It was the summer between my senior year of high school and freshman year of college. I was working nights as a busboy, smoking weed almost daily, although I’d been caught by my parents and threatened by my father that if I’d do it again, he’d kick me out into the street. That would have been a real disaster because I couldn’t possibly function on my own out in the real world. I had no confidence, was constantly being told by dad that I wasn’t measuring up, and had basically become a loner. I was still a virgin and had only kissed a girl once – and she was so d***k that she ended up throwing up in the front seat of my dad’s car; of course, I didn’t own my own transportation. I tried to get the word out in high school that I’d “gotten laid” on a trip up north with a girl I’d met by a lake, but it was a blatant lie and probably fooled no one.
What I did have was a very active fantasy sex life that had morphed into some really out-there behaviors that went beyond simply jerking off. It all began with my father’s stack of Playboys in his bedroom closet; I could hardly wait for when my parents went out for an evening – or, better yet, away for several days – so I could look through those pages, heart thumping, hands trembling. I particularly liked the yearly “Sex in Cinema” issue that showed photos from that year’s movies – mainstream and adult – often with a man and woman in a sexual position. Each year there seemed to be a photo from a movie that had adultery in its plot, and that’s when my fantasies really took off.
One afternoon, while jacking off after a magazine session, I pictured myself as a confident, seductive middle-aged man making love to my mother, an adultery “scene.” I closed my eyes, saw my mother’s face as if she were underneath me as I pumped away – and shot one of the biggest loads of my life. I was 14. The guilt I felt after was immense, but the intensity of it was even more powerful. From then on, almost all of my masturbation sessions involved me fantasizing about her.
When I was 16, my folks took a trip to Hawaii while my b*****r was away at college. I had the house to myself for a week and I had the freedom to sneak those Playboys down from the shelf without worrying if one of my parents would come walking through the door. It was a dream come true. One evening, the intensity of the experience got me thinking about ways to liven up my fantasy. As I put a magazine away on my father’s shelf, I suddenly had the idea to look through my mom’s things. First, I went to her side of the closet and flipped through her dresses. Of course, I also went to her underwear drawer and looked through her panties and bras, and by then I had a throbbing hard-on.
I went to the living room, desperately horny, and tried to think. And then it dawned on me.
I went to my bedroom and got my pillow. I carried it to my parent’s room and set it on their bed. With my heart threatening to beat out of my chest, I removed one of mom’s dresses from her closet, and then got a pair of her panties and a bra. I fastened the bra on the pillow (it took me a while to figure out the catch), slipped the panties over the bottom of the pillow, and then the dress over the pillow. Looking at it laying there, dressed up in my mom’s things, I almost came. But there was more to do. Next, I took the freestanding full-length mirror they had in one corner of the bedroom and moved it to the foot of the bed. The only thing left to do was to put on some of my dress clothes so I could play the role of a seductive, middle-aged businessman who had my mom home alone. I almost tripped taking off my jeans and T-shirt, I was in such a hurry to put different clothes on. I put on a tan shirt, brown slacks, and black socks.
I returned to the bedroom, took a deep breath and got down on my parent’s bed next to the fully-dressed pillow. I could see “us” in the mirror. It felt awkward for a moment, and I knew what I doing was wrong and “sick,” but the intensity of the fantasy was far too powerful for me to stop. I began making out with pillow, “rubbing it up”, then slowly undressed it. I slid to the edge of the bed and removed my clothes, standing there with a full-fledged hard-on with a drop of pre-cum at the tip. I returned to the pillow, afraid I was going to come on the spot. I “made out” some more and then sliding down and getting on my knees, I gripped my cock and slid it under the pillow. “How’s that baby?” I moaned. I lowered myself and began humping the pillow. Looking back in the mirror, I saw my ass cheeks rising and falling, my toes clenching – and I couldn’t hold back. I came so hard that my head hurt for a moment. I felt immediate guilt and hurriedly put her clothes away, and the mirror back in its original position. I hurried naked down the hallway to my bedroom as if expecting someone to walk in at any moment. I told myself what a loser I was a few dozen times. In the back of my mind, however, I knew I had to do it again. And again.
