Mom's Boyfriend

My mother introduced me to her boyfriend, Trey, for the first time when I was 18 years old. It was the beginning of my senior year in high college and I was pretty innocent in many ways. Even though I had started to date by that time and even had tried sex once or twice, I was a pretty naïve teenager. 

Mom and I had been alone since my father died when I was 9 and since then, she hadn’t dated much. Actually, I don’t remember her dating at all until Trey came along. I’m certain that she grieved for my dad for way too long, which explains my extreme happiness when my mom came home from work one day and informed me that she had met a new man. 

I remember that day vividly because I was always concerned that my mom would be alone for the rest of her life. Now, I should explain that my mom wasn’t ugly or a bitch or anything. In fact, she was (and still is) quite beautiful and nice, and many younger men asked out my mom during this time, not realizing that she was already in her mid-30’s. The fact that she frequently exercised in order to maintain her cute body helped attract a fair amount of men. And her long, wavy, golden blonde hair, large breasts, flat stomach, and flawless complexion probably worked to her advantage as well (characteristics I am proud to say I inherited, although I am a bit shorter than her at 5’4”). I remember occasionally, some people thinking my mom was my older sister, which, of course, always made my mom’s day. 

Anyway, my mom had been fixed up with Trey, a (cough) used car salesman, by one of her married friends. I remember thinking what a curious match for her- a used car salesman. Since my mom is a lawyer, I always figured someone with more education would be most ideal for her. 

Anyway, my mom and Trey had already gone out on a few dates and she wanted me to meet him that next Saturday night. Mom seemed quite excited about Trey and I was anxious to meet him. Perhaps our blind optimism contributed to the chaos that followed. I’m not sure. But I can say that our lives were never the same after Trey entered our lives. 

***

Saturday night finally arrived and it was refreshing to see my Mom all made up for her date. She kept asking me for make-up and clothing advice and for once, I felt like the parent in our relationship. By the time Trey rang the doorbell, I can honestly say that my mom looked hot.

I was sitting in the living room, watching television when I heard my mom open the front door and greet Trey.

“You look fantastic, Linda!” a loud, masculine voice came from the hallway. 

“Thank-you,” I heard my mom answer. “Come… I want you to meet my daughter.” I could tell from the way she spoke that she was embarrassed by his compliment.

My mom subsequently led Trey into the living room. A handsome man, Trey stood about 6’2”, with short, dark hair, brown eyes, olive complexion, and a muscular build. With his thick, dark mustache, he sort of resembled Tom Selleck, I thought. He looked about 40 years old and was dressed casually, yet stylish. 

“Trey, I would like you to meet my daughter, Jessica,” my mom announced proudly.

Trey smiled and looked directly into my eyes. He reached out for my hand and I accepted it. “Well, it is quite a pleasure to meet you, Jessica. I feel as if I know you already from what your mom has told me.” Trey shook my hand firmly and seemed to hold it a couple seconds too long. 

“Yeah…It’s nice to meet you, too.” I said timidly. I broke eye contact with Trey after it became a bit uncomfortable. I then looked at my mom and asked, “So where are you guys going tonight?”

My mom turned to Trey, “Dinner at Gibsons, right?”

“Yep, I made reservations for 8 o’clock sharp.”

My mom glanced down at her watch and then back at me, “Ok, then. We better get going. There’s money on the counter to order a pizza later, if you want.”

“Thanks, mom,” I answered.

“Ok, we’re going then. I love you, Sweety,” She leaned over and gave me a kiss on the cheek.

“Love you, too, Mom. Have a good time!”

I looked up at Trey who was still gazing at me. I thought I caught him checking out my boobs, but I managed to blurt out, “It was nice to meet you.”

“Likewise, Jessica. It was very nice to meet you! I’ll see you later,” Trey announced as he leaned over and gave me a kiss on the cheek. This startled me somewhat since I had just met the man, however, I just went with the flow and reciprocated. He smelled like a combination of cigarettes and Polo cologne. To this day, I am repulsed by that cologne. 

With that, they both left for their date. 

