After Hours at Self Checkout Ch. 01

Reader's Note: This is the first time I ever tried writing a sex story. I have been an avid reader of literotica for about 6 -- 8 years now (I know I should have started writing my sick fantasies down years ago). But it seems that life circumstances are calling upon my overactive imagination that has been subdued. So now it is reawaken and now it is time to share itself with the world. No longer will my stories and tales be locked up in my brain. I also want do what many writers have done for me: to give you stories that either arouse you or send you into orgasm. This is the first of many gifts that I want to give to a community that has entertained me over the years.

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It was a late night and I was sitting beside a mini heater monitoring a self checkout. A self checkout at one of those grocery stores that thinks staying open until midnight makes sane sense. It was another one of those nights that I was getting frustrated. Because not only was I doing an eight hour shift standing at self checkout, my front runners in all their infinite wisdom didn't think to relieve me for a break, and I had already gone seven hours without a break, and seriously had to use the bathroom at this point. I was going to make a call to customer service to get my break despite how much they complained. That is until a tall, sexy black woman walked into the self checkout. She was carrying a blue shopping basket full of cereal, milk, and bananas.

As for myself, I am shorter than average, black, and skinny. I was wearing some black slacks and a blue vest on top of a white buttoned up shirt with my name tag where my heart is. This chick has a skinny body with a nice pair of tits. Her slender, yet bodacious figure was accentuated in a sleek black dress. Dark hair was down to her shoulders in soft waves. Her makeup was done to highlight her eyes and wore shiny purple lipstick. As she rang up her items she was staring at me intently. I found her glare to be pretty striking, but I kept quiet because I was kind of enjoying the attention. She wasn't paying attention to what she was doing, so I had to aid her when the machine started signaling for assistance. I walked up to her and rechecked the items on the scale with those scanned. I found she didn't weigh the bananas.

"Sorry, but you didn't scan the bananas." I said sternly while taking them out and placing them on the scanning scale to weigh them properly. I then proceeded to try to key in the numbers.

"Oh, sorry. By the way what is your name?" she asked as I was putting the bananas in the bag.

"My name is Darrel." I said while pointing to my name tag before walking back to my post.

"Such a cute name. When do you get off?" she asked with a sense of curiosity in her voice.

I was taken aback by her deep voice, but what I was more confused about was why I she interested in a guy like me. I am not bad looking, I just come off as kiddish to most due to how weird I am.

"I get off at eleven." I said nonchalantly as I got close to my heater.

"You are almost done: you have an hour left. Do you have a ride home?" she asked getting money from her purse and paying for her groceries.

Now I was deeply flustered that this woman was so interested in me that she was willing to give me a ride home. But then I realized that allowing her to do so could lead to something. Honestly, my life wasn't getting anymore interesting. Working every evening at self checkout was making me thirsty for a change in life.

But instead I plainly responded, "No, I walk home."

Upon telling her I saw her face deflate for a second, but then brighten back up shortly afterward. I could see the gears turning in her head as she was trying to come up with more to say having finished her purchases. If only she knew I was enchanted by the idea due to boredom induced curiosity. I would have accepted any offer she mustered all in the hope of a change. After grabbing her things she walked up to my post and went really close to me.

"I really think you are cute and want to take you home with me tonight." she whispered seductively.

My eyes widened in disbelief as the reality of what was happening was sinking in. Being seduced was honestly turning me on.

"If you wanna have some fun tonight. Just come to the side parking lot. I will be waiting in a red 2006 Honda Civic. And just so you know I am packing heat." she said while lowering her tone.

My eyes widened at what I just heard before looking her straight in the eyes.

"Hope to see you later; don't keep me waiting too long." she said waving me a quick good buy.

It took me a couple seconds to realize I was being hit on by a black transsexual which to be honest is such a major turn on. I always had a thing for transsexuals, but never had the resources to pursue such a dream.

My mind was racing right now; I couldn't believe what had happened and what could happen if I took her up on her offer. My palms were literally sweating and my heartbeat was speeding up. My anxiety was taking front seat and it was scaring me. So much so that I was literally having a hard time standing at my post at self checkout, so I started pacing the floors of my six self checkout machines.

