My Mom's Disgusting Boyfriend

I slowly turned my head toward Trey in disgust. He was smiling from ear to ear. What a cocky bastard, I thought. The nerve of him, talking to me that way with my mom, his girlfriend, in the next room.

“How dare you talk to me that way!” I felt the blood rushing to my face. “You know my mother happens to be in the next room!”

“You won’t tell your mom, Jessica,” Trey interrupted. “You know why?”

I looked away from him.

But Trey continued anyway, “Because you would have done so by now! You know as well as I that it’s too late. Besides, do you really think your mom would believe you over me?”

Just then my mom walked back into the room with the drink. She sat down next to Trey on the couch and snuggled up to him.

“Ok, Sweety, let’s play the movie.”

Throughout the rest of the evening, Trey made knowing glances at me while I tried to ignore him. But he was right, I wouldn’t tell my mom or anyone for that matter. Like anyone would believe me anyway…

***

After that night, I did everything in my power to avoid Trey as much as I could. I hated that bastard. When he would stop by, I always made it a point to be in my bedroom or out at a friend’s house. I started to lock my bedroom door at all times, even when Trey wasn’t there. I figured the longer I stayed away from him, the better chance he would leave me alone. For sure, he would give up, eventually.

But I couldn’t avoid him all the time especially when he would stop by unexpectedly. And during those times, he was drawn to me like a magnet and would always go out of his way to greet me with a kiss on the cheek and sometimes a squeeze on the ass when my mom wasn’t looking.

One time, I happened to walk by him in the hallway when he was on his way to the bathroom and he “accidentally” rubbed up against me with an obvious fat, hard-on sliding across my body. I literally pushed him away, which he really seemed to enjoy.

“You’re such an ass!” I scolded him.

He just laughed at me and replied, “Can I help what you do to me?”

And there are plenty of other examples I could mention detailing his harassment. I honestly felt hunted by him, and I expended a lot of energy just trying to stay away from the guy in my own home.

Looking back during this time, it is amazing to me that my mom was so unaware. Trey was certainly a sneaky son-of-a-bitch and he definitely had mom eating out of his hand.

***

Soon after, my best friend, Riana, was over at my house to complete a school project with me. We were sitting at the kitchen table when my mom walked in with Trey.

“Hi, guys! Whatcha doin’?” my mom asked, walking in with a bag full of groceries.

“Hi. We’re just finishing up that project for World History,” I responded, careful to not look up from my schoolwork in order to avoid eye contact with “you-know-who”.

“Hi, Ms. Novak,” my friend answered.

My mom suddenly turned to Trey, “Oh… Riana, have you ever met my boyfriend, Trey?”

“No,” she replied.

“Well, then. Riana this is Trey.” My mom loved to show him off. What a prize.

Trey approached Riana and extended his hand, “It’s a pleasure to meet you, Riana. Between you and Jessica here, I’m sure you have all the boys at your school begging for dates!” It was obvious that Trey was flirting with her and of course, my naive mother was blind to it all.

Riana accepted his hand but looked slightly embarrassed by the comment.

“Ah… thank-you,” she replied with a smirk on her face.

My mom interjected, “And what are you two doing tonight?”

I spoke up. “I’d like to go over to Riana’s house to swim in her pool, if that’s alright.” Riana’s family had this really cool in-ground swimming pool and consequently, her house was quite a popular place in the neighborhood to hang out.

“Sure, Sweety. Just be home by midnight.”

“Ok, mom. We’d better get going,” I motioned to Riana. “I’m just going to pack my swimsuit and then we’ll go. Riana, come help me.”

We stood up and managed to walk by Trey without any contact. Miracles never cease!

As I closed my bedroom door, Riana flopped herself on my bed and exclaimed, “Wow! Your mom’s boyfriend is HOT!”

I looked at her dumbfounded, “You really think so?”

“Hell yes! I would do him in a heartbeat! He looks like Magnum P.I.!” she said staring at the ceiling.

“Well, he may be good-looking but he is an asshole,” I announced. “My mom deserves much better than him.”

Riana laughed, “C’mon Jessica…did you see the body on him?? AAUUUHHGGHH,” she groaned into my pillow that she now held over her face.

“Whatever!” I said lifting my bag while rolling my eyes. “Let’s get out of here before you have an orgasm on my bed!”

