A Hand in My Panties

Story Info
A crossdressing bi virgin's 1st time.
1.2k words
4.4
35.5k
16

Part 1 of the 2 part series

Updated 06/09/2023
Created 06/23/2019
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As a middle aged man, and seemingly like many others I had developed an increasingly strong bi curious urge to the point where the need to fulfill the fantasy of being with a man whilst combining this with an even longer passion for dressing in pretty lingerie had taken me to the stage where I was actively looking for someone to take me on the journey.

After explore months of searching, and many skype conversations that led to frustrating dead ends it looked like it might be about to come true.

I was married and my passion for wearing panties and dressing had, by necessity, been a long held secret that I had to be so careful to maintain this. And whilst I tried to kick the urge it always crept back up on me up and left me dying to fulfill the fantasy, even if it was just once.

He had to be patient and understanding and accept that for the first time I may not go very far if the nerves took over. I wanted a man who would understand and let me transform myself so that I could passionately and discretely explore my feminine side and reveal the pretty cotton panties ready for his pleasure.

As I got into my car I could hardly believe it was finally going to happen. Weeks of messaging had resulted in the final message. "I'll be in the airport hotel on the 17th." He messaged me on the day to confirm it was room 270 and to be there for 7pm.

I'd been shopping that morning and felt like a naughty schoolboy as i went into several stores scouring the lingerie and ladies clothing departments until I was able to finalise my outfit and it was now in the bag on the car seat next to me.

I arrived, parked and wandered into reception with my bag thinking everyone knew where i was going. The lift arrived and just as the doors closed a very pretty blonde girl stepped in giving me a dazzling smile as I kept the door open for her. On another day her body and pretty smile would have been all I wanted, but not today. Today was different.

I stepped out onto the second floor and found the room. Hesitating for a moment as I questioned my sanity, I finally raised my hand and knocked. I heard some movement, the door opened and I was greeted with a friendly hello and a smile.

"Thanks for coming. I wasn't sure if you'd change your mind."

"I nearly did," I replied and blushed.

After some small talk he asked what I wanted to watch. He got his ipad out and i showed him to a site with nubile lesbian videos and we settled back to watch as they slowly undressed to their panties and bras and their moans grew louder.

I began to shuffle in the bed as I became aroused in spite of my nerves and it was then he suggested I might want to go to the bathroom and change. I nodded, barely able to speak and picked up my bag.

I shut the door and took and took a deep breath. My fantasy would finally become a reality and I undressed and emptied my bag of girly treasures.

My hands were shaking as I unwrapped the new packet of black lace top stockings and slowly rolled them up my legs taking care not to ladder them. Then I clipped on the black pink lace suspender belt and savoured the feeling of its tightness around my waist. Next was the pretty white lace and cotton bralet which i slipped on over my head, the smallest aa cup i could find to gently hold my own tiny mounds and that made me feel like a young girl wearing her first sexy little bra. Finally I took a breath and stepped into the soft cotton brazilian cute panties, white soft cotton and lace edged. Simple, pretty and innocent and I tucked my soft penis into them, savouring the way the fabric felt against my skin and how the soft thin fabric encased my bottom. Over this i put on a simple short cotton summer dress, baby blue with spaghetti shoulder straps so you could see the pretty thin straps of my bralet underneath.

i called out to see if he was ready and heard a yes and opened the door. He had turned down the lights and sat on the edge of the bed. The girls on the video were in the final throws of their mutual orgasms and their moans echoed around the room.

"Hi, " I whispered "I hope you like this". He nodded and held out his his hands inviting me to join him at the edge of the bed. He stood up and told me I looked amazing. I was shaking, but could feel my penis stiffening as he put his arms around me and pulled me towards him. He had changed into a dressing gown and I could see the fabric rising against the pressure of his erection and imagined what it look like and had to stop myself from touching it as I felt rooted to the spot in the moment.

So this was it. I gulped and whispered to him that i was ready, that I wanted him to be gentle and show me the pleaures a man could give me.

He wrapped me in his arms, hands roaming over and under my dress, probing, stroking, caressing me, his lips against my neck until his tongue probed against my lips and we began to passionately kiss.

I moaned, panting as I felt my panties getting wet with precum from my bulging cock and he lifted my dress smiling at the mess i was making in my panties. I felt his breath as he slowly slid a hand up my stockinged thigh and felt him touch the soft damp fabric.

