Winners and Losers

"Yeah, I figured it out," said Prinn.

"And, you know what?" asked Prinn.

I shook my head, no.

"I've never fucked a guy in front of his mother before," she said.

With that, Prinn came to the couch and sat on my lap sideways with her legs pointing to the opposite end. Mom sat on the far end, lifting Prinn's feet and placing them in her lap.

Prinn's mouth closed on mine. Her first kiss was as passionate as I dreamed about. I felt awkward since we were moving into areas I had not traversed before in my life. I think I responded well though as Prinn only pushed harder against me, her tongue bullying its way into my mouth.

I was still nervous about doing this, especially in front of my mother. A sly glance in Mom's direction told me that although she was watching Prinn and me, she was also caressing the cheerleader's feet and legs up to her knees.

It was no problem with me that Prinn was taking the initiative in this encounter. Since I was a virgin in every sense of the word, Prinn's low level dominance worked for me. It removed all questions concerning what I should do next.

Prinn and I were still making out, her tongue twirling around mine in my mouth, sometimes chewing on my lips, sometimes licking me. She also decided she wanted more participation from me since she took one arm from around my neck and used it to lift one of my hands to her tits.

They felt great. Prinn's tits were everything I could have imagined. They were large enough to fill my hands. They were firm, even hard. Her nipple was poking into the palm of my hand. I kept squeezing them.

Another quick glance towards Mom showed that she had changed positions. No longer was she on the couch. Instead, my mother was on her knees, letting her hands roam from Prinn's knees to high on her thighs to the flesh under her nightie.

I decided to take some initiative myself. From one tit to the other, I moved my squeezing hands, enjoying the feeling completely. Since Prinn offered no objection, I slid my other hand between us in order to grasp her ass. The cheerleader's body was taut and firm everywhere. Her cheeks made a statement reminding everyone checking her out that she was an athlete.

With one hand working on Prinn's tits and the other clasping and grasping her ass, Prinn turned up the passion of our French kisses. There was drool dripping out of my mouth but she did not seem to mind.

Prinn changed positions as well, putting one foot on the floor and taking charge of my dick. Obviously, I was rock hard at this point. In fact, I was concerned that I would cum too soon. Already, I was feeling the tingling in my balls that signaled semen would be wanting its release before long.

Since, I was still wearing my boxers, Prinn was working my staff and testicles from the outside. It felt good but I really wanted her hand on my flesh. Prinn began to moan taking me by surprise.

I thought the cause was from my manipulation of her tits and ass but, breaking apart for breaths of air, I saw that Mom was the cause. With Prinn having spread her legs and dropping one leg to the floor, Mom had more flesh to work with.

I had never imagined my mother with another woman. Mom either had experience however or a wonderful imagination. She had her left hand on Prinn's planted leg, still caressing her from knee to thigh. It was the other hand that was doing something new.

That hand was under Prinn's nightie, running from her knee all the way, I guessed, to her pussy. My guess was based on the fact that Prinn was regularly bucking her hips upwards depending on where Mom's hand was.

"I want this cock," said Prinn as she attempted to pull my boxers lower. Unfortunately, she was having difficulties getting my fully engaged staff past the waistband.

"Tessa, please help me," whined Prinn.

Mom removed her hand from under the cheerleader's nightie. She licked her wet fingers as she moved toward us to help. Now I had both women struggling with my dick and neither was having much success.

"Prinn, slide over so I can get it out," instructed Mom.

Following instructions, Prinn slid off my lap. She ended up leaning against the back of the couch with her legs spread widely. Mom wasted no time pulling my boxers down and off.

Of course, Mom had to handle my cock while freeing it. This was something I had long fantasized about. Mom jerking me off until I shot my load all over her big boobs was one of my favorite fantasies.

That was not to be right now though. Realizing that fantasy had to wait. Mom's focus was entirely on Prinn. I watched my mother, fighting to keep my hands off my dick, licking Prinn's thighs and pubes, completely avoiding her pussy.

Prinn was moaning, probably due to Mom's teasing tongue rather than my groping of her tits. But seeing Mom's mouth at work gave me the impetus to lean over and use my mouth on the boobs I had paid so much attention to whenever the opportunity arose.

