Hope you enjoy the second chapter......
------------------------------------------------------------ Chapter 2
At 7 sharp I knocked on Jessy's door nervous and anxious still not entirely sure what I was doing. I couldn't believe how hot a time I had down in the laundry room with her making me finger my own ass like a "pussy" and jerk off for her. The thought of taking it to the next level was exciting. Jessy answered the door dressed only in an over sized t-shirt and a pair of bright pink panties. Before I could open my mouth she announced my presence over her shoulder.
"Hey, its the guy from the laundry room. He showed up. I told you he'd come."
"Who?" A male voice answered.
"Remember that panty boy I told you I was messing around with? Well he's here" she replied as she ushered me into her apartment.
"Did you remember to wear my panties?" She whispered to me.
"Oh yes, of course", I replied.
"Oh, what a good little sissy." She smiled back.
As I walked in I saw Jessy's husband. He was a tall foreboding man with a scowl on his face and a tumbler of scotch in one hand.
"This is my husband Jeff, and Jeff this is ..." her voice trailed off as she had clearly forgotten my name but I was way too nervous to speak up. "... this is... oh lets just call him our little sissy." She finally said. And Jeff extended his hand.
"Nice to meet you..... Sissy" he shook my hand with a strong grip and a sarcastic look on his face. "Jessy tells me you're quite the little pussy eater...... and now you want to try sucking on some cock? That's good because I am horny as hell and Jessy refuses to put my dick anywhere near her mouth."
"I will as soon as you start going downtown on me." Jessy countered in a mocking tone. They both shared a chuckle.
I just stood there and gulped with a blank uncertain look on my face. I was stunned at how direct they were.
"What where you looking for, a little foreplay first?" Jeff asked sarcastically.
"Oh where are my manners." Jessy interrupted, "Would you like a beer?"
"Sure. Thank you." I replied.
"Me too honey. If you don't mind?" Jeff chimed in.
Jeff walked over to the couch. Unzipped his fly, dropped his pants and sat down. He took a cushion off the couch and put it on the floor between his legs. then in a much sweeter tone than he had used thus far he said
"Why don't you strip down to my wife's panties I'm sure you are wearing and kneel down here and get comfortable. " he said pointing to the cushion.
I felt a rush of excitement inside and then quickly, but somewhat nervously, stripped down looking forward to what lay in front of me.
"Oh honey." Jessy interrupted, "Let me play a little dress up with our guests first. Just put some porn on while you're waiting. We won't be long. " Jeff grumbled "We'll make it worth your while.".
"Dress up?" I asked innocently.
"Yes. I want to dress you as a pretty girl. You'd like that, wouldn't you?"
With that she took me by the hand, dressed only in her panties with my hard cock poking out the top, and led me to the bathroom. There Jessy rubbed cream all over my body to make me soft and sweet smelling. It tickled as her hand rubbed my cock and balls and poked into my ass. She then matter-of-factly bent me over the tub and gave me an enema while the cream set in. I just went with it, enjoying the rush of warm water through my backside. But was humiliated as she watched me expel on the toilet. She repeated the enema just to ensure I was 'clean back there'. My face was bright crimson as she watched me expel and wipe with her smiling and making eye contact the whole time.
I was hard as a rock through out all of this. Then, as I showered off the cream, I realized it had taken all my body hair off my body. "Don't worry. It grows back" she said, but I was too far gone to care. She dried me off and started applying make-up, fake lashes and topped off with a wig. I then put on a matching panties and bra she stuffed some tissue paper.
"I used to pad my bra like that too before I got these" she said cradling her breasts, "But you looked totally cute like this."
After a couple final adjustments she had me look and I couldn't believe what I saw.
"Oh my god!" I exclaimed at seeing myself in the mirror. Not quite a passable girl, but a decidedly hot tranny. I looked good, I mean really good for a quick makeover. It turned me on and her as well as I saw her fingering herself through her panties as she looked at me longingly, proud of the transformation.
"Yes, you are a hot little sissy-boy, a ladyboy. Why don't you be my lesbian lover for minute." Jessy said and she leaned in and starting kissing me, tongues intertwined. She broke the kiss and reapplied the lipstick saying "First things first, Jeff needs a little loving too. Are you ready for him?....... oh, you know what sweetie, we need a girl name for you... how about Kim, or Kimmy that sounds sluttier." she paused "OK Kimmy, go give my husband the best blow job of his life."
Emboldened I got up to walk out, and Jessy stopped me.
"Remember, you are a girl. Walk like one, talk like one and show me that submissive eye flutter you put on for me down in the laundry."
I blushed, through the rouge on my cheeks, remembering how submissive I got earlier. I walked out shaking my hips "Are you ready for some action, big boy?" I said my best girlie voice to Jeff, somewhat surprised what came out of my mouth.
"Yeah, its about time." he replied. Then he looked up, "Damn honey, she is a fine looking bitch."
