and held her legs in my arms and looked at her sexy face, her beautiful hair and her hard cock. I was in ore of her.
I felt like an animal right at that point, working up a momentum and before I knew it I was thrusting in lust and passion, feeling every movement inside of her that I realised I should slow it down and make this really last.
I keep on closing my eyes as I was inside of her and the feelings intensified every time I did it. She was now very relaxed loving me deep inside of her. I slowed it down for a while, taking my time to really explore her and take it all in.
She seemed to be getting really slippery inside. I don't know why, I did not add any further lube.. It just felt so amazing and sort of different I cannot explain... It was the best feeling I was having and I never wanted it to end with her.
I was sliding in and out of her, nearly all the way in, then out. Then I would push it in so deeply I touched and connected to her soul.
The connection was intense, unimaginable and so special between us.
It was so intimate but dominating at the same time, and words are hard to describe the feeling.
It was so special to me and to her, so special that nothing else in the world mattered at that moment. Two people bonding, so connected and close to one another. The rush through our veins is indescribable.
Suddenly, I find myself convulsing, shaking and moaning as my head tilts back, my eyes roll back and I push and thrust hard forward into my special girl.
I thrust and push more as I cum so hard. I cum and cum and it feels like it isn't stopping.
The intensity is so high as this huge energy shift is exchanged. I give my girl all her feminism with love, admiring her feeling that connection to her soul during that special moment in our lives where we crossed paths with one another. I can never forget this... I cherish it and forever will... I looked at her and she had cum all over my stomach and over herself...
It was so intense I actually missed it and was sad I did no see her cumming together with me... So rare, and I missed actually seeing it happen...
We are now a mess... I am sweaty and I am covered in all our love, but I am totally okay about it... I don't feel embarrassed or have any negative feelings at all. I loved it, and loved getting hot and dirty, sharing our love together, discreetly but with high value... I appreciated time with this special lady that I connected to in that moment.
I appreciated it, and love it all, having all of her over me was a lasting turn on, and especially so that I made a beautiful, tall sexy crossdresser feel so beautiful, valued, sexy and loved for.
We sadly now parted ways, but we now know of each other in this big world and where we can cross paths again one day...
She invitingly smiles at me, and the look in her eyes draws me to her. I cannot look away, and the excitement is just too much to ignore...
I am a married man though and this is complicated. I shouldn't, no... this is wrong. (I say in my head...), but I cannot stop looking at her and the opportunity is right there now to just take her as mine, my special girl. It is only for a short point in time and its right now or there may never be the time or chance again.
I warmly smile back and start to walk towards her... Before I get a chance to find my words, she says "Hello handsome man... What are you looking for? Are you waiting for someone?"
I without thinking said: "Yes... I in fact was looking for you, and I have found you in this moment in time. I would like to make that time stand still together forever, but least for a little while"
She reached out and took my hand and I found ourselves in a quiet and discreet private place.
I was close to her, and I just reached forward and touched her hair softly, feeling its soft texture falling through my fingers and I said: " You really are a beautiful woman". I took her hand and held it in mine close to me for a moment, looking at her as I noticed my heart was racing in my chest, feeling a huge rush of arousal coming over me.
I was there looking in her eyes still holding her hand, but didn't know if she wanted to kiss me or not... I know some CD's don't want kisses, touching, hugging or any of that stuff and just want to please the man, let him do what he wants and that is it...
It was a moment of hesitation for me... I decided to just take charge of it and took the chance. I looked into her eyes and kissed her lips gently, and then kissed her again. She didn't stop me, so I let go of my thoughts and it became quickly intense, passionate and steaming hot.
I realised how aroused I was getting. It was so intense I had to take my pants off because of my raging hard on..
I didn't even say anything, and she was already on her knees grabbing and taking my cock deep into her mouth... It was feeling so sensational, the best I could ever remember. I moaned and groaned as she took all 6+ inches deep inside her mouth... Fuck! I have to have this again... I remember why I was bisexual and liked this side of my sexuality so much and why i needed to accept the way I was.