Prinn must have liked what we were doing as my mouth on her tits increased the volume of her moaning. She placed one hand on the back of my head pulling me even tighter against her tits. She had the other hand lightly on the back of Mom's head. Me, she was directing; Mom she was allowing to do as she wished.

I don't think Mom had her tongue in Prinn's pussy yet so I reached down and checked it out. Mom was licking and nibbling the cheerleader's thighs but not actually her pussy. Just damn close.

Deciding to use one of the lessons I had learned by watching porn, I went searching for Prinn's clit. And, while I was fumbling around down there, Mom came to my aid. She took my index finger, drawing it from the extreme bottom of Prinn's pussy to the top. She did this repeatedly.

We knew Prinn was enjoying the feelings we were causing. Her moans had grown to a high pitch and my hand was becoming wetter and wetter. I wanted to lick Prinn's fluids off my fingers but Mom was not letting go of my hand.

On my next swipe of pussy, Mom pushed my finger deeper between Prinn's thighs. Her next move was to direct me into finger fucking Prinn's hot and wet pussy. She was tighter than I expected. I was surprised when I felt one of Mom's fingers sliding into Prinn alongside mine.

Prinn must have realized she had each of us playing in her cunt as she exploded. Her moans turned into shrieks. The girl was so loud you would have thought we were killing her.

All the while my cock was aching. I was holding my own eruption back by sheer willpower. That was not too last though as Prinn reached out, grabbed it, and before she could do anything else, I was ejecting rope after rope of cum into the air splattering myself from neck to knees. Man, that was intense!

I was pleased to see that one orgasm was not taking Prinn was not out of the game. She tugged at Mom so she would change places. With Mom beside me on the couch, Prinn, on her knees before us, began licking my spend off my body. But, she was not ignoring Mom, Prinn was busy caressing Mom's big boobs.

I wasn't paying much attention to what Prinn was doing to me. Granted, her fingers and tongue on my body felt wonderful but I could not take my eyes off my mom's body and what Prinn was doing to it. I was shocked to see Prinn offering my mother some of my cum from her fingers. Mom accepted the offer.

Time passed, how much I really don't know as I was far too focused on the women to pay attention or to care even. At some point, Prinn had started ignoring me and was devoting herself to Mom.

As soon as Prinn's mouth was locked onto one of Mom's tits, I was hard again. I went from zero to almost boiling over in no time flat. I had a solid hold on the base of my pole, fighting to keep myself from exploding again.

Mom was laying back against the couch cushion, with her legs spread and Prinn between them. Prinn must have taken one of Mom's nipples between her teeth and bit down as Mom jumped, ending up with her hand on my thigh. Oh my gawd, my mother was touching me during a sexual encounter. This had the makings of a great porn video.

With one hand on my thigh and the other on Prinn's shoulder, Mom replaced Prinn's moaning with her own. Mesmerized, I was staring at Prinn working on Mom's tits. Or nipples rather. She was moving from one of Mom's boobs to the other, gripping her nipples with her teeth, and pulling the tits they were attached to in different directions.

But, Prinn was not satisfied with simply mauling Mom's tits. She had both her hands between Mom's glistening wet thighs. Mom began to dig her nails into my thigh as she emitted yips and yikes signifying her pleasure.

Prinn moved on past Mom's saliva soaked tits down to Mom's pussy. Feeling Prinn's mouth around her cunt, Mom gasped and dug her claws even further into my leg. The pain, I think, was keeping me from cumming. But it was not enough to distract me from the two women beside me.

She must have felt that Mum was close to her own orgasm as Prinn was not wasting any time. I could hear the sounds of her sucking the fluids from Mom's cunt. While still dug into my leg with the one hand, Mom had the other on the back of Prinn's head holding tight. Mom was bucking against Prinn's face as her own noises were changing to shrieks.

Mom must have flooded Prinn's mouth with her fluids as she screamed her way into orgasm. I thought she was going to rip a chunk of meat from my leg with her lioness-like claws. It hurt so much that I yelled out as well.

I inadvertently threw my arms into the air. Fortunately I didn't hit Mom but I did succeed in slapping the lamp on the end table to the floor. Darkness enveloped the room. Only a nightlight in the hallway kept it from being pitch black.

Turning back to the women, Mom and Prinn were making out. Mom's hand had relaxed its blood drawing grip on my leg. Prinn's hand was on top of it. Soon, I felt their hands moving. Prinn's hand was still on top and drawing Mom's hand along with her own towards my cock. I could not quite believe it but not only was I going to have two women doing whatever they wanted with my dick, one of the two was my mother. I do not have any idea why I was not ejaculating just at the thought of it. My mom!

"It's your turn now," whispered one of the women. I don't know which voice spoke or whom they were referring to. It turned out to be me. With one hand holding my rod straight, the other body, obviously Prinn's, swung up and onto my cock.

I did not want this night to end. Prinn, the hottest of the school cheerleaders, was riding up and down on my staff while Mom's hand was caught between our two bodies. Prinn squirmed a bit and Mom's hand moved with her.

My balls were now in Mom's trapped hand. She turned her arm until they were riding in the palm of her hand. Prinn's long admired boobs were in my face giving me little option but to glue my mouth to them.

My cock was hurting now. I was fucking the cheerleader I had lusted after for so long. The one I had been admiring even more closely and personally for the past few hours. My mother had her hand on my balls and I just finished watching a lesbian performance she starred in.

That was it. There was no holding back. I spurt ropes of my cum deep inside Prinnzess. I wouldn't have thought it long enough but as I started to cum, so did Prinn. I was bellowing my way through my orgasm while Prinn shrieked through hers.

In only moments, I was fully spent. My cock having played its role in our sexual encounter softened quickly, slithering out of Prinn's clenching pussy. Prinn moved to the softly carpeted floor, laying out flat on her back.

Mom let go of my testicles before moving towards the girl on the floor. She cuddled up with Prinn, her head on the girl's chest. I lay awake for a while reviewing all the activities of the day.

Sometime later, I'm not sure how long since I had fallen asleep, I was woken by my cock being sucked again. It startled me since this sexually open lifestyle was still so new to me. I reached down with one hand, felt the crown shape of the half mask Prinn was wearing before settling back to enjoy the feelings I was coming to love.

Prinn was a wonderful cocksucker, obviously well versed in making men cum. Her lips and tongue were so wet as they slid up and down the sides of my staff. Her tongue kisses to the tip of my pole seemed loving as much as erotic. I don't know why I felt this way, I just did.

With one smallish hand holding my dick up and the other cupping my balls and squeezing them gently, I gave into the completeness of the experience. Prinn rotated between licking my little head like an ice cream cone and sucking on it like a lollypop. I don't know which I preferred, both were overwhelmingly good.

Due to my positioning, the only part of Prinn I could reach was her long hair. So, the only thing I could do was stay laying back and enjoying. Oh, did I enjoy!

With the impressive job she was doing on my dick, I expected I would need to cum again soon. Prinn must have felt the same way as she altered her grip in order to grip the base very tightly. She was not allowing me to cum too quickly but neither of us was taking into account how many times I had already cum that day.

The sounds she was making as she slurped at my rod were intoxicating in their own right. Using her teeth to scrape my staff brought me to new heights. Prinn was doing such a great job of sucking cock that I was breaking out in goosebumps.

Time passed and I knew my balls had refilled themselves creating more semen to flood this girl's tonsils. I wish I had the words to better describe how well this girl was doing giving me this blowjob. The only thing I could say was a whispered, "I'm going to cum soon."

Prinn heard my whispered warning and, in response, began deep throating my cock. Her timing was great as her mouth was enveloping my head when she was blasted with my cum. Once again, many ropes were expelled but not with the volume or force of earlier.

I thought we were done but Prinn did not share my opinion. Very quickly, she rose to her feet, lay flat on the couch, and pulled me, by the ears no less, until I was on my elbows between her thighs inhaling her musky aroma.

With Prinn's hands locking my face against her quim, I had no room for movement. I did the natural thing. I reached my tongue out to begin licking the wetness on her thighs. By a fluke of the lighting, her cunt was reflecting her fluids.

