My New Job Ch. 02

"Ahhhhh...I am cumming." I moan loud finally tightening up as Jeri stayed still impaled deep in me.

"Ohhh...you did good." She complimented me and then pulled out.

I did not know if it was over and that was it until she motioned for me to move. "Here get on the bed and lift your legs up while you're on your back."

As I moved into position I saw my soft member covered in wet juices that was not very thick like normal cum, but it wasn't precum either. I then laid on my back and lifted my legs up like I was ready to be fucked missionary.

Jeri had an empty glass in one hand and the bottle of lube in the other. She opened my legs wide like I was a girl spreading her legs for a man. I could see her she-cock covered in lube from fucking me and she was hard as ever too.

"We are going to try something else now. You are going to love it. I just need you to tell me before you cum though. This will only work if you tell me before it happens."

I nodded my head as she then took aim of her shaft and I felt her slip into my rectum once again. I was so open that I only felt the pressure again as the familiar sensation of her being inside of me returned.

Her hand went right at my own prick. She then poured lube on my tip covering it and letting it drip to my limp shaft. She threw the lube on the bed and began stroking me softly. Her girl cock buried deep but not moving as her hand stroked me to life.

"Ohhhh." I moaned as I finally felt my dick come to attention quickly as her thumb pressed and moved on the sensitive tip.

"Just think how dirty you are as I stroke you. Just think about how you're dressed like a girl being fucked like one. How you experienced cuming like a girl and how you now wear panties everyday like a girl would."

I could not help it and with her hand stroking my lubed member I felt powerless to not think about anything else other than what she told me to think about. My thoughts were that of how bad I was and how erotic it felt to wear girl's panties. How the bra I was currently wearing felt good on my nipples and how wonderful it was to have her she-dick deep in me.

I began to squirm, pinching my nipples as I felt her hand stroke me. The tip of her thumb moving in circles around my piss slit while pressing down on it. Her other hand stroking me as the sensation of her thumb on my cock head was so overwhelming.

"Mmmm...you're throbbing hard. You're going to love what we do next. Just keep your mind on how you swallowed men's' loads and the feeling of a dick deep in you."

I instantly thought of all the times I licked Liz clean and the times she told me to lick my own jazz from her. Jeri's hand was stroking me harder as she kept pressure on the tip of me dick bringing me closer and closer. I was never turned on so much and so fast in my life.

"I am close...Ohhhhh I am close." I moaned loud letting my thoughts think about how a real cock was in me and how I was a girl for that brief moment.

Jeri quickly stopped stroking me and began to fuck me. Her cock pounding me hard now as I felt like my ass was so open. She was quickly drilling my ass as her body banged me like I was a common slut.

My orgasm was so close and yet I could not stop it from getting closer, just as I thought it was going to happen in a moment of brilliant pleasure it stopped. Jeri stopped fucking me and she was no longer stroking me. I was so close the sensation of my orgasm was still coming though.

She put the glass right at my erection as for some reason it came. My thick hot load was filling the glass and yet I was experiencing no pleasure whatsoever. My orgasm was being denied and yet my pearly sperm was filling the glass.

"Open your mouth and don't swallow."

I opened my mouth as she moved the glass towards my lips. As her wrist moved I then saw my thick load move out of the glass. The initial taste was there followed by the stronger taste of my tangy sperm. My taste buds were now overloaded with the musk flavored taste of my warm cum.

Jeri moved her hand back to my slick member as she then began to thrust in my asshole again. "Now you can cum for real this time. I want you to savor the taste of sperm while I stroke you to the best orgasm ever. When you cum, you can swallow that hot load."

She now not going slow as she began to plow into my stretched anal hole like she was on a mission now. Her hands were on my legs holding them in place as she directed her girl stick right into my ass. Her hand stroking me like before as I squirmed with pleasure from both my ass and my own member.

"Hold that cum in your mouth...hold it. Don't swallow a drop until you cum." She moaned out as I her hips continued to pound my ass.

