My New Job Ch. 02

I wanted to say yes to the hood but could not get the fact the leather hood made it too weird for me. "I can go without."

"Ok, just bend over and let me put some lube in you. Just in case the lube I am using wears out."

I pulled down my shorts and bent over on the girly bed she had and felt a syringe pop right into my ass and then felt a cold rush as she injected my ass with enough lube for days of fucking.

"Pull up your shorts and we can start." Karen said just as Liz walked in wearing nothing but thong panties. Her large breasts hanging down taking my attention.

I pulled up my short and Karen gave me a soft sweet look. "Thank you again for doing this. I promise I will make it up to you"

Liz took my hand and moved me over as Karen messed with the computer. "If it hurts too much then just say...I am done. If you say stop or anything else we will continue. The safe phrase is, I am done. I also drank a lot of water and my pee should not be too bad. If you don't want the big toy, that's okay...I think it's excessive but Karen insists that the client is demanding it."

I nodded my head to thank her as I tried to calm my nerves. I figured that Karen would stop if it got too bad and Liz would never hurt me.

"Okay the moment I put my hand up we can start. Remember, everything I say is what this guy wants and nothing is directed at you. When I shut the camera off it will be a wrap and we are done. This guy is a cuckold and likes to imagine his wife is fucking black guys and that some of the black guys want to fuck him. He comes home and she is going to fuck him using black toys while degrading him and Liz is my sister who is pissing in your mouth to make you feel worthless."

I nodded my head and Karen flipped on the camera and then Liz walked around to aim it at her. Karen slowly put on the strap-on while looking at the camera. "So...you want to fuck me. I don't think so. I only fuck big black guys and the last guy said he wanted to fuck you. Now I need to make sure your ass is ready for some black cock."

Karen then looked at me. "Strip you worthless fucking sissy. Strip down and let me see that small pathetic dick of yours...not even a dick but a sissy bump."

I pulled down my shorts and bent over to where Liz was pointing to, so my ass was now facing the camera. I then heard Karen flip the cap on a bottle of lube. My mind was thinking about the time Jeri fucked me and the size of the first toy was nothing and I could handle it.

I felt the tip of the toy against my rectum but only slightly like it was going to enter me but didn't. "I am going to make you feel like what I felt when he fucked me with his black cock. You're going to feel what it's like to be fucked by a real man...a black man. Make you a BBC lover."

"Ohhhhh." I moaned softly as I felt the tip penetrate me. It was slight but it was in past the tip. She sunk it deeper as my ass muscles easily adapted to its normal size shaft.

"Ohhhh...it slipped right in. You fucking slut...I knew that you were fucking gay and now this confirms it. This cock slipped right in like you were some gay whore. I don't fucking believe it...your ass is used to black cock." Karen hissed as I felt some guilt knowing that some of what she said was right, I did have Jeri fuck me and I liked it.

Her hands were now on my hips as I felt her bury the toy right up to the base in my ass. I breathed slowly and relaxed just as Jeri told me to as Karen rammed the toy in my ass.

She pulled out slightly and then rammed it deep in me again. "Such a sissy bitch...I bet you're liking this black cock. I bet if a real black cock was here you would have him fuck you. I bet you would make the best prison whore too."

Again and again she slammed home in my ass. Her fingers gripping me as I felt her toy push deep in my ass. My anal muscles were relaxed as I felt I was open for business to be fucked as there was no resistance as she slid deep in me again and again.

My soft limp dick sway back and forth as her waist slammed against me ass. I could hear her grunt from the thrusting as my ass took each inch of the toy like a champ. She was pounding me harder as the pressure from the toy in my ass felt good now.

"My black boyfriend is going to fuck you sooo good too. He cums so much too, feels likea hose going off in my twat. He wants to give me a black baby too. You are going to love feeling his back seed deep in your sissy ass too. His warm black spunk is deep in me right now and tomorrow he wants to fuck you hard. I need you to take him deep and love it."

Karen was pounding me relentlessly and my ass felt so open. I was happy that I was feeling only pressure as I heard the lubed toy tunneled in my ass like a drill. There was nothing I could do but take each thrust and stay calm making sure I did not clench up.