***

The rest of the evening I thought about Mom and Trey. He seemed nice enough and definitely handsome. I could definitely see why my Mom was attracted to him. However, something about him made me feel uncomfortable. Trey oozed confidence, almost too much. And was he really checking me out?? I was used to boys checking me out at college but not an adult like Trey. 

By the time I stripped down to my panties and “New Kids On The Block” T-shirt (my usual sleep attire), I decided that my concerns were unwarranted. After all, I just met him and first impressions are often wrong. I was sure that I was being over-protective of my mother. I eventually fell asleep, content with the possibility that my mom had found a nice guy.

***

I awoke later that night to a strange noise coming from within the house. Lying there in my bed with my eyes still closed, I waited to hear the noise again.

And then it came. Faintly, at first, but then becoming louder. “Ah… Ahh… Ahhh … Ahhh…. Yesss!” came my mom’s muffled voice, each utterance followed by a creak from her queen-sized bed in the next room. 

“Ahhh…Ahhh …Ahhh… Ahhh…Ahhh…Ahhh…Ahhh…Ahhh…” 

I couldn’t believe what I was hearing and didn’t know whether to laugh or to be COMPLETELY DISGUSTED. I refused to open my eyes as I realized that my mom was getting laid in the next room! Pulling the covers over my head, I tried to fall back asleep. But my mom’s groaning continued and, to my amazement, became even louder. 

Doesn’t she know I can hear her?

“Ahhh… Ahhh… Ahhh…. Yesss… Oh, Christ, Trey… Ahhh… Ahhh… Ahhh!!!”

They kept at it for another 20 minutes before I became thirsty and figured I could make a quick dash for a glass of water before my mom and Trey were finished screwing. I cautiously tip-toed out of bed and down to the kitchen. After sipping my water, I started to make my way back to my bedroom when I heard my mom’s door creak open. Panicking and not wanting my mom to think that I had heard what was going on, I swiftly ducked into the utility closet in the hallway next to her bedroom. 

I barely closed the door before someone came out of the bedroom. My heart was pounding through my chest and I prayed to God that my Mom wouldn’t catch me. How utterly embarrassing that would be! Through the slits in the door, I could see Trey’s form come out of the bedroom, wrapped in my mom’s bedspread. He slowly made his way into the bathroom across the hall and turned on the light. I was surprised that I could see directly into the bathroom from my vantage point! 

Along with his hair sticking up, I noticed a shiny layer of sweat on his face and upper body. He obviously had been working hard in there. Without closing the door, Trey let the bedspread fall to one side and began peeing. I made an audible gasp as his penis came into my view. This caused Trey to turn his head suddenly in my direction looking for the source of the noise. I tried not to breathe or move as he peered into the hallway for a couple of seconds before bringing his attention back to the task at hand. 

His penis seemed enormous! I was mesmerized and I could not take my eyes off it. The only other penis I had ever seen in the flesh was my boyfriend’s, Shawn, and his was way smaller than Treys! I began to feel that “tingling” sensation in my pussy and I felt myself becoming wet as Trey continued peeing. Trying to fight the sensation, I quickly realized it was a lost cause. I could see his dick from the side and even though it was flaccid, it had to have measured at least 4 or 5 inches and I don’t know how thick. His balls were large, too, surrounded by a thick forest of black, curly hair. 

It reminded me of Health class earlier that year when we had studied sex education. When question time came, the class smartass had asked the Health teacher about the average penis size to the amusement of everyone else. Trying to maintain order and to keep the discussion relatively serious, the teacher answered that most research suggested that the average penis length was 5-6 inches when erect. Trey’s was obviously a lot bigger than average!

I brought my fingers to my crotch and could feel that I was soaked now. I gave myself a little rub in order to provide some relief. Trey seemed to piss forever, but he finally finished up after giving it a couple of final shakes. As he bent over to retrieve the bed sheet, his hairy, muscular ass was exposed briefly before he covered up and turned off the bathroom light. 

Walking back through the hallway into my mom’s bedroom, I could have sworn that I saw Trey briefly turn toward the utility closet and smile. But it was dark with all the lights off, and my eyes were re-adjusting, so I could have been mistaken.

I waited five minutes before scurrying back into my bed, making sure to change my panties first. It took another half hour before I was able to fall asleep.

