Bondage & Discipline, Submission, S & M

Pay Up

by Donatella Den

That's right. I couldn't believe it either. I lost the bet. Maybe I was drunk. Maybe I should've put my glasses on. but I could've sworn that the dude was a chick. My Girlfriend Kay and I had alone over to Lucky Chenas because she 'Knew the person at the door. We were inside sipping our drinks when this woman came in. Now I know that this was a crossdressing club, but usually the guys go so over the too that it's obvious who is a real woman and who is not. Well, Kay noticed how I was checking this gal out and leaned in close to my ear.

"You know that's a guy, right?"

"What? Her? No way. That's a real woman. I can tell by the way she walks, by the way she moves."

We continued to watch her as she made her way around the bar, talking to friends. At one point she passed very close to us and I still couldn't see any tell‑tale signs. I checked her hands and wrists. They were big but since she had black elbow length gloves on I couldn't even tell if she had hairy arms. I checked for an Adams apple but the leather collar she wore made it impossible to tell. Kay spoke and knocked me out of my trance.

"I'll tell you what. I'll go see if I can pick her up. I'll tell her that my boyfriend and I would like to do a three way with her and would she be interested. I'll make you a bet. If she's a real woman and agrees, we go home together and you get to play and fuck us both. If she turns out to be a man, we still all go home together but I get to watch him fuck you. What do you say?"

I thought about it only a second, I was so sure of myself i didn't even consider the consequences.

"You're on." I said, confident that l would soon be up to my ears in pussy.

Kay made off for the bar and to find our "mystery" date. She returned a few minutes later with our new friend. She wore a tight black mini skirt, black, ankle high, lace up boots and a clingy top that showed that she certainly had what looked like real breasts. Her hair was long and brown and seemed natural. Although she wore a lot of make‑up it didn't seem excessive and I didn't see any stubble. It had to be woman! Kay said that "Terry" had agreed to get together with us and lived nearby. We decided to finish our drinks and head to her house. She lead us up a flight of stairs. She slid back the door to her place and wouldn't you know it, her pie was done up like a dungeon. !here was a rack on the far wall and a worship bench in the middle of the floor. 1 erry walked around lighting candies and told us to make ourselves comfortable as she made us some cocktails. Kay and i had played before but never in a real dungeon or with proper tools. Occasionally she would tie me to the bed and force me to do whatever she wanted. We always had fun in these little experiments and it looked like we were orina to have some fun tonight ( Terry sat down when she returned with our drinks and we started to talk. Kay told her how 1 thought for sure that she was a woman while she was sure that she was a man in drag. We discussed how good some transsexuals are at hiding their identity, all the while Terry not tinning her hand as to what sex he/she was. As we continued to discuss ,this; Kay suggested that we dress me up to see how convincing we could make me look. Terry said that she had some clothes that would probably fit me and that it sounded like fun.

Vile went into her bedroom and while Terry found clothes. Kay started to do my face. She gave me foundation and rouge and did my eyes up dark and sexy. Some bright red lipstick and i was looking hot. even with that scar on my cheek. Terry came over with some undergarments and they helped me put them on. I‑first a garter belt and stockings. The nylon felt good against. my skin as they fastened the garters for me. Next some silky red panties. Terrv told me that a true slut always wears her panties over her garters so that she can take them off without unhooking the hose! Vile all laughed. Next i nut on a red bra that matched the panties and we stuffed it with some rolled up socks. Terri had chosen a couple of short dresses and I tried each one on looking for the one with the proper fit. We decided on a sheer black number that allowed you to see the matching bra and panties right through it. Once I was completely dressed. we went the closet to look at shoes. So many to choose from! I nicked a nadir of thigh high leather lobs and tried them on. They fit well enough and we all walked back into the main room to look at our creation. Despite the fact that I didn't have a wig nn, (my hair was pretty Inca anyway) I looked quite fetching. Kay said that she was getting really wet .looking at me dressed as a woman and wanted to take "advantage" of me. This was our code word that meant she was now assuming a dominant stance and that I was to obey her every desire. We played this game frequently and I loved giving up my control to such a strong; beautiful woman. I immediately got down on my knees with my forehead touching the floor and waited for her next command. She walked behind me and commented on how inviting I looked with my ass raised high in the air. She gave me a sharp swat across my butt and i felt the warmth spread throughout my entire body.

Kay spoke as she slowly circled around me and Terry looked on.

"So here we are. You at my mercy and in the presence of another. Is she a woman or is she a man? 1 bet you would love to know, wouldn't you?"

I nodded my head in agreement." Yes Your Highness, you know that is true."

"And you remember our agreement? If this person is a woman, you are going to service and please us both at my discretion and whim, which 1 know you will enjoy very much. On the other hand, if this person is a man, you are still going to do everything 1 say with just as much relish and enthusiasm. I do hope that is clear."

Crystal clear." I replied.

With a laugh she said that she would like me to go over to the

worship bench and to kneel and wait. Terry walked over and stood in front of me with her crotch an inch from my face. It looked good, no bulge anyway. Kay started to smack my ass and instructed Terry to do a striptease for me and to slowly reveal to me what she has between her legs. She starts with her top. She takes it off revealing the most beautiful set of tits. They fill out her bra nicely. I breathe a sigh of relief. Unless she is pre‑op on hormones, she's a woman. She turns and, with her back to me, slow and sexy, she shimmies out of her dress. She sticks out her shapely ass clad only in her satin panties.

"Kiss her ass!" Kay demands from behind me. her hands continuing to spank my ass. I can feel it starting to burn. "Now tell me that you want whatever Terry has between her legs, weather it's cunt or cock, in your mouth. Convince me."

"lease Your Highness, My Goddess. Please let me eat or suck on whatever Terry has between her legs. I promise that I will please both you and her If you allow me to do so."

"is that the best you can do?"

"lease Goddess. Your Royal Highness. I am drooling at the prospect of putting in my mouth whatever Terry has to offer me. If it is a cock, I will suck it until my mouth is overflowing with come and I will swallow every drop. If it is a cunt, I will suck and eat it until she shudders with her orgasm, and not stop before."

"That sounds more like it. Turn around Terry and show my pet what you have to offer him."

Terry slowly turned around to face me with her hands playing with and wrapped around the biggest, hardest shaft that I had ever seen! A pre‑op transsexual! You Betcha!!