I loved the musky, earthy taste of our cheerleader. Placing my mouth over her labia, I sucked as much of her juices in as I could. That well did not seem to be running dry though.

I locked my lips on her labia. They were long and spongy. As I began sucking at them, one by one, Prinn signaled her approval by beginning to once again moan. Even her noises were erotic in their own rights to my ears.

Moving upwards, I tongued her clit gently. Prinn pulled my head even tighter against herself leading me to the conclusion, she wanted me to tongue her little button even harder. So I did and her volume increased as well.

With lips and tongue, I continued to work her pussy and her clit with increasing volume in synchronized time with every move of my tongue. In moments more, Prinn was yipping and yiking in response to her impending orgasm. In a few more moments, she was flooding my face with more cream as her muscles seem to lock in place. I kept licking until she released her tight hold on my head.

As her breathing came under control, Prinn whispered to me to sit up. Not willing to chance any stoppage of this encounter, I did what I was told.

Laying back against the couch cushion, both feet flat on the floor, I felt my cheerleader shift her position. As she stood in front of me she tapped my knees signaling me to spread my legs wider. I was expecting another blowjob, and almost disappointed. I wanted to fuck her, I wanted to sink my cock into her tight cunt.

Prinn must have been reading my mind. She straddled me, took my pole in her hands, and slid down, immersing me in the warm wetness of her pussy. When she was sitting with my balls against her ass, I reached up to wrap my hands around her tits.

But, they were not Prinn's boobs at all. They were my mother's much larger breasts.

"Mo..." I began to exclaim but was stopped by her shushing me as she brought her lips to mine. The first kiss we exchanged was long and loving. So endearing.

"I didn't know it was you," I whispered between kisses.

"I know," responded my mother.

In no time we were making out. Our tongues met, hers swirling around mine, mine jabbing at hers. I had frozen still with the intenseness of the passion I was feeling for my mother.

"Fuck me," she whispered. "Fuck your mother."

I may have mentioned that I am very good at following women's orders when sex is involved and this time was no different. With my feet firmly planted on the floor, I began to lunge upwards into my mother's pussy, fulfilling a life of fantasies about Mom.

Mom rode up and down on my staff, our motions becoming synchronized. With our kissing suspended for the time being, I went to work on Mom's tits. They were so much larger than Prinn's, the only other tits I had ever felt. They were firm but still soft. Mom's nipples were huge, strong, rock hard, and I loved them.

Remembering something from earlier, I bit down on a nipple and pulled her tit from side to side before switching nipples and performing the same actions. I really wanted a good long look at them but the dim lighting was working against me.

Poor lighting did not mean I could not feel them though. Or taste them. Mom's tits had a unique taste, a mixture of cum, sweat, and saliva. As good as the finest champagne. Not that I knew what champagne really tasted like.

As we fucked, licked and felt each other's body, Mom had two small orgasms. Her riding of my cock soon came to be almost spastic. I guessed my mother was about to have a major orgasm.

The thought of cumming in my mother's cunt with her tits in my mouth, was enough to bring me to full attention. I could feel the semen rising from my balls, my testicles clenching and releasing in an automatic response to the tight pussy smashing down on my dick. I could feel my cock widening, growing as the semen worked its way upwards to its goal.

Mom's muscles locked down on my cock as she began her ride to a major climax. The tightening and squeezing made me lose control. We were both screaming our way into orgasmic heaven. Mom gushed, her fluids pouring out past my cock. I had one long, hard explosion of cum into her pussy.

Eventually, our breathing calmed, and we returned to kissing. No tongues this time, just long, deeply passionate kisses that two lovers may enjoy as post orgasmic lassitude settles on them.

In a moment, we felt Prinn beside us on the couch, folding her body into ours.

"This is the best Halloween ever," she declared. Neither my mother nor I was willing to argue the point.

"And I'm the winner," I said.

"I think we're all winners tonight," said Mom.

Thanks for reading my story. I hope you enjoyed it. Please comment and/or vote. Especially if I am in time for the Halloween contest.