I noticed the time strike 10pm on my watch as I got out of the cab outside the Red Circle. Hopefully tonight I was going to get lucky. After paying the cabbie and stepping out of the cab, I fixed my tight pink and black striped dress as I stood outside the club. The Red Circle was the most notorious Sex Clubs in the city where couples and singles went to hook up. Tonight was their Gender Bender Fetish night, which is why I had got dressed up tonight.

I have been crossdressing since I was quite young and as I grew older, I found it to be so erotic. My cock would almost always get hard as I slipped on a pair of panties and some hosiery. The feeling of the fabric on my legs and on my cock always drove me insane. Usually, I would sneak into my mother’s closet and try some of her stuff. But now that I am 25 and on my own, I have my very own private closet filled with all kinds of girlie items.

I took a deep breath as I moved towards the entrance where the bouncer stopped me. I showed him my identification and he looked back and forth at the id and smiled at me and waved me in. Slipping my identification back into my purse, I moved inside the club and headed inside.

As I entered, I noticed that there were not as many people inside the club as the last time I was here. Sure there were lots of men dressed in drag, a few CIS women (at least, I think they were CIS women) dressed in male attire and chatting away.

Venturing further inside, I also noticed a few people heading downstairs to the basement section. Now, this is where all the action took place. The basement section was where people went to commit the acts of debauchery they were here for. I myself had never participated or was never asked to join someone downstairs. I had merely been down as a spectator on occasion to see men and women fuck till they were a sweaty heap. You could see crossdressers playing amongst each other, crossdressers or T-girls getting fucked up their asses by other crossdressers or T-girls. On several occasions, CIS women would also be pegging crossdressers or T-girls with strap-ons.

That was my fetish. Pegging.

I had been introduced to pegging when I was in my senior year at high school by an older woman who happened to be our neighbor. She loved fucking me when I wore her sexy lingerie and acted like a slut. Almost every week I found myself on my knees or on my back taking her rubber cock. She loved playing the masculine role and many a time dressed up like a man as she fucked me. It turned me on so much to see the gender roles reversed like that. It made me feel vulnerable and submissive, just like a woman and I came hard every time.

Alas, once I moved to college, it became increasingly difficult to find a girl who would share this fetish with me. I did have a few casual encounters with women I had met on the internet, but none of them ever dressed up in masculine clothing.

As I reached the bar, a drag queen approached me and asked me what I would like to drink. I ordered a Manhattan and stood at the bar as I eyed the people inside, trying to see if there was someone who caught my eye.

I sighed as it seemed like it was going to be another slow night and I wasn’t going to see any action. Taking a big sip of my drink, it was then that I noticed her walk in. Blonde, hair pulled back in a ponytail, dark red lipstick and dressed in a Tuxedo. Though the club was a bit dark with some ambient lighting, I did notice that she looked a little older. Fixing the cuffs of tux, she stopped at the other end of the bar and ordered a drink as she began to peruse around the floor herself.

It didn’t take but a couple of minutes for her to glance in my direction. I met her gaze as I sipped my drink. She was gorgeous. I couldn’t keep my eyes off her as she held my gaze. She took a couple of sips of her drink and moved towards my direction. My heart began to flutter a bit. For a second I felt my stomach flip but the sensation quickly went away as she brushed past me. A bit disappointed, I sighed as I went back to my drink. I downed it rather quickly and ordered myself another one as the blonde took a seat at a table a few feet away from me.

I caught myself looking in her direction as I caught her eyeing me discreetly once in a while. A couple of girls approached her and began talking to her, but she very politely sent them away as she continued slowly sipping away at her drink. As I turned in her direction, I saw that she had finished her drink and was moving back at the bar.

She stopped right next to me as the bartender walked up to her.

“Another scotch, please.”

As the bartender went to fetch her drink, I felt a hand slowly begin to caress my ass. I gasped a bit and looked in her direction, but she didn’t look back or say anything. Her slow soft caressing had turned to hard groping as she grabbed on to my ass. My cock twitched inside my panties as she continued to molest me. I was getting really horny and my breathing became raspy. Her drink arrived and I felt her hand leave my ass as she produced some money from her pockets and paid the bartender. A little disappointed, I continued to steal glances at her.

Discreetly, she grabbed my free hand and placed it at her crotch as I felt a bulge inside her pants. It felt hard but soft at the same time as she made me massage her bulge. She went back to her drink and back to groping my butt as my hand left her groin. Her hand slowly snaked under my dress as she grabbed onto my panty covered ass. I said and did nothing as my molestation continued. A couple of minutes later, she downed her drink in one swig and looked in my direction.

