My First Job

Meeting customers on my first job

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.



I crawled up next to her, "I'm sorry," I said. She smiled at me, I wanted it, and I liked it. Now you've had all of me. I kissed her, I can't believe we found each other. Annie looked at me, I know that you are the best gift that I've ever been given.
Am I a gift? I don't understand how you can say that, you've done all the giving. She said "Thank you." I looked at her, maybe we can go out to dinner? She asked, "Are you sure? We might end up the talk of the town."
Get dressed I'm taking you out for dinner, Annie smiled, she liked being told what to do. We both washed up and dressed, I drove out of town to a restaurant that no one would know us. Dinner was nice, we talked, Annie had wine, I didn't even ask for a drink, I didn't want to be embarrassed.
I asked her about her history, how she landed here, it was boring but I enjoyed it. I gave her my whole past in five minutes, one job, no girlfriends, never been in trouble, but I'm happy, she watched me and smiled.
We finished dinner, Annie was tipsy, we drove to her house and got ready for bed. Annie had a T-shirt on, I tried not to touch her breast, but she wrapped her arms around my neck. I'm too tired and sore, Annie said. You know I never say no to you.
I smiled, let's go to sleep. I woke up alone, Annie was making breakfast, I ate and went to the Piggly Wiggly. I was really early, the deliveries were ready, so I started loading my truck. I heard my name called, I turned, it was my manager.
"Jack, we need to talk," I was confused, I've never been called into the office, I walked in and she shut the door. She looked at me, what time did you start work yesterday? I looked at her, "I'm not sure, but I wasn't late." She looked at me, you came in at 10:30, loaded your truck, and started delivering.
Jack froze, maybe she found out that he had sex with his first delivery, he started to panic but remained quiet.
She looked at him, your timecard said you came in at 12:00 and you left at 6:00, you keep making more deliveries, but your hours are the same. I was quiet, she said, I don't expect you to work eight hours and only get paid for six.
I looked at her, "I call in to see how many deliveries I have and if I have to come in early I do. I don't speed, I don't want to get a ticket, and I know you need the deliveries completed."
She walked over to me, put her hands on my arms, in five years I've never questioned anything you do. I ask you to do something and you handle it. She looked into my eyes, I trust you, you are a great employee, but you are working two jobs, and now you're putting more hours in here, and you are looking very tired.
I smiled at her, she smiled back, I almost hugged her. I was relieved that I wasn't getting fired.
She started talking again, I want you to clock in when you get here and clock out when you finish, I want to pay you for all your working hours. I felt overwhelmed, I looked at her.
"This is my first job, you were my first boss, I love this job. Five years ago you gave me an opportunity, I appreciate all the help and direction you have given me. I don't care about the money, I don't want to disappoint you, you have never disappointed me.
I looked at her, she had a tear in her eye, she hugged me. Then she whispered in my ear, "I'm your boss, you can work nine hours a day, without approval," but, you looked tired. I depend on you, I don't want you to wear yourself down. If I see you looking tired again, I will send you home.
She pulled back and kissed me on the cheek. Are we going to have a problem? I smiled, "No, you will never have a problem with me".
She turned me towards the door, you had better go. I walked out of her office, one of my friends asked me if I was okay? I answered, "I think so."
I got in my truck and called Annie, she answered, I told her I was called into the office, and what happened. Annie laughed, "O my God, stay away from her, she falling for you. If you want to keep your job, stay away from her."
I told Annie I don't think so, we're good friends. Annie was quiet, I'm going to have to lock you in the basement, I unleashed a monster. Don't look any more women in the eyes, stare at their feet. "I hope their feet are not as sexy as yours," Annie asked, should I call in an emergency order, I can take you in one of the empty rooms.
"No, I have too many deliveries." Annie laughed and said goodbye.
I started my deliveries, I knew most of the customers, too bad Ms. Adams isn't on the list. My first two were easy, the third a little farther out, it was two sisters, they were always friendly. I carried in the boxes, they both followed me with their eyes. I never took notice of my deliveries, now I watch them, some of them watch me.
