My New Job Ch. 02

I looked at Liz shocked and then Karen as her stunning looks were making me even more embarrassed. I never thought I would wear a ball-gag and no idea what they could ask me.

"I will be gentle on him. He is cute too." Karen answered as she looked at Liz and not me.

She then turned her head to me. "So what did Liz make you do that you liked the most?"

Liz answered before I could even say a word. "No whips Karen. I know you have a thing for whips, but I like him with no marks on him. You can have him eat you out before and after you are with men, and even piss on him but don't mark him up."

Karen then turned to Liz as I wanted to say something but my mind drew a blank as the embarrassment washed over me. I wanted to say that I wanted to have sex with Liz all the time wanted to come out but I could not bear to say it.

"Ohh, so he likes eating cream pies and drinking piss. Does he like strap-ons though?" Karen asked Liz as she looked right at me adding to the redness in my face.

"Stand up and show her what Jeri makes you wear." Liz said to me calmly.

I knew I should have changed but I liked the sensation of the smooth light material on my balls and penis. I loved how it held everything in place and how just knowing I was wearing them was erotic.

I stood up and unbuckled my belt feeling weird that I was doing it, but I knew Liz was never going to judge me, although I wondered if she knew Jeri had fucked me. I then pulled down my jeans to my thighs revealing the black sheer panties that Jeri got for me.

"He is cute wearing those." Karen said as her face lit up and her hand went out to touch my balls.

She looked right at me as I felt her soft caressing hand on my balls through the panties. "You like that don't you?"

I felt her soft fingers cupping my balls, holding them like they were toys of hers. My erection came on as much as I wanted it not too. I could not help it as her fingers seemed like touch my scrotum in such a way that made me want more.

"Ohhhhh...yes." I said trying not to moan.

She looked at Liz as she sat there smiling at me. "Have you fucked him yet, is he good in bed?"

"Nooo, he is my helper. But I do owe him a few orgasms." Liz answered.

I felt good that Liz thought I was owed pleasure, but sad that she never mentioned wanting to have sex with me. Karen then stared at me. "Would you mind eating my pussy when you get back?"

I nodded thinking that the hottest girl ever wanted to have me pleasure them and I would be able to see her naked. I didn't care about anything other than doing what she wanted me to do. My erection was poking out through the panties and her hand was now firmly gripping my balls and I knew she had control over me.

"He is quite good." Liz added as I could not look at her as Karen had all of my attention.

"Mmmm good. Do you mind if my pussy is a little...messy?"

I nodded my head quickly thinking of all the times I ate Liz out after the clients' came in her. My mind flashed with the thoughts of how warm sperm tastes and how I licked her clean knowing a guy just ejaculated in her and I tasted another cock's warm reward.

"Good...because I love it when a tongue finishes me off and I have a guy online that's into that stuff. I am going to love having a cute boy like you around to care for me and clean me up."

"Well, don't abuse him too much; he also finishes me off each time." Liz added in as my memory was thinking of all the times Liz asked me to do something and now having more girls to listen too. I did not know where to start or what to say as it was all happening so fast.

"I got to get back." I said calmly not knowing really what to say and what to do. I felt so nervous that I was going to do or say something wrong and they would hate me. I figured if I just said nothing I would be better off.

Karen moved her hand from my balls and smiled at me. "I can't wait to make you wear my panties as you clean me."

I left quickly fearing that she might change her mind or I might say or do something wrong. I so wanted to say something, or even do something but I couldn't budge. It was like my mouth was closed and my body was frozen.

In the car I was running through all of the things I could have said and the possibilities that could have happened. I knew if I asked Liz for sex or even a blowjob I could have gotten it. Karen then popped in my mind of how gorgeous she was and just seeing her naked was good enough for me, and anything else was just an added bonus.

I arrived at the house tired and worn from the drive. I headed inside to see Jeri was not even there. I figured she was out shopping or enjoying her time off. I was in my bed sleeping and sporting my erection contemplating what could have been and what might be.

I woke up and left my room and was greeted with a "Hey you."

Jeri was on the couch drinking her coffee while typing away at her laptop. She looked at me while wearing a simple t-shirt and cut-off shorts. Her tanned legs were on display as she sat on the couch with a movie playing in the background. She paused the movie and jumped up giving me a small hug and kiss.