I took a deep breath and gulped down the remainder of my drink. I headed down the stairs into the semi-dark passages of the basement. It was like a maze with rooms on either side of the hallway. Most of them were closed whereas some of them were open and you could see all kinds of debauchery taking place. The hallways echoed with the sound of moans and groans as I continued on further.  Taking a left turn at the end of the hall, I felt a hand grab me and push me against the wall covering my mouth. It was the blonde woman from the bar.

“Shhh.”

I nodded as she moved her hand down from my mouth and began to grope and caress me. She began to squeeze and caress my fake tits as she gave my lips a gentle and seductive lick. I could only gasp and moan as she continued to molest me as she had done earlier. My hand snaked down towards her groin and began to caress the bulge in her trousers.  She licked and nibbled my neck as she drove me into a lust filled frenzy.

She pushed me down on my knees, pinning me against the wall as her groin was but inches from my face.

“Unbuckle my pants,” she commanded.

I looked around the hallway to see if there was anyone there. It was empty and I was quite scared that someone would walk past us and see what was happening.

“Now!” she commanded once again.

I was getting really aroused and the authority with which she uttered the words compelled me to obey. I unbuckled her pants and pulled them down. She wore a pair of jockey briefs which I pulled down as well to reveal a black dildo attached to a strap-on harness. She put her hands on my chin and caressed me as I knew what she wanted me to do.

Giving the dildo a few strokes, I took it into my mouth and began to suck on it. I stroked it as I bobbed my head up and down. I felt like such a slut, on my knees, in the dark passage of a sex club, blowing a complete strangers strap-on cock. I gave the head a few licks and stroked it as I licked it from the base to the tip.

Suddenly a door next to us opened as a couple walked out. I looked up at them as I continued at the task at hand. I got a snicker from one of the girls as they headed off.  The blonde pulled her cock out of my mouth and began to smack it on my lips. I looked up into her eyes as she had a smile on her face.

A few smacks later, she pulled me up to my feet and turned me around, pinning my front to the wall. She began to grind against me as she slowly lifted my dress up, bringing my panty covered ass. Her hand moved to my now erect cock inside my panties and she began to caress it with one hand while the other grabbed my neck firmly. She licked my earlobes and nibbled on them as my breathing became shallow.

“Please fuck me,” I moaned softly.

“Is that what you want?” she cooed.

“Yes, please! I want your dick inside me!”

Giving both my fake tits a squeeze, she pulled down the straps of my dress exposing my bra. She continued to toy with me for a few more minutes as my frustration and lust grew. Then I felt her violently pull my panties down, freeing my cock from its constraints. Grabbing my hips, she pulled me back a little and made me spread my legs.

I felt a wet finger, probably lubed up, on my asshole as I felt her insert one finger inside me. I gasped at the intrusion. She fingered me for a minute or two as I waited in anticipation for what was coming next. A minute later, her finger out, I felt the tip of her cock against my rosebud. I took a deep breath and tried to relax as I felt the tip of her cock enter me.

I moaned as she slowly pushed further inside me. Her cock wasn’t too huge, but it wasn’t small either. A few strokes later, she had her cock inside me balls deep. She moved slowly, pulling her cock out almost completely at first and the driving the whole thing inside me in one full stroke. She did this a few times and then quickened the pace.

I gasped and moaned as I was being taken a cheap slut. Grabbing my hips firmly, she pounded into me like jackhammer driving me insane with pleasure. Leaning in, she continued to fuck me as her hand reached down and grabbed my now free cock and began to jerk me, her movements matching the rhythm with each pump of her wrist on my cock. It didn’t take me long and soon I began to cum.

“FUCKKK!” I cried out.

As my orgasm slowly began to fade, she slowed down and held me as my body shook with intensity. Once she had sensed that I was now done, she slowly pulled her cock out of me. I turned around and faced her as I tried to catch my breath. She wiped her hands, stained with my cum, on my dress and pulled up her briefs and her pants. Once fully clothed, she leaned into me and gave me a kiss on my lips. Pulling a tissue out of her pants, she stuffed it into my bra, giving me a smile and walking off.

I composed myself as best as I could and pulled my panties up and straightened my dress. I headed back up towards the bar and noticed that she wasn’t anywhere to be seen. Pulling the tissue that she had stuffed inside my bra, I noticed something written on it.

Joanna

xxxx-xxxx

It was a name and a phone number!

I smiled to myself as I put the tissue into my purse and decided to head back home after what was the most thrilling night of my life.