"Please use me," I gasped and he slid the dress off me revealing my body. His fingers ran over the little cups of my bra and he smiled before reaching down to touch my now rock hard 6 inch slim penis, kissing the slick wet head. I nearly exploded right then, but he held me gently, slowly stroking me as I got harder and began to shake.

"Let me cum into my panties, I want to make a mess in them for you...please...please...oh god...its so good...l feel so naughty...let me cum...please...oh please...oh please...ooooohhhhhhh...I'm so close...oh yes...oh yes...ooooohhhhhhhh my god..."

His gentle strokes took me to the edge and I kissed him feverishly as his hand took me over the edge and I felt the first deep pulse in my panty covered balls and I erupted, Pulse after pulse of hot sticky semen soaked the thin cotton and spread over my tummy, some jets reaching and staining my bralet and I cried out in joy as the orgasm went on and on and my panties got wetter and wetter. Finally the joy ended and I lay there, spent and sticky, smiling at him seeing how big his cock was under his dressing gown.

"Thank you...that was amazing. What can I do for you?"

He opened his dressing gown and I gasped as 8 inches of hard penis sprand into view tipped with a dribble of precum telling me how excited he was in response to pleasuring me

He smiled, leaned forward and kissed me and took hold of my hand and I gasped realising what he wanted next from me...

There will be to follow so watch this space as my bedroom adventures continue.

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14 Comments
AnonymousAnonymousalmost 3 years ago

I have to disagree with anonymous, who thinks that the comments are as good as the story.

Whoever anonymous is, has a really different understanding about the way that a girl's vagina smells

I'm a girl who is appalled about the description that anonymous has about a girl's vagina

Yes it's true that it does have a oder, but calling it a cunt is demeaning and vulgar and I find it offensive

Just let anonymous keep wearing girl's panties and soiling them with his seman so that he can continue to be the little sissy who he is and think that his soiled panties smell like a girl's vagina, which is so far from the truth

He's probably never been with a girl, because if he has, he wouldn't call a girl's vagina such a vulgar name

My vagina never has a foul oder, even when it's that time of the month. I go to great lengths to make sure that it doesn't because I don't want to be offensive to anyone who gets near me

AnonymousAnonymousabout 3 years ago

I liked the story. I want to comment on one of the comments. The question was, Dose anyone else think that the smell of cum and a hint of urine smells like cunt?

Yes absolutely is my answer

These two things mixed together definitely smell like a cunt and yes I often think that my gurl pussy as my cunt and I use it like I'm a girl. There's no better feeling then having a cock shooting ribbons after ribbons of seman inside of me making me feel like I'm a sissy slut and having it dripping out of my gurl pussy into my panties, soiling them and making my panties smell like cunt.

Thank you anonymous for mentioning your comments on how you feel about the way that seman and urine smell like cunt

AnonymousAnonymousabout 3 years ago

The comments are as good as the story especially the one who asks if anyone thinks that stale seman smells like cunt. I've always thought that dried seman smells that way

I wear soiled panties,soiled with dried seman almost every day because I love the smell it makes

I think of myself as a feminine looking girl and being able to smell my soiled panties, makes me feel like I am the girl who I'm presenting myself as

AnonymousAnonymousabout 3 years ago

Great story. Can't stop reading and wanting to be able to let this happen to me. He's a sissy slut and I am a sissy slut like he is. He actually did it and I wish that I could. Nothing would satisfy me more than wearing panties that someone had cum in so I could smell the musky aroma of seman other than my own

I wonder if seman has a different scent? I've only been able to smell mine and long for being able to smell someone else's. It would be exciting to be wearing panties that someone had cum inside of

My cock gets hard just thinking about it

Being a sissy wearing a pair of soiled panties would be the ultimate way to have a orgaisam so the mess in my panties would be his and mine

I'd wear them all day long with the aroma of our dried seman which would make my cock stay hard everytime I could smell it

Thanks for the great story and giving me a idea of what I need to do

I'm going to start looking for someone who would want to cum in my panties and let me enjoy my fantasy

AnonymousAnonymousabout 3 years ago

My secret fantasy is to be used like I'm a girl. I cum all over myself when I think about it. This story really got to me. Just the thought of wearing panties that someone had cum inside of so I could wear them soiled makes my clit hard. I call it my clit because it's hardly bigger than a clit. It's a poor excuse for a penis

I should have been born a girl. I am a girl in most every way except that I don't have a vagina.