"Enjoy your day off?" I asked as I felt her breasts push against me.

"Well...I did some shopping and then took a long hot bath. Then I shaved my legs and such. I call that a good day."

"I have to head back tomorrow. Liz wants me to work there for a few days of the week." I replied looking at Jeri and wondering if she was going to be either upset or happy about being alone.

"Liz told me already. I guess, I am going to be all alone for those days. But, I can manage."

I went towards the kitchen hungry as Jeri followed. It was late afternoon and I needed something to eat from sleeping most of the day. I was making something to eat when Jeri sat at the table pulling her phone out.

She then looked at me with a serious facial expression. "I don't have enough clients to cover the rent Liz is going to charge me. I am only going to stay for the summer and then am going to leave. I saw the place Liz has and I know she has you staying in that bottom area. I was hoping...well, I want to ask if you don't mind letting me stay there with you."

"You're leaving here?" I ask not knowing why Jeri was looking to leave as I know she charge a really high rate for what she did.

"I just want to do something where I don't have to jerk off guys or fuck them for hours. I want something stable and I also know that the area Liz is in is great."

I thought about it really quickly and figured that Liz had the real say in who stayed at the house and who did not. "I will ask her."

"Aweee...thank you." Jeri cooed as she leaned in and kissed me on the lips quick.

"You know...I did not cum today and I am really horny. Are you still wearing panties?" She asked showing a big smile.

I then realized that I could have gotten away with not doing it any more but for some strange pull in my mind, I wanted to wear them, I wanted to feel that taboo of wearing girly panties. Being told what to do and accepting what was happening to me.

I looked up at her not knowing what she was going to think or say, but I decided to just be truthful, after all she needed me to ask Liz. "I am."

"Good...that means you still want to play around. Eat up and then get in the shower. I will put out some clothes for you to wear to make you feel all pretty, and then you can cum."

"Are you going to jerk me off first?" I asked wondering if she was going to give a massage like before.

"Ohh noo. I want you really hard and excited when I fuck you. It will add to the pleasure of when you do cum, but don't worry I will let you cum though."

She got up and went into her room as I finished up eating. I heard her rustling though bag and drawers coming as I knew she was picking stuff out for me. I then got up and headed towards the shower. I needed to clean up anyway and saw this as a win win, but was still nervous about what was going to happen.

As I was cleaning myself out and shaving the stubble that grew back, I felt the twinge of nervous energy. Was I going to love it again or hate it? I felt guilty about what I was doing but then loved the taboo erotic nature of it all. I saw Jeri naked a few times and wondered how she was so feminine and pretty and yet had a monster sized cock on her.

I stepped out and could feel the strange excitement of trying something new again. I walked into my room and saw a very thin sheer set of panties and matching stockings on my bed. Right next to the stockings was the matching bra for the panties. It was sheer and had some frills on the ends.

I put on the panties first and felt the distinct sensual feel of the thin soft material against my privates. This was followed by me putting on the bra and adjusting it to fit me. The lace material was thin and had a strange but arousing feel against the nipples. I was not erect but oddly aroused though. I then put on the stockings and felt the tightness it brought to my legs accompanied by the erotic sensation that I was wearing girls' lingerie and looking very feminine.

I walked out and Jeri was there wearing her bra and panties. It was the same as mine too. She reached out taking my hand to pull me to her bedroom. "Oh you look so pretty in that."

I had to admit that it did feel both erotic and smooth on my body. I then turned to Jeri as we got in the bedroom. "It does feel kind of nice."

Jeri put her lips on mine and I quickly opened my mouth to accept her tongue. Her hands were on my holding my in place as he tongue began exploring my mouth. My heart was beating fast and my member stirred from the kiss and pushed out the panties.

I moved my hands up to her breasts feeling how soft yet firm they were. The thin material of the bra made it easy to feel the curves of her chest as she continued to move her tongue against mine.

Jeri then began pushing me down until the kiss was broken. "Go down on me baby."

I was on my knees as Jeri pulled her panties to the side letting her soft cock flop out in front of my face. "Be a good girl and suck it nice."

