My First Job Ch. 02

I met an older woman named Annie, she was the Chef at a nursing home I delivered groceries to. I delivered groceries a few times a week, I was also the baker at the Piggly Wiggly market, the store I delivered for. Annie, the chef, hired me to help her bake for the nursing home.

I made a delivery one Friday, my last delivery, Annie invited me over to her place for dinner, she said her home cooking was spicier and tastier than the food at the nursing home. It turned out that she seduced me, it was her plan from the moment she saw me. After sex and after dinner and after more sex, Annie wanted to discuss what happened.

Annie admitted that she was attracted to me, but she thought I was older and more experienced, she did not think I was a virgin. I couldn't remember how many times I came that first night, but I was sure she had more orgasms than me. I wasn't sure what point Annie was trying to make. I was hoping this wasn't a farewell talk.

I interjected, did I disappoint you? Annie looked up, she smiled, I told you that I enjoy your company and I like you, I was hoping you felt the same. I smiled, I enjoy being with you; the first time I met you I couldn't take my eyes off of you, you're sexy, pretty, and you weren't even trying. I stopped and you have a really nice ass.

Annie smiled, so you're not upset that I'm older and I took advantage of you? I leaned over and kissed her, I don't consider this being taken advantage of. This is beyond any fantasy I could dream. Annie kissed me, can you spend the night? I thought about it, "Normally I don't spend the night out, I'll call my mom and tell her I won't be home."

Annie looked at me, she smiled. Then she stopped to think about what happened, she wondered, would they be able to go out together? Would it last a few months, and then he would realize that he didn't have a future with Annie? Then Annie remembered how she felt when she was with him, he made her happy and provided great sex.

Annie stood up and grabbed my hand, I stood up and we kissed, she led me to the bedroom, we lay in bed and kissed. I was gentle; Annie wrapped her arms around my neck, I was excited.

Lying in bed with a naked woman was new to me; everywhere her body touched mine could have given me a hard-on. Annie moved my hand to her breast, I gently squeezed.

Annie's eyes closed, pinch my nipple, pull on it; her hand moved to my cock, she wrapped her hand around the tip, "God you're big." I'm glad Annie was in charge, she threw her leg over my hips, she guided the tip to her pussy. I pushed into her, she grunted, "Oh God, you really fill my pussy." I rolled on top of her, she opened her legs.

Annie pulled my face down and kissed me, her legs wrapped around my hips, "Hard, I want it hard." I pushed into her, she grunted, her hips started moving, I pumped into her hard. Annie wrapped her arms around my neck, she whimpered and groaned.

Annie's orgasms were noisy during her first she whimpered, and then groaned, I didn't stop. She lifted her knees to her chest, "Deeper," then, she smiled. She put her hands on my chest and pushed me off.

I pulled my cock out of her, she rolled and went to her knees, her ass was in the air, I wasn't sure what I was supposed to do, but I knew where she wanted my cock. I fucked forward. I buried my cock in her, her moans were muffled by the sheets, I could feel the walls tighten, I pulled her back against my hips. Annie's body shook.

I knew this just was fucking, Annie was enjoying my cock. I finally pumped my cum into her, I was exhausted and breathing hard. Annie fell forward, I fell on top of her, my sweaty body pressed against hers.

My cock was still in her, I rolled off of her, Annie said, "No more tonight." I laughed, "Maybe just one more." Annie looked at me, "You'll have to find a hole that's not sore," I blushed and then I laughed.

Annie wanted to know more about me, and what I did for fun. It was easy and simple. I was 19 never had sex, never a long-time girlfriend, and was a hard worker. I explained what I did at the store and all the jobs I learned, I told her I love to bake. She asked me how I started delivering groceries.

I explained it was out of necessity and that the nursing home was my first delivery. Annie asked me how the customers treated me, I smiled; they were very nice, they offered me lunch, and gave me tips. Annie asked if they ever put their hands on me, I thought back, a few of the women put their hands on mine, or my shoulder. Annie looked at me, I'm surprised I was the first that had sex with you.

I looked at her, sex never crossed my mind, I wouldn't want to lose my job. Annie laughed, if they only knew how big that bat your swinging is, I wouldn't have been your first. I was surprised. I looked at Annie, I've never thought of anything but doing the job. Annie smiled.

Annie, looked at me, the next time one of them touches you, look them in the eyes and smile, you'll get bigger tips, but don't tell me if you have sex with them. I looked at Annie suprised, I don't think I'm changing anything, I want to keep my job.

I've never had those type of thoughts and I'm very happy with you, this has been the best night of my life.

Annie was just smiles, if anything happens, I'm sure you won't get any complaints, I turned away from her. Do you really think those women would have had sex with me? Annie laughed, like I said, the next time one of them touches you, do what I said, look in their eyes and smile, but don't have sex with them. I looked at her, you mean smile like this, she said, "Stop it."

We talked for awhile, we eventually fell asleep in each other's arms. During the night I woke up with a hard on, I pressed it against her back and slid it down to her ass cheeks. Annie laughed, "My pussy is swollen and sore." She turned and faced me, she reached down, wrapped her hand around my hard-on. Do you like this? Maybe my hand will work, I can jerk you off, she smiled at me, would it help if we kissed?

I kissed her, it certainly helped, her mouth was soft, her tongue teased mine. Her hand was soft but it wasn't as soft and wet as her pussy.

Annie put my hand on the top of her head, "Push my mouth down, force your dick in my mouth, make me suck it."

I slowly pushed her head down, I felt her breath on the head of my cock, I pushed my hips up, her mouth was closed tight.

I held her head with my hand, I guided my cock with my other hand, the head pressed against her lips. I pushed hard, her mouth opened, my cock was in her warm mouth. I pushed her head farther down.

Her mouth slid down the shaft, I was in her throat. I held her head and fucked her mouth, she grunted when I hit her throat.

It felt better than her pussy, she sucked hard and used her tongue, I shot my cum in her mouth, I felt her swallowing. I held her head and kept fucking, she choked but didn't pull back. I was finished, my cock was getting soft, she pulled her mouth off my cock, and finished swallowing my cum.

She sat up, looked at me, when you want me, just fuck me, I want you to take me whenever you want. She lay next to me, I wrapped my arms around her and we fell back to asleep.

I woke up, Annie was not in bed, I smelled bacon and eggs, I walked into the kitchen, she had the t-shirt on. She put her hand up, let me finish cooking, I laughed and went to get coffee.

Annie served breakfast, I put my hand on her back, and said thank you. Annie looked at me, "Eat your breakfast."

I had to go to the store and do the deliveries, I started early, hoping I would finish early. My first stop was an apartment, I carried the bags up to the door and knocked. The door opened, she was standing there in a T-shirt. I stopped and just looked at her, I had delivered here before. Hi Ms. Adams, she smiled, she grabbed one of the bags from me, her hand squeezed my arm.

I remember what Annie said, I looked into her face and smiled, she squeezed my arm tighter, let's put the groceries on the counter. I turned to the door, "Wait, I may need help." She opened a cabinet door and reached for the top shelf, her T-shirt lifted above her ass, her bare cheeks peeked out. She spun and looked at me, I can't reach the top shelf, she saw me staring.

I carried the bag over to her, she handed me a large can. Can you reach the top shelf? I stepped up behind her, I easily put the can on the top shelf, I felt the palm of her hand rubbing the front of my pants, I was already stiff. I stood there and let her feel my cock.

She turned and looked up at me, "Wow, that's a surprise." She pulled a chair over to the counter, "Let me see if I can reach it with the chair." I helped her step onto the chair, she reached up, her t-shirt hiked up and her tiny ass was exposed again. I had to look, she peeked over her shoulder and saw me staring at her pretty ass.

"Oops," she said, I couldn't talk, she spun on the chair, "Help me down." I tried to help her down, but didn't know where to put my hands. She grabbed my hands and moved them to the back of her legs, and then moved them to her ass cheeks. "Squeeze them, they're firm."

She was right, my hands covered her tight ass, my fingers reached into the crack of her ass, "Your hands feel good on my ass."

She bent over and kissed me, a little peck, her tiny hands held my face and kissed me again, my mouth opened. Her tongue touched mine, she moaned into my mouth. She lifted her lips off mine, "Is that okay?" My arms tightened around her waist, her legs wrapped around me, I held her in my arms, "Put me on the table."

I walked over to the table and lowered her down, she weighed nothing. She pulled her T-shirt over her head and laid back on the table, putting her feet on the edge. Her hand reached between her legs, she rubbed the tiny patch of fur. She smiled at me.

She moved her hand to my mouth, I could smell her pussy, "Taste me." She pushed her fingers into my mouth, my lips closed around her fingers, my tongue teased her fingers. "Please lick me." It's lucky Annie taught me how to eat pussy.