Karen then pulled out and I felt the loss in my ass from the missing toy. I knew right then and there that I was gaping. I heard about assholes that gape after anal sex and now I was experiencing it. My rectum was stretched open and staying open like it wants more.

I heard Karen putting on the other toy. And then felt the cold lube enter my ass like water being poured down an open drain. "Now I am going to open your ass more. Some black cocks are bigger and I want you to be able to take all black cocks that want your sissy white ass."

I thought it would hurt more and I thought it would take more effort for the second toy to enter me. It popped in quickly as I moaned. "OHHHHHHHHH."

I could not help it as she slid the monster black toy in my ass. My soft dick began drooling sperm. I was orgasming from just it entering me. I closed my eyes and felt the stinging pressure of my anal muscles being stretched far beyond its capacity.

It was like pain and pleasure were mixed together. The pressure and slight pain of being stretched was now converging with the absolute pleasure one gets from anal sex. My prostate was being nudged with no real skill as the toy was just that large. I was weak from the intensity of having such a large object in me and without any real pain to the sheer size of it.

My penis was dripping face like I was being milked, as Karen was slowly fucking me with this black monster. Her hands were on my hips as she pushed in and out with a slow but steady pace.

"You're doing great... your ass is going to please so many men. After they are done fucking me they can get a taste of your tight ass. Mmmm...yes baby...these cocks will be fucking me first. You are going to have to watch as each black cock fucks me and maybe impregnates me...you just won't know which black cock did the deed."

She was going at the same pace as I felt just so open and weak. I don't think my penis could cum any more as she pushed in and out of me. All I could feel was pressure from the size of it and then pleasure of it being so thick in me."

"Roll over you slut. My friend wants to know if you are as weak as I say. She just fucked man and needs you to clean her cunt out."

Karen withdrew out of me and the loss of the toy from my ass was so noticeable. I felt stretched open now even more now that it was out of me. I rolled on my back and watched Liz walk over to me and then squat right over me face.

"Kar...do you mind if I go to the bathroom first before he eats me out?"

I knew it was coming and my heart was racing. I remembered her pissing on me before and the thought of how erotic it was now sent tingles throughout my body. I stared right up at her pussy lips and inhaled her female aroma coming from her sex and then watched her open her pussy lips letting me right a nice good close up of her pink entrance.

"Please...you don't even have to move." Karen said calmly as I knew I was seconds away.

"Open up." Liz remarked as I opened my mouth.

I felt the stream of piss hit right on my tongue. I watched as her piss seemed to be aiming right at my mouth like she had control over it. The taste of her salty girl urine was there but not strong but flowing fast into my mouth.

"Be a good boy and swallow all that piss...that it. Gulp it down like you want more." Karen called out.

Liz's piss stream was not going fast but not slowing down either. I gulped it down tasting her pee. I tried to keep my mouth open but when I swallowed I could feel her warm piss just hit my lips. I opened up quickly to take more of it in letting it fill up my mouth only to swallow again.

I could feel my asshole being stretched. Something large was trying to enter me and all I could see was Liz's cunt lips as the last of her piss trickled out into my mouth. I swallowed quickly only to have her pussy lips drop down demanding I lick them.

The pressure was immense like I was being ripped open. I want to scream but could only moan. Something was entering me that just seemed not to fit. I knew Karen was now using the large toy and I could do nothing but try to relax. I focused on licking Liz's piss flavored pussy as I felt my anal muscles just stretched and stretched until the pressure was almost unbearable.

I moaned into Liz's cunt as the muffled sound of my discomfort was dulled. My ass felt huge as something was entering me. Then all of a sudden I felt it slide in me. I could not believe it. The monster toy was in my ass. The pain was there as was the pressure and discomfort of something so big.

"Your ass is destroyed now bitch. Every guy will know you're a faggot sissy. When they slide their black cocks in you they will know you are made for this." Karen commented as I felt her sliding it in and out of me.

"I am done...I am done with your pussy." I said wanting it to end but not wanting to fuck up her video either.

I then felt her slide out of me as Liz's removed her pussy from my mouth and from my view. Karen then helped me up as I saw the giant sized toy in her hand.