Riana’s house was only a couple of blocks from mine so we were there in a couple of minutes. What my mom didn’t know was that Riana’s parents were away for the weekend and Riana had taken the liberty of inviting our boyfriends over. The two boys, John and Shawn, were also seniors at our school. John was Riana’s boyfriend and it was common knowledge at our school that they screw all the time.

Shawn was John’s best friend and we had been dating for about 4 months. He had just moved to our school that year and was a real cutie. He was a typical mid-1980’s hard rock guy and often wore concert t-shirts such as “Motley Crue, Dokken, Scorpions”, etc. Shawn only stood about 5’8”, with a slender, yet athletic build. He had longer, blonde hair, which was styled similar to how the tennis pro, Andre Agassi, had his hair back in the day. He was really the opposite of me in many ways since I was always the preppy, nice-girl.

Shawn had taken my virginity a month prior and since then, we had done it one other time. To be honest, sex with Shawn was pretty disappointing. I remember that he used to cum really fast which frustrated the hell out of me.

Anyway, we arrived at Riana’s house and made some dinner before the guys showed up a little later. As they entered, I could see that John had something in a brown paper bag.

A little later, over the sounds of the Aerosmith album, “Permanent Vacation” coming from Riana’s mini-stereo, John took out a bottle of Captain Morgan’s Spiced Rum and asked, “Got any coca-cola?? Let’s have a drink!”

I wasn’t much of a drinker at that point in my life, however, I was somewhat tired of my “prudish” image at school and wanted to be more like Riana (who was a known “bad” girl). While she grabbed a two-liter bottle of coke from the refrigerator, I made small talk with the guys. Shawn was definitely giving me a lot of attention and I knew he would probably try to get sex from me later. Especially since I didn’t give it up to him a couple weeks before when I was on my period.

The four of us proceeded to get pretty drunk that night, intensified by drinking games such as “asshole” and “quarters”.

Later in the evening, Riana rose from her seat and suggested that we go swimming. Even though it was dark outside, Riana’s pool had lights set up in and around the pool. She and I went up to her room to change into our bikinis and the guys used the bathroom.

By the time we came out, we could already hear Shawn and John splashing around in the pool. We walked out to the backyard each wrapped in a towel.

“C’mon, girls. The water feels great!” John exclaimed.

We ditched the towels to obnoxious whistles and catcalls from the guys. I wore my yellow bikini, which accented my large breasts, flat stomach, and toned ass quite well. Years of playing soccer had really paid off. Although Riana was more petite than I was, her red bikini was no slouch either. It was a good color considering her features, namely her tanned skin, dark eyes, and long, brown hair. Riana could be described pretty much as your classic Latina beauty.

We dove in. Riana swam right up to John in the deep end and started horsing around with him. I decided to hang out in the shallow end.

Shawn eventually swam up to me and said, “Are you bored, Jessica?”

I sat down on the bottom stair that led out of the pool with only my chest and head sticking out of the water.

“No…no,” I smiled, “I’m just kind of buzzed from the drinks is all.” This was the truth since I felt quite light-headed and spacey. The drinks had been very strong. But also I was thinking about Trey and what to do about that situation. I was honestly tired of ducking him on a near-daily basis. Maybe I should just let him fuck me to get it over with, I thought, completely oblivious to Shawn who was now standing right in front of me. It would almost be worth it just so he’d leave me alone.

All of a sudden it became real quiet and when I looked over Shawn’s shoulder, I could see that John and Riana were in a passionate embrace. They’ll probably end up doing it right in the pool, I thought.

Shawn took a quick look over his shoulder and acknowledged our friends’ behavior with a quick laugh. That was all the encouragement he needed. Shawn leaned down and kissed me hard. He then parted my lips with his tongue and expertly stroked the interior of my mouth while occasionally sucking lightly on my tongue. The attention was having an affect on my body as my pussy became wet and my nipples erect.

Shawn’s hands were now massaging my back as we continued to make out. I became concerned about Riana and looked up just in time to see her and John exit the pool and enter the house. I could see Riana’s breasts hanging in the breeze.

I could feel Shawn’s dick get erect as he rubbed up against me. He was definitely ready for it. My hand went down to his crotch and I started to rub his hard-on. I decided that wasn’t enough and my hand disappeared down his swim trunks, taking a hold of his cock. It was small, maybe 5 inches when erect and pretty skinny.

Shawn eventually maneuvered himself between my legs. He pulled off his swim trunks and his tool was now rubbing up against my crotch in a rhythmic fashion. Now, I was definitely ready.

“Ohhh, yes,” I gasped as Shawn left my lips and started sucking on my neck. He stayed there for a while, feasting on both sides until he started to wander south.

