After being given some time to think about the events of the previous weekend, I decided that I had overreacted. It was a pretty fun interaction after all, at least at the end. Best of all, however, was Mother’s reaction. I was glad that I got to see her facial expressions up close as she experienced her over-the-top orgasm.

I did my best to keep Derek at bay, promising him a return engagement. I really didn’t want to invite him back again, but there was little option at that point. If we cut him off completely, I was certain that he would tell our dirty, little secret. What I didn’t tell him, however, was that I was going to try my hand at anal sex before he got a second go at it.

On the following weekend, just before we went to shower and change for “Round Two,” I mentioned to Mom that I wanted to try anal sex. She looked at me curiously but refused to directly respond.

When I returned, we spent a fair amount of time talking about her orgasm the previous Saturday night and what might have set her off. Afterward, I placed two fingers in my mouth to wet them and I slid them inside of her pussy. I assumed a dominant position and pinned her down on the couch, continuing to finger her with increasing aggressiveness.

She was clearly getting worked up, when I whispered into her ear, “Beg me to fuck your ass, Mother.”

When she complied, I positioned her in a kneeling stance so that he was bent over the couch with her ass pointed toward me. I grabbed a condom as well as the lubricant that she had brought and prepared myself. Leaning in, I pressed the head of my cock against her waiting hole and gave it a nudge. It prodded forward but didn’t get any penetration at all. My second attempt was a bit harder but also went nowhere.

I grabbed the bottle of lube and dribbled a few drops onto her asshole. I smeared it around with the head of my cock, before I attempted another thrust.

This time I actually gained entry. I could hear Mother groan audibly and she started to take strange breaths as if she were giving childbirth. I waited for a bit before starting to move, but she pleaded for me to stop moving and eventually withdraw my cock.

After giving her a break, I tried again. It was only slightly better this time and I started to feel bad for asking her to do it. It finally dawned on me why she had given Derek the offer to fuck her ass instead of me. I had never considered that his diminutive size made him a better option for a novice at anal sex.

At that point, I kind of wanted to forget it altogether and just do something else. It wasn’t going very well and all of the stopping and starting was making me lose interest. Afraid of upsetting Mother, I continued on. Eventually, we finally got going and I hurried an orgasm along as much as I could.

Realizing that I had left Mother unfulfilled, I removed my soiled condom and put on a new one. Feeling as if I could continue right away, I turned Mother over onto her back and slid my cock inside her pussy. I started to rub her clit as I slowly thrust away. It soon became apparent that my cock was not ready to go for a second time. As it started to soften, my cock was mostly collapsing into itself or bending, and I was having trouble getting any amount of movement. I continued on for a while as my internal panic mounted. It eventually became obvious that my cock wasn’t going to function properly until it had some time to reset.

In an attempt to avoid complete humiliation, I dropped to my knees and started to perform oral on Mother. Fortunately, I was still able to perform adequately at that task. I continued until I made her cum, but that didn’t make me feel any better about the situation. I gathered my things, headed to my room without saying a word, and closed the door. It was my worst performance by far, and I was so ashamed that I didn’t even want to look at her.

I spent the following week beating myself up about my performance. My jealousy toward Derek had caused me to want to try anal sex when I had never really thought much of it before. I had clearly taken for granted how well Mother and I worked together sexually. It was obvious that we weren’t nearly as compatible with anal sex.

Although I didn’t have anything too experimental in mind for the following Saturday, I was eager to redeem myself from my sub-par performance the previous week.

When Mother arrived home with the pizza and movies, I couldn’t wait to settle in for the night. Unfortunately, just as I lifted the lid on the pizza box, Mother chirped, “Not yet, Sweetheart. You need to wait for Derek.”

I couldn’t believe my ears. “Derek?” I asked.

“He should be here any minute now,” she added.

Almost as if on cue, a car pulled into the driveway. I thought that I had come to terms with Derek’s involvement in our relationship, but this felt like a complete betrayal to me. Neither of them had mentioned that Derek would be joining us, and I had to wonder how and where the two of them had made arrangements for him to attend. Coming off of my lackluster performance and remembering how satisfying our first threesome had been for Mother, it felt like she was actively trying to improve the situation to her benefit.

I was pissed with a capital “P”, and from the moment that Derek walked through the door my anger only escalated. Every word that they spoke to one another, their playful mannerisms, and most of all, every single fucking time that she referred to Derek as “Handsome,” felt like a knife stabbing me in the heart.

Disgusted by the two of them, I only ate a couple of bites of pizza. I claimed that my stomach didn’t feel very good, which was sort of true. Mostly, I just sat on the couch fuming for the entire length of the movie.

Once it was over, I headed to my room without saying anything. Derek joined me a bit later and tried to make small talk, but I only responded with yes and no answers for the most part. I headed to the bathroom to take a quick shower. At that point, I didn’t even know if I wanted to go back to the couch, but I wanted to escape from Derek. Unfortunately, he barged in within a couple of minutes and I had to finish up and head back to my room to get a reprieve from him.

Derek seemed to be following my lead as he only wore his underwear on the second trip to the couch. Mother was wearing her robe, as usual. Once the movie started, it was once again the two of them focusing on one another. Derek had opened up Mother’s robe and was squeezing her breasts and teasing her nipples with his tongue. Mother pulled down the front of his shorts and was stroking his cock until she got bored with that and started to give him head.

Tired of being cut out of the action and eager to prove my skills, I dropped to my knees and climbed between Mother’s legs. I grabbed her backside, wrestled her to the front of the couch, and buried my head in her crotch. My tongue flicked at her clit from every angle possible. She requested that I not finish her off so early into the action, but I continued on. I didn’t stop until she was gasping and quivering in my grasp.

I pulled Mother to her feet and spun her around so that he was bent over the armrest of the couch. I yanked my underwear down to my knees and slid my bare cock inside of her. She made a sound that I had never heard her make before. I wasn’t sure if it was because I was being aggressive or if it was because she was sensitive from her orgasm. As I started to thrust, she made that same little squeak with every repetition.

“Sweetheart, did you put a condom on?” she asked, even though she already knew the answer.

“Nope!” I belted back.

I continued on harder and faster, spreading her legs wide. My balls struck the cushioned armrest with a thud each time that I pressed forward.

Derek looked at me, not quite sure what to do. He couldn’t decide whether to join in on the action or to get me to stop. Instead, he stood there like a dope with half of his cock protruding from the waistband of his shorts.

I finished with a flurry before my orgasm. My cock jerked as stream after stream of cum flooded Mother’s vagina. It was already dripping out before I had even withdrawn. Once I pulled out, cum started to pour out and pooled on top of the armrest.

“Alright Handsome, I am done. She is all yours,” I snapped at Derek.

I pulled up my underwear and walked back to the shower. After my shower, I shut myself up in my bedroom. I didn’t have any idea what happened in the living room after I left and although I wanted to know, I didn’t bother to check back.

It was roughly a half hour later when my bedroom door slowly squeaked open. Derek slowly stepped inside, staring me down the entire time. He grabbed his overnight bag and left, never turning his back to me.

A few minutes later, there was an aggressive knock at the bedroom door. As I went toward it, the door swung open and banged against the wall. It was Mother, clad in her pink robe, and she was almost as upset as I was. She started to fire off in typical motherly fashion. It was the usual, “What’s wrong with you?” “What were you thinking, young man?” sort of stuff.

I just stood there for a moment until I shrieked, “Why do you like him more than you like me?”

My voice cracked as I spoke the words and a shocked look appeared on Mother’s face.

“What? Like whom? Do you mean Derek?” she questioned.

“Yes, fucking Derek!” I retaliated. “Why did you invite him without telling me? Is it because I am not very good at it? I am trying…I am really…”

I had to stop because I didn’t want to cry in front of Mother. I was trying to prove to her that I was a man. Still, a tear started to roll down my cheek and I quickly wiped it away. She grabbed me and gave me a hug, but I refused to hug her back.

“Sweetheart, I love you, and I'm sorry if I made you feel that way. You are learning so quickly, and I thought that you would enjoy having your friend around.”

“Mom, I wasn’t ready for that, and now we can’t stop, or Derek will tell everybody. Why didn’t you just talk to me about it first?”

“I’m sorry, Sweetheart. I should have talked to you. I just thought it would be fun for both of us.”

“From now on, I will deal with Derek,” I insisted.

She agreed and I finally returned the hug. As I started to pull away, I finally looked her in the eyes. I felt myself slowly drifting in her direction. A voice was screaming, “What are you doing?” inside of my head, but I ignored it. I expected her to stop me, but she didn’t. Finally, our lips touched.

Our initial kiss was soft and tender, but things slowly became more aggressive. I grabbed Mother and pinned her against the wall. We were both working ourselves into a frenzy as we clumsily fumbled with one another.

I loosened the tie on her robe. My mouth playfully bit her breast as I started to rub her clit. Mother’s hand found its way inside my underpants and she started to stroke my cock in response.

Facing one another in a staggered position, we started to alternate kissing and taunting one another, all of the while trying to get each other off. Determined that this was not the way that we should end the evening, I yanked my underwear down to my ankles and approached Mother with my cock in hand.

Squatting down a bit, I guided my cock inside of her. I could tell by the noise that she made that she wanted it as much as I did. I grabbed her thighs and hoisted her into the air as I rose to a standing position. Her shoulders were still resting against the wall, providing some support. One of Mother’s hands was hooked around my neck as the other reached between her legs.

“Give it to me hard, Baby,” Mother snarled through clenched teeth.

I started to pump furiously. The sound of our bodies clapping together echoed through the house and was only superseded by our cries of pleasure. Our upper bodies were held in a V-pattern as we seemed to reach a level that we had never before experienced.

My head rocked backward, and I let out a primal growl as I climaxed. My vision went sparkly, and I nearly collapsed as it felt like I was pouring my very soul into Mother.

As I staggered, I realized that she was very close to orgasm as well. I tried to continue on as best as I could, but post-orgasmic sensitivity was slowing me down considerably.

I pleaded to her, “Let go, Mom. Give me everything. I want every bit of you.”

Her body shuddered as her climax began. Between wrestling with her legs and trying to keep her aloft, I nearly dropped her. She sounded as if she was crying as she shouted out strange utterances. When her cries subsided, I lowered her to her feet. We held one another as we caught our respective breaths.

We stared almost blankly at each other as we both realized that we had taken our relationship to another level. We had kissed, Mother had broken her code, I ejaculated inside of her, not once, but twice, and most importantly, I suspected that we were falling in love.

Mother seemed stunned as she closed her robe and started to walk back to her room.

“Goodnight. I love you… Son.”

I hesitated a moment as I let her words sink in.

“I love you too… Mom.”

I didn’t sleep at all that night, not even for a minute. I don’t think Mother did either, because I could hear her pacing around inside of her bedroom.

From that point forward, things were great between us. In fact, they were better than they ever had been. Although we maintained our mother/son relationship through the week, she would occasionally break character to briefly tell me something or leave me a written note.

The next couple of Saturday nights were fantastic! The sex was so much more passionate and intense than it had been before. Mother insisted that we go back to using protection, but that seemed like a small price to pay.

One afternoon, when I arrived home from school, Mom was waiting for me. She was sitting at the table, and it was obvious that something had upset her. Reaching across the table, she placed her hands on top of mine.

“Sweetheart, I have something important to tell you. I…I’m pregnant.”