u/tomthumb2026

All week at work, my boss Brian had been grinning like a wolf. He’d text my wife Penny right in front of me during meetings, then casually show me the messages later. “Taking your wife out Friday,” he’d say, voice low. “Gonna treat her right.”

Thursday afternoon we were in the executive restroom, standing at the urinals. He didn’t even try to hide it.

He pulled out his cock, thick even while soft, hanging heavy between his fingers like it weighed something. The head was fat, the shaft veined and long. He gave it a slow stroke, letting it swing, then looked me dead in the eye. “This is what Penny’s getting tomorrow night.”

I couldn’t stop staring. My own dick looked pathetic next to his. I mumbled something about being cool with it, but my face was burning. He laughed, tucked that monster away, and clapped me on the shoulder like we’d just closed a deal.

Friday evening I sat at home like a good little cuck, heart hammering while Penny got ready. She wore the tight black dress I love—the one that hugs her ass and shows off her cleavage. She kissed me softly on the cheek.

“Be good,” she whispered. “I’ll text you updates.”

She met Brian in the lobby of the upscale motel he’d booked. I saw the photos he sent me: his big hand on the small of her back, her smiling up at him like he already owned her. Then came the surprise—our cousin Mark and his wife walked right up while they were hugging. Penny froze for half a second, then recovered like a pro.

“Oh, hey! This is Brian, my husband’s boss. Tom’s running a little late—he’ll be here any minute.”

They bought it for the moment, but the looks they gave her said they knew something was off. Later that night we had to sit them down and explain: we’re swingers, this is consensual, please don’t tell the rest of the family. They were stunned but promised to keep quiet. The whole thing only made my cock throb harder.

Brian took her to that expensive steakhouse downtown. He ordered the best cuts, the finest wine, flaunting his money without shame.

Penny sent me a picture of her plate—perfect medium-rare ribeye, glistening. “He’s spoiling me rotten,” she texted. I jerked off in the bathroom reading it.

After dinner they went back to the motel. She texted me from the sauna: they were alone, making out like teenagers. His hands all over her body in public areas where anyone could have walked in. “He’s such a good kisser,” she wrote. “I’m soaked already.”

Then the room.

She massaged his back and shoulders first, her small hands working over his muscular frame. They showered together—long, steamy, soapy. When they finally hit the bed he fucked her hard and deep, the way I never could. She came on his cock multiple times. Around 2 a.m. my phone lit up with a new message from her:

“He just took my ass. First time. It hurt so good. I think im in love. With his cock lol.”

I stared at the ceiling for hours, replaying that text, my stomach twisting with that beautiful, sick punch of jealousy and lust. I finally fell asleep with my hand wrapped around my dick.

She got home around 10 the next morning, hair messy, dress wrinkled, walking a little gingerly. She kissed me deeply, tasting faintly of him, then pushed me down onto the couch.
“Clean me up, baby.”

I buried my face between her thighs. Her pussy was puffy, red, and slick. I could still taste traces of him—salty, musky—even though most of his load had already leaked out during the night. I licked her slowly, reverently, while she stroked my hair and told me every detail: how thick he felt stretching her, how he made her beg, how he’d spanked her ass before sliding into it for the first time. She came again on my tongue just from reliving it.

I went back to work Monday trying to act normal. Brian caught me in the hallway and gave me that same wolfish grin.

“Your wife’s an absolute freak in the sheets,” he said quietly. “Took my cock like she was made for it. Especially that tight little ass.”
I nodded, face burning, trying not to look too eager. But inside I was obsessed. I still am. Every time I see him now I picture that huge flaccid cock he showed me… and how it looked buried inside Penny.
She’s already talking about the next time.

I can’t wait.

Julia had always been clear with me: her ass was off-limits. “You’re too rough,” she’d say, turning away whenever I tried. But with my boss, 32-year-old Mark, it was different. I must add this, his cock is huge. How is he more gentle??

A couple times each week, she’ll drive from Hattiesburg to his sleek beach house in Biloxi. He’ll pour himself two shots of smooth whisky, letting the amber liquid warm him while Julia stripped slowly in the living room overlooking the Gulf.

He’d bend her over the leather couch, slick her with lube, and take her ass deep and steady—exactly the way she craved.

She moaned loud and shameless, pushing back against him until he finished inside her.

Sometimes they fuck for hours. I’m always excited to hear the details like, where did he cum? Did you kiss in public, etc.

Afterward, they’d walk the moonlit beach hand in hand, barefoot in the sand, her body still tingling from him as the waves whispered secrets neither of us would ever share.

This happened long ago. My aunt (my mom’s sister) was four years older than me. She was always flirty and fun, the cool aunt who treated me more like a friend than a nephew.
One summer afternoon at my grandparents’ place, she grabbed my arm and said, “Come on, let’s go play in the barn.” I thought it was just nostalgia, kicking around in the hayloft. We climbed up there and were laughing and throwing hay at each other when things suddenly changed.
She looked at me with this mischievous smile, pulled her pants and panties down to her ankles, and said, “Touch me.” My heart was pounding. I reached out and touched her. She was already wet and warm. After a minute she told me, “Take your pants down and put your penis on me.” I did what she said. The second I pressed against her it felt incredibly hot—like body-heat hot. We started rubbing against each other, no penetration, just grinding in the hay. It was intense and awkward and exciting all at once. I put it in, but I really didn’t know what to do. Just had a feeling of excitement.
We didn’t get much further because my uncle came out the back door and yelled, “What are y’all doing out there?!” We panicked, yanked our clothes back up, and tried to act like we were just playing around in the hay again. He gave us a suspicious look but didn’t come up. We climbed down separately a few minutes later like nothing happened.
That was my first real sexual experience. Nothing more came of it with her after that day, but damn… it’s still one of the hottest memories I have.

Hey, I’m in the Hburg area and new to the crossdressing scene. My wife helps me buy panties, but it would be nice to chat with other CD’s.