The animal in side of me started to came to life, and I grabbed her skirt and without a thought, pulled it down to reveal her cock. I was keen to see her cock and see her standing there with her lovely long blond hair and the rest of her beauty.
I so wanted to taste her cock too, even just for a short time, but I hesitated... I admired it but did not take her cock in to my salivating mouth. I wasn't sure if I would regret not just doing it, but I got worried she would reject it. I was thinking I should have just asked in the first place what was okay and what was not..
I was raging hard now and I just wanted her... I knew she wanted a top and I wanted to feel inside of her, and not just her mouth. My cock throbbing at the though of entering inside of her me for the first time exploring her was making the adrenaline pump so hard I was shaking.
I knew now she was mine. I could have her anyway I wanted here and she was there waiting for me to enter her...
She wanted 'me' to be that man, to give her a gift of love right now that provides her the feminism she so desired deep down in her heart, and I could.
I am tall, big and am muscular man, but I treat her kindly and respectfully with tender love, affection and care, but I take her as mine and I cannot help but enjoy her body. I ponder if that is selfish of me, or if its the way this encounter was supposed to be.
I tell her she is fucking so hot and sexy, and she is driving me so fucking wild I can't help myself and I just want her more. I love her in that moment and I tell her I love her.
I take physical control and dominate over her body. I enter her and it is so amazing. It feels so right! It is warm and so inviting and it is just perfect like we were meant to be.
I started doggy style, and then once we warmed up, I took her onto her feet and we were standing whilst she was bent over leaning on something, it went so fucking deep she nearly screamed the first time I pushed it all the way inside of her.
We did it missionary style. I could see she was pre-cumming as I was inside of her... I leaned over her and passionately kissed her. She was amazed I could do this to her.
I was getting so worked up, I leaned back and held her legs in my arms and looked at her sexy face, her beautiful hair and her hard cock. I was in ore of her.
I felt like an animal right at that point, working up a momentum and before I knew it I was thrusting in lust and passion, feeling every movement inside of her that I realised I should slow it down and make this really last.
I keep on closing my eyes as I was inside of her and the feelings intensified every time I did it. She was now very relaxed loving me deep inside of her. I slowed it down for a while, taking my time to really explore her and take it all in.
She seemed to be getting really slippery inside. I don't know why, I did not add any further lube.. It just felt so amazing and sort of different I cannot explain... It was the best feeling I was having and I never wanted it to end with her.
I was sliding in and out of her, nearly all the way in, then out. Then I would push it in so deeply I touched and connected to her soul.
The connection was intense, unimaginable and so special between us.
It was so intimate but dominating at the same time, and words are hard to describe the feeling.
It was so special to me and to her, so special that nothing else in the world mattered at that moment. Two people bonding, so connected and close to one another. The rush through our veins is indescribable.
Suddenly, I find myself convulsing, shaking and moaning as my head tilts back, my eyes roll back and I push and thrust hard forward into my special girl.
I thrust and push more as I cum so hard. I cum and cum and it feels like it isn't stopping.
The intensity is so high as this huge energy shift is exchanged. I give my girl all her feminism with love, admiring her feeling that connection to her soul during that special moment in our lives where we crossed paths with one another. I can never forget this... I cherish it and forever will... I looked at her and she had cum all over my stomach and over herself...
It was so intense I actually missed it and was sad I did no see her cumming together with me... So rare, and I missed actually seeing it happen...
We are now a mess... I am sweaty and I am covered in all our love, but I am totally okay about it... I don't feel embarrassed or have any negative feelings at all. I loved it, and loved getting hot and dirty, sharing our love together, discreetly but with high value... I appreciated time with this special lady that I connected to in that moment.
I appreciated it, and love it all, having all of her over me was a lasting turn on, and especially so that I made a beautiful, tall sexy crossdresser feel so beautiful, valued, sexy and loved for.
We sadly now parted ways, but we now know of each other in this big world and where we can cross paths again one day...
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