I can relate to the man in the story because I have the same feelings as he does about wanting to be a sissy for a man. I could feel the excitement in the way he was thinking and looking forward to finally acting on his fantasy. I could feel the anticipation of what he was going to be doing and the resistance of how he almost turned around without meeting with the unknown man. When he knocked on the door of the hotel room, I could almost see the wonderment in his eyes wondered what the man looked like on the other side of the door. When he came out of the bathroom wearing a dress and a pair of panties I imagined that it was me. When the unnamed man wrapped his arms around him and kissed him I came in my panties. I wanted to be him so bad so I could find out what it's like to be kissed by a man. That's one of my secret fantasies I've read this story so many times that I've lost track of how many orgasams I've had

This story has helped me a great deal into making me want to get over my fear of being just a crossdresser and make the attempt to find a man who I can be with

Thank you for writing this story

You don't know how much it means to me

AnonymousAnonymousabout 3 years ago

Please use me. These three words resonated in my brain. I closed my eyes and focused on those three words..

Please use me I thought. Pretend that I am a girl. Please use me as those I have a cunt. I want to be used like I'm a girl. Put my legs up to my shoulders and spend my legs as wide as you can, then put your cock on the entrance to my gurl pussy and push it inside of me while I'm crying and telling you that your hurting me. But don't stop. Push your cock deep inside of me and listen to me crying and screaming that your going to get me pregnant because I'm not on birth control..Please use me as a girl who has a cunt. Being used like that would make me feel like I'm a girl. I want to be a girl in every way

There's nothing I wouldn't do if I could be a girl

Please use me. Please Please use me. Make me into a girl Please.

AnonymousAnonymousabout 3 years ago

What really got me is when he told the man who he met in the hotel to use me. When I read those words I came in my panties. I was wearing a pair of pink bikini panties under a mini skirt with a padded bra size 32 A to give me the appearance of having breasts along with a short little blonde wig with makeup that makes me look like a ordinary girl but I secretly want to be a sissy slut. My cock was pumping serious amounts of seman into my panties as I continued reading the story Just the sheer thought of having a man put his hand under my skirt and into my panties, then stroke me into a orgaisam blows my mind. Then when he put my panties on and came in them I was coming again reading about it

Please Please continue writing about this hand in my panties. Panties are the most feminine thing that I can think about that only girls are supposed to wear. I love panties more than any other feminine attire that I have. Seeing the head of my cock sticking out from the waistband of my panties makes me feel so feminine and girly. It's extremely rare that there isn't a drop of pre cum oozing out of it when I'm wearing panties. It's like a girl's pussy than stays wet most of the time soaking the gusset of their panties with pussy juice

AnonymousAnonymousabout 3 years ago

This story only made me want to become a girl more than ever. Everything about this was just what I have always wanted to do, but circumstances have kept me from doing it. I've cum in my panties plenty of times but I haven't had someone else cum in them and let me wear them afterwards. I can just imagine the feeling of having someone's seman mixed with mine touching my cock. Having stale seman mixed with a few drops of urine would smell almost like a girl's pussy smells. That would be more than enough for me to make my gurl pussy available for a long stiff cock to penatrate me and take my virginity. I absolutely love the idea of having a penis inside of me and being able to smell my panties that smell like cunt.

It would confirm that I am a sissy slut and make me feel like I'm a real girl

Anybody think like I do?

I'm almost sure that there are many crossdressers who have thought about this

AnonymousAnonymousabout 3 years ago

Hot. My cock was so hard as I was reading it and it was leaking pre cum. I was wearing a light blue baby doll nighty with a pair of matching panties and a padded bra with my blonde shoulder length wig and in full makeup and when he was coming in his panties, I was coming in mine to making a sticky mess with the enormous amount of seman that was coating my entire cock area It made me feel so girley doing this and I want to be a girl so bad

I wish that I could find someone to wear my panties and cum in them then let me wear them so I could feel and smell his seman. I think that if I were to wear panties that someone had cum in that would be more than enough to make me cum in them to so our seman mixed world smell like cunt and I'd probably let him fuck me in my gurl pussy as the smell of my panties would make me feel like I was a girl who wants to have a cock inside of her gurl pussy

AnonymousAnonymousabout 3 years ago

Hot I couldn't stop myself from coming as he was coming in his panties, I was coming with him in mine

Maybe my fantasy of being with a man won't be just a fantasy after reading this. I've wanted to experience the feeling of having a penis in my ass and be fucked like I'm a girl. I can only imagine how the pain of losing my virginity and how I'll probably cry like a girl as I'm feeling the hard stiff cock entering my gurl pussy, but the best part will be when he comes inside of me so I can feel his cock exploding sending ribbons after ribbons of his seman deep inside of my colon

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