tagTranssexuals & CrossdressersA Fantasy in Pantyhose

A Fantasy in Pantyhose


I always go out to the same bar on Thursdays. The women are hot and long legged and they always wear pantyhose. Like usual, I dress in jeans, collared shirt and a jacket, deck shoes or dress shoes. Underneath, pantyhose. Always sheer to waist, no underwear and always nude. My jeans are long enough that no one can notice that I'm wearing nylons under my jeans. That Thursday was no different and I headed out after coming home from work and changing.

At the bar, I usually try to get a corner seat not far from the entrance, but usually along the corridor so I can see people come and go. I got my seat. It's a casual place, lots of business types after a long day, so many were still dressed for business. Suits and skirt with hose. My favourite combo.

Most of the people are friendly and just want to unwind from a rough day. That night was no different for me and I ordered up a rum coke to sit and sip slowly while watching the crowd. The crowd was good that night, a good mix of people. Some lovely ladies were in hose and I chatted absent mindedly with some of them.

I was there for about an hour and a half, and just finishing my second RC when a fellow came and sat beside me. I paid no attention, still just sitting there watching the crowd.

After about a minute he turned to me and in a quiet almost half whisper, "Filodoro or Hue?".

A little confused by his question, I asked what he was talking about.

"Nylons.", he said back to me and asks again, "Filodoro or Hue?".

I referenced some of the lovely ladies near by and told him I don't know. He then leaned in a little closer and with a bit of a sly grin said, "I meant you. What brand are you wearing?".

Panic. Instant panic. I quickly looked down and sure enough, some of my right ankle was showing. I didn't know how long it had been like that.

Turning a little red, I answered blithely "I still don't know what you're talking about.".

He put one hand on my shoulder and gently said "It's alright, I'm wearing too.".

I started to calm down a bit, though I didn't know why. It had clearly thrown me for a loop. Never had anyone, let alone a guy, notice that I was wearing pantyhose. And I always wear a proper flesh tone colour so as to not arouse any stares in case something happens to show.

I quickly tried to make my excuses. I gulped down the rest of my drink and made off to leave when he quietly suggested that we had a lot to talk about.

He mentioned that he had seen me here before (which made sense because I'm pretty well a regular), and that he had noticed me in hosiery as well, but this was the first time he thought of coming over and talking to me.

I told him right then, "I'm not gay as far as I know, and I come here for the ladies.".

"I know" he said, mentioning that he too also liked the look of a long legged lady in hose.

"It is a good bar for that." I agreed.

Ah what the hell, why not talk for a bit. And we did so about everything and nothing for about 20 minutes.

Then it came. He suggested that we go up to his apartment. He motioned up and to the left a little.

"I live in the next building just upstairs" he said.

"Do I or don't I?" I thought. Here I was, talking to a stranger who knows my secret, and invites me up to his apartment to continue the talk. This was too weird, looking back at it.

He sweetens the deal by mentioning my favourite bourbon and saying he has a bottle. I was always a sucker for pantyhose and good bourbon, so why not take him up on the offer.

We got up and left the bar, heading right next door, just as he said. It's one of those funky new condos, kinda loft idea with 5 floors.

He opens the front door and he motions to the classy vintage style stair leading to the second floor. I ask if his apartment is on the second and he nods affirmatively.

I notice once we're on the second floor that there are only three doors for the corridor. He leads me to the third where we walk in to one of the most spacious apartments I've ever seen. He grins a bit and tells me that this is his dream pad.

I get the quick tour of the main floor and kitchen and I'm totally amazed. It was open concept. The kitchen living and dining were all one large room. Stainless appliances and an island for entertaining in the kitchen. There was a long soft skin black leather sofa facing the kitchen with two coffee tables on either side and large persian rug in front with two modern loungers facing about 6 feet from the couch.

We walked over to the couch and he motioned for me to have a seat.

"I'll be back in a minute with the drinks" he said, and disappeared behind the sofa to what looked like a bar area behind an Asian motif screen.

I looked around a bit and noticed the guy had taste and class. It really was a nice place. I was just looking to my right at the couch and admiring the leather when he came up from the left of the sofa and offered me my drink

My mouth just about dropped when I turned to him. I must have looked like I just saw a ghost. There he was, standing there, offering me my drink, and all he had on was a pair of sheer to waist wolfords, nearly black and sandal toe.

To top things off, he was sporting the largest erection I'd ever seen, tenting his pantyhose quite nicely.

He was a good looking man, I have to admit. About 6' 2", maybe 195lbs, trim with washboard abs, good rugged looks and chin and nice brown eyes.

There he was standing in front of me, his cock must have been at least 9", aimed straight at 10 o'clock and right at me. Perfect head with a large ridge and very gently curved up.

I think I was still dumbfounded when he handed me the drink, and I still don't remember drinking any, but the glass was half empty, when I finally recovered. He looked at me after a minute, still standing there in front and asked if I liked what I saw.

I said again "Like I said in the bar, that while you're damn good looking and fill your hose well, I'm into women.".

He smiled and said calmly "Look down".