By 10:50 my mind was continuing to race as I started shutting down the terminals and putting up the closed sign. After I handed in my till, I finally went to the bathroom briefly before heading out into the cold night. As I walked towards the side parking lot I was hoping to god that she was joking when she said she would wait for me. When I turned the corner to the side parking lot I found her red 2006 Honda Civic sitting in the fairly empty parking lot. She spotted me and flickered her lights to signal me. I walked to her passenger side and knocked on the window. She immediately gave me a sexy smile before unlocking the door from her side. As I got into the passenger seat she stared at me while chewing on her bottom lip.

As soon as I closed the door she grabbed the bottom of my chin and stared into my eyes deeply sending my anxiety to the max. I was about to back off out of fear until she quickly shot her hand to my back to stop me from backing away. That's when a look of shock hit my face as I looked her in the eyes. She smiled at me making it clear she had control and that I was going nowhere.

"Not so fast, honey, I am not gonna let such a cute thing like yourself slip away from me." she said before her lips smashed into mine.

Out of shock I opened my mouth and let her tongue slip in my mouth. I was only going with her invasion of my mouth due to the fear and arousal that was taking over my body. My mind started flooding with all the things I could do with her. This resulted in me getting bolder and reaching one hand for the back of her head for leverage so I could get deeper into the kiss while my other hand reached for her breasts. When she felt my hand on her chest she moaned into my mouth before breaking away from me.

"Oh, God! Now we're talking, little boy! I love to have my tits played with by my new toys. You better get used to them because you are gonna be doing more then just touching these babies." she said squeezing her other breast.

She returned to kissing me furiously before her hand moved for my crouch which was getting hard at the moment. Her feeling up my stiff cock brought on a moan from my lips. This made her become more aggressive with her hand. She pulled away from my lips and focused on stroking my dick.

"You like that, don't you, little boy!" she asked seductively.

I let out another moan and started playing with her tits harder. That brought out a surprise moan from her lips.

"Damn, Darrel, you really know how to turn a girl on. And for that I wanna give you a reward!!!" she said while pulling my hand away from her tits.

She then adjusted her dress to let her breasts hang free. I stared at them in a trance like state. When she saw this she smiled and put her hand on the back of my head and pulled my mouth to her right breast.

"Now get to work and start sucking. Remember, I told you that you were gonna be doing more then just fondling these babies." she said in an oddly demanding, yet soothing tone.

I tweaked her nipples with my tongue before sucking them hard. After a couple minutes she put her hand up my shirt and started tweaking my nipples. This was actually a shock to me because I was already so aroused. I let out a quick whimper out of shock and this made her laugh in response.

"Somebody has sensitive nipples, I have a lot of plans for these, but I want to get to the main course. I have been aching to have a piece of you since I set my eyes on you." she said grabbing my hand and putting it under her dress.

When my hand met with her erection, the gravity of the situation actually set in: I was actually touching a penis. For some reason I become more aggressive with my sucking of her nipples and without hesitation pulled her panties down and started stroking her big, fat, 9 inches of cock. She sensed this increase in aggressiveness and stroked the back of my head.

"I see I have awakened a little cock slut in you. We are gonna have so much fun!" she said sliding my pants and underwear to my knees and stroking my 6 inch cock.

I know I should have been embarrassed at being so small in comparison, but a desire of wanting to service her was taking over my mind. It was as if her aura was making me submit to her. After a while of this she pulled me off her breasts and took my hand away from her cock leaving me wanting more. By this point she knew I was under her spell and I would do anything for her.

"Now it's time for you to take my fat cock into your mouth. Keep your mouth open: I want see your hungry face ready to get fucked." she said getting the rest of her dress down her knees. Now that I see her full view I can see her nicely toned abs.

When she was ready she was reclined in her car with her cock in her hand glistening in pre-cum. She saw me slowly inch over her and decided she wanted to test her control. She wrapped her hand around the back of my head and dove my open mouth on her dick. I gagged due to the quick motion. Luckily she allowed me to adjust before using both her hands to face fuck me. I wasn't prepared for this and was gagging all over her cock. This made her smile even more.

"I am sorry for that, but your dedication to my lovely cock inspired me to just take charge." she said reclining her chair back even further so that she could get more comfortable.

I moaned as I started to create a suction with my lips and suck her dick as she drove her hips into me.

"Oh yes, baby! You are sucking me so good! You love being my cock sucker. Don't you." she proclaimed.

I simply responded by nodding and looking up at her so our eyes met.

"I can't believe I have found someone as cute as you. You know what, you wanna be my boyfriend?" she asked pulling my head away from her dick so I can speak.

"Yes, I would love that!" I said before diving my head right back down to continue my sucking.

"Thank you, we are gonna have so much fun!" she said excitingly.

She had taken her hand from my head when she realized I didn't need to be forced. I focused on the tip of her cock causing her eyes to slip into the back of her head as she moaned loudly. I started to taste her pre-cum flowing from her tip. In order to keep her from cumming too quickly I drove my lips down her base until the head of her cock was at the entrance of my throat. I could feel my gag reflex reacting in response, but I tried my best to swallow. This resulted in me pulling her cock head into my throat.

"Oh my god!!! You are throating me!!!" she moaned while stroking the back my head.

When I got her into my throat I just swallowed the best I could causing my throat to constrict around her cock.

"You are torturing me. I want to cum on your pretty face so badly." she said pulling me off her cock.

I positioned myself as she grabbed her dick and started using my saliva to stroke herself. I watched intently as she focused on stroking the tip of her cock.

"I am gonna paint that pretty face of yours with my cum. You ready!?" she said hastening the stroking of her cock.

"Yes please, give me your cum!" I said opening my mouth and letting my tongue stick out with anticipation.

"I'm cumming!" she moaned shooting ropes of cum across my face. One shot sprayed across my open tongue as the other shots landed across my cheeks, the bridge of my nose and across my closed eyes. When I felt the stream finish I opened my eyes and saw her staring at me with labored breaths.

"You look so cute and slutty with my cum decorating your face." she said wiping some of her cum from my cheek with her finger and sticking it into my mouth.

"You taste so good." I said after gladly sucking her finger clean.

"I am so glad you think so because after today we are gonna be doing so much more." she said reaching for my cock which had been aching to be touched.

After some stroking she wrapped her lips around me and started sucking me like pro. She was moving so fast I could hear the slurping sounds she was making.

"Your mouth is amazing!" I moaned.

When she felt I was wet enough she pulled away from my cock presented her beautiful tits to me.

"I want you to paint my tits with your cum." she said enveloping my dick between her breast while sucking the tip.

I took the hint and started tit fucking her. She immediately met my thrusts with her tits and mouth.

The combination of this chest to mouth action was quickly pushing me to orgasm.

"I am gonna cum!" I screamed.

In response she quickly put her finger in her mouth reached around under my ass and found my asshole. Without hesitation she struck her finger in my hole causing my body tense up as my cum rushed out of my tip and painted both her face and her tits in my cum.

"Now we are even." she said scooping some of my cum from her tits and sticking it into her mouth.

I looked at her intently, realizing that I didn't know this beautiful woman's name.

"You mind if I ask what your name is?" I asked. She gave me a confused look on her face before realizing she didn't tell me.

"Sorry for that. My name is Tammy. I feel so embarrassed now taking you without even telling you my name, I gotta stop getting carried away like that." she said genuinely feeling guilty.

"Don't worry. As long as we both had fun that's all that matters." I assured her in response.

"Thanks, I think it's late. I should probably take you home." she said cheerfully putting back on her dress.

She was showing me a more sincere side of herself and this was so much more attractive than the aggression act she was playing before.

"Why don't I go to your place and we can get to know each other better?" I offered.

Her eyes widened up as she turned on the ignition of the car.

"I would like that, but don't you have to be home?" she said in a concerning tone.

"No, I live alone and I wouldn't be doing anything special if I went home anyway." I reassured her.

"Ok, that works. I live alone too, so it would be great to have company." she said pulling out of the empty parking spot and turning onto the silent road.

My life was about to get interesting and I was looking forward to it.