***

Over the next several weeks, my Mom saw quite a bit of Trey both on the weekends and during the week. He always stayed the night and I was consistently treated to sounds of my mother getting relentlessly plowed by him. It became so commonplace that I learned to sleep through it. My mom would insist that Trey leave very early in the morning before I awoke because “I don’t want Jessica to know that we are sleeping together, yet.” (I heard her say this to Trey through the bedroom wall on multiple occasions, unbeknownst to her). 

During this time, I typically saw Trey when he watched TV with us or when he picked up my mom for a date. He continued his penetrating stares at me, which, in itself, wasn’t too big of a deal. What became a problem is how “touchy-feely” he became around me. It started out with innocent kisses on the cheek, followed by long hugs, and eventually inappropriate touching. By inappropriate touching I mean stroking my hair, grabbing my hand or arm, and even patting my behind sometimes. Trey always did it very subtly and usually when my mom was not in the room. 

Since I was young, I really didn’t know how to respond to it and my Mom was obviously on cloud nine with this guy so I certainly didn’t want to say anything to screw-up her relationship. I decided I could handle it for the sake of my mom’s happiness.

***

One Saturday night, I heard my Mom and Trey come in real late. They were real loud and I could tell they had been drinking a lot. My Mom actually sounded worse than Trey (she could never handle her alcohol very well) as she was slurring her words loudly and stumbling around. Things became quiet pretty quick and I wondered if they had fallen asleep. I rose from my bed and peeked out my bedroom door which I always kept slightly cracked. 

I peered out just in time to see Trey carrying my passed-out mom into her bedroom. Someone’s not getting any action tonight, I laughed to myself as I slid back into bed and eventually fell asleep.

I’m not sure how much time had passed before I was awoken later that night by another noise. Lying in silence, I waited to hear the noise again. As usual, I was sleeping on my stomach and was too tired to turn over to investigate.

Several seconds later, I heard the noise again. Absolute PANIC swept through my body as I realized that someone was in my bedroom!

I was paralyzed with fear as I heard a person kneel next to me. My mind started to race. I was certain it wasn’t my Mom since she always made every effort to respect my privacy and would have certainly knocked on my door to wake me before entering. Plus, considering how drunk I saw her earlier, I knew she’d be passed out. When the strong combination of cigarettes and Polo cologne hit my nostrils, a feeling of terror arose from the pit of my stomach. I realized that it could only be one person- my mom’s boyfriend, Trey.

I don’t know how much time passed (maybe a minute or so?) as I pretended to be fast asleep- heavy, rhythmic breathing and all. What in God’s name is he doing in here? 

I could “sense” him staring at me which was quite unnerving. It was almost as if he was deciding what he wanted to do. Eventually, I could feel my comforter and bed sheet methodically being pulled off my bed and from my body. He took his time with this task and appeared to be taking every precaution not to wake me. 

I could feel the adrenaline being pumped into my bloodstream but I was way too scared to react in any proactive way. I felt weak and powerless. 

Trey finally pulled off the last bit of covers and there I was dressed solely in my “New Kids On The Block” T-shirt and yellow, cotton panties. I felt extremely vulnerable and was hoping it was all a bad dream. 

All of a sudden, my butt felt cool and I realized that Trey had pulled up my T-shirt. I next felt warm fingers slide inside my panties and over my butt. He was stroking my butt cheeks and lower back in a gentle, circular fashion with his fingers. I cringed as I thought of this old, perverted man touching my body. If I wouldn’t have been so scared, I think I would have cried.

Soon, I felt a second hand move in under my panties as he continued to massage my ass. Goose bumps started to form on my bottom and lower back and I was shocked to realize that his touches felt sort of pleasant. 

Trey eventually moved his fingers down into my butt crack. I bit my lip as one hand gently pulled one butt check to the side while the other delicately rubbed the area around my anus with a finger. My breathing became more rapid. He seemed to be making little circles around my anus. On one hand, I was kind of disgusted, yet the fact of the matter was that he was starting to make me very wet no matter how much I tried to ignore it. I was confused by this reaction of my body. 

His hand subsequently slid down into the area between my anus and my pussy which he manipulated for a while. Without realizing it, I parted my legs ever so slightly. I was praying that Trey didn’t notice how my body was responding. 

Suddenly and without warning, his other hand moved down also, moved my panties aside, and started rubbing my pussy firmly. Trey seemed to know exactly what he was doing as he carefully caressed my clit and lips. If he was surprised by the excited state of my cunt, he didn’t act like it. Electrical shocks went through my body as one hand stroked my clit while the other fingered my pussy. I was losing track of time. 

Trey continued to expertly finger-fuck me for a few more minutes, while he manipulated my clit with his other hand. As he thrusted with his fingers, I eventually found myself slightly thrusting back with my ass. I couldn’t help myself. I wasn’t thinking about anything at this point except the pleasure. It is amazing to me how I was able to keep quiet through it all.

Just then, a loud thump came from my mom’s bedroom. This must have frightened Trey for he quickly pulled away and exited my bedroom. I subsequently heard the faint squeak of my bedroom door closing behind Trey.

In stunned disbelief, I turned over, pulled down my t-shirt, and finally opened my eyes. I crawled along my bed to find the covers but stopped when I felt a damp spot on the bed. I had really made a mess of the sheets. 

I cleaned myself off with a spare pillowcase and then laid a clean pillowcase over the wet spot. Sliding back into bed, I pulled the covers up to my neck. I didn’t know what to think, feel, or do. What just happened was a disaster! I just wanted to sleep. 

Suddenly, in one quick motion, I threw off the covers, scurried to my bedroom door, and locked it. I returned to my bed feeling a little more secure, but knowing deep down that everything had changed.

***

By the time I awoke the next morning, Trey was gone as usual and my mom was in the kitchen making breakfast. I went downstairs into the kitchen even though I wasn’t very hungry.

“Good morning, Sweety,” my mom greeted me as she cooked some eggs on the stove. She looked like hell. Obviously hung over, her hair was a tangled mess, her face was pale, and her eyes were bloodshot.

I sat down at the table and asked lethargically, “Hungover, mom?” 

My mom turned around quickly, “Is it THAT obvious, Jessie?”

“Yes.”

“Well, I guess I have to start watching how much I drink. I don’t want Trey to think I’m a lush!” my mom chuckled.

“Like he should talk,” I whispered sarcastically under my breath.

“What, Sweety?” my mom asked.

“Nothing, mom. I just said I think I’ll go for a walk.”

“Oh, you don’t want any eggs?”

“No thanks,” I rose from the table and left.

***

I was still in shock two days later as I contemplated what had happened to me. To make matters worse, Trey was coming over to watch a movie with us later that night after work; the first time I would see him since “the night”. Briefly, I considered telling my mom about what had happened. The guy was obviously a pervert and my mom needed to know. 

But I couldn’t bring myself to do it for several reasons. First, I was way too scared- what if she didn’t believe me? I just knew that Trey would deny it ever happened and I certainly couldn’t prove it. It was simply his word against mine and I was horrified to put my mom through that.

Second, it would absolutely wreck the first successful relationship that my mom had been in since Dad passed away. She had not been this happy in years and it would be a shame to ruin it for her. 

Finally, something that probably bothered me more than anything was that I was ashamed by the way my body had responded to him. It was like I couldn’t control my reactions. Did I encourage it in some way? It seemed pretty stupid to accuse someone of molesting you if you actually enjoyed it! How could I be disgusted by someone on one hand but turned on by him on the other hand?? Maybe I’m going crazy, I thought.

In the end, I decided to act as if nothing had happened and to avoid him. Trey never knew that I was awake that night, so he doesn’t know that I know what he did. And what is the chance that he will try it again? In fact, Trey very well could have been very drunk (like my mom) that night and didn’t realize what he was doing. I rationalized that it could have been a terrible mistake. As long as I stayed away from him and locked my bedroom door at night, there should be no more problems in the future. Unfortunately, this is the type of naive thinking that only an 18 year old girl would believe.

***

Trey came by as expected later that night. As he noticed me on the love seat in the living room, a shit-eating grin appeared on his face. I did my best not to make eye contact with him.

“Hi Jessica!” he announced in a confident tone of voice as he walked over in front of me. 

“Hi,” I answered flatly stretching my head around him to see the TV. “Do you mind? I’m trying to watch the movie!”

My mom spoke up from the couch, “Jessie, rewind the movie so Trey can watch it from the beginning. I’m going to get Trey a drink. I’ll be right back.”

Trey sat down on the couch after giving my mom a kiss on the cheek in passing. As usual, he just stared at me as the tape rewound. 

He took a quick look back at the kitchen and then spoke to me in a hushed tone, “Jessica… I know you were awake Saturday night.”

My stomach jumped. “What are you talking about?” I answered staring blanking at the TV. 

“C’mon, Jessica. I know you enjoyed what I did to you and I’m going to do a lot more to you.”
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 college 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 collegework 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 college 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 college. John was Riana’s boyfriend and it was common knowledge at our college 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 college 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 college 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 college!” 

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 college, 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!!!!”
Trey finally slipped his tongue out and spent some time licking the area between my pussy and anus, which felt incredible! Trey could tell I was enjoying this and he subsequently went a little higher to lick around my anus. 

This is so gross, I thought! His tongue gently rimmed around the opening my ass in circular motions, similar to what he did with my clit earlier. Trey reached around and rubbed my clit as he continued with my backside. It felt WONDERFUL, I must admit.

“Ah!” I gasped as Trey put the hot, moist tip of his tongue up my ass. “Ohh…Ohh…Ohh, Treyyyyyy,” I continued to softly verbalize. “What are you doing to me?? Ohh… Ohh…Ohh, God!” I didn’t seem to be able to control what I was saying. I spread my legs further apart hoping his tongue would go up my ass further. 

The combination of him licking my ass while manipulating my clit was driving me over the edge. I was breathing so heavy it must have seemed like I was having an asthma attack! I had been doing my best to try and keep quiet, but I’m sure I was being way louder than I thought. It would be a miracle if I didn’t wake up my mother.

I finally turned my head toward him and whispered, “You’re going to make…..you’re going to make… me cummm…. again!” 

Then, he suddenly stopped, picked me up like a rag doll, and threw me on my bed. He must have taken off his boxers without me noticing for he was now standing naked before me with the biggest hard-on I had ever seen. It literally took my breath away. 

Trey’s cock was just plain intimidating! It had to be at least 8 inches long and quite thick. I honestly didn’t know if I could take it all and I was scared that I was going to be in for some major pain.

But Trey didn’t give me much time to think about it. He swiftly jumped into bed next to me and demanded, “Suck my dick, Jessica.” By this time, I would have done anything for him.

I approached his cock with a combination of fear and lust in my veins. Grabbing it, I was amazed to see that I couldn’t get my whole hand around it. I started to gently pump the shaft a bit. It was very hot, solid and literally throbbing. I remember thinking how different it looks than Shawn’s little penis. 

Becoming impatient, Trey commanded, “Put it in your mouth!”

I carefully put my mouth over the head of his penis and tried to take as much into my mouth and throat as possibly. After only a few inches, I gagged and had to take it out. Trey seemed to find this particularly amusing. I then started sucking the head of his tool, pumping the rest with my hand. It was the best I could do under the circumstances. My goal was to make Trey feel as good as he was making me feel. 

Occasionally, I had to stop sucking him to alleviate the growing pain in my jaw. In these instances, I would lick the length of his shaft all the way up to the head like I saw some woman do once in a porno movie. When I placed the tip of my tongue in his pee hole,

I noticed that a tiny bit of sticky liquid was already coming out.

“Lick my balls,” Trey said at one point as he pushed my head further down. I had to find my way through his forest of pubic hair before I took one of his mammoth testicles into my mouth. It was a neat sensation to have them in my mouth. I alternated between the two but was careful to be extra gentle with them. 

After a while, Trey pulled me up and said “Jessica, I am going fuck you now.”

Without waiting for a response from me, he swiftly flipped me over onto my knees and pushed my head into my pillow so that my ass was in the air again. I felt Trey mount me and I braced myself, fully expecting him to plow me immediately. 

Eventually, Trey had his penis lined up with the opening to my pussy, but then he seemed to change his mind. He proceeded to run it along my ass, pussy, and clit for a while. God, I was DYING for it at that point. I knew it was going to hurt but I didn’t care since I was so horny. 

I finally became impatient. “Please Trey… do it!!” I pleaded through my pillow. He seemed to be playing some sort of cruel game with me! 

I felt Trey lean over, pull my hair to one side, and start to suck the back of my neck. He then grabbed my dangling tits as rammed half of his dick into my pussy. 

“Ahhhhh,” I gasped. It felt like he was ripping me apart. He started to pump slowly as I began to adjust to his enormous size. Intense pleasure started to replace the sharp pain as he sped up. 

Within a couple of minutes, Trey had thrusted the remainder of his cock into my tight pussy. I groaned into my pillow and my eyes filled with tears. He was pumping me with everything he had. 

It felt like his penis was going into my stomach. I could hear Trey grunting with every thrust as he pinched my dangling nipples. 

He started to talk really dirty in my ear. “Ohhh Jessica…you’re such a good fuck. I have dreamed of fucking you ever since I saw you that first day on the couch!”

Trey continued, “I love fucking your body. Your body was made for my cock to fuck…. You will always be my little whore! Understand??”

“Yessss…” I groaned in response. 

It was about then I had another series of orgasms; one after another as Trey continued to violate me. 

Soon, Trey pushed me over, lied down on his back and sat me on top of his prick. As I eased myself onto him, I realized that this position was more comfortable for I could control how deep and how fast we fucked. We went a long time in this position. It felt especially good when Trey reached around and inserted the tip of his finger in my ass.

After a while, I was beginning to wonder if Trey would ever cum. He cock was still harder than ever inside of me. 

Before I could contemplate that thought further, Trey flipped me on my back, positioning my legs over his shoulders. I later learned that he cums easiest this way. Trey began with long, slow strokes, where he pulled his cock almost the whole way out of my cunt, before slipping it back in to the hilt. 

I was enjoying the intensity with which he was screwing me. We were both sweating profusely and I could actually see beads of sweat rolling off Trey’s body and onto my bed. 

As Trey approached his climax, he picked up the pace. I wanted him to cum very much by this point since my pussy was really beginning to hurt. 

I remembered that my friend Carrie once mentioned to me that the easiest way to get a guy to cum is to talk sexy to him. I was ready to try anything by the point in order to make Trey cum. 

I leaned up and whispered into his ear, “Trey, Fuck me…. Please, fuck me, Trey. Ffffffuuucckkkk Mmmmeeeeeeeee.”

This seemed to help as Trey accelerated his thrusting signaling that he was getting closer. 

So I continued in a whisper, “Fuck me, Trey! Fuck my pussy. You’re doing a good job fucking my pussy, Trey! Do you like fucking your girlfriend’s daughter?!”

“Ohh, Trey. I love your cock! Faster! Ohhhh… Ohhhh… Ohhhh… Ohhhh… You’re making me feel so good!”

Trey was getting real close now and I started to buck my pelvis toward him as he banged me in order to give him deeper penetration. “C’mon, Treyyyy. Keep on fucking me! Ohh… Ohh… Ohh… God, Treyyyy…I want you to cum, Trey….Please cum for me, Trey!!” 

He was really close now. “Ohhh…. Ohhhh…. Cum for me, Trey… I want you to cum inside my pussy!”

The next thing I knew Trey was fucking me so hard that I thought my body would be bruised in the morning. He then gave one final, powerful thrust and I felt him absolutely EXPLODE inside my cunt. Falling in a sweaty heap on top of me, I felt several powerful squirts deep within my cunt. 

I lied there with Trey’s penis still inside of me, unsure what to do next. My eyes were closed and I could distinctly smell the aroma of sex. After a minute or so, Trey sighed loudly and rolled off of me. My body was tingling all over and I felt his jism start to leak out of me. 

He rose from the bed and I heard him fumble around for his underwear. Trey subsequently gave my tit a quick squeeze before whispering confidently into my ear, “This is just the beginning, Jessica.” With that, he walked out of my bedroom, presumably to go back to my mom.

That was the start of a 6 month odyssey which almost destroyed my family.

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