I started to leave, one of them came toward me with a tip, wait a minute, she grabbed my arm, do you want lunch? I looked at her, she was smiling, I looked her in the eyes, I have too many deliveries, or I would enjoy having lunch. Next time we'll have a warm lunch waiting, she handed me a tip.
I thought about the sisters while driving, the talkative one had a great body, she had her top unbuttoned, all I could think about was her nice cleavage. They were both attractive.
I finished the deliveries, it was a long day, I thought about my talk with the store manager and Annie's comment. I never thought about her as a lover. Too many things are changing, life is getting complicated.
Annie greeted me at the door, she kissed me, "How do you feel?" Do you want a shower before we eat? I said no, I'd like to have dinner. There were packages on the table, and these are for you, shirts, pants, socks and underwear. Now we don't have to wash clothes every night. I looked up at her. Thank you, but I was going to go shopping as soon as I had a moment.
Annie laughed, just spend your time with me, it makes me happy.
We talked while we ate, I said, "Life is getting complicated," she smiled, "I'll keep us, simple." Annie keeps me grounded, she has all the answers, being with her keeps me calm.
I showered after dinner, Annie joined me, she kept me hard during the shower. After we dried, she led me to our bedroom, lay down, I'll take care of you. I was hard, she straddled my hips and lowered herself onto my cock, she watched my face. My cock touched her lips, she was wet, the tip slid into her.
She had a smile on her face, I'm adjusting to the size of your cock, she moved up and down, the fat head was moving in and out of her pussy. The she stood up and turned away from me, she slowly lowered herself onto my cock, I was buried in her. Annie started rocking her hips, slow, then fast, I came fast, in large spurts, she didn't stop after I filled her my cum.
Annie looked over her should, do you think you're finished? I smiled, she stood up and turned around, she leaned over and kissed me, how do you like me fucking you? I wrapped my arms around her neck and kissed her, "You like to say fuck, don't you"? She laughed, well I didn't make love to you, I just wanted to fuck you, so you could relax.
Annie kissed me, let me put you in my mouth, I want you hard again. I stopped her, please just stay up here, I need to get some sleep, I'm exhausted, she rolled next to me and we slept.
I slept until the morning, when I awoke, Annie was still next to me. I was hard but didn't start poking her. I started squeezing her breast, a low "Ow," escaped her lips, I pulled her nipple. Annie just lay there on her back. I squeezed harder, I pinched her nipple, her hand went to her crotch, she rubbed her clit. Annie wanted an orgasm. I enjoyed watching her hand between her legs.
Annie's orgasm was intense, when she finished, her hand pushed my hand off her nipple, "Stop." It was getting late, I had to bake at the nursing home, I showered and drove to the nursing home, Annie followed me.
I started baking, I talked to Annie but kept our distance, she watched me while I baked. She was my boss, I asked her if I could have breakfast, the residents finished eating. Annie walked me over to the eating area, I filled a plate, she brought me a cup of coffee, she sat with me while I ate.
She handed me a list of what was needed for the upcoming week, I looked at her, anything new you want me to try? Annie just smiled, I don't have anything else I can teach you. I started getting hard, I couldn't respond.
I was unaware of the fact that Annie had asked for a room to rest during the days when she worked 6 AM to 6 PM, she kept a change of clothes and toiletries. The management readily provided her a room, they knew she worked long hours and they didn't want her driving home when she was tired. She managed the kitchen and the dining room.
She told me about her room, gave me a key and told me to use it anytime I needed it, I smiled. Is it a single bed? She looked at me, do you want me to show you the room? The cleaners clean it every day and change the sheets. I couldn't stop what I was doing, so I asked for a rain check.
I had to start deliveries at the Piggly Wiggly, I didn't have many deliveries, and was hoping to get out early. I wanted to show my manager that I had a lot of rest and wasn't tired, she was concerned.
I clocked in at the Piggly Wiggly loaded my truck, and stopped at my manager's office. She knew I was there, she could see all the doors on the closed circuit TV. I knocked at the door, she told me to come in.
I told her I had a good night's rest, breakfast at the nursing home and felt great. Jan stood up and came over to me. I hope you didn't think I was talking to you just as a manager. I looked at her, "You were right, I was pushing too hard and stressing about baking at the nursing home." Thank you for talking to me like a friend.
Jan reached for my hand, I looked at her and smiled, she pulled me closer. You're young, can I ask what your next career move is? I was wondering if you thought about your future. I was surprised, she asked, "Have you thought about college?" As usual, I was speechless.
Jan continued, the parent company has a program that pays for your college, while you work and attend school. I hope you don't mind but I met with Annie, your other boss, and told her about this program.
I was in the program, I attended a college about 45 minutes away, online courses and in-class, it took me five years, but I have a degree in business and business law.
You probably wonder why I never talk about a boyfriend, well, I never had time. I love managing this store and I appreciate what the company has done for me, it was a long, lonely process, but it paid off.
She wrapped her arm around my waist, don't say anything, come back if you have questions. Jan stopped, remember I will help you any way I can, I am your biggest supporter. I stopped and looked down at her, I just looked into her eyes.
I said, "We'll have to talk after my mind catches up."
I left to do deliveries, I knew Jan watched me leave. My truck was loaded, I left, I called Annie as soon as I was on the way. She answered, I said hi, I'm leaving to do deliveries, she was silent. I waited for her to talk. Finally she said, "Don't fuck your boss." I said, "You mean again?"
Annie was silent, "Did you just have sex with your boss?" I laughed, I thought you meant you, you're my boss. Another pause, then she said, did you and Jan have sex? Well boss, no, I did not have sex with my other boss. I think Annie smiled, she started talking, Jan came over to visit, she talked about you and your future.
I said, I know, she talked to me in her office, we had a talk, and I left to do deliveries, that was ten minutes ago, now I'm talking to you. Now, I am going to hang up and you are going to feel better and make up for your attitude when I get home. Annie said, wait, "Thank you for calling, and don't talk to Jan unless you have to, I'm sorry."
My deliveries went well, I didn't have any of the customer's paw at me, but a couple of possibilities. I finished, went to the store and clocked out. I wanted to get home before Annie.
I washed up and was sitting on the couch when she walked in. Annie didn't look at me, she came over and sat on my lap. I'm sorry for my attitude, I really thought you and Jan fucked.
You should quit talking, you've already earned a spanking. Annie stood up and started to strip, she turned, her ass was in my face, only use your hand. I kissed each cheek, these puppies are too pretty, I wrapped my arms around her hips and buried my face between her cheeks. She squealed, stop I'm sweaty from working in the kitchen all day.
My tongue slid down her crack and hit her asshole, Annie struggled and pulled out of my arms, don't do that, she turned and pushed me back, she straddled my lap. Her hands went around my neck, "I created a monster." I laughed and tried to kiss her. She pushed my face away, "Your face is stinky."
I laughed, you'd better kiss me, or you won't get another kiss all night. She tightened her grip around my neck and pushed me back, then her mouth covered mine, her tongue pushed against mine. A soft, slow kiss, she pulled back are you happy? Then she kissed me again, her hands still around my neck, "You've made me very happy these past days. I don't want anything to change."
I looked at her, we had a nice night out when we went to dinner, can I take you out again? She smiled, that would be nice, but I have to shower, and you have to wash your ass mouth. I answered, "We'll shower together," Annie pulled me up, let's go.
Annie was taking charge again, she was naked, I followed her ass to the shower, I started getting hard. I stripped, Annie was standing next to the bed, she looked at me, then walked over to the nightstand. She looked at me, can I use KY? I nodded.
She put some on her fingers and reached between her legs, her fingers disappeared into her pussy. She walked over to me and grabbed the head of my cock and covered the tip with KY. She knelt on the edge of the bed, she had a smile on her face, come over her.
I was behind her, she reached between her legs and guided the tip to her pussy, "You can gently fuck me." My hands went to her hips, the fat tip, pushed the folds of her pussy into her. She pulled away but I held her hips and pushed into her. Annie is a moaner, she tells me my cock is too big, but she never wants to stop, she's likes to talk during sex.
I pulled her back and pumped in and out of her, I looked down, most of my cock was buried in her. Her head lifted and she lurched forward. Annie rolled on her back, spread her legs, she opened her arms, come here lover. I stepped up and started fucking.
I buried my cock in Annie, she watched it disappear into her folds. I held her legs up by her ankles, Annie hadn't had an orgasm yet, but I was ready to cum, I was in her deep, a few short strokes and I emptied my balls into her. Normally she would ask me to stay in her, tonight she crawled to the middle of the bed.
I crawled next to her, I asked her if that was enough, she just smiled. You are too much for one woman, we slept.
In the morning we started with breakfast, Annie always changed the breakfast up, it was different everyday. I was picking up weight, Annie commented, you are starting to fill out. I left for work before Annie, she was slowing down.
I knew I had extra deliveries, I clocked in, went by Jan's office to make sure she knew I clocked in, she jumped up. I asked her if I look rested, she came over to me and said I looked great, I told her I was eating better and putting on a few pounds. She put her hand on my chest, you feel solid. I hugged her, she felt good in my arms, I left to do my deliveries.
My first two deliveries were in the same building. I remembered Ms. Adams, she got frisky and gave me a big tip. I decided to deliver her second, in case we had a repeat of the first delivery.
I carried the groceries to the first apartment, Ms. Ames. She answered the door, I've delivered to her before, a nicewoman. I carried in the groceries and put them on the table. She looked at me, smiled and asked me if I was delivering to Ms. Adams.
I looked up, "She asked me to take her groceries until she comes home. I'll sign for them."
Ok, I'll bring them up, and headed for the door. I carried in the rest of the groceries, kept them separate from hers. When I went for signatures, she smiled at me, her hand went to mine, she squeezed and said, "I expect Ms. Adams at any moment, could you wait a few minutes." She pulled out a kitchen chair. I sat down, I looked up, she sat on my lap.
I was quiet, she kissed me. I froze; my arms went around her hips, she kissed me again, soft and slow.
I looked at her, I'm not sure I have the time to wait for Ms. Adams. She started to unbutton my shirt, stood up, and pulled me up. Her hands moved to my belt, I looked at her, she didn't hesitate, she undid the buckle. I had been thinking about Ms. Adams, I was semi-hard.
I unbuttoned my shorts and unzipped the zipper, she pulled them down. She could see the huge bulge, she looked up at me and dropped to her knees and pulled down my underwear. Her head went back and she looked up. I thought Ms. Adams was exaggerating, her hand went to my fat cock.
Before I met Annie, I might have froze, but I put my hand on the back of her head and pulled it to my crotch. She guided the head to her open mouth. I was looking down, I started pumping my cock into her mouth. She pulled her head back, stood up, dropped her shorts and top. She was naked in a minute.
She threw her arms around my neck and kissed me, a great, long, sexy, kiss. My hands move to her hips then her ass, smooth, round, mounds of ass. She gave me a little moan, she grabbed my hand and led me to a bedroom, she crawled to the middle bringing me with her.
I wrapped her in my arms, like I hold Annie, then rolled her on top of me. Her legs were spread. She reached down and pushed my cock so it was between her legs, she clamped her thighs around my cock.
We kissed and pumped our hips, I rolled her on her back, and pressed the head of my cock between her legs. Her hand guided it to her wet lips.
She grunted when I pushed it into her, I pumped, they were short strokes. I pulled the head of my cock out of her then back in hard, I did this a few times then pulled out of her.
I moved my mouth down towards her crotch, I wanted to excite her with my tongue. My mouth covered her clit, I sucked it gently, her hands were on my head. I moved my tongue along her slit, gentle licks, then kisses. She grabbed my head and tried to grind against my mouth, I teased her, and then let her grind against my mouth. Her orgasm came quickly.