As I walked over I looked and saw he was watching some shemale porn. The 'girl' was on her hands and knees being fucked in ass by a strong muscle bound guy with a huge cock. Her own cock swaying back and forth between her legs to the rhythm of the pounding, all the while gagging on another guys cock. My mouth was watering at the scene. Jeff saw my reaction and said "Oh yeah bitch, that's gonna be you, isn't it."
"Uh, mmm" I stammered looking over to see him jerking his cock to the video. Slowly I started getting down on my knees in front of him.
"Jeff, I see you've met Kimmy. Please introduce her to her place in our apartment. Which is on her knees servicing us." Jessy said as she entered the living room while strapping on a dildo around her waist.
Once on my knees, his cock was only inches from my face and much, much bigger than mine. I reached out and started stroking it. The first time I'd ever stroked another guys cock. "Open your mouth Kimmy." Jeff said as he pushed the back of my head down into his crotch.
My lips parted as I started to take his cock into my mouth. The skin was soft and it tasted wonderful. Before I knew it I was bobbing my head up and down while only getting a few inches into my mouth. Jeff moaned and groaned and called me his bitch.
"That's right Kimmy, slobber on it. Take more cock. Deeper. I want to hear you gag." Jessy said as she came up behind me.
I redoubled my efforts, choking on Jeff's large member as I felt Jessy pull my panties to side and rub a thick dollop of lube on my "pussy".
"We are going to break you in Kimmy." Jessy said as she worked the lube inside, eventually finding my g-spot. I was in heaven. Jessy eventually pulled out her finger and I felt the large head of the dildo pressing against my entrance. This was bigger than anything I'd had before, but I wanted to please my new found mistress. She pressed her body weight onto me and the head popped in with a sharp bit of pain, before easing. She paused for a while stroking my back as I continued to suck and gag. Jeff was saying words of encouragement to me as he kept his hand on the back of my head while thrusting his cock into my mouth, face fucking me. I could tell he was getting close. Jessy continue to press against me driving her cock deeper into me, until I finally felt her belly and thighs against my butt and she said "Balls deep bitch. Kimmy I am fucking you balls deep!" I was in heaven.
I took Jeff's cock out of my mouth and inhaled sharply as the sudden fullness of her cock inside me, which overwhelmed me for a second. "You love that big cock in your pussy, don't you Kimmy?" Jessy asked.
"Oh god yes" I replied.
"Well than, take it. Take it like a woman." she said as she grabbed me by the hips and started to pump in and out. "That's right Kimmy, take that cock in your pussy while you have one in your mouth."
I resumed sucking Jeff and he held my head with both hands saying "Don't stop, don't stop" and shot his load into my mouth. I wanted to pull off but he kept my mouth sliding up and down his manhood for a while as his cum oozed out of the corners of my mouth. Finally pulled my mouth free and Jessy was starting to really pound me. Bucking and spanking me as she fucked me with complete abandon. Still fucking me doggy-style she got up off her knees and up on her feet and continued to power-pound me. "That's right bitch, take it. Take it in your pussy, take it up the ass. Take it like the little sissy faggot you are." The fucking and verbal humiliation was making me moan. She kept this up for a while and then eventually got tired, dismounted and took off her strap-on. Jeff had gotten up and she walked over and took his spot on the couch. Her pussy was dripping wet and she simply commanded: "Eat me, Kimmy. Eat me."
I starting lapping up her pussy, quite a switch from sucking Jeff. I was getting into it, and then I felt him come around to my backside.
"You got her all wet and lubed up for me honey?" Jeff said to Jessy. Jessy ignored him as her eyes were rolling into the back of her head in pleasure. "Good, 'cause I'd love to fuck me some virgin ass" He continued as he roughly rubbed his fingers into me before pressing the head of his cock against my ass. He was much bigger than the dildo and had gotten hard pretty quickly after he came. I moaned and groaned into Jessy pussy as he entered me, much more forcefully and quickly than Jessy had.
Before I knew it I felt his balls rubbing against mine and then I felt something I had never felt before. It was the feeling that this is where I needed to be. With a cock up my ass, taking it from a man, being his woman, his bitch. It felt good. It felt right. The wig had come off by this time, I could see from my reflection in the TV, and I looked like a total slut. Jeff grabbed me by the hair forcing me to arch my back as we fucked. I bucked back at him as he pounded me into submission. Jessy was rubbing herself off by now and shouting word of encouragement "Oh yeah baby, fuck him. fuck him good."
Jeff then gave me what I found out later is called a "reach-around", jerking me off as he fucked me. It was awesome. He then pulled out flipped me on my back and fucked me right there on the floor, fucking me as I rolled back up onto my shoulders. He was locking eyes with me and continuing to jerk me until I came all over my stomach. He picked up the cum and rubbed it all over my face. Then with a few more thrusts I felt him cum inside me.
"I think we found a keeper, baby" Jeff said to Jessy.
A keeper indeed. A keeper indeed.