I stared right at her limp girl dick feeling like a girl since she called me that and everything I was wearing made me think I was one. My body was filled with erotic notions and thoughts as I just looked at her girl cock. It was not completely soft but not raging either. The head of her member seemed harmless and the shaft not so thick. Although I knew it would expand and I knew it was going to stretch my rectum out.

I felt my stomach tighten with anticipation of the dirty erotic act I was about to do. I moved slowly towards it reaching for her legs as my mouth open up taking in the head. The smell and taste of the musky aroma that only a prick has was now filing my nostrils and my taste buds.

I could feel the soft texture of her fleshy cock as I moved my mouth further down her shaft. I could feel her excitement too as her member was actually getting hard in my mouth. My own dick was growing too as the taboo act of sucking a dick hit me. It was not just any dick but a girl dick and a dick that fucked me twice before.

I moved slowly on her shaft tasting more and more of her shaft and also smelling her girlish perfume as I inhaled deeply as I took her whole fun stick in my mouth.

"That's it baby...oh yes. You are sucking me so good." Jeri moaned out as I could feel her erection finally at full strength in my mouth.

I was moving fast as she began to rock her hips like she was fucking my mouth. She was not moving fast, but it was fast enough that I felt my mouth being fucked. I wrapped my lips tight around her shaft and just followed her hips in synch as she was using my mouth to get off.

"Your so good at this baby, sucking my dick just like a girl would do. Ohhh yes...I love seeing you all dressed up while you suck me too."

My mouth was stuffed with her girl dick and I was beginning to slobber at little as she was going faster with her hips. She was almost full on fucking me with her erection too. She was noting going in all the way but I was still almost to the point of gagging.

Jeri finally pulled away and lifted me up to my feet. Her mouth wet right to mine kissing me and tasting my saliva. It was a short kiss as she motioned for me to go to the bed. "Bend over baby. I am going to love your cute ass right now."

I bent over still wearing the panties and feeling my heart race with anticipation. I knew what was going to happen and recalled the memory of what it felt like last time. I was feeling even more like a girl than last time as the bra really pushed me over the edge.

Jeri pulled down my panties to my knees as I was still bent over and then I felt her hands on my ass. I was expecting to feel lube drip on my ass, but was suddenly taken back when her hands began spreading me open.

As the air was hitting my exposed anus Jeri's tongue swiped up my asshole sending tingles of strange pleasures to my brain. Over and over her tongue licked at my ass until finally she burrowed her tongue right into me.

My ass cheeks were wide open as I could feel her warm wet tongue digging and licking at my open hole. I did not know it could feel so good and even moaned from the intense erotic pleasure. Feeling her face buried in my ass as her tongue pleasured added to wanting more too.

My asshole tingled with warm wet pleasure as her tongue circled the hole and then dove in. The soft nudging sensation of her tongue in the outer muscles of my rectum was nothing I felt before and now something I could see myself wanting again and again.

"Ohhhh God...Ohhhh God." I moaned feeling her tongue just dig out my pleasure from the pleasure sensors of my asshole rim.

After what seemed like an eternity Jeri pulled her face away. "Your ass pussy is ready now. You ready for my cock?"

"Yes." I answered feeling my chest pound with desire and forbidden lust. My wet anal rim now feeling cold and kinky.

I then felt my ass being spread open more and the sound of a bottle opening. "I am going to go really slow. I want to make this last."

As the cold sensation of lube hit my open ass hole I knew I was seconds away from being fucked again. I was feeling the stocking on my legs and the bra on my chest wondering what I was really doing and then wondering why I wanted it so bad.

I felt her crown start pushing against my anal ring trying to gain entry. My lubed and licked anal barrier was no match, and my rectal muscles surrendered to her large lubed girl intruder.

"Ohhhh." I moaned loud as Jeri pushed slowly inside me. Her mushroom popping in letting me know that my anus was now a hole to be fucked. I could feel the full sensation envelop my whole body as her girl cock slipped past more of my anal muscles with ease.

"That's a good boy...oh I feel how tight you still are. You are going to have to stay relaxed just like before." Jeri soft spoke trying to calm me down.