I moved back up to kiss her, she was smiling, I kissed her and pushed my cock between her legs, her hand guided me back into her. I felt her pussy lips against my cock, pumped my hips and I was in her.
She opened her legs and raised her knees, I slowly pushed the head of my cock into her. Her arms and legs wrapped around me. I wanted to fuck her and leave, so I started pumping my hips. The walls of her pussy were tight, I looked down at her face, her eyes were closed and her mouth open.
She was noisy, she froze and started shaking, this was her second orgasm, her arms loosened. I slowed down, lifted and looked down at her, I pulled slowly out of her. Wait, you're not finished, don't stop, she tightened her arms and started pumping her hips.
I felt the mattress move, I looked and Ms. Adams was laying next to us, naked. Her hand went to my ass, I could feel her pushing, "Fuck her Jack, she really wants all of you in her pussy."
I started pushing into her, she pulled my head down and we kissed, her arms held my head. I started fucking her, she moaned. "Oh God." I just kept pumping into her. I was ready to cum, I fucked her, my whole cock was in her, I've never fucked anyone this deep or hard.



I started cumming, she was tight I pumped hard, I held on to her while I came, I heard her whimpering, "Oh," she kept moaning. When I finished, I looked down at her, I was still pumping my hips, I kissed her, she held my head and kissed me back.
I lifted up, I looked down at her, half my cock was in her, my hand went to her crotch, I massaged her clit with my thumb. "No, that's enough, my pussy hurts." Ms. Adams reached over and grabbed my cock and started stroking me.
I pulled out of Ms. Ames, Ms. Adams leaned over put my cock in her mouth, her lips closed around it. She sucked it, her hand pumped it in and out of her mouth, I pushed her on her back. She held onto my cock and pulled me with her. She looked at me, "I was afraid I missed you."
Ms. Adams was tiny, she pulled me by my cock, I had to be careful I didn't crush her. "Come over here Jack," she said, as she tugged on my cock. I smiled at her, her body was luscious, and she was cute. She was a small woman, I knelt between her legs, her hand grabbed my arm.
She pulled me down for a kiss, her arms wrapped around my neck, I looked down at her and said, "Hi." She laughed, "Are you going to fuck me?"
She never let go of my cock, she pulled her knees up and positioned my cock against the mouth of her tiny pussy. I've been thinking about you, I hope you enjoyed being with Tina, I knew she would keep you occupied. I pumped my hips, the head of my cock pushed into her.
She smiled, that's what I was waiting for, that fat cock. She pulled me down, you really used me the last time, I pushed deeper, should I stop? She grunted, "No, I won't let you."
This was sex, she talked to me, moaned in my ear and pumped her hips. I felt her tighten, "God this is good." I never stopped pumping into her, she had an orgasm, I felt her body tremble.
I heard her moan, "Wait," She kissed me, I pulled out of her, the head of my cock was pressed against her lips, I pumped my hips, I heard a load moan escape her lips. Jack, stop for a minute. I kept fucking her, she didn't protest, she was torn between resting and cumming again.
She started pumping her hips, she was taking me deeper, her channel was adjusting, I forced my cock deeper, she wasn't sure what to do. She pushed my shoulders, it's too big, please pull it out of me. I could barely walk after your last visit, "It was a great fuck."
I looked down, she looked up at me, you can cum in my mouth, I rolled from between her legs. She sat up and moved her head towards my crotch. She grabbed my cock, looked at me, don't hurt my mouth, she stroked me with both hands and sucked me. I pumped my hips, I know I was hitting the back of her throat, I put my hand on the back of her head.
She was enjoying sucking me, she pulled her mouth off my cock and smiled, I pushed her head back down. Ms. Adams looked over, "Let me make him cum," she straddled me and started lowering onto my cock, Ms. Adams held it and guided it for her. I was amazed that they weren't shy or ashamed.