I did. There was a nice bulge in my jeans and I only finally noticed it. It was getting harder too by the second.

I turned that shade or red again. You know, that shade of red which is all the rage in lipstick lately. "Hmmm... What's going on here?" I thought almost aloud.

My bulge was getting bigger by the second and here I was in a strange man's apartment with him standing right in front of me with a cock aimed right at me.

I made to get up. I didn't make it...

He put his large hand on my shoulder again and suggested I get comfortable.

"It must be getting tight in there" he said, flashing that grin at me again.

I mumbled something, but did not try to get up a second time. Instead I had another gulp of my drink and asked for another.

"Gladly" he said taking my glass and removing himself to the bar.

You know, in that instant, I could have gotten up and walked out, but I didn't. Strange...

Instead while he was fixing my second '4 finger' drink, I got out of all my clothes except the pantyhose, which in case you were wondering were Filodoro diva, and sat back down on that beautiful and comfortable couch, and I was completely hard.

He soon came back with my drink and instead of giving it to me, he just smiled and put it on the coffee table beside the couch.

My heart was racing now as he stood in front of me again and slowly took my face in his hands and guided me to his pantyhose covered cock. I had done this with women before. I've had my cock sucked through pantyhose and thoroughly enjoyed it. Now I was going to get a taste from the other side.

His cock was massive in front of my face and I instinctively brought my hands up to cup his cock and pinch the nylons around it.

I noticed though that I had no problem covering his whole cock with the nylon. He noticed my puzzlement and said that he wears a size larger if he can so that I could do exactly what I was currently doing.

His nylon covered cock felt so huge but so good in my hands as I started to gently stroke it. I move my hands down his shaft to his balls, gently caressing them as I then worked my way back to the head.

Though his nylons were barely black, because they were so sheer, I could make out the veins stretching the length of his cock and the nice swelling around the rim of the head.

I moved my mouth closer to his waiting cock and started touching the nylon clad tip with my tongue. It was slightly wet and a little salty, looking down at it I could tell why. There was precum soaking the end of the nylon. I could feel my own cock starting to precum as a result.

I started to move my tongue a little further down and then under his pulsing beast. I was now in a position to look up at his face, and I remember clearly him staring straight up, his hands on his pantyhose clad hips.

God this was so erotic. I've been in that position so many times, and here I was on the other end producing that reaction in someone else. I was so hot and turned on by this.

I slowly worked my tongue around his cock several times getting the nerve to wrap my mouth around it.

I got the nerve.

His cock was so big that I needed to move slow. I made sure not to bite down either, which was difficult as I'm not used to sucking cock. His cock felt so good in my mouth. The nylon was rubbing against my tongue now but I could taste fully his musky scent. His cock seemed to pulse in my mouth and I made sure to go slow and sure.

I must of been doing a good job because I could feel him quiver a bit, but to this day I can't be 100% sure. I kept pleasuring him for what must have easily been about 15 minutes when he gently grabbed my hair and pull my mouth from that delicious cock. He leaned to my left to the coffee table, grabbed something and then stood in front of me again.

He was holding a bottle of KY. I flushed again. I shouldn't have, because by now I kinda figured what was happening.

He gently, he was a gentleman after all, took my hand and stood me up to face me the other way. He guided me down on the couch on my knees facing the back and I put my arms on the back of the couch to brace my self.

I could feel his hands caressing my pantyhose covered ass and that drove me all the more wilder. I wiggled a little as moved his hands across my ass and I turned to see him smile.

"Face forward" he said, "I have a surprise coming".

With that, he quickly tore a hole in the back of my pantyhose exactly where he needed one for access to my waiting fuck-hole.

I shivered a little and could feel the goose bumps starting. I did as he said and continued to face forward. I heard the bottle of lube opening and could hear the soft sound of the liquid being poured.

I felt a bit touch the crack between my cheeks and it was cold but arousing. His fingers slowly moved the jelly towards my hole and I could feel him press a finger in.

I moaned. Outloud I think, but I can't be sure.

He continued massaging my now willing hole and inserted another finger. I knew this was prep for getting my ass ready for his gorgeous monster cock, as I have had anal sex with more than my share of women.

After about 2 or three minutes of me blissfully enjoying the finger fuck, he pulled out his two fingers.

I could hear the bottle pouring again, but did not feel any of the liquid hitting my ass this time. It was time, I guess for me to have that huge beautifully shaped cock in me.

I could feel one of his lube covered hands on the small of my back as he bent me forward. I felt something brushing my crack gently, but it didn't feel quite right, so I turned briefly to look. He noticed me turn and the grin on his face told me to look down.

He still had his cock covered in his nylon!

He had lubed over the pantyhose and was going to assfuck me while still wearing his pantyhose!

I had only ever dreamed of doing that but had never tried it. For a pantyhose freak like me, I fantasized my nylon covered cock deep in a nice ass.

Now I was going to experience it.

Remember early how I mentioned that he wore his pantyhose a little larger to accommodate his cock? I now knew what the accommodation was for.

"God.. I want it so much more now.", I thought.

"Put that cock in me now.", I quietly told him.