I knew she had to be close as she was fucking me hard. I felt like a slut as the taste of sperm was now dominating my mouth and my thoughts. The sensation of wearing a bra and stockings only added to the taboo feeling I had as my anal muscles were open for fucking.

"Be a good girly boy and swallow when you cum. Just gulp it down like it was a meal. I know the taste is all in your mouth now." Jeri spoke smiling at me.

Her hips were flailing now as she was drilling my body. I was so lose I could feel nothing but pleasurable pressure in my ass. Her hand was stroking as the sound of the lube squishing in her hand was filing my ears. I was close as her expert fingers slide along the underside of my dick and her thumb pressed hard on the helmet.

"Ahhhh...Fuck." Jeri moaned out in her girly voice as I felt a slight sensation of warmth. Her body tightened and froze deep in me as I knew she was filling me with her girl sperm.

I was being cummed in like I was a girl. I was experiencing a creampie as I laid there wearing girls clothes. I felt the warmth of her member spit out its orgasm and the connection that she used my ass for pleasure and got off in it. I finally lost it and felt the building orgasm finally win out. I swallowed my hefty load in my mouth as I finally gave in to the sensation of ejaculation.

My eyes closed hard. My body stiffened life a board and I could finally feel sensation of my ass muscles as they clamped down on her thick beast like a vice.

"RRRRRRRR!" I groaned hard almost growling letting my body spew out the hardest orgasm in my life. I have no idea how much volume of cum I shot out or how far it spurted, but as I groaned I knew I was shooting off everything my balls had.

"Gooood...girl...you came. Wow. You came hard."

I finally opened my eyes and felt Jeri pull out of me. I looked to see her face covered with my creamy orgasm. "I am sorry. I did not know."

"Shhh. I aimed your cock right at my face cause I wanted it." She answered softly.

"That was the best orgasm ever." I admitted as she got up from the bed and I could see she was limp from the fucking she gave me.

"Those are the best ones. I came too and need a shower...want join me?" She asked.

Jeri never asked me before and I felt privileged to be asked. I nodded my head and followed her. I stripped out of the clothes as I walk dropping them on the ground leaving a trail of girl clothes as I watched her ass sway when she walked.

My eyes were glued to her ass as it was curved and portioned like she was born with a feminine physique. It bounced just right and yet swayed with each step.

When she turned towards me once we got in the bathroom, I looked down at what just fucked me. Her softened girl meat was hanging between her legs and my eyes just stared at it like it was the most wonderful thing in the world. It was like it did not match her body as everything was so feminine about her.

She got into the warm shower and I was there every step of the way. Her caressing hands soaped me up and washed me as I did the same to her in a most intimate way. When I got to her limp member I spent extra time cleaning it and loving how thick it while it as soft. It was so much larger than mine and I loved how delicate the skin was and how perfect it fit in my hand.

I was out of the shower getting dressed, although I was only wearing panties instead of the bra and stockings. I did not have any urges at all for anything as I knew my balls were properly drained of all cum and sexual desire.

I put on the T.V. and relaxed with Jeri putting her head on my lap. I felt we had something more than just sexual encounters now as she purred when I stroked her hair and treated her like she was my girlfriend instead of my roommate.

***

The next morning I woke up and Jeri was still passed out sleeping in her room. She had no clients scheduled and I could see that her week was almost absent of clients. I saw the text from Liz as she was excited that I was coming out today to set everything up.

I drove out there spending more time in my car planning out what I needed to do for Liz and what could happen if I ran into Karen again. I wanted something weird to happen and yet wanted to have sex with her too. I knew it was a long shot but I loved imagining it.

I got to the house and went through the back door to the basement to where I was supposed to stay. I saw that it was made up and furniture was moved in. I set up my computer and then moved the few other things I brought with me.

I knew I had to ask about Jeri, but I also did not want to come across as demanding. I figured Liz would be more inclined to let her stay if I finished everything first so that it was done and I just needed to keep up on things.

Knowing what Liz wanted, I setup all her accounts for her making sure it was password encrypted too. I thought it would be more difficult but setting up her site through a remote server out of the country was easy. I knew Liz would be happy and now I had something to tell her that would put her in a good mood to possible say yes to Jeri moving in.