Ms. Ames had half my cock buried in her, she was rocking on me, her hands on my chest. She was trying to cum, I started cumming. I pumped my hips, shot my first spurt and fucked hard, I finished in her. My cock started shrinking, she rocked on me until she came.
She fell forward on me and laid on me. Finally I she rolled her off of me, Ms. Adams grabbed mu cock, it was wet and soft. "I said, "I have to go." She put it in her mouth and sucked it, she had half of it down her throat, I couldn't stop her. I was enjoying it, I was hard.
I pushed her down and laid between her legs, pushed my cock in her, she wrapped her legs around me and we were fucking, she was tight. She held on to me, she and finally had an orgasm, I came next. I lifted off her and started dressing, both women were laying in bed when I left.
I hurried and finished my deliveries, I made it back to the store a little after 7:00 PM, I clocked out at the right time. Jan was still there so I said goodnight, she popped up and said hello, and added, "We are going to talk soon." I smiled and left.
I called Jan earlier and told her I'd be late. When I got home we ate. I asked her if Jan talked to her, I told her I saw her and she wanted to talk. Annie smiled, you can't ignore her, I'll have to make sure I drain your balls before you see her. I looked at her, please take this seriously, I don't want to lose my job and I won't have time to go to college.
Annie looked at me, should I tell her we are sleeping together?
I looked at Annie, maybe you should say we are having a relationship and you love me. Annie looked at me, I think you are stressed and tired, let's eat diner, we'll soak, relax, sleep and you can have anything you want. I looked at her, do you think that will help me?
Annie said, "It will put you at ground zero, I'm not sure where we'll go from there, but this relationship, that's you and me, will be here no matter what."
I smiled, "Thank you, I can live with that." I helped Annie serve dinner, she told me to sit down, I pinched her ass, and said "No."
We finished dinner, Annie had a glass of wine, then I poured her another. I asked her why she isn't wearing her at T-shirt, she giggled, striped and sat there bare ass naked. I looked over at her, knelt in front of her and pushed her legs open. I am very sweaty, could you wait until after we shower?
I kissed her knee, and her thigh, then the inside of her thigh, I pulled her hips closer to the edge of the chair. Annie put her hand on my head, grabbed my hair and pulled my mouth towards her pussy. I could smell her musky odor, I kissed her mound. She put her feet on the edge of the chair, and pulled my mouth to her pussy. My open mouth covered her clit, my tongued licked her, she opened her legs wider.
Her hips tilted and she started grinding against my mouth. Her other hand went to the back of my head, my head was trapped, she started grinding against my mouth and tongue. Annie was smiling, her hips rocked, she started an orgasm, she relaxed and then pulled my mouth up to her. You don't have to kiss me, I said. Annie smiled, I like pussy breath and we kissed.
It was a nice kiss, soft, she called me pussy breath, I answered, I never called you dick breath. Annie said, I never made you kiss me after you cum in my mouth. Thank you, I said.
Would you put your cock in me? I'm ready. I lifted up, she reached down and guided me to her pussy, I pushed into her. Her arms wrapped around me, I slowly fucked into her. We kissed, "Hard, you know I like it hard, let me take all of that big cock."
It was a slow deep fuck, I fucked her hard, she moaned and grunted, "Oh God, make me cum," I did. She had a loud orgasm, I kept fucking her hard, she had a few more orgasms, then she felt me getting ready to cum. In my mouth, cum in my mouth, I pulled out of her, stood up and pushed my cock in her mouth. She wrapped her arms around my waist, I pumped my cum in her mouth, she just sucked me until I was soft.
She swallowed, and kept swallowing, she kept my cock in her mouth. She looked up and was smiling, she pulled her head back and my cock slipped out.
Annie sat down, could you get me a glass of wine, a large glass? I walked to the kitchen and poured a tall glass of wine, when I brought it to her she smiled. She took a mouthful and swirled it around in her mouth. Is that how you taste wine, I asked? She smiled, I am rinsing my mouth, so when we kiss, you won't taste cum.
We went to bed and fell asleep.