I could feel my asshole tightening and trying to push out the intruder like it was meant too. I felt the sensation of fullness become more and more as there was no hope of pushing it out as she pushed deeper into me.

"Okayyyyy...tryingggg." I softly moaned as I let my body relax even though the pressure in my butt hole was intense. It was not that it was painful but more of a full and stretched sensation.

"That's...it. Just relax and let it happen. Just let your boy ass adjust to my cock." Jeri said again in her soothing voice.

I actively concentrate to relax my muscles letting it go almost limp as I felt the pressure in my rectum ease a bit now that I was not clenching. I could feel the familiar thickness of her girl member in me as she was still allowing me to adjust to her size.

"Ohhh...yess, that's it. You're doing good, just keep relaxed." She moaned as I felt her retreat slightly only to slide back in me.

I was moaning softly again as Jeri pushed as far in as she could making me fell stuffed. Her body was pressed up against mine letting me know she was fully impaling me. My ass was not burning nor was it painful as she was now fully entrenched in my bowels. The sensation was amazing and almost felt guilty for enjoying it too.

"That's it...just relax and enjoy." Jeri cooed at me as I felt her pull almost all the way out and the slowly sink back in deep again.

"Ohhhhh GOD." I moaned louder as I could not help but feel the erotic pleasurable sensation of having my anal passage stimulated.

The size of her girl dick was making me feel so stuffed but it also felt so amazing at the same time. I could still feel the stretching sensation as my anal muscles and yet there was no pain but just a dull pressure. The pressure was not uncomfortable and when she gliding in and out of me it was a pleasurable pressure.

With slow methodical thrusts, Jeri was pushing deep before pulling out. It felt like her girl cock was over a foot long as she rocked her hips against me sending the knob of her cock deep into my anal cavity. My eyes open and my heart thundered as I knew that I was being butt fucked and was loving it.

"Your liking this...I can tell." She said still rocking her hips against my butt.

"YES...it feels good." I admitted as my own member was now soft and dripping precum. I was feeling my anal muscles finally giving up the fight of trying to close on her she cock.

"Just keep relaxed and imagine you're a girl being fucked. Just think about your sissy body loving cock, all dressed up and being fucked like a good girl."

The pressure in my butt was there, but it felt so wonderful now as my mind did what she wanted it to do. I could feel the bra on my chest and the panties on my ankles as the stockings constricted my legs and thighs. I did feel like a girl being fucked as each thrust of her girl organ was confirming it. My limp member was not masculine in my mind as it hung there lifeless and dripping precum like it was never to be used.

"Ohhh...ohhhh." I moaned as I could feel an orgasm approaching as her girl cock was rubbing on my anal pleasure sensor. Over and over her tip was hitting it as my own internal pleasure was building.

"That's it...just relax and let it happen. Don't force it...just stay relaxed and calm as it happens baby." Jeri spoke easing me into my anal bliss.

I wanted to push so bad, I want to push out my orgasm and cum right then and there. I held back still focused on relaxing even though I didn't have to as much. Her thick member was filling me up and stretching me to the point I felt so open and yet full at the same time.

"This is how sissy girls get fucked. This is how they cum too. Just keep relaxed...pinch your nipples through the bra. Just imagine you're a girl being fucked and let it happen." Jeri moaned out softly as I knew she was enjoying my ass as I felt her cock pulse a bit.

Her hands were on my hips still bumping her waist against mine in a steady not so fast pace. I could swear I felt every inch of her thick girl dick glide into me. She was not going fast like before but thrusting deep confirming I was an anal slut. I could not deny the intense pleasure either as I did what she told me to do, and pinched my nipples feeling the thin bra cup on my skin.

"That's it baby...your doing great. Your ass is taking me perfectly now like it was a girl pussy. Just keep your mind on being a good sissy girl and think about how good it feels to be fucked like this."

"Ohhh Goddd. It feels good." I cried out not caring that I was wearing girl's panties, stockings and a bra. I gave into the sensation that she was using my asshole as pussy and that I was a girl for that brief moment.

The urge to get hard was gone as I felt my limp member just oozing precum. My fingers pinching my nipples through the bra as I felt them come to erect points. It happened just then as I felt my orgasm dull my senses and my penis drool out a thin stream of orgasmic liquid.