It was late in the afternoon when I finally heard from Jeri asking me if I asked Liz. I responded with very soon and texted back that I would call her later. I still did not know if Jeri wanted to stay with me or just stay in the house with me.

I walked up the steps to hear Liz at the table again with Karen. Karen was wearing leather boots that went all the way up her thighs and had a matching leather corset that pushed up her breasts making them look huge. Her hair was in a ponytail and she looked ready to whip someone.

"Ohhhh...you're awake." Liz said as I walked in and sat at the table with them.

"I finished everything. All I have to do is check to see who has paid and give you times and special requests."

"Ohhh, look at you, your cute and smart." Karen said as I could see her looking at me like I was a piece of meat to be eaten.

"Your'e great. I am so glad you stumbled into my doorway. I owe you big time."

"Before you go rewarding him." Karen added as she then looked at me. "I have a guy online that wants to see something kinky. Do you mind being the guy in the video?"

"I guesss...what do I have to do?" I answered wondering how many lashes I was going to have to take.

"Well...the guy has a fetish with strap-ons and pee."

"You're going to fuck his ass and piss on him?" Liz commented as she stood up showing me that she was wearing nothing put panties and her bra today.

"I was hoping you would do the pee part while I fuck his cute ass."

I wanted to say something but I knew that I needed to be on Liz's good side and if I was asked to do something I would do it. The pee didn't bother me and the strap-on I kinda liked.

"Mmmm...I think I could help with the pee. But you cant fuck his ass to hard, I don't want you using some monster dildo up in his ass." Liz said as I knew that I was going to be covered with Liz's pee and thought about the time in the shower with her.

"Perfect. Well, I am going to set everything up and I will see you all tonight with what will happen."

I waited for Karen to leave making sure not to lookout her ass in the leather pants she was wearing as I knew she had a perfect body and desperately wanted to see more of her.

I looked at Liz hoping she would not get mad by me just asking. "Can I ask you a favor?"

"What do you need?"

"I don't think Jeri is going to be doing her thing anymore and wants to get out. I was thinking she could come say here...you know downstairs with me while she get work doing something else."

"I figured she was not going to be able to handle the house. She never did have a strong client list to break out on her own. I guess this means I will have to find some girls to take the house then."

"Does that mean she can stay here?" I asked thinking that she was going to say yes but wanting to make sure.

"If you want her too. I did not take you for a tranny lover though, but I guess it suits you." Liz answered but also giving me a reason to doubt myself.

"I like her, but I don't know if I am in love with her."

"That's fine, but before you go doing everything she wants, I want you to try some pussy first. How about next week? I don't have anyone coming in next week and I would love for you to try some pussy."

"You are going to have sex with me?" My eyes opened wide as I felt a rush of excitement that I was actually going to be able to have sex with Liz. I wanted to tell her for a long time that I wanted to have sex with her and now she is just offering it to me like it was a piece of candy.

"Ohhh, no not me. Donna has a thing for you."

"She does?"

"Ohhh yea. She loves the shy innocent boys. She has been asking about you the moment I said you were a virgin."

"Nooo...please no. You didn't tell he that I was a virgin...did you?" I shot back feeling both guilt and embarrassment. My heart hurt as if the wind got sucked out of me.

Liz put her hand on mine and then pulled it towards her. In a calming motion she stroked my hand and forearm. "It's okay to be a virgin. I think you should be with someone that you love the first time. I would hate for you to pop your cherry on a girl you had to pay for. I mean other guys yes, but I want something special for you."

"I feel bad though...I mean will she think less of me? Do you?"

"Ohh please...no. I broke in so many college kids that were virgins, I lost count. My whole business was created on breaking in virgins. But I would like you to be with someone that is really into you. Donna has a thing for you and I told her that she can have you first. She has a thing for acting like a mommy during sex and you are exactly what she wants."

"She really likes me like that?" I asked wondering how I got mixed up with two separate girls that want me and what I was going to do about Donna and Jeri.