"Go clean up from the men who are coming."

I nodded my hand and then Liz waved her hand down as she flipped a switch on the camera. "And we are done." she said.

"You did great...I hope it wasn't too bad." Karen said as she put the toy down next to the other ones.

"It hurt." I said as I stepped forward a bit.

"Go lay down. I will come down stairs with some pain pills in a bit." Liz said as she moved in and gave me a soft kiss on my lips.

"Thank you...you did great too. You did a great job and ending it too. I won't have to edit much too. I owe you." Karen said as she kiss my lips harder making me feel her tongue inside my mouth and sending sparks of excitement through my body.

I walked to my room feeling the dull ache in my ass. It was a nagging pain and I still felt open from what happened. I made it to my bed and fell face first breathing in hard as I knew I needed to say just like that.

A few minutes later the pain began to get more and more intense. It was like my ass was trying to close up and then act of going back to normal was painful. I regretted the last toy but the first one was okay.

I could hear the door open and the creak of the steps. I turned my head to see Liz hold a glass of water. "Here...take this and I will check on you later."

I took the few pills and drank them down as I saw Liz was wearing a shirt now but her hanging breasts still got my attention. I saw her smile once I took them. I smiled at her and felt a peace as she seemed to care about me and would be there if I said no to the whole thing.

"Karen said that you did great and the next time you can get half the profits. Apparently the client pays well and you could make some serious money. I don't have a client until next week and will be doing some filming of my own soon and though you could help with the filming part."

I felt a bit woozy but nodded my head. I had no idea what she was saying after the filming part and all I could think about was sleeping. I saw her get up and then everything went black.

***

I woke up naked and on my back. I had the blanket over me and had no idea how long I slept for or who undressed me. I then got up and heard the television shut off.

I saw Donna come around and into my view. Her blonde hair was down and looking curly and she was wearing a tight sundress with no bra that showed off her breasts making them look huge on her thin frame.

"Baby...you got to rest." she said in the calmest soothing voice.

"How long was I knocked out for?" I replied not fighting back and leaned back on the bed looking at her.

Donna was like Karen in the small petite frame department, but while Karen had small breasts, Donna was well endowed. She was not as large as Claire but she was larger than Liz. Donna also has a pretty face that looks like a mom that was ready to drop her kids off at school. The makeup was there but done lightly and nothing she wore was extreme.

"It's been almost 2 days. I wanted you to rest and heal up. Your friend from school came by and dropped her stuff off. She should be back tomorrow too."

"Jeri?" I asked not knowing and then wondering why Donna was almost talking in code.

"That's her name...yes. She will be back tomorrow. Now that you're up, I can I teach you things."

"Teach me things?" I asked wondering if she was going to have sex with me and hoping it was just that as my butt was still a bit sore.

"Of course baby...mommy is going to teach you about girls and what they can do for you."

Before I could think of something to say Donna pulled down the top of her dress revealing her large breasts to me. I was in awe as she stood there smiling at me while her heavy tits were hanging there waiting to be fondled.

Donna's face just had that down home look of cuteness about her. Her face had soft gorgeous lines about it and her smile seemed to melt my heart. With her breasts now out I could not resist myself and felt my erection come on. My heart was beating fast as I figured I was about to experience sex for the first time where I penetrated a girl.

"Mommy's going to make you feel all better too." she said as she leaned down pulling the blanket off of me.

I knew that Donna had a mommy thing and I was not one to stop the role-play as the sound of her voice seemed to entrance me to believing it. When I saw her pull down more of her dress showing me her blue lace panties I had a brief flash that this gorgeous creature in front of me was my real mother.

I watched closely as she pulled down her panties revealing her sex to me for the first time. Her neatly trimmed pubic hair made me think of a older woman too even though she was young. She then knelt down taking my member in her hand. "I can see that you are already excited so I won't have to do it myself.

She gave my dick a few strokes before I watched her get up and lift her leg over my body. She then moved down so my erection was against her belly. "Now, mommy is going to show you how girls need boys. I just need you to do everything I tell you to do."