Three days ago I would have not known what to do. My face move down, I kissed her belly button, my tongue swirled around the edges. Her legs opened, she pushed my head down, I kissed her mound.

My tongue touched her slit, her hand grabbed my hair, I teased her with my lips and tongue, I used my hands to spread her thighs, I was surprised at how wide her short legs spread.

She tried to press my mouth against her tiny pussy, I let the tip of my tongue tease her, I looked up, she looked at me and smiled. Her hips were moving, I covered her slit with my mouth. The flat of my tongue pressed against her, her hips moved, my tongue was rubbing her clit. She stiffened and tried to clamp my head with her thighs, I held them open, that was her first orgasm

She finally quit moving, I gave her a few more licks, she jerked when my tongue touched her. She pulled me off her mound, with the she hand in my hair. She pulled my wet face up and kissed me. "Wow, who taught you that?" I didn't answer, I'm sure she didn't care.

"Lift me off the table". I easily lifted her off the table, and let her stand; her hands went to the button on my shorts. She was staring down, all I could see was the top of her head. The zipper went down, she pulled my shorts and underwear down.

I was hard, she stepped back, "Oh my God, how did you hide that?" I smiled, her hand grasped the head, her fingers couldn't cover it. I lifted her up. I remembered that Annie always said, "make me take it." Her arms wrapped around my neck, we kissed, I tried to lower her onto my cock. "I'm too small," she said.

I laid her back on the table, I took her hand, and put it on the shaft. She looked up, stretch me. I pushed into her, the spongy tip spread her lips, I looked down, she was smiling. Her hands squeezed my wrist, her hips were moving, she was trying to take my cock deeper.

I looked down, the head was in her, I pumped my hips, her legs wrapped around my waist, we were moving in unison, she was taking my cock. Her hips stopped moving, "Ow, you're hurting me." I stopped and started to pull out.

Stay in me, it feels good. I'll stretch, just go slow. I slowly pumped into her, her face changed. She was really tight, I fucked faster, she started an orgasm, my thumb found her clit, and I gently massaged it. She had a long orgasm, it shook her body. I kept pumping into her, half of my cock was in her, I started to cum.

She felt the first stream, her hips started moving again, I kept cumming, she felt the hot streams splash in her channel. I fucked deeper. I finished and laid on top of her, she kissed me, I was only half hard, she didn't move. I pushed deeper into her with my half hard cock.

She was smiling; keep fucking me, it feels good. My cock was deep, I was getting hard, I started pumping. "Stop you're too big." I slowly pulled out of her, my cum was running out of her.

I looked at her, I have to get back to work, she looked at me, maybe you can come back after work. I looked at her, I doubt it, I'm behind.

She stood there naked, her thighs opened, a gob of cum hit the floor. It was running out of her and down her thigh, she looked down, I'm a mess. I felt you cum, you flooded my insides.

"Kiss me goodbye, until the next delivery." I bent to kiss her, she wrapped her arms around my neck and kissed me, she looked at the name tag on my shirt, "Jack, wait a minute," she came back with $50, here's your tip, I looked at her, that's a big tip. She looked at me, I'm sure you'll earn many more. I left her, I thought to myself, I should have washed up, I smell like sex.

My next few deliveries were easy, not as much fun, but easy, I was behind in my deliveries, I called Annie around 5:00, I told her I was still making deliveries, I thought you went in early, she saud. I laughed, I did, she just gave me more deliveries.

Annie laughed, are you coming over? Just call me when you are on the way, I'll have dinner ready. I paused, "Thank you, I'm sorry."

Hey, I'm sure you'll make it up to me. I didn't know what to say, "I'll be your slave." Annie responded, "No, I like being yours." She hung up.

I finished the deliveries and drove back to the Piggly Wiggly, I turned in my paperwork. That was a lot of deliveries, I told the manager, she looked me with a strange look. She said thank you, I just smiled. I went to the bathroom to wash up, I still smelled like pussy, I hope she didn't smell me.

I drove to Annies, I should have stopped at my house for clothes, and let my family see me, but my priorities have changed. Annie has changed me, now that I've had sex with Annie and a cute little customer. Now I know I have a big cock, life is good.

I walked in, kissed Annie, I need a shower, is that ok? She smiled and said, not a problem, do you need anything washed? I smiled, are we going to work up an appetite? Annie was standing there in her T-shirt, I said, I really enjoy looking at you, my hand went to her bare ass. Thank you, she said and she kissed me, now take that hard-on to the bathroom.

I walked to the bathroom, and showered, after dinner, I went home to get clean clothes, Annie didn't want to take a ride, I guessed she probably doesn't want anyone to know that we're a couple.

I brought my dirty clothes back to wash. I sat next to Annie on the couch, I kissed her, I love you in that T-shirt. Annie pulled the T-shirt over her head, I like me like this. I looked at her, you know what's going to happen now? She smiled, "Surprise me."

Annie was beautiful, I stood up and stripped, she reached for my soft cock. I've never seen it like this. Annie, leaned forward, opened her mouth, her hand guided the soft cock. She looked up at him, her tongue tickled the head, he started getting hard.

Annie pulled his cock out of her mouth, she started stroking it, her arms wrapped around his waist. She thought the big cock felt good in her mouth.

Annie enjoyed being with him, he was a nice person, she was teaching him how to be a real lover, he had all the tools, maybe she was falling in love or maybe it was lust.

Annie looked up, you know I can hardly walk, you've stretched my lady parts. I looked down, I don't have any control, especially when you're naked, You like me hard. Annie stood up, she wrapped her arms around my neck, we kissed. Her hand went down between us, she spread her legs and positioned my cock so it was between her legs.

I was quiet, we kissed, she clamped her legs around my cock, and started moving her hips, "Squeeze my ass, I want to cum." Both hands went to her ass cheeks, I squeezed hard, and started pulling her against me.

I watched her face, her smile changed, I felt her legs squeeze my cock tighter, she let out a low moan, my fingers dug into her ass, "Harder." I fucked harder, she kissed and bit my neck, she sounded like she was choking, then I felt a warm flow over my cock.

"Stop," she groaned, Annie was hanging onto my neck, she pulled back, I was no longer between her legs. I looked down, her juices were running down my shaft, onto my sack.

Annie just hung around my neck, I tried to kiss her, "Wait, I can't move, she looked up at me, I can't fuck yet." I just held her.

Finally, she grabbed my hand and led me to the bedroom, she walked to the nightstand and opened the drawer. She reached in and grabbed a tube, she unscrewed the cap, grabbed my hand and squeezed the tube, I had a gob of KY jelly on my finger.

Annie grabbed my hand and used my finger to rub the KY on her crinkled asshole. She stood there, "Gently, rub my asshole," she said. I rubbed the KY over the tiny, wrinkled hole, she grabbed my finger and pushed the tip in. She knelt on the bed, her ass facing me.

I had a surprised look on my face, she looked over her shoulder, "Push it deeper," I hesitated, she reached behind her, grabbed my hand and pushed my finger into her ass, past the 2nd knuckle, then she pushed it in even deeper. My fingers are thin, but long, she used my finger to fuck her ass. She smiled and looked at me.

I knew what anal was but never considered it or thought about using Annie's ass. She pulled my finger out and wrapped her hand around two fingers, and then she pushed them back into her ass. She looked at me, "Do you want my ass?"

I stopped, I don't think I can. Annie looked at me, she reached behind her and grabbed my hardon. She smiled, "So, you think you can say no?" I just looked at her, "I'm not sure what the right answer is." She guided the head of my cock to her puckered butt hole.

Annie was breathing hard, her body was flushed, I pushed my hips forward, Annie pushed back, she pushed back until the head disappeared into her. A loud moan escaped her lips, her head dropped.

My hands went to her hips, I pulled her onto my cock. Annie fell forward, she rolled onto her back, and lifted her knees, she exposed her asshole to me.

I stepped up, I looked at the crinkled little hole, Annie, you're ass too small. Well, I want it. I pressed my cock between her ass cheeks, I leaned forward, my cock disappeared into her. Annie was smiling, ow, it hurts, slow, go slow. I wanted to pull out but her ass felt too good, I kept fucking into her.

I leaned forward and, reached for her breast, I squeezed them, her hand went between her legs, she started rubbing her clit, I looked down, her hand was moving fast, her mouth opened, the noises she was making were making me fuck faster. I came in her ass, my whole cock was in her ass, Annie was grunting and her eyes were watering.

I leaned over and kissed her, she said, "Pull your dick out of my ass." I laughed, "Not yet, it really feels good."

Annie said it's burning and it hurts.

I slowly pulled out of her. She rolled onto her stomach and crawled into the middle of the bed. Are you okay? Ow, she said, am I bleeding? I was alarmed, I bent over to look, she pulled her ass cheeks apart, air escaped. Annie laughed, "Oops, sorry, you did that," I looked, lots of cum but no blood.