"If you like Donna than go for it. If you want cock, and that's you're thing then go for Jeri. If you want both then that's okay too, and you should tell them that. I just think you should have some pussy before you go head first into what Jeri wants."

"I guess, I can do that." I replied feeling more at ease with what Liz was saying but still excited about Donna wanting me.

I went back down stairs after talking with Liz and listened to how she was going to rent out the place and that I was kinda stuck in the house now as I would not be able to stay at the other house near the college. I felt fine about it as I thought about making money and then going back to college without any worry for money.

I texted Jeri the good news and then read that she was excited and that she would be packing her things today and would be here tomorrow. I wondered what her real plans were and that I was not being used. I felt somewhat at peace knowing that Liz was there and would protect me if something did go wrong.

I heard a knock at the door to the upstairs and wondered who would knock as Liz always just walked down. I called for them to come in still wondering if it was Karen or Donna now.

I saw the leather outfit and knew it had to be Karen. I then saw the devious look on her face and then realized she wanted me in her video.

"Are you ready? I have the script that the guy wants. I just need you now. Liz is already drinking lots of water and is ready for her part."

"Ohhh...okay." I answered knowing that I was about to be in some kinky porn video.

"You don't have to say anything...matter of fact, don't talk at all. All I need you to do is moan. I will fuck you with the toy doggy first and then move you over to your back. When you are on your back Liz will squat and pee on you."

"I guess." I said wondering if the toy was huge and having a few second thoughts.

"Good...see you upstairs." Karen replied in a chipper voice as I then heard the clicking of her hells on the steps.

I went to the bathroom and did what Jeri instructed me to do before anal sex and then washed myself up the best I could. I put on simple shorts and a shirt with no panties though.

I went upstairs and saw Karen by her room motioning me to come in. I walked in too see a giant suite setup for video calls. Electronics and computers were everywhere as the large room looked packed out. I instantly knew that Karen was no joke.

The other half of the room looked girly and was made up to look like a teenager's room though. It was like half the room was an electronics warehouse while the other half was a kids room. Karen had to be in her late twenties but her room did not match her age. I figured it was her set and that she played off being eighteen.

"I am going to say some mean stuff, but please don't take anything I say personally. I will be using three different toys on you, but I will make sure you are properly stretched before going to the big one. Ohh...but the way, did you clean yourself?"

"I did, and how big is the toy, how long is this video?" I asked wondering how big of a toy I was going to get fucked with and for how long.

"Maybe forty five minutes, but I can go less. We can cut it short if it starts to hurt though. I will only be using the big toy for a minute at most. Trust me, you will be fine. As long as you are open, the last toy won't make much of a difference."

I looked around and saw they strap-on she was going to fuck me with and felt worried. The three toys were black and lined up on the table in order of size. The first one was very long but thin. Jeri's cock was wider, but not as long as the first one. The toy looked like a real black man's cock and had a slight curve to it.

The second one was both long and was wide. I instantly could tell it was way thicker than Jeri and was smooth with only the tip looking like a real cock. I never took anything in my ass that wide or deep and instantly felt scared about it hurting.

The third toy had me really worried and I felt like saying no the more I looked at this monster thing. It was well over a foot long and was so wide and thick I was shocked that it was even made for human use. It was wider than a soda can and was longer than any real cock I had ever seen in the movies.

"I don't know about this." I spoke up worried about both the second and third toy and how it was going to fit. I felt duped but didn't want to say anything either for fear it might upset her and Liz.

Karen gave me a soft smile again as I knew she was convincing me not to say no. "I will be gentle and work you up. Trust me you will cum from it too. Once your ass is worked up, anything can fit in it. I have done this before and you will be fine...trust me."

I nodded my head feeling like I was stuck and that I had to say yes. I knew I needed to relax, but I still knew it was going to hurt.

"Good, we can start in just a few moments. Would you like a hood to cover your face or do you want the man to see who you are?"

I looked at the black leather hood that was covered in zippers and knew that I did not want to go that far. "Noooo...I can go without it. Is just this guy going to see it?"

"He will own the video and might upload it though. I doubt he will though, but there is always that chance, that's why I am offering the hood."