I repeated the fantasy pretty much whenever I had the chance. I got home from school earlier than my parents and would even do it then – although I was paranoid I would leave a stain on their bedspread, or put her clothes away so sloppily that she would notice. They took vacations every year, and I repeated the routine almost every day they were gone. I talked during my fantasy as if I were the man in charge, even calling out my mother’s name. I secretly bought a tape recorder to record my talking, and listened to the tapes frequently, always focusing on the moment I came and the groans that came with it. I used her bathing suits as part of the fantasy and, as always, had the mirror positioned where I could “watch.” I was deathly afraid of getting caught, but I was always careful. Or so I thought.
I had the day off for some reason. My mom was at work and my dad was away at some conference, again. I had the home gloriously to myself. I took my time, had breakfast, took a shower, and then set up the fantasy once again. I used one of her new dresses this time. I remember thinking how this fantasy never got old. Again, I undressed the pillow slowly as I made out with it – watching myself in the mirror – then got naked myself. I pretended I was sucking on one of my mom’s small titties as I teasingly put the end of my cock at the end of the pillow. Then I slid it in. I looked back in the mirror, watched my ass rising and falling, and thinking how good it felt – again. “Oh god Carol!” I groaned, using my mom’s name.
And then I heard my mom’s voice.
“Oh my god! What in the world are you doing?”
I looked to the doorway and there stood my mother, her eyes wide open in shock.
“What..what are you doing home?” I stammered and instinctively rolled over. In doing so, I exposed my fully-erect cock to her and I quickly covered myself with my hands.
“The question is, what are you doing?” she demanded.
Not knowing what to say or do, I leapt off the bed, grabbed up my clothes and brushed past her to my bedroom. I slammed the door behind me and waited. But she either stayed where she was or went to another room. I thought I heard her crying. I dressed quickly and decided to make a run for it. I ran through the kitchen – from where I could notice her standing in the living room, her head covered with both hands – and out to the garage where I got my bicycle. I decided it was time for a long ride.
I knew I couldn’t stay away forever. I had to face up to it sooner or later – that, or runaway, but I had no place to go and hardly any money in my savings – and I made my way home in the early evening. I never felt such a sense of dread as I did as I pulled my bike into the garage and entered through the kitchen. I instantly saw her sitting on the living room couch, a glass in her hand (filled with her third vodka of the day I later found out). Her legs were crossed and her foot dangled nervously by her knee. I desperately wanted to hide in my bedroom but knew I couldn’t wait forever. I walked into the living room. My mouth felt like it was filled with cotton.
“Mom,” I managed. “I don’t know what to say. I….I, I’m not sure what came over me this morning.”
She took a sip from her drink and looked at me.
“It wasn’t your first time,” she said. “At least it’s not if those tapes I listened to were any indication.”
I’d completely forgot about the tape recorder. There was a good hour of recorded fantasy sessions on that particular tape. I used her name often, including pet names my father had for her. I talked in my fantasy about how my cock (as the confident seducer) was bigger than “your husband’s.”
“It wasn’t always, I mean, not every time was like that,” I said. But I also knew that on the tapes I talked about taking her dress off, and things like “Let’s get that bra off of you.”
“What in the world ever came over you to do something like that – many times?” she answered.
I took a deep breath. There was no good answer.
“It just, I just, well, it was just normal stuff….”
“Like masturbating?”
“Yes, like that. And then it got boring or something and for some reason it just took on another life. I’m so sorry mom. I promise I’ll never do it again. And, please, please, please don’t tell dad. He’ll disown me, if he already hasn’t.”
She sipped her drink.
“Masturbating at your age, at any age really, is normal,” she said. “But what you’ve been doing is something different.”
“I know. And I’ll stop. I promise.”
“I’m your mother, Bryan.”
“I know. It’s sick and wrong. I don’t know what I was thinking.”
She stared at me for a moment, and then her eyes focused somewhere far away.
“It’s natural, I’ve heard, for boys to have fantasies about their mothers,” she said, quietly.
“I’ve heard that too,” I chimed in, without having any idea whether it was true or not. Most guys my age didn’t even admit they masturbated. And I assumed most of them were getting laid for real, not resorting to crazy fantasies.
She looked back at me.
“But I don’t think any of them take it to your extreme, Bryan. I mean, it’s like a whole ritual you have set up.”
She sighed.
“I know you have trouble meeting girls,” she went on. “I know you have a lot of problems with your confidence and your father doesn’t help with his constant criticizing.”
“He’s always critical,” I said. “Always.”
She sighed again.
“I know it,” she answered. “He’s very critical with me, as well, as I’m sure you see. Sometimes I feel like I can’t do anything right. And his temper is out of control.”
“I wish he treated you better mom,” I said, relieved that we were on to a different topic, at least for now.
She was silent for a moment.
“Your father is not an easy man,” she said. “As a result, our marriage isn’t very happy. You have no idea, Bryan.”
Tears welled up in her eyes. She took another sip from her drink.
“You deserve better mom,” I said. “I don’t know why he treats you like he does.”
She looked up, her eyes moist, and smiled a little.
“That’s very sweet of you to say,” she said. “These last few years have been very difficult. We’re a couple in name only. We do things together with other couples, we go on vacations, but it’s like we do those things not because we want to, but because it’s expected of us as a couple. His stupid bosses expect it. But that’s not even the whole story.”
“What do you mean, mom?”
She looked down again, thinking. Then she took in a deep breath and let it out, before looking back up at me.
“He’s having an affair,” she said in a hushed voice. “He’s been having one for years, as it turns out, but he doesn’t know that I know about it, yet. “
“Mom, that’s….awful. I mean, I guess I’m not surprised, but …”
“You mustn’t tell anyone, honey,” she answered.
“Are you going to get a divorce?”
“I don’t know what I’m going to do,” she said, and then began sobbing. She placed her hands over her face.
At that point I wasn’t sure what to do, but I decided to sit down next to her and tentatively put an arm around her. She was still in her work clothes – a light blue blouse and cream-colored slacks. I was aware of how bizarre the day had become; I’d been caught doing something awful by my mom, but now I was trying to comfort her in my own awkward way.
“I’m so sorry, mom,” I said.
She nodded her head, but was still crying.
“You deserve so much better,” I added.
She quit crying, took a deep breath, and turned toward me.
“That’s so nice of you to say,” she said. “I sometimes feel like I don’t deserve anything.”
“Mom, you deserve everything. I mean, you’re pretty and nice – well most of the time.”
We both laughed and she leaned her head against my shoulder. I could smell her shampoo.
“You really think so?” she asked.
“Think that you’re pretty? Of course.”
She sighed heavily.
“I don’t always feel very pretty,” she said. “Or, your father doesn’t make me feel very pretty. He’s always on me about my weight, what I wear…god, it’s so frustrating.”
To be honest, my mom wasn’t what you would call “beautiful,” but she was cute in her own middle-class, suburban way. Her hips had become a little wider and, like I said, she had very small breasts. But I’m sure a lot of men would find her attractive – including the businessman/seducer of my fantasies, which now crossed my mind for some reason. The truth is, her leaning against me was turning me on a little – despite our incident earlier in the day and her current state of sadness/frustration. I tried to banish the thoughts, but without much success.
“I think you’re very pretty mom,” I said. “I don’t know what dad sees in someone else that’s better.”
She shook her head sadly. We sat there like that for a moment before she sat up straight and looked me in the eye.
“What you were doing in the bedroom – are you really thinking of me?” she asked, her tone and gaze serious now.
My face turned crimson and I wasn’t sure how to answer. I could lie and say I really wasn’t thinking of her during the fantasy, but there was no lying to her at this point.
“Mom, I … yes I do think of you and I’m so sorry.”