Fumbling around, Shawn pulled down my bikini top and attacked my breasts. All sorts of slurping noises came from his mouth as he devoured them, somewhat awkwardly. I must say, though, that he really seemed to enjoy them. And that, in itself, was a turn-on.

“Ohhh,” I groaned.

“Oh, God, Jessica. I LOVE your tits,” Shawn whispered at one point. “You have the hottest body in the school!”

That was almost enough to make me orgasm right then and there. Not that I believed it much, but I knew I could definitely compete with any girl at my school, even the older ones.

Shawn eventually let his hands fall to my ass, which I allowed. He would gently squeeze it before pressing my body closer to him. That’s when I had a flashback of Trey playing with my asshole that one night. How I wished Shawn would tease me the same way but I knew that was NOT going to happen.

As Shawn started to untie my bikini bottoms, I decided that I wanted to have sex with him right there in the pool.

Now that we were both completely naked, Shawn sat down on a step and pulled me toward him. I mounted myself over his hard penis and gently fell upon it. It went in quite easily and I was starting to feel great. Just as I started to buck faster, I was horrified to here Shawn gasp, “Auggghhhhhhhhhhhhhh” followed by the sensation of “squirting” inside me. And just like that, it was over.

Shawn pulled me off of him and looked very content. I was quite frustrated as I put my bikini back on and climbed out of the pool.

“That was awesome, Jessica!” Shawn commented from the middle of the shallow end, apparently oblivious to my feelings.

“Great, I’m glad you enjoyed yourself,” I said sarcastically while toweling myself off.

I considered letting it drop, but I couldn’t resist.

“Shawn?” I asked.

“Yes.”

“Do you ALWAYS cum that fast?” I asked with a cold stare.

Shawn appeared confused by the question. He waited a few seconds, perhaps to choose his words carefully or maybe because he didn’t know what to say.

“Um...well…no. Not all the time,” he answered.

I looked away and sighed loudly. He doesn’t have a clue, I thought.

I stood up abruptly, “Well, I have to get going. I’m supposed to be home by 12.” I gave Shawn a quick kiss on the cheek and walked back into the house.

Walking upstairs to look for Riana, I approached her bedroom. Her door was open and I peered inside. Riana was in her bed, butt-naked on here hands and knees, while John was fucking her from behind. The radio was playing loudly in the background, which seemed to drown out any noise they were making. Riana met each of John’s thrusts with a thrust of her own and I was amazed by the intensity of their lovemaking.

Sexually frustrated, I decided to take a quick shower before letting myself out. It appeared that Riana was going to be preoccupied for a while anyway. Must be nice, I thought.

***

As I approached my house, I could see that all the lights were off which meant that my mom had gone to sleep. Unfortunately, Trey’s car was still in the driveway. I sighed as I wondered what else could possibly go wrong this night.

I unlocked the front door and quietly entered my house. My hair was still wet from my shower, and I was still dressed in my bikini and beach towel. The living room was almost pitch black when I entered and I waited a second for my eyes to adjust to the dark before proceeding to the kitchen. The rum was still having an effect on me as I discarded the towel and placed it over a chair. I poured myself a glass of iced tea and stared out the kitchen window, alone with my thoughts.

Just then, I heard a noise behind me. I turned and saw a silhouette of a person standing in the kitchen doorway.

“Who’s there?” I whispered, praying it wasn’t Trey.

The figure walked toward me slowly and finally stepped into the moonlight penetrating the room from the kitchen window. I took a step back. It was Trey with that cocky grin on his face.

He stopped about 2 yards in front of me and I could see he was dressed in nothing but a pair of boxers. My eyes were naturally drawn to the bulge between his legs, but I caught myself and looked away. As usual, he smelled of cigarettes and Polo cologne.

I didn’t know what to say. I felt extremely vulnerable dressed only in my bikini. I crossed my arms to shield my exposed breasts as if that would offer me some kind of protection.

I blurted out, “What are you doing up?” before turning back around and staring outside.

“I got up to see how your pool party went,” Trey replied sarcastically.

I didn’t bother to turn around, “It went fine. You can go back to bed now.”

“Was your little boyfriend there?” he asked with a laugh. He was directly behind me now and his face was right next to my right ear. Trey had me trapped up against the kitchen sink and he knew it. I could feel him brush up against me. He was rock hard, as usual.

“No. Of course not. And what do you care anyway?”