I could feel the head of his huge cock breaking my barrier. He had guided his cock to the edge of my hole and then held my pantyhose covered ass cheeks apart enough so he could see his huge cock sliding into my hole.

When his cock's head did make it past the barrier, I jolted forward a bit and I felt my whole body quiver.

He held it there for a minute and asked if I was ok.

I could only say "fermumumshhhmmm" or some such nonsense and nod my head.

He chuckled a little and then continued to slowly push his nylon covered manhood into me. The feeling and pressure were unbelievable.

I was trembling as his cock made it's way ever so slowly inside me. I could feel my own cock pulse as he moved. I usually only felt that when I was cumming, but I was so overcome with the feeling of his cock inside me, it must have been a mini orgasm.

"Am I having an internal orgasm?", I thought. It must have been.

I groaned out loud and started to arch my back as well as any female pornstar could.

I could feel his cock throbbing inside my ass now. He was deep and as I put my hand behind me to feel how close his crotch was to my still pantyhose covered ass, he was still only 2/3rds in and I felt full. I couldn't believe it and almost went into shock.

Scared a little now because of his size, I tried to lean forward a bit to slow his progress. I couldn't move forward. His powerful hands on my hips kept me from moving forward.

He still continued to inch into me as I softly sighed, "You're way too big for my ass.".

He gently replied, "be patient, beautiful. Wait and see.".

He continued to push and my head felt like it was sitting on the body of a bobble head doll. I was slowly, but constantly, moving it about, side to side. This was definitely from the pleasure and pressure that was building inside me.

He then just stopped. I couldn't feel him filling me further. This caused me I stopped moving as well. I turned my head to him and with a dopey look on my face asked why he stopped.

He just smiled and said, I'm all the way, sexy.".

Oh My Fucking God... I had just taken all that 9" python into me, filling me completely, yet here I was expecting more. What an anal slut I turned out to be.

I needed to feel that cock inside me move. It had to. I didn't want to lose that beautiful feeling that I'd just experienced.

I started to grind my hips gently into his pubic area and moaned in low tones with each rotation. I could feel his cock moving inside me again.

He added to my pleasure by pulling out and pushing in slowly and just a bit. That feeling was so incredible. His shaft was pushing on my love button and I could feel my own cock, still trapped by the nylon, spring back and forth in my pantyhose with each push movement.

I took both my hands, resting my chest on the back of the couch, and reached behind me for his hips. I caught a hold of his pantyhose covered hips and began to push and pull him in and out of me a little faster now.

I desperately needed more of that feeling and his giant cock was giving it to me in spades. The pantyhose covering his cock made for such a fantastic sensation.

He took the hint and started to really fuck me. I rocked back and forth with each stroke now. I was starting to move.

"Fuck me you god!", I gasped between moans. He obliged and picked up the pace.

After less than a minute, I was almost screaming with pleasure as his cock was moving in and out almost pounding me.

The stuff that was coming out of my mouth would have sent the Sunday school nuns packing.

"Fuck me in the ass hard now daddy!!!", I shouted.

"Take my ass and cum hard!!", I demanded again.

It just felt so good and his rhythm was so perfect with mine. My ass would come back to him and his cock would push deep and I could hear his pelvis slap on my ass.

I was in heaven and I could feel my own cock getting ready to explode. I hadn't even had to touch myself. I was going to burst and I knew I was going to cum.

I yelled at him, "Deeper! Fuck me deeper!!! I'm cumming! I need to feel you in me when I cum!!!".

His hands were holding on to me for dear life when I started to feel the difference I was looking for, demanding of him.

He started to groan and shudder.

"I'm gonna cum in your slutty ass!!! Grind me you whore!!!", he demanded of me.

That did it for me. I lost it.

I yelled "YESSS!!!! Ohh god oh god oh god!!! Cream in me now!! Fuckin fill me DADDYYY!".

I pushed against him so hard and he grunted like a rutting animal as his cock pushed beyond reason.

"AAAAAHHHHHHHH!!!" I screamed and came hard right there.

I filled my pantyhose to the hilt with my cum.

He came too, and I could feel his warm cum with his last shuddering strokes, fill me.

"My god...", I thought. I never knew it could feel so good.

He just kept cumming and pushing into me. I could feel some of the cum escaping my hole so with what little sense and energy I had left I reached behind and got a finger of it. It tasted so good. It was salty but it made me finish feeling satisfied.

I could feel him finishing and he breathlessly flopped on my back, his breath on my neck, his warm chest heaving against me, his beautiful pantyhose covered crotch caressing my own pantyhose covered ass.

We lay down on the couch, spooning, with him still inside me. I held him tightly against me. I didn't want him to slide out yet. He moaned softly and curled his arms around me. Both of us still had our pantyhose on. A perfect finish.

Report Story

byjonezn4ph© 14 comments/ 60609 views/ 38 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartChenH, nickinph and 36 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Riki1942r07/27/17


Pantyhose are a life long fetish for me too. I use to put them on and play with myself before I ever knew about sex. You should try something that I found called Mantyhose. They are all sheer and havemore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 14 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: