u/DDConfessions

Disclaimer: The story you are about to read is true. The names have been changed to protect the deviants I call my friends and lovers. Where the story is true, AI helped with spelling, grammar, formatting, and flow.

I am a married dad who can't get enough women. Hope that doesn't trigger you too much. You are about to read one of my true sex confessions.

Craigslist was my primary hunting ground; don't get me wrong, I picked women up on the streets too. I’d respond to anyone—guys, girls, couples, married people, whoever. I’m straight and not into men sexually, but I stay friendly with everyone. You never know who might introduce you to something (or someone) worthwhile.

I didn't need it every day. The reason for talking to so many was mostly about logistics. People’s schedules, traffic, spouses, and family obligations constantly fucked things up, so I always kept a deep bench. If one date canceled, I had another ready to go.

That philosophy led me to this day: Bob and Cindy, a boyfriend and girlfriend, then Nikki, a married mom.

Bob was a balding, overweight white guy in his mid-fifties. His girlfriend Cindy was thirty-two, white, 5’5”, around 155 pounds, with shoulder-length brown hair, massive breasts, wide childbearing hips, a thick juicy ass, strong shapely legs, and a surprisingly flat stomach. The picture Bob sent showed her in a tight one-piece swimsuit at the pool. She looked fucking incredible.

They were on vacation in Anaheim, hitting Disneyland and Knott’s Berry Farm. Bob was dying to make his threesome fantasy happen. Cindy was nervous and reluctant but willing to do it for him. We arranged to meet at a bar in the morning since they had a family obligation in the afternoon.

While texting back and forth with Bob, I was also chatting with Nikki—a sexy married Filipina woman who lived in Tustin. Her husband was a cop (in a different city), which made it risky as hell, but the danger turned me on. SEMPER FI bitches! She was just looking for a consistent FWB. She was in her 40s, short, maybe 5’2” and about 140 pounds plump. She had black hair down to her shoulders, brown eyes, large breasts, a big ass, and hips, thick shapely legs. I scheduled her as my backup for the afternoon in case Bob and Cindy flaked.

Smart money always has a contingency.

I met Bob and Cindy just after 10 a.m. at the only bar open in the area. It had a slightly sketchy vibe. Cindy looked beautiful in a black long dress, kind of like a sundress that clung to her heavy tits and wide hips, but she was visibly anxious, fidgeting with her glass. Bob, on the other hand, was buzzing with excitement. Kind of annoying, actually. He was kinda like a used car salesman... Always had a story and full of energy.

I focused on her, asking about their Disney trip, her job (Wow, you would never guess), and what she thought of Southern California. Slowly she started opening up and smiling. Bob kept jumping in, talking over her, clearly missing how important it was for her to feel comfortable with the stranger she was about to fuck.

After about forty-five minutes and a couple of drinks, Bob rubbed his hands together. “Alright, I think we’re all gonna have a great time. You guys ready to head back to the motel?”

I looked at Cindy. “Are you ok with that? No pressure.”

She downed the rest of her wine, took a breath, and said, “I'm ok, we can go.”

The motel was cheap and basic. Bob checked in while I waited with Cindy in the parking lot. When he came back, he handed me a key and pointed upstairs. Cindy stayed quiet as we entered the room. Bob immediately pulled out a bottle of Jack Daniel’s.

“Babe, go get changed,” he told her, then rushed out with the ice bucket.

I kicked off my shoes and shirt and sat against the headboard. When Bob returned, he made strong Jack and Cokes. I accepted one this time—my nerves were kicking in because Cindy still seemed uneasy.

Then she stepped out of the bathroom.

Holy fuck.

Black lace bra struggling to contain her big, heavy tits. Matching thong disappearing between her thick ass. Garter belt, sheer black stockings, and tall black heels. She’d done her makeup, and her hair looked fuller. She looked amazing.

“Wow,” I breathed. “You look incredible.”

Bob turned on a small CD player to mask the awkward silence. I know, I know, I thought the CD player was weird too... He was older, and that's what he had. What do you want me to say?

Cindy sat at the edge of the bed awkwardly. So, I crawled across the bed. “Come here. Let me rub your back while you finish your drink.”

She climbed up and leaned back against me. At first her body was stiff, but my slow, firm hands on her neck and shoulders gradually melted her tension away. I felt the goosebumps rise as I traced down her arms, her upper back, then lower. Her breathing grew deeper. She finally relaxed completely against me, eyes closed.

I glanced over. Bob was already naked, sitting on the chair next to the window, slowly stroking his thick cock while watching us.

I turned Cindy’s face toward mine and kissed her. The kiss started sweet, then quickly became hungry and deep. We slid down until we were lying on the bed. Her arms wrapped around my neck as our tongues danced. My hands roamed greedily—squeezing her heavy breasts, freeing her tits from her bra, pinching her hard nipples, gripping handfuls of her fat ass.

She reached down and eagerly unbuttoned my pants.

I stood up, stripped completely, and crawled between her spread legs. The second I pulled her thong aside and ran my tongue up her wet slit, she moaned loudly. One leg hooked around my back, the other spread wide. Her fingers gripped my hair as she ground her soaked pussy against my mouth.

“Fuck… that feels so good,” she gasped.

Bob knelt beside her head and slid his cock into her mouth. The sight of her sucking him while I ate her pussy made me throb painfully. I pushed a finger inside her tight, dripping pussy and sucked on her clit until her body tensed and she came hard, moaning around his dick.

Cindy pushed me onto my back and took my cock into her warm, eager mouth. She sucked me deep, stroking and licking like she was starving for it. Bob handed me another drink and grinned. “She tastes good, doesn’t she?”

I laughed. “Dude, you’re one lucky man.”

A few minutes later I groaned and filled her mouth with my cum. She swallowed every drop.

Then Bob took his turn. He mounted her and started fucking her hard, her big tits bouncing with every thrust. I leaned in, sucking on her nipples and kissing her deeply while he pounded her. She came twice, shaking and moaning.

When Bob pulled out, we took a small break. Grabbing water and alcohol. Then I took my place in between her legs. I teased her swollen, dripping pussy with the head of my cock, rubbing it up and down her slit until she was whimpering and trying to pull me inside. Finally I drove in deep. We locked eyes and found a perfect rhythm—her pulling me in as I thrust hard. The sound of our bodies slapping together filled the room. I filled her pussy with my second load while we kissed like lovers.

Even then we weren’t done. While Cindy and I made out, Bob spooned her from behind and slid back inside her. He must be on Viagra because he is an absolute beast! She moaned into my mouth as he fucked her, her body shaking with another orgasm.

We took a short break. Bob eventually ran out of whiskey and left to hit the liquor store. The second the door closed, the energy changed.

I pulled Cindy close. Our kisses were slow, deep, and passionate. Like lovers. I moved on top of her, slid my cock inside her soaked pussy, and with slow, long, powerful strokes, I passionately fucked her. We never broke eye contact. Our breathing synced, and sharing our breaths, breathing each other in. She wrapped her arms and legs around me, moaning softly, “You feel so good…”

We came hard together, clinging to each other, kissing each other passionately - like lovers - until Bob started talking to us when he returned. I thought to myself, I think we just made love to each other. I looked over at her, and her eyes were smiling at me. Such a beautiful woman.

Bob grinned. “Looks like you two had fun without me.”

After some downtime and light kissing. Bob suggested double penetration—something neither Cindy nor I had done before. She was drunk and horny enough to agree.

She rode me slowly, grinding her wet pussy on my cock. Bob got behind her, worked his thick cock into her tight ass, and started thrusting. The pressure was intense. Cindy gasped and trembled between us, sweat coating her skin.

“Fuck…,” she whimpered over and over.

Bob started pounding her ass harder. The intense sensation pushed me over the edge. I grabbed her by the neck, kissed her fiercely, and pumped my cum deep into her pussy while Bob continued fucking her ass.

After we caught our breath, I checked my phone. “Shit, I have to go.”

I cleaned up, got dressed, and gave Cindy a long, soft kiss goodbye. “This was amazing. I really hope I see you again.”

Bob, still naked, shook my hand at the door. “We’ll text you next time we’re in town.”

As I drove away, my body was spent, but my mind was already shifting gears. Nikki was waiting, and I had a feeling her story was going to be just as wild.

To be continued in Nikki’s story…