Then she did something that completely surprised me. She put her hand on mine.
“Stop saying you’re sorry,” she said. “I forgive you. As a matter of fact ….”
She stopped herself in mid-sentence and looked away.
“As a matter of fact what, mom?”
I thought she was going to cry again for some reason but she took a deep breath and looked me in the eye again.
“I guess, it was flattering for someone to think of me in that way,” she said.
“You mean, sexually?” I managed, fully aware that my heart was starting to beat faster. Things had taken a turn in a direction I’d never imagined.
She was silent again for a long time and she stared at the floor. I could tell she was thinking of what to say next. Then she turned back to me.
“Yes,” she said softly. “Sexually. You were clearly very excited when I walked in on you like that.”
The thought of me rolling over when she yelled out from the bedroom doorway, my throbbing cock standing straight up, crossed my mind again. She’d clearly seen it in all of its glory before I covered myself with my hands.
“I know it’s wrong to think that,” I began, but she put a finger to my lips gently.
“Stop apologizing, Bryan. I’m not sure what’s right or wrong at this point, but it was, well, very flattering that you had, or have, such an intense desire for me in that way. At first I was shocked when I listened to those tapes, but the more I thought about it while you were gone, I couldn’t help but feel desired. Wanted. Beautiful even.”
Our eyes met and we stared at each other for what seemed like an eternity.
“Bryan,” she said, “I can’t believe I’m going to ask you this, but would like to have your fantasy right now?”
“What!? Mom, you mean…”
She leaned forward and put her lips on mine before I could finish what I was saying. I thought it was going to be a quick peck, but she lingered. Her lips felt so soft and warm against mine. I got the hint and kissed her back. The next thing I knew, her tongue was against my teeth. I opened my mouth slightly and our tongues mixed. And then she pulled away.
“My god,” she said. “I can’t believe what I’m doing here.”
She stood up, her back turned toward me. She reached for her drink, took a big gulp, then headed to her bedroom. I sat there, both disappointed and incredibly aroused. I couldn’t believe that I’d French-kissed with my own mother! But now she’d changed her mind about my fantasy.
Or, so I thought.
After several minutes I heard her call from the bedroom. At first I thought I was hearing things, but then she called louder. I got up and went to her room. The door was closed.
“Mom? What is it?”
“Honey, come on in please.”
I opened the door and looked in. What I saw almost brought me to my knees – there was mom on the bed, in the same dress I’d used in the fantasy earlier, with the mirror pulled up to the foot of the bed.
“Mom? What…”
“I asked if you wanted to have your fantasy,” she said. “I assumed you’d say yes.”
“You mean…?”
“It’s still your fantasy, honey. Except you’re not going to use your pillow.”
She reached a hand out toward me. I moved forward, almost in shock.
“Lay down next to me, sweetie,” she said.
My heart was beating so hard I could hardly breathe. I eased myself on the bed next to her and laid on my back.
I saw our reflection in the mirror. It was too incredible to believe.
“Honey, can I ask you something?” she said.
“Yes. Sure,” I stammered.
“Are you a virgin sweetie?”
My faced turned crimson again.
“Yes. I am, mom.”
She smiled at me sweetly.
“I thought so.”
She then reached her hand over and began softly rubbing my chest.
“Honey?” she asked again. “I need you to promise me that you’ll keep this a secret.”
“Yes,” I replied, almost blurting it out. “I won’t tell anyone. I promise.”
“Neither will I,” she said, and then leaned over and put her lips against mine. This time our tongues meshed from the start. While we kissed her hands roamed over my chest and stomach. I was as hard as a rock. From the little moaning sounds she made while we kissed, I could tell that she was liking it, as well.
She pulled away from our kiss and put her mouth against me ear, whispering, “Do what you do in your fantasy honey.” Then her lips were back on mine.
Not sure where to start, I placed me hand on her dress, just below her breasts. I felt her quiver slightly. I realized I couldn’t be the fearful little boy anymore who had no confidence. I moved my hand on one of her breasts and squeezed softly. She lifted her head back and moaned softly.
