I knew my boyfriend was fooling around with his mom, and I loved it - Part 1

When I turned twenty, I thought the rest of my sex life would look like the previous two years of my sex life: one partner forever, missionary mainly, occasionally in a car to spice things up. My boyfriend at the time, who we’ll call “Dave,” was twenty-one and just as inexperienced.

One night we were cuddled up in his bedroom, heavy petting, and mostly ignoring “The Office” DVD box set we’d play at a loud volume to drown out his squeaky bed springs. (Dave’s family lived near our campus while I was rooming with three girls in a shack, so we’d spend a lot of time “watching” “The Office” in his beautiful family home.) He was kissing my neck and I was stroking his cock through his boxers when one of us mentioned “hall passes.”

“So I get one night with Joaquin Phoenix,” I remember saying, “and two with Gerard Way.” (Shut up, don’t judge.)

“And I get nobody because you’d be way too jealous,” Dave said, laughing into my neck between soft kisses. He was right: the thought of him with another woman, even someone as unlikely as Christina Hendricks, twisted my tummy in tight, angry knots.

“I’ve already vetoed every single one of your big tittied choices,” I said. And as a joke, added: “The only woman left is your mom.”

His cock started throbbing in my hand.

“Shut up,” he laughed, giving me a playful slap on the arm and pulling his cock away—like he’d noticed what I’d noticed.

“Give me that back,” I giggled, climbing on top of him for a tickle war. I was laughing on the outside, but my mind was busy replaying his weirdly urgent reaction, over and over. The way he got achingly hard when I mentioned his mom. The way he jolted back so insecurely and so unlike his normally confident self.

“Your hall pass is your mom, your hall pass is your mom,” I teased, playing his chest like a piano while his hands tickled my hips. His fingers dug in deep and I squealed, thrusting up against his cock. He was so hard I felt it pulsing underneath me.

If my jaw wasn’t hanging open, it might as well have been. My squeaky clean track star boyfriend was attracted to his mom. It made me feel dirty and dumbfounded, but strangely, not jealous. I remember soaking through my panties without really understanding why, and grinding against him while we wrestled. I remember Dave telling me that if I didn’t shut up, he’d make me. I remember: I made him.

He ended all the tickling and teasing when he pulled my lips down to kiss his, pushed my panties to my thigh, slid inside me, and fucked me harder than he’d ever fucked me in our two years together. He held me in place and thrust up so hard and so fast it was almost violent. His eyes stayed closed while he kissed me, never once catching his breath, nose breathing desperately heavy across my cheek. He was so fit in those days—he’d never lost his breath with me before. I wrapped my arms around him and wondered if the intensity and the closed eyes were all because he was imagining her. And it must have been infectious, because then I started imagining her, on top of him like this, tits swaying against his chest, lips locked against his face, holding her son lovingly but needily, feeling closer to him than his girlfriend ever could—all of that, and somehow no twisting, tightening jealousy knot. Only an orgasm. For both of us at the same time.

We couldn’t have been at it for more than sixty seconds, but it was the most powerful orgasm I’d had at that point in my life. I remember slumping against his chest like I’d just run a marathon, legs trembling a little bit, brain totally broken. He held me until I stopped shaking, then smiled at me like nothing weird had happened.

That night, nuzzling into his chest, I wondered if nothing weird had happened at all—maybe it was my dirty mind filling in blanks with “boyfriend wants to fuck his mom” when the correct answer was “boyfriend enjoys tickling me and/or being straddled.” I knew he was attracted to me for me. Normally I crammed all my schoolwork into the weekends, but one time I let him stay a Saturday night in the four-girl shack. I woke up at 2 am to find him jerking off to my swimsuit pictures. (My heart melted. And yes, I finished the job.) Modesty urges me not to mention my hourglass figure, pale white skin, or dark brown hair—so I won’t! But I’m not sure I could compete with his mom.

Mrs. Lawson, we’ll call her, or “April,” she’d insist, was a middle-aged bombshell. She was forty-something, nearly as tall as her son, and the type to modestly hide her curves behind sweaters, cardigans, and turtlenecks that could barely contain her. She was sweet, sunny, and wholesome with me, my boyfriend, and everyone else, but open-minded enough that I’d always figured she was a freak in the sheets. When Dave and I would go upstairs to his room, she’d say, “Make sure he uses protection, Emily!” Then she’d wink at me, more sweetly than flirtatiously, because her and I both knew how funny it was when fully adult Dave would yell “Mooooooooom!” Her husband was almost always away for work, and while I occasionally sensed that this made her sad, she was so cheerful with me and her “man of the house” that the sadness might have been in my imagination. I assumed she had perfected being sexy twenty years ago, didn’t care, and lived off an endless supply of happiness knowing that me and every girl my age were all scrambling to keep up.

She was hot, in other words.

I had no idea where this “hall pass” was going or what I wanted. But the thought of Dave pining for her was so weirdly exciting—and the bottomless tingling I experienced when I imagined him fucking her, even weirder—that I couldn’t help explore my fantasies. Over the next few months, I tried to find out if Dave felt the same way. I knew he’d never admit it, so I ran some sneaky tests.

Experiment 1: While he fucked me, I stroked his hair, looked into his eyes warmly, and whispered, “That’s my good boy. Fuck me just like that. Good boy…” I didn’t know what Mrs. Lawson might say in my position, but that seemed close enough. His grip on my hips tightened. He swelled inside of me. My bulky, six-foot-something boyfriend loved being my good boy.

Experiment 2: After breaking out the motherly tone a few more times, I eased into “teaching” him. “Let me show you what I want you to do with your hands, sweetheart. Good boy! That’s incredible. Don’t stop… Please…” Just like our hall pass night, he fucked me harder and faster. When I roleplayed as an “experienced” woman, he’d hold me down against the bed, hand pressing my head into the mattress while he dug his fingers into my ass cheek, and completely forget his mom was home as he let his balls clap heavily against me, louder and louder. He liked taking direction so much I even convinced him to spank me. “Don’t be afraid, sweetheart. I want daddy to hear. I want him to know how you take care of me. Yes! Just like that…” The spank sent ripples across my ass and echoed through his bedroom. Mrs. Lawson must have heard. I came into those sweaty sheets, thinking: maybe he wants her to hear how good he fucks. After dinner that night, she gave me the most affectionate hug.

Experiment 3: The rough, sweaty sex we’d been having was the best of our entire relationship. And in the month since my “lessons” started, I’d noticed his eyes linger on his mom’s figure when she’d turn around. I couldn’t hold this fixation inside me any longer. I remember pacing around his room when he threw the DVD on. I remember him gently stroking my cheek when he realized I was nervous. “Don’t worry. I’ll be gentle with you,” he said when he slid inside me. I shook my head. “No, sweetheart. What I want is…”—my heart was beating furiously—”I want you to fuck mommy nice and hard.” He lunged forward to kiss me and shut me up. But I felt him twitch inside me, and his heavy breathing was begging me to say more. I pushed him off my lips. “Give me what I want, sweetheart. Fuck your mommy harder. Keep your eyes closed if you’re nervous. Good boy…” The next words out of his mouth were the most perfect I’d ever heard: “Yes, mommy.” I stifled my moan in his chest. His cock swelled tight inside me, pounding furiously, soaked in my juices. The bed shook underneath us, headboard banging against the wall, but we didn’t care. There was no containing this anymore. He gripped the back of my hair and demanded: “Cum, mommy.” My body listened. For a few precious seconds, I was Mrs. Lawson. I felt my son’s love inside of me. I felt his warmth squish my breasts against his chest and felt his hands grab my curves like he’d been pining for them for years. I felt his cum leaking down my cheeks while he kept thrusting, harder…

And then it was dinnertime. Mrs. Lawson asked me if the chicken was okay, and it was delicious, thank you so much for cooking, oh you’re so welcome. Her eyes crossed the table to her son, then to me, and a cheeky smile did a bad job hiding in the corners of her lips.

“Emily,” she asked, “has David told you we’ve been staying at the cottage the past few weekends?”

I swallowed a mouthful of salad a little too soon. “Uh,” cough, “mm, no! No, he didn’t mention.”

Dave’s eyes wouldn’t leave his plate. His mother’s were warm as ever. Mine were wide open. I realized that with all the studying and paper-writing I do on Saturdays and Sundays, I barely spoke to my boyfriend outside school days. A knot tightened in the depths of my tummy. Whether it was the jealous variety, I couldn’t tell yet.

“Oh! Well, they were supposed to be family getaways, but his dad’s been so busy, you know, so the two of us made it a date!” She placed her hand on my cheek and stroked my hair with her thumb. “I know you’ve been working hard on weekends, sweetheart. Would you like to come with us?”