Trey laughed at my terse response, but then asked, “Jessica, have you been drinking?”

“No!” I said as I quickly tried to slip by him without even turning.

And that is when he made his move. In one quick motion, he grabbed me by the hips and spun me around to face him. “I think you have, Jessica. You’ve been a very bad girl tonight! So why stop now?”

Suddenly, Trey forcefully kissed me on the lips. He was all over me and I couldn’t escape from his embrace. I tried to resist by turning my head but Trey pulled it back toward him, roughly. His moustache felt strange against my face as he shoved his tongue inside my mouth, effectively muffling my protests. I tried to kick and hit him but all my efforts were in vain for he was way too strong.

Trey subsequently picked me up as if I was a child and sat me down on the countertop. He appeared to have a specific plan in mind as he went to work on my body. Trey forced my legs apart and began rubbing his groin against mine. I gasped as I felt the sheer weigh and volume of his meat against my private area. It felt different, but in a good way. Before long, it started to feel good. I couldn’t help it; my crotch became drenched quickly, as usual.

It was at that point that I pretty much surrendered. I literally gave up. The fact was that I was tired of fighting Trey off and he had worn down my resistance. Besides, it started to feel too good. Maybe the alcohol had something to do with it, also, or maybe it my boyfriend’s fault for not knowing how to screw.

Whatever the reason, I suddenly changed strategies abruptly and started to kiss Trey back as he explored me with his gigantic hands. Surprising even myself, I threw my arms around his shoulders and clasped my legs around Trey’s waist, wanting to get as close to him as possible. Trey paused for a moment, almost confused by my apparent cooperation. However, when he realized I was willingly participating, he went right back to work. I was past the point of no return now.

I was turned on in ways that I had never been before. While I hated Trey passionately, I needed him to have sex with me that night.

Trey pulled down the top of my bikini, and groped and squeezed my ample breasts, as he continued to French-kiss me deeply. He also continued to dry hump me right there on the countertop. All this stimulation at one time was driving me crazy.

At one point, I pulled away suddenly and whispered, “Wait! Not here!” Trey gave me a nod, understanding that we needed more privacy. I led him by the hand, quietly, past my mom’s bedroom and into mine.

As I closed and locked my bedroom door, Trey came up behind me and violently ripped the top and bottom of my bikini completely off. I now stood there completely nude with my mom’s boyfriend behind me. I was absolutely shaking with lust but too afraid to turn around.

“Go over to your desk and bend over,” Trey whispered in my ear. I walked to the desk and Trey gently pushed down on my back. I was now bent over my desk on my elbows with my ass and pussy now completely exposed to him. As he knelt down behind me, my heart was pounding in anticipation. I was dripping wet and I ached to be touched.

Trey then methodically had his way with me. He began by circling my clitoris with his tongue clockwise, gradually increasing the speed and pressure.

“Ohh…Ohh…Ohh…Ohh,” I groaned making sure I wasn’t too loud.

Just when I’d thought he was going to going to attack my clit straight on, he changed pace by circling counter-clockwise, careful not to actually touch my swollen clit. On several occasions, I moved my ass back toward him with the hope it would make contact with his tongue, but with no success. It felt wonderful but frustrating at the same time. I could tell what he was trying to do. He was trying to get me as horny as possible and it was working!

When I least expected it, Trey attacked my clit and pussy with a vengeance.

“Ohhhh!” I groaned not expecting it to feel quite as good as it did. Trey then spent the next several minutes devouring my pussy. He sometimes licked my clit and my pussy, up and down, in one long stroke, often changing speeds.

Trey eventually focused solely on my pussy and seemed to content with trying to lick up as much of my wetness as possible. My legs and really, my whole body were trembling with a combination of lust, anxiety, and fatigue from standing there.

“Trey…Ohh…Ohh…Trey, your going to make me cum!!” I whispered to him over my shoulder. “Ohh…Ohh…Ohh…Ohhh…Ohhh…Treyyyyy…Ohhhhhhhh…”

Upon hearing this, Trey began to tongue-fuck me, deeply. It felt like a miniature penis and I have to say that Trey’s tongue actually felt bigger than my boyfriend’s penis! And at least Trey’s tongue could go longer than 15 seconds!

I was now bucking my hips back at his face and I was very close to my first orgasm with another person in my young life. I started to come in waves. “Ohhhhhh…. Ohhhhhhhh….Ohhhhhhh….Treyyyyyyy…. Ddddooooon’t sssstttttoooooopp!!!!”