I nodded my head as I looked at her smiling down at me as if I was doing everything right. I dreamt and masturbated to the thought of being with a girl and now it was going to happen. Not only was I about to have sex, but the girl I was going to be with was so beautiful. It didn't matter that she was acting like my mother as I felt that it only added to the erotic act of sex.

I once again nodded my head in agreement as she then got up and took my shaft in her hand and aimed it right towards her opening. I waiting for only a split second before the most unbelievable sensation engulfed my dick. It was both warm and tight while being wet and slippery all at the same time. It was like heaven opened up and took my penis. The sensation was the most amazing thing and I opened my mouth in total shock to the feeling of being inside of her.

"Good boy...you're nice and hard for me. Now I want you to stay that way while mommy shows you what she can do." she said smiling at me.

I watched her body grind her hips and then lift her body slightly only to push down against me. The feeling of my dick moving in her only added to the wonderful tight gripping sensation her pussy was giving me. It was like wet soft slick surround my dick and moving. Like a warm massage that was all over my shaft.

My eyes looked at her as she moved faster. Her breasts were bouncing and swaying as she was riding me. My hands went to her hips as I felt her snug pussy massage my male organ. I then let it get tighter and wetter and then release me only to do it again and again.

My eyes were locked on hers and then she smiled back. "Your doing good. Ohhhh yes...my boy is doing good. You feel mommy's pussy pleasing you?"

I nodded my head as the feeling of being inside of her was like nothing else I ever experienced in my life. Each movement was so astounding as I felt her warm tightness clench me each time. She was bouncing but not slamming down as her steady rhythm was making my cock throb like nothing else.

"Now...when you feel you have to pee...don't worry. It's your orgasm. This is mommy's special time of the month and I need you to finish inside of her."

"What?" I said knowing that I was breaking the role-play. I need to answers as I realized that she wanted me to cum inside of her bareback. I knew she was mentioning that she was ovulating and now I wondered if she was on birth control.

"Shhh...it's okay. It will feel great when you release in mommy. Just do as I say and let go. Mommy will be fine...just finish deep in her. Your stuff will make mommy really happy and give her a big belly."

I did not know if she was doing this as her fetish or she was really serious. I was inclined to believe that she was serious but then I thought quickly that it was just her acting. I kept up the acting and let go of my fears.

"Thatssss...it...I feel you readddy. Just finish..OHHHHHH." she moaned as a snug tightness around my shaft. It was like she was trying to push me out and yet her weight was pushing me deeper.

My cock was throbbing as I felt her sex muscles grip me. The tip of my dick was getting all of this attention as she clamped her cunt muscles on me. I wanted it to last but felt I was about to cum. It was different than masturbating as I was not in control and the soft wet massaging sensation on my prick was overwhelming.

My muscles were getting tighter as I knew I was seconds away from finishing. I wanted it faster and yet I was not in control. Donna looked down at me with the warmest smile as she now was slamming her body down on me.

"Do it...do it in mommy... give me a baby. Cum deep in me and give my pussy a nice baby."

I gripped her hips and then felt a surge in my body. My orgasm was there and Donna slammed him pinning me down as I had no choice but to ejaculate deep inside of her. The feeling of cumming in her was nothing that I could have imaged before. This was not be jerking off by my hand the orgasm was intense and yet passionate.

I wanted t pull out and wanted to push deeper. I had this urge to push deeper like my cock demanded it be as deep as possible as I felt my cum surge inside of her. Over and over my warm cum was shooting off and all I could do was try to push it deeper. Donna was smiling at me as I felt her cunt clamp down and hold my shaft in place like I was locked in.

"Ohhh fuck." I moaned as the last of my fertile seed was shot off in her.

"You feel better now?" She asked still looking down at me smiling.

"That was so amazing." I answer as I knew I was being honest too.

"Good I hope so. I wanted to be your first." Donna commented as she took a deep breath but kept her body still on me as my member was still deep in her.

"I guess thank you then. I hope I was good tough." I asked not knowing if I should have lasted and also thanking her because it was really good.

"Ohhh, you were fine. I came a bunch of times too. Did you want to do it again?" She asked as her smile seemed to make me think that she was the most beautiful thing on the planet.