tagTransgender & CrossdressersGender Bias Ch. 03

Gender Bias Ch. 03


I'll tell you, the good thing about wearing women's underwear is that it breathes, breathes more than jockeys that's for sure. Ok, so I did wear her little pink panties all day, I know I said I was going to take them off on the way to the construction site, but the truth is they just felt so damned good, I didn't want to. The fear of my co-workers catching me was very real, but I think that might have been what added a little excitement into it. I tell you, with that soft silky fabric caressing your cock all day, all you can think about is sex. Hammering nails into boards you are thinking about fucking, painting walls and you are thinking about fucking...hell even putting together a few pipes for the plumber, and you are thinking about fucking. I wondered if Sarah knew how crazy she was driving me, how hard I'd been all day. The stiffness of my crotch and the softness of the panties made me forget about how bad my ass still hurt from her dildo.

"Hey Steve-o, me, Frits, and Jake are gonna go for some beers after work, you wanna join?" Carl, wiping the sweat off of his forehead with the back of his hand, asked. Carl was standing beside me dripping, most everyone had stripped their shirts off in the afternoon heat, but I left mine on, knowing that it was the only thing concealing the waistband of the pink panties. Carl loomed over me, a giant in all his stature.


"Oh come on Steve-o, quit being such a pussy." Frits joined in, unsure of how close he actually was to telling the truth. All I could think about was just that, pussy, both mine and Sarah's. I wanted her so badly my cock ached.

"Maybe next time guys, I'm gonna meet some broad tonight."

"Oh yea...you go ahead" Carl assured, "you get some of that pussy."

"Hell yeah!" Frits clapped Carl on the shoulder, overjoyed.

And so I left the construction site, my cock thick against my leg, and headed straight to Sarah's apartment.

When I got there, Sarah answered the door in a partially see through pink nightgown, and it was all I could do to control myself, to not reach out and fuck her right there in the doorway. She motioned for me to follow her to her bedroom, and I did, closing the door behind me.

When I stepped into her bedroom I immediately noticed that her Mr. Monster dildo was gone from the dresser and the other, smaller dildo was also gone from the nightstand. My stomach dropped in a disappointment that I found hard to believe.

"What is that?" I asked noticing the curious chair in the middle of the room. The chair looked like a reversed recliner of sorts, but made of wood. It looked like the person who sat on it would have to lean forward.

"Why are you always asking so many god damned questions?" She demanded. "Now on to important stuff, did you wear my fucking panties all day?"

"Yes, I did."

"Let me see."

I pulled my jeans down and lifted my tee shirt to show her that I indeed had.

"Nice....good to see that you enjoyed it too."

I looked down and saw a wet spot at the head of my stiff cock, I had already dribbled a little into her panties. I let the tee-shirt drop modestly.

"Ok, Steven, so here is what I am thinking. You look absolutely gorgeous in my panties, minus one little detail. All that hair. You need to shave off some of that hair. You have too much of it. You look like a fucking faggot wearing girly underwear...you don't want that do you?"

"Um, no, definitely not." I agreed.

"Well then, go in the bathroom and you will find a bottle of shaving cream, a razor, and a bottle of Nair on the tub. Shave, then use the Nair to get rid of any stubble. I expect to see some smooth legs when you get back in here. Then, and only then can we play.

I agreed without a word, and shaved my legs without complaint. When I was done and they were smooth, I marveled at how good they felt under my hands, and how good they could feel under her hands. Staring at myself in the mirror, I looked like a girl from the thighs down, a girl with some nice fucking legs if I do say so myself. But the illusion faded as I looked at my hard cock and the hair surrounding it. And then, as a joke, I thought Sarah might like to see a little less pubic hair, so I shaved it down to a tiny strip, similar to what porn stars generally wear. I felt so dirty as I pulled the panties back up.

When I came back into Sarah's room she was no wear to be seen. So out of curiosity, while she was gone, I made my way over to that inverted chair. I startled it like a motorcycle and grabbed onto the handles in front of me. I could only imagine what I looked like in this chair with my smooth pink ass hoisted high into the air. And then I felt the tug at my wrists as she tied my hands onto the handles, and I could not complain. After she had me tied into place, she shut off the overhead lights and I was shrouded in complete and utter darkness.

After a few minutes with my ass in the air like that, I felt her hand tracing my legs, cupping my butt generously. My cock pulsed against the chair beneath me. Her hands traced my legs for awhile, then pulled away suddenly. A few minutes passed and my cock grew in anticipation. After that short while, the hands reappeared on my ass, and they were sliding the panties to the side, freeing my still sore ass. And then I felt something press against my anus, a hard thing that I couldn't see behind me. I loosened myself against it, allowed it to enter me. I felt it slipping inside, and I moaned. It felt huge whatever it was, and it also felt so right, so good, like it belonged. I moaned biting my lip, and opened myself to it. My ass begged for it. And it slid in smoothly, I felt it go all the way in. And then it was fucking me...slowly at first, but picking up an enthusiastic speed with each pump. And despite the initial pain, it had found my pleasure center, and it felt so god damned good. And it fucked me, and I fucked it, backing my ass up when I could, squeezing with every pump, squeezing it as best I could. Then I felt her hand, her hand beneath the table, and it grabbed a hold of my cock and was pumping in time, ass fucking and pumping. I was so close to ecstasy, and I could hear her moaning as well. And with that thing inside me, and her pumping feverishly on my cock, I exploded with orgasmic fury. Spraying cum wherever it went, with no regard. I heard her moaning in climax as well, and then the object left me, and her hand left my now limp cock.

The lights flashed on and my eyes took their time adjusting. But when they came around, Sarah was standing in front of me stoking that plastic cock, only it was attached to her now. She had worn the dildo attached to herself and fucked me with it. It was odd to watch Sarah stroking the plastic cock that had just fucked me, but it made me hard again as I watched. Something about her holding all that power in her hand was so hot to me. She rolled her head back and laughed as she continued stroking it in front of my captivated eyes.

Report Story

bydiamonddbb© 0 comments/ 51750 views/ 4 favorites

Share the love

Similar stories

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

heartAkhiljha, Fm20132013 and 2 other people favorited this story! 

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: