Winners And Losers 2

This is my entry for the 2019 Halloween Contest. Please enjoy and if you do, please vote. Thanks.

As always, my characters involved in the sex are all over the age of 18. Since this is my fantasy, there are no STD's or unwanted pregnancies. All of my characters enjoy good hygiene so showers are only mentioned when part of the sex. They also eat when needed; none of my characters go hungry.

The names have been changed to protect the not so innocent.

I am a loser. At eighteen years old, that was my assessment of myself. My father left us when I was much younger. He told Mom he couldn't deal with a kid like me. Even then I had too many issues.

I am a loser. My mom gave birth to me when she was only fifteen years old. I certainly was not planned. Just another accident.

I am a loser, standing six foot two and weighing 205 pounds with a well-developed body, I could be a shoo in for a starting position on any football team in the state. I can't be bothered with sports. Not as a participant nor even as a spectator.

I am a loser even though I am considered to be good looking according to my mother and her friends. I don't have a massive cock but it is a good size and suits my frame. I am afraid to talk to girls.

I am a loser, so if everything came out equal, I would like computers or reading or just watching TV. Some such shit. Well, I don't.

I am a loser, I am a chronic masturbator. My favourite masturbation fantasies involve my mother. All those fantastic looking women out there and I am only attracted to my mother.

But this story involves me becoming a winner for a change.

Using basic arithmetic, Mom was only 33 years old at the time of this writing. To me she looked much younger. Maybe in her mid twenties. When her parents passed away she was left a modest inheritance. Mom bought herself new boobs and enrolled in college. There was enough money in the bank to see us through until she was able to pursue a career.

Mom did not date. Most of her time was spent at home with me or in the library studying. When she went out, it was generally me as her escort. Our outings included dinners at her favourite restaurants, touring local museums, or just long walks along the rivers' shores.

Mom had insisted throughout the course of my high school years that I participate in differing school activities. I put up resistance to this idea over the years, mostly losing.

The only club that she did not have to push me hard to join was the Special Occasions Club, usually called Socks, in my final year. The reason for that is they had more girls than guys in the club and the women tended to be fantastically hot. Despite the name, the club held meetings slash activities monthly. The meetings were always held off school grounds at a local restaurant that had a large enough backroom to hold us all.

The main reason I enjoyed the club was that the members were mostly great looking seniors. Of course, since my fear of approaching women ruled my life, I could only watch them. Besides, most of them had boyfriends anyway, even if they were not accompanied by them. I could still admire them though. And masturbate later thinking of them.

There had been a surprise at our Labour Day meeting. The current President of Socks had resigned from the club due to school pressures, she needed to focus on SAT's and such.

The newly elected president had the nickname Prinnzess due to her haughty attitude. Unlike her predecessor, who was fairly laid back, Prinn was an autocratic bitch most of the time.

She announced that there were going to be changes in our monthly meetings. Each meeting was to be more of a party than just a get together. Each party would have a theme. And participation would be mandatory.

Anyone not willing to take part in the event would be drummed out of the club. Prinn was looking at me when she made the announcement. She also mandated that everyone attending would need to bring a date. Prinn was still staring at me when she said this.

Our next meeting would be Halloween. It was to have a Mardi Gras theme. Formal clothing and half masks were to be the costumes. Obviously, since I had no date to bring, I would not be attending nor would I remain a member.

I told Mom about the change in leadership of the Socks and the new membership criteria. Mom thought that would make a startling difference to the tone of the club and felt that the changes would be good for all.

The weekend before the next meeting slash party, Mom asked me if I had done anything about a costume yet.

"No, Mom, I haven't since I won't be going."

"Why not?" she asked. "It could be a lot of fun."

"I have no date, Mom, and I can't attend without one."

"Can't you ask someone out for the occasion?"

"Moooom, you know I can't. I don't want to be turned down by anyone, anyways. No one that knows me would want to go with me. They all think I am a nerd."

"Honey, that's not right, you need to confront your fears and ask someone."

"No, Mom, I am not going," I said as I left the living room and went to my room.

A couple days later, I was still messed up about the whole party deal. Mom must have noticed my mood.

"Why so glum, chum?" she asked.

"Just the usual shi—stuff. The party is next weekend and I still haven't anyone to go with."

"Have you asked anyone, Honey?"

"No, Mom," I growled.

I stormed out of the room, returning to my bedroom and slamming the door behind me. Mom knew better than to ask a question like that.

Sometime later, there was a knock on my door. Of course, it had to be Mom.

"I was thinking of pizza for supper," she said. "Want to go to Domini's?"

"Yeah, I guess."

The restaurant was busy when we arrived but not full. Mom attracted a fair amount of attention upon our arrival. She was dressed in what she considered to be one of her college girl outfits.

Her big store bought D cup boobs were in a tight T-shirt, a mini skirt that could almost be called a belt, thigh high socks, and high heels. Of course I thought she was looking amazing and so did many of the male diners.

We were sitting at the table waiting for our drinks when we were approached by one of my classmates. A football player who seldom even acknowledged my existence, he was also Prinnzess' boyfriend.

"Hey, man, how you doing?" he asked me.

We exchanged the required pleasantries with him looking down at Mom.

"Who is your date, Rick?" he asked.

Before I could correct him about her being my mother, Mom piped in.

"My name is Tessa," she said.

"I didn't know you were seeing anyone," the dumb jock responded. Of course he did not know since he knew absolutely nothing about me.

"We have been seeing each other for almost a year now," said Mom.

"I don't remember ever seeing you around school," commented the dummy.

"Oh, that's because I graduated two years ago. I'm at Conestoga State now," said Mom, naming the local college.

"Wow, a college girl. You're a lucky guy, Rick."

Just then the waitress brought us our pizza. Mom said he needed to excuse us, we wanted to eat while the food was hot.

"I'll see you next week at Socks," he said in parting.

As he left the restaurant, Mom started to laugh, with me following.

"He really thought I was your girlfriend," said Mom with a giggle in her voice.

"I should go to the party with you next week", she said.

My mind quickly jumped to thoughts of Mom and me being on a date. I would be able to put my arm around her, dance with her, and maybe even kiss her.

"That would be great, Mom, as long as no one recognized you as my mother. That would be humiliating."

"I don't think anyone would, Honey. I've never attended any school activities or events with you before this. Let's give it some thought."

Once we were home, Mom dragged me into the livingroom. We were sitting on the couch, side by each, when Mom opened the conversation.

"Do you think what's his name will say anything at school about meeting me?"

"Well, he'll mention it to Prinn, of course, and I'm sure she will tell the other girls in the club," I replied.

"And, I bet some of those girls will ask you about me," she said.

"Maybe," I countered.

"Well," started Mom, "I think we need to prepare you for their questions. First off, you need to get used to calling me by name and not Mom."

"Okay, Tessa," I said with a smile.

"We also need to give you some weapons."

"Weapons?"

"Yes, in case of questions, you need weapons to fight off their attacks. What does every couple have in their phones?"

"Umm, ah, selfies?"

"Exactly. Give me your phone."

Mom began to take pictures of the two of us sitting together with our arms around each other. I pretty much sat still while Mom changed the poses. After maybe a dozen pics or so, Mom swiped back through them. We were both positive about the quality of the photos.

"I think we need some more. These look so formal. Not like a guy and his girl that have been dating for almost a year."

I didn't have a clue where she was going with this but I was not about to argue.

Mom moved me about until she had me where she wanted me. Then she sat crossways on my lap. She snapped a pic. Reaching behind her, Mom took my hand and placed it on her waist. Snap. For her next pic, she tugged my arm a little, moving my hand to her bum.

"Fuck!" I thought to myself. "I have a hard on."

Leaving my hand there, Mom leaned into me and gave me the most passionate kiss I had ever experienced. She took pic after pic of us kissing. When her mouth opened and her tongue moved into my mouth, she took more photos. She made sure, by moving her head, that anyone seeing them would know we were French kissing.

I do not have a clue how Mom could not know that my cock had become rock hard while we were making out. How could she have missed the pole poking her in the ass?

Still perched on my lap, Mom checked out each photo, making approving sounds.

Almost to herself, she said, "These are good but they are all obviously from the same day. Rick, stay here, I need to make a wardrobe adjustment."

Mom came back a few minutes later wearing a light yellow, summery dress. The dress was square cut across her boobs putting much on display. It had a flowing skirt which hung to above her knees. Mom had put on white stockings and matching high heels. Her makeup was perfectly done as if for a formal outing.

"Ricky, sit in the arm chair, please. And take your shirt off. In this pose, it will be as if I dropped by after church. You are at home dressed very casually."

Mom was really getting into this photo shoot. I sat in the overstuffed arm chair, shirtless as per my instructions, with Mom perched on my lap and her legs over the arm. She pulled me down to her and we started making out again. Mom took my hand and put it on her legs. When I did not move, she took my hand, beginning to slide it up her leg.

Yup, I was hard again. Mom's tongue was in my mouth and my hand was caressing her thigh with the hem of the dress pushed up out of the way. Mom had to know I was hard, there was no avoiding it.

Mom's face was flushed as she broke off the kissing. Once again, she gave her approval to the photos.

"One more set," said Mom. "I want this set to be slightly risqué. I'm going to get changed again. You get out of your jeans."

With this, Mom climbed to her feet, heading back to her bedroom. My eyes were on her all the way until she turned the corner. It was a little challenging to get out of my jeans as they were fairly tight and my rock hard staff was not helping.

I was truly gob smacked when Mom came back. My tongue fell out of my mouth and I am sure I drooled a little. This view of my mother would be locked in my brain for ever and a day. It would become my next masturbatory fantasy about her.

Mom had taken the time to change her hair style, putting it into a long ponytail hanging over her shoulder almost to her boobs. She had also changed her makeup. Now she had the typical dark eyeliner, multiple shades of colour on her eyelids, and crimson, glistening lipstick. She definitely looked college aged now.

Mom ordered me back to the couch having me sit leaning on the arm with one leg on the floor and the other stretched out the length of the couch. She changed the lighting making the room a little darker than earlier.

I could not take my eyes off her as she moved around doing the setup. She was wearing a burnt orange matching bra and high cut panty set as well as dark thigh high stockings. No one could see my mother looking like this and not want her in their bed. I knew I couldn't.

Now, I knew that Mom could not miss my stiff pole this time. She had me taking pics of her starting at the far end of the couch and panther walking on her knees towards me. With both hands on the camera to combat my shaking, there was no way to disguise my condition.

When she had come close enough that those man made tits of hers were almost on my cock, she looked up smiling at me. When I hesitated, she instructed me to keep shooting photos. She told me what she wanted to see.

Mom lay with her face against my pole. If anything it became harder. She nudged it with her chin. She lifted her hind end and placed her hands on my thighs close enough to touch me. My mother had me convinced she was about to give me a blowjob.

But, alas, a blowjob from my mother was going to remain a fantasy. Mom rolled off the couch, climbed to her feet, and sashayed away.

"I think we got everything we were looking for, Ricky. You need to go to your room and take care of things."

She meant my hard on and I did.

The night of the event came soon enough. Mom and I went costume shopping a few nights before. She found hers first. My mother chose a southern plantation style peach, ball gown that showed off her big, beautiful boobs. It came with a matching half mask that covered her face from forehead to mouth.

I found a Phantom of the Opera black tuxedo in my size that also came with the appropriate mask.

On the night of the event, we drove to the meeting hall. Standing outside and off to the side, the first couple we met was Prinnzess and her boyfriend, the football hunk, Jason. They waved us over to join them.

The pair were wearing Flintstone costumes. Prinn's skirt was short with a slit in the side. The costume held her C cup tits up and outwards in a fine display. I don't think Wilma ever wore stilettoes but that did not deter Prinn who was wearing them with, I guessed, thigh high stockings.

After introductions were made, Jason held out a flask that he had been kept hidden behind him. Mom and I tried to demur but the already drunk Jason was insisting. Prinn, who had already tasted the Jack Daniels in the flask, and was somewhat tipsy, also insisted.

We all stood in the side courtyard passing the flask back and forth while exchanging pleasantries and complimenting each other's costume choices. Jason disappeared for a few minutes, presumably refilling the flask. I had never consumed much alcohol prior to this occasion and was feeling the effects. Mom seemed to have fallen under the influence as well.

Still waiting for Jason to return, Prinn leaned over to adjust her stockings proving my guess had been correct. She swayed for a moment before losing her balance completely and falling. Fortunately, I was close enough to catch her before she hit the ground and helped her back to her feet. Unfortunately, my hands ended up on her tits and leg under her short skirt.

This was the position Jason found us in upon his return.

"What's going on here?" he asked, glaring at me.

Prinn responded quickly, my arms still supporting us, "Relax, J, Rick caught me when I stumbled."

The high school senior turned in my arms, put her arms around my neck, and gave me a huge kiss to express her thanks for me saving her from injury.

The well lubricated football lunkhead objected. "Hey, you don't kiss other guys in front of me!"

Instead of responding, Prinn turned back to me, kissing me again. Mom watched the interplay wordlessly.

"If you can kiss someone else, so can I," said the lunkhead as he grabbed Mom's arm, dragging her into a tight embrace. With his hands on Mom's ass and tit, she put up a fight. She was struggling to get the creep off of her.

Naturally, I came to Mom's rescue. I grabbed the asshole by the shoulder and spun him around to face me. The momentum of Mom's struggle flung her sideways into Prinnzess. Both women fell to the ground.

Even angrier now, I slammed my fist into Jason's face. He took a step back in order to throw a punch of his own. I moved quicker and clopped him a good one right on his chin. He fell back and down hitting his head on the grass lined pathway.

With him taken care of for the moment, I turned back to the women who were struggling back to their feet. Both women were quite disheveled, both costumes were torn, both had scrapes and cuts on knees and elbows.

By this time, we had gathered a crowd around us. The guys were all standing to the side while two of the locale's security contingent escorted the drunken lout off the grounds. Most of the women were showing concern for Prinn and Mom. Except for three or four who were oohing and ahhing over my dispatching of Jason and standing well within my personal space.

As everyone began settling down, Prinn must have noticed her classmates with their hands roaming my arms and chest. Tugging Mom by the hand, Prinn led her in my direction.

Dating football players must have paid off for her as she bulldozed her way through the crowd, Mom trailing her.

Finding one of the costumed Socks pressed up tight against me, Prinn resorted to hockey, another sport played at our school, and hip checked the girl out of the way. Prinn took her place beside me, wrapping her free arm around me and pulling my date to my other side.

Mom, my date, followed Prinn's insistent lead and put her arm around me as well. Both girls were plastered against me allowing me to feel their boobs squashed against my arms.

"You're my hero," said Prinn giving me a kiss on the cheek.

She gave Mom a strong look and waited. Mom muttered the same thing before giving me a kiss on the other cheek.

"You're both of our heroes," said Prinn giving me a hard kiss on the lips. Mom followed suit.

The crowd was watching us closely but with no further moves being made by any of us, they drifted away, entering the venue. Soon enough it was only the three of us standing in the courtyard.

"We're all a bit of a mess," said Mom.

"I want to get out of this filthy costume," she continued.

"Me too," said Prinn," but I don't want to go home looking like this. My parents are having a costume party of their own and I don't want to be interrogated about looking like this."

"Why don't you come to our house then," asked Mom. "I'm sure I can find clothes for you to change into that will fit."

"Great!" exclaimed Prin.

I drove all three of us to our house. Once inside, Mom and Prinn scampered into Mom's room leaving me alone. Nothing to do except for me to get out of this bloody costume as well.

I was sitting on the couch in the livingroom, freshly showered, where Mom and Prinn joined me. They were both wearing one of Mom's silky and short nightgowns. What shocked me though was they were also wearing thigh high stockings, stilettoes, and their half masks. The material of their nighties hung low enough to cover their panties.

"Prinn is going to stay the night," said Mom. "She also knows we are mother and son."

Knowing my secret was out and that any hopes of a social life at school lay in Prinn's hands. One word from her about us pretending Mom was my date would ruin everything I could ever hope for.

"Why would you tell..." my voice dropping off as I realized the answer. As soon as Mom mentioned Prinn coming to "our" house, the cat was pretty much out of the bag.