“That’s it, sweetie,” she said. “Just like that.”
I began squeezing and rubbing both breasts while her fingers went from my stomach to chest and back again. I happened to glance up and saw something on the small table next to her side of the bed. It was the tape recorder. I could see the red light that indicated it was recording.
“Do exactly what you do in your fantasy,” she said, hungrily.
“OK mom.”
I reached behind her and she lifted her back slightly. I found the zipper of her dress and pulled it down as far as it could go. She sat up, knowing what she needed to do, and I slipped her dress down over her shoulders and arms. Her pale skin looked heavenly. She had on one of the simple white bras I frequently used in my fantasy.
She remained sitting up and I knew what I had to do next. I reached behind her, trying not to be too clumsy, and found the latch of her bra. I fumbled for a few seconds but miraculously got it undone in little time. I took a deep breath and pulled the bra off. Her breasts were small, but the brownish nipples were protruding like little erasers.
“They’re beautiful, mom,” I said.
She grabbed her right breast with her right hand and slowly eased it toward me. I knew exactly what she wanted and put my lips and mouth on it.
“Oh god!” she groaned. “Yes sweetie. Just like that.”
I alternated between flicking my tongue on her nipple and sucking her breast, which fit entirely into my mouth. She played with her other breast and nipple as I did this. Our bodies trembled.
“Oh god, oh my god!” she said. “It’s been so long.”
As I continued to suck and lick her breast she arched her head back, her mouth in a grimace. But it wasn’t one of pain.
“Oh god!” she said. “Oh my god! Don’t stop sweetie! I’m going to….I’m going to, aaaahhrrgh!”
She groaned loudly for what seemed like an eternity. I’d just made my own mom come by just sucking on one of her breasts.
She caught her breath.
“You have no idea how good that felt,” she said. “And we’ve barely started.”
We laughed. Then our lips were back together. And her hand roamed below my stomach, below my belt, and directly to my throbbing cock that was threatening to burst out of my jeans. She rubbed it, up and down, and squeezed it gently. Now it was my turn to groan.
As she did this, I reached over and started pulling her dress off of her. I lifted it up over her arms. She was wearing only the pair of blue panties I’d used in my fantasy earlier in the day. I noticed a wet spot in the crotch.
“Take those off, too,” she said.
She lifted her hips and I grabbed her panties by the waistband and slid them slowly over her legs and feet, flicking them to the floor. I saw, for the first time, her bush, and below that the lips of her pussy. Her legs were spread, showing me everything, including her little brown butthole below.
“Oh my god mom.”
“Now it’s your turn,” she said. “Just like in your fantasy.”
I slid off the bed and, with a deep breath, undressed myself. Mom watched me intently. I took another deep breath and pulled my underwear off. My cock was sticking straight up. She groaned.
“Look how excited you are,” she said.
She reached her hand out to me again. I got back on the bed next to her. Our lips came together almost instantly, our tongues mixing hungrily. We bit softly at each other’s lips. And her hand found my cock and began stroking it slowly. I could see her wedding ring as it slid up and down my shaft.
I took my hand, placed it on her bush, and then slowly began rubbing her. The outside of her pussy was wet and I could smell her scent slightly.
“Put your finger in me, honey,” she said, and I obliged, easily finding her slit and hole. My finger slid in slowly. It was so warm. So wet. She moaned heavily.
“Oh, yes,” she said. “There you go honey. You got it. Just like that. Just like that!”
Her hips rose to meet my finger’s probing. I slid my finger in and out, at first slowly, but then faster as her moans increased.
“Yes!” she said. “Oh yes! Oh baby! Mom’s going to come again!”
Her whole body shuddered and she gripped the bedspread with both hands, her teeth gritting, her mouth in that grimace of pleasure again. Finally, she caught her breath. She opened her eyes and looked at me.
“Honey. I want you to make love to me now. I want you inside me. Are you ready?”
“I’ve never been more ready for anything in my life, mom,” I answered. “You might have to help me though.”
“I’ll help you, sweetie,” she said softly. “I want to be your first.”
I moved on my knees to between her legs. Slowly, I lowered my hips until the tip of my cock was right at her bush. She reached down and grasped it in her hand.
“Honey,” she said. “I want you to look at me when it happens. OK?”
“Yes, yes.” I said. “Oh god yes.”
“Here we go,” she said, and I lowered my hips some more.
“Look at me baby,” she said, and our eyes locked.
Slowly, I felt myself enter her with the help of her hand. We both groaned as we continued to stare at each other. The sensation around my cock was beyond what I imagined. She was warm and the inside of her pussy was agonizingly soft. Soon, I was completely inside her.
“Do you like that sweetie? Do you like how that feels?” she said breathlessly.
“I can’t believe how good it feels,” I said. “Oh, mom.”
I lowered myself completely on top of her.
“Fuck me now,” she said. “Fuck me, honey.” I’d never heard her use the word before. But she was hungry for sex – so very hungry.
I began moving my ass up and down. My cock throbbed as it slid in and out of her.
“Look in the mirror, baby,” she said. “Just like in your fantasy.”
I looked back and saw my ass rising and falling. I could see my cock inside of her as my balls moved against her asshole. Her toes curled and uncurled.
I put my cheek against hers and she talked in my ear as our bodies meshed.
“That’s it baby,” she whispered, her breath warm against my ear. “Make love to your mom. Fuck your mom with that hard cock of yours. Just like that! Oh yes! Do you like that baby? Do you like how it feels?”
“Oh my god yes,” I said. “It’s better than I ever imagined.”
I looked back again and saw in the mirror that her hands were grasping my ass cheeks. Her feet and curled toes were in the air, her legs slightly pulled back. I watched again as my cock slid in and out her.
Our pace increased and her eyes closed as she moaned and made little noises.
“Oh honey!” she said. “You’ve done it again! Mom’s going to….I’m going to…aaaaaaaaaahrrrrgggg.”
As she came I instinctively pumped harder and her climax lasted for what seemed like forever. Meanwhile, my cock was feeling that incredible sensation when it’s getting ready to explode.
“Oh mom,” I said. “Oh mom! I’m getting close!”
“Yes baby!” she said. “Yes, come for me. Shoot your load inside me!”
“Getting close!” I managed. “Almost there, mom!”
I made three more rapid thrusts and then I came, shooting my load deep inside her. I groaned loudly and arched my head back, eyes closed.
“Oh my god!” I said. “Oh there it is!”
My orgasm continued for several seconds. Just when I thought I was finished, another spurt came from the tip of my cock. I clenched my ass cheeks tightly.
“Yes baby,” she said, her voice barely audible. “Oh yes. Such a nice big load.”
We lay there for several minutes. She kissed my cheek softly and I kissed her forehead, which had a slight sheen of sweat. The room smelled powerfully of our sex. When I finally rolled off and onto my back, exhausted, my cock was still half-hard and there was a dab of come on the tip of it.
“Catch your breath, sweetie,” she said. “I want you to get ready for round two.”
We both smiled.
“This is your new fantasy, honey,” she said. “I want you to be my lover now. Can you do that, honey?”
“Of course, mom,” I said. “I want to treat you like you deserve to be treated.”
“You’ve already done it, honey,” she said, as her finger traced a line down my chest. “And I want you to do it again.”
We made love twice more that day, my stamina getting stronger with each session. She introduced me to doggy-style, taught me how to properly lick pussy, and even let me tongue her crinkled brown asshole. She returned the favor, her tongue sliding deep into my asshole as she flicked it. Later on, we tried anal sex, though it was often too painful for her.
My “fantasy” continued for several more years. Dad left after a year, which left us with the house to ourselves. But we didn’t confine ourselves to just the house. We fucked in the backseat of her car on a country road, we fucked in a tent in a campground, we fucked in a peep booth of a porno theater, our moans matching the moans